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WO2006121062A1 - Composition de résine photosensible de type à développement alcalin, substrat avec parties saillantes pour contrôle d’orientation séparé de cristaux liquides et filtre couleur obtenu à l’aide dudit substrat, et dispositif d’affichage à cristaux liquide - Google Patents

Composition de résine photosensible de type à développement alcalin, substrat avec parties saillantes pour contrôle d’orientation séparé de cristaux liquides et filtre couleur obtenu à l’aide dudit substrat, et dispositif d’affichage à cristaux liquide Download PDF

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Publication number
WO2006121062A1
WO2006121062A1 PCT/JP2006/309365 JP2006309365W WO2006121062A1 WO 2006121062 A1 WO2006121062 A1 WO 2006121062A1 JP 2006309365 W JP2006309365 W JP 2006309365W WO 2006121062 A1 WO2006121062 A1 WO 2006121062A1
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WO
WIPO (PCT)
Prior art keywords
resin composition
compound
photosensitive resin
group
alkali
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2006/309365
Other languages
English (en)
Japanese (ja)
Inventor
Sachiko Matsumoto
Hiromitsu Ito
Yuichi Otoshi
Tomohito Ishiguro
Masaaki Shimizu
Satoru Kanda
Toyofumi Shinozuka
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Adeka Corp
Toppan Inc
Original Assignee
Adeka Corp
Toppan Printing Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Adeka Corp, Toppan Printing Co Ltd filed Critical Adeka Corp
Priority to CN2006800006730A priority Critical patent/CN101006393B/zh
Priority to JP2007528296A priority patent/JP4994234B2/ja
Publication of WO2006121062A1 publication Critical patent/WO2006121062A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—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
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C08G59/681—Metal alcoholates, phenolates or carboxylates
    • C08G59/685—Carboxylates
    • 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
    • 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
    • G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—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
    • 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

Definitions

  • the present invention relates to a color filter useful for a color liquid crystal display device, an image sensor, and the like, and an alkali development type photosensitive resin composition suitably used for the production of a substrate with a liquid crystal division alignment control protrusion, and formed using the same
  • the present invention relates to a substrate with a liquid crystal division alignment control protrusion and a color filter, and a liquid crystal display device including the substrate with liquid crystal division alignment control protrusion or the color filter.
  • An alkali-developable photosensitive resin composition containing an alkali-soluble inorganic resin having an ethylenically unsaturated bond, a photopolymerization initiator, and a solvent is a key component of color liquid crystal display devices, image sensors, and the like. Widely used in the manufacture of color filters, which are parts. In recent years, with the progress of miniaturization and high functionality of electronic devices, there has been a demand for small and high definition liquid crystal display devices. Regarding color filters, it is desired to develop an alkali development type photosensitive resin composition that can form a fine pattern with high accuracy by lithography.
  • Patent Document 1 proposes a photopolymerizable unsaturated compound and an alkali-image type photosensitive resin composition containing the compound.
  • Patent Document 2 proposes a resin composition containing a polycarboxylic acid resin and a photosensitive resin composition containing the resin composition.
  • Patent Document 3 proposes an alkali-soluble unsaturated resin and a radiation-sensitive resin composition containing the resin.
  • Patent Document 1 Japanese Patent No. 3148429
  • Patent Document 2 Japanese Patent Laid-Open No. 2003-107702
  • Patent Document 3 Japanese Patent Laid-Open No. 2003-89716
  • the problem to be solved is that the alkali-developable photosensitive resin composition and the colored alkali-developable photosensitive resin, which have sufficient sensitivity and can obtain an appropriate pattern shape and fine pattern, as described above. It means that the fat composition has never been so popular.
  • an object of the present invention is an alkali development type photosensitive resin composition that is excellent in sensitivity, resolution, transparency, developability, adhesion, alkali resistance, etc., and can form a fine pattern having a good shape with high accuracy. And providing a colored alkali development type photosensitive resin composition.
  • the present invention is a photosensitive composition containing at least a binder resin, a photopolymerization initiator and a solvent, wherein the binder resin is a polyfunctional epoxy resin (A) and an unsaturated monobasic.
  • a photopolymerizable unsaturated compound obtained by reacting a polybasic acid anhydride (D) with an epoxy adduct having a structure obtained by adding the product (C2), and the epoxy adduct is For one epoxy group of the polyfunctional epoxy resin (A), the number of carboxyl groups of the unsaturated monobasic acid (B) n force O. 1 to 0.9,
  • the number n of phenolic hydroxyl groups of the cyclic terpene structure skeleton-containing phenol compound (C1) and Z or aliphatic alkylphenol compound (C2) is 0.1 to 0.9, and
  • n and n are 0.2 to: L.
  • the structure is added at a ratio of 0.
  • the alkali development is carried out at a ratio such that the number n of acid anhydride structures of the polybasic acid anhydride (D) is 0.2 to 0.8 per one hydroxyl group of the epoxy adduct Sense of type
  • the above-mentioned object has been achieved by providing a photoabsorbent composition.
  • the present invention provides a color filter including at least a translucent substrate and a color filter layer having a plurality of pixel pattern forces, and at least one of the plurality of pixel patterns is Furthermore, it is a cured product of the alkali development type photosensitive resin composition containing a coloring material.
  • a color filter is provided.
  • the present invention provides a color filter including at least a translucent substrate and a color filter layer including a plurality of pixel patterns and a black matrix ska, wherein the black matrix further includes a color material.
  • the present invention provides a color filter characterized by being a cured product of a photosensitive resin composition.
  • the present invention provides a substrate for a liquid crystal display device comprising at least a translucent substrate and a liquid crystal split alignment control protrusion, wherein the liquid crystal split alignment control protrusion is the alkali image type photosensitive resin composition.
  • the present invention provides a substrate for a liquid crystal display device characterized by being a cured product.
  • the present invention also provides a liquid crystal display device comprising the color filter or the liquid crystal display device substrate.
  • the alkali-developable photosensitive resin composition of the present invention is excellent in sensitivity, resolution, transparency, developability, adhesion, alkali resistance, etc., and can form a fine pattern with a good shape with high accuracy.
  • the alkali development type photosensitive resin composition of the present invention contains at least a binder resin, a photopolymerization initiator and a solvent.
  • a photopolymerizable unsaturated compound is used as the noda resin contained in the alkali development type photosensitive resin composition of the present invention.
  • the photopolymerizable unsaturated compound is a reaction product obtained by esterifying a polybasic acid anhydride (D) with an epoxy adduct, and the epoxy adduct is a polyfunctional epoxy resin ( Cyclic terpene structure skeleton-containing phenolic compound (C1) and Z or aliphatic alkylphenol obtained by adding phenol or alkylphenolic compound to unsaturated monobasic acid (B) and cyclic terpene compound to A) Compound (C 2) (hereinafter referred to as the phenol compound (C) together with the cyclic terpene structure skeleton-containing phenol compound (C 1) and the aliphatic alkyl phenol compound (C-2)).
  • the above-mentioned epoxy adduct contains an unsaturated monobasic acid (B) and a phenolic compound (C) on a polyfunctional epoxy resin (A) and one epoxy group possessed by the polyfunctional epoxy resin (A).
  • Saturated monobasic acid (B) has 0.1 to 0.9 carboxyl groups, phenol compound
  • the number n of phenolic hydroxyl groups possessed by the product (C) is 0.1 to 0.9, and the sum of n and n is
  • the number n of the carboxyl groups is preferably 0.4 to 0.9 with respect to one epoxy group of the polyfunctional epoxy resin (A).
  • n of the phenolic hydroxyl groups is preferably 0.1 to 0.6.
  • the sum is preferably 0.8 to 1.0.
  • the ester mixture of the epoxy adduct and the polybasic acid anhydride (D) is the number of acid anhydride structures of the polybasic acid anhydride (D) per one hydroxyl group of the carotenoid with epoxy n.
  • the number is preferably 0.4 to 0.7 per one hydroxyl group of the adduct.
  • One preferred polyfunctional epoxy resin (A) used in the preparation of the alkali development type photosensitive resin composition of the present invention is one of the alkylidene bisphenols represented by the following general formula (I): Polyglycidyl ether type epoxy resin.
  • X is a direct bond, a methylene group, an alkylidene group having 1 to 4 carbon atoms, an alicyclic hydrocarbon group, 0, S, SO 2, SS, SO, CO, OCO, or The substituent represented by
  • the alkylidene group may be substituted with a halogen atom, and R and R are
  • 1 2 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 2 to 5 carbon atoms, or a halogen atom, an alkyl group, an alkoxy group, and The alkenyl group may be substituted with a halogen atom.
  • N represents 0 or an integer of 1 to 10.
  • Y is a hydrogen atom, carbon atom number 1 to: LO alkyl group or carbon atom number 1 to: phenyl group or carbon atom number that can be substituted by LO alkoxy group 3 to LO; ⁇ ⁇ ⁇ represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkyl group having 2 to 10 carbon atoms, or a halogen atom, an alkyl group, The alkoxy group and the alk group may be substituted with a halogen atom, and ⁇ represents a number of 0 to 5.
  • the alkylidene group having 1 to 4 carbon atoms represented by X includes methylidene, ethylidene, propylidene, isopropylidene, butylidene, isobutylidene, trifluoromethylidene, ditrifluoroisopropylidene.
  • the halogen atom with which these alkylidene groups may be substituted include fluorine, chlorine, bromine and iodine.
  • Examples of the alicyclic hydrocarbon group represented by X include cyclopentylidene, 3-methylcyclopentylidene, cyclopentylidene, cyclohexylidene, cyclohexylidene,
  • Examples include 3-methylcyclohexylidene, 3,3-dimethylcyclohexylidene, and 3,5-dimethylcyclohexylidene.
  • alkyl group having 1 to 5 carbon atoms represented by R and R examples include methyl, ethyl, and
  • Mouth pill isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, amyl, isoamyl, tert-amyl, monofluoromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, perfluoroethyl, etc. It is done. Number of carbon atoms represented by R and R
  • alkoxy group of 1 to 8 examples include methoxy, ethoxy, propyloxy, butyloxy, methoxetyl, ethoxyethyl, propyloxycetyl, methoxyethoxyethyl, ethoxy ethoxyethyl, propyloxyethoxyethyl, methoxypropyl and the like.
  • alkenyl group having 2 to 5 carbon atoms represented by 1 and R examples include bulle, allyl, butyl.
  • halogen atom examples include fluorine, chlorine, bromine, and iodine.
  • X in the general formula (I) may be a substituent represented by the above [Chemical Formula 2]!
  • the alkyl group having 1 to 10 carbon atoms represented by ⁇ includes methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, amino , Isoamyl, tertamyl, hexyl, heptyl, octyl, isooctyl, tertiary octyl, 2-ethyl hexyl, noel, isonoel, decyl, isodecyl, monofluoromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl And perfluoroethylene.
  • Examples of the alkoxy group having 1 to 10 carbon atoms represented by Z include methoxy, ethoxy, propyloxy, butyloxy, methoxyethyl, ethoxyethyl, propoxyxetyl, methoxyethoxyethyl, ethoxyethoxyethyl, propyloxyethoxyethyl, methoxypropyl and the like. Is mentioned.
  • Examples of the alkenyl group having 2 to 10 carbon atoms represented by Z include bur, aryl, buture, and probe.
  • Examples of the halogen atom represented by Z and the halogen atom which may substitute the alkyl group, alkoxy group and alk group represented by Z include fluorine, chlorine, bromine and iodine.
  • the substituents represented by the above [Chemical Formula 2] the phenyl group represented by Y and the cycloalkyl group having 3 to 10 carbon atoms may be substituted.
  • the alkyl group and alkoxy group having 1 to 10 carbon atoms may be substituted. Examples thereof include those exemplified as the alkyl group having 1 to 10 carbon atoms and the alkoxy group represented by Z.
  • Examples of the cycloalkyl group having 3 to 10 carbon atoms represented by Y include cyclopropinole, cyclobutinole, cyclopentinole, cyclohexinole, methinorecyclohexenole, cycloheptyl, cyclooctyl, cyclonol, cyclodealkyl and the like.
  • alkylidene bisphenol polyglycidyl ether type epoxy resins represented by the above general formula (I) those in which X is a propylidene group; R and Z or R, particularly R and R are hydrogen atoms Some are preferred; n is 0 or 1 to 5, in particular 0 or 1.
  • alkylidene bisphenol polyglycidyl ether type epoxy resin represented by the general formula (I) include the following compounds No. 1 to No. 6. However, the present invention is not limited by the following compounds.
  • the multifunctional epoxy resin (A) used in the preparation of the alkali development type photosensitive resin composition of the present invention includes a phenol novolac epoxy resin represented by the following general formula (II): Fat is also preferably used.
  • R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 8 carbon atoms.
  • alkenyl group having 2 to 5 carbon atoms, halogen atom or (4-glycidylo Xylphenol) -2,2-Dimethylmethylidene group, alkyl, alkoxy and alkenyl groups may be substituted with halogen atoms.
  • R is hydrogen or glycidyl.
  • n 0 or an integer of 1 to 10.
  • alkyl group having 1 to 5 carbon atoms represented by R examples include methyl, ethyl, propyl,
  • Examples include isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, amyl, isoamyl, tert-amyl, monofluoromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, perfluoroethyl and the like.
  • Examples of the xy group include methoxy, ethoxy, propyloxy, butyloxy, methoxyethyl, ethoxyethyl, propyloxycetyl, methoxyethoxyethyl, ethoxyethoxysilane, propyloxyethoxyethyl, methoxypropyl and the like.
  • alkenyl group having 2 to 5 elementary atoms examples include bur, allyl, butyr, ethul, and propylene.
  • R is water.
  • R is a glycidyloxyphenyl group
  • n is 0 or 1 to 5
  • phenol novolac type epoxy resin represented by the general formula (II) include the following compounds ⁇ .7 to 10 ⁇ .10. However, the present invention is not limited by the following compounds.
  • polyfunctional epoxy resin (A) used for the preparation of the alkali development type photosensitive resin composition of the present invention include compounds Nos. Ll to ⁇ ⁇ ⁇ .
  • the present invention is not limited by the following compounds.
  • Examples of the unsaturated monobasic acid (B) used in the preparation of the alkali development type photosensitive resin composition of the present invention include acrylic acid, methacrylic acid, crotonic acid, cinnamic acid, sorbic acid, hydroxy Shetinore Metatalylate, Malate, Hydroxyethylenolate Tallate 'Malate, Hydroxy Propinoremetatalylate 'maleate, hydroxypropinoreatalylate' malate, dicyclopentagenate, maleate or polyfunctional (meth) acrylate with one carboxyl group and two or more (meth) attalyloyl groups. It is done.
  • a polyfunctional (meta) having one carboxyl group and two or more (meth) atalyloyl groups are two or more (meth) atalyloyl groups.
  • Atalylate is, for example, a reaction between a polyfunctional (meth) acrylate having one hydroxyl group and two or more (meth) attaylyl groups in one molecule and a dibasic acid anhydride or carboxylic acid. It can be obtained by scooping.
  • a polyfunctional (meta) having one carboxyl group and two or more (meth) atalyloyl groups are two or more (meth) atalyloyl groups.
  • Examples of attalylate include the following compounds Nos. 18-22.
  • the cyclic terpene structure skeleton-containing phenol compound (C-1) used for the preparation of the alkali development type photosensitive resin composition of the present invention includes phenol and Z or an alkylphenol compound (hereinafter, both of them).
  • phenols Also collectively referred to as phenols
  • 1 to 3 moles especially 1 mole of cyclic terpene compound attached to 1 mole is preferable.
  • it can be used by adding 4 to 5 moles of cyclic terpene compound to 1 mole of phenol.
  • the cyclic terpene compound may be a monocyclic terpene compound or a bicyclic terpene compound. Specific examples thereof include compounds shown in the following [Chemical 26] to [Chemical 30].
  • phenols examples include phenol, cresol, xylenol, propylphenol, butylphenol, pentylphenol, amylphenol, octylphenol, norphenol, dodecylphenol, methoxyphenol, black mouth phenol, and bromophenol. 4-isopropyl-1-3-methylphenol, 5-methyl-2- (1-methylethyl) phenol and the like.
  • the addition of the cyclic terpene compound to the phenols is preferably a ratio of 0.5 to 5 moles, more preferably 0.8 to 1.5 moles of the cyclic terpene compound per mole of the phenols.
  • a ratio of 0.5 to 5 moles, more preferably 0.8 to 1.5 moles of the cyclic terpene compound per mole of the phenols For example, by reacting at 40 to 160 ° C. for 1 to L0 hours in the presence of an acid catalyst. This reaction can also be carried out in a solvent such as aromatic hydrocarbons, alcohols, ethers and the like.
  • the ratio of the cyclic terpene compound used is less than 0.5 mol or more than 5 mol with respect to 1 mol of the phenols, the reaction by-product described later tends to occur, such being undesirable.
  • Examples of the acid catalyst used in the reaction include hydrochloric acid, sulfuric acid, phosphoric acid, polyphosphoric acid, boron trifluoride or a complex thereof, and activated clay.
  • the structure of the above-mentioned cyclic terpene structure skeleton-containing phenolic compound obtained by adding 1 to 3 moles of the above-mentioned cyclic terpene compound to 1 mol of the above phenols was subjected to an addition reaction of both types.
  • a variety of forces depending on the site can be represented by the following general formula (III).
  • R and R are each independently a hydrogen atom, halogen atom, alkyl group,
  • the compound has a purity of preferably 70% or more, more preferably 80% or more, it can be used effectively. This degree of purity can be easily achieved by methods such as vacuum distillation. Use of a material having a purity of less than 70% is not preferable because the viscosity increases and the reaction product gels.
  • examples of the impurities include terpene polyhydric phenols, multiterpene monophenols, terpene polymers, high molecular weight substances, unreacted raw materials, and the like.
  • Them Specific examples are shown in the following [Chemical Formula 33] (ii) to (ha).
  • Examples of the aliphatic alkylphenol compound (C-2) used in the preparation of the alkali-developable photosensitive resin composition of the present invention include cresol, xylenol, propylphenol, butylphenol, pentylphenol, and dipentyl.
  • Linear alkyl phenols such as phenol, amylphenol, hexylphenol, heptylphenol, octylphenol, dioctylphenol, norphenol, dinolphenol, dodecylphenol, 4-isopropyl-1-methylphenol, 5-methyl2 — Aliphatic rings such as branched alkylphenols such as (1-methylethyl) phenol, p-cyclopentylphenol, p-cyclohexylphenol, p- (4-methylcyclopentyl) phenol, p- (4-methylcyclohexyl) phenol Formula al Rufuenoru. These long-chain alkylphenols and alicyclic alkyl phenols having 8 or more carbon atoms among virtuous preferable.
  • D) includes succinic anhydride, maleic anhydride, phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, 2, 2, 1 3, 3, monobenzophenone tetracarboxylic anhydride , 3, 3, -4, 4, monobenzophenone tetracarboxylic anhydride, ethylene glycol bisanhydro trimellitate, glycerol tris anhydro trimellitate, methyl tetrahydrophthalic anhydride, tetrahydrophthalic anhydride , Nadic acid anhydride, methyl nadic acid anhydride, trialkyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, 5- (2,5 dioxotetrahydrofuryl) -3-methyl-3 cyclohexene mono 1,2 dicarboxylic acid anhydride ,bird Alkyltetrahydrophthalic anhydride-maleic anhydride adduct, dodecy
  • Monoanhydrides such as methyl hymic anhydride, biphthalic dianhydride, 3, 3 ', 4, 4'-biphenyltetracarboxylic dianhydride, 3, 3', 4, 4, diphenyltetra Sulfonic acid dianhydride, 4,4'-oxydiphthalic acid dianhydride, 2, 3, 5 tricarboxycyclopentyl acetic acid dianhydride, 1, 2, 3, 4-cyclopentanetetracarboxylic dianhydride, methylhexahi Examples thereof include dianhydrides such as drophthalic anhydride and butanetetracarboxylic dianhydride, and it is preferable to use a monohydrate and a dianhydride in combination, or to use a dianhydride alone.
  • the noinda resin is obtained by further reacting an epoxy compound (E) with the photopolymerizable unsaturated compound obtained using the components (A) to (D). May be used.
  • the epoxy compound (E) is used for adjusting the acid value and can be used for improving the developability of the alkaline development type photosensitive resin composition of the present invention.
  • Epoxy compounds (E) that can be used include glycidyl metatalylate, methyl daricidyl ether, ethyl daricidyl ether, propyl glycidyl ether, isopropyl glycidyl ether, butyl daricidyl ether, isobutyl daricidyl ether, t --Butyl daricidyl ether, pentyl glycidyl ether, hexyl glycidyl ether, peptyl glycidyl ether, octyl daricidyl ether, nonyl daricidyl ether, decyl glycidyl ether, undecyl glycidyl ether, dodecyl glycidyl ether, tridecyl glycidyl ether , Tetradecyl glycidyl ether, pentadecyl gly
  • the alkali developing type rosin composition of the present invention has an acid value of 60 to 120 mgKOH / g, particularly 65 to 85 mgKOHZg, and the amount of the epoxy compound (E) used is preferably the acid value described above. U, prefer to meet.
  • the content of the photopolymerizable unsaturated compound which is a reaction product obtained by reacting the components (A) to (D) and reacting the component (E) as necessary, is as follows. 1 to 70% by weight, particularly 3 to 30% by weight, based on the total weight of the total solid content excluding the solvent from the alkali development type photosensitive composition of the invention.
  • the photopolymerization initiator contained in the alkali development type photosensitive resin composition of the present invention conventionally known compounds can be used.
  • R represents R, OR, COR, SR, CON
  • R represents R, OR, COR, SR, NRR, R represents R, OR, COR,
  • SR, NRR, and R and R ′ represent an alkyl group, an aryl group, an aralkyl group or a heterocyclic group, and these may be substituted with a halogen atom and Z or a heterocyclic group.
  • the alkylene part of the alkyl group and the aralkyl group may be interrupted by one or more selected from an unsaturated bond, an ether bond, a thioether bond, and an ester bond strength, and R and R ′ together form a ring.
  • N is 0-5.
  • 1 1 2 3 1 represents a gen atom or an alkyl group
  • Z represents an oxygen atom or a sulfur atom
  • m and n each represent a number of 1 to 4
  • R 1 represents R, OR, COR, SR, Represents CONRR or CN, R,
  • R 1 2 represents R, OR, COR, SR, NRR, and R 1 represents R, OR, COR, SR, NRR, respectively.
  • R represents a diol residue or a dithiol residue.
  • the content of the photopolymerization initiator occupies the total mass of all solids excluding the solvent from the alkali-developable photosensitive resin composition.
  • the proportion is preferably 0.1 to 30% by mass, particularly preferably 0.5 to 5% by mass.
  • Examples of the solvent contained in the alkali-developable photosensitive resin composition of the present invention include methanol, ethanol, ethyl acetate sorb, ethyl acetate sorb acetate, diglyme, cyclohexanone, ethylbenzene, xylene, and acetic acid.
  • the alkali-developable photosensitive resin composition of the present invention can further use a plasticizer.
  • the plasticizer is not particularly limited, and plasticizers usually used for plastics and the like can be used.
  • the plasticizer is, for example, an alkyl ester of a polyvalent carboxylic acid; obtained by condensing a polyvalent carboxylic acid and a polyhydric alcohol.
  • Polyester blocked with Z or monovalent carboxylic acid Phosphate ester such as triphenyl phosphate, tricresyl phosphate, trixylyl phosphate; Epoxy compound such as epoxidized soybean oil, epoxidized fatty acid octyl ester, epoxy resin; Examples include polyether compounds such as ether polyols, polyetheramines, and polyether esters.
  • plasticizer examples include chlorinated paraffin, polyethylene, ethylene-acetate copolymer, polyether ester, ethylene acrylic acid copolymer, ionomer, ethylene acrylic ester copolymer, ethylene-methacrylic ester copolymer.
  • Polymer Polypropylene, Polystyrene, Poly-a-methylstyrene, a-Methylenostyrene-vininoretanolene copolymer, Styrene-butadiene copolymer, Styrene-methyl methacrylate copolymer, Styrene- (meth) acrylic acid copolymer Polymer, Styrene-acrylonitrile copolymer, Styrene-one acrylate copolymer, Polymethyl acrylate, Polymethyl methacrylate, Polyethyl acrylate, Polyethyl methacrylate, Polybutyl acrylate, Polybutyl methacrylate Methyl meta Relay to methacrylate copolymer, methyl methacrylate-ethyl acrylate copolymer, 2-ethylhexyl acrylate relay copolymer, poly (meth) acrylic acid, ethyl acrylate acrylate copolymer, methyl
  • a polyvalent carboxylic acid alkyl ester or a polyvalent carboxylic acid and a polyhydric alcohol are obtained, and the terminal is optionally terminated with a monohydric alcohol and Z or Polyester blocked with a monovalent carboxylic acid is preferred because it has a high melting point or soft melting point and is highly compatible with the binder resin.
  • alkyl ester of the polyvalent carboxylic acid examples include dibutyl phthalate, dioctyl phthalate, didecyl phthalate, trioctyl trimellitate, tetraoctyl pyromellitate, tetraoctyl biphenyl tetracarboxylate, and dioctyl.
  • examples include adipate, disosonol adipate, dioctyl sebacate, dioctyl azelate, trioctyl citrate and the like.
  • polyvalent carboxylic acid examples include oxalic acid, malonic acid, succinic acid, dartaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, itaconic acid, 2-methylsuccinic acid, 2 —Methyladipic acid, hydroxyethylmalonic acid, dodecanedioic acid, dimanoic acid, hydrogenated dimer acid, 1,4-cyclohexanedicarboxylic acid, cyclopentanedicarboxylic acid, 4,4'-dicyclohexyldicarboxylic acid, Castor oil fatty acid, fumaric acid, maleic acid, phthalic acid, isophthalic acid, terephthalic acid, biphenyl 2, 2, 1-dicarboxylic acid, benzene 1, 2, 3 tri-force norlevonic acid, benzene 1, 3, 5 tri-force norebon Acid, benzene-1, 2, 3, 4-t
  • Examples of the polyhydric alcohol include ethylene glycol, 1,2 propanediol, 1,3 propanediol, 2-methyl-1,3 propanediol, 2 butyl-2 ethyl 1,3 propanediol, and 1,3 butane.
  • Examples of the monohydric alcohol include methanol, ethanol, propanol, isopropyl alcohol, butanol, isobutanol, t-butanol, amyl alcohol, isoamino alcohol record, hexanol, cyclohexanol, heptanol, and n-octyl alcohol.
  • the monovalent carboxylic acids include formic acid, acetic acid, propionic acid, butyric acid, pentane. Examples include acids, cyclohexane strength rubonic acids and the like.
  • plasticizer commercially available ones can be used.
  • the content of these plasticizers is preferably 0.01 to 10 mass%, more preferably 1 to 5 mass%, based on the alkali development type photosensitive resin composition of the present invention.
  • the alkali-developable photosensitive resin composition of the present invention may contain a colorant (F).
  • a colorant examples include pigments and dyes. Which is added is not particularly limited, and either one of the pigment and the dye may be used, or both may be used in combination.
  • the pigment or dye is preferably contained by the pigment dispersion method or dye method.
  • the pigment used as the coloring material in the alkali development type photosensitive resin composition of the present invention a known pigment used in the production of a conventional color filter can be used. . Also, a plurality of pigments can be used in combination for spectral adjustment of the color filter. Below, specific examples of organic pigments are shown by curry index (C.I.) numbers. In the list below, “x” represents an integer that can be arbitrarily selected from C.I. numbers.
  • Examples of the pigment include miloli blue, iron oxide, titanium oxide, calcium carbonate, magnesium carbonate, silica, alumina, cobalt, manganese, talc, chromate, ferrocyanide, various metal sulfates, sulfides, and selenium. It is also possible to use inorganic pigments such as porcelain, phosphate ultramarine blue, bitumen, cobalt blue, cerremble one, pyridian, emerald green, cobalt green and the like.
  • These pigments can be used in combination of a plurality.
  • dyes that can be used as coloring materials include azo dyes, anthraquinone dyes, indigoid dyes, triarylmethane dyes, xanthene dyes, alizarin dyes, atalidine dyes stilbene dyes, thiazole dyes, naphthol dyes, and quinoline dyes. Nitro dyes, indamine dyes, oxazine dyes, phthalocyanine dyes, cyanine dyes, and the like. These may be used alone or in combination.
  • the content of the coloring material is a ratio to the total mass of the total solid content excluding the solvent from the alkali-developable photosensitive resin composition.
  • ⁇ 70 mass% particularly 5 to 60 mass% is preferred.
  • a monomer having an unsaturated bond, a chain transfer agent, a surfactant and the like can be used in combination.
  • Examples of the monomer having an unsaturated bond include 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, isobutyl acrylate, N-octyl acrylate, isooctyl acrylate, isononyl acrylate, and acrylic.
  • Stearyl acid methoxyethyl acrylate, dimethylaminoethyl acrylate, zinc acrylate, 1,6 hexanediol diatalylate, trimethylolpropane tritalylate, mono-2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, Butyl methacrylate, tert-butyl methacrylate, cyclohexyl methacrylate, trimethylolpropane trimetatalylate, dipentaerythritol pentatalylate, dipentaerythritol hexaatalylate, pen Taerythritol tetraatalylate, pentaerythritol triatalylate, etc.
  • chain transfer agent examples include thioglycolic acid, thiomalic acid, thiosalicylic acid, 2-mercaptopropionic acid, 3-mercaptopropionic acid, 3-mercaptobutyric acid, N- (2-mercaptopropiool) glycine, 2 Mercaptonicotinic acid, 3- [N- (2 mercaptoethyl) power ruberamoyl] propionic acid, 3- [N- (2 mercaptoethyl) amino] propionic acid, N- (3 mercaptopropiool) alanine, 2 Mercaptoethanesulfonic acid, 3-Mercaptopropanesulfonic acid, 4 Mercaptobutanesulfonic acid, Dodecyl (4-methylthio) phenyl ether, 2 Mercaptoethanol, 3 Mercapto 1,2 Propandiol, 1 Mercapto 2 Propanol, 3 Mercapto 2 Butanol, mercapto
  • surfactant examples include fluorine surfactants such as perfluoroalkyl phosphates and perfluoroalkylcarboxylates, and cation-based compounds such as higher fatty acid alkali salts, alkyl sulfonates, and alkyl sulfates.
  • fluorine surfactants such as perfluoroalkyl phosphates and perfluoroalkylcarboxylates
  • cation-based compounds such as higher fatty acid alkali salts, alkyl sulfonates, and alkyl sulfates.
  • Nonionic surfactants such as surfactants, cationic surfactants such as higher amine halogenates and quaternary ammonium salts, polyethylene glycol alkyl ethers, polyethylene glycol fatty acid esters, sorbitan fatty acid esters, fatty acid monoglycerides
  • Surfactants such as surfactants, amphoteric surfactants, and silicone surfactants can be used, and these may be used in combination.
  • thermal polymerization inhibitors such as carbole, hydroquinone, pyrocatechol, tert-butylcatechol, phenothiazine, etc .
  • plasticizer Conventional additives such as adhesion promoters, fillers, antifoaming agents, leveling agents can be covered.
  • the light source of the active light used for curing the alkali development type photosensitive resin composition of the present invention one that emits light having a wavelength of 300 to 450 nm can be used. Mercury vapor arc, carbon arc, xenon arc, etc. can be used.
  • the color filter of the present invention includes at least a translucent substrate and a color filter layer composed of a plurality of pixel patterns, and at least one of the plurality of pixel patterns contains a color material. It is characterized in that it is a cured product of the alkali development type photosensitive resin composition of the present invention, or at least a color comprising a translucent substrate, a plurality of pixel patterns, and a black matrix matrix. It is a cured product of the alkali development type photosensitive resin composition of the present invention comprising a filter layer and containing the black matrix strength coloring material.
  • the translucent substrate of the color filter of the present invention can be used without particular limitation as long as it has a certain degree of rigidity and smoothness, but when the color filter is used as a transmissive type. It is necessary to further have transparency.
  • Examples of the translucent base material that can be used include plastic films such as glass, PET (polyethylene terephthalate), and acrylic resin.
  • the alkali developing type photosensitive resin composition of the present invention, and other photosensitive films can be used in advance.
  • the black matrix may be provided by a conductive resin composition or a metal such as chromium.
  • the alkali development type photosensitive resin composition of the present invention is applied to a transparent substrate such as glass by a known means such as a spin coater, a roll coater, or a curtain coater.
  • a photomask having a predetermined pattern, and unexposed portions are removed and developed with an alkaline aqueous solution such as sodium carbonate.
  • an alkaline aqueous solution such as sodium carbonate.
  • the alkali development type photosensitive resin composition of the present invention has good exposure sensitivity.
  • a step of forming an oxygen blocking film may be provided before the exposure step for the purpose of further improving exposure sensitivity.
  • the above method can also be applied when a black matrix is provided in addition to the formation of a transparent colored film. Also, instead of coating on a substrate, an alkali development type photosensitive resin composition is once coated on a transfer support such as a so-called blanket or film supported on a cylindrical transfer cylinder, and this is transferred to the substrate. How to do it ⁇ .
  • the color filter using the alkali-developable photosensitive composition of the present invention except that the alkali-developable photosensitive composition of the present invention is used for forming a multi-color pixel pattern and / or a black matrix, It is the same as a conventional color filter and has different components depending on the application, and there are no restrictions on the configuration, but in general, a translucent base material and on the translucent base material It is composed of a plurality of colored transparent coatings arranged in a pattern and a black matrix arranged as necessary, and the white light incident on these coatings is colored in the color of the coating.
  • the color filter of the present invention When used in a liquid crystal display device, it may be provided in the liquid crystal display device in the same manner as a conventional color filter.
  • liquid crystal display devices such as liquid crystal displays, plasma displays, and electoric luminescence panels, in general, light from a light source built into the display or sunlight incident on the screen of the display is used as incident light.
  • Color screens can be displayed using colored light that has passed through the filter.
  • the color filter of the present invention can also be used as a component part of a solid-state imaging device used in an image sensor used in a solid-state imaging device such as a color video camera or a digital camera.
  • the color filter provided as a component of the solid-state image sensor serves to separate light incident from the subject. The light dispersed here is converted into an electrical signal by a light receiving element, and recording this enables recording of a color image.
  • liquid crystal display device substrate of the present invention and the liquid crystal display device of the present invention provided with the liquid crystal display device substrate will be described below.
  • the substrate for a liquid crystal display device of the present invention includes at least a translucent substrate and a liquid crystal split alignment control
  • the liquid crystal display device substrate comprising the projection for liquid crystal, wherein the liquid crystal split orientation control projection is a cured product of the alkali development type photosensitive resin composition.
  • the substrate for the liquid crystal is the same as the substrate for a conventional liquid crystal display device, except that the alkali development type photosensitive resin composition of the present invention is used for forming the liquid crystal splitting alignment control projection.
  • the liquid crystal display device substrate of the present invention When the liquid crystal display device substrate of the present invention is used in a liquid crystal display device, the liquid crystal display device may be prepared in the same manner as a conventional liquid crystal display device substrate.
  • Adeka Resin EP-4100E (Asahi Denka Kogyo Co., Ltd .: bisphenol A type epoxy resin) is represented by the general formula (I), X is a propylidene group, R and R are hydrogen atoms, and n is 0 to
  • Epicoat 834 (manufactured by Japan Epoxy Resin Co., Ltd.) is represented by the above general formula (I), wherein X is a propylidene group, R and R are hydrogen atoms, and n is a polyfunctional epoxy resin having 0 to 1 (the above compound
  • Epicoat 1032H60 (manufactured by Japan Epoxy Resin Co., Ltd .; trifluoromethane type polyfunctional epoxy resin) is represented by the general formula (II), R is a hydrogen atom, and R is glycidyloxy.
  • a polyfunctional epoxy resin having a phenyl group and n of 0 to 1 (compound No. 10).
  • Epicoat 157S70 manufactured by Japan Epoxy Resin Co., Ltd .; bisphenol A novolak type
  • the polyfunctional epoxy resin is Compound No. 17 (11 is 0 to 1).
  • XD-1000L (manufactured by Nippon Gyaku Co., Ltd .; dicyclopentagen novolac type polyfunctional epoxy resin) is Compound No. 11 (11 is 0 to 1).
  • Adeka Resin EP-4100E (Asahi Denka Kogyo Co., Ltd .; bisphenol A type epoxy resin, epoxy equivalent 190; hereinafter also referred to as Compound a-1) 154g, YP-90LL (Yasuhara Chemical Co., Ltd .; cyclic terpene monophenol) Content 90%; average molecular weight 266, hydroxyl equivalent 340; hereinafter referred to as compound c) 55.2 g and propylene glycol monomethyl etherate 90.3 g were charged and the temperature was raised to 115 ° C. Triphenylphosphine 1.05 g was gradually added and stirred at 120 ° C for 4 hours.
  • cresyl glycidyl ether (hereinafter also referred to as compound e-1) was added, the temperature was raised to 120 ° C. and held for 2 hours. Thereafter, 363 g of propylene glycol monomethyl ether acetate was collected, cooled to room temperature, and allowed to stand. Kyoichi Ward 700SL (Kyowa Chemical Industry Co., Ltd., adsorbent) was added, and after stirring for 1 hour, filtration was performed using a glass filter of 0.
  • the reaction product (photopolymerizable unsaturated compound) contained in the alkali-developable resin composition No. 1 is composed of (a) component a-1 and (B) component b and The ratio of the acid anhydride structure of compound (d) -1, component (D), to 0.6 for one hydroxyl group of the compound (C), which has a structure with compound c added, is epoxy.
  • the product was obtained by reacting the adduct with compound d1 and then reacting compound (E), compound e-1.
  • the epoxy adduct has a ratio of 0.8 carboxyl group of compound b and 0.2 phenolic hydroxyl group of compound c to 1 epoxy group of compound a-1. It has a structure added at a rate.
  • Adeka Resin EP-4100E (epoxy equivalent 190; compound a-l) 171g, Epicote 834 (Japan Epoxy Resin Co., Ltd .: epoxy equivalent 250; hereinafter also referred to as compound a-2) 25g and YP-90LL 187 g of product c) was added and heated to 115 ° C. Triphenylphosphine 1.15 g was gradually added and stirred at 120 ° C. for 4 hours. Further, 617 g of propylene glycol monomethyl ether acetate was added and cooled to 50 ° C or lower.
  • the reaction product (photopolymerizable unsaturated compound) contained in the alkali-developable resin composition No. 2 contains (A) component a-1 and compound a-2 as component (B).
  • Compound d-1 as the component (D) has an acid anhydride structure of 0.6 for one hydroxyl group of the epoxy adduct having a structure in which the compound b and the compound c as the component (C) are added. It was obtained by esterifying the epoxy adduct and compound d-1 at a ratio of
  • the above epoxy adduct has 0.45 carboxyl groups of compound b and 0.55 phenolic hydroxyl groups of compound c for one epoxy group of compounds a-1 and a-2. It has a structure added in proportion.
  • Epicoat 834 (manufactured by Japan Epoxy Resin Co., Ltd .: epoxy equivalent 250; Compound a-2) 1 90 g and YP-90LL (Compound c) 142 g were added and heated to 115 ° C. Triphenylphosphine (1.00 g) was gradually added and stirred at 120 ° C for 4 hours. Further, 521 g of propylene glycol monomethyl ether acetate was added and cooled to 50 ° C or lower. Then 2, 6— Di-tert-butyl-p-talesol 0. 358 g, benzyltriethylammonium chloride 3.58 and acrylic acid (compound b) 26.3 g were heated to 120 ° C and held for 5 hours .
  • the reaction product (photopolymerizable unsaturated compound) contained in the alkali-developable resin composition No. 3 is composed of (a) component a-2 and (B) component b and (D) component d-1 and compound d-2 have 0.6 acid anhydride structures for one hydroxyl group of the epoxy adduct having a structure to which compound (c), compound c, is added In this ratio, the epoxy adduct, compound d-1 and compound d-2 are reacted with each other, and then bisphenol A type epoxy resin (Adeka Resin EP-4100E) as component (E) It was obtained by reacting.
  • Adeka Resin EP-4100E bisphenol A type epoxy resin
  • the above epoxy adduct has a structure in which the carboxyl group of compound b is added at a ratio of 0.45 and the phenolic hydroxyl group of compound c is added at a ratio of 0.55 to one epoxy group of compound a-1. It is what you have.
  • Adeka Resin EP-4100E (epoxy equivalent 190; compound a-l) 171 g and YP-90L L (compound c) 168 g were added and heated to 115 ° C.
  • Triphenylphosphine 1.02 g was gradually added and stirred at 120 ° C for 4 hours.
  • 550 g of propylene glycol monomethyl ether acetate was added and cooled to 50 ° C or lower.
  • the reaction product (photopolymerizable unsaturated compound) contained in the alkali-developable resin composition No. 4 is composed of (a) component a-1 and (B) component b and
  • the acid anhydride structure of compound d-1 and compound d-2 as component (D) is 0.55 with respect to one hydroxyl group of the epoxy adduct having a structure to which compound c as component (C) is added. It was obtained by subjecting the epoxy adduct, compound d-1, and compound d-2 to an ester reaction at a ratio of 1 to 3.
  • the above-mentioned epoxy adduct is attached at a ratio of 0.45 of the force ruboxyl group of compound b and 0.55 of the phenolic hydroxyl group of compound c to one epoxy group of compound a-1. It has a structure.
  • Epicoat 1032H60 (manufactured by Japan Epoxy Resin Co., Ltd .; Triphenylmethane type polyfunctional epoxy resin, epoxy equivalent 173; hereinafter also referred to as compound a-3) 173g and 187g of YP-90L L (compound c)
  • Triphenylphosphine (1.8 g) was gradually added and stirred at 120 ° C for 4 hours. Further, 168 g of propylene glycol monomethyl ether acetate was added and cooled to 50 ° C or lower.
  • the reaction product (photopolymerizable unsaturated compound) contained in the alkali-developable resin composition No. 5 is composed of (a) component a-3 and (B) component b and With respect to one hydroxyl group of the epoxy adduct having a structure to which the compound c as the component (C) is added, the ratio of the acid anhydride structure of the compound d-2 as the component (D) is 0.3. It was obtained by subjecting an epoxy adduct and compound d-2 to an ester reaction. The epoxy adduct was added at a ratio of 0.45 carboxyl groups of compound b and 0.55 phenolic hydroxyl groups of compound c to one epoxy group of compound a-3. It has a structure.
  • Epicoat 157S70 manufactured by Japan Epoxy Resin Co., Ltd .; bisphenol A novolak type polyfunctional epoxy resin, epoxy equivalent 220 or less, also referred to as compound a-4) 210g and YP-90LL (compound c) 187g
  • the temperature was raised to 115 ° C.
  • the reaction product (photopolymerizable unsaturated compound) contained in the alkali-developable resin composition No. 6 is composed of (a) component a-4 and (B) component b and With respect to one hydroxyl group of the epoxy adduct having a structure to which the compound c as the component (C) is added, the ratio of the acid anhydride structure of the compound d-2 as the component (D) is 0.3. It was obtained by subjecting an epoxy adduct and compound d-2 to an ester reaction. In addition, the above epoxy adduct contains 0.45 carboxyl groups of compound b and 1 compound c for one epoxy group of compound a-4. The phenolic hydroxyl group is added at a ratio of 0.55.
  • XD-1000L (Nippon Yakuyaku Co., Ltd .; dicyclopentagen novolac polyfunctional epoxy resin, epoxy equivalent 240 or less, also referred to as compound a-5) 230g and YP-90LL (compound c) Of 179 g was added, and the temperature was raised to 115 ° C. Triphenylphosphine 1.23 g was gradually added and stirred at 120 ° C for 4 hours. Further, 135 g of propylene glycol monomethyl ether acetate was added and cooled to 50 ° C or lower.
  • trimellitic anhydride Compound d-2
  • the reaction product (photopolymerizable unsaturated compound) contained in the alkali-developable resin composition No. 7 is composed of (a) component a-5 and (B) component b and With respect to one hydroxyl group of the epoxy adduct having a structure to which the compound c as the component (C) is added, the ratio of the acid anhydride structure of the compound d-2 as the component (D) is 0.3. It was obtained by subjecting an epoxy adduct and compound d-2 to an ester reaction. The epoxy adduct was added at a ratio of 0.45 carboxyl group of compound b and 0.55 phenolic hydroxyl group of compound c to 1 epoxy group of compound a-5. It has a structure.
  • Step 1> 1, 1 Manufacture of bis (4, 1-hydroxyphenol) 1 (, 1-biphenyl) ethane
  • step 1 1, 1-bis (4, monohydroxyl) obtained in step 1 1— (1, 1, biphenyl) )
  • Ethane (37 g) and epichlorohydrin (19.5 g) were charged, and benzyltriethyl ammonium chloride (0.45 g) was added and stirred at 64 ° C for 18 hours. Subsequently, the temperature was lowered to 54 ° C., 32.6 g of a 24 mass% aqueous sodium hydroxide solution was added dropwise, and the mixture was stirred for 30 minutes.
  • Epichlorohydrin and water were distilled off, and after adding 140 g of methyl isobutyl ketone and washing with water, 1.7 g of 24 mass% sodium hydroxide sodium salt was added dropwise.
  • 1, 1 bis (4 '1 epoxypropyloxyphenyl) 1 1 1 (1,, -biphenyl) ethane obtained in step 2 49.6 g, acrylic acid 14.4 g, 2, 6 di — 0.05 g of tert-butyl p-cresol, 0.14 g of tetraptylammonium acetate and 27.4 g of propylene glycol—1-monomethyl ether—2 acetate were charged and stirred at 120 ° C. for 16 hours. After cooling to room temperature, 41.5 g of propylene glycol-1-monomethyl ether-2-acetate and 12.4 g of biphenyltetracarboxylic dianhydride were added and stirred at 120 ° C.
  • 12 g of the alkali-developable resin composition No. 1 obtained in Production Example 1 is 8 g of trimethylol propane tritalylate, 1.8 g of benzophenone, carbon black (“MA100J” manufactured by Mitsubishi Chemical Co., Ltd.) 3.2 g
  • 75 g of ethyl acetate sorb was added and stirred well to obtain a colored alkali-developable photosensitive resin composition No. 1.
  • Example 15 Production of colored alkali-developable photosensitive resin composition No. 8 13.5 g of dipentaerythritol hexatalylate, 1,2-octanedione, 1- [4- (phenolthiol) to 13.5 g of alkali-developable resin composition No. 4 obtained in Production Example 4 ) Phenol]-, 2— (o benzoyloxime) 2.5 g, carbon black 9.
  • an alkali-developable photosensitive resin composition or a colored Al-redevelopable photosensitive resin composition is prepared.
  • polybulualcohol A 5 mass% solution was coated to form an oxygen barrier film.
  • use a specified mask expose using an ultra-high pressure mercury lamp as the light source, and then immerse in 2.5 wt% sodium carbonate solution at 25 ° C for 30 seconds.
  • beta was fixed at 230 ° C for 1 hour to fix the pattern.
  • the obtained pattern was evaluated as follows. The results are shown in Tables 1 and 2.
  • the coating film after the heat treatment was immersed under the following conditions, and the appearance after the immersion was visually evaluated. The case where there was no change in the appearance and the resist was completely peeled off was marked as ⁇ , and the resist was lifted or the resist was peeled off as X.
  • the colored alkali-developable photosensitive resin composition was spin-coated (600 rpm, 7 seconds) on a glass substrate, allowed to air dry for 10 minutes, and then heated on a hot plate at 90 ° C. for 2 minutes. After that, using a mask with a pixel size of 30 mX 100 / zm, using a super high pressure mercury lamp as the light source, developing with 2.5% sodium carbonate aqueous solution, washing well, baking at 230 ° C for 30 minutes The pattern was observed with a scanning electron microscope (SEM) for the obtained pattern. The pattern with a forward taper was marked with ⁇ , the pattern with a vertical shape was marked with ⁇ , and the pattern with an overhang (reverse taper) was marked with X. The results are shown in Table 3.
  • the alkali-developable photosensitive resin compositions of Comparative Examples 1 to 3 and the colored alkali-developable photosensitive resin compositions of Comparative Examples 4 to 6 have low sensitivity, so the amount of exposure is increased. In addition, the resolution was lowered, and the film could not be formed unless the line width was 30 m or more, and the adhesion of the obtained coating film to the substrate and the alkali resistance were also remarkable.
  • the colored alkali-developable photosensitive resin compositions of Examples 15 to 17 had a pattern shape with a forward taper and good pattern formability.

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  • Nonlinear Science (AREA)
  • Mathematical Physics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Materials For Photolithography (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Epoxy Resins (AREA)
  • Optical Filters (AREA)

Abstract

L’invention porte sur une composition de résine photosensible de type à développement alcalin et une composition couleur de résine photosensible de type à développement alcalin qui sont excellentes en matière de sensibilité, de résolution, de transparence, de facilité de développement, d’adhérence, de résistance alcaline et autre et susceptibles de constituer un fin motif de forme adéquate avec une grande précision. L’invention concerne donc une composition de résine photosensible de type à développement alcalin comprenant une résine liante, un initiateur de photopolymérisation et un solvant, caractérisée en ce que la résine liante est un composé insaturé photopolymérisable élaboré par mise en réaction d’un adjuvant époxy avec une proportion spécifique d’un anhydride d’acide polybasique (D). L’adjuvant époxy présente une structure élaborée par addition, à une résine époxy polyfonctionnelle (A), d'un acide monobasique insaturé (B), et d'un composé de phénol contenant un squelette à structure terpène cyclique (C-1), élaboré par addition d’une proportion spécifique de phénol ou d’un composé alkylphénol à un composé terpène cyclique, et/ou d'un composé alkylphénol aliphatique (C-2).
PCT/JP2006/309365 2005-05-11 2006-05-10 Composition de résine photosensible de type à développement alcalin, substrat avec parties saillantes pour contrôle d’orientation séparé de cristaux liquides et filtre couleur obtenu à l’aide dudit substrat, et dispositif d’affichage à cristaux liquide Ceased WO2006121062A1 (fr)

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CN2006800006730A CN101006393B (zh) 2005-05-11 2006-05-10 碱性显影型感光性树脂组合物、带有使用它形成的液晶分割取向控制突起的基板和滤色器、以及液晶显示装置
JP2007528296A JP4994234B2 (ja) 2005-05-11 2006-05-10 アルカリ現像型感光性樹脂組成物、それを用いて形成した液晶分割配向制御突起付き基板及びカラーフィルタ、並びに液晶表示装置

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JP2005138289 2005-05-11
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JP2009229826A (ja) * 2008-03-24 2009-10-08 Toppan Printing Co Ltd カラーフィルタとそれを備えた液晶表示装置
CN103135343A (zh) * 2011-11-29 2013-06-05 第一毛织株式会社 用于滤色器的光敏树脂组合物及使用其制备的滤色器
WO2013172009A1 (fr) * 2012-05-15 2013-11-21 日本化薬株式会社 Composé de type polyester réactif et composition de résine durcissable sous l'effet d'un rayonnement d'énergie active
WO2016129324A1 (fr) * 2015-02-09 2016-08-18 富士フイルム株式会社 Composition durcissable, filtre de blocage infrarouge ayant un film de protection contre la lumière, et dispositif d'imagerie à l'état solide
WO2017150667A1 (fr) * 2016-03-02 2017-09-08 株式会社Adeka Liquide de dispersion de colorant, composition polymérisable colorée, et filtre coloré
KR20170125033A (ko) * 2015-02-26 2017-11-13 디아이씨 가부시끼가이샤 불포화기 함유 알칼리 현상성 수지 및 솔더 레지스트용 수지 재료
JP2018116151A (ja) * 2017-01-18 2018-07-26 東京応化工業株式会社 樹脂組成物、ブラックマトリクス、表示装置、及びブラックマトリクスの製造方法
JP2018180349A (ja) * 2017-04-17 2018-11-15 信越化学工業株式会社 ポジ型レジストフィルム積層体及びパターン形成方法
JP2019128438A (ja) * 2018-01-24 2019-08-01 信越化学工業株式会社 ネガ型レジストフィルム積層体及びパターン形成方法
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JP2008015393A (ja) * 2006-07-10 2008-01-24 Jsr Corp 着色層形成用感放射線性組成物、カラーフィルタおよびカラー液晶表示素子
JP2008185692A (ja) * 2007-01-29 2008-08-14 Adeka Corp ポジ型感光性樹脂組成物
KR101450705B1 (ko) 2007-05-09 2014-10-15 가부시키가이샤 아데카 신규 에폭시화합물, 알칼리 현상성 수지 조성물 및 알칼리 현상성 감광성 수지 조성물
WO2008139924A1 (fr) * 2007-05-09 2008-11-20 Adeka Corporation Nouveau composé époxy, composition de résine pouvant être développée par un composé alcalin, et composition de résine photosensible pouvant être développée par un composé alcalin
US8252512B2 (en) 2007-05-09 2012-08-28 Adeka Corporation Epoxy compound, alkali-developable resin composition, and alkali-developable photosensitive resin composition
JP2009134281A (ja) * 2007-10-31 2009-06-18 Sanyo Chem Ind Ltd 感光性樹脂組成物
JP2009229826A (ja) * 2008-03-24 2009-10-08 Toppan Printing Co Ltd カラーフィルタとそれを備えた液晶表示装置
CN103135343A (zh) * 2011-11-29 2013-06-05 第一毛织株式会社 用于滤色器的光敏树脂组合物及使用其制备的滤色器
WO2013172009A1 (fr) * 2012-05-15 2013-11-21 日本化薬株式会社 Composé de type polyester réactif et composition de résine durcissable sous l'effet d'un rayonnement d'énergie active
WO2016129324A1 (fr) * 2015-02-09 2016-08-18 富士フイルム株式会社 Composition durcissable, filtre de blocage infrarouge ayant un film de protection contre la lumière, et dispositif d'imagerie à l'état solide
JPWO2016129324A1 (ja) * 2015-02-09 2017-10-05 富士フイルム株式会社 硬化性組成物、遮光膜付き赤外光カットフィルタ、及び、固体撮像装置
KR102371057B1 (ko) 2015-02-26 2022-03-07 디아이씨 가부시끼가이샤 불포화기 함유 알칼리 현상성 수지 및 솔더 레지스트용 수지 재료
KR20170125033A (ko) * 2015-02-26 2017-11-13 디아이씨 가부시끼가이샤 불포화기 함유 알칼리 현상성 수지 및 솔더 레지스트용 수지 재료
WO2017150667A1 (fr) * 2016-03-02 2017-09-08 株式会社Adeka Liquide de dispersion de colorant, composition polymérisable colorée, et filtre coloré
JPWO2017150667A1 (ja) * 2016-03-02 2018-12-27 株式会社Adeka 着色剤分散液、着色重合性組成物及びカラーフィルタ
JP2018116151A (ja) * 2017-01-18 2018-07-26 東京応化工業株式会社 樹脂組成物、ブラックマトリクス、表示装置、及びブラックマトリクスの製造方法
JP2018180349A (ja) * 2017-04-17 2018-11-15 信越化学工業株式会社 ポジ型レジストフィルム積層体及びパターン形成方法
JP2019128438A (ja) * 2018-01-24 2019-08-01 信越化学工業株式会社 ネガ型レジストフィルム積層体及びパターン形成方法
JPWO2022230792A1 (fr) * 2021-04-28 2022-11-03
WO2022230792A1 (fr) * 2021-04-28 2022-11-03 三菱ケミカル株式会社 Composition de résine colorée photosensible, produit durci, séparation et dispositif d'affichage d'image

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JP4994234B2 (ja) 2012-08-08
TW200702932A (en) 2007-01-16
TWI375867B (fr) 2012-11-01
JPWO2006121062A1 (ja) 2008-12-18
KR20080003764A (ko) 2008-01-08
CN101006393B (zh) 2011-11-30
CN101006393A (zh) 2007-07-25

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