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WO2013011687A1 - Composition de résine colorée pour des filtres colorés - Google Patents

Composition de résine colorée pour des filtres colorés Download PDF

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Publication number
WO2013011687A1
WO2013011687A1 PCT/JP2012/004579 JP2012004579W WO2013011687A1 WO 2013011687 A1 WO2013011687 A1 WO 2013011687A1 JP 2012004579 W JP2012004579 W JP 2012004579W WO 2013011687 A1 WO2013011687 A1 WO 2013011687A1
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Prior art keywords
group
anion
formula
color filter
resin composition
Prior art date
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Ceased
Application number
PCT/JP2012/004579
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English (en)
Japanese (ja)
Inventor
尚文 堀口
手嶋　徹
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Nippon Kayaku Co Ltd
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Nippon Kayaku Co Ltd
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Publication of WO2013011687A1 publication Critical patent/WO2013011687A1/fr
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Classifications

    • 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
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
    • C08F290/14—Polymers provided for in subclass C08G
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—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
    • 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

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 equipped with the color filter, an image sensor (CCD, CMOS), an organic EL display, etc.
  • the present invention relates to an electronic display device.
  • a color filter For colorization of liquid crystal display elements such as notebook computers, liquid crystal televisions, mobile phones, and other liquid crystal displays (LCD), and image sensors (CCD, CMOS) used as input devices for digital cameras, color copiers, etc. Need a color filter.
  • a method for producing a color filter there are a dyeing method, an electrodeposition method, a printing method, a pigment dispersion method, etc., but in recent years, the pigment dispersion method has become mainstream, and when patterning is necessary, the method is as follows.
  • a photolithography method is typical. That is, the color filter is configured using a mixture of a photosensitive resin composition and a pigment dispersion. Recently, 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.
  • Patent Document 1 and Patent Document 2 describe a color filter using a triphenylmethane-based compound, but the triphenylmethane-based compound is extremely inferior in light resistance and heat resistance and is not at a practical level.
  • Patent Document 3 has a description that xanthene compounds are excellent in lightness, but there is no description regarding resistance performance, and further, xanthene compounds are fluorescent dyes, which may cause a decrease in contrast due to light scattering as in the case of pigments. There is. Further, when a liquid crystal alignment film is formed on a color filter, a solvent having a high dissolving power such as N-methylpyrrolidone is used as a solvent for the liquid crystal alignment film material, but it does not elute even when immersed in the solvent. Materials that do not undergo spectral changes are desired. That is, since the dye has higher solvent solubility than the pigment, the color filter using the dye is required to have solvent resistance. There is a demand for a colored resin composition containing various colorant compounds having excellent resistance for color filters that require high reliability, but there is no practically available one. Therefore, there is a demand for a high-quality color filter having excellent resistance.
  • a solvent having a high dissolving power such as N-methylpyrrolidone is
  • JP-A-8-94826 Japanese Patent Laid-Open No. 2002-14222 JP 2010-32999 A Japanese Patent Laid-Open No. Sho 63-172772
  • the present invention provides a colored resin composition having a clear color purity characteristic, showing good patternability with few residues, etc., and providing a color filter excellent in light resistance, heat resistance, solvent resistance, and the like.
  • the purpose is to provide a filter.
  • the present inventors have formed a colored resin composition containing a specific colorant compound, a specific unsaturated group-containing polycarboxylic acid resin, a photopolymerization initiator and a solvent, and a colored resin composition formed therefrom.
  • the present inventors have found a color filter to be completed and completed the present invention.
  • the present invention relates to the following 1) to 14).
  • 1) (i) a colorant compound represented by the following formula (1) and / or the following formula (2),
  • a polybasic acid carboxylic acid anhydride (c) is reacted with a reaction product of an epoxy resin (a) represented by the following formula (3) and an unsaturated group-containing monocarboxylic acid compound (b) as a binder resin.
  • An unsaturated group-containing polycarboxylic acid resin obtained by (Iii) a photopolymerization initiator, and (iv) a solvent, A colored resin composition for a color filter.
  • R 1b to R 6b each independently represent a hydrogen atom, a halogen atom, an optionally substituted (C1-C12) alkyl group, or an optionally substituted (C1-C12) alkoxy.
  • Y 1 to Y 4 each independently have a hydrogen atom or a substituent ( C1-C12) an alkyl group, an optionally substituted aryl group or an optionally substituted aromatic heterocyclic group
  • X 1 to X 5 each independently represents a hydrogen atom, a substituent (C1-C12) alkyl group which may have a substituent, (C1-C12) alkoxy group which may have a substituent, a halogen atom, a nitro group, a phenoxy group, a carboxy group and a substituent.
  • R 1 to R 6 each independently have a hydrogen atom, an optionally substituted (C1-C30) alkyl group, an optionally substituted phenyl group or a substituent.
  • R 7 to R 20 each independently represents a hydrogen atom, a halogen atom or a (C1-C6) alkyl group which may have a substituent
  • Z 2 — represents (C1-C10 An alkylsulfonylmethide anion having a higher-order halogenated alkyl group, (C1-C10) an alkylsulfonylimide anion having a higher-order halogenated alkyl group, or (C1-C10) an alkylsulfonate anion having a higher-order halogenated alkyl group. Show.
  • n an average value of 0 to 10
  • G represents a glycidyl group
  • P and R each independently represent a hydrogen atom, a halogen atom, a (C1-C8) alkyl group or an aryl group, and each P Or R may mutually be same or different.
  • Z 1 - and Z 2 - are each independently a tristotrifluoromethanesulfonylmethide anion, a bistrifluoromethanesulfonylimide anion, or a trifluoromethanesulfonate anion.
  • R 1b , R 3b , R 4b and R 6b in the formula (1) are hydrogen atoms
  • R 2b and R 5b are each independently a hydrogen atom or a (C1-C3) alkyl group
  • Y 1 to Y 4 is each independently a hydrogen atom or a (C1-C3) alkyl group
  • X 2 to X 5 are each independently a hydrogen atom or a halogen atom
  • R 1 to R 4 and R 6 in formula (2) are each The color filter according to 1) or 2) above, which is independently a hydrogen atom or a (C1-C6) alkyl group
  • R 7 to R 20 are a hydrogen atom, an unsubstituted (C1-C3) alkyl group or a chlorine atom.
  • Coloring resin composition 4) The color filter according to 3), wherein X 1 in formula (1) is a carboxy group or an unsubstituted (C1-C3) alkoxycarbonyl group, and R 5 in formula (2) is a hydrogen atom. Colored resin composition.
  • R 1b to R 6b are hydrogen atoms
  • Y 1 to Y 4 are all ethyl groups
  • X 1 is a carboxy group
  • X 2 to X 5 are all hydrogen atoms
  • R 1 to R 4 and R 6 are all ethyl groups
  • R 5 is a hydrogen atom
  • R 7 to R 20 are all hydrogen atoms
  • Z 1 ⁇ in formula (1) and is independently tris trifluoromethanesulfonyl methide anion
  • a color filter for the colored resin composition according to above 1) is bistrifluoromethanesulfonylimide anion or trifluoromethanesulfonate anion - Z 2 of formula (2).
  • the colorant compound is a compound represented by the formula (1), R 1b to R 6b are hydrogen atoms, Y 1 to Y 4 are all ethyl groups, X 1 is a carboxy group, and X 2 to The colored resin composition for a color filter according to 1) above, wherein X 5 is a hydrogen atom, and Z 1 - is a tristotrifluoromethanesulfonylmethide anion or a bistrifluoromethanesulfonylimide anion.
  • the content of the colorant compound (i) is 0.1 to 60 parts by mass
  • the content of the binder resin is 0.5 to 90 parts by mass
  • photopolymerization is started.
  • the colored resin composition for a color filter according to one item. The colored resin composition for a color filter according to any one of 1) to 7), further comprising (v) a metal phthalocyanine pigment.
  • the color resin composition for a color filter of the present invention and the color filter formed therefrom include a specific colorant compound, thereby exhibiting clear color purity, good patternability with few residues, light resistance, and heat resistance.
  • a high-quality color filter having excellent resistance to solvent and the like.
  • the colored resin composition for a color filter of the present invention is (I) Formula (1) (wherein R 1b to R 6b each independently have a hydrogen atom, a halogen atom or a substituent (C1-C12) an alkyl group or a substituent.
  • (C1-C12) an alkoxy group, a nitro group, a carboxy group or an optionally substituted (C1-C12) alkoxycarbonyl group
  • Y 1 to Y 4 are each independently a hydrogen atom
  • X 1 to X 5 Each independently represents a hydrogen atom, an optionally substituted (C1-C12) alkyl group, an optionally substituted (C1-C12) alkoxy group, a halogen atom, a nitro group, a phenoxy group, Carboxy group, having a substituent
  • the “halogen atom” is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • the “(C1-C12) alkyl group” in the “optionally substituted (C1-C12) alkyl group” in the formula (1) is a linear, branched or cyclic alkyl group having 1 to 12 carbon atoms. Groups.
  • Examples of the “(C1-C12) alkyl group optionally having substituent (s)” include, for example, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, s-butyl group, t -Butyl group, iso-butyl group, n-pentyl group, n-hexyl group, n-octyl group, n-decyl group, n-dodecyl group, 2-ethylhexyl group, cyclohexyl group, hydroxyethyl group, hydroxypropyl group, Examples include hydroxybutyl group, 2-sulfoethyl group, carboxyethyl group, cyanoethyl group, methoxyethyl group, ethoxyethyl group, butoxyethyl group, trifluoromethyl group, pentafluoroethyl group
  • Examples of the “optionally substituted (C1-C12) alkoxy group” include a group in which the alkyl group is bonded to an oxygen atom.
  • Examples of the “optionally substituted (C1-C12) alkoxycarbonyl group” include a group in which the alkoxy group is bonded to a carbonyl group.
  • the “aryl group” includes, for example, phenyl group, naphthyl group, anthryl group, phenanthryl group, pyrenyl group, benzopyrenyl group and the like.
  • the “aromatic heterocyclic group optionally having substituent” means, for example, a pyridyl group, pyrazyl group, pyrimidyl group, quinolyl group, isoquinolyl group, pyrrolyl group, indolenyl group Imidazolyl group, carbazolyl group, thienyl group, furyl group and the like.
  • substituents in these include an alkyl group, an alkoxy group, a halogen atom, a sulfo group, a carboxy group, an alkoxycarbonyl group, a carbamoyl group, and a cyano group.
  • substitution position and the number of substitutions of the substituent are not particularly limited as long as they can be substituted.
  • Examples of the anion part Z 1 — of the colorant compound represented by the formula (1) include tristrifluoromethanesulfonylmethide anion, bistrifluoromethanesulfonylimide anion, trifluoromethylsulfonate, nonafluorobutylsulfonate, and the like.
  • tristrifluoromethanesulfonylmethide anion is preferred.
  • R 1b , R 3b , R 4b and R 6b in the formula (1) are preferably hydrogen atoms, and R 2b and R 5b are each independently preferably a hydrogen atom or an unsubstituted (C1-C3) alkyl group, More preferably, it is a hydrogen atom.
  • Y 1 to Y 4 are preferably each independently a hydrogen atom or an unsubstituted (C1-C3) alkyl group.
  • Y 1 to Y 4 are unsubstituted (C1-C3) alkyl groups, and the remaining two are hydrogen atoms or unsubstituted (C1-C3) alkyl groups, and more preferably Y 1 All of Y 4 are unsubstituted (C1-C3) alkyl groups.
  • X 1 is preferably a carboxy group or a (C1-C3) alkoxycarbonyl group, more preferably a carboxy group.
  • X 2 to X 5 are each independently preferably a hydrogen atom or a halogen atom, more preferably a hydrogen atom.
  • Examples of the unsubstituted (C1-C3) alkyl group include a methyl group, an ethyl group, an n-propyl group, and an iso-propyl group, and a methyl group or an ethyl group is more preferable.
  • a preferable compound in the formula (1) is a compound in which the above-described preferable groups are combined, and more preferably, R 1b , R 3b , R 4b , and R 6b are hydrogen atoms, and R 2b and R 5b are each independently A hydrogen atom or an unsubstituted (C1-C3) alkyl group, Y 1 to Y 4 are each independently a hydrogen atom or an unsubstituted (C1-C3) alkyl group, at least two of which are unsubstituted (C1-C3) )
  • An alkyl group, X 1 is a carboxy group, X 2 to X 5 are each independently a hydrogen atom, and Z 1 - is a tristotrifluoromethanesulfonylmethide anion, a bistrifluoromethanesulfonylimide anion or a trifluoromethanesulfonate anion Can be mentioned.
  • R 1b to R 6b are all hydrogen atoms
  • Y 1 to Y 4 are each independently an unsubstituted (C1-C3) alkyl group
  • X 1 is a carboxy group
  • X 2 to Examples thereof include compounds in which X 5 is each independently a hydrogen atom
  • Z 1 - is a tristotrifluoromethanesulfonylmethide anion, a bistrifluoromethanesulfonylimide anion, or a trifluoromethanesulfonate anion.
  • the most preferred compound is Cl ⁇ of rhodamine B (R 1b to R 6b are all hydrogen atoms, Y 1 to Y 4 are all ethyl groups, X 1 is a carboxy group, and X 2 to X 5 are all hydrogen atoms),
  • R 1b to R 6b are all hydrogen atoms
  • Y 1 to Y 4 are all ethyl groups
  • X 1 is a carboxy group
  • X 2 to X 5 are all hydrogen atoms
  • the “(C1-C30) alkyl group” is a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms. Groups.
  • the “optionally substituted (C1-C30) alkyl group for example, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a 1-methylpropyl group ( s-butyl group), iso-butyl group, n-pentyl group, 1-ethylpropyl group, 1-methylbutyl group, cyclopentyl group, n-hexyl group, 1-methylpentyl group, 1-ethylbutyl group, cyclohexyl group Hydroxypropyl group, 2-sulfoethyl group, carboxyethyl group, cyanoethyl group, methoxyethyl group, ethoxyethyl group, butoxyethyl group, trifluoromethyl group, pentafluoroethyl group, 2-heptyl group, n-heptyl group, a
  • Examples of the substituent in the “optionally substituted phenyl group” and the “optionally substituted benzyl group” in the formula (2) include, for example, a methyl group, an ethyl group, and an n-propyl group.
  • the “(C1-C6) alkyl group” is a linear, branched or cyclic alkyl having 1 to 6 carbon atoms. Groups.
  • Examples of the “(C1-C6) alkyl group optionally having substituent (s)” include, for example, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, n- Pentyl group, cyclopentyl group, n-hexyl group, cyclohexyl group, hydroxypropyl group, 2-sulfoethyl group, carboxyethyl group, cyanoethyl group, methoxyethyl group, ethoxyethyl group, butoxyethyl group, trifluoromethyl group, penta A fluoroethyl group etc. are mentioned.
  • R 1 to R 4 and R 6 in the formula (2) are each independently preferably a hydrogen atom or an unsubstituted (C1-C6) alkyl group.
  • the (C1-C6) alkyl group include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, an n-pentyl group, a cyclopentyl group, and an n-hexyl group.
  • R 1 to R 4 and R 6 in the formula (2) are each independently preferably a hydrogen atom or an unsubstituted (C1-C3) alkyl group, more preferably an unsubstituted (C1-C3) alkyl group. And most preferably an ethyl group.
  • R 5 in the formula (2) is preferably a hydrogen atom or an unsubstituted (C1-C3) alkyl group, more preferably a hydrogen atom.
  • R 7 to R 20 in the formula (2) are each independently preferably a hydrogen atom, an unsubstituted (C1-C3) alkyl group or a chlorine atom, and particularly preferably a hydrogen atom.
  • Examples of the (C1-C3) alkyl group include a methyl group, an ethyl group, an n-propyl group, and an iso-propyl group.
  • Examples of the anion moiety Z 2 — of the colorant compound represented by the formula (2) include tristrifluoromethanesulfonylmethide anion, bistrifluoromethanesulfonylimide anion, trifluoromethylsulfonate, nonafluorobutylsulfonate, and the like.
  • tristrifluoromethanesulfonylmethide anion is preferred.
  • R 1 to R 4 and R 6 are each independently a hydrogen atom or an unsubstituted (C1-C6) alkyl group, more preferably all unsubstituted (C1-C3) An alkyl group, R 5 is a hydrogen atom or an unsubstituted (C1-C3) alkyl group, more preferably a hydrogen atom, R 7 to R 20 are all hydrogen atoms, and the anion portion Z 2 - is tristrifluoromethane Mention may be made of compounds which are sulfonylmethide anions, bistrifluoromethanesulfonylimide anions or trifluoromethylsulfonate.
  • R 1 to R 4 and R 6 are unsubstituted (C1-C6) alkyl groups, R 5 is a hydrogen atom, and R 7 to R 20 are all hydrogen atoms, Mention may be made of compounds in which the anion part Z 2 - is the aforementioned tristotrifluoromethanesulfonylmethide anion, bistrifluoromethanesulfonylimide anion or trifluoromethylsulfonate.
  • the colorant compound represented by the formula (1) is exemplified in the following Table 1, and the colorant compound represented by the formula (2) is exemplified in the following Table 2.
  • the colored resin composition for a color filter of the present invention The color material compound represented by Formula (1) and / or Formula (2) contained in the product is not limited to these.
  • Me is a methyl group
  • Et is an ethyl group
  • n-Bu is an n-butyl group
  • i-Bu is an iso-butyl group
  • Bz is a benzyl group
  • Ph is a phenyl group
  • CH is a cyclohexyl group
  • MeCH is Each represents a methylcyclohexyl group.
  • column Z (Z 2 ⁇ in the general formula (2)) ⁇ represents a tristotrifluoromethanesulfonylmethide anion
  • ⁇ represents a bistrifluoromethanesulfonylimide anion
  • ⁇ represents a trifluoromethylsulfonate anion.
  • the colorant compounds represented by the formulas (1) and (2) may be used alone or in any combination of two or more. Further, when these colorant compounds have low solubility in the solvent described later, they may be used after being dispersed using the same dispersing agent or dispersion aid as the optional component pigment described later.
  • the colorant compound represented by the formula (1) is superior to the colorant compound of the formula (2) in terms of developability and / or solvent resistance. More preferable. Therefore, in the resin composition of the present invention, an embodiment including the color material compound represented by the formula (1) as the color material compound is one of the more preferable embodiments.
  • Z 1 - is a tristrifluoromethanesulfonylmethide anion or a bistrifluoromethanesulfonylimide anion.
  • the colorant compound is obtained, for example, as a chloride salt by applying a known synthetic method described in Yutaka Hosoda “Theoretical Manufacturing Dye Chemistry” (pages 373-375) published by Gihodo Co., Ltd. or applying it.
  • the anion Z 1 of interest - can be obtained by addition of the corresponding salt or acid of the salt exchange - or Z 2.
  • the salt exchange will be described.
  • a compound in which the anion moiety of the formula (1) or formula (2) is a chloride ion is mixed with a solvent (for example, water, methanol, ethanol, isopropanol, acetone, N, N-dimethylformamide).
  • DMF water-soluble polar solvents
  • NMP water-soluble polar solvents
  • the solvent used may be the above solvent alone or a mixed solvent of two or more.
  • the corresponding salt or acid of the target anion moiety Z 1 — or Z 2 — is added in an amount of 0.5 to 1 equivalent of a compound in which the anion moiety of the above formula (2) is a chloride ion.
  • About 3 equivalents are added, and the mixture is stirred at a predetermined temperature (for example, 0 to 100 ° C.), and the precipitated crystals are collected by filtration.
  • the content of the colorant compound represented by the formula (1) and / or the formula (2) in 100 parts by mass of the total solid content of the colored resin composition for a color filter of the present invention is 0.1 to 60 parts by mass.
  • the ratio is preferably about 3 to 30 parts by mass, more preferably about 4 to 30 parts by mass, and most preferably 5 to 30 parts by mass.
  • the colorant compound is usually 15 to 200 parts by weight, preferably 20 to 200 parts by weight, more preferably 30 to 150 parts by weight with respect to 100 parts by weight of the unsaturated group-containing polycarboxylic acid resin. It is preferably used in a range. Further, when both the color material compound represented by the formula (1) and the color material compound represented by the formula (2) are used in combination, the ratio thereof is not particularly limited, but is represented by the formula (2). It is desirable in contrast characteristics that the content of the color material compound is not less than the content of the color material compound represented by the formula (1). That is, the content of the colorant compound represented by the above formula (1) is 0.1 to 29 parts by weight in 100 parts by mass of the total solid content of the colored resin composition for a color filter, and is represented by the formula (2).
  • the colorant compound is preferably 0.2 to 30 parts by weight, which is larger than the content of the colorant compound represented by the formula (1).
  • the color material compound represented by the formula (2) is difficult to put in the same amount or more.
  • Other performance such as brightness and tolerance is not limited to this, and may be adjusted as appropriate according to the required performance.
  • the binder resin contained in the colored resin composition for a color filter of the present invention includes the above formula (3) (wherein n represents an average value of 0 to 10, G represents a glycidyl group, P and R represent Each independently represents a hydrogen atom, a halogen atom, a (C1-C8) alkyl group or an aryl group, and each P or R may be the same or different from each other)
  • the unsaturated group-containing polycarboxylic acid obtained by reacting the polycarboxylic acid anhydride (c) with the reaction product of the unsaturated group-containing monocarboxylic acid compound (b) as described above.
  • An acid resin is used.
  • the binder resin is soluble in an alkaline developer used in the development processing step when a color filter is manufactured by a photolithography method, and has sufficient curing characteristics with a photopolymerization initiator or the like to form a good fine pattern. It is desirable to have Moreover, it is desirable that it has good compatibility with other mixed components and does not cause precipitation or aggregation when mixed with other components.
  • the resin composition of the present invention contains a pigment, a compound that functions also as a dispersant and a dispersion aid is desirable for its dispersion stability.
  • a color filter by an inkjet method since there is no image development process, what is necessary is just resin with good compatibility with another component.
  • n is 0 to 10, preferably 0 to 5.
  • the “(C1-C8) alkyl group” includes a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms.
  • a methyl group, an ethyl group, an n-propyl group examples include iso-propyl group, n-butyl group, iso-butyl group, n-pentyl group, cyclopentyl group, n-hexyl group, cyclohexyl group, n-heptyl group, n-octyl group, and cyclooctyl group.
  • the “aryl group” includes an aromatic hydrocarbon group having 6 to 14 carbon atoms, and examples thereof include a phenyl group and a naphthyl group.
  • the substitution positions of P and R are not particularly limited as long as substitution is possible.
  • individual P and R in one molecule may be the same or different, and may be different between molecules.
  • Particularly preferred P and R in the formula (3) are hydrogen atoms.
  • the unsaturated group-containing polycarboxylic acid resin is obtained by adding a polybasic acid carboxylic acid anhydride (c) to a reaction product of the epoxy resin (a) represented by the formula (3) and the unsaturated group-containing monocarboxylic acid (b). Obtained by reaction.
  • the reaction between the epoxy resin (a) and the unsaturated group-containing monocarboxylic acid (b) is preferably about 0.1 to about 0.1 to 10% of the unsaturated group-containing monocarboxylic acid with respect to 1 equivalent of the epoxy group of the epoxy resin.
  • the reaction is carried out at a ratio of 1.5 equivalents.
  • a polymerization inhibitor for example, methoquinone, hydroquinone, phenothiazine, etc.
  • the amount used is preferably 0.01 to 1 weight with respect to the reaction raw material mixture. %, Particularly preferably 0.05 to 0.5% by weight.
  • the reaction temperature is preferably 60 to 150 ° C., particularly preferably 80 to 120 ° C.
  • the reaction time is preferably 5 to 60 hours, particularly preferably 10 to 50 hours.
  • the unsaturated group-containing monocarboxylic acid (b) include acrylic acids, crotonic acid, ⁇ -cyanocinnamic acid, and cinnamic acid.
  • acrylic acids examples include acrylic acid, methacrylic acid, ⁇ -styrylacrylic acid, ⁇ -furfurylacrylic acid and the like. These unsaturated group-containing monocarboxylic acids may be used alone or as a mixture of two or more.
  • unsaturated group-containing monocarboxylic acid (b) is preferably (meth) acrylic acid, particularly preferably acrylic acid.
  • all expressions with “(meth)” such as (meth) acrylic acid or (meth) acrylate mean acrylic acid or / and methacrylic acid, or acrylate or / and methacrylate. Used in.
  • Examples of the polybasic carboxylic acid anhydride (c) to be reacted with the reaction product of the epoxy resin (a) and the unsaturated group-containing monocarboxylic acid (b) include maleic anhydride, succinic anhydride, and itaconic anhydride. Acid, methylhexahydrophthalic anhydride, tetrahydrophthalic anhydride, methylendomethylenetetrahydrophthalic anhydride, trimellitic anhydride, pyromellitic anhydride, and benzophenone tetracarboxylic anhydride, etc. Can be mentioned. Tetrahydrophthalic anhydride is preferred.
  • the amount of the acid anhydride (c) used is preferably 0.05 to 1.00 of the acid anhydride (c) per equivalent of hydroxyl group in the reaction product of (a) and (b). Equivalent amounts are reacted.
  • the reaction temperature is 60 to 150 ° C, particularly preferably 80 to 100 ° C.
  • a method for producing an unsaturated group-containing polycarboxylic acid resin is described in, for example, Japanese Patent No. 3657049, but is not limited thereto.
  • the acid value of the unsaturated group-containing polycarboxylic acid resin used in the present invention is preferably about 50 to 120 mgKOH / g.
  • the weight average molecular weight (GPC: measured by gel permeation chromatography) is usually about 500 to 50000, preferably about 1000 to 30000.
  • the above unsaturated group-containing polycarboxylic acid resin alone is usually preferred as the binder resin.
  • the content of the resin used in combination with respect to the total amount of the binder resin is about 0 to 50% by mass.
  • the combined resin includes a polymer of an ethylenically unsaturated monomer having one or more carboxy groups or hydroxyl groups, or another ethylenically unsaturated monomer and other copolymerizable aromatic hydrocarbon group or aliphatic hydrocarbon group.
  • a copolymer with an ethylenically unsaturated monomer or the like having a hydrogen atom is preferred.
  • those having an epoxy group in the side chain or terminal, and an epoxy (meth) acrylate resin obtained by adding (meth) acrylate to the epoxy group can also be used. These may be used alone or in combination of two or more.
  • Examples of the ethylenically unsaturated monomer having a carboxy group include unsaturated monocarboxylic acids such as (meth) acrylic acid, crotonic acid, ⁇ -chloroacrylic acid, ethacrylic acid, cinnamic acid; maleic acid, maleic anhydride, Unsaturated dicarboxylic acids such as fumaric acid, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, and mesaconic acid or their anhydrides; trivalent or higher unsaturated polycarboxylic acids or their anhydrides; 2- (meth) Dicarboxylic acids having 2- (meth) acryloxyethyl groups such as acryloxyethyl hexahydrophthalic acid, 2- (meth) acryloxyethyl 2-hydroxypropyl phthalate, 2- (meth) acryloxyethyl 2-hydroxyethylphthalic acid, etc. And monoesters of acids. These
  • Examples of the ethylenically unsaturated monomer having a hydroxyl group 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, 2- ( Hydroxyloxy such as hydroxyethyloxy) ethyl (meth) acrylate, glycerin mono (me
  • ethylenically unsaturated monomers examples include styrene, ⁇ -methylstyrene, o-vinyltoluene, m-vinyltoluene, p-vinyltoluene, o-chlorostyrene, m-chlorostyrene, p-chlorostyrene, p Aromatic vinyl compounds such as methoxystyrene; methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, i-propyl (meth) acrylate, n-butyl (meth) acrylate, i-butyl ( (Meth) acrylate, s-butyl (meth) acrylate, t-butyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, benzyl (meth) acrylate, paracumylphen
  • Imides 1,3-butadiene, isoprene, aliphatic conjugated dienes such as chloroprene, and the like.
  • examples include macromonomers having a mono (meth) acryloyl group at the end of the polymer molecular chain, such as polystyrene, polymethyl (meth) acrylate, poly n-butyl (meth) acrylate, and polysilicone. These ethylenically unsaturated compounds can be used alone or in admixture of two or more.
  • a compound in which an ethylenically unsaturated double bond is introduced into the side chain of the monomer copolymer can also be used as the binder resin.
  • urethane resin polyamide resin, polyimide resin, polyester resin, commercially available ACA-200M (manufactured by Daicel Corporation), ORGA-3060 (manufactured by Osaka Organic Chemical Industry Co., Ltd.), AX3-BNX02 (manufactured by Nippon Shokubai Co., Ltd.) UXE-3024, UXE-3000, ZGA-287H, TCR-1338H, ZXR-1722H, ZFR-1401H (manufactured by Nippon Kayaku Co., Ltd.) can also be used.
  • ACA-200M manufactured by Daicel Corporation
  • ORGA-3060 manufactured by Osaka Organic Chemical Industry Co., Ltd.
  • AX3-BNX02 manufactured by Nippon Shokubai Co., Ltd.
  • UXE-3024, UXE-3000, ZGA-287H, TCR-1338H, ZXR-1722H, ZFR-1401H can also be used.
  • a polymerization initiator when producing the monomer copolymer.
  • the polymerization initiator include ⁇ , ⁇ ′-azobis (isobutyronitrile), t-butyl peroctoate, di-t-butyl peroxide, benzoyl peroxide, methyl ethyl ketone peroxide, and the like.
  • the amount of the polymerization initiator used is about 0.01 to 25 parts by mass with respect to the total mass of all monomers used for the production of the copolymer.
  • the reaction temperature for producing the copolymer is preferably about 50 to 120 ° C., particularly preferably about 80 to 100 ° C.
  • the reaction time is preferably about 1 to 60 hours, more preferably about 3 to 20 hours.
  • the preferred acid value of the copolymer is about 10 to 300 mgKOH / g, and the preferred hydroxyl value is about 10 to 200 mgKOH / g. When the acid value or the hydroxyl value is 10 or less, the 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 this weight average molecular weight is less than 2000 or exceeds 400000, the sensitivity, developability and the like are lowered.
  • the content of the binder resin is usually 0.5 to 90 parts by weight, preferably 5 to 50 parts by weight, and more preferably 5 to 30 parts by weight in 100 parts by weight of the total solid content of the colored resin composition for color filters. More preferably, it is 5 to 20 parts by weight.
  • the above-mentioned binder resin is preferably an unsaturated group-containing polycarboxylic acid resin alone, and if necessary, when other resins are used in combination, 0-50 mass% with respect to the total amount of the binder resin. Within the range of is preferable. In this case, when the content of the binder resin is less than 0.5 parts by mass, the alkali developability is deteriorated, and problems such as scumming and film residue in areas other than the area where pixels are formed often occur. .
  • the photopolymerization initiator contained in the resin composition for a color filter of the present invention is preferably one having sufficient sensitivity to ultraviolet rays emitted from an ultrahigh pressure mercury lamp generally used as an exposure light source used in a photolithography method, Examples thereof include a radical polymerizable photo radical initiator, an ion curable photo acid generator or a photo base generator.
  • the photopolymerization initiator is not particularly limited.
  • Kayacure DM I Kaya Cure BDK
  • Kaya Cure BP-100 Kaya Cure BMBI
  • Kaya Cure DETX-S Kaya Cure EPA
  • Daro Cure 1173 Daro Cure 1116 (more from Merck Japan)
  • Irgacure 907, Irgacure 369, IRGACURE 379EG, IRGACURE OXE-01, IRGACURE OXE-02, IRGACURE PAG103 aboveve manufactured by BASF Japan Ltd.
  • TME-triazine manufactured by Sanwa Chemical Co., Ltd.
  • STR-110 STR-1 (manufactured by Respe Chemical Co., Ltd.) and the like.
  • a polymerization accelerator called a sensitizer that can be cured with less exposure energy may be used in combination with a photopolymerization initiator.
  • a sensitizer a known sensitizer can be appropriately used.
  • the content of the photopolymerization initiator is about 0.1 to 12 parts by mass, preferably about 1 to 10 parts by mass, in 100 parts by mass of the total solid content of the colored resin composition for a color filter.
  • the solvent contained in the colored resin composition for a color filter of the present invention is preferably an organic solvent, and is not particularly limited as long as it has sufficient dissolving power or dispersion performance with respect to the components of the colored resin composition for a color filter.
  • aromatic hydrocarbons such as benzene, toluene, xylene
  • cellosolves such as methyl cellosolve, ethyl cellosolve, butyl cellosolve
  • cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, butyl cellosolve acetate
  • Propylene glycol monoalkyl ether monoacetates such as acetate, propylene glycol monoethyl ether monoacetate, propylene glycol monobutyl ether monoacetate
  • methoxypropionic acid Propionates such as chill, ethyl methoxypropionate,
  • propylene glycol monoalkyl ether monoacetic acid esters more preferably propylene glycol mono (C1-C3) alkyl ether monoacetic acid ester solvents and / or ketone solvents are preferred. You may use these individually or in combination of 2 or more types.
  • the amount of the solvent used is usually in the range of about 40 to 10000 parts by mass, preferably about 100 to 1000 parts by mass, more preferably about 200 to 800 parts by mass with respect to 100 parts by mass of the total solid content of the colored resin composition. Is more preferable.
  • the coloring resin composition for color filters of the present invention may contain dyes, pigments, curing agents, etc. other than the colorant compound represented by the formula (1) and / or the formula (2). You may contain a thing in the range which does not lose the effect of this invention. An embodiment in which pigments are usually used in combination is one of the preferred embodiments.
  • the dye or pigment other than the colorant compound represented by the formula (1) and / or the formula (2) is not particularly limited as long as it has spectral characteristics suitable for a color filter. It can be appropriately selected from pigments and inorganic pigments.
  • dyes other than the color material compound represented by said Formula (1) and / or said Formula (2) An acid dye, a basic dye, a direct dye, a sulfur dye, a vat dye, a naphthol dye, Examples include reactive dyes and disperse dyes. Among them, those soluble in organic solvents are preferable, but insoluble dyes can be appropriately used by making a dispersion.
  • acidic dyes and basic dyes that are insoluble in organic solvents are well known methods. For example, organic amine compounds (for example, n-propylamine, ethylhexylpropionate amine, etc.) are reacted to form amine salt dyes.
  • the organic amine compound may be reacted with the sulfonic acid group to be modified into a sulfonamide group.
  • those modified dyes can also be used in the colored resin composition for a color filter of the present invention.
  • the dye has a color index of Solvent Blue 2, 3, 4, 5, 6, 23, 35, 36, 37, 38, 43, 48, 58, 59, 67, 70, 78, 98, 102, 104.
  • the organic pigment is not particularly limited.
  • Examples include lake pigments and dyed lake pigments insolubilized with the respective precipitating agents.
  • the organic pigment has a color index of 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.
  • the dye or pigment used in combination with the formula (1) or (2) is preferably a metal phthalocyanine pigment, and particularly preferably a copper phthalocyanine pigment.
  • CI Pigment Blue 15: 6 is preferable because of its good hue and durability.
  • a pigment other than the metal phthalocyanine pigment a triphenylmethane pigment (triphenylmethane skeleton-containing pigment) is preferable, and Pigment Violet 23 is more preferable.
  • the colored resin composition for a color filter of the present invention relates to blue, it is particularly preferable to use it together with known blue dyes, violet dyes, blue pigments, violet pigments and the like.
  • An embodiment in which a blue pigment, more preferably Pigment Blue 15: 6 or Pigment Violet 23, and even more preferably Pigment Blue 15: 6, is used in combination with the colorant compound of Formula (1) or (2) is one of the more preferred embodiments. It is.
  • the inorganic pigment is not particularly limited, and examples thereof include composite metal oxide pigments, carbon black, black low-order titanium oxide, titanium oxide, barium sulfate, zinc white, lead sulfate, yellow lead, bengara, ultramarine blue, bitumen, and 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 hydroxides, A metal carbonate etc. are mentioned.
  • the content thereof is 0 to 60 parts by mass, preferably 10 to 50 parts by mass, more preferably 20 parts per 100 parts by mass of the total solid content of the colored resin composition. To 50 parts by weight, and in some cases, 5 to 30 parts by weight is also preferred.
  • the use ratio of the colorant compound of the formula (1) or (2) and the above dye or pigment (preferably pigment) is not particularly limited, but is usually 10 to 1000 per 100 parts by mass of the colorant compound. It can be used within the range of parts by mass.
  • the amount is preferably 100 parts by weight or more and less than 600 parts by weight, more preferably about 200 to 550 parts by weight, and most preferably about 300 to 550 parts by weight with respect to 100 parts by weight of the colorant compound.
  • the pigment When using a pigment in the colored resin composition for a color filter of the present invention, the pigment may be dispersed using a dispersant or a dispersion aid.
  • the dispersant and the dispersion aid include a dye-based dispersant, a resin-based dispersant, a surfactant, and the like, which have good adsorptivity to the pigment.
  • the dye-based dispersant include a sulfonated product of a pigment described in Patent Document 4, a metal salt thereof, a substituted aminomethyl derivative, and the like.
  • the resin-based dispersants include nonpolar nonionic ones, but polymer resins having an acid value, an amine value, etc.
  • acrylic resins, polyurethane resins, polycarboxylic acids are used.
  • acrylic resins, polyurethane resins, polycarboxylic acids are used.
  • examples include acid resins, polyamide resins, polyester resins, and the like, for example, ED211 (manufactured by Enomoto Kasei Co., Ltd.), Ajisper PB821 (manufactured by Ajinomoto Fine Techno Co., Ltd.), Solsperse 71000 (manufactured by Avicia), and the like.
  • the surfactant is not particularly limited as long as it has the above properties.
  • Examples of the curing agent that may be added to the colored resin composition for a color filter according to 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 as others. Can be mentioned. In the present invention, any curing agent can be used, but a photopolymerizable monomer is preferred. Examples of the photopolymerization monomer include (meth) acrylate monomer and / or thiol polymerization monomer.
  • curing agents include Kayarad RTM DPHA, Kayarad RTM RP-1040, Kayarad RTM DPCA-30 (manufactured by Nippon Kayaku Co., Ltd.), UA-33H, UA-53H (manufactured by Shin Nakamura Chemical Co., Ltd.) M-8060 (manufactured by Toagosei Co., Ltd.); TEMPIC, TMMP, PEMP, DPMP (manufactured by Sakai Chemical Industry Co., Ltd.), which are commercially available thiol polymerization monomers; NC-6000, NC-6300, which are commercially available epoxy resins NC-3000, EOCN-1020, XD-1000, EPPN-501H, BREN-S, NC-7300L (above Nippon Kayaku Co., Ltd.), Celoxite 2021P, EHPE3150, Cyclomer RTM M100, Eporide RTM PB3600 ((above Daicel Chemical Industries
  • pudding Tech Sila-Ace RTM S510 (manufactured by Chisso Co., Ltd.), TEPIC (manufactured by Nissan Chemical Industries, Ltd. And the like, such as methylolated melamine, which is a commercially available melamine curing agent, Mw-30 (manufactured by Sanwa Chemical Co., Ltd.), etc. These can be used alone or in admixture of two or more.
  • the curing agent may not be included, but it is usually preferable to include it.
  • the content thereof is 1 to 80 parts by mass, preferably 5 to 30 parts by mass, more preferably 10 to 30 parts by mass with respect to 100 parts by mass of the total solid content of the colored resin composition.
  • a (meth) acrylate monomer as a curing agent.
  • a (meth) acrylate monomer alone may be used as a curing agent, or another curing agent may be used in combination with the (meth) acrylate monomer.
  • the (meth) acrylate monomer as the curing agent may be monofunctional or polyfunctional having two or more (meth) acryloyl groups.
  • curing agent in this invention it is preferable to contain the polyfunctional (meth) acrylate monomer which has 2 or more of (meth) acryloyl groups normally.
  • the polyfunctional (meth) acrylate monomer is preferably a polyfunctional (meth) acrylate monomer having 2 to 6 (meth) acryloyl groups (referred to as 2 to 6 functional (meth) acrylate monomer), more preferably 3 to It is a hexafunctional (meth) acrylate monomer.
  • the content ratio of the polyfunctional (meth) acrylate monomer in the total amount of the curing agent is usually about 20 to 100% by mass, preferably about 30 to 100% by mass, and more preferably about 40 to 100% by mass. 100% is most preferred.
  • the use ratio of the curing agent and the unsaturated group-containing polycarboxylic acid resin in the binder resin is not particularly limited as long as it is within the range of the above-mentioned content ratio, but usually the unsaturated group-containing polycarboxylic acid resin.
  • the amount of the curing agent used is 0.2 to 10 parts by mass, preferably 0.5 to 5 parts by mass, more preferably 1 to 3 parts by mass.
  • Y 1 to Y 4 are each independently an unsubstituted (C1-C3) alkyl group
  • X 1 is a carboxy group
  • X 2 to X 5 are each independently hydrogen atoms
  • Z 1 - is A compound which is a tristotrifluoromethanesulfonylmethide anion, a bistrifluoromethanesulfonylimide anion or a trifluoromethanesulfonate anion
  • the colorant compound represented by the formula (2) is represented by the formula (2):
  • R 1 to R 4 R 6 is unsubstituted (C1-C6) alkyl
  • R 5 is a hydrogen atom
  • all of R 7 ⁇ R 20 is a hydrogen atom
  • anion Z 2 - is Torisutorifu It is a compound which is an olomethanesulfonylmethide anion, a bistrifluoromethanesulfonylimide anion or
  • the metal phthalocyanine pigment is a copper phthalocyanine pigment, more preferably C.I. I.
  • Z 1 - is a tristrifluoromethanesulfonylmethide anion or a bistrifluoromethanesulfonylimide anion
  • thermosetting resin composition As a pixel manufacturing method using the colored resin composition for a color filter of the present invention, there are a photolithography method and an ink jet method as described above.
  • the former uses a photopolymerization initiator and a photosensitive resin composition excellent in developability is used, and the latter does not necessarily require a photopolymerization initiator and a thermosetting resin composition is used. That is, a thermal polymerization initiator is generally used together with a thermosetting resin composition used in the ink jet method or the like, but a photopolymerization initiator may be used in combination as necessary.
  • the thermal polymerization initiator include the same compounds as the polymerization initiator used in the production of a monomer copolymer as a binder resin.
  • the colored resin composition for a color filter of the present invention is produced by mixing and stirring the above components with a dissolver or a homomixer.
  • the dye or pigment to be added as required is low in solubility in a solvent, after adding a dispersion by a disperser such as a paint shaker using the dispersant, in addition to the colored resin composition Mix. Then, in order to remove foreign substances, etc., it may be microfiltered with a filter or the like.
  • the colored resin composition for a color filter of the present invention may further include various additives, for example, a filler, a surfactant, a thermal polymerization inhibitor, an adhesion promoter, an antioxidant, an ultraviolet absorber, if necessary. An agglomeration inhibitor or the like may be contained.
  • the content of these additives in the total solid content of 100 parts by mass of the resin composition is usually 0 to 30 parts by mass, preferably about 0 to 20 parts by mass.
  • the colored resin composition for a color filter of the present invention is formed on a substrate such as a glass substrate or a silicon substrate by a method such as spin coating, roll coating, slit and spin, die coating, or bar coating.
  • the coating is applied to a thickness of 0.1 to 20 ⁇ m, preferably 0.5 to 5 ⁇ m, and, if necessary, in a vacuum chamber, for example, at a temperature of 23 to 150 ° C. for 1 to 60 minutes, more preferably at a temperature of 60
  • the film is dried under reduced pressure at ⁇ 120 ° C.
  • An active energy ray (for example, electron beam or ultraviolet ray is preferable, preferably ultraviolet ray) is irradiated through a predetermined mask pattern which is a general photolithography method, and a surfactant aqueous solution, an alkaline aqueous solution, or a surfactant and an alkali are used.
  • a predetermined mask pattern which is a general photolithography method
  • a surfactant aqueous solution, an alkaline aqueous solution, or a surfactant and an alkali are used.
  • Develop with mixed aqueous solution examples of 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 or a combination thereof may be used.
  • the unirradiated portion is removed by development, rinsed with water, and post-baked (for example, 1 to 120 minutes at a temperature of 130 to 300 ° C., more preferably 1 to 30 minutes at a temperature of 150 to 250 ° C.).
  • a blue pixel that is a cured product is obtained.
  • Development is usually carried out at 10 to 50 ° C., preferably 20 to 40 ° C., usually 30 to 600 seconds, preferably 30 to 120 seconds.
  • the surfactant include polyoxyalkylene alkyl ethers, among which polyoxyethylene alkyl ethers are preferred.
  • the alkali agent include sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, diethanolamine, tetramethylammonium hydroxide and the like. In the development of the present invention, it is preferable to use an aqueous solution containing both an alkali agent and a surfactant.
  • the cured product of the colored resin composition for a color filter of the present invention provides a patterned blue pixel color filter suitable for a liquid crystal display device, an organic EL display, or a solid-state imaging device used for a digital camera, Those equipped with this color filter are also included in the present invention.
  • the liquid crystal display device is manufactured, for example, with a structure in which a backlight, a polarizing film, a display electrode, a liquid crystal, an alignment film, a common electrode, the color filter of the present invention, a polarizing film, and the like are laminated in this order.
  • the organic EL display is produced by forming the color filter of the present invention on either the top or bottom of a multilayer organic light emitting device.
  • the solid-state imaging device is produced, for example, by providing a layer of the color filter of the present invention on a silicon wafer provided with transfer electrodes and photodiodes, and then laminating microlenses.
  • spectral transmittance was measured by a spectrophotometer “Shimadzu Corporation UV-3150”, and chromaticity in an XYZ color system was calculated to evaluate the resistance of a colored body. Moreover, unless otherwise indicated in an Example, a part shows a mass part.
  • Synthesis Example 2 (Synthesis of Colorant Compound 1-2) A 100 ml beaker was charged with 1 part of rhodamine B and 20 parts of water, and stirred at room temperature for 30 minutes. A solution prepared by dissolving 1 part of a potassium salt of bistrifluoromethanesulfonium imide in 1 part of dimethylformamide was added dropwise thereto and stirred for 3 hours. The precipitated compound was collected by filtration, washed with water and dried to obtain 0.7 part of colorant compound 1-2. Maximum absorption wavelength: 560 nm (cyclohexanone)
  • Synthesis Example 3 (Synthesis of Colorant Compound 1-3) A 2000 ml beaker was charged with 4 parts of rhodamine B and 750 parts of water and stirred at room temperature for 30 minutes. A solution prepared by dissolving 1.5 parts of a lithium salt of trifluoromethanesulfonic acid in 10 parts of water was added dropwise thereto and stirred for 3 hours. The precipitated compound was collected by filtration, washed with water and dried to obtain 3.5 parts of colorant compound 1-3. Maximum absorption wavelength: 560 nm (cyclohexanone)
  • PGMEA propylene glycol monomethyl ether monoacetate
  • Synthesis Example 8 (Comparative Binder Resin: Synthesis of Copolymer (C))
  • 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 (C) had a polystyrene equivalent weight average molecular weight of 18,000 and an acid value of 152 mgKOH / g.
  • Example 1 to 6 Comparative Examples 1 to 6
  • C. I. Pigment Blue 15: 6 / Addisper PB821 / Solsperse 5000 / PGMEA were mixed at a composition ratio of 15.0 / 6.0 / 1.0 / 78.0 (mass ratio), and then 400 g of 0.3 mm zirconia beads were added.
  • the blue pigment dispersion 1 was obtained by performing a treatment for 60 minutes with a paint shaker and filtering.
  • a substrate for evaluation of heat resistance was produced by applying each colored resin composition to a glass substrate in the same manner as described above, exposing the entire surface, and performing a post-bake treatment at 200 ° C. for 5 minutes. In both cases, a color filter substrate having clear color characteristics was obtained. Thereafter, each evaluation was performed as described below.
  • Heat resistance The spectral transmittance of the evaluation substrate was measured before and after the treatment at 200 ° C. for 120 minutes, and the color difference ( ⁇ Eab) was calculated and evaluated. The smaller the color difference, the better.
  • Solvent resistance Even when immersed in NMP used as a solvent for the material of the liquid crystal alignment film, it is required that there is no spectral change. The spectral transmittance before and after the immersion of the evaluation substrate was measured, and the color difference ( ⁇ Eab) was calculated and evaluated. The smaller the color difference, the better.
  • Table 4 shows the results of patterning (shape, residue), heat resistance and solvent resistance.
  • each of Examples 1 to 6 of the present invention showed the same or superior results in patterning evaluation, heat resistance, and solvent resistance evaluation as compared to the corresponding Comparative Examples 1 to 6. Yes.
  • Examples 1 and 2 are most preferable because they are excellent in patterning (shape, residue), heat resistance, and solvent resistance.
  • the colored resin composition of the present invention containing a specific colorant compound and an unsaturated group-containing polycarboxylic acid resin, etc., it shows good patternability with little residue and the like with clear color characteristics, and The present inventors have found that a color filter pixel excellent in heat resistance and solvent resistance can be provided.

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  • Macromonomer-Based Addition Polymer (AREA)

Abstract

La présente invention concerne : une composition de résine colorée pour des filtres colorés qui comprend (i) une matière colorante consistant en un colorant acide spécifique contenant un squelette de xanthène ou un colorant spécifique contenant un squelette de triarylméthane, (ii) une résine liante consistant en une résine d'acide polycarboxylique ayant des groupes insaturés que l'on obtient en soumettant un produit de réaction de (a) une résine époxy spécifique avec (b) un composé acide monocarboxylique ayant un groupe insaturé à une réaction avec (c) un anhydride d'acide carboxylique polybasique, (iii) un initiateur de photopolymérisation et (iv) un solvant ; un produit durci de celle-ci ; des filtres colorés contenant le produit durci ; des dispositifs d'affichage équipés des filtres colorés ; etc. Le colorant acide spécifique contenant un squelette de xanthène est, par exemple, un colorant dérivé de la Rhodamine B par le remplacement de l'anion chlorure (Cl-) par un anion à teneur en fluoroalkyle spécifique, tandis que le colorant spécifique contenant un squelette de triarylméthane est, par exemple, un colorant dérivé du Bleu Basique 7 par le remplacement de l'anion chlorure (Cl-) par un anion à teneur en fluoroalkyle spécifique. L'anion à teneur en fluoroalkyle spécifique est un anion tris(trifluorométhane-sulfonyl)méthide, un anion bis(trifluorométhanesulfonyl)imide, un anion trifluorométhanesulfonate, ou similaires. La composition de résine a des caractéristiques de couleur claire-pureté, montre une bonne aptitude à la formation de motif avec peu de résidu, et fournit des filtres colorés qui présentent d'excellentes résistance à la lumière, résistance à la chaleur et résistance aux solvants, etc.
PCT/JP2012/004579 2011-07-19 2012-07-18 Composition de résine colorée pour des filtres colorés Ceased WO2013011687A1 (fr)

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US20150322265A1 (en) * 2012-03-30 2015-11-12 Kyung-In Synthetic Co., Ltd. Xanthene-based purple dye compound, coloring resin composition for color filter containing same and color filter using same
JP2016014736A (ja) * 2014-07-01 2016-01-28 三菱化学株式会社 着色樹脂組成物、カラーフィルタ、液晶表示装置及び有機ｅｌ表示装置
JP2017032748A (ja) * 2015-07-31 2017-02-09 桂 入交 個体撮像素子のカラーフィルター用着色感放射線組成物
CN107656423A (zh) * 2016-07-26 2018-02-02 株式会社Lg化学 感光性树脂组合物和含有该感光性树脂组合物的滤色器
CN107656421A (zh) * 2016-07-26 2018-02-02 株式会社Lg化学 感光性树脂组合物和含有该感光性树脂组合物的滤色器
JP2018036644A (ja) * 2016-08-30 2018-03-08 東友ファインケム株式会社Ｄｏｎｇｗｏｏ Ｆｉｎｅ−Ｃｈｅｍ Ｃｏ．， Ｌｔｄ． 着色感光性樹脂組成物、カラーフィルターおよびこれを具備した画像表示装置
KR20180055162A (ko) * 2016-11-16 2018-05-25 동우 화인켐 주식회사 착색 감광성 수지 조성물, 이를 이용하여 제조된 컬러필터 및 화상표시장치
JP2018112736A (ja) * 2017-01-13 2018-07-19 東友ファインケム株式会社Ｄｏｎｇｗｏｏ Ｆｉｎｅ−Ｃｈｅｍ Ｃｏ．， Ｌｔｄ． 着色感光性樹脂組成物、これを利用して製造されたカラーフィルターおよび画像表示装置
US10175574B2 (en) 2014-01-31 2019-01-08 Fujifilm Corporation Coloring composition, and cured film, color filter, pattern forming method, method for manufacturing color filter, solid-state imaging device, image display device, and dye multimer, each using the coloring composition
CN110114701A (zh) * 2016-12-19 2019-08-09 富士胶片株式会社 波长转换用发光性树脂组合物及其制造方法、以及波长转换部件及发光元件
JP2021080434A (ja) * 2019-11-18 2021-05-27 保土谷化学工業株式会社 キサンテン色素、該色素を含有する着色組成物、カラーフィルター用着色剤およびカラーフィルター

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US20150322265A1 (en) * 2012-03-30 2015-11-12 Kyung-In Synthetic Co., Ltd. Xanthene-based purple dye compound, coloring resin composition for color filter containing same and color filter using same
JP2015071743A (ja) * 2013-09-06 2015-04-16 富士フイルム株式会社 着色組成物、硬化膜、カラーフィルタ、カラーフィルタの製造方法、固体撮像素子、画像表示装置、ポリマー、キサンテン色素
KR20160025612A (ko) 2013-09-06 2016-03-08 후지필름 가부시키가이샤 착색 조성물, 경화막, 컬러 필터, 컬러 필터의 제조 방법, 고체 촬상 소자, 화상 표시 장치, 폴리머, 잔텐 색소
WO2015033814A1 (fr) 2013-09-06 2015-03-12 富士フイルム株式会社 Composition colorée, film durci, filtre coloré, procédé de fabrication de filtre coloré, élément d'imagerie à semi-conducteurs, dispositif d'affichage d'image, polymère, et colorant xanthène
US10191369B2 (en) 2013-09-06 2019-01-29 Fujifilm Corporation Colored composition, cured film, color filter, color-filter manufacturing method, solid-state imaging element, image display device, polymer, and xanthene dye
US10175574B2 (en) 2014-01-31 2019-01-08 Fujifilm Corporation Coloring composition, and cured film, color filter, pattern forming method, method for manufacturing color filter, solid-state imaging device, image display device, and dye multimer, each using the coloring composition
JP2016014736A (ja) * 2014-07-01 2016-01-28 三菱化学株式会社 着色樹脂組成物、カラーフィルタ、液晶表示装置及び有機ｅｌ表示装置
JP2017032748A (ja) * 2015-07-31 2017-02-09 桂 入交 個体撮像素子のカラーフィルター用着色感放射線組成物
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KR20180024465A (ko) * 2016-08-30 2018-03-08 동우 화인켐 주식회사 착색 감광성 수지 조성물, 컬러 필터 및 이를 구비한 화상 표시 장치
JP2018036644A (ja) * 2016-08-30 2018-03-08 東友ファインケム株式会社Ｄｏｎｇｗｏｏ Ｆｉｎｅ−Ｃｈｅｍ Ｃｏ．， Ｌｔｄ． 着色感光性樹脂組成物、カラーフィルターおよびこれを具備した画像表示装置
CN107783372B (zh) * 2016-08-30 2022-03-15 东友精细化工有限公司 着色感光性树脂组合物、滤色器和具备其的图像显示装置
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CN110114701A (zh) * 2016-12-19 2019-08-09 富士胶片株式会社 波长转换用发光性树脂组合物及其制造方法、以及波长转换部件及发光元件
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JP2021080434A (ja) * 2019-11-18 2021-05-27 保土谷化学工業株式会社 キサンテン色素、該色素を含有する着色組成物、カラーフィルター用着色剤およびカラーフィルター
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