KR20100003699A - Colored photosensitive resin composition - Google Patents

Colored photosensitive resin composition Download PDF

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KR20100003699A
KR20100003699A KR20090057409A KR20090057409A KR20100003699A KR 20100003699 A KR20100003699 A KR 20100003699A KR 20090057409 A KR20090057409 A KR 20090057409A KR 20090057409 A KR20090057409 A KR 20090057409A KR 20100003699 A KR20100003699 A KR 20100003699A
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formula
group
resin composition
substituted
photosensitive resin
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KR20090057409A
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KR101461636B1 (en
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유코 시로우치
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스미또모 가가꾸 가부시키가이샤
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/28—Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/201—Filters in the form of arrays
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Architecture (AREA)
  • Structural Engineering (AREA)
  • Optics & Photonics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials For Photolithography (AREA)
  • Optical Filters (AREA)

Abstract

PURPOSE: A colored photosensitive resin composition is provided to obtain a high brightness coating film and color filter while including dye and pigment. CONSTITUTION: A colored photosensitive resin composition comprises (A) a coloring agent, (B) a binder resin, (C) a photopolymerizable compound, (D) a photopolymerization initiator, and (E) solvent. The coloring agent comprises an organic solvent soluble dye including a compound represented by chemical formula(1), and organic pigment. In chemical formula(1), R^1~R^4 are hydrogen atom, -R^6 or C6~10 aromatic hydrocarbon group; R^5 is SO3-, -SO3H, -SO3M, -CO2H, -CO2R6, -SO3R6, -SO2NHR8 or -SO2NR8R9; m is an integer of 0~5; X is halogen atom; and a is an integer of 0 or 1.

Description

Colored photosensitive resin composition {COLORED PHOTOSENSITIVE RESIN COMPOSITION}

This invention relates to the coloring photosensitive resin composition suitable for formation of the colored image which comprises the color filter used for a liquid crystal display element or a solid-state image sensor, and the color filter using the said coloring photosensitive resin composition.

In recent years, high definition, high brightness, and high contrast have been desired in color filters. In order to achieve this, high color purity of a color filter advances and it can be seen that the pigment concentration in a colored photosensitive resin composition becomes high. However, when the pigment concentration is high, since the pigment has a constant particle diameter and scatters light, there is a problem that the contrast of the color filter formed by using the colored photosensitive resin composition containing the same decreases.

Therefore, specifically, for example, by using a combination of a pyrazole-based squarylium compound as a dye expressing color only by light absorption and a blue pigment pigment blue (PB) 15: 6 as a pigment, The technique which achieves contrast is disclosed (patent document 1).

[Patent Document 1]

Japanese Patent Application Laid-Open No. 2006-079012

Moreover, in order to achieve the high brightness of a color filter, development of the coloring photosensitive resin composition containing the dye and pigment of other combinations other than the combination specifically disclosed by patent document 1 is desired.

MEANS TO SOLVE THE PROBLEM The present inventors discovered that the coloring photosensitive resin composition containing some kind of dye and a pigment provides a high-brightness coating film as a result of studying so that the said subject might be solved.

This invention is colored photosensitive resin composition containing a coloring agent (A), binder resin (B), a photopolymerizable compound (C), a photoinitiator (D), and a solvent (E), A coloring agent (A) is a formula (1) It is a coloring photosensitive resin composition which is an organic solvent soluble dye containing the compound represented by) and the coloring agent containing an organic pigment.

Figure 112009038838755-PAT00002

(In formula (1), R <1> -R <4> represents a hydrogen atom, -R <6> or a C6-C10 aromatic hydrocarbon group each independently. The hydrogen atom contained in the said C6-C10 aromatic hydrocarbon group is , a halogen atom, -R 6, -OH, -OR 6 , -SO 3 -, -SO 3 H, -SO 3 M, -CO 2 H, -CO 2 R 6, -SO 3 R 6, -SO 2 NHR 8 or -SO 2 NR 8 R 9 may be substituted.

R 5 is, -SO 3 -, -SO 3 H , -SO 3 M, -CO 2 H, -CO 2 R 6, a -SO 3 R 6, -SO 2 NHR 8 or -SO 2 NR 8 R 9 Indicates.

m represents the integer of 0-5. When m is an integer of 2 or more, some R <5> may be the same or may differ.

X represents a halogen atom. a represents the integer of 0 or 1.

R <6> represents a C1-C10 saturated hydrocarbon group. The hydrogen atom contained in the C1-C10 saturated hydrocarbon group may be substituted with the halogen atom. The methylene group contained in the C1-C10 saturated hydrocarbon group may be substituted with an oxygen atom, a carbonyl group or -NR 6- .

R 8 and R 9 each independently represent a linear or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or -Q. Alternatively, R 8 and R 9 may be bonded to each other to form a heterocyclic ring having 1 to 10 carbon atoms.

Q represents an aromatic hydrocarbon group having 6 to 10 carbon atoms or an aromatic heterocyclic group having 5 to 10 carbon atoms, and the hydrogen atoms contained in the aromatic hydrocarbon group and the aromatic heterocyclic group are -OH, R 6 , -OR 6 , -NO 2 , -CH = CH 2 , -CH = CHR 6 or a halogen atom may be substituted.

Hydrogen atoms contained in the cycloalkyl group of 1 to 10 carbon atoms and straight-chain or branched alkyl group having a carbon number of 3 to 30 of the, hydroxyl group, may be substituted with a halogen atom, -Q, -CH = CH 2 or -CH = CHR 6.

The methylene group contained in a linear or branched alkyl group having 1 to 10 carbon atoms and a cycloalkyl group having 3 to 30 carbon atoms may be substituted with an oxygen atom, a carbonyl group, or -NR 6- ,

The hydrogen atom contained in a C1-C10 heterocycle may be substituted by R <6> , -OH or -Q.

M represents a sodium atom or a potassium atom.)

Moreover, this invention is the said coloring photosensitive resin composition whose compound represented by Formula (1) is a compound represented by Formula (1-1).

Figure 112009038838755-PAT00003

(In formula (1-1), R <11> -R <14> represents a hydrogen atom, -R <6>, or a C6-C10 aromatic hydrocarbon group each independently. Hydrogen atom contained in the said C6-C10 aromatic hydrocarbon group. is a halogen atom, -R 6, -OH, -OR 6 , -SO 3 -, -SO 3 H, -SO 3 Na, -CO 2 H, -CO 2 R 6, -SO 3 R 6, -SO It may be substituted by 2 NHR 8 or -SO 2 NR 8 R 9 .

R 15 is a hydrogen atom, -SO 3 -, -SO 3 H , -SO 2 NHR 8 or -SO 2 represents an NR 8 R 9.

R 16 represents —SO 3 — , —SO 3 H, —SO 2 NHR 8, or —SO 2 NR 8 R 9 .

R 6 , R 8 , R 9 , m, X and a represent the same meaning as described above.)

Moreover, this invention is the said coloring photosensitive resin composition whose compound represented by Formula (1) is a compound represented by Formula (1-2).

Figure 112009038838755-PAT00004

In (formula (1-2), R 21 ~R 24 each independently represents an aromatic hydrocarbon group of a hydrogen atom, -R 26, or 6 to 10 carbon atoms, hydrogen atoms contained in the carbon number of 6 to 10 aromatic hydrocarbon groups It is a halogen atom, -R 26, -OH, -OR 26 , -SO 3 -, -SO 3 Na, -CO 2 H, -CO 2 R 26, -SO 3 H, -SO 3 R 26 or -SO 2 NHR 28 may be substituted.

R 25 represents —SO 3 — , —SO 3 Na, —CO 2 H, —CO 2 R 26 , —SO 3 H or SO 2 NHR 28 .

R <26> represents a C1-C10 saturated hydrocarbon group. The hydrogen atom contained in the said C1-C10 saturated hydrocarbon group may be substituted by -OR <26> or a halogen atom.

R 28 represents a hydrogen atom, -R 26 , -CO 2 R 26 or a C6-C10 aromatic hydrocarbon group, and the hydrogen atom contained in the C6-C10 aromatic hydrocarbon group is -R 26 or -OR 26 It may be substituted.

m, X, and a represent the same meaning as the above.)

Moreover, this invention is the said coloring photosensitive resin composition whose compound represented by Formula (1) is a compound represented by Formula (1-3).

Figure 112009038838755-PAT00005

(In formula (1-3) in, R 31 and R 32 each independently represents a phenyl group. A hydrogen atom contained in the phenyl group, a halogen atom, -R 26, -OR 26, -CO 2 R 26, It may be substituted by -SO 3 R 26 or -SO 2 NHR 28 .

R 33 represents -SO 3 - or -SO 2 NHR 28 .

R 34 represents a hydrogen atom, -SO 3 - or -SO 2 NHR 28 .

R 26 , R 28 , X and a represent the same meaning as described above.)

Moreover, this invention is the said coloring photosensitive resin composition whose compound represented by Formula (1) is a compound represented by Formula (1-4).

Figure 112009038838755-PAT00006

(In formula (1-4), R 41 and R 42 each independently represent a phenyl group.) The hydrogen atom contained in the phenyl group may be substituted with -R 26 or -SO 2 NHR 28 .

R 43 represents -SO 3 - or -SO 2 NHR 28 .

R 26 , R 28 , X and a represent the same meaning as described above.)

In the present invention, the organic pigment is C.I. It is the said coloring photosensitive resin composition which is organic pigment containing pigment blue 15: 6.

Moreover, this invention is C.I. in a coloring agent (A). It is the said coloring photosensitive resin composition whose mass ratio of pigment blue 15: 6 and the organic solvent soluble dye containing the compound represented by Formula (1) is 97: 3-50: 50.

Moreover, this invention is a coating film formed using the said colored photosensitive resin composition.

Moreover, this invention is a color filter formed using the said colored photosensitive resin composition.

Moreover, this invention is the said color filter formed by the photolithographic method.

The coloring photosensitive resin composition of this invention contains a coloring agent (A), and a coloring agent (A) may be called the organic solvent soluble dye (the "dye (1)" hereafter) containing the compound represented by Formula (1). ) Is a colorant containing.

As the dye 1, it selects according to the color of the color filter made into the objective, and can also mix and use a some dye. It is preferable to have sufficient solubility in the solvent contained in a coloring photosensitive resin composition, and to have sufficient solubility with respect to a developing solution so that pattern formation can be carried out at the image development process at the time of pattern formation.

Figure 112009038838755-PAT00007

In (formula (1), R 1 ~R 4 each independently represents an aromatic hydrocarbon group of a hydrogen atom, -R 6, or 6 to 10 carbon atoms, hydrogen atoms contained in the carbon number of 6 to 10 aromatic hydrocarbon groups are, a halogen atom, -R 6, -OH, -OR 6 , -SO 3 -, -SO 3 H, -SO 3 M, -CO 2 H, -CO 2 R 6, -SO 3 R 6, -SO 2 NHR 8 or -SO 2 NR 8 R 9 may be substituted.

R 5 is, -SO 3 -, -SO 3 H , -SO 3 M, -CO 2 H, -CO 2 R 6, a -SO 3 R 6, -SO 2 NHR 8 or -SO 2 NR 8 R 9 Indicates.

m represents the integer of 0-5. When m is an integer of 2 or more, some R <5> may be the same or may differ.

X represents a halogen atom. a represents the integer of 0 or 1.

R <6> represents a C1-C10 saturated hydrocarbon group. The hydrogen atom contained in the C1-C10 saturated hydrocarbon group may be substituted with the halogen atom. The methylene group contained in the C1-C10 saturated hydrocarbon group may be substituted with an oxygen atom, a carbonyl group or -NR 6- .

R 8 and R 9 each independently represent a linear or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or -Q. Alternatively, R 8 and R 9 may be bonded to each other to form a heterocyclic ring having 1 to 10 carbon atoms.

Q represents an aromatic hydrocarbon group having 6 to 10 carbon atoms or an aromatic heterocyclic group having 5 to 10 carbon atoms, and the hydrogen atoms contained in the aromatic hydrocarbon group and the aromatic heterocyclic group include -OH, R 6 , -OR 6 , -NO 2 , -CH = CH 2 , -CH = CHR 6 or a halogen atom may be substituted.

Hydrogen atoms contained in the cycloalkyl group of 1 to 10 carbon atoms and straight-chain or branched alkyl group having a carbon number of 3 to 30 of the, hydroxyl group, may be substituted with a halogen atom, -Q, -CH = CH 2 or -CH = CHR 6.

The methylene group contained in a linear or branched alkyl group having 1 to 10 carbon atoms and a cycloalkyl group having 3 to 30 carbon atoms may be substituted with an oxygen atom, a carbonyl group, or -NR 6- ,

The hydrogen atom contained in a C1-C10 heterocycle may be substituted by R <6> , -OH or -Q.

M represents a sodium atom or a potassium atom.)

As R 6 , methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, neopentyl, cyclopentyl, hexyl, cyclohexyl, heptyl, cycloheptyl, octyl, 2-ethylhexyl, cyclooctyl, nonyl , Decanyl, tricyclodecanyl, methoxypropyl, ethoxypropyl, hexyloxypropyl, 2-ethylhexyloxypropyl, methoxyhexyl, ethoxypropyl and the like.

Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms include phenyl and naphthyl.

Fluorine, chlorine, bromine, etc. are mentioned as a halogen atom mentioned as a substituent of the said C6-C10 aromatic hydrocarbon group.

Examples of -SO 3 R 6 include methanesulfonyl, ethanesulfonyl, hexanesulfonyl, decansulfonyl, and the like.

As —CO 2 R 6 , methyloxycarbonyl, ethyloxycarbonyl, propyloxycarbonyl, isopropyloxycarbonyl, butyloxycarbonyl, isobutyloxycarbonyl, pentyloxycarbonyl, isopentyloxycarbonyl, Neopentyloxycarbonyl, cyclopentyloxycarbonyl, hexyloxycarbonyl, cyclohexyloxycarbonyl, heptyloxycarbonyl, cycloheptyloxycarbonyl, octyloxycarbonyl, 2-ethylhexyloxycarbonyl, Cyclooctyloxycarbonyl, nonyloxycarbonyl, decanyloxycarbonyl, tricyclodecanyloxycarbonyl, methoxypropyloxycarbonyl, ethoxypropyloxycarbonyl, hexyloxypropyloxycarbonyl, 2-ethylhexyl Oxypropyloxycarbonyl, methoxyhexyloxycarbonyl, and the like.

As -SO 2 NHR 8 , sulfamoyl, methane sulfamoyl, ethane sulfamoyl, propane sulfamoyl, isopropane sulfamoyl, butane sulfamoyl, isobutane sulfamoyl, pentansulfamoyl, isopentansulfamoyl, neopentane sulfamoyl, Cyclopentane sulfamoyl, hexane sulfamoyl, cyclohexane sulfamoyl, heptane sulfamoyl, cycloheptan sulfamoyl, octane sulfamoyl, 2-ethylhexane sulfamoyl, 1,5-dimethylhexane sulfamoyl, cyclooctane sulfamoyl, nonane sulfamo Moyl, decansulfamoyl, tricyclodecansulfamoyl, methoxy propanesulfamoyl, ethoxypropanesulfamoyl, propoxypropanesulfamoyl, isopropoxypropanesulfamoyl, hexyloxypropanesulfamoyl, 2-ethylhexyloxypropane Sulfamoyl, methoxyhexane sulfamoyl, 3-phenyl-1-methylpropanesulfamoyl and the like.

Examples of -SO 2 NHR 8 and -SO 2 NR 8 R 9, there may be mentioned more groups represented by the following formula.

Figure 112009038838755-PAT00008

Figure 112009038838755-PAT00009

Figure 112009038838755-PAT00010

Figure 112009038838755-PAT00011

In the formula, X 1 represents a halogen atom. Examples of the halogen atom in X 1 include a fluorine atom, a chlorine atom and a bromine atom.

Figure 112009038838755-PAT00012

Figure 112009038838755-PAT00013

Figure 112009038838755-PAT00014

Figure 112009038838755-PAT00015

In said formula, X <3> represents a C1-C3 alkyl group or a C1-C3 alkoxyl group, and the hydrogen atom of the said alkyl group and the alkoxy group may be substituted by the halogen atom.

Methyl, ethyl, propyl, isopropyl, perfluoromethyl, etc. are mentioned as a C1-C3 alkyl group which may be substituted by the halogen atom.

As a C1-C3 alkoxy group which may be substituted by the halogen atom, methoxy, ethoxy, propoxy, etc. are mentioned.

Figure 112009038838755-PAT00016

Figure 112009038838755-PAT00017

Figure 112009038838755-PAT00018

Figure 112009038838755-PAT00019

In said formula, X <2> represents a C1-C3 alkyl group, a C1-C3 alkoxyl group, a halogen atom, or a nitro group, and the hydrogen atom of the said alkyl group and the alkoxy group may be substituted by the halogen atom.

Examples of the halogen atom in X 2 include a fluorine atom, a chlorine atom and a bromine atom.

Methyl, ethyl, propyl, isopropyl, perfluoromethyl, etc. are mentioned as a C1-C3 alkyl group which may be substituted by the halogen atom.

As a C1-C3 alkoxy group which may be substituted by the halogen atom, methoxy, ethoxy, propoxy, etc. are mentioned.

Figure 112009038838755-PAT00020

Figure 112009038838755-PAT00021

Figure 112009038838755-PAT00022

Figure 112009038838755-PAT00023

Figure 112009038838755-PAT00024

In said formula, X <2> represents the same meaning as the above.

Figure 112009038838755-PAT00025

Figure 112009038838755-PAT00026

Figure 112009038838755-PAT00027

Figure 112009038838755-PAT00028

In said formula, X <3> represents the same meaning as the above.

Examples of R 8 and R 9 included in —SO 2 NR 8 R 9 include a branched alkyl group having 6 to 8 carbon atoms, an alicyclic alkyl group having 5 to 7 carbon atoms, an allyl group, a phenyl group, and a carbon group having 8 to 10 carbon atoms. Aralkyl groups, hydroxyl-containing alkyl and aryl groups having 2 to 8 carbon atoms, or alkoxyl-containing alkyl or aryl groups having 2 to 8 carbon atoms are preferred, and 2-ethylhexyl is particularly preferred.

The substituent of the aromatic hydrocarbon group of 6 to 10 carbon atoms, ethyl, propyl, phenyl, dimethylphenyl, a -SO 3 R 6, or -SO 2 NHR 8 is preferred.

Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms having a substituent include methylphenyl, dimethylphenyl, trimethylphenyl, ethylphenyl, hexylphenyl, decanylphenyl, fluorophenyl, chlorophenyl, bromophenyl, hydroxyphenyl, methoxyphenyl, Dimethoxyphenyl, ethoxyphenyl, hexyloxyphenyl, decanyloxyphenyl, trifluoromethylphenyl, etc. are mentioned.

At least one of R 1 and R 2 or at least one of R 3 and R 4 is preferably an alkyl group having 1 to 4 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted.

It is preferable that at least one of R <1> and R <2> , and at least one of R <3> and R <4> is a C1-C4 alkyl group or a C6-C10 aromatic hydrocarbon group which may be substituted.

At least one of R 1 and R 2 , and at least one of R 3 and R 4 are more preferably a C 6-10 aromatic hydrocarbon group which may be substituted.

R 5 is carboxyl, ethyloxycarbonyl, sulfoxyl, 2-ethylhexyloxypropanesulfamoyl, 1,5-dimethylhexanesulfamoyl, 3-phenyl-1-methylpropanesulfamoyl, isopropoxypropanesulfamoyl Is preferably.

It is preferable that the compound represented by Formula (1) is a compound represented by Formula (1-1).

Figure 112009038838755-PAT00029

(In formula (1-1), R <11> -R <14> represents a hydrogen atom, -R <6>, or a C6-C10 aromatic hydrocarbon group each independently. Hydrogen atom contained in the said C6-C10 aromatic hydrocarbon group. is a halogen atom, -R 6, -OH, -OR 6 , -SO 3 -, -SO 3 H, -SO 3 Na, -CO 2 H, -CO 2 R 6, -SO 3 R 6, -SO It may be substituted by 2 NHR 8 or -SO 2 NR 8 R 9 .

R 15 is a hydrogen atom, -SO 3 -, -SO 3 H , -SO 2 NHR 8 or -SO 2 represents an NR 8 R 9.

R 16 represents —SO 3 — , —SO 3 H, —SO 2 NHR 8, or —SO 2 NR 8 R 9 .

R 6 , R 8 , R 9 , m, X and a represent the same meaning as described above.)

It is preferable that the compound represented by Formula (1) is a compound represented by Formula (1-2).

Figure 112009038838755-PAT00030

In (formula (1-2), R 21 ~R 24 each independently represents an aromatic hydrocarbon group of a hydrogen atom, -R 26, or 6 to 10 carbon atoms, hydrogen atoms contained in the carbon number of 6 to 10 aromatic hydrocarbon groups It is a halogen atom, -R 26, -OH, -OR 26 , -SO 3 -, -SO 3 Na, -CO 2 H, -CO 2 R 26, -SO 3 H, -SO 3 R 26 or -SO 2 NHR 28 may be substituted.

R 25 represents —SO 3 — , —SO 3 Na, —CO 2 H, —CO 2 R 26 , —SO 3 H or SO 2 NHR 28 .

R <26> represents a C1-C10 saturated hydrocarbon group. The hydrogen atom contained in the said C1-C10 saturated hydrocarbon group may be substituted by -OR <26> or a halogen atom.

R 28 represents a hydrogen atom, -R 26 , -CO 2 R 26 or a C6-C10 aromatic hydrocarbon group, and the hydrogen atom contained in the C6-C10 aromatic hydrocarbon group is -R 26 or -OR 26 It may be substituted.

m, X, and a represent the same meaning as the above.)

It is preferable that the compound represented by Formula (1) is a compound represented by Formula (1-3).

Figure 112009038838755-PAT00031

(In formula (1-3) in, R 31 and R 32 each independently represents a phenyl group. A hydrogen atom contained in the phenyl group, a halogen atom, -R 26, -OR 26, -CO 2 R 26, It may be substituted by -SO 3 R 26 or -SO 2 NHR 28 .

R 33 represents -SO 3 - or -SO 2 NHR 28 .

R 34 represents a hydrogen atom, -SO 3 - or -SO 2 NHR 28 .

R 26 , R 28 , X and a represent the same meaning as described above.)

It is preferable that the compound represented by Formula (1) is a compound represented by Formula (1-4).

Figure 112009038838755-PAT00032

(In formula (1-4), R 41 and R 42 each independently represent a phenyl group.) The hydrogen atom contained in the phenyl group may be substituted with -R 26 or -SO 2 NHR 28 .

R 43 represents -SO 3 - or -SO 2 NHR 28 .

R 26 , R 28 , X and a represent the same meaning as described above.)

As a compound represented by Formula (1), the compound represented by Formula (1a)-Formula (1f) is mentioned, for example.

Figure 112009038838755-PAT00033

In (formula (1a), R b and R c are, each independently, a hydrogen atom, -SO 3 -. Represents a, -CO 2 H or -SO 2 NHR a R a represents a 2-ethylhexyl. X and a represent the same meaning as the above.)

Figure 112009038838755-PAT00034

(In Formula (1b), R b represents the same meaning as above.)

The compound represented by formula (1b) is a tautomer of the compound represented by formula (1b-1).

Figure 112009038838755-PAT00035

(In Formula (1b-1), R b , X and a represent the same meaning as above.)

Figure 112009038838755-PAT00036

(Formula (at 1c) and formula (ld), R d, R e and R f are, each independently, -SO 3 -. Represents a, -SO 3 Na or -SO 2 NHR a R a is 2- Ethylhexyl.)

Figure 112009038838755-PAT00037

In (formula (1e) and formula (1f), R g, R h and R i are, each independently, a hydrogen atom, -SO 3 -. Represents a, -SO 3 H or -SO 2 NHR a R a is , 2-ethylhexyl.)

The compound represented by Formula (1) is, for example, chlorinated a dye or a dye intermediate having -SO 3 H by the usual method, and a dye or dye intermediate having -SO 2 Cl obtained is R 8 -NH. It can manufacture by reacting with the amine represented by 2 . Moreover, the pigment | dye manufactured by the method as described in the upper right column to the lower left column of Unexamined-Japanese-Patent No. 3-78702 can be manufactured by making it react with an amine after chlorination similarly to the above.

The coloring agent (A) is a coloring agent which further contains an organic pigment in addition to the dye (1). As an organic pigment, specifically, for example,

C.I. Blue pigments such as Pigment Blue 15, 15: 3, 15: 4, 15: 6, and 60;

C.I. Violet pigments, such as pigment violet 1, 19, 23, 29, 32, 36, 38, etc. are mentioned. Among them, C.I. Pigment Red Violet 23, C.I. Pigment Blue 15: 3 and 15: 6 preferably contain at least one pigment selected from C.I. It is particularly preferable to contain Pigment Blue 15: 6. You may use these pigments individually or in mixture of 2 or more types.

Organic pigments in the above-mentioned pigments, if necessary, surface treatment with a rosin treatment, a pigment derivative in which an acidic group or a basic group is introduced, graft treatment on the pigment surface by a polymer compound, atomization treatment by a sulfate atomization method, etc., Alternatively, a washing treatment with an organic solvent or water for removing impurities, or a removal treatment by an ion exchange method of ionic impurities, or the like may be performed.

It is preferable that an organic pigment is uniform particle diameter. The pigment dispersion liquid of the state in which the pigment was disperse | distributed uniformly in the solution by containing a pigment dispersant and performing a dispersion process can be obtained.

As said pigment dispersant, surfactant, such as a cationic type, an anionic type, a nonionic type, an amphoteric, a polyester type, a polyamine type, an acryl type, etc. are mentioned, for example, It is used combining two or more types also independently. You may also do it.

When using a pigment dispersant, the usage-amount is per mass part of pigment (A), Preferably it is 1 mass part or less, More preferably, it is 0.05 mass part or more and 0.5 mass part or less. When the usage-amount of a pigment dispersant exists in the said range, since the pigment dispersion liquid of a uniform dispersion state tends to be obtained, it is preferable.

Content of a coloring agent (A) is mass fraction with respect to solid content in colored photosensitive resin composition, Preferably it is 5-60 mass%, More preferably, it is 8-55 mass%, More preferably, it is 10-50 mass% to be. Here, solid content means the sum total of the component remove | excluding the solvent in colored photosensitive resin composition.

When content of a coloring agent (A) exists in the said range, since the color concentration at the time of using a color filter is sufficient, and since a required amount of binder polymer can be contained in a composition, since a pattern with sufficient mechanical strength can be formed, it is preferable. .

The content of the dye (1) in the colorant (A) is usually 3 to 80% by mass ratio, preferably 3 to 70 mass%, and more preferably 3 to 50 mass%.

The content of the organic pigment in the colorant (A) is usually 20 to 97% by mass ratio, preferably 30 to 97 mass%, and more preferably 50 to 97 mass%.

Especially C.I. It is preferable that mass ratio of pigment blue 15: 6 and dye (1) is 97: 3-50: 50.

When content of the organic pigment in a coloring agent (A) exists in the said range, it is preferable because it is easy to optimize transmission spectrum, and in order to obtain high contrast and high brightness, and also it is favorable in heat resistance and chemical resistance.

The colored photosensitive resin composition used for manufacture of the color filter of this invention contains binder resin (B). Said binder resin (B), Preferably, it contains the structural unit guide | induced from (meth) acrylic acid. Here, (meth) acrylic acid represents acrylic acid and / or methacrylic acid. The content of the structural unit derived from the above-mentioned (meth) acrylic acid is, in the molar fraction, of the precursor units constituting the binder resin (B), preferably 16 mol% or more and 40 mol% or less, more preferably 18 mol% 38 mol% or more. When content of the structural unit derived from (meth) acrylic acid exists in the said range, since the solubility of a non-pixel part is favorable at the time of image development, and there exists a tendency for a residue to hardly remain in the non-pixel part after image development, it is preferable.

As another monomer which guide | induces the structural unit of binder resin other than the structural unit derived from (meth) acrylic acid, For example, an aromatic vinyl compound, unsaturated carboxylic acid ester, unsaturated carboxylic acid aminoalkyl ester, unsaturated carboxylic acid glycidyl Macromonomers having monoacryloyl groups or monomethacryloyl groups at the ends of the ester, carboxylic acid vinyl esters, unsaturated ethers, vinyl cyanide compounds, unsaturated amides, unsaturated imides, aliphatic conjugated dienes, and polymer molecular chains And the unit represented by formula (II) and the unit represented by formula (III).

Figure 112009038838755-PAT00038

(In formula (II) and formula (III), R 53 and R 55 each independently represent a hydrogen atom or a methyl group. R 54 and R 56 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Is displayed.)

Specifically as said binder resin, methacrylic acid / benzyl methacrylate copolymer, methacrylic acid / benzyl methacrylate / styrene copolymer, methacrylic acid / benzyl methacrylate / isobornyl methacrylate copolymer , Methacrylic acid / styrene / benzyl methacrylate / N-phenylmaleimide copolymer, methacrylic acid / components represented by formula (II) (wherein in formula (II), R 53 represents a methyl group, R 54 represents a hydrogen atom.) / Benzyl methacrylate copolymer, a component represented by formula (II) (wherein in formula (II), R 53 represents a methyl group and R 54 represents a hydrogen atom) .) / Benzyl methacrylate copolymer, methacrylic acid / components represented by formula (III) (wherein, in formula (III), R 55 represents a methyl group and R 56 represents a hydrogen atom.) / Styrene copolymer / tricyclodecanyl methacrylate ball Polymers and the like are preferred.

The acid value of binder resin (B) used by this invention is 50-150 normally, Preferably it is 60-135, Especially preferably, it is 70-135. When the acid value is in the above-described range, the solubility in the developer is improved, the unexposed portion is easily dissolved, and the sensitivity is increased, so that the pattern of the exposed portion remains during development, and the residual film ratio tends to be improved, which is preferable. The acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the acrylic acid polymer, and can usually be obtained by titration using an aqueous potassium hydroxide solution.

Content of binder resin (B) is 7-65 mass% normally with respect to solid content of colored photosensitive resin composition, Preferably it is 13-60 mass%, More preferably, it is 17-55 mass%. . When content of binder resin (B) exists in the said range, a pattern can be formed and it is preferable in the tendency for the resolution and residual film rate to improve.

In the formula has a composition represented by (II) the binder resin, for example, methacrylic composition represented by the acid / formula (II) (however, in this case, formula (II), R 53 is methyl, R 54 is Hydrogen atom.) / Benzyl methacrylate copolymer is obtained by polymerizing methacrylic acid and benzyl methacrylate to obtain a bicomponent polymer, wherein the resulting bicomponent polymer is represented by formula (IV) (wherein In IV), R 57 represents a hydrogen atom.

Figure 112009038838755-PAT00039

Methacrylic acid / constituent represented by formula (III) (However, in formula (III), R 55 represents a methyl group and R 56 represents a hydrogen atom.) / Styrene copolymer / tricyclodecanylmethacryl The rate copolymer can be obtained by reacting glycidyl methacrylate with a monomethacrylate copolymer of benzyl methacrylate, methacrylic acid, or tricyclodecane skeleton.

The polystyrene reduced weight average molecular weight of binder resin is 5,000-35,000 normally, Preferably it is 6,000-30,000, Especially preferably, it is 7,000-28,000. When the molecular weight is in the above-described range, the coating film hardness is improved, the residual film ratio is also high, solubility in the developer of the unexposed part is good, and the resolution tends to be improved, which is preferable.

Especially binder resin (B) represented by Formula (V) is preferable at the point of sclerosis | hardenability and developability.

Figure 112009038838755-PAT00040

Copolymerization is generally performed in a solvent using a polymerization initiator. As the polymerization initiator, for example, an azo compound such as 2,2'-azobisisobutylonitrile or 2,2'-azobis (methyl 2-methylpropionate), a peroxide such as benzoyl peroxide or tert-butyl peroxide Etc. are used. Moreover, what is necessary is just to melt | dissolve each monomer, and a solvent, for example, glycol ether esters, such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, a propylene glycol monomethyl ether acetate, a propylene glycol monoethyl ether acetate, etc. This is used. What is necessary is just to determine reaction temperature in consideration of the decomposition temperature of a polymerization initiator, the boiling point of a solvent, a monomer, etc. In addition, the side chain of the copolymer obtained in this way can be modified into the compound which has a polymeric group, and can also be set as photosensitive binder resin (B). At this time, a catalyst for introducing a polymerizable group into the resin may be added. As a catalyst, tris dimethylamino methyl phenol is mentioned, for example. Moreover, you may add the additive for preventing a side reaction. As an additive, hydroquinone is mentioned, for example.

The coloring photosensitive resin composition of this invention contains a photopolymerizable compound (C). A photopolymerizable compound (C) is a compound which can superpose | polymerize by active radical, an acid, etc. which generate | occur | produced by photoinitiator (D) by irradiating light, For example, the compound which has a polymerizable carbon-carbon unsaturated bond, etc. is mentioned. Can be mentioned.

As said photopolymerizable compound (C), it is preferable that it is a trifunctional or more than polyfunctional photopolymerizable compound. As a trifunctional or more than polyfunctional photopolymerizable compound, pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol pentamethacrylate, dipentaerythritol hexaacrylate, Dipentaerythritol hexamethacrylate and the like. Said photopolymerizable compound (C) may be used individually or in combination of 2 or more types, It is preferable that the content is 7-65 mass% by mass fraction with respect to solid content of a coloring photosensitive resin composition, Furthermore, Preferably it is 13-60 mass%, More preferably, it is 17-55 mass%. When content of said photopolymerizable compound (C) exists in the said range, since hardening will fully occur and the film thickness ratio before and behind image development will improve, it will become difficult to undercut into a pattern, and adhesiveness tends to become favorable, and it is preferable. Do.

The coloring photosensitive resin composition of this invention contains a photoinitiator (D). As said photoinitiator (D), an acetophenone type compound, an active radical generator, an acid generator, etc. are mentioned.

As said acetophenone type compound, diethoxy acetophenone, 2-methyl- 2-morpholino-1- (4-methylthio phenyl) propane- 1-one, 2-hydroxy-2- methyl, for example. -1-phenylpropane-1-one, benzyldimethyl ketal, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl] propan-1-one, 1-hydroxycyclo And an oligomer of hexylphenyl ketone, 2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl] propane-1-one, and the like, and preferably 2-methyl-2-morpholine. No-1- (4-methylthiophenyl) propan-1-one and the like.

Active radical generators generate active radicals by being irradiated with light. As said active radical generator, a benzoin type compound, a benzophenone type compound, a thioxanthone type compound, a triazine type compound, an oxime type compound etc. are mentioned, for example.

As said benzoin type compound, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, etc. are mentioned, for example.

As said benzophenone type compound, benzophenone, methyl o-benzoyl benzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3 ', 4,4'- Tetra (tert-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone, and the like.

As said thioxanthone type compound, 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2, 4- diethyl thioxanthone, 2, 4- dichloro thioxanthone, 1-chloro, for example 4-propoxy city oxanthone etc. are mentioned.

As said triazine type compound, 2, 4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1, 3, 5- triazine, 2, 4-bis (trichloromethyl ) -6- (4-methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxystyryl) -1,3,5- Triazine, 2,4-bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloro Methyl) -6- [2- (furan-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino -2-methylphenyl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3 , 5-triazine and the like.

As said oxime type compound, an O-acyl oxime type compound is mentioned, for example, As a specific example, 1- (4-phenylsulfanylphenyl) -butane-1,2-dione 2-oxime-O- Benzoate, 1- (4-phenylsulfanylphenyl) -octane-1,2-dione 2-oxime-O-benzoate, 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazole -3-yl] ethanone 1-O-acetate, 1- [9-ethyl-6- (2-methyl-4- (3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy) benzoyl)- 9H-carbazol-3-yl] ethanone 1-0-acetate.

As active radical generators other than the above examples, for example, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,2'-bis (o-chlorophenyl) -4,4 ', 5,5 '-Tetraphenyl-1,2'-biimidazole, 10-butyl-2-chloroacridone, 2-ethylanthraquinone, benzyl, 9,10-phenansrenquinone, camphorquinone, methyl phenylglyoxylate, Titanocene compound etc. can also be used.

As said acid generator, 4-hydroxyphenyl dimethyl sulfonium p-toluene sulfonate, 4-hydroxyphenyl dimethyl sulfonium hexafluoro antimonate, 4-acetoxy phenyl dimethyl sulfonium-p-, for example Toluenesulfonate, 4-acetoxyphenylmethyl benzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyl iodonium p-toluene Onium salts, such as a sulfonate and diphenyl iodonium hexafluoro antimonate, nitrobenzyl tosylates, benzoin tosylate, etc. are mentioned.

In addition, among the compounds described above as the active radical generators, there are also compounds which generate an acid simultaneously with the active radicals. For example, a triazine-based photopolymerization initiator is also used as a scattering agent.

Content of a photoinitiator (D) is mass fraction with respect to the total amount of binder resin (B) and a photopolymerizable compound (C), Preferably it is 0.1-30 mass%, More preferably, it is 1-20 mass%. When content of a photoinitiator exists in the said range, it becomes preferable because it becomes high sensitivity, shortens an exposure time, and improves productivity.

The photopolymerization initiator adjuvant (F) may further be contained in the coloring photosensitive resin composition of this invention. A photoinitiator (F) is normally used in combination with a photoinitiator (D), and is a compound used in order to accelerate superposition | polymerization of the photopolymerizable compound in which superposition | polymerization started with a photoinitiator.

Examples of the photopolymerization initiator (F) include an amine compound, an alkoxy anthracene compound, a thioxanthone compound, and the like.

As said amine type compound, triethanolamine, methyl diethanolamine, triisopropanolamine, 4-dimethylamino benzoate, 4-dimethylamino benzoate ethyl, 4-dimethylamino isoamyl benzoate, 2-dimethylamino benzoic acid, for example. Ethyl, 4-dimethylamino benzoic acid 2-ethylhexyl, N, N-dimethylparatoluidine, 4,4'-bis (dimethylamino) benzophenone (typically mihiraketone), 4,4'-bis (diethylamino ) Benzophenone, 4,4'-bis (ethylmethylamino) benzophenone, etc. are mentioned, Especially, 4,4'-bis (diethylamino) benzophenone is preferable.

As said alkoxy anthracene type compound, 9,10- dimethoxy anthracene, 2-ethyl-9,10- dimethoxy anthracene, 9,10- diethoxy anthracene, 2-ethyl-9, 10- diethoxyan Trasene, 9,10-dibutoxy anthracene, 2-ethyl-9,10-dibutoxy anthracene, etc. are mentioned.

As said thioxanthone type compound, 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2, 4- diethyl thioxanthone, 2, 4- dichloro thioxanthone, 1-chloro- 4-propoxy city oxanthone etc. are mentioned.

You may use photoinitiator (F) individually or in combination of 2 or more types. Moreover, a commercially available thing can also be used as a photoinitiator adjuvant (F), As a commercially available photoinitiator (F), brand name "EAB-F" (made by Hodogaya Chemical Co., Ltd.) etc. is mentioned, for example. Can be.

As a combination of the photoinitiator (D) and the photoinitiator (F) in the coloring photosensitive resin composition of this invention, diethoxy acetophenone / 4,4'-bis (diethylamino) benzophenone, 2- Methyl-2-morpholino-1- (4-methylthiophenyl) propane-1-one / 4,4'-bis (diethylamino) benzophenone, 2-hydroxy-2-methyl-1-phenylpropane -1-one / 4,4'-bis (diethylamino) benzophenone, benzyldimethyl ketal / 4,4'-bis (diethylamino) benzophenone, 2-hydroxy-2-methyl-1- [4 -(2-hydroxyethoxy) phenyl] propane-1-one / 4,4'-bis (diethylamino) benzophenone, 1-hydroxycyclohexylphenylketone / 4,4'-bis (diethylamino ) Benzophenone, oligomer / 4,4'-bis (diethylamino) benzophenone of 2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl] propan-1-one Benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one / 4,4'-bis (diethylamino) benzophenone and the like, and preferably 2-methyl-2-morpholino-1- (4-methylthiophenyl) propan-1-one / 4,4-bis (diethylamino) benzophenone may be mentioned.

When using these photoinitiators (F), the usage-amount is per mol of photoinitiators (D), Preferably it is 0.01-10 mol, More preferably, it is 0.01-5 mol.

The coloring photosensitive resin composition of this invention contains a solvent (E). Examples of the solvent (E) include ethers, aromatic hydrocarbons, ketones other than the above, alcohols, esters, amides, N-methylpyrrolidone, and dimethyl sulfoxide.

Examples of the ethers include tetrahydrofuran, tetrahydropyran, 1,4-dioxane, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether and diethylene glycol. Monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl Ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methyl cellosolve acetate, ethyl cellosolve acetate, ethyl carbitol acetate, butyl carbitol acetate, anisole, phentol And methylanisole There.

As said aromatic hydrocarbons, benzene, toluene, xylene, mesitylene, etc. are mentioned, for example.

As said ketones, for example, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, 4-hydroxy-4-methyl-2- Pentanone, cyclopentanone, cyclohexanone, etc. are mentioned.

As said alcohol, methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, glycerin, etc. are mentioned, for example.

Examples of the esters include ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoam acetate, isobutyl acetate, butyl propionate, isopropyl acetate, ethyl butyrate, butyl butyrate and alkyl esters. , Methyl lactate, ethyl lactate, methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate, methyl methoxyacetate, ethyl methoxyacetate, butyl acetate, ethoxyacetic acid, ethyl ethoxyacetate, methyl 3-oxypropionate, Ethyl 3-oxypropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-oxypropionate, ethyl 2-oxypropionate, 2-oxypropionic acid In propyl, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-epoxypropionate, 2-ethoxypropionic acid , Methyl 2-oxy-2-methylpropionate, ethyl 2-oxy-2-methylpropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, methyl pyruvate, pyrubin Ethyl acid, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, methyl 2-oxobutyrate, ethyl 2-oxobutyrate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate and γ- Butyrolactone etc. are mentioned.

As said amides, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, etc. are mentioned, for example.

Among these, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, and 4-hydroxy-4-methyl-2-pentanone are preferable, and it is more preferable to use these together.

In addition, said solvent may be used individually or in combination of 2 or more types.

Content of the solvent (E) in a coloring photosensitive resin composition is a mass fraction with respect to a coloring photosensitive resin composition, Preferably it is 70-95 mass%, More preferably, it is 75-90 mass%. When content of a solvent (E) exists in the said range, since flatness at the time of application | coating becomes favorable and color density does not run short when a color filter is formed, it is preferable because there exists a tendency for favorable display characteristics.

Surfactant (G) may be further contained in the coloring photosensitive resin composition of this invention. As surfactant (G), at least 1 sort (s) chosen from the group which consists of a silicone type surfactant, a fluorine type surfactant, and a silicone type surfactant which has a fluorine atom is mentioned.

As said silicone type surfactant, surfactant etc. which have a siloxane bond are mentioned. Specifically, toray silicon DC3PA, toray silicon SH7PA, toray silicon DC11PA, toray silicon SH21PA, toray silicon SH28PA, toray silicon 29SHPA, toray silicon SH30PA, polyether modified silicone oil SH8400 (brand name: Toray silicon Co., Ltd. product), KP321 , KP322, KP323, KP324, KP326, KP340, KP341 (made in Shin-Etsu Silicone), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460 (Momental Performance Japan Joint Company) ), And the like.

As said fluorine-type surfactant, surfactant etc. which have a fluorocarbon chain | strand are mentioned. Specifically, fluoride FC430, fluoride FC431 (made by Sumitomo 3M), mega pack F142D, mega pack F171, mega pack F172, mega pack F173, mega pack F177, mega pack F183, mega pack R30 (Product made in DIC Corporation), F top (brand name) EF301, F top EF303, f top EF351, F top EF352 (product made by Shin-Akida Chemical Co., Ltd.), saffron (brand name) S381, saffron S382, saffron SC101 And Saffron SC105 (manufactured by Asahi Glass Co., Ltd.), E5844 (manufactured by Daikin Fine Chemical Research Institute Co., Ltd.), BM-1000, and BM-1100 (all made by BM Chemie Co., Ltd.).

As a silicone type surfactant which has the said fluorine atom, surfactant etc. which have a siloxane bond and a fluorocarbon chain | strand are mentioned. Specifically, Mega Pack (R) R08, Mega Pack BL20, Mega Pack F475, Mega Pack F477, Mega Pack F443 (manufactured by DIC Corporation), and the like.

You may use these surfactant individually or in combination of 2 or more types.

Content of surfactant (G) is a mass fraction with respect to a coloring photosensitive resin composition, Preferably it is 0.00001-0.1 mass%, More preferably, it is 0.00005-0.01 mass%. If content of surfactant (G) exists in the said range, flatness will become favorable and it is preferable.

As a method of forming the pattern of a color filter using the coloring photosensitive resin composition of this invention, the coloring photosensitive resin composition of this invention is made into the board | substrate or another resin layer (for example, the other formed on the board | substrate first). An inkjet device which is coated on a photosensitive resin composition layer, etc.), removes volatile components such as a solvent to form a colored layer, exposes the colored layer through a photomask, and develops the photolithographic method. The method of using, etc. are mentioned.

According to the coloring photosensitive resin composition of this invention, it becomes possible to obtain the coating film with high brightness.

Example

Hereinafter, the present invention will be described in more detail with reference to Examples. "%" And "part" in an example are weight% and a weight part unless there is particular notice.

Synthesis Example 1

15 parts of sulforhodamine B (manufactured by Kanto Chemical Co., Ltd.), 150 parts of chloroform and 9.8 parts of N, N-dimethylformamide were added to a flask equipped with a cooling tube and a stirring device, 12.0 parts of thionyl was dripped and added. After completion of the dropwise addition, the temperature was raised to 50 ° C, held at the same temperature for 5 hours for reaction, and then cooled to 20 ° C. The mixture solution of 13.9 parts of 2-ethylhexylamine and 24.5 parts of triethylamines was dripped and added, maintaining the reaction solution after cooling at 20 degrees C or less under stirring. Thereafter, the reaction was stirred at the same temperature for 5 hours. Subsequently, the solvent was distilled off from the reaction mixture by a rotary evaporator, and then a small amount of methanol was added thereto, followed by vigorous stirring. This mixture was added to the liquid mixture of 375 parts of ion-exchange water, stirring, and the crystal | crystallization was deposited. The precipitated crystals were filtered off, washed well with ion exchanged water, and dried under reduced pressure at 60 ° C to obtain 14.7 parts of dye Al.

Figure 112009038838755-PAT00041

                             A1

Synthesis Example 2

Into a flask equipped with a cooling tube and a stirring device, 15 parts of a pigment (a main catalytic agent) represented by Formula A0-2, 150 parts of chloroform, and 7.1 parts of N, N-dimethylformamide were charged and kept at 20 ° C. or lower under stirring. In addition, 8.7 parts of thionyl chlorides were dripped and added. After completion of the dropwise addition, the temperature was raised to 50 ° C, held at the same temperature for 5 hours for reaction, and then cooled to 20 ° C. A mixture of 10 parts of 2-ethylhexyl amine and 17.7 parts of triethylamine was added dropwise while maintaining the reaction solution after cooling at 20 ° C. or less under stirring. Thereafter, the reaction was stirred at the same temperature for 5 hours. Subsequently, the solvent was distilled off from the reaction mixture by a rotary evaporator, and then a small amount of methanol was added thereto, followed by vigorous stirring. This mixture was added to the liquid mixture of 375 parts of ion-exchange water, stirring, and the crystal | crystallization was deposited. Precipitated crystals were filtered off, washed well with ion-exchanged water, and dried under reduced pressure at 60 ° C to obtain 12.7 parts of dye A2 (mixed dyes of dyes A2-1 to Dye A2-7).

Figure 112009038838755-PAT00042

(In formula (A2), R d , R e and R f each independently represent —SO 3 — , —SO 3 Na or —SO 2 NHR a . R a represents 2-ethylhexyl. )

Figure 112009038838755-PAT00043

Synthesis Example 3

Into a flask equipped with a cooling tube and a stirring device, 15 parts of a pigment (a main catalytic agent) represented by Formula A0-3, 150 parts of chloroform, and 8.9 parts of N, N-dimethylformamide were charged and stirred to maintain 20 ° C. or less. 10.9 parts of thionyl chlorides were dripped, and it added, adding. After completion of the dropwise addition, the temperature was raised to 50 ° C, held at the same temperature for 5 hours for reaction, and then cooled to 20 ° C. A mixture of 12.5 parts of 2-ethylhexylamine and 22.1 parts of triethylamine was added dropwise while maintaining the reaction solution after cooling at 20 ° C. or lower under stirring. Thereafter, the reaction was stirred at the same temperature for 5 hours. Subsequently, the solvent was distilled off from the reaction mixture by a rotary evaporator, and then a small amount of methanol was added thereto, followed by vigorous stirring. This mixture was added to the liquid mixture of 375 parts of ion-exchange water, stirring, and the crystal | crystallization was deposited. Precipitated crystals were filtered off, washed well with ion-exchanged water, and dried under reduced pressure at 60 ° C to obtain 11.3 parts of dye A3 (mixed dyes of dyes A3-1 to Dye A3-8).

Figure 112009038838755-PAT00044

In (formula (A3), R g, R h and R i are, each independently, a hydrogen atom, -SO 3 -. Represents a, -SO 3 H or -SO 2 NHR a R a is 2-ethylhexyl Indicates.)

Figure 112009038838755-PAT00045

Synthesis Example 4

182 g of propylene glycol monomethyl ether acetate was introduced into a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping lot, and a nitrogen inlet tube, and the atmosphere in the flask was changed from air to nitrogen. 70.5 g (0.40 mol) of methacrylate, 43.0 g (0.5 mol) of methacrylic acid, 22.0 g (0.10 mol) of monomethacrylate (FA-513M by Hitachi Chemical Co., Ltd.) of a tricyclodecane skeleton, and propylene glycol monomethyl The solution which added 3.6 g of 2,2'- azobisisobutylonitrile was dripped at the mixture which consists of 136 g of ether acetates, and it stirred at 100 degreeC again. Next, the atmosphere in the flask was changed from nitrogen to air, and 35.5 g [0.25 mol of glycidyl methacrylate ((50 mol% of the carboxyl groups of methacrylic acid used in this reaction)]] and 0.9 g of trisdimethylaminomethylphenol And 0.145 g of hydroquinone were charged into a flask, and the reaction was continued at 110 ° C to obtain a resin solution B1 having a solid dispersion value of 79 mgKOH / g. The weight average molecular weight of polystyrene conversion measured by GPC was 30,000.

About the measurement of the polystyrene conversion weight average molecular weight of said resin, it carried out on condition of the following using GPC method.

Device ; HLC-8120 GPC (manufactured by Tosoh Corporation)

column ; TSK-GELG2000HXL

Column temperature; 40 ℃

Solvent; THF

Flow rate; 1.0 mL / min

Test liquid solids concentration; 0.001-0.01 mass%

Injection volume: 50 μL

Detector; RI

Calibration standard; TSK STANDARD POLYSTYRENE F-40, F-4, F-1, A-2500, A-500 (made by Tosoh Corporation)

Example 1

[Preparation of Colored Photosensitive Resin Composition 1]

(A) Colorant: C.I. Pigment Blue 15: 6 20 parts

Acrylic pigment dispersant part 5

Propylene glycol monomethyl ether acetate 137 parts

Were mixed, the pigment was sufficiently dispersed using a bead mill, and then

(A) colorant: dye A1 3.5 parts

(B) Resin: Resin Solution B1 157 parts

(C) Photopolymerizable Compound: dipentaerythritol hexaacrylate

(Nihon Kayaku Co., Ltd.) 50 copies

(D) Photoinitiator: OXE-01

(Product made in Chiba specialty chemical company) 15 copies

(E) Solvent: 289 parts of 4-hydroxy-4-methyl-2-pentanone

Was mixed and the coloring photosensitive resin composition 1 was obtained.

[Formation of Pattern]

The colored photosensitive resin composition 1 was apply | coated by the spin coat method on the 2-inch angle glass substrate (Eagle 2000: Corning company make), and it prebaked at 100 degreeC for 3 minutes. After cooling, the gap between the substrate coated with the coloring photosensitive resin composition and the quartz glass photomask having the pattern was set to 100 µm, and the exposure atmosphere (TME-150 RSK; manufactured by Topcon Co., Ltd.) was used. The light was irradiated with an exposure dose (365 nm standard) of mJ / cm 2. After light irradiation, the coating film was immersed in an aqueous developer containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 23 ° C. for 80 seconds. After washing with water, post-baking was carried out at 220 ° C. for 20 minutes in an oven. It was. It was 2.2 micrometers when the film thickness of the obtained hardening pattern after cooling was measured using the film thickness measuring apparatus (DEKTAK3; Japan Vacuum Technology Co., Ltd.).

[evaluation]

Spectrophotometry was measured with a colorimeter (OSP-SP-200; manufactured by Olympus Co., Ltd.) for the coated film on the obtained glass substrate, and the xy chromaticity coordinates (Bx, By in the CXY XYZ colorimeter using a C light source). ) And brightness. The results are shown in Table 1.

Examples 2-5

A colored photosensitive resin composition and a coating film were obtained in the same manner as in Example 1 except that the dye A1 was changed to the dye shown in Table 1. The results are shown in Table 1.

Example 1 Example 2 Example 3 Example 4 Example 5 dyes A1 A2 A3 A4 ※ A5 ※ Bx 0.141 0.138 0.141 0.141 0.141 By 0.085 0.085 0.085 0.085 0.085 brightness 9.7 9.7 9.7 9.6 9.5

※ Dye A4: Rhodamine B (made by Taoka Chemical)

Figure 112009038838755-PAT00046

Dye A5: Rhodamine B Base (Aldrich)

Figure 112009038838755-PAT00047

High brightness was confirmed by the coating film formed using the coloring photosensitive resin composition of Examples 1-5.

According to the present invention, a high brightness coating film and color filter can be obtained. The obtained color filter is used suitably for a liquid crystal display element or a solid-state image sensor.

Claims (10)

In the coloring photosensitive resin composition containing a coloring agent (A), binder resin (B), a photopolymerizable compound (C), a photoinitiator (D), and a solvent (E), The coloring photosensitive resin composition whose coloring agent (A) is a coloring agent containing the organic solvent soluble dye containing the compound represented by Formula (1), and an organic pigment.
Figure 112009038838755-PAT00048
 In (formula (1), R 1 ~R 4 each independently represents an aromatic hydrocarbon group of a hydrogen atom, -R 6, or 6 to 10 carbon atoms, hydrogen atoms contained in the carbon number of 6 to 10 aromatic hydrocarbon groups are, a halogen atom, -R 6, -OH, -OR 6 , -SO 3 -, -SO 3 H, -SO 3 M, -CO 2 H, -CO 2 R 6, -SO 3 R 6, -SO 2 NHR 8 or —SO 2 NR 8 R 9 may be substituted. R 5 is, -SO 3 -, -SO 3 H , -SO 3 M, -CO 2 H, -CO 2 R 6, a -SO 3 R 6, -SO 2 NHR 8 or -SO 2 NR 8 R 9 Indicates. m represents the integer of 0-5. When m is an integer of 2 or more, some R <5> may be same or different. X represents a halogen atom. a represents the integer of 0 or 1. R <6> represents a C1-C10 saturated hydrocarbon group. The hydrogen atom contained in the C1-C10 saturated hydrocarbon group may be substituted with the halogen atom. The methylene group contained in the C1-C10 saturated hydrocarbon group may be substituted with an oxygen atom, a carbonyl group or -NR 6- . R 8 and R 9 each independently represent a linear or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or -Q. Alternatively, R 8 and R 9 may be bonded to each other to form a heterocyclic ring having 1 to 10 carbon atoms. Q represents an aromatic hydrocarbon group having 6 to 10 carbon atoms or an aromatic heterocyclic group having 5 to 10 carbon atoms, and the hydrogen atoms contained in the aromatic hydrocarbon group and the aromatic heterocyclic group include -OH, R 6 , -OR 6 , -NO 2 , -CH = CH 2 , -CH = CHR 6 or a halogen atom may be substituted. Hydrogen atoms contained in the cycloalkyl group of 1 to 10 carbon atoms and straight-chain or branched alkyl group having a carbon number of 3 to 30 of the, hydroxyl group, may be substituted with a halogen atom, -Q, -CH = CH 2 or -CH = CHR 6. The methylene group contained in a linear or branched alkyl group having 1 to 10 carbon atoms and a cycloalkyl group having 3 to 30 carbon atoms may be substituted with an oxygen atom, a carbonyl group, or -NR 6- , The hydrogen atom contained in a C1-C10 heterocycle may be substituted by R <6> , -OH or -Q. M represents a sodium atom or a potassium atom.) The method of claim 1, The coloring photosensitive resin composition whose compound represented by Formula (1) is a compound represented by Formula (1-1).
Figure 112009038838755-PAT00049
 (In formula (1-1), R <11> -R <14> represents a hydrogen atom, -R <6>, or a C6-C10 aromatic hydrocarbon group each independently. Hydrogen atom contained in the said C6-C10 aromatic hydrocarbon group. is a halogen atom, -R 6, -OH, -OR 6 , -SO 3 -, -SO 3 H, -SO 3 Na, -CO 2 H, -CO 2 R 6, -SO 3 R 6, -SO It may be substituted by 2 NHR 8 or -SO 2 NR 8 R 9 . R 15 is a hydrogen atom, -SO 3 -, -SO 3 H , -SO 2 NHR 8 or -SO 2 represents an NR 8 R 9. R 16 represents —SO 3 — , —SO 3 H, —SO 2 NHR 8, or —SO 2 NR 8 R 9 . R 6 , R 8 , R 9 , m, X and a represent the same meaning as described above.) The method of claim 1, The coloring photosensitive resin composition whose compound represented by Formula (1) is a compound represented by Formula (1-2).
Figure 112009038838755-PAT00050
 In (formula (1-2), R 21 ~R 24 each independently represents an aromatic hydrocarbon group of a hydrogen atom, -R 26, or 6 to 10 carbon atoms, hydrogen atoms contained in the carbon number of 6 to 10 aromatic hydrocarbon groups It is a halogen atom, -R 26, -OH, -OR 26 , -SO 3 -, -SO 3 Na, -CO 2 H, -CO 2 R 26, -SO 3 H, -SO 3 R 26 or -SO 2 NHR 28 may be substituted. R 25 represents —SO 3 — , —SO 3 Na, —CO 2 H, —CO 2 R 26 , —SO 3 H or SO 2 NHR 28 . R <26> represents a C1-C10 saturated hydrocarbon group. The hydrogen atom contained in the said C1-C10 saturated hydrocarbon group may be substituted by -OR <26> or a halogen atom. R 28 represents a hydrogen atom, -R 26 , -CO 2 R 26 or a C6-C10 aromatic hydrocarbon group, and the hydrogen atom contained in the C6-C10 aromatic hydrocarbon group is -R 26 or -OR 26 It may be substituted. m, X, and a represent the same meaning as the above.) The method according to any one of claims 1 to 3, The coloring photosensitive resin composition whose compound represented by Formula (1) is a compound represented by Formula (1-3).
Figure 112009038838755-PAT00051
 (In formula (1-3) in, R 31 and R 32 each independently represents a phenyl group. A hydrogen atom contained in the phenyl group, a halogen atom, -R 26, -OR 26, -CO 2 R 26, It may be substituted by -SO 3 R 26 or -SO 2 NHR 28 . R 33 represents -SO 3 - or -SO 2 NHR 28 . R 34 represents a hydrogen atom, -SO 3 - or -SO 2 NHR 28 . R 26 , R 28 , X and a represent the same meaning as described above.) The method according to any one of claims 1 to 3, The coloring photosensitive resin composition whose compound represented by Formula (1) is a compound represented by Formula (1-4).
Figure 112009038838755-PAT00052
 (In formula (1-4), R 41 and R 42 each independently represent a phenyl group.) The hydrogen atom contained in the phenyl group may be substituted with -R 26 or -SO 2 NHR 28 . R 43 represents -SO 3 - or -SO 2 NHR 28 . R 26 , R 28 , X and a represent the same meaning as described above.) The method according to any one of claims 1 to 3, Organic pigments, C.I. Colored photosensitive resin composition which is an organic pigment containing pigment blue 15: 6. The method of claim 6, C.I. in colorants (A). Colored photosensitive resin composition whose mass ratio with pigment blue 15: 6 and the organic-solvent soluble dye containing the compound represented by Formula (1) is 97: 3-50: 50. The coating film formed using the coloring photosensitive resin composition of any one of Claims 1-3. The color filter formed using the coloring photosensitive resin composition of any one of Claims 1-3. The method of claim 9, A color filter formed by the photolithographic method.
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CN105652596A (en) 2016-06-08
TWI450033B (en) 2014-08-21

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