WO2012036085A1 - Composition de résine colorée - Google Patents

Composition de résine colorée Download PDF

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Publication number
WO2012036085A1
WO2012036085A1 PCT/JP2011/070600 JP2011070600W WO2012036085A1 WO 2012036085 A1 WO2012036085 A1 WO 2012036085A1 JP 2011070600 W JP2011070600 W JP 2011070600W WO 2012036085 A1 WO2012036085 A1 WO 2012036085A1
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WIPO (PCT)
Prior art keywords
group
acrylate
resin composition
meth
color filter
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PCT/JP2011/070600
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English (en)
Japanese (ja)
Inventor
聡 小林
諒 寺西
秀洋 新井
石井　裕
高明 倉田
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日本化薬株式会社
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Priority to KR1020127000325A priority Critical patent/KR20130115076A/ko
Priority to JP2011552106A priority patent/JP5856848B2/ja
Publication of WO2012036085A1 publication Critical patent/WO2012036085A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0025—Crosslinking or vulcanising agents; including accelerators
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0091—Complexes with metal-heteroatom-bonds
    • 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
    • C09B11/02—Diaryl- or thriarylmethane dyes derived from diarylmethanes
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/201—Filters in the form of arrays
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509—Filters, e.g. light shielding masks
    • G02F1/133514—Colour filters
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/30—Devices specially adapted for multicolour light emission
    • H10K59/38—Devices specially adapted for multicolour light emission comprising colour filters or colour changing media [CCM]

Definitions

  • the present invention relates to a colored resin composition for forming a blue pixel, a color filter formed using the same, a liquid crystal display device formed using the color filter, an image sensor (CCD, CMOS), an organic EL display, and the like
  • the present invention relates to an electronic display device.
  • liquid crystal display elements such as liquid crystal displays (LCD) typified by notebook computers, liquid crystal televisions, mobile phones, etc., and image sensors (CCD, CMOS) used as input devices for digital cameras, color copiers, etc.
  • a color filter is required.
  • As a method for producing a color filter used in these liquid crystal display devices and solid-state image sensors there are a dyeing method, an electrodeposition method, a printing method, a pigment dispersion method, and the like. In recent years, the pigment dispersion method has become the mainstream.
  • a patterning method a photolithography method is typical, and a color filter is formed using a mixture of a photosensitive resin composition and a pigment dispersion.
  • a method of forming a color filter by applying a colored ink directly on a substrate without using a mask by an ink jet printer is also performed.
  • Improvement of color purity, saturation, brightness, and contrast, which are characteristics required for color filters, is particularly important.
  • the amount of light of the backlight can be suppressed and the power consumption can be reduced, so this is an environmentally necessary technology.
  • In order to improve the color purity of the color filter it is necessary to increase the content of the color pigment or to select a pigment having a better spectral waveform.
  • the pigment concentration must be reduced or the film thickness must be reduced. In order to achieve both of these contradictory characteristics, a method of making pigment fine particles has been performed. As micronization progresses, there is a limit to the resistance and dispersion stability, and even when the brightness is improved, the compatibility of resistance is not achieved.
  • phthalocyanine dyes are known to be excellent in resistance (Patent Document 3), their color characteristics are not blue, and since they are generally reddish cyan, a clear blue pixel cannot be formed.
  • a colored resin composition that includes a clear blue pixel and a highly durable color material that is highly reliable in a color filter, but is currently in practical use. Therefore, there is a need for a high-quality color filter that is vivid blue and excellent in durability as the next generation.
  • JP-A-8-94826 Japanese Patent Laid-Open No. 2002-14222 Japanese Patent Application Laid-Open No. 60-249102 Japanese Patent Publication No.41-2466 Japanese Patent Laid-Open No. Sho 63-172772 Japanese Patent Publication No. 50-4019 Japanese Examined Patent Publication No. 39-16787
  • An object of the present invention is to provide a blue pixel of a color filter having clear blue characteristics, excellent color characteristics such as contrast, and excellent heat resistance.
  • the present invention (1) A colored resin composition for a color filter containing a colorant compound represented by the following formula (1), a binder resin, a solvent, a photopolymerization initiator, and a curing agent.
  • R 1a to R 6a each independently represents a hydrogen atom, a C1-C30 alkyl group, a phenyl group or a benzyl group, but at least one is a C7-C30 alkyl group.
  • R 7a ⁇ R 20a each independently represent a hydrogen atom, a halogen atom, .Z represents an alkyl group of C1-C6 - alkylsulfonyl imide anion having a higher halogenated alkyl group C1-C10, alkylsulfonyl methide anion, or Represents an alkyl sulfonate).
  • Y 1 to Y 4 each independently represents a hydrogen atom, a C1-C12 alkyl group or an aryl group
  • X 1 to X 5 each independently represent a hydrogen atom, a C1-C12 alkyl group, a C1-C12 alkoxy group, a halogen atom atom, a nitro group, a phenoxy group, a carboxyl group, an alkoxycarbonyl group, a sulfo group, a sulfamoyl group, which may have one or two or more carbamoyl groups anion Z -. are the same as above).
  • a colored cured film for a color filter which is patterned using the colored resin composition according to any one of (1) to (4), (6) A color filter comprising the colored cured film for a color filter according to (5), (7) A liquid crystal display device and an organic EL display comprising the color filter according to (6), (8) A solid-state imaging device comprising the color filter according to (7), About.
  • the blue colored resin composition of the present invention has a clear blue contrast characteristic by using a colored resin composition containing a specific blue colorant compound, and has high quality for color filters having excellent heat resistance and the like. Blue pixels can be provided.
  • the blue colored resin composition of the present invention contains a binder resin, a solvent, a photopolymerization initiator, a curing agent, and a specific blue color material compound, and if necessary, a color material compound such as another pigment or dye, Various additives such as a surfactant, a thermosetting agent, a polymerization inhibitor, and an ultraviolet absorber can be contained, but are not limited to these, and there are no particular limitations as components other than the specific colorant compound Can be used.
  • the pixel manufacturing method using the colored resin composition of the present invention mainly includes a photolithography method and an inkjet method, and the former uses a photosensitive resin composition having excellent developability using a photopolymerization initiator.
  • the latter does not necessarily require a photopolymerization initiator and a thermosetting resin composition is used.
  • the C1-C30 alkyl group may be substituted or unsubstituted.
  • examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, butyl Group, 1-methylpropyl group (s-butyl group), isobutyl group, pentyl group, 1-ethylpropyl group, 1-methylbutyl group, cyclopentyl group, hexyl group, 1-methylpentyl group, 1-ethylbutyl group, cyclohexane Xyl, hydroxypropyl, 2-sulfoethyl, carboxyethyl, cyanoethyl, methoxyethyl, ethoxyethyl, butoxyethyl, trifluoromethyl, pentafluoroethyl, 2-hepty
  • At least one of R 1a ⁇ R 6a in the formula (1) is an alkyl group of C7-C30, at least one of R 5a or R 6a also in industry in R 1a ⁇ R 6a
  • One is preferably a C7-C30 alkyl group, and specific examples thereof are 2-heptyl and 2-methylcyclohexyl groups.
  • the phenyl group or benzyl group may have a substituent.
  • the substituent include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and an isobutyl group.
  • (C1-C5) alkyl group such as t-butyl group, pentyl group, halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom, sulfonic acid group, methoxy group, ethoxy group, propoxy group, butoxy group , (C1-C6) alkoxy groups such as t-butoxy group and hexyloxy group, hydroxy (C1-C5) alkyl groups such as hydroxyethyl group and hydroxypropyl group, methoxyethyl group, ethoxyethyl group, ethoxypropyl group, butoxy Hydroxy such as (C1-C5) alkoxy (C1-C5) alkyl group such as ethyl group, 2-hydroxyethoxy group (C1-C5) alkoxy group, a 2-methoxyethoxy group, 2-ethoxyethoxy group alkoxy (C1-C5) alkoxy group such as
  • examples of the halogen atom include fluorine, chlorine, bromine and iodine.
  • R 7a to R 20a in the formula (1) are preferably a hydrogen atom, a chlorine atom, or a substituted or unsubstituted C1-C6 alkyl group.
  • examples of the C1-C6 alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a pentyl group, a cyclopentyl group, a hexyl group, and a cyclohexyl group.
  • Examples include xyl group, hydroxypropyl group, 2-sulfoethyl group, carboxyethyl group, cyanoethyl group, methoxyethyl group, ethoxyethyl group, butoxyethyl group, trifluoromethyl group, pentafluoroethyl group, and the like, and methyl group is particularly preferable. .
  • Table 1-1 Specific examples of the colorant compound represented by the formula (1) are shown in Table 1-1, but the present invention is not limited thereto.
  • Table 1-1 In Table 1-1, regarding the substituent R, Me represents a methyl group, and Et represents an ethyl group. Further, when Z ⁇ is ⁇ , it represents a tristrifluoromethanesulfonylmethide anion, and when ⁇ ⁇ represents a bistrifluoromethanesulfonylimide anion.
  • R 1b to R 6b each independently represent a hydrogen atom, a halogen atom, a C1-C12 alkyl group, a C1-C12 alkoxy group, a nitro group, Represents a group, a carboxyl group or an alkoxycarbonyl group.
  • Y 1 to Y 4 each independently represent a hydrogen atom, a C1-C12 alkyl group, or an aryl group.
  • X 1 to X 5 are each independently a hydrogen atom, C1-C12 alkyl group, C1-C12 alkoxy group, halogen atom, nitro group, phenoxy group, carboxyl group, alkoxycarbonyl group, sulfo group, sulfamoyl group, carbamoyl group 1 type (s) or 2 or more types may be included.
  • Anion Z - is an alkyl sulfonyl methide anion, alkylsulfonyl imide anion or alkyl sulfonates having higher halogenated alkyl group having C1-C10.
  • alkyl group of the formula (2) examples include methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, t-butyl, iso-butyl, n-pentyl, n-hexyl, n- Examples thereof include C1-C12 alkyl groups such as octyl, 2-ethylhexyl, cyclohexyl and the like. These alkyl groups may have a substituent.
  • alkyl group having a substituent examples include a hydroxyethyl group, a hydroxypropyl group, a hydroxybutyl group, a 2-sulfoethyl group, a carboxyethyl group, a cyanoethyl group, a methoxy group, and the like. Examples thereof include an ethyl group, an ethoxyethyl group, a butoxyethyl group, a trifluoromethyl group, and a pentafluoroethyl group.
  • the substituent which the alkyl group can have includes a carbamoyl group, a carboxyl group and the like.
  • alkoxy group of the formula (2) examples include an alkoxy group having a C1-C12 alkyl group in the same alkyl group as described above, and the term “alkoxycarbonyl group” also includes a C1-C12 alkyl group. And alkoxycarbonyl groups.
  • alkoxycarbonyl group of the formula (2) examples include methyloxycarbonyl, ethyloxycarbonyl, propyloxycarbonyl, isopropyloxycarbonyl, butyloxycarbonyl, isobutyloxycarbonyl, pentyloxycarbonyl, isopentyloxycarbonyl, neopentyloxycarbonyl, Cyclopentyloxycarbonyl, hexyloxycarbonyl, cyclohexyloxycarbonyl, heptyloxycarbonyl, cycloheptyloxycarbonyl, octyloxycarbonyl, 2-ethylhexyloxycarbonyl, cyclooctyloxycarbonyl, nonyloxycarbonyl, decanyloxycarbonyl, tricyclodecanyloxy Carbonyl, methoxypropyloxycarbonyl, ethoxypro Hexyloxycarbonyl, hexyloxy propyl,
  • Examples of the aryl group of the formula (2) include aromatic hydrocarbon residues such as phenyl group, naphthyl group, anthryl group, phenanthryl group, pyrenyl group, benzopyrenyl group; pyridyl group, pyrazyl group, pyrimidyl group, quinolyl group, An aromatic heterocyclic residue such as an isoquinolyl group, a pyrrolyl group, an indolenyl group, an imidazolyl group, a carbazolyl group, a thienyl group, and a furyl group.
  • aromatic hydrocarbon residues such as phenyl group, naphthyl group, anthryl group, phenanthryl group, pyrenyl group, benzopyrenyl group; pyridyl group, pyrazyl group, pyrimidyl group, quinolyl group, An aromatic heterocyclic residue such as an isoquinolyl group, a pyrrol
  • aryl groups may have a substituent, and examples of the substituent include an alkyl group, an alkoxy group, a halogen atom, a sulfo group, a carboxyl group, an alkoxycarbonyl group, a carbamoyl group, and a cyano group.
  • the phenoxy group of the formula (2) may have a substituent, and examples of the substituent include a C1-C12 linear or branched alkyl group, a halogen atom, an amino group, an alkylamino group, and a hydroxyl group. .
  • Examples of the sulfo group of the formula (2) include methanesulfonyl, ethanesulfonyl, hexanesulfonyl, decanesulfonyl and the like.
  • Examples of the sulfamoyl group of the formula (2) include sulfamoyl, methanesulfamoyl, ethanesulfamoyl, propanesulfamoyl, isopropanesulfamoyl, butanesulfamoyl, isobutanesulfamoyl, pentansulfamoyl, and isopentanesulfur.
  • Famoyl neopentanesulfamoyl, cyclopentanesulfamoyl, hexanesulfamoyl, cyclohexanesulfamoyl, heptanesulfamoyl, cycloheptanesulfamoyl, octanessulfamoyl, 2-ethylhexanesulfamoyl, 1 , 5-Dimethylhexanesulfamoyl, cyclooctanesulfamoyl, nonanesulfamoyl, decanesulfamoyl, tricyclodecanesulfamoyl, methoxypropanesulfamoyl, ethoxy Lopansulfamoyl, propoxypropane sulfamoyl, isopropoxypropane sulfamoyl, hexyloxypropane sulfamoy
  • the carbamoyl group of the formula (2) may have a substituent, and examples of the substituent include a C1-C12 linear or branched alkyl group, a phenyl group, a tosyl group, and a pyrimidinyl group. Further, the carbamoyl group includes an aliphatic group in which two alkyl groups bonded to nitrogen have a C3 to C12 cycloalkyl ring in combination with the nitrogen atom, or one or more heteroatoms such as nitrogen, oxygen, and sulfur. A family heterocycle can be formed.
  • Each of the anion moieties Z ⁇ of the colorant compounds represented by the formulas (1) and (2) contained in the colored resin composition of the present invention independently represents a C1-C10 higher halogenated alkyl group.
  • the colorant compound used in the colored resin composition of the present invention can be obtained, for example, by a known synthesis method described in Yutaka Hosoda “Theoretical Manufacturing Dye Chemistry” (pages 373 to 375) issued by Gihodo Co., Ltd.
  • the anion part Z ⁇ of the colorant compound in the present invention is a chlorine anion
  • a corresponding salt or acid for salt exchange for example, a coloring material compound in which the anion portion Z ⁇ is a chlorine anion is reacted with a reaction solvent (for example, water, methanol, ethanol, isopropanol, acetone, N, N-dimethylformamide (hereinafter DMF)).
  • a reaction solvent for example, water, methanol, ethanol, isopropanol, acetone, N, N-dimethylformamide (hereinafter DMF)
  • a water-soluble polar solvent such as N-methyl-2-pyrrolidone (hereinafter abbreviated as NMP), and these solvents may be used alone or in combination.
  • NMP N-methyl-2-pyrrolidone
  • the total solid content of the blue colored resin composition of the present invention refers to the total amount of solid content comprising a colorant compound, a binder resin, a curing agent, etc., and is used synonymously hereinafter).
  • the content of the colorant compound represented is preferably 0.1 to 60 parts by mass, more preferably 3 to 30 parts by mass. When the content is larger than this range, problems of precipitation and aggregation occur, or the adhesiveness with the substrate is lowered due to insufficient curing. When the content is small, there is no major problem, but there is a tendency that sufficient color purity cannot be obtained as color characteristics.
  • the solubility of the colorant compound represented by the formula (1) in the colored resin composition is low, it is dispersed using a dispersant, a dispersion aid or the like in the same manner as a pigment which is an optional component described later. May be.
  • Two or more colorant compounds represented by the formula (1) may be mixed or used alone, but other dyes or pigments may be mixed. Since the present invention relates to a blue pixel, it is desirable to mix with a known blue dye or violet dye, or a blue pigment or violet pigment.
  • the binder resin used in the present invention functions as a dispersant and a dispersion aid because of dispersion stability at the time of pigment dispersion.
  • a design of a photolithography method in a development processing step at the time of manufacturing a color filter. It is desirable that it is soluble in the alkaline developer to be used, and further it has sufficient curing characteristics with a photopolymerization initiator, a photopolymerizable monomer, etc. in order to form a good fine pattern.
  • the obtained pigment-dispersed resin composition must have good compatibility with constituent materials such as a photopolymerization initiator, a photopolymerizable monomer, and a pigment dispersion, and be stable so as not to cause precipitation or aggregation.
  • constituent materials such as a photopolymerization initiator, a photopolymerizable monomer, and a pigment dispersion
  • alkali solubility is not particularly necessary, and therefore a resin having good compatibility with other colorant compounds and additives may be selected.
  • a known resin can be used as the binder resin, but more preferably one or more of the following carboxyl groups or ethylenically unsaturated monomers having a hydroxyl group or other copolymerizable aromatic hydrocarbon groups. And a copolymer such as an ethylenically unsaturated monomer having an aliphatic hydrocarbon group.
  • those having an epoxy group at the side chain or terminal, and epoxy acrylate resins to which acrylate is added can also be used. These monomers may be used alone or in combination of two or more.
  • Examples of the carboxyl group-containing unsaturated monomer that can be used in the present invention include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, ⁇ -chloroacrylic acid, ethacrylic acid, cinnamic acid; maleic acid, anhydrous Unsaturated dicarboxylic acids (anhydrides) such as maleic acid, fumaric acid, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, mesaconic acid; trivalent or higher unsaturated polycarboxylic acids (anhydrides); Examples include 2- (meth) acryloyloxyethyl hexahydrophthalic acid, 2-methacryloyloxyethyl 2-hydroxypropyl phthalate, and 2-acryloyloxyethyl 2-hydroxyethyl phthalic acid. These ethylenically unsaturated monomers having a carboxyl group can be used alone or in
  • hydroxyl group-containing unsaturated monomer examples include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) ) Acrylate, 3-hydroxybutyl (meth) acrylate, 5-hydroxypentyl (meth) acrylate, 4-hydroxypentyl (meth) acrylate, 3-hydroxypentyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 5- Hydroxyhexyl (meth) acrylate, 4-hydroxyhexyl (meth) acrylate, 5-hydroxy-3-methyl-pentyl (meth) acrylate, cyclohexane-1,4-dimethanol-mono (meth) acrylate, -Hydroxyl-terminated polyalkylenes such as (2-hydroxyethyloxy) ethyl (meth)
  • Examples of the other unsaturated monomer include styrene, ⁇ -methylstyrene, o-vinyltoluene, m-vinyltoluene, p-vinyltoluene, o-chlorostyrene, m-chlorostyrene, p-chlorostyrene, Aromatic vinyl compounds such as p-methoxystyrene; methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, i-propyl (meth) acrylate, n-butyl (meth) acrylate, i-butyl (Meth) acrylate, sec-butyl (meth) acrylate, t-butyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, benzyl (meth) acrylate, paracumylphenoxyethylene glycol (me
  • a polymer in which an unsaturated double bond is further introduced into the side chain of the copolymer is also useful.
  • an acrylate having an alcoholic hydroxyl group such as hydroxyethyl acrylate in the maleic anhydride portion of a copolymer with styrene, vinylphenol, acrylic acid, acrylic ester, acrylamide, or the like copolymerizable with maleic anhydride
  • Acrylic acid is added to the hydroxyl group of a compound obtained by reacting an acrylate having an epoxy group, such as glycidyl methacrylate, and half-esterified, and a copolymer of acrylic acid, an acrylic ester and an acrylate having an alcoholic hydroxyl group such as hydroxyethyl acrylate.
  • urethane resin, polyamide, polyimide resin, polyester resin commercially available ACA-200M (manufactured by Daicel), ORGA-3060 (manufactured by Osaka Organic Chemical), AX3-BNX02 (manufactured by Nippon Shokubai), UXE-3024 (Nippon Kayaku) UXE-3000 (Nippon Kayaku), ZGA-287H (Nippon Kayaku), TCR-1338H (Nippon Kayaku), ZXR-1722H (Nippon Kayaku), ZFR-1401H (Nippon Kayaku) And ZCR-1642 (manufactured by Nippon Kayaku) can also be used.
  • a dispersant and a dispersion aid are used when dispersing a pigment.
  • pigment-based dispersants there are pigment-based dispersants, resin-based dispersants, surfactants, and the like having good adsorptivity to pigments.
  • a pigment-based dispersant there are known a method of mixing a sulfonated pigment or a metal salt thereof as described in Patent Documents 4 to 6 with a pigment, a method of mixing a substituted aminomethyl derivative (Patent Document 7), and the like. It has been.
  • Some resin dispersants are nonpolar nonionic, but polymer resins having an acid value, an amine value, etc.
  • pigment adsorption is common, such as acrylic resins, polyurethane resins, and polycarboxylic acids. , Polyamide resin, polyester resin and the like. Specific examples thereof include ED211 (manufactured by Enomoto Kasei), Ajisper PB821 (manufactured by Ajinomoto Fine Techno), Solsperse 71000 (manufactured by Avicia), and the like.
  • a polymerization initiator When producing the binder resin (copolymer) used in the present invention, a polymerization initiator is used.
  • the polymerization initiator used when synthesizing the copolymer are, for example, ⁇ , ⁇ ′-azobis (isobutyronitrile), 2,2′-azobis (2-methylbutyronitrile). ), T-butyl peroctoate, di-t-butyl peroxide benzoylmethyl ethyl ketone peroxide, and the like.
  • the use ratio of the polymerization initiator is 0.01 to 25 parts by mass with respect to the total of all monomers used for the synthesis of the copolymer.
  • the reaction temperature when synthesizing the copolymer is preferably 50 to 120 ° C., particularly preferably 80 to 100 ° C.
  • the reaction time is preferably 1 to 60 hours, more preferably 3 to 20 hours.
  • the preferred acid value of the copolymer is 10 to 300 (mgKOH / g), and the preferred hydroxyl value is 10 to 200 (mgKOH / g). When the acid value or hydroxyl value is 10 or less, developability is lowered.
  • the weight average molecular weight (Mw) of the copolymer is preferably from 2,000 to 400,000, more preferably from 3,000 to 100,000. When the weight average molecular weight is 2000 or less, or 400000 or more, sensitivity, developability and the like are lowered.
  • the binder resins can be used alone or in admixture of two or more.
  • the content of the binder resin in the present invention is usually 0.5 to 99 parts by mass, preferably 5 to 50 parts by mass with respect to 100 parts by mass of the total solid content of the colored resin composition. In this case, if the content of the binder resin is less than 0.5 parts by mass, the alkali developability may be lowered, or problems such as scumming or film residue in areas other than the area where pixels are formed may occur. is there.
  • Examples of the curing agent that can be used in the present invention include a photopolymerization monomer in the case of radical polymerization, an epoxy resin in the case of ion curing, and a melamine curing agent.
  • Specific examples thereof include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene Glyco (meth) acrylate, tetraethylene glycol (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol di (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol Hexa (meth) acrylate,
  • the colorant that can be used in combination with the colored resin composition of the present invention preferably has a spectral characteristic suitable for a color filter, and can be appropriately selected from dyes, organic pigments, and inorganic pigments. It can also be used in combination of more than one species. These contents are 0 to 60 parts by mass, preferably 5 to 30 parts by mass with respect to 100 parts by mass of the total solid content of the colored resin composition. These various pigments and dyes are shown below.
  • the organic pigment that can be used in the present invention is not particularly limited.
  • anthraquinone, phthalocyanine, triphenylmethane, benzimidazolone, quinacridone, azochelate, azo, isoindoline, and isoindolinone Pyranthrone, indanthrone, anthrapyrimidine, dibromoanthanthrone, flavanthrone, perylene, perinone, quinophthalone, thioindigo, dioxazine, quinacridone, xanthene, and other pigments; acidic dyes, basic Examples include lake pigments and dyed lake pigments obtained by insolubilizing dyes, direct dyes, and the like with the respective precipitation agents.
  • the color index for example, Pigment Blue 1, 1: 2, 9, 14, 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 17, 19 25, 27, 28, 29, 33, 35, 36, 56, 56: 1, 60, 61, 61: 1, 62, 63, 66, 67, 68, 71, 72, 73, 74, 75, 76 78, 79; Pigment Violet 1, 1: 1, 2, 2: 2, 3, 3: 1, 3: 3, 5, 5: 1, 14, 15, 16, 19, 23, 25, 27, 29 31, 32, 37, 39, 42, 44, 47, 49, 50; Pigment Violet 3, 4, 27, 39, and the like.
  • Pigment Blue 15: 6 and Pigment Violet 23 are more preferable because of good hue and resistance.
  • the inorganic pigment that can be used in combination with the present invention is not particularly limited.
  • composite metal oxide pigments, carbon black, black low-order titanium oxide, titanium oxide, barium sulfate, zinc white, lead sulfate, yellow lead, red rose, ultramarine blue , Bitumen, chromium oxide, antimony white, iron black, red lead, zinc sulfide, cadmium yellow, cadmium red, zinc, manganese purple, cobalt purple, barium sulfate, magnesium carbonate and other metal oxides, metal sulfides, sulfates, Metal hydroxide, metal carbonate, etc. are mentioned.
  • the dye that can be used in the present invention is not particularly limited, and examples thereof include acid dyes, basic dyes, direct dyes, sulfur dyes, vat dyes, naphthol dyes, reactive dyes, and disperse dyes. Among them, any dye that is soluble in an organic solvent may be used, but even a dye that is insoluble in an organic solvent can be appropriately used by forming a dispersion.
  • dyes that are insoluble in organic solvents are well-known formulations.
  • organic amine compounds for example, n-propylamine, ethylhexylpropionate amine, etc.
  • amine salt dyes It is known to modify or to make a dye having a sulfonamide group by reacting the sulfonic acid group with the same organic amine compound.
  • amine-modified dyes can also be used in the colored resin composition of the present invention.
  • the specific dye is a color index, for example, Solvent Blue 2, 3, 4, 5, 6, 23, 35, 36, 37, 38, 43, 48, 58, 59, 67, 70, 78, 98, 102, 104; Basic Blue 7; Acid Blue 80, 83, 90;
  • violet dyes include Solvent Violet 8, 9; Violet 4, 5, 14; Basic Violet 10 and the like.
  • photopolymerization initiator added to the colored resin of the present invention used in the photographic method those having sufficient sensitivity to ultraviolet rays emitted from an ultra-high pressure mercury lamp generally used as an exposure light source are preferable, and radical polymerization property Photo-radical initiators, ion-curing photo-acid generators or photo-base generators.
  • a component of a polymerization accelerator called a sensitizer that can be cured with less exposure energy can be used in combination.
  • the photopolymerization initiator that can be used is not particularly limited.
  • benzyl benzoin ether
  • benzoin butyl ether benzoin propyl ether
  • benzophenone 3,3′-dimethyl-4-methoxybenzophenone
  • benzoylbenzoic acid benzoylbenzoic acid.
  • Acid esterified product 4-benzoyl-4'-methyldiphenyl sulfide, benzyldimethyl ketal, 2-butoxyethyl-4-methylaminobenzoate, chlorothioxanthone, methylthioxanthone, ethylthioxanthone, isopropylthioxanthone, dimethylthioxanthone, diethylthioxanthone, diisopropyl Thioxanthone, dimethylaminomethylbenzoate, 1- (4-dodecylphenyl) -2-hydroxy-2-methylpropan-1-one 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, methylbenzoyl formate 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one, 2-benz
  • thermosetting resin composition used in an inkjet method or the like
  • a thermal polymerization initiator is generally used, but a photopolymerization initiator may be used in combination as necessary.
  • the thermal polymerization initiator include azo compounds and organic peroxides, such as 2,2′-azobisisobutyronitrile, 2,2′-azobis (2,4-dimethylvaleronitrile), Examples include 2,2′-azobis (2-methylbutyronitrile), di-t-butyl peroxide, dibenzoyl peroxide, cumylperoxyneodecanoate, and the like.
  • These polymerization initiators can be used alone or in combination of two or more as required. These contents are 0.5 to 50 parts by mass, preferably 1 to 25 parts by mass, when the total solid content of the colored resinous composition is 100 parts by mass.
  • the organic solvent used in the present invention has sufficient dissolving power with respect to the binder resin, photopolymerizable monomer, photopolymerization initiator, and the like, which are components of the colored resin composition, and is a monofunctional compound used for the synthesis of the binder resin. Those having sufficient dissolving power for monomers, polymerization initiators and the like can be used. Moreover, what can maintain dispersion stability can also be used when preparing a pigment dispersion.
  • the organic solvent used in the present invention is not particularly limited as long as it can be used.
  • Specific examples include benzenes such as benzene, toluene and xylene; cellosolves such as methyl cellosolve, ethyl cellosolve and butyl cellosolve; methyl cellosolve acetate.
  • Cellosolve acetates such as ethyl cellosolve acetate and butyl cellosolve acetate; propylene glycol monoalkyl ether acetates such as propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate and propylene glycol monobutyl ether acetate; methyl methoxypropionate, methoxypropion Propionates such as ethyl acrylate, methyl ethoxypropionate, ethyl ethoxypropionate; methyl lactate, milk Lactic acid esters such as ethyl and butyl lactate; Diethylene glycols such as diethylene glycol monomethyl ether and diethylene glycol monoethyl ether; Acetic esters such as methyl acetate, ethyl acetate and butyl acetate; Ethers such as dimethyl ether, diethyl ether, tetrahydrofuran and
  • the amount of the organic solvent used is preferably 40 to 10,000 parts by mass, more preferably 100 to 1000 parts by mass with respect to 100 parts by mass of the total solid content of the colored resin composition.
  • the colored resin composition of the present invention is produced by mixing and stirring the binder resin, curing agent, photopolymerization initiator, specific colorant compound, organic solvent, and the like with a dissolver, a homomixer, or the like.
  • a dispersion is obtained by a dispersing machine such as a paint shaker using an appropriate dispersant, In addition to the colored resin composition, it is mixed.
  • the colored resin composition of the present invention may further contain various additives such as fillers, surfactants, thermal polymerization inhibitors, adhesion promoters, antioxidants, ultraviolet absorbers, anti-aggregation agents, and the like. Can be added.
  • the colored resin composition of the present invention can be microfiltered with a filter or the like in order to remove foreign matters after the preparation.
  • the colored resin composition of the present invention is formed on a substrate such as a glass substrate or a silicon substrate by a method such as a spin coating method, a roll coating method, a slit and spin method, a die coating method, or a bar coating method. It is applied to 1 to 20 ⁇ m, preferably 0.5 to 5 ⁇ m. If necessary, it is dried in a vacuum chamber at a temperature of 23 to 150 ° C. for 1 to 60 minutes, more preferably a temperature of 60 to The film is dried under reduced pressure at 120 ° C. for 1 to 10 minutes, and further pre-baked with a hot plate or a clean oven to form a film.
  • radiation for example, electron beam, ultraviolet ray, preferably ultraviolet ray
  • development is performed with a surfactant aqueous solution, an alkaline aqueous solution, or a mixed aqueous solution of a surfactant and an alkaline agent.
  • the development method include a dipping method, a spray method, a shower method, a paddle method, and an ultrasonic development method, and any of these methods may be combined.
  • the post-baking treatment is performed, for example, at a temperature of 130 to 300 ° C. for 1 to 120 minutes, more preferably at a temperature of 150 to 250 ° C. for 1 to 30 minutes.
  • polyoxyethylene alkyl ether, polyoxyalkylene alkyl ether, etc. can be used as the surfactant.
  • the alkali agent sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, diethanolamine, tetramethylammonium hydroxide, or the like is used.
  • an aqueous solution containing both an alkali agent and a surfactant is usually carried out at a processing temperature of 10 to 50 ° C., preferably 20 to 40 ° C., for a processing time of usually 30 to 600 seconds, preferably 30 to 120 seconds.
  • the cured product of the colored resin composition of the present invention is useful as a color filter suitable for a liquid crystal display device, an organic EL display, a solid-state image sensor used in a digital camera, etc., and the color filter is as described above. Having a patterned blue pixel made of a cured product of the colored resin composition of the present invention.
  • the liquid crystal display device of the present invention is produced, for example, with a structure in which a backlight, a polarizing film, a display electrode, a liquid crystal, an alignment film, a common electrode, a color filter of the present invention, a polarizing film and the like are laminated in this order.
  • the organic EL display is manufactured by forming a color filter on either the upper or lower side of the multilayer organic light emitting element.
  • the solid-state imaging device is manufactured, for example, by providing the color filter layer of the present invention on a silicon wafer provided with transfer electrodes and photodiodes, and then laminating microlenses.
  • % means “% by mass” unless otherwise specified.
  • the spectral transmittance was measured with a spectrophotometer “Shimadzu Corporation UV-3150”, the chromaticity in the XYZ color system was calculated, and the resistance of the colored body was evaluated.
  • Synthesis Example 4 (Preparation of binder resin (copolymer)) A 500 ml four-necked flask was charged with 160 g of methyl ethyl ketone, 10 g of methacrylic acid, 33 g of benzyl methacrylate, and 1 g of ⁇ , ⁇ ′-azobis (isobutyronitrile), and nitrogen gas was allowed to flow into the flask for 30 minutes while stirring. Thereafter, the temperature was raised to 80 ° C., and the mixture was stirred at 80 to 85 ° C. for 4 hours. After completion of the reaction, the reaction mixture was cooled to room temperature to obtain a colorless, transparent and uniform copolymer solution.
  • copolymer (A) This was precipitated in a 1: 1 mixed solution of isopropyl alcohol and water, filtered, and the solid content was taken out and dried to obtain a copolymer (A).
  • the resulting copolymer (A) had a polystyrene equivalent weight average molecular weight of 18,000 and an acid value of 152.
  • Example 1 5.4 g of copolymer (A) as a binder resin, 6 g of Kayrad DPHA (manufactured by Nippon Kayaku) as a photopolymerizable monomer, 1.5 g of Irgacure 907 (manufactured by BASF Japan) as a photopolymerization initiator, and Kayacure DETX-S ( Nippon Kayaku Co., Ltd.) 0.6 g, Compound 1-1 of Synthesis Example 1 0.6 g, Cyclohexanone 20 g and propylene glycol monomethyl ether acetate 8.6 g as a solvent were mixed, and the colored photosensitive resin composition of the present invention was mixed. Got.
  • Example 2 The composition was the same as that of Example 1, except that the colorant compound 1-1 was changed to the compound 1-3 of Synthesis Example 2.
  • the blue pigment dispersion liquid 1 was obtained by processing for 60 minutes with a paint shaker and filtering. 19g of blue dispersion liquid 1 was added to Example 1, and the blue colored photosensitive resin composition of this invention was obtained.
  • Example 4 0.6 g of Compound 2-3 of Synthesis Example 3 was further added to Example 3.
  • Comparative Example 1 19 g of blue pigment dispersion 1 described in Example 3 was used to obtain a blue photosensitive pigment resin composition containing only pigment.
  • Comparative Example 2 The same composition as in Example 1 was used except that Compound 1-1 was changed to Basic Blue 7, which is a dye having a clear blue characteristic.
  • the colored photosensitive resin compositions (Examples 1 to 4 and Comparative Examples 1 and 2) obtained above were applied onto the substrate, pre-baked at 80 ° C. for 100 seconds, and then exposed through a mask. After curing, development was performed with an alkaline aqueous solution containing a surfactant, rinsed with water, and then heated at 200 ° C. to obtain a blue pattern.
  • the obtained blue pattern had a resolution of 5 ⁇ m square in line and space, and no residue, peeling of pixels, etc. were confirmed.
  • a substrate for evaluation of spectral characteristics and heat resistance was prepared by applying each composition to a glass substrate, exposing the whole surface, and performing a post-bake treatment at 200 ° C. for 5 minutes. . In both cases, a color filter substrate having clear blue characteristics was obtained. Thereafter, each evaluation was performed as described below. The heat resistance was evaluated by measuring the spectral transmittance of the evaluation substrate before and after the treatment at 200 ° C. for 120 minutes and calculating the color difference ( ⁇ Eab) before and after the heat treatment.
  • Contrast was measured with a contrast meter (CT-1 manufactured by Osaka Co., Ltd.) using the evaluation substrate, and the luminance value (cd / cm 2 ) when the two polarizing plates were parallel to each other (cd / cm 2 ).
  • the contrast was calculated from the ratio of cm 2 ) (brightness value in parallel / brightness value in orthogonal).
  • the heat resistance results are shown in Table 1, and the contrast results are shown in Table 2.
  • Examples 1 to 4 of the present invention all show better results than Comparative Example 2, and the resistance of the colorant compound of the present invention is greatly improved. Since the comparative example 1 used the pigment for the color material compound, it was the result with the best resistance, and since Example 4 was also mixed with the pigment, the result was also good with good resistance. Paying attention to Example 4 in the case of mixing the pigment, the insoluble matter and the like are not particularly precipitated, and the state is good, which suggests the wide applicability of the dye-based color material compound of the present invention. I can say that. Further, from the evaluation results of the contrast in Table 2, all of Examples 1 to 3 showed better results than the pigment of Comparative Example 1, and the colored resin composition of the present invention has suitability for color filters. I was able to confirm that.
  • the blue colored resin composition of the present invention using a specific blue dye-based color material compound is vivid blue, has excellent color filter characteristics (resistance, contrast, etc.), and has high quality and reliability.
  • a high-quality blue pixel can be obtained.
  • it can be used by being well mixed with pigments depending on the application, and shows wide applicability.

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Abstract

La présente invention concerne un filtre coloré fiable, plus résistant et possédant des caractéristiques de bleu vif de grande qualité. L'utilisation d'un composé de colorant bleu spécifique permet d'obtenir facilement la composition de résine colorée bleue présentée et destinée à être utilisée pour fabriquer des filtres colorés à pixels bleus, en y ajoutant en plus une résine de liant, un solvant, un agent de durcissement, etc. Les filtres colorés à pixels bleus produits sont fiables et de grande qualité. Ils présentent en outre d'excellentes caractéristiques de couleur, tel le contraste, ainsi que d'excellentes propriétés de résistance, telle la résistance à la chaleur.
PCT/JP2011/070600 2010-09-16 2011-09-09 Composition de résine colorée WO2012036085A1 (fr)

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JP2012226130A (ja) * 2011-04-20 2012-11-15 Toppan Printing Co Ltd 感光性組成物及びそれを用いたカラーフィルタ、液晶ディスプレイ及び有機ｅｌディスプレイ
JP2013144724A (ja) * 2012-01-13 2013-07-25 Sumitomo Chemical Co Ltd 着色硬化性樹脂組成物
JP2015038186A (ja) * 2013-07-18 2015-02-26 富士フイルム株式会社 色素多量体の製造方法、および着色組成物の製造方法
CN105573055A (zh) * 2014-10-30 2016-05-11 住友化学株式会社 着色固化性树脂组合物
JP2018162364A (ja) * 2017-03-24 2018-10-18 三菱ケミカル株式会社 着色樹脂組成物、カラーフィルタ及び画像表示装置

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KR102410887B1 (ko) 2018-03-15 2022-06-20 동우 화인켐 주식회사 착색 감광성 수지 조성물, 컬러 필터 및 이를 구비한 화상표시장치
KR102467423B1 (ko) 2019-03-11 2022-11-15 동우 화인켐 주식회사 청색 염료를 포함하는 착색 경화성 수지 조성물, 이를 이용하여 제조된 컬러필터 및 화상표시장치

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JP2011133844A (ja) * 2009-11-30 2011-07-07 Dainippon Printing Co Ltd カラーフィルター用着色組成物及びそれを用いたカラーフィルター、並びに表示装置

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JP2012226130A (ja) * 2011-04-20 2012-11-15 Toppan Printing Co Ltd 感光性組成物及びそれを用いたカラーフィルタ、液晶ディスプレイ及び有機ｅｌディスプレイ
JP2013144724A (ja) * 2012-01-13 2013-07-25 Sumitomo Chemical Co Ltd 着色硬化性樹脂組成物
JP2015038186A (ja) * 2013-07-18 2015-02-26 富士フイルム株式会社 色素多量体の製造方法、および着色組成物の製造方法
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CN105573055A (zh) * 2014-10-30 2016-05-11 住友化学株式会社 着色固化性树脂组合物
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JP2018162364A (ja) * 2017-03-24 2018-10-18 三菱ケミカル株式会社 着色樹脂組成物、カラーフィルタ及び画像表示装置
JP7052206B2 (ja) 2017-03-24 2022-04-12 三菱ケミカル株式会社 着色樹脂組成物、カラーフィルタ及び画像表示装置

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