WO2018124087A1 - カラーフィルタ用色材分散液、カラーフィルタ用着色樹脂組成物、カラーフィルタ、及び表示装置 - Google Patents

カラーフィルタ用色材分散液、カラーフィルタ用着色樹脂組成物、カラーフィルタ、及び表示装置 Download PDF

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WO2018124087A1
WO2018124087A1 PCT/JP2017/046687 JP2017046687W WO2018124087A1 WO 2018124087 A1 WO2018124087 A1 WO 2018124087A1 JP 2017046687 W JP2017046687 W JP 2017046687W WO 2018124087 A1 WO2018124087 A1 WO 2018124087A1
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group
color material
mass
color filter
color
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PCT/JP2017/046687
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English (en)
French (fr)
Japanese (ja)
Inventor
中村　和彦
渚 井上
亘 田尻
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株式会社Ｄｎｐファインケミカル
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Priority to JP2018559523A priority Critical patent/JP7094891B2/ja
Priority to CN201780076574.9A priority patent/CN110062900A/zh
Publication of WO2018124087A1 publication Critical patent/WO2018124087A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo compounds
    • C09B45/18—Monoazo compounds containing copper
    • 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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo compounds
    • C09B45/22—Monoazo compounds containing other metals
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—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

Definitions

  • the present invention relates to a color filter color material dispersion, a color filter colored resin composition, a color filter, and a display device.
  • the color filter used in the liquid crystal display device generally defines a transparent substrate, a colored layer formed on the transparent substrate, which is composed of colored patterns of three primary colors of red, green, and blue, and each colored pattern.
  • the light shielding portion is formed on the transparent substrate.
  • a pigment dispersion method, a dyeing method, an electrodeposition method, a printing method, and the like are known.
  • a pigment dispersion method having excellent characteristics on average is most widely adopted.
  • the liquid crystal display device has a problem of viewing angle dependency due to the refractive index anisotropy of the liquid crystal cell and the polarizing plate as a specific problem.
  • This problem of viewing angle dependency is a problem that the color and contrast of an image that is visually recognized change when the liquid crystal display device is viewed from the front and when viewed from an oblique direction.
  • Such a problem of viewing angle characteristics has become more serious as the liquid crystal display device has recently been enlarged.
  • a method of incorporating a retardation film into a liquid crystal display device has been widely used.
  • the color filter used in the liquid crystal display device has a different phase difference depending on the coloring pattern of each color of the colored layer, when the above retardation film is used, the difference in the retardation of each color coloring pattern is compensated. It is difficult to completely solve the problem of viewing angle dependency.
  • Patent Document 1 discloses C.I. as a red pigment.
  • I. Pigment Red 177 (hereinafter sometimes abbreviated as PG177) and 1: 1 complex of azobarbituric acid with nickel, compatible isomers, and at least one of these compounds in the crystal lattice of other compounds.
  • PG177 Pigment Red 177
  • CI Pigment Yellow 150 derivative (Ni complex) made of at least one crystal selected from the group consisting of inserted crystals.
  • Patent Document 2 includes, as a novel metal azo pigment, a dianion of a specific azo compound and an adduct of a metal azo compound composed of at least two metal ions of Zn 2+ and Ni 2+ and melamine or a derivative thereof, A metal azo pigment having a specific signal and no specific signal in an X-ray diffraction diagram is described.
  • the present invention is excellent in color material dispersion stability and uses a color material dispersion for color filters that can form a colored layer with improved contrast while the retardation value is reduced, and the color material dispersion for the color filters.
  • Color filter colored resin composition capable of forming a colored layer with excellent color reproducibility with improved contrast while the retardation value is reduced, while the retardation value is reduced using the colored resin composition for color filter.
  • a color material dispersion for a color filter according to the present invention is a color material dispersion containing a color material, a dispersant, and a solvent,
  • the color material includes a red color material and a yellow color material
  • the yellow color material includes at least one anion selected from the group consisting of mono-, di-, tri-, and tetraanions of an azo compound represented by the following general formula (A) and an azo compound having a tautomer structure thereof:
  • the dispersing agent is a color material dispersion for a color filter, which is a polymer having a structural unit represented by the following general formula (I).
  • the colored resin composition for a color filter according to the present invention is a colored resin composition for a color filter containing a coloring material, a dispersant, a binder component, and a solvent
  • the color material includes a red color material and a yellow color material
  • the yellow color material includes at least one anion selected from the group consisting of mono-, di-, tri-, and tetraanions of an azo compound represented by the following general formula (A) and an azo compound having a tautomer structure thereof:
  • the dispersant is a colored resin composition for a color filter, which is a polymer having a structural unit represented by the following general formula (I).
  • each R a is independently —OH, —NH 2 , —NH—CN, acylamino, alkylamino, or arylamino, and each R b is independently —OH or — NH 2.
  • each R c is independently a hydrogen atom or an alkyl group.
  • R 1 is a hydrogen atom or a methyl group
  • A is a divalent linking group
  • R 2 and R 3 are each independently a hydrogen atom or a hydrocarbon that may contain a hetero atom. Represents a group, and R 2 and R 3 may combine with each other to form a ring structure.
  • the color filter according to the present invention is a color filter comprising at least a substrate and a colored layer provided on the substrate, wherein at least one of the colored layers is a colored resin composition for a color filter according to the present invention. It is the coloring layer which is a hardened
  • the present invention provides a display device comprising the color filter according to the present invention.
  • the color material dispersion liquid for color filters that is excellent in color material dispersion stability and can form a colored layer with improved contrast while the retardation value is reduced, and the color material dispersion liquid for color filters are used.
  • the color resin composition for color filters capable of forming a colored layer with excellent color reproducibility with improved contrast while the phase difference value is reduced, and the phase difference value is reduced using the color resin composition for color filter
  • a color filter with improved contrast and excellent color reproducibility and a display device with improved contrast and excellent color reproducibility while reducing the phase difference value by using the color filter. can do.
  • FIG. 1 is a schematic view showing an example of the color filter of the present invention.
  • FIG. 2 is a schematic view showing an example of the display device of the present invention.
  • FIG. 3 is a schematic view showing another example of the display device of the present invention.
  • light includes electromagnetic waves having wavelengths in the visible and invisible regions, and further includes radiation, and the radiation includes, for example, microwaves and electron beams. Specifically, it means an electromagnetic wave having a wavelength of 5 ⁇ m or less and an electron beam.
  • (meth) acryl represents each of acryl and methacryl
  • (meth) acrylate represents each of acrylate and methacrylate.
  • C.I. I. Pigment Red is “PR”
  • C.I. I. Pigment Orange as “PO”
  • C.I. I. Pigment Yellow is abbreviated as “PY” where appropriate.
  • a color material dispersion for a color filter according to the present invention is a color material dispersion containing a color material, a dispersant, and a solvent,
  • the color material includes a red color material and a yellow color material
  • the yellow color material includes at least one anion selected from the group consisting of mono-, di-, tri-, and tetraanions of an azo compound represented by the following general formula (A) and an azo compound having a tautomer structure thereof:
  • the dispersing agent is a color material dispersion for a color filter, which is a polymer having a structural unit represented by the following general formula (I).
  • each R a is independently —OH, —NH 2 , —NH—CN, acylamino, alkylamino, or arylamino, and each R b is independently —OH or — NH 2.
  • each R c is independently a hydrogen atom or an alkyl group.
  • R 1 is a hydrogen atom or a methyl group
  • A is a divalent linking group
  • R 2 and R 3 are each independently a hydrogen atom or a hydrocarbon that may contain a hetero atom. Represents a group, and R 2 and R 3 may combine with each other to form a ring structure.
  • the color material dispersion of the present invention is used in combination with the specific color material and a polymer having a structural unit represented by the general formula (I) as a dispersant, the color material dispersion stability is improved. It is possible to form a colored layer with excellent contrast while reducing the retardation value. Since many red color materials generally have an annular planar structure, since they are easy to crystallize when forming a colored layer as a color material dispersion for a color filter, the retardation in the thickness direction of the obtained colored layer The value tends to increase.
  • the red color material includes a specific yellow color material containing two or more kinds of metal ions and a weight having a specific structural unit represented by the general formula (I). Since the combination of the dispersant, which is a coalescence, is used, the interaction between the red color material and the specific yellow color material containing two or more kinds of metal ions causes the red color material and the yellow color material to be crystallized. Colored layer with improved contrast while reducing phase difference value because growth is suppressed and atomization is possible, and red color material and yellow color material are atomized and dispersed in combination with the dispersant. It is estimated that can be formed.
  • the metal forming the metal complex containing the azo compound represented by the general formula (A) is a single color material, it is difficult to atomize because of high crystallinity, and it is difficult to improve contrast. It was. Further, the retardation value of the colored layer obtained by combining with the red color material tends to be high.
  • the specific yellow color material containing 2 or more types of metal ions is used with respect to the anion of the azo compound represented by general formula (A).
  • the yellow color material contains two or more kinds of metal ions, not only the crystal growth of the yellow color material is suppressed, but also the crystal growth of the red color material is suppressed, and further, the specific dispersant is combined.
  • the red color material is combined with the specific yellow color material to obtain a P / V ratio ((color material component mass in the composition) / (solid other than the color material component in the composition). Even if the (mass ratio) ratio) is suppressed, red pixels included in the high chromaticity red chromaticity region can be produced. It is estimated that the retardation value in the thickness direction of the colored layer is reduced due to the synergistic effect that the P / V ratio is reduced in the colored layer and the crystal growth of the red color material is suppressed. .
  • the content of the binder component can be relatively increased, so that the platemaking property is improved and the adhesion to the substrate is improved. It becomes possible to form a higher colored layer.
  • the color material dispersion of the present invention contains at least a color material, a dispersant, and a solvent, and may further contain other components as long as the effects of the present invention are not impaired. .
  • each component of the color material dispersion of the present invention will be described in detail in order.
  • the color material includes a red color material and a yellow color material
  • the yellow color material includes at least one anion selected from the group consisting of mono-, di-, tri-, and tetraanions of an azo compound represented by the following general formula (A) and an azo compound having a tautomer structure thereof:
  • the specific yellow color material is used as a yellow color material, a decrease in luminance can be suppressed when combined with a red color material, and crystallization is suppressed and atomization is possible. Since it is excellent in dispersibility when combined with a specific dispersant described later, the contrast can be improved and the retardation value can be reduced.
  • each R a is independently —OH, —NH 2 , —NH—CN, acylamino, alkylamino, or arylamino, and each R b is independently —OH or — NH 2.
  • Examples of the acyl group in the acylamino group in the general formula (A) include, for example, an alkylcarbonyl group, a phenylcarbonyl group, an alkylsulfonyl group, a phenylsulfonyl group, an alkyl, phenyl, or a carbamoyl group that may be substituted with naphthyl, an alkyl , Sulfamoyl group optionally substituted with phenyl or naphthyl, guanyl group optionally substituted with alkyl, phenyl or naphthyl, and the like.
  • the alkyl group preferably has 1 to 6 carbon atoms.
  • the alkyl group may be substituted with, for example, a halogen such as F, Cl, or Br, —OH, —CN, —NH 2 , and / or an alkoxy group having 1 to 6 carbon atoms.
  • the phenyl group and naphthyl group are, for example, halogen such as F, Cl and Br, —OH, —CN, —NH 2 , —NO 2 , an alkyl group having 1 to 6 carbon atoms, and / or 1 carbon atom. It may be substituted with 6 or less alkoxy groups.
  • the alkyl group in the alkylamino group in the general formula (A) preferably has 1 to 6 carbon atoms.
  • the alkyl group may be substituted with, for example, a halogen such as F, Cl, or Br, —OH, —CN, —NH 2 , and / or an alkoxy group having 1 to 6 carbon atoms.
  • a halogen such as F, Cl, or Br
  • —OH, —CN —NH 2
  • / or an alkoxy group having 1 to 6 carbon atoms examples include a phenyl group and a naphthyl group.
  • These aryl groups include, for example, halogens such as F, Cl, and Br, —OH, and those having 1 to 6 carbon atoms.
  • the alkyl group, an alkoxy group having 1 to 6 carbon atoms, —NH 2 , —NO 2, and —CN may be substituted.
  • each R a is independently —OH, —NH 2 , —NH—CN, or alkylamino. It is preferable from the viewpoint comprising a reddish hue, the two R a may be different even in the same, respectively.
  • two R a s are, in terms of hue, when both are —OH, both are —NH—CN, or one is —OH and one is —NH—. More preferably, it is CN, and even more preferably both are —OH.
  • R b is more preferably —OH from the viewpoint of hue.
  • the at least two kinds of metals selected from the group consisting of Cd, Co, Al, Cr, Sn, Pb, Zn, Fe, Ni, Cu, and Mn a metal that becomes a divalent or trivalent cation is used. It is preferable to include at least one, preferably at least one selected from the group consisting of Ni, Cu, and Zn, and more preferably at least Ni. Furthermore, it is preferable that Ni and at least one metal selected from the group consisting of Cd, Co, Al, Cr, Sn, Pb, Zn, Fe, Cu, and Mn are further included. Furthermore, it is preferable that at least one metal selected from the group consisting of Zn, Cu, Al and Fe is included. In particular, the at least two metals are preferably Ni and Zn, or Ni and Cu.
  • the content ratio of at least two metals may be appropriately adjusted.
  • the yellow color material used in the present invention is selected from the group consisting of Ni and further Cd, Co, Al, Cr, Sn, Pb, Zn, Fe, Cu and Mn.
  • the content ratio with the at least one metal is preferably such that Ni: the other at least one metal is contained in a molar ratio of 97: 3 to 10:90, and more preferably a mole of 90:10 to 10:90. It is preferable to include by ratio.
  • Ni and Zn are preferably included in a molar ratio of Ni: Zn of 90:10 to 10:90, and more preferably 80:20 to 20:80. preferable.
  • Ni and Cu are preferably included in a molar ratio of Ni: Cu of 97: 3 to 10:90, and more preferably in a molar ratio of 96: 4 to 20:80. preferable.
  • the yellow color material has a red hue, it is easy to produce a red pixel included in the high chromaticity red chromaticity region even if the P / V ratio is suppressed.
  • the yellow color material used in the present invention may further contain metal ions different from the specific metal ions.
  • the yellow color material used in the present invention may contain, for example, at least one metal ion selected from the group consisting of Li, Cs, Mg, Na, K, Ca, Sr, Ba, and La. .
  • the common crystal lattice includes at least two kinds of metal ions or whether another crystal lattice includes one type of metal ion each aggregated. For example, it can be appropriately determined by using an X-ray diffraction method with reference to JP-A-2014-12838.
  • the yellow color material used in the present invention further contains a compound represented by the following general formula (B).
  • the yellow color material used in the present invention comprises a metal complex comprising an anion of an azo compound represented by the general formula (A) and an azo compound having a tautomeric structure thereof and a specific metal ion, and the following general formula (B).
  • numerator with the compound represented by this is included.
  • the bonds between these molecules can be formed, for example, by intermolecular interactions, by Lewis acid-base interactions, or by coordinate bonds.
  • a structure such as an inclusion compound in which a guest molecule is incorporated in a lattice constituting a host molecule may be used.
  • a mixed substitution crystal may be formed in which two substances form a joint crystal, and atoms of the second component are located at regular lattice positions of the first component.
  • each R c is independently a hydrogen atom or an alkyl group.
  • the alkyl group for R c is preferably an alkyl group having 1 to 6 carbon atoms, and more preferably an alkyl group having 1 to 4 carbon atoms.
  • the alkyl group may be substituted with an —OH group.
  • R c is preferably a hydrogen atom.
  • the content of the compound represented by the general formula (B) is generally based on 1 mol of the azo compound represented by the general formula (A) and the azo compound having a tautomeric structure thereof. 5 mol to 300 mol, preferably 10 mol to 250 mol, and more preferably 100 mol to 200 mol.
  • the yellow color material used in the present invention further includes urea and substituted ureas such as phenylurea and dodecylurea, and polycondensates thereof with aldehydes, particularly formaldehyde; heterocycles such as barbituric acid and benzimidazo.
  • urea and substituted ureas such as phenylurea and dodecylurea, and polycondensates thereof with aldehydes, particularly formaldehyde; heterocycles such as barbituric acid and benzimidazo.
  • Ron benzimidazolone-5-sulfonic acid, 2,3-dihydroxyquinoxaline, 2,3-dihydroxyquinoxaline-6-sulfonic acid, carbazole, carbazole-3,6-disulfonic acid, 2-hydroxyquinoline, 2,4- Contains dihydroxyquinoline, caprolactam, melamine, 6-phenyl-1,3,5-triazine-2,4-diamine, 6-methyl-1,3,5-triazine-2,4-diamine, cyanuric acid, etc. May be.
  • the yellow color material used in the present invention further includes a water-soluble polymer such as ethylene-propylene oxide block polymer, polyvinyl alcohol, poly (meth) acrylic acid such as carboxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, methyl.
  • a water-soluble polymer such as ethylene-propylene oxide block polymer, polyvinyl alcohol, poly (meth) acrylic acid such as carboxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, methyl.
  • -And modified cellulose such as ethyl hydroxyethyl cellulose may be included.
  • the yellow color material used in the present invention can be prepared by referring to, for example, JP-A-2014-12838.
  • a colorant having a transmittance at a wavelength of 520 nm of 20% or less and a transmittance of a wavelength of 640 nm of 70% or more is used.
  • the red color material used in the present invention is a slightly yellowish red color material (an orange material with strong redness). I. A coloring material denoted as pigment orange is also included.
  • a red color material in order to measure the color of a red color material as a single unit, an appropriate dispersant, binder component and solvent are mixed with the red color material to prepare a coating solution, which is then coated on a transparent substrate. May be dried and cured as necessary.
  • a binder component a non-curable thermoplastic resin composition may be used as long as a transparent coating film capable of performing colorimetry can be formed, or a photo-curable (photosensitive) or thermosetting resin composition. May be used.
  • a coating film containing only a red color material as a color material may be formed and colorimetry may be performed. it can.
  • the solid content used in the resin composition of Example 1 described later can be used as a solid content other than the red color material.
  • a transparent coating film including a dispersant and a binder component that can perform colorimetry for example, the film thickness is 2.0 ⁇ m, and the transmittance of the spectral transmittance spectrum at 380 to 780 nm is 95% or more. can do.
  • the spectral transmittance spectrum can be measured using a spectroscopic measurement device (for example, an Olympus microscope OSP-SP200).
  • the measurement condition is a C light source.
  • the red color material used in the present invention is not particularly limited. Examples include perylene pigments and thioindigo pigments.
  • the red color material used in the present invention is at least one selected from the group consisting of a diketopyrrolopyrrole pigment, a naphthol azo pigment, an anthraquinone pigment, and a perylene pigment from the viewpoint of suppressing the P / V ratio. It is preferable to include a seed, and further, from the viewpoint of easily forming a hue of high color density and high brightness, it further includes at least one selected from the group consisting of a diketopyrrolopyrrole pigment and an anthraquinone pigment. preferable.
  • Examples of the diketopyrrolopyrrole pigment include those represented by the following general formula (1).
  • a 3 and A 4 are each independently a halogen atom, methyl group, ethyl group, tert-butyl group, phenyl group, N, N-dimethylamino group, trifluoromethyl group, or A cyano group, k and k ′ each independently represent an integer of 0 or more and 5 or less, and when k and k ′ are each an integer of 2 or more, a plurality of A 3 and A 4 may be the same May be different.
  • diketopyrrolopyrrole pigment examples include C.I. I. Pigment red 254, C.I. I. Pigment red 255, C.I. I. Pigment red 264, C.I. I. Pigment red 270, C.I. I. Pigment red 272, C.I. I. Pigment orange 71, C.I. I. Pigment Orange 73, and diketopyrrolopyrrole pigment (BrDPP) represented by the following chemical formula (2).
  • naphthol-based azo pigment examples include C.I. I. Pigment red 144, C.I. I. Pigment red 166, C.I. I. Pigment red 214, C.I. I. Pigment red 242, C.I. I. Pigment red 21, C.I. I. Pigment red 2, C.I. I. Pigment red 112, C.I. I. Pigment red 114, C.I. I. Pigment red 5, C.I. I. Pigment red 146, C.I. I. Pigment red 170, C.I. I. Pigment orange 38, C.I. I. Pigment red 187, C.I. I. Pigment red 150, C.I. I. And CI Pigment Red 185.
  • Other azo pigments include C.I. I. Pigment red 38, C.I. I. Pigment red 41 etc. are mentioned.
  • the anthraquinone pigments include C.I. I. Pigment red 177, C.I. I. Pigment red 168, C.I. I. And CI Pigment Orange 51.
  • red color material As the red color material, C.I. I. Pigment red 254, C.I. I. Pigment red 264, C.I. I. Pigment Red 272, a diketopyrrolopyrrole pigment (BrDPP) represented by the above chemical formula (2), C.I. I. Pigment red 242, C.I. I. Pigment orange 38, C.I. I. Pigment red 177, and C.I. I. It is preferable to use one or more red color materials selected from the group consisting of CI Pigment Red 179. I. Pigment Red 254, a diketopyrrolopyrrole pigment (BrDPP) represented by the above chemical formula (2), C.I. I. A combination with Pigment Red 177 is preferably used. C. I.
  • Pigment Red 254 a diketopyrrolopyrrole pigment (BrDPP) represented by the above chemical formula (2), C.I. I.
  • the content ratio in the case of combining with Pigment Red 177 is not particularly limited as long as it is appropriately adjusted according to the desired color material.
  • Pigment Red 254 is 10 to 80 parts by mass
  • the diketopyrrolopyrrole pigment (BrDPP) represented by the chemical formula (2) is 10 to 70 parts by mass
  • the content rate of the said red color material is a preferable rate at the time of setting it as the below-mentioned colored resin composition
  • a colored resin composition can be manufactured using 2 or more types of color material dispersions suitably mixed. Therefore, the color material dispersion itself is preferably used even if it does not have the same content ratio as that of the colored resin composition described later.
  • a red color material and the specific yellow color material are used in combination as a color material, but other color materials such as those exemplified in the colored resin composition described below are used in combination. May be.
  • other color materials for example, other yellow color materials, orange color materials not included in the red color material, and the like are preferably used.
  • the yellow color material is preferably used.
  • each content ratio of the red color material and the specific yellow color material, and the content ratio in the case of using other color materials are the same content ratio as that of the color resin composition described later. It is preferable to do.
  • two or more colorant dispersions can be appropriately mixed and used to produce a colored resin composition, so that the colorant dispersion is preferably used even if the content ratio is not the same as that of the later-described colored resin composition.
  • the average primary particle size of the color material used in the present invention is not particularly limited as long as it can produce a desired color when it is used as a color layer of a color filter, and varies depending on the type of color material used. Is preferably in the range of 10 nm to 100 nm, more preferably 15 nm to 60 nm. When the average primary particle diameter of the color material is in the above range, a display device including a color filter manufactured using the color material dispersion of the present invention can be made with high contrast and high quality. .
  • the average dispersed particle diameter of the color material in the color material dispersion varies depending on the type of the color material used, it is preferably in the range of 10 nm to 100 nm, and preferably in the range of 15 nm to 60 nm. More preferred.
  • the average dispersed particle size of the color material in the color material dispersion is the dispersed particle size of the color material particles dispersed in a dispersion medium containing at least a solvent, and is measured by a laser light scattering particle size distribution meter. It is.
  • the color material dispersion is appropriately diluted to a concentration that can be measured with a laser light scattering particle size distribution meter (for example, 1000 times). Etc.) and can be measured at 23 ° C. by a dynamic light scattering method using a laser light scattering particle size distribution meter (for example, Nanotrack particle size distribution measuring device UPA-EX150 manufactured by Nikkiso Co., Ltd.).
  • the average distribution particle size here is a volume average particle size.
  • the content of the color material is not particularly limited.
  • the content of the color material is 5 parts by mass or more and 80 parts by mass or less, more preferably 8 parts by mass or more and 70 parts by mass with respect to 100 parts by mass of the total solid content in the color material dispersion from the viewpoint of dispersibility and dispersion stability. It is preferable to mix
  • it is 30 parts by mass or more and 80 parts by mass or less, more preferably 40 parts by mass or more with respect to 100 parts by mass of the total solid content in the color material dispersion. It is preferable to mix at a ratio of 75 parts by mass or less.
  • a polymer having a structural unit represented by the general formula (I) is used as a dispersant.
  • the structural unit represented by the general formula (I) has basicity and functions as an adsorption site for a coloring material.
  • the color material dispersion of the present invention improves the adsorption performance to the color material, and improves the dispersibility and dispersion stability of the color material. To do.
  • A is a divalent linking group.
  • the divalent linking group in A include an alkylene group having 1 to 10 carbon atoms, an arylene group, a —CONH— group, a —COO— group, and an ether group having a carbon atom number of 1 to 10 (—R ′).
  • R ′ and R ′′ are each independently an alkylene group) and combinations thereof.
  • a in the general formula (I) is preferably a divalent linking group containing a —CONH— group or a —COO— group.
  • Examples of the hydrocarbon group in the hydrocarbon group that may include a hetero atom in R 2 and R 3 include an alkyl group, an aralkyl group, and an aryl group.
  • Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, a tert-butyl group, a 2-ethylhexyl group, a cyclopentyl group, a cyclohexyl group, and the like. It is preferably 1 or more and 18 or less, and more preferably a methyl group or an ethyl group.
  • Examples of the aralkyl group include a benzyl group, a phenethyl group, a naphthylmethyl group, and a biphenylmethyl group.
  • the number of carbon atoms in the aralkyl group is preferably 7 or more and 20 or less, and more preferably 7 or more and 14 or less.
  • Examples of the aryl group include a phenyl group, a biphenyl group, a naphthyl group, a tolyl group, and a xylyl group.
  • the number of carbon atoms of the aryl group is preferably 6 or more and 24 or less, and more preferably 6 or more and 12 or less.
  • the preferred number of carbon atoms does not include the number of carbon atoms of the substituent.
  • the hydrocarbon group containing a hetero atom has a structure in which a carbon atom in the hydrocarbon group is replaced with a hetero atom.
  • the hetero atom that the hydrocarbon group may contain include an oxygen atom, a nitrogen atom, a sulfur atom, and a silicon atom.
  • the hydrogen atom in the hydrocarbon group may be substituted with a halogen atom such as an alkyl group having 1 to 5 carbon atoms, a fluorine atom, a chlorine atom, or a bromine atom.
  • R 2 and R 3 are bonded to each other to form a ring structure” means that R 2 and R 3 form a ring structure through a nitrogen atom.
  • the ring structure formed by R 2 and R 3 may contain a hetero atom.
  • the ring structure is not particularly limited, and examples thereof include a pyrrolidine ring, a piperidine ring, and a morpholine ring.
  • R 2 and R 3 are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a phenyl group, or R 2 and R 3 are bonded to form a pyrrolidine ring.
  • a piperidine ring and a morpholine ring are preferable, and among them, at least one of R 2 and R 3 is an alkyl group having 1 to 5 carbon atoms, a phenyl group, or R 2 and R 3.
  • Examples of the structural unit represented by the general formula (I) include dimethylaminoethyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, diethylaminoethyl (meth) acrylate, diethylaminopropyl (meth) acrylate, and other alkyl group-substituted amino groups.
  • Examples include group-containing (meth) acrylates, alkyl group-substituted amino group-containing (meth) acrylamides such as dimethylaminoethyl (meth) acrylamide, dimethylaminopropyl (meth) acrylamide, and the like.
  • dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, and dimethylaminopropyl (meth) acrylamide can be preferably used in terms of improving dispersibility and dispersion stability.
  • the structural unit represented by the general formula (I) may be composed of one type or may include two or more types of structural units.
  • the polymer having the structural unit represented by the general formula (I) preferably further includes a portion having solvent affinity from the viewpoint of improving dispersibility.
  • a monomer having an ethylenically unsaturated bond that can be polymerized with a monomer that derives the structural unit represented by the general formula (I) is selected depending on the solvent so as to have solvent affinity. It is preferable to select and use as appropriate. As a standard, it is preferable to introduce a solvent-affinity site so that the solubility of the polymer at 23 ° C. is 50 (g / 100 g solvent) or more with respect to the solvent used in combination.
  • a block copolymer can be formed from the viewpoint that the dispersibility and dispersion stability of the coloring material and the heat resistance of the resin composition can be improved and a colored layer having high brightness and high contrast can be formed.
  • a graft copolymer is preferable and a block copolymer is particularly preferable.
  • particularly preferred block copolymers will be described in detail.
  • Block copolymer When the block containing the structural unit represented by the general formula (I) is an A block, the structural unit represented by the general formula (I) is basic and the A block has an adsorption site for a coloring material. Function as. On the other hand, the B block not containing the structural unit represented by the general formula (I) functions as a block having solvent affinity.
  • the arrangement of each block of the block copolymer is not particularly limited, and for example, an AB block copolymer, an ABA block copolymer, a BAB block copolymer, and the like can be used. Among these, an AB block copolymer or an ABA block copolymer is preferable in terms of excellent dispersibility.
  • Examples of the structural unit constituting the B block include a monomer having an unsaturated double bond copolymerizable with the monomer that derives the structural unit represented by the general formula (I).
  • the structural unit represented by (II) is preferred.
  • a ′ is a direct bond or a divalent linking group
  • R 4 is a hydrogen atom or a methyl group
  • R 5 is a hydrocarbon group, — [CH (R 6 ) —CH (R 7 ) —O] x —R 8 or — [(CH 2 ) y —O] z —R 8.
  • R 6 and R 7 is independently a hydrogen atom or a methyl group.
  • R 8 is a hydrogen atom, a hydrocarbon group, a monovalent group represented by —CHO, —CH 2 CHO, or —CH 2 COOR 9
  • R 9 is a hydrogen atom or a carbon atom number of 1 or more and 5 or less. It is an alkyl group.
  • the hydrocarbon group may have a substituent.
  • x represents an integer of 1 to 30, y represents an integer of 1 to 5, and z represents an integer of 1 to 18.
  • the divalent linking group A ′ in the general formula (II) can be the same as A in the general formula (I).
  • a ′ is preferably a divalent linking group containing a direct bond, —CONH— group, or —COO— group from the viewpoint of solubility in an organic solvent.
  • solubility in propylene glycol monomethyl ether acetate (PGMEA) suitably used as a solvent, and a relatively inexpensive material
  • a ′ may be a —COO— group. preferable.
  • the hydrocarbon group for R 5 is preferably an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an aralkyl group, or an aryl group.
  • the alkyl group having 1 to 18 carbon atoms may be linear, branched or cyclic.
  • a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group examples include 2-ethylhexyl group, 2-ethoxyethyl group, cyclopentyl group, cyclohexyl group, bornyl group, isobornyl group, dicyclopentanyl group, dicyclopentenyl group, adamantyl group, and lower alkyl group-substituted adamantyl group.
  • the alkenyl group having 2 to 18 carbon atoms may be linear, branched or cyclic.
  • Examples of such an alkenyl group include a vinyl group, an allyl group, and a propenyl group.
  • the position of the double bond of the alkenyl group is not limited, but from the viewpoint of the reactivity of the polymer obtained, it is preferable that there is a double bond at the terminal of the alkenyl group.
  • Examples of the aliphatic hydrocarbon substituent such as an alkyl group or an alkenyl group include a nitro group and a halogen atom.
  • aryl group examples include a phenyl group, a biphenyl group, a naphthyl group, a tolyl group, and a xylyl group, and may further have a substituent.
  • the number of carbon atoms of the aryl group is preferably 6 or more and 24 or less, and more preferably 6 or more and 12 or less.
  • aralkyl group a benzyl group, a phenethyl group, a naphthylmethyl group, a biphenylmethyl group, etc. are mentioned, Furthermore, you may have a substituent.
  • the number of carbon atoms in the aralkyl group is preferably 7 or more and 20 or less, and more preferably 7 or more and 14 or less.
  • substituent on the aromatic ring such as an aryl group and an aralkyl group include straight chain and branched alkyl groups having 1 to 4 carbon atoms, alkenyl groups, nitro groups, and halogen atoms.
  • the preferred number of carbon atoms does not include the number of carbon atoms of the substituent.
  • x is an integer of 1 or more and 30 or less, preferably an integer of 1 or more and 26 or less, more preferably an integer of 1 or more and 18 or less, still more preferably 1 or more and 4 or less, particularly preferably 1 or more and 2 Y is an integer of 1 or more and 5 or less, preferably an integer of 1 or more and 4 or less, more preferably 2 or 3.
  • z is an integer of 1 or more and 18 or less, preferably an integer of 1 or more and 4 or less, more preferably an integer of 1 or more and 2 or less.
  • the hydrocarbon group for R 8 can be the same as that shown for R 5 .
  • the hydrocarbon group for R 8 is preferably an alkyl group having 1 to 18 carbon atoms from the viewpoint of excellent developability.
  • R 9 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and may be linear, branched or cyclic.
  • R 5 in the structural unit represented by the general formula (II) may be the same or different from each other.
  • the R 5 is preferably selected so as to be excellent in compatibility with a solvent described later.
  • the solvent is generally used as a solvent for a colored resin composition for a color filter.
  • a commonly used solvent such as glycol ether acetate, ether or ester is used, a methyl group, an ethyl group, an isobutyl group, an n-butyl group, a 2-ethylhexyl group, a benzyl group or the like is preferable.
  • R 5 In the structural unit constituting the B block, as R 5 , — [CH (R 6 ) —CH (R 7 ) —O] x —R 8 or — [(CH 2 ) y —O] z — It contains what is R 8 is, excellent developability, from the viewpoint of excellent suppression of development residue.
  • R 5 may be substituted with a substituent such as an alkoxy group, a hydroxyl group, an epoxy group, or an isocyanate group as long as the dispersion performance of the block copolymer is not hindered.
  • the substituent may be added by reacting with the compound having the substituent.
  • the glass transition temperature (Tg) of the solvent-compatible block part of the block copolymer may be appropriately selected.
  • the glass transition temperature (Tg) of the solvent-compatible block part is preferably 80 ° C. or higher, and more preferably 100 ° C. or higher.
  • the glass transition temperature (Tg) of the solvent-affinity block part in the present invention can be calculated by the following formula.
  • Tgi is the glass transition temperature (absolute temperature) of the homopolymer of the i-th monomer.
  • the homopolymer glass transition temperature value (Tgi) of each monomer may adopt the value of Polymer Handbook (3rd Edition) (by J. Brandrup, EH Immergut (Wiley-Interscience, 1989)). it can.
  • the number of structural units constituting the solvent affinity block may be appropriately adjusted within a range where the colorant dispersibility is improved.
  • the number of structural units constituting the solvent-affinity block part is 10 or more and 200 or less from the viewpoint that the solvent-affinity part and the colorant affinity part act effectively and improve the dispersibility of the colorant.
  • it is 10 or more and 100 or less, more preferably 10 or more and 70 or less.
  • the solvent-affinity block part may be selected so as to function as a solvent-affinity site, and the repeating unit constituting the solvent-affinity block part may be composed of one kind, or two or more kinds.
  • the repeating unit may be included.
  • the dispersant is a polymer having a structure represented by the general formula (II) and having an amine value of 40 mgKOH / g to 120 mgKOH / g. It is preferable from the viewpoint of improving luminance and contrast without depositing foreign matters.
  • the amine value is within the above range, the viscosity is excellent in stability over time and heat resistance, and is also excellent in alkali developability and solvent resolubility.
  • the amine value of the dispersant is preferably 80 mgKOH / g or more, more preferably 90 mgKOH / g or more, from the viewpoint of dispersibility and dispersion stability.
  • the amine value of the dispersant is preferably 110 mgKOH / g or less, more preferably 105 mgKOH / g or less.
  • the amine value refers to the number of mg of potassium hydroxide equivalent to perchloric acid required to neutralize the amine component contained in 1 g of a sample, and can be measured by the method defined in JIS-K7237. When measured by this method, even if it is an amino group that forms a salt with the organic acid compound in the dispersant, the organic acid compound usually dissociates, so that the block copolymer itself used as the dispersant is itself The amine value of can be measured.
  • the acid value of the dispersant used in the present invention is preferably 1 mgKOH / g or more as a lower limit from the viewpoint of the effect of suppressing development residue.
  • the acid value of the dispersant is more preferably 2 mgKOH / g or more from the viewpoint of more excellent development residue suppression effect.
  • the acid value of the dispersant is preferably 0 mgKOH / g from the viewpoint of dispersibility and dispersion stability.
  • the acid value of the dispersant used in the present invention is 18 mgKOH / g or less as the upper limit of the acid value of the dispersant from the viewpoint of preventing deterioration in development adhesion and solvent resolubility. preferable.
  • the acid value of the dispersant is more preferably 12 mgKOH / g or less, and even more preferably 8 mgKOH / g or less, from the viewpoint that the development adhesion and the solvent re-solubility are improved.
  • the acid value of the block copolymer before salt formation is preferably 1 mgKOH / g or more, and more preferably 2 mgKOH / g or more. This is because the effect of suppressing the development residue is improved.
  • the acid value of the block copolymer before salt formation is preferably 0 mgKOH / g from the viewpoint of dispersibility and dispersion stability.
  • the upper limit of the acid value of the block copolymer before salt formation is preferably 18 mgKOH / g or less, more preferably 12 mgKOH / g or less, and even more preferably 8 mgKOH / g or less. . This is because the development adhesiveness and the solvent resolubility are improved.
  • the glass transition temperature of a dispersing agent is 30 degreeC or more from the point which image development adhesiveness improves. That is, whether the dispersant is a block copolymer before salt formation or a salt block copolymer, the glass transition temperature is preferably 30 ° C. or higher.
  • the glass transition temperature of the dispersant is low, it is particularly close to the developer temperature (usually about 23 ° C.), and the development adhesion may be lowered. This is presumably because when the glass transition temperature is close to the developer temperature, the movement of the dispersant increases during development, resulting in poor development adhesion.
  • the glass transition temperature is 30 ° C.
  • the amount of the binder is relatively decreased, so that the colored resin layer is easily peeled off from the base substrate during development.
  • the dispersant contains a B block containing a structural unit derived from a carboxy group-containing monomer and has the specific acid value and glass transition temperature, the development adhesion is improved. If the acid value is too high, the developability is excellent, but it is presumed that the polarity is too high and peeling easily occurs during development.
  • the dispersant is a polymer having a structure represented by the general formula (I) and having an amine value of 40 mgKOH / g or more and 120 mgKOH / g or less, and an acid value.
  • 1 mgKOH / g or more and 18 mgKOH / g or less and a glass transition temperature of 30 ° C. or more is excellent in colorant dispersion stability, improves contrast, and suppresses generation of development residue when a colored resin composition is obtained.
  • the carboxy group-containing monomer a monomer that can be copolymerized with a monomer having a structural unit represented by the general formula (I) and contains an unsaturated double bond and a carboxy group can be used.
  • monomers include (meth) acrylic acid, vinyl benzoic acid, maleic acid, maleic acid monoalkyl ester, fumaric acid, itaconic acid, crotonic acid, cinnamic acid, acrylic acid dimer, and the like.
  • an addition reaction product of a monomer having a hydroxyl group such as 2-hydroxyethyl (meth) acrylate and a cyclic anhydride such as maleic anhydride, phthalic anhydride, or cyclohexanedicarboxylic anhydride, ⁇ -carboxy-polycaprolactone Mono (meth) acrylates can also be used.
  • a cyclic anhydride such as maleic anhydride, phthalic anhydride, or cyclohexanedicarboxylic anhydride, ⁇ -carboxy-polycaprolactone Mono (meth) acrylates
  • acid anhydride group containing monomers such as maleic anhydride, itaconic anhydride, and citraconic anhydride, as a precursor of a carboxy group.
  • (meth) acrylic acid is particularly preferable from the viewpoints of copolymerizability, cost, solubility, glass transition temperature, and the like.
  • the content ratio of the structural unit derived from the carboxy group-containing monomer may be appropriately set so that the acid value of the block copolymer is within the range of the specific acid value.
  • it is preferable that it is 0.05 mass% or more and 4.5 mass% or less with respect to the total mass of all the structural units of a block copolymer, and is 0.07 mass% or more and 3.7 mass% or less. More preferably.
  • the structural unit derived from the carboxy group-containing monomer Since the content ratio of the structural unit derived from the carboxy group-containing monomer is not less than the lower limit value, the effect of suppressing the development residue is expressed, and since it is not more than the upper limit value, the development adhesiveness is deteriorated and the solvent resolubility is reduced. Deterioration can be prevented.
  • the structural unit derived from a carboxy group containing monomer should just become said specific acid value, may consist of 1 type, and may contain 2 or more types of structural units.
  • the monomer whose glass transition temperature (Tgi) of the homopolymer of the monomer is 10 ° C. or higher from the viewpoint that the glass transition temperature of the dispersant used in the present invention is a specific value or higher and development adhesion is improved.
  • Tgi glass transition temperature of the homopolymer of the monomer
  • the ratio m / n of the unit number m of the structural unit of the A block and the unit number n of the structural unit of the B block is in the range of 0.05 to 1.5. In view of the dispersibility and dispersion stability of the coloring material, it is more preferably within the range of 0.1 to 1.0.
  • the weight average molecular weight Mw of the block copolymer is not particularly limited, but is preferably 1000 or more and 20000 or less, and preferably 2000 or more and 15000 or less, from the viewpoint of improving the colorant dispersibility and dispersion stability. More preferably, it is more preferably 3000 or more and 12000 or less.
  • the weight average molecular weight (Mw) is determined as a standard polystyrene equivalent value by gel permeation chromatography (GPC).
  • GPC gel permeation chromatography
  • the method for producing the block copolymer is not particularly limited. Although a block copolymer can be produced by a known method, it is preferable to produce it by a living polymerization method. This is because chain transfer and deactivation are unlikely to occur, a copolymer having a uniform molecular weight can be produced, and dispersibility and the like can be improved.
  • the living polymerization method include a living anionic polymerization method such as a living radical polymerization method and a group transfer polymerization method, and a living cation polymerization method.
  • a copolymer can be produced by sequentially polymerizing monomers by these methods.
  • a block copolymer can be produced by first producing the A block and polymerizing the structural units constituting the B block into the A block.
  • the order of polymerization of the A block and the B block can be reversed.
  • the A block and the B block can be manufactured separately, and then the A block and the B block can be coupled.
  • block copolymer having a block part containing the structural unit represented by the general formula (I) and a block part having a solvent affinity include, for example, those described in Japanese Patent No. 4911253 A block copolymer can be mentioned as a suitable thing.
  • the polymer containing the structural unit represented by the general formula (I) an organic acid compound
  • a salt formed with a halogenated hydrocarbon as a dispersant
  • the polymer containing a repeating unit having a tertiary amine is a block copolymer
  • the organic acid compound is an acidic organic phosphorus compound such as phenylphosphonic acid or phenylphosphinic acid. And preferred from the viewpoint of excellent dispersion stability.
  • organic acid compound used for such a dispersant examples include, for example, organic acid compounds described in JP 2012-236882 A and the like.
  • the halogenated hydrocarbon is preferably at least one of allyl halides such as allyl bromide and benzyl chloride and aralkyl halides from the viewpoint of excellent dispersibility and dispersion stability of the coloring material.
  • the dispersant at least one polymer having the structural unit represented by the general formula (I) is used, and the content thereof is the type of the color material to be used, and further described below. It is appropriately selected according to the solid content concentration in the colored resin composition for color filter to be performed.
  • the content of the dispersant is 3 parts by mass or more and 45 parts by mass or less, more preferably 5 parts by mass or more and 35 parts by mass with respect to 100 parts by mass of the total solid content in the colorant dispersion from the viewpoint of dispersibility and dispersion stability. It is preferable to mix
  • the content of the dispersant is 3 parts by mass or more and 25 parts by mass or less with respect to 100 parts by mass of the total solid content in the color material dispersion. More preferably, it is blended at a ratio of 5 parts by mass or more and 20 parts by mass or less.
  • the solid content is everything except the above-mentioned solvent, and includes monomers dissolved in the solvent.
  • the solvent used in the present invention is not particularly limited as long as it is an organic solvent that does not react with each component in the colorant dispersion and can dissolve or disperse them.
  • a solvent can be used individually or in combination of 2 or more types.
  • Specific examples of the solvent include, for example, alcohol solvents such as methyl alcohol, ethyl alcohol, i-propyl alcohol and methoxy alcohol; carbitol solvents such as methoxyethoxyethanol and ethoxyethoxyethanol; ethyl acetate, butyl acetate and methoxypropion Ester solvents such as methyl acid, ethyl methoxypropionate, ethyl ethoxypropionate, ethyl lactate, methyl hydroxypropionate, ethyl hydroxypropionate, n-butyl acetate, isobutyl acetate, n-butyl butyrate, clohexanol acetate; acetone, Ke
  • the solvent used in the present invention includes propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, 2-methoxyethyl acetate, propylene glycol monomethyl ether, diethylene glycol ethyl methyl ether, butyl carbitol acetate (BCA), 3-methoxy It should be at least one selected from the group consisting of -3-methyl-1-butyl acetate, ethyl lactate, methyl 2-hydroxypropionate, and 3-methoxybutyl acetate. It is preferable from the point of aptitude.
  • the glycol ether acetate described above is used as the first solvent because of its high safety; moderate volatility; good dispersibility due to moderate solubility; It is preferable to use a system solvent.
  • a system solvent 2-methoxyethyl acetate or propylene glycol monomethyl ether acetate having a boiling point (boiling point at atmospheric pressure; the same shall apply hereinafter) of less than 150 ° C. is more preferable, and propylene glycol monomethyl ether acetate (PGMEA) is particularly preferable. preferable.
  • a solvent having an alcoholic hydroxyl group or a solvent having a boiling point of 150 ° C. or higher is preferable.
  • a 2nd solvent may be used individually by 1 type, and 2 or more types may be mixed and used for it.
  • the dispersibility is improved and the solvent resolubility is likely to be improved.
  • the solvent having an alcoholic hydroxyl group include the alcohol solvent, the carbitol solvent, and the glycol ether solvent. Specific examples include propylene glycol monomethyl ether (boiling point 121 ° C.), 3-methoxy- Examples include 3-methyl-1-butanol (boiling point 174 ° C.).
  • the content of the solvent having an alcoholic hydroxyl group is preferably 10% by mass or less, more preferably 5% by mass or less, and still more preferably 2% by mass or less in the total solvent. Moreover, 0.1 mass% or more is preferable, 0.3 mass% or more is more preferable, and 1 mass% or more is still more preferable. Within the above range, the solubility of the dispersant tends to be good, and since the dissolution of the dispersant in the first solvent is not hindered, the dispersion stability tends to be good.
  • the first solvent is a solvent having a boiling point of less than 150 ° C.
  • use of a solvent having a boiling point of 150 ° C. or more as the second solvent makes it difficult for drying unevenness to occur, hardly causes foreign matter, and tends to improve the solvent resolubility.
  • diethylene glycol ethyl methyl ether (boiling point 179 ° C.), 3-methoxy-3-methyl-1-butyl acetate (boiling point 188 ° C.), diethylene glycol ethyl methyl ether (boiling point 179 ° C.), 3 -Methoxybutyl acetate (boiling point 172 ° C.) and the like.
  • the content of the solvent having a boiling point of 150 ° C. or higher is preferably 40% by mass or less, more preferably 30% by mass or less in the total solvent. Moreover, 3 mass% or more is preferable, 5 mass% or more is more preferable, and 10 mass% or more is still more preferable. Within the above range, drying unevenness is unlikely to occur, and the drying time does not become too long and the productivity tends to be good.
  • the boiling point of the above “solvent having a boiling point of 150 ° C. or higher” is preferably 240 ° C. or lower, particularly preferably 200 ° C. or lower, from the viewpoint that the drying time does not become too long.
  • the solvent as described above is usually preferably in the range of 55% by mass to 95% by mass with respect to the total amount of the color material dispersion containing the solvent. It is preferably in the range of not less than mass% and not more than 90 mass%, more preferably in the range of not less than 70 mass% and not more than 88 mass%.
  • concentration will fall and it may be difficult to achieve to a target chromaticity coordinate.
  • dispersion auxiliary resin examples include alkali-soluble resins exemplified by a colored resin composition for a color filter described later.
  • the steric hindrance of the alkali-soluble resin makes it difficult for the colorant particles to come into contact with each other, and may have the effect of stabilizing the dispersion or reducing the dispersant due to the dispersion stabilizing effect.
  • Other components include, for example, surfactants for improving wettability, silane coupling agents for improving adhesion, antifoaming agents, repellency inhibitors, antioxidants, anti-aggregation agents, and UV absorbers. Etc.
  • the color material dispersion of the present invention is used as a preliminary preparation for preparing a colored resin composition for a color filter described later. That is, the color material dispersion is P / V (color material component mass in the composition) / (color material in the composition), which is preliminarily prepared in the previous stage of preparing the color resin composition for color filter described later. It is a colorant dispersion having a high ratio (solid content other than components). Specifically, the ratio of (mass of color material component in composition) / (mass of solid content other than color material component in composition) is usually 1.0 or more.
  • the method for producing the color material dispersion is not particularly limited as long as the color material is a method for obtaining a color material dispersion dispersed in a solvent with the dispersant. Especially, it is preferable to set it as either of the following two manufacturing methods from the point which is excellent in the dispersibility and dispersion stability of a coloring material.
  • the first method for producing a colorant dispersion according to the present invention includes a step of preparing the dispersant and a step of dispersing the colorant in the presence of the dispersant in a solvent. .
  • Two or more kinds of color materials may be co-dispersed in the presence of the dispersant in a solvent, or one or more kinds of color materials are dispersed or co-dispersed, and then two or more kinds of color material dispersions are mixed. By doing so, the colorant dispersion of the present invention may be obtained.
  • the second method for producing the colorant dispersion according to the present invention includes a solvent, the block copolymer, the organic acid compound, and halogenated carbonization. While mixing hydrogen and a coloring material, salt formation of at least a part of the terminal nitrogen moiety of the structural unit represented by the general formula (I) with the organic acid compound or the halogenated hydrocarbon is performed. And a step of dispersing the coloring material. Even when the color material is dispersed while forming such a salt, two or more kinds of color materials may be co-dispersed, or after one or more kinds of color materials are dispersed or co-dispersed, two or more kinds of colors are dispersed.
  • the color material dispersion of the present invention may be obtained by mixing the material dispersion.
  • the color material can be dispersed using a conventionally known disperser.
  • the dispersing machine include roll mills such as two rolls and three rolls, ball mills such as a ball mill and a vibration ball mill, bead mills such as a paint conditioner, a continuous disk type bead mill, and a continuous annular type bead mill.
  • the bead diameter to be used is preferably 0.03 mm or more and 3.0 mm or less, more preferably 0.05 or more and 2.0 mm or less.
  • the colored resin composition for a color filter according to the present invention is a colored resin composition for a color filter containing a coloring material, a dispersant, a binder component, and a solvent,
  • the color material includes a red color material and a yellow color material,
  • the yellow color material is at least one anion selected from the group consisting of mono-, di-, tri- and tetraanions of the azo compound represented by the general formula (A) and the azo compound having a tautomer structure thereof;
  • the dispersant is a polymer having a structural unit represented by the general formula (I).
  • the colored resin composition for a color filter of the present invention is excellent in color material dispersion stability like the color material dispersion of the present invention, and as described in the section of the color material dispersion of the present invention, the phase difference While the value is reduced, it is possible to form a colored layer having high luminance and high contrast and excellent color reproducibility.
  • the colored resin composition for a color filter of the present invention contains at least a colorant, a dispersant, a binder component, and a solvent, and further contains other components as long as the effects of the present invention are not impaired. You may do it.
  • the red color material that is an essential component among the color materials, the specific yellow color material, the dispersant, and the solvent are described above. Since it is the same as that described in the color material dispersion of the present invention, the description here is omitted.
  • the color material in the colored resin composition for a color filter of the present invention includes a red color material and the specific yellow color material as essential components, but in order to adjust the color tone, other color materials are used in combination. Also good. It is not particularly limited as long as it can form a desired color when forming the color layer of the color filter, and various organic pigments, inorganic pigments, dispersible dyes may be used alone or in combination of two or more. Can be used. Among these, organic pigments are preferably used because they have high color developability and high heat resistance. Examples of the organic pigment include compounds classified as pigments in the Color Index (CI; issued by The Society of Dyers and Colorists), specifically, the following color index (C.I. .) Can be listed with numbers.
  • CI Color Index
  • C.I. . color index
  • the dispersible dyes include dyes that are dispersible by imparting various substituents to the dyes or insolubilizing in a solvent by using a known lake (chlorination) technique, and low solubility. Examples thereof include dyes that can be dispersed by using in combination with a solvent. By using such a dispersible dye in combination with the dispersant, the dispersibility and dispersion stability of the dye can be improved.
  • the dispersible dye can be appropriately selected from conventionally known dyes.
  • dyes examples include azo dyes, metal complex salt azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes, cyanine dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, and phthalocyanine dyes.
  • azo dyes metal complex salt azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes, cyanine dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, and phthalocyanine dyes.
  • yellow color materials include C.I. I. Pigment Yellow 1, 3, 11, 12, 13, 14, 15, 16, 17, 20, 24, 31, 55, 60, 61, 65, 71, 73, 74, 81, 83, 93, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 116, 117, 119, 120, 126, 127, 128, 129, 138, 139, 150, 151, 152, 153, 154, 155, 156, 166, 167, 168, 175, 180, 185 and the like.
  • the content ratio of the red color material relative to the entire color material is not particularly limited as long as it is appropriately adjusted according to the desired chromaticity.
  • the red color material is contained in an amount of 35% by mass to 99% by mass with respect to the total amount of the color material from the viewpoint of increasing the color reproducibility and increasing the contrast while reducing the retardation value. More preferably, it is contained in an amount of not less than 98% by mass and not more than 98% by mass, and still more preferably not less than 45% by mass and not more than 97% by mass.
  • the total content of the yellow color material is 1% by mass or more and 65% by mass or less with respect to the total amount of the color material from the viewpoint of widening the color reproducibility and increasing the contrast while the retardation value is reduced. Is preferably 2% by mass or more and 60% by mass or less, more preferably 3% by mass or more and 55% by mass or less. Further preferred.
  • the colored resin composition for a color filter of the present invention comprises mono-, di-, tri- and tetraanions of the azo compound represented by the general formula (A) in the yellow color material and the azo compound having a tautomer structure thereof.
  • the total content of the compound represented by the formula (B) (the specific yellow color material) may be appropriately adjusted according to the desired chromaticity, and is not particularly limited.
  • the total content of the specific yellow color material is 10% by mass or more and 100% by mass with respect to the total amount of the yellow color material from the viewpoint of increasing the color reproducibility and increasing the contrast while the retardation value is reduced. Is preferably 15% by mass or more and 100% by mass or less, more preferably 20% by mass or more and 100% by mass or less, and further preferably 25% by mass or more and 100% by mass or less. Even more preferred.
  • the total content of the red color material and the yellow color material is preferably 60% by mass or more and 100% by mass or less and 70% by mass or more and 100% by mass or less with respect to the total color material. Is more preferable, and it is still more preferable that it is 80 to 100 mass%.
  • the colored resin composition for a color filter of the present invention contains a binder component in order to impart film formability and adhesion to the surface to be coated.
  • a curable binder component in order to impart film formability and adhesion to the surface to be coated.
  • the curable binder component used in forming the coloring layer of a conventionally well-known color filter can be used suitably.
  • the curable binder component include a photocurable binder component containing a photocurable resin that can be polymerized and cured by visible light, ultraviolet light, electron beam, and the like, and a thermosetting resin that can be polymerized and cured by heating. What contains the thermosetting binder component to contain can be used.
  • the photosensitive binder component which has alkali developability is used suitably.
  • the photosensitive binder component include a positive photosensitive binder component and a negative photosensitive binder component.
  • the positive photosensitive binder component include a system containing an alkali-soluble resin and an o-quinonediazide group-containing compound as a photosensitizing component.
  • the negative photosensitive binder component a system containing at least an alkali-soluble resin, a polyfunctional monomer, and a photoinitiator is preferably used.
  • a negative photosensitive binder component is preferable because a pattern can be easily formed by an existing process by a photolithography method.
  • the alkali-soluble resin, the polyfunctional monomer, and the photoinitiator constituting the negative photosensitive binder component will be specifically described.
  • the alkali-soluble resin in the present invention has an acidic group, and can be appropriately selected from those that act as a binder resin and are soluble in an alkali developer used for pattern formation.
  • the alkali-soluble resin can be based on an acid value of 40 mgKOH / g or more.
  • a preferred alkali-soluble resin in the present invention is a resin having an acidic group, usually a carboxy group, and specifically, acrylic resins such as an acrylic copolymer having a carboxy group and a styrene-acrylic copolymer having a carboxy group. And epoxy (meth) acrylate resins having a carboxy group.
  • acrylic resins such as acrylic copolymers and styrene-acrylic copolymers, and epoxy acrylate resins may be used in combination.
  • An acrylic resin such as an acrylic copolymer having a structural unit having a carboxyl group and a styrene-acrylic copolymer having a carboxyl group includes, for example, a carboxyl group-containing ethylenically unsaturated monomer and, if necessary, a copolymer. It is a (co) polymer obtained by (co) polymerizing other polymerizable monomers by a known method.
  • carboxyl group-containing ethylenically unsaturated monomer examples include (meth) acrylic acid, vinyl benzoic acid, maleic acid, maleic acid monoalkyl ester, fumaric acid, itaconic acid, crotonic acid, cinnamic acid, and acrylic acid dimer. It is done. Also, an addition reaction product of a monomer having a hydroxyl group such as 2-hydroxyethyl (meth) acrylate and a cyclic anhydride such as maleic anhydride, phthalic anhydride, or cyclohexanedicarboxylic anhydride, ⁇ -carboxy-polycaprolactone Mono (meth) acrylates can also be used.
  • anhydride containing monomers such as maleic anhydride, itaconic anhydride, and citraconic anhydride, as a precursor of a carboxyl group.
  • (meth) acrylic acid is particularly preferable from the viewpoints of copolymerizability, cost, solubility, glass transition temperature, and the like.
  • the alkali-soluble resin preferably further has a hydrocarbon ring from the viewpoint of excellent adhesion of the colored layer.
  • a hydrocarbon ring that is a bulky group in the alkali-soluble resin shrinkage during curing is suppressed, peeling from the substrate is eased, and substrate adhesion is improved.
  • the present inventors have found that the use of an alkali-soluble resin having a hydrocarbon ring suppresses the solvent resistance of the obtained colored layer, particularly the swelling of the colored layer. Although the action is unclear, the bulky hydrocarbon ring in the colored layer suppresses the movement of molecules in the colored layer, resulting in an increase in the strength of the coating and suppression of swelling by the solvent. It is estimated that.
  • hydrocarbon rings examples include aliphatic hydrocarbon rings that may have a substituent, aromatic hydrocarbon rings that may have a substituent, and combinations thereof. May have a substituent such as an alkyl group, a carbonyl group, a carboxyl group, an oxycarbonyl group, an amide group, a hydroxyl group, a nitro group, an amino group, or a halogen atom.
  • the hydrocarbon ring may be contained as a monovalent group or a divalent or higher group.
  • hydrocarbon ring examples include aliphatic hydrocarbons such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, norbornane, tricyclo [5.2.1.0 (2,6)] decane (dicyclopentane), and adamantane.
  • Ring aromatic hydrocarbon ring such as benzene, naphthalene, anthracene, phenanthrene, fluorene, etc .; chain polycycle such as biphenyl, terphenyl, diphenylmethane, triphenylmethane, stilbene, cardo structure (9,9-diarylfluorene), etc. Is mentioned.
  • the hydrocarbon ring When an aliphatic hydrocarbon ring is included as the hydrocarbon ring, it is preferable from the viewpoint of improving the heat resistance and adhesion of the colored layer and improving the luminance of the obtained colored layer. Moreover, when the said cardo structure is included, the sclerosis
  • the alkali-soluble resin preferably has a bridged cyclic hydrocarbon ring, which is an aliphatic hydrocarbon ring having a structure in which two or more rings share two or more atoms.
  • Specific examples of the bridged cyclic hydrocarbon ring include norbornane, isobornane, adamantane, tricyclo [5.2.1.0 (2,6)] decane, tricyclo [5.2.1.0 (2,6)].
  • Decene, tricyclopentene, tricyclopentane, tricyclopentadiene, dicyclopentadiene; groups in which a part of these groups are substituted with a substituent are mentioned.
  • substituents examples include an alkyl group, a cycloalkyl group, an alkylcycloalkyl group, a hydroxyl group, a carbonyl group, a nitro group, an amino group, and a halogen atom.
  • the lower limit of the number of carbon atoms in the crosslinked cyclic hydrocarbon ring is preferably 5 or more, and particularly preferably 7 or more, from the viewpoint of compatibility with other materials and solubility in an alkali developer.
  • the upper limit is preferably 12 or less, and particularly preferably 10 or less.
  • the alkali-soluble resin preferably has a maleimide structure represented by the following general formula (III).
  • R M represents an optionally substituted hydrocarbon ring.
  • the alkali-soluble resin has a maleimide structure represented by the general formula (III), it has a nitrogen atom in the hydrocarbon ring, and therefore is a basic polymer that has a structural unit represented by the general formula (I).
  • the compatibility with the dispersant is very good, the development speed is high, and the effect of suppressing development residue is improved.
  • R M of the general formula (III) specific examples of the optionally substituted hydrocarbon ring, those similar to the specific example of the hydrocarbon ring.
  • an aliphatic hydrocarbon ring such as cyclopentyl group, cyclohexyl group, cyclooctyl group, phenyl group, methylphenyl group, ethylphenyl group, dimethylphenyl group, diethylphenyl group, methoxyphenyl group, benzyl group, hydroxyphenyl group
  • An aromatic hydrocarbon ring such as a naphthyl group, and a group in which a part of these groups is substituted with a substituent are exemplified.
  • the alkali-soluble resin used in the present invention it is easy to adjust the amount of each constituent unit by using an acrylic copolymer having a constituent unit having a hydrocarbon ring separately from the constituent unit having a carboxy group. This is preferable because the amount of the structural unit having a hydrocarbon ring is increased to easily improve the function of the structural unit.
  • the acrylic copolymer having a structural unit having a carboxy group and the hydrocarbon ring is prepared by using an ethylenically unsaturated monomer having a hydrocarbon ring as the above-mentioned “other monomer capable of copolymerization”. be able to.
  • Examples of the ethylenically unsaturated monomer having a hydrocarbon ring include cyclohexyl (meth) acrylate, dicyclopentanyl (meth) acrylate, adamantyl (meth) acrylate, isobornyl (meth) acrylate, benzyl (meth) acrylate, and phenoxyethyl. (Meth) acrylate, styrene, etc. are mentioned.
  • cyclohexyl (meth) acrylate dicyclopentanyl (meth) acrylate, adamantyl
  • the alkali-soluble resin used in the present invention preferably has an ethylenic double bond in the side chain.
  • the alkali-soluble resins, or the alkali-soluble resin and the polyfunctional monomer can form a cross-linked bond in the curing step of the resin composition at the time of producing the color filter.
  • the film strength of the cured film is further improved and the development resistance is improved, and the thermal contraction of the cured film is suppressed and the adhesiveness with the substrate is excellent.
  • the method for introducing an ethylenic double bond into the alkali-soluble resin may be appropriately selected from conventionally known methods.
  • a method of introducing an ethylenic double bond into a side chain by adding a compound having both an epoxy group and an ethylenic double bond in the molecule, such as glycidyl (meth) acrylate, to the carboxyl group of the alkali-soluble resin Or by introducing a structural unit having a hydroxyl group into a copolymer, adding a compound having an isocyanate group and an ethylenic double bond in the molecule, and introducing an ethylenic double bond into the side chain.
  • a compound having both an epoxy group and an ethylenic double bond in the molecule such as glycidyl (meth) acrylate
  • the alkali-soluble resin of the present invention may further contain other structural units such as a structural unit having an ester group such as methyl (meth) acrylate and ethyl (meth) acrylate.
  • the structural unit having an ester group not only functions as a component that suppresses alkali solubility of the colored resin composition for a color filter, but also functions as a component that improves the solubility in a solvent and further the solvent resolubility.
  • the alkali-soluble resin in the present invention is preferably an acrylic resin such as an acrylic copolymer and a styrene-acrylic copolymer having a structural unit having a carboxyl group and a structural unit having a hydrocarbon ring, It is an acrylic resin such as an acrylic copolymer and a styrene-acrylic copolymer having a structural unit having a carboxyl group, a structural unit having a hydrocarbon ring, and a structural unit having an ethylenic double bond. Is more preferable.
  • the alkali-soluble resin can be made into an alkali-soluble resin having desired performance by appropriately adjusting the charged amount of each structural unit.
  • the charged amount of the carboxyl group-containing ethylenically unsaturated monomer is preferably 5% by mass or more and more preferably 10% by mass or more with respect to the total amount of the monomer from the viewpoint of obtaining a good pattern.
  • the amount of the carboxyl group-containing ethylenically unsaturated monomer is preferably 50% by mass or less, and 40% by mass or less with respect to the total amount of monomers. More preferably.
  • the coating film obtained has sufficient solubility in an alkaline developer, and the proportion of the carboxyl group-containing ethylenically unsaturated monomer is the upper limit.
  • the proportion of the carboxyl group-containing ethylenically unsaturated monomer is the upper limit.
  • an acrylic resin such as an acrylic copolymer having a structural unit having an ethylenic double bond and a styrene-acrylic copolymer, which is more preferably used as an alkali-soluble resin
  • an epoxy group and an ethylenic double bond are used.
  • the amount of the compound having a bond is preferably 10% by mass or more and 95% by mass or less, and more preferably 15% by mass or more and 90% by mass or less with respect to the charged amount of the carboxyl group-containing ethylenically unsaturated monomer.
  • the preferred weight average molecular weight (Mw) of the carboxy group-containing copolymer is preferably in the range of 1,000 to 50,000, more preferably 3,000 to 20,000. If it is less than 1,000, the binder function after curing may be remarkably lowered. If it exceeds 50,000, pattern formation may be difficult during development with an alkali developer.
  • the weight average molecular weight (Mw) of the carboxy group-containing copolymer can be measured by a Shodex GPC System-21H using polystyrene as a standard substance and THF as an eluent.
  • Epoxy (meth) acrylate resin which has a carboxy group Epoxy (meth) obtained by making the reaction product of an epoxy compound and unsaturated group containing monocarboxylic acid react with an acid anhydride. Acrylate compounds are suitable.
  • the epoxy compound, unsaturated group-containing monocarboxylic acid, and acid anhydride can be appropriately selected from known ones.
  • the epoxy (meth) acrylate resin having a carboxy group may be used alone or in combination of two or more.
  • the alkali-soluble resin is preferably selected from those having an acid value of 50 mgKOH / g or more from the viewpoint of developability (solubility) with respect to an alkaline aqueous solution used for the developer.
  • the alkali-soluble resin preferably has an acid value of 70 mgKOH / g or more and 300 mgKOH / g or less from the viewpoint of developability (solubility) with respect to an aqueous alkali solution used for the developer and adhesion to the substrate. It is preferable that it is 80 mgKOH / g or more and 280 mgKOH / g or less.
  • the acid value can be measured according to JIS K 0070.
  • the ethylenically unsaturated bond equivalent in the case where the side chain of the alkali-soluble resin has an ethylenically unsaturated group improves the film strength of the cured film, improves the development resistance, and obtains the effect of excellent adhesion to the substrate. From the viewpoint, it is preferably in the range of 100 to 2000, and particularly preferably in the range of 140 to 1500. When the ethylenically unsaturated bond equivalent is 2000 or less, the development resistance and adhesion are excellent. Moreover, since the ratio of other structural units, such as the structural unit which has the said carboxy group, and the structural unit which has a hydrocarbon ring, can be relatively increased if it is 100 or more, it is excellent in developability and heat resistance. Yes.
  • the ethylenically unsaturated bond equivalent is a weight average molecular weight per mole of the ethylenically unsaturated bond in the alkali-soluble resin, and is represented by the following formula (1).
  • Ethylenically unsaturated bond equivalent (g / mol) W (g) / M (mol) (In Formula (1), W represents the mass (g) of the alkali-soluble resin, and M represents the number of moles (mol) of the ethylenic double bond contained in the alkali-soluble resin W (g).)
  • the ethylenically unsaturated bond equivalent is determined, for example, by measuring the number of ethylenic double bonds contained in 1 g of the alkali-soluble resin in accordance with the test method for the iodine value described in JIS K 0070: 1992. It may be calculated.
  • the alkali-soluble resin used in the colored resin composition for color filters may be used alone or in combination of two or more, and the content is not particularly limited, but for color filters.
  • the alkali-soluble resin is preferably 5% by mass or more and 60% by mass or less, more preferably 10% by mass or more and 40% by mass or less, based on the total solid content of the colored resin composition.
  • the content of the alkali-soluble resin is not less than the above lower limit, sufficient alkali developability can be easily obtained, and when the content of the alkali-soluble resin is not more than the above upper limit, film roughness or lack of pattern can be caused during development. It is easy to suppress.
  • the polyfunctional monomer used in the colored resin composition for a color filter is not particularly limited as long as it can be polymerized by the photoinitiator, and a compound having two or more ethylenically unsaturated double bonds is usually used.
  • a polyfunctional (meth) acrylate is preferably used, and particularly has two or more acryloyl groups or methacryloyl groups.
  • Such polyfunctional (meth) acrylate may be appropriately selected from conventionally known ones. Specific examples include those described in JP2013-029832A.
  • polyfunctional (meth) acrylates may be used alone or in combination of two or more. Moreover, when the photocurability (high sensitivity) is requested
  • a polyfunctional monomer is 5 mass% or more and 60 with respect to the solid content whole quantity of the colored resin composition for color filters. It is within the range of 10% by mass or less and more preferably 40% by mass or less.
  • the content of the polyfunctional monomer is not less than the above lower limit, photocuring proceeds sufficiently, and the exposed portion can suppress elution during development, and when the content of the polyfunctional monomer is not more than the above upper limit, alkali development Sex is enough.
  • Photoinitiator There is no restriction
  • the initiator include aromatic ketones such as benzophenone, 4,4′-bisdiethylaminobenzophenone and 4-methoxy-4′-dimethylaminobenzophenone, benzoin ethers such as benzoin methyl ether, and benzoin such as ethylbenzoin.
  • Biimidazoles such as 2- (o-chlorophenyl) -4,5-phenylimidazole dimer, halo such as 2-trichloromethyl-5- (p-methoxystyryl) -1,3,4-oxadiazole Methyloxadiazole compounds, halomethyl-S-triazine compounds such as 2- (4-butoxy-naphth-1-yl) -4,6-bis-trichloromethyl-S-triazine, 2,2-dimethoxy-1, 2-diphenylethane-1-one, 2-methyl-1- [4- (methylthio) phenyl] -2 Morpholinopropanone, 1,2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1,1-hydroxy-cyclohexyl-phenyl ketone, benzyl, benzoylbenzoic acid, methyl benzoylbenzoate, 4 -Benzoyl
  • 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2-benzyl-2- (dimethylamino) -1- (4-morpholinophenyl) -1- Butanone, 4,4′-bis (diethylamino) benzophenone, and diethylthioxanthone are preferably used.
  • a sensitivity is obtained by combining an ⁇ -aminoacetophenone initiator such as 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one with a thioxanthone initiator such as diethylthioxanthone.
  • the total content of ⁇ -aminoacetophenone initiator and thioxanthone initiator is preferably 5% by mass or more and 15% by mass or less based on the total solid content of the colored resin composition.
  • the amount of the initiator is 15% by mass or less, sublimates during the production process are reduced, which is preferable.
  • the amount of the initiator is 5% by mass or more, development resistance such as water stain is improved.
  • the initiator preferably contains an oxime ester photoinitiator from the viewpoint of improving sensitivity.
  • an oxime ester photoinitiator By using an oxime ester photoinitiator, in-plane line width variations are easily suppressed when forming a fine line pattern. Furthermore, by using an oxime ester photoinitiator, the development resistance is improved, and the effect of suppressing the occurrence of water stain tends to be increased.
  • water stain means that, when a component that enhances alkali developability is used, a trace of water stain is generated after rinsing with pure water after alkali development. Such a water stain disappears after post-baking, so there is no problem as a product. Arise.
  • the inspection sensitivity of the inspection apparatus is lowered in the appearance inspection, the yield of the final color filter product is lowered as a result, which becomes a problem.
  • the oxime ester-based photoinitiator those having an aromatic ring are preferable from the viewpoint of reducing contamination of the colored resin composition for color filters and degradation of the apparatus due to decomposition products, and having condensed rings including aromatic rings. More preferred are those having a condensed ring containing a benzene ring and a heterocycle.
  • oxime ester photoinitiators examples include 1,2-octadion-1- [4- (phenylthio)-, 2- (o-benzoyloxime)], ethanone, 1- [9-ethyl-6- (2-methyl) Benzoyl) -9H-carbazol-3-yl]-, 1- (o-acetyloxime), JP 2000-80068 A, JP 2001-233842 A, Special Table 2010-527339, Special Table 2010-527338, It can be appropriately selected from oxime ester photoinitiators described in JP2013-041153A.
  • Irgacure OXE-02 having a carbazole skeleton (manufactured by BASF), Adeka Arcles NCI-831 (manufactured by ADEKA), TR-PBG-304 (manufactured by Changzhou Power Electronics Co., Ltd.), ADEKA having a diphenyl sulfide skeleton ARKULS NCI-930 (manufactured by ADEKA), TR-PBG-345, TR-PBG-3057 (manufactured by Changzhou Power Electronics New Materials), Irgacure OXE-01 (manufactured by BASF), TR-PBG- having a fluorene skeleton 365 (manufactured by Changzhou Power Electronics New Materials Co., Ltd.) or the like may be used.
  • an oxime ester photoinitiator having a diphenyl sulfide skeleton or a fluorene skeleton from the viewpoint of luminance. It is preferable to use an oxime ester photoinitiator having a carbazole skeleton from the viewpoint of high sensitivity. Further, it is preferable to use two or more kinds of oxime ester photoinitiators in terms of easily improving luminance and development resistance and having a high effect of suppressing water stain generation.
  • the combined use of two types of oxime ester photoinitiators having a diphenyl sulfide skeleton, or the combined use of an oxime ester photoinitiator having a diphenyl sulfide skeleton and an oxime ester photoinitiator having a fluorene skeleton is high in luminance and heat resistance. It is preferable from the point of high property.
  • an oxime ester-based photoinitiator having a carbazole skeleton and an oxime ester-based photoinitiator having a fluorene skeleton or an oxime ester-based photoinitiator having a diphenyl sulfide is excellent in sensitivity and water stain generation suppression effect. Is preferable.
  • a photoinitiator having a tertiary amine structure in combination with an oxime ester photoinitiator from the viewpoint of suppressing water stain and improving sensitivity. Since the photoinitiator having a tertiary amine structure has a tertiary amine structure that is an oxygen quencher in the molecule, radicals generated from the initiator are hardly deactivated by oxygen, and sensitivity can be improved. is there.
  • Examples of commercially available photoinitiators having the tertiary amine structure include 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one (for example, Irgacure 907, manufactured by BASF), 2-benzyl-2- (dimethylamino) -1- (4-morpholinophenyl) -1-butanone (eg Irgacure 369, manufactured by BASF), 4,4′-bis (diethylamino) benzophenone (eg Hycure ABP, Kawaguchi Pharmaceutical).
  • 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one for example, Irgacure 907, manufactured by BASF
  • 2-benzyl-2- (dimethylamino) -1- (4-morpholinophenyl) -1-butanone eg Irgacure 369, manufactured by BASF
  • combining an oxime ester photoinitiator with a thioxanthone initiator is preferable from the viewpoint of adjusting sensitivity, suppressing water stain, and improving development resistance.
  • Two or more oxime ester photoinitiators and a thioxanthone photoinitiator are preferable.
  • a combination of initiators is preferable in that brightness and development resistance are improved, sensitivity adjustment is easy, water stain generation suppression effect is high, and development resistance is improved.
  • the content of the photoinitiator used in the colored resin composition for a color filter of the present invention is usually about 0.01 parts by mass or more and 100 parts by mass or less, preferably 5 parts by mass with respect to 100 parts by mass of the polyfunctional monomer.
  • the amount is 60 parts by mass or less. If this content is not less than the above lower limit, the photocuring is sufficiently advanced and the exposed portion is prevented from being eluted during development, while if it is not more than the above upper limit, the yellowing of the resulting colored layer is weakened and the luminance is reduced. It can suppress that it falls.
  • the total content of two or more oxime ester photoinitiators is based on the total solid content of the colored resin composition for color filters. 0.1% by mass or more and 12.0% by mass or less, more preferably 1.0% by mass or more and 8.0% by mass or less in the range of sufficiently exhibiting the combined effect of these photoinitiators. To preferred.
  • the binder component used in the colored resin composition for a color filter of the present invention preferably has a total content of 35% by mass to 97% by mass with respect to the total solid content of the colored resin composition for a color filter. It is more preferable to blend in a proportion of not less than mass% and not more than 96 mass%. If it is more than the said lower limit, the colored layer excellent in hardness and the adhesiveness with a board
  • the colored resin composition for a color filter may contain various additives as necessary.
  • additives include, in addition to antioxidants, mercapto compounds, polymerization terminators, chain transfer agents, leveling agents, plasticizers, surfactants, antifoaming agents, silane coupling agents, ultraviolet absorbers, adhesion promoters. Etc.
  • the colored resin composition for a color filter of the present invention further contains an antioxidant because heat resistance is improved, fading of the coloring material is suppressed, and luminance is improved.
  • the colored resin composition for color filters of the present invention further contains an antioxidant from the viewpoint of improving the adhesion of the SiN substrate.
  • the antioxidant may be appropriately selected from conventionally known antioxidants. Specific examples of antioxidants include, for example, hindered phenol antioxidants, amine antioxidants, phosphorus antioxidants, sulfur antioxidants, hydrazine antioxidants, and the like. From the viewpoint, it is preferable to use a hindered phenol-based antioxidant.
  • the hindered phenol antioxidant contains at least one phenol structure, and has a structure in which a substituent having 4 or more carbon atoms is substituted on at least one of the 2-position and 6-position of the hydroxyl group of the phenol structure. Means an antioxidant.
  • hindered phenol antioxidant examples include, for example, dibutylhydroxytoluene (BHT), pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] (trade name: Irganox 1010, manufactured by BASF), 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate (trade name: Irganox 3114, manufactured by BASF), 2,4,6 Tris (4-hydroxy-3,5-di-tert-butylbenzyl) mesitylene (trade name: Irganox 1330, manufactured by BASF), 6- (4-hydroxy-3,5-di-tert-butylanilino) -2 , 4-Bis (octylthio) -1,3,5-triazine (trade name: Irganox 565) BASF), 2,2′-thiodiethylbis [
  • oligomer-type and polymer-type compounds having a hindered phenol structure can also be used.
  • pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] (trade name: trade name: IRGANOX1010, manufactured by BASF) is preferable from the viewpoint of heat resistance and light resistance.
  • a hindered phenol antioxidant having a molecular weight of 1000 or less and a molecular weight per phenolic hydroxyl group of 280 equivalents or less, and further a molecular weight of 500 or less and a molecular weight per phenolic hydroxyl group of 200 equivalents or less.
  • Such an antioxidant has high fluidity and many active points per weight, so that radical trapping suppresses color material aggregation due to rapid curing shrinkage during exposure and post-baking, It is presumed that the above effect is easily obtained due to suppression of yellowing.
  • examples of such an antioxidant include 6,6′-di-tert-butyl-4,4′-butylidene di-m-cresol (trade name: ADK STAB AO-40, manufactured by ADEKA).
  • the latent antioxidant is a compound having a protecting group that can be removed by heating, and exhibiting an antioxidant function when the protecting group is eliminated. Among them, those which are easy to remove the protecting group by heating at 150 ° C. or higher are preferable.
  • the latent antioxidant as described in international publication 2014/021023 is mentioned.
  • latent antioxidants examples include latent hindered phenol antioxidants in which the phenolic hydroxyl group of the hindered phenol antioxidant is protected with a protecting group that can be removed by heating.
  • latent hindered phenolic antioxidants phenolic hydroxyl groups of hindered phenolic antioxidants, acid anhydrides, acid chlorides, Boc reagents, alkyl halide compounds, silyl chloride compounds, allyl ether compounds, etc. And the reaction product.
  • a structure in which the hydrogen of the phenol group of the hindered phenol antioxidant is substituted with a carbamate protecting group such as a t-butoxycarbonyl group is preferably used. Examples include, but are not limited to, the following chemical formulas (a) to (c).
  • the method for producing the latent antioxidant is not particularly limited.
  • the colored resin composition for a color filter of the present invention is preferably used as a colored resin composition in combination with the oxime ester photoinitiator and an antioxidant from the viewpoint of improving luminance by a synergistic effect.
  • antioxidant is 0.05 mass part or more and 10.00 mass part or less with respect to 100 mass parts of total solids in a colored resin composition, 0.10 More preferably, it is at least part by mass and no more than 5.00 parts by mass. If it is more than the said lower limit, it is excellent in heat resistance and light resistance. On the other hand, if it is below the said upper limit, the colored resin composition of this invention can be made into a highly sensitive photosensitive resin composition.
  • the content of the antioxidant is 1 part by mass of the antioxidant with respect to 100 parts by mass of the total amount of the oxime ester photoinitiator. It is preferably 250 parts by mass or less, more preferably 3 parts by mass or more and 80 parts by mass or less, and still more preferably 5 parts by mass or more and 45 parts by mass or less. If it is in the said range, it is excellent in the effect of the said combination.
  • the colored resin composition for a color filter of the present invention further contains a mercapto compound from the viewpoint of improving the effect of suppressing the occurrence of water stain.
  • the colored resin composition for a color filter of the present invention contains a combination of the oxime ester photoinitiator and a mercapto compound as a photosensitive colored resin composition, which improves development resistance and generates water stains. This is preferable because the suppression effect is further improved, and when forming a fine line pattern, the linearity is further improved, and the ability to form a fine line pattern as designed for the mask line width is improved.
  • “Improved linearity” means that the end of the colored layer formed in the development step after applying the colored composition has few irregularities and is linear or substantially linear.
  • the mercapto compound can function as a chain transfer agent, and has the property of receiving radicals from slowly reacting radicals to accelerate the reaction and improve curability.
  • Examples of mercapto compounds include 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2-mercaptobenzimidazole, 2-mercapto-5-methoxybenzothiazole, 2-mercapto-5-methoxybenzimidazole, and 3-mercaptopropionic acid.
  • the mercapto compound one or a combination of two or more may be used. Among them, one or more selected from the group consisting of polyfunctional mercapto compounds having two or more mercapto groups in one molecule may be used. It is preferable from the viewpoint that the crosslink density is increased and the effect of suppressing water stain is improved.
  • a secondary mercapto compound having a secondary mercapto group in which the carbon atom to which the mercapto group is bonded is a secondary carbon atom is preferable from the viewpoint that even when stored for a long period of time, a good water stain suppression effect is easily maintained. Further, a polyfunctional secondary mercapto compound having two or more secondary mercapto groups in one molecule is more preferable.
  • the content of the mercapto compound used in the colored resin composition for color filter is not particularly limited, but the mercapto compound is 0.2% by mass or more and 7% by mass with respect to the total solid content of the colored resin composition for color filter. % Or less, and more preferably in the range of 0.5% by mass or more and 5% by mass or less from the viewpoint of sufficiently exhibiting the above effects.
  • the colored resin composition for a color filter of the present invention further contains an ultraviolet absorber from the viewpoint that a colored layer with improved contrast can be formed while the retardation value is reduced.
  • an ultraviolet absorber suitably from a conventionally well-known thing.
  • Specific examples of the ultraviolet absorber include benzotriazole compounds, benzophenone compounds, triazine compounds, and the like. Among them, it is preferable to use a benzotriazole-based compound from the viewpoint that a colored layer with improved contrast can be formed while the retardation value is reduced.
  • benzotriazole compounds examples include 2- (5-methyl-2-hydroxyphenyl) benzotriazole, 2- (2-hydroxy-5-tert-butylphenyl) -2H-benzotriazole, octyl-3 [3- t-Butyl-4-hydroxy-5- (5-chloro-2H-benzotriazol-2-yl) phenyl] propionate and 2-ethylhexyl-3- [3-t-butyl-4-hydroxy-5- (5- Chloro-2H-benzotriazol-2-yl) phenyl] propionate, 2- [2-hydroxy-3,5-bis ( ⁇ , ⁇ -dimethylbenzyl) phenyl] -2H-benzotriazole, 2- (3- t-butyl-5-methyl-2-hydroxyphenyl) -5-chlorobenzotriazole, 2- (3,5-di-t-amyl-2- Droxyphenyl) benzotriazole, 2- (2′-hydroxy-5′-
  • Examples of commercially available products include “TINUVIN P”, “TINUVIN PS”, “TINUVIN 109”, “TINUVIN 234”, “TINUVIN 326”, “TINUVIN 328”, “TINUVIN 329”, and “TINUVIN 384-2” manufactured by BASF. ”,“ TINUVIN 900 ”,“ TINUVIN 928 ”,“ TINUVIN 99-2 ”,“ TINUVIN 1130 ”, and the like.
  • a benzotriazole-based compound represented by the following general formula (IV) is preferable because a colored layer with improved contrast can be formed while the retardation value is reduced.
  • R 11 and R 12 are each independently an alkyl group having 1 to 20 carbon atoms which may be substituted with a hydrogen atom or a phenyl group, and X represents a hydrogen atom or a chlorine atom. .
  • R 12 is preferably a methyl group, a t-butyl group, a t-amyl group, a t-octyl group, or an ⁇ , ⁇ -dimethylbenzyl group
  • R 11 is a hydrogen atom
  • An atom, a t-butyl group, a t-amyl group, or an ⁇ , ⁇ -dimethylbenzyl group is preferable.
  • an ultraviolet absorber is 0.05 mass part or more with respect to 100 mass parts of total solids in a colored resin composition. It is preferably 10.00 parts by mass or less, and more preferably 0.10 parts by mass or more and 5.00 parts by mass or less. If it is more than the said lower limit, it is excellent in heat resistance and light resistance. On the other hand, if it is below the said upper limit, the colored resin composition of this invention can be made into a highly sensitive photosensitive resin composition.
  • the colored resin composition for a color filter of the present invention is preferably used as a colored resin composition in combination with the oxime ester photoinitiator and an ultraviolet absorber from the viewpoint of improving luminance by a synergistic effect.
  • the content of the ultraviolet absorber is 1 part by mass with respect to 100 parts by mass of the total amount of the oxime ester photoinitiator.
  • the amount is preferably 250 parts by mass or less, more preferably 3 parts by mass or more and 80 parts by mass or less, and still more preferably 5 parts by mass or more and 45 parts by mass or less. If it is in the said range, it is excellent in the effect of the said combination.
  • surfactant and the plasticizer include those described in JP 2013-029832 A, for example.
  • silane coupling agents examples include KBM-502, KBM-503, KBE-502, KBE-503, KBM-5103, KBM-903, KBE-903, KBM573, KBM-403, KBE-402, KBE-403. KBM-303, KBM-802, KBM-803, KBE-9007, X-12-967C (manufactured by Shin-Etsu Silicone), and the like. Of these, KBM-502, KBM-503, KBE-502, KBE-503, and KBM-5103 having a methacrylic group and an acrylic group are preferable from the viewpoint of adhesion of the SiN substrate.
  • the content of the silane coupling agent is preferably 0.05 parts by mass or more and 10.0 parts by mass or less with respect to 100 parts by mass of the total solid content in the colored resin composition. More preferably, it is 1 part by mass or more and 5.0 parts by mass or less. If it is more than the said lower limit and below the said upper limit, it is excellent in the adhesiveness of SiN.
  • the total content of the color material is 3% by mass or more and 65% by mass or less, more preferably 4% by mass or more and 60% by mass or less, based on the total solid content of the colored resin composition for color filters. Is preferred. If it is more than the said lower limit, the colored layer at the time of apply
  • the content of the color material is 15% by mass or more and 65% by mass or less, more preferably 25% by mass with respect to the total solid content of the color resin composition for color filters. It is preferable to mix
  • the content of the dispersant is not particularly limited as long as it can uniformly disperse the coloring material.
  • the content of the dispersant is 1 with respect to the total solid content of the colored resin composition for a color filter. It can be used in the range of mass% to 40 mass%.
  • blend in the ratio of 2 mass% or more and 30 mass% or less with respect to solid content whole quantity of the colored resin composition for color filters, and it is preferable to mix
  • the content of the dispersing agent is 2% by mass or more and 25% by mass or less, more preferably 3%, based on the total solid content of the colored resin composition for color filters. It is preferable to mix in a proportion of not less than 20% by mass and not more than 20% by mass. Moreover, what is necessary is just to set content of a solvent suitably in the range which can form a colored layer accurately. Usually, it is preferably in the range of 55% by mass to 95% by mass with respect to the total amount of the colored resin composition for a color filter containing the solvent, and in particular, in the range of 65% by mass to 88% by mass. More preferably. When the content of the solvent is within the above range, the coating property can be excellent.
  • the P / V ratio ((color material component mass in the composition) / (solid content mass other than color material components in the composition) ratio) is degassed or From the viewpoint of heat shrinkage, it is preferably 0.1 or more, and more preferably 0.2 or more. On the other hand, it is excellent in suppression of retardation and manufacturing convenience, that is, solvent resolubility, development. From the viewpoint of excellent residue, development adhesion, development resistance, water stain occurrence suppression effect, etc., it is preferably 0.8 or less, more preferably 0.7 or less, from the point of development residue, development adhesion It is still more preferable that it is 0.6 or less.
  • the film thickness of the cured film is a film after applying the colored resin composition for color filter, drying, exposing to cure the polyfunctional monomer, and then post-baking in a clean oven at 230 ° C. for 30 minutes. Thickness.
  • the red colorant is 45.0% by mass or more and 98% of the total colorant.
  • the specific yellow color material is preferably 2.0 mass% or more and 55.0 mass% or less, and the red color material is 50.0 mass% or more and 95.0 mass% or less,
  • the specific yellow color material is preferably 5.0% by mass or more and 50.0% by mass or less, and in particular, the red color material is 55.0% by mass or more and 90.0% by mass or less, and the specific yellow color material. Is preferably 10.0% by mass or more and 45.0% by mass or less.
  • the method for producing the colored resin composition for a color filter of the present invention is not particularly limited.
  • the color material dispersion of the present invention includes an alkali-soluble resin, a polyfunctional monomer, a photoinitiator, and as necessary. It can be obtained by adding other components and mixing them using a known mixing means.
  • each color material dispersion liquid is prepared, and each color material dispersion liquid, a binder component, and other components as necessary, using a known mixing means. It can be obtained by mixing.
  • the color filter according to the present invention is a color filter comprising at least a substrate and a colored layer provided on the substrate, and at least one of the colored layers is a colored resin composition for a color filter according to the present invention. It has a colored layer which is a cured product.
  • FIG. 1 is a schematic sectional view showing an example of the color filter of the present invention.
  • the color filter 10 of the present invention has a substrate 1, a light shielding part 2, and a colored layer 3.
  • At least one of the colored layers used in the color filter of the present invention is a cured product of the colored resin composition for a color filter according to the present invention, that is, a colored layer formed by curing the colored resin composition.
  • the colored layer is usually formed in an opening of a light-shielding part on the substrate to be described later, and is usually composed of a colored pattern of three or more colors.
  • the arrangement of the colored layers is not particularly limited, and for example, a general arrangement such as a stripe type, a mosaic type, a triangle type, or a four-pixel arrangement type can be used.
  • variety, area, etc. of a colored layer can be set arbitrarily.
  • the thickness of the colored layer is appropriately controlled by adjusting the coating method, the solid content concentration, the viscosity, and the like of the colored resin composition for a color filter, but is usually preferably in the range of 1 ⁇ m to 5 ⁇ m.
  • the colored layer can be formed by the following method, for example.
  • a coating means such as a spray coating method, a dip coating method, a bar coating method, a roll coating method, a spin coating method, or a die coating method. Apply to form a wet coating.
  • spin coating and die coating can be preferably used.
  • Examples of the light source used for exposure include ultraviolet rays such as a low-pressure mercury lamp, a high-pressure mercury lamp, and a metal halide lamp, and an electron beam.
  • the exposure amount is appropriately adjusted depending on the light source used, the thickness of the coating film, and the like.
  • the heating conditions are appropriately selected depending on the blending ratio of each component in the colored resin composition for the color filter to be used, the thickness of the coating film, and the like.
  • a coating film is formed with a desired pattern by melt
  • a solution in which an alkali is dissolved in water or a water-soluble solvent is usually used.
  • An appropriate amount of a surfactant or the like may be added to the alkaline solution.
  • a general method can be adopted as the developing method.
  • the developer is usually washed and the cured coating film of the colored resin composition for color filters is dried to form a colored layer.
  • the heating conditions are not particularly limited and are appropriately selected depending on the application of the coating film.
  • the light shielding part in the color filter of the present invention is formed in a pattern on a substrate to be described later, and can be the same as that used as a light shielding part in a general color filter.
  • the pattern shape of the light shielding portion is not particularly limited, and examples thereof include a stripe shape and a matrix shape.
  • the light shielding part may be a metal thin film such as chromium by sputtering, vacuum deposition or the like.
  • the light shielding part may be a resin layer in which light shielding particles such as carbon fine particles, metal oxides, inorganic pigments, and organic pigments are contained in a resin binder.
  • the thickness of the light-shielding part is set to about 0.2 ⁇ m to 0.4 ⁇ m in the case of a metal thin film, and about 0.5 ⁇ m to 2 ⁇ m in the case where a black pigment is dispersed or dissolved in a binder resin. Set by.
  • substrate As the substrate, a transparent substrate or a silicon substrate, which will be described later, or an aluminum, silver, or silver / copper / palladium alloy thin film formed on the substrate is used. On these substrates, another color filter layer, a resin layer, a transistor such as a TFT, a circuit, or the like may be formed.
  • the transparent substrate in the color filter of the present invention is not particularly limited as long as it is a base material transparent to visible light, and a transparent substrate used for a general color filter can be used.
  • transparent flexible rigid materials such as quartz glass, alkali-free glass, and synthetic quartz plates, or transparent flexible flexible materials such as transparent resin films, optical resin plates, and flexible glasses. Materials.
  • the thickness of the said transparent substrate is not specifically limited, According to the use of the color filter of this invention, the thing about 100 micrometers or more and 1 mm or less can be used, for example.
  • the color filter of the present invention includes, for example, an overcoat layer, a transparent electrode layer, an alignment film, an alignment protrusion, a columnar spacer, etc., in addition to the substrate, the light shielding portion, and the colored layer. Also good.
  • the display device includes the color filter according to the present invention.
  • the configuration of the display device is not particularly limited, and can be appropriately selected from conventionally known display devices, such as a liquid crystal display device and an organic light emitting display device.
  • display defects such as a liquid crystal orientation disorder caused by the electrical characteristics of the green pixel and a burn-in phenomenon caused by a switching threshold shift are suppressed.
  • the device is preferably selected.
  • the liquid crystal display device of the present invention includes the color filter according to the present invention described above, a counter substrate, and a liquid crystal layer formed between the color filter and the counter substrate.
  • a liquid crystal display device of the present invention will be described with reference to the drawings.
  • FIG. 2 is a schematic diagram illustrating an example of a display device of the present invention, and is a schematic diagram illustrating an example of a liquid crystal display device.
  • the liquid crystal display device 40 of the present invention includes a color filter 10, a counter substrate 20 having a TFT array substrate and the like, and a liquid crystal layer formed between the color filter 10 and the counter substrate 20. 30.
  • the liquid crystal display device of the present invention is not limited to the configuration shown in FIG. 2, but can be a configuration generally known as a liquid crystal display device using a color filter.
  • the driving method of the liquid crystal display device of the present invention is not particularly limited, and a driving method generally used for a liquid crystal display device can be employed. Examples of such a drive method include a TN method, an IPS method, an OCB method, and an MVA method. In the present invention, any of these methods can be preferably used. Further, the counter substrate can be appropriately selected and used according to the driving method of the liquid crystal display device of the present invention.
  • a method for forming a liquid crystal layer a method generally used as a method for producing a liquid crystal cell can be used, and examples thereof include a vacuum injection method and a liquid crystal dropping method.
  • FIG. 3 is a schematic diagram illustrating another example of the display device of the present invention, and is a schematic diagram illustrating an example of an organic light emitting display device.
  • the organic light emitting display device 100 of the present invention includes a color filter 10 and an organic light emitter 80.
  • An organic protective layer 50 and an inorganic oxide film 60 may be provided between the color filter 10 and the organic light emitter 80.
  • the transparent anode 71, the hole injection layer 72, the hole transport layer 73, the light emitting layer 74, the electron injection layer 75, and the cathode 76 are sequentially formed on the upper surface of the color filter. Examples thereof include a method and a method in which an organic light emitter 80 formed on another substrate is bonded onto the inorganic oxide film 60.
  • the transparent anode 71, the hole injection layer 72, the hole transport layer 73, the light emitting layer 74, the electron injection layer 75, the cathode 76, and other configurations in the organic light emitting body 80 known structures can be appropriately used.
  • the organic light emitting display device 100 manufactured as described above can be applied to, for example, a passive drive type organic EL display or an active drive type organic EL display.
  • the organic light emitting display device of the present invention is not limited to the configuration shown in FIG. 3, and may be a known configuration as an organic light emitting display device that generally uses a color filter.
  • the acid value of the block copolymer before salt formation was calculated
  • the amine value of the block copolymer before salt formation was determined by a method according to the method described in JIS K 7237.
  • the weight average molecular weight (Mw) of the block copolymer before salt formation was determined as a standard polystyrene equivalent value by GPC (gel permeation chromatography) according to the measurement method of the present invention described above.
  • the glass transition temperature (Tg) of the block copolymer before salt formation and after salt formation is determined by differential scanning calorimetry (DSC) (EXSTAR DSC 7020, manufactured by SII Nanotechnology Co., Ltd.) according to the method described in JIS K7121. It measured using.
  • DSC differential scanning calorimetry
  • EEMA 1-ethoxyethyl methacrylate
  • HEMA 2-hydroxyethyl methacrylate
  • EHMA 2-ethylhexyl methacrylate
  • MMA methyl methacrylate
  • the obtained block copolymer PGMEA solution is reprecipitated in hexane, purified by filtration and vacuum drying, and a structural unit derived from a block containing a structural unit represented by the general formula (I) and a carboxy group-containing monomer A block copolymer A-1 (acid value: 12 mgKOH / g, Tg: 44 ° C.) containing a B block having a solvophilic property was contained.
  • the block copolymer A-1 thus obtained was confirmed by GPC (gel permeation chromatography), and the weight average molecular weight Mw was 8100.
  • the amine value was 110 mgKOH / g.
  • 29.35 parts by mass of block copolymer A-1 was dissolved in 29.35 parts by mass of PGMEA in a 100 mL round bottom flask, and 1.59 parts by mass of phenylphosphonic acid (manufactured by Tokyo Chemical Industry) 0.1 mol) was added to 1 mol of the DMMA unit of the combined A-1, and the mixture was stirred at a reaction temperature of 30 ° C. for 20 hours to obtain a salt type block copolymer A-1 (dispersant a) solution.
  • the amine value after salt formation was calculated as follows.
  • the integrated value of the carbon atom peak adjacent to the non-salt-formed nitrogen atom and the carbon atom peak adjacent to the salt-formed nitrogen atom at the terminal nitrogen site (amino group) From the ratio, the ratio of the number of amino groups that are salt-formed to the total number of amino groups is calculated, and is not different from the theoretical salt-forming ratio (the two acidic groups of all phenylphosphonic acids are different from the DMMA of the block copolymer A-1). It was confirmed that a salt was formed with the terminal nitrogen site).
  • the amine value after salt formation was calculated as 88 mgKOH / g by subtracting the amine value (22 mgKOH / g) of 0.20 mol of DMMA unit from the amine value 110 mgKOH / g before salt formation.
  • the acid value of the block copolymer A-1 after salt formation is the same as that of the block copolymer A-1 before salt formation.
  • Table 1 shows the acid value, amine value, and Tg of the block copolymer A-1 before and after salt formation.
  • block copolymer A-5 The solvent was removed under reduced pressure to obtain block copolymer A-5.
  • the weight average molecular weight determined by GPC measurement (NMP LiBr 10 mM) was 8,350, and the amine value was 95 mgKOH / g.
  • NMP LiBr 10 mM The weight average molecular weight determined by GPC measurement (NMP LiBr 10 mM) was 8,350, and the amine value was 95 mgKOH / g.
  • 29.35 parts by mass of block copolymer A-5 was dissolved in 29.35 parts by mass of PGMEA, and 3.17 parts by mass of phenylphosphonic acid (PPA, manufactured by Tokyo Chemical Industry Co., Ltd.) 0.20 mol) is added to 1 mol of DMMA unit of copolymer A-5, and the mixture is stirred at a reaction temperature of 30 ° C.
  • Synthesis Example 6 Preparation of dispersant f
  • Synthesis Example 5 instead of phenylphosphonic acid, 3.80 parts by mass of benzyl chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) (benzyl chloride is 0.3 mol with respect to 1 mol of DMMA unit of block copolymer A-5) is used.
  • a salt type block copolymer A-6 (dispersant f) solution was synthesized in the same manner as in Synthesis Example 5 except for the above.
  • Table 1 shows the acid value, amine value, and Tg of the obtained block copolymer before and after salt formation.
  • the obtained alkali-soluble resin A is a resin in which a side chain having an ethylenic double bond is introduced into the main chain formed by copolymerization of BzMA, MMA, and MAA using GMA, and has a solid content of 42.6 mass. %, Acid value 74 mgKOH / g, and weight average molecular weight 12000.
  • the weight average molecular weight was measured with a Shodex GPC System-21H (polypropylene) using polystyrene as a standard substance and THF as an eluent.
  • the acid value was measured based on JIS K 0070.
  • Synthesis Example 9 Preparation of alkali-soluble resin B solution
  • Synthesis Example 8 was used except that 20 parts by mass of styrene and 20 parts by mass of N-phenylmaleimide (Tokyo Chemical Industry Co., Ltd.) were used.
  • an alkali-soluble resin B solution was obtained.
  • the solid content was 42.6% by mass
  • the acid value was 74 mgKOH / g
  • the weight average molecular weight was 12,000.
  • Example 1 (1) Production of Colorant Dispersion R1 6.23 parts by mass of Dispersant a solution of Synthesis Example 1 as a dispersant and diketopyrrolopyrrole pigment (BrDPP, product represented by the following chemical formula (2) as a red colorant Name Irgaphor RED S 3621CF, manufactured by BASF) 2.57 parts by mass, C.I. I. Pigment Red 254 (trade name Hostaperm Red D2B-COF LV3781, manufactured by CLARIANT) 3.86 parts by mass, C.I. I.
  • Pigment Red 177 (trade name Chromophthal Red A2B, manufactured by BASF), 4.49 parts by mass of Azo derivative 2 obtained in Production Example 2 as a yellow color material, and alkali-soluble obtained in Synthesis Example 8 14.59 parts by mass of the resin A solution, 66.12 parts by mass of PGMEA, and 100 parts by mass of 2.0 mm zirconia beads were put into a mayonnaise bin, and pre-crushed with a paint shaker (manufactured by Asada Tekko Co., Ltd.).
  • the colored resin composition R1 obtained in the above (2) is placed on a glass substrate (“NA35” manufactured by NH Techno Glass Co., Ltd.) having a thickness of 0.7 mm and a size of 100 mm ⁇ 100 mm. After applying using a spin coater, it is dried at 80 ° C. for 3 minutes using a hot plate, irradiated with 60 mJ / cm 2 of ultraviolet light using an ultrahigh pressure mercury lamp, and further post-baked for 30 minutes in a 230 ° C. clean oven. Thus, the colored layer R1 was formed by adjusting the film thickness so that the film thickness after curing was 2.10 ⁇ m.
  • Examples 2 to 11, Comparative Example 1 (1) Production of Color Material Dispersions R2 to R9 and RC1
  • a solution in Example 1 (1) instead of the dispersant a solution in Example 1 (1), as shown in Table 2, respectively.
  • the type and amount of the dispersant were changed so that the solid content was the same part by mass, and the amount of PGMEA was adjusted so that the total amount was 100 parts by mass.
  • Color material dispersions R2 to R6 were obtained.
  • Examples 7 to 9 are the same as Example (3) (1) except that, in Example 3 (1), the color material type and amount used were changed as shown in Table 2, respectively. Thus, colorant dispersions R7 to R9 were obtained.
  • Example 1 instead of the dispersant a solution, the type and amount of the dispersant are set to be equal to parts by mass.
  • the color material dispersion RC1 was obtained in the same manner as (1) of Example 1 except that the amount of PGMEA was adjusted so that the total amount was 100 parts by mass, and the type and amount of color material were changed. It was.
  • (2) Production of Colored Resin Compositions R2 to R11 and RC1 for Color Filters In Examples 2 to 9 and Comparative Example 1, Table 2 shows the color material dispersion R1 in (2) of Example 1 respectively.
  • the amount of the alkali-soluble resin is adjusted so that the P / V ratio becomes the value shown in Table 2 in order to make the film thickness 2.10 ⁇ m.
  • color resin compositions R2 to R9 and RC1 for color filters were obtained in the same manner as (2) of Example 1. Further, in Example 10, instead of using the alkali-soluble resin A solution in Example 3, the alkali-soluble resin B solution obtained in Synthesis Example 9 was used, and an antioxidant (trade name IRGANOX 1010 (1010)) was used. A colored resin composition R10 for color filters was obtained in the same manner as (2) of Example 3 except that 0.03 parts by mass of BASF) was added.
  • Example 11 as shown in Table 2 for the photoinitiator in Example 10, instead of 0.04 parts by mass of IRG369, an oxime ester photoinitiator (trade name TR-PBG-365 ( PBG365), manufactured by Changzhou Strong Electronic New Materials Co., Ltd.) and 0.04 parts by mass of NCI831, instead of 0.02 parts by mass of oxime ester initiator (trade name TR-PBG-3057 (PBG3057), Changzhou Powerful Electronics)
  • TR-PBG-3057 PBG3057
  • a colored resin composition R11 for a color filter was obtained in the same manner as in (2) of Example 10 except that 0.02 parts by mass of Shinbunshi Co., Ltd. was used.
  • Y150 derivative C.I. I. Pigment Yellow 150 Derivative (Ni Complex) (trade name: LEVASCREEN YELLOW G01, LANXESS Co., Ltd.)
  • Byk-161 Trade name Disperbyk-161 (urethane-based dispersant, solid content 30% by mass, manufactured by Big Chemie)
  • Solvent A Propylene glycol monomethyl ether acetate (PGMEA)
  • Solvent B 3-methoxy-3-methyl-1-butyl acetate
  • Example 12 to 23 (1) Production of Color Material Dispersions R12 to R23 In Examples 12 to 23, as shown in Table 3 in Example 1 (1), the types and blending amounts of color materials were changed, and the total amount Color material dispersions R12 to R23 were obtained in the same manner as in Example 3 (1) except that the amount of PGMEA was adjusted to 100 parts by mass.
  • (2) Production of Colored Resin Compositions R12 to R23 for Color Filter The above color material dispersions R12 to R23 were used in place of the color material dispersion R3 in (2) of Example 11, and the film thickness was 2.50 ⁇ m.
  • a colored resin composition for a color filter was prepared in the same manner as in (2) of Example 11 except that the amount of the alkali-soluble resin was adjusted so that the P / V ratio was the value shown in Table 3. R12 to R23 were obtained. (3) Formation of colored layer In the same manner as (3) of Example 11 except that the colored resin compositions R12 to R23 were used in place of the colored resin composition R11 in (3) of Example 11. Thus, colored layers R12 to R23 were obtained.
  • R264 C.I. I. Pigment Red 264 (trade name: Irgazin Red L 4010 HD, manufactured by BASF)
  • R242 C.I. I. Pigment Red 242 (Brand name: Novoperm SCARlet 4RF, manufactured by CLARIANT)
  • O38 C.I. I. Pigment Orange 38 (trade name: Novoperm Red HF, manufactured by CLARIANT)
  • the transmittance is 20% or less, and the transmittance at a wavelength of 640 nm is 70% or more, which corresponds to the red color material of the present invention.
  • R272 C.I. I. Pigment Red 272 (trade name: Irgazin Flame Red K 3800, manufactured by BASF) Y150 derivative: C.I. I.
  • Pigment Yellow 150 Derivative (Ni Complex) (trade name: LEVASCREEN YELLOW G01, LANXESS Co., Ltd.)
  • Byk-161 Trade name Disperbyk-161 (urethane-based dispersant, solid content 30% by mass, manufactured by Big Chemie)
  • 6919 Trade name Disperbyk-LPN6919 (polymer having a structural unit represented by the general formula (I), amine value 120 mgKOH / g, solid content 60% by mass, manufactured by Big Chemie)
  • Examples 24-41 (1) Production of Color Material Dispersions R24 to R41 In Examples 24 to 41, as shown in Table 4 in Example 3 (1), the type and blending amount of color materials were changed, and the total amount Color material dispersions R24 to R41 were obtained in the same manner as (1) of Example 3 except that the amount of PGMEA was adjusted to 100 parts by mass.
  • (2) Production of Colored Resin Compositions R24 to R41 for Color Filter The above color material dispersions R24 to R41 were used in place of the color material dispersion R3 in (2) of Example 11, and the film thickness was 2.80 ⁇ m.
  • a colored resin composition for a color filter was prepared in the same manner as in (2) of Example 11 except that the amount of the alkali-soluble resin was adjusted so that the P / V ratio was the value shown in Table 4. R24 to R41 were obtained. (3) Formation of colored layer In the same manner as (3) of Example 11 except that the colored resin compositions R24 to R41 were used in place of the colored resin composition R11 in (3) of Example 11. Thus, colored layers R24 to R41 were obtained.
  • Example 42 (1) Production of colorant dispersion 6.23 parts by mass of the dispersant c solution of Synthesis Example 3 as a dispersant, and diketopyrrolopyrrole pigment represented by the chemical formula (2) as a colorant (BrDPP, trade name: Irgaphor RED S 3621CF, manufactured by BASF) 14.0 parts by weight, 14.59 parts by weight of the alkali-soluble resin A solution obtained in Synthesis Example 8, 66.20 parts by weight of PGMEA, and 100 parts by weight of 2.0 mm zirconia beads in a mayonnaise bin, Shake with a paint shaker (manufactured by Asada Tekko Co., Ltd.) for 1 hour as preliminary crushing, then take out 2.0 mm zirconia beads with a particle size of 2.0 mm, add 200 parts by mass of zirconia beads with a particle size of 0.1 mm, and similarly As this crushing, dispersion was performed for 4 hours with a paint shaker to obtain a red color material
  • red color material dispersion r1 instead of using 13.0 parts by mass of the diketopyrrolopyrrole pigment (BrDPP) represented by the chemical formula (2) as the color material, C.I. I.
  • a red color material dispersion r2 was obtained in the same manner as the red color material dispersion r1 except that 13.0 parts by mass of Pigment Red 254 (trade name: Hostasper Red D2B-COF LV3781, manufactured by CLARIANT) was used.
  • Pigment Red 254 trade name: Hostasper Red D2B-COF LV3781, manufactured by CLARIANT
  • a red color material dispersion r3 was obtained in the same manner as the red color material dispersion r1 except that 13.0 parts by mass of Pigment Red 177 (trade name: Palogen Red L 4045, manufactured by BASF) was used. Instead of using 13.0 parts by mass of the diketopyrrolopyrrole pigment (BrDPP) represented by the chemical formula (2) as a colorant in the red colorant dispersion r1, 13.0 parts by mass of Azo derivative 2 as a colorant is used.
  • a yellow color material dispersion y was obtained in the same manner as in the red color material dispersion r1 except that a part of the red color material dispersion r1 was used.
  • Example 43 to 48 (1) Production of Colorant Dispersion R47 In Example 47, as shown in Table 5 in Example 1 (1), solid content was obtained by using Dispersant g solution instead of Dispersant a solution. Were changed to be the same part by mass, and a colorant dispersion R47 was obtained in the same manner as (1) of Example 1 except that the amount of PGMEA was adjusted so that the total amount was 100 parts by mass.
  • Example 2 (2) of Example 3 except that 0.04 parts by mass of NCI831 was used instead of 0.02 parts by mass of an oxime ester-based initiator (trade name Irgacure OXE 02 (OXE02), manufactured by BASF).
  • a colored resin composition R43 for color filters was obtained.
  • Example 44 instead of 0.03 part by mass of the antioxidant (trade name IRGANOX 1010 (1010), manufactured by BASF) in Example 11, the antioxidant (trade name ADK STAB AO-40 (AO- 40), manufactured by ADEKA) Except for using 0.03 parts by mass, a colored resin composition R44 for color filters was obtained in the same manner as (2) of Example 11.
  • Example 45 instead of 0.03 part by mass of the antioxidant (trade name IRGANOX 1010 (1010), manufactured by BASF) in Example 11, the latent antioxidant (Compound a) of Synthesis Example 10 was used.
  • a colored resin composition R45 for color filters was obtained in the same manner as (2) of Example 11 except that 0.03 part by mass was used.
  • Example 46 instead of adding 0.03 part by mass of the antioxidant (trade name IRGANOX 1010 (1010), manufactured by BASF) in Example 11, an ultraviolet absorber (benzotriazole compound, trade name)
  • an ultraviolet absorber (benzotriazole compound, trade name)
  • a colored resin composition R46 for color filters was obtained in the same manner as (2) of Example 11 except that 0.03 parts by mass of TINUVIN 329 BASF) was added.
  • Example 47 a colored resin composition for a color filter was obtained in the same manner as in (3) of Example 3 except that the color material dispersion R47 was used instead of the color material dispersion R3. R47 was obtained.
  • Example 48 the colorant dispersion R47 was used instead of the colorant dispersion R3 in Example 43, and an antioxidant (trade name ADK STAB AO-40 (AO-40), manufactured by ADEKA) 0.03
  • Product R48 was obtained.
  • (3) Formation of colored layer In the same manner as (3) of Example 1 except that the colored resin compositions R43 to R48 were used in place of the colored resin composition R1 in (1) of Example 1. As a result, colored layers R43 to R48 were obtained.
  • Viscosity stability evaluation criteria A: Change rate of viscosity before and after storage is less than 10%
  • this is a value when the color material is 13 mass% with respect to the total mass including the solvent of the color material dispersion. Even if the evaluation result is C, the color material dispersion can be used practically. However, if the evaluation result is B, the color material dispersion is better. If the evaluation result is A, the color material dispersion is excellent in dispersion stability. Are better.
  • ⁇ Optical performance evaluation, contrast evaluation> The contrast, chromaticity (x, y), and luminance (Y) of the colored layers obtained in the examples and comparative examples were measured using a spectral characteristic measuring device LCF-1500M manufactured by Otsuka Electronics and a contrast measuring device CT-1B manufactured by Aisaka Electric. Measured.
  • the retardation of the colored layer was determined using the retardation in the thickness direction (Rth) calculated by the following formula as an index.
  • Retardation (Rth) was measured using a retardation layer measuring apparatus (Axoscan TM Mueller Matrix Polarimeter manufactured by AXOMETRICS). The measurement wavelength of the red colored layer was measured at 620 nm and 665 nm.
  • Rth ((Nx + Ny) / 2 ⁇ Nz) d
  • Nx Refractive index in the in-plane slow axis direction
  • Ny Refractive index in the in-plane fast axis direction
  • Nz Refractive index in the thickness direction
  • d Film thickness (nm)
  • the colored resin compositions for color filters obtained in the examples and comparative examples were respectively applied to a spin coater on a 100 mm ⁇ 100 mm glass substrate (“NA35” manufactured by NH Techno Glass Co., Ltd.) with a thickness of 0.7 mm. After being applied, it was dried at 60 ° C. for 3 minutes using a hot plate to form a colored layer having a thickness of 2.5 ⁇ m. The glass plate on which the colored layer was formed was shower-developed for 60 seconds using a 0.05% by mass aqueous potassium hydroxide solution as an alkaline developer.
  • the glass substrate After observing the unexposed portion (50 mm ⁇ 50 mm) of the glass substrate after the formation of the colored layer by visual observation, the glass substrate is thoroughly wiped with a lens cleaner (trade name Toraysee MK Clean Cloth, manufactured by Toray Industries, Inc.), The coloring degree of the lens cleaner was visually observed.
  • the above evaluation criteria are AA, A, B, or C, it can be used practically, but if the evaluation result is B, further A, and further AA, the effect is more excellent. ing.
  • the color filter colored resin composition obtained in each example and each comparative example was formed on a glass substrate (NH Techno Glass Co., Ltd., “NA35”) with a thickness of 1 after post-baking using a spin coater. After coating with a film thickness to form a colored layer of .6 ⁇ m, it is dried at 60 ° C. for 3 minutes using a hot plate, and irradiated with ultraviolet light of 60 mJ / cm 2 using an ultrahigh pressure mercury lamp without using a photomask. As a result, a colored layer was formed on the glass substrate.
  • AA Contact angle of 80 degrees or more
  • A Contact angle of 75 degrees or more and less than 80 degrees
  • B Contact angle of 65 degrees or more and less than 75 degrees
  • C Contact angle of 50 degrees or more and less than 65 degrees
  • D Contact angle of less than 50 degrees
  • Water stain evaluation standard is AA If it is A or B, it can be used practically, but if the evaluation result is A and further AA, the effect is more excellent.
  • ⁇ SiN adhesion evaluation> The colored resin composition for color filter obtained in each example and each comparative example was applied on a SiN substrate (manufactured by Foresight Co., Ltd.) using a spin coater, and then at 80 ° C. using a hot plate. The film is dried for 3 minutes, irradiated with 60 mJ / cm 2 ultraviolet rays using an ultra-high pressure mercury lamp, and further post-baked for 30 minutes in a clean oven at 230 ° C., so that the film thickness after curing becomes 2.10 ⁇ m. The colored layer was formed by adjusting the thickness.
  • the obtained colored layer was subjected to a cross-cut test in accordance with JIS K 5600-5-6, and after repeating the peeling operation with the tape 5 times, the presence or absence of peeling of the coating film was observed and evaluated according to the following evaluation criteria. did.
  • SiN adhesion evaluation criteria AA: There is no peeling of the eyes of any lattice A: Although there is a small peeling of the coating film at the intersection of the cuts, the exclusive area of the peeling is less than 5%.
  • B The coating film is peeled off at the intersections along the cut line. Exclusive area of peeling is 5% or more and less than 15%
  • C The coating film is partially or totally peeled along the cut line. Exclusive area of peeling is 15% or more and less than 35%
  • the color material dispersion of Comparative Example 2 in which the urethane-based dispersant was combined had poor viscosity stability.
  • the colorant dispersions of Comparative Examples 3 to 7 in which a conventional yellow color material is combined with a red color material may use a dispersant that is a polymer having a structural unit represented by the general formula (I). It was shown that the viscosity stability was poor.
  • the red color material is combined with the specific yellow color material, and further, the dispersant is a polymer having a structural unit represented by the general formula (I).
  • the colored resin composition has good colorant dispersion stability, and it has been clarified that the colored layer using the colored resin composition is excellent in contrast while the retardation value is reduced.
  • each of the colored layers using the colored resin compositions of Examples 1 to 48 has excellent adhesion to SiN, and among them, the colored resin compositions of Examples 11, 44, 45, 46, and 48 were used. It was also revealed that the colored layer has excellent adhesion to SiN. Further, the adhesion of Example 10 to SiN was A, which was close to AA, and was good.
  • Comparative Examples 1 and 3 to 7 in which color materials different from the Examples are combined are inferior in contrast and large in phase difference value as compared with Examples having the same chromaticity coordinates (x, y). It was. Further, even when the specific yellow color material is combined with the red color material, the comparative example 2 in which the urethane-based dispersant is combined is inferior in contrast to the example of the same chromaticity coordinate (x, y). The phase difference value was large. Further, in Comparative Examples 1, 3 to 7, the P / V ratio in the colored resin composition tends to be larger and the adhesion to SiN is inferior as compared with Examples having the same chromaticity coordinates (x, y). It was. Furthermore, Comparative Example 1 was inferior in terms of solvent resolubility, development residue suppression, development resistance, and water stain as compared with Examples having the same chromaticity coordinates (x, y).
  • the alkali-soluble resin includes both a maleimide structure having a hydrocarbon ring and a styrene structure, and in the example in which an antioxidant is added, a colored layer having improved development residue and brightness is formed. It was revealed that Further, it has been clarified that when two types of oxime ester photoinitiators are used in combination with an antioxidant, a colored layer having improved development resistance and luminance is formed.
  • an oxime ester photoinitiator having a fluorene skeleton and an oxime ester photoinitiator having diphenyl sulfide in terms of excellent luminance, and it has an oxime ester photoinitiator having a carbazole skeleton and diphenyl sulfide.
  • the combined use of an oxime ester photoinitiator was preferred in that the effect of suppressing water stain was increased.
  • Example 44 using a hindered phenol-based antioxidant having a molecular weight of 500 or less and a molecular weight per phenolic hydroxyl group of 200 equivalents or less is colored with improved brightness while reducing the retardation value.
  • a layer was formed.
  • the contrast was A close to AA, and a colored layer with improved contrast was obtained.
  • Example 45 using the latent antioxidant a phase difference value was reduced, and a colored layer having a contrast of A, which was close to AA, and an improved contrast was obtained.
  • Example 46 using the ultraviolet absorber a colored layer having a reduced retardation value, a contrast A close to AA, and an improved contrast was obtained.
  • a hinder having an oxime ester photoinitiator having a carbazole skeleton and an oxime ester photoinitiator having diphenyl sulfide having a molecular weight of 500 or less and a molecular weight per phenolic hydroxyl group of 200 equivalents or less.
  • Example 48 using a combination of a dophenol-based antioxidant and an ultraviolet absorber a colored layer with improved brightness and improved water stain suppression effect was formed while the retardation value was reduced.
  • the contrast was A close to AA, and a colored layer with improved contrast was obtained.

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JP2020101759A (ja) * 2018-12-25 2020-07-02 東洋インキＳｃホールディングス株式会社 感光性着色組成物、カラーフィルタおよび液晶表示装置
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