WO2015129521A1 - 感放射線性組成物およびその製造方法、硬化膜、カラーフィルタおよびその製造方法、パターン形成方法、固体撮像素子ならびに画像表示装置 - Google Patents

感放射線性組成物およびその製造方法、硬化膜、カラーフィルタおよびその製造方法、パターン形成方法、固体撮像素子ならびに画像表示装置 Download PDF

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Publication number
WO2015129521A1
WO2015129521A1 PCT/JP2015/054421 JP2015054421W WO2015129521A1 WO 2015129521 A1 WO2015129521 A1 WO 2015129521A1 JP 2015054421 W JP2015054421 W JP 2015054421W WO 2015129521 A1 WO2015129521 A1 WO 2015129521A1
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Prior art keywords
group
radiation
pigment
sensitive composition
color filter
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PCT/JP2015/054421
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English (en)
French (fr)
Japanese (ja)
Inventor
和敬 高橋
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富士フイルム株式会社
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Priority to KR1020167021135A priority Critical patent/KR101864167B1/ko
Publication of WO2015129521A1 publication Critical patent/WO2015129521A1/ja

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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
    • G03F7/004—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
    • G02B5/201—Filters in the form of arrays
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/32—Monoazo dyes prepared by diazotising and coupling from coupling components containing a reactive methylene group
    • C09B29/33—Aceto- or benzoylacetylarylides
    • C09B29/335—Aceto- or benzoylacetylarylides free of acid groups
    • C09B29/338—Heterocyclic arylides, e.g. acetoacetylaminobenzimidazolone
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes
    • C09B67/0085—Non common dispersing agents
    • C09B67/009—Non common dispersing agents polymeric dispersing agent
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509—Filters, e.g. light shielding masks
    • G02F1/133514—Colour filters
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/20—Exposure; Apparatus therefor
    • G03F7/2051—Exposure without an original mask, e.g. using a programmed deflection of a point source, by scanning, by drawing with a light beam, using an addressed light or corpuscular source
    • G03F7/2053—Exposure without an original mask, e.g. using a programmed deflection of a point source, by scanning, by drawing with a light beam, using an addressed light or corpuscular source using a laser
    • G03F7/2055—Exposure without an original mask, e.g. using a programmed deflection of a point source, by scanning, by drawing with a light beam, using an addressed light or corpuscular source using a laser for the production of printing plates; Exposure of liquid photohardening compositions
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
    • H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo compounds
    • C09B45/22—Monoazo compounds containing other metals
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/10—Obtaining compounds having halogen atoms directly bound to the phthalocyanine skeleton

Definitions

  • the present invention relates to a radiation-sensitive composition.
  • the radiation sensitive composition preferably used for color layer formation of a color filter.
  • the manufacturing method of a radiation sensitive composition, a cured film, a color filter, its manufacturing method, a pattern formation method, a solid-state image sensor, and an image display apparatus is related with the manufacturing method of a radiation sensitive composition, a cured film, a color filter, its manufacturing method, a pattern formation method, a solid-state image sensor, and an image display apparatus.
  • the colorant used in the color filter is commonly required to have the following characteristics. In other words, it has optical characteristics that are favorable for color reproducibility, optical scattering such as light scattering that causes a decrease in contrast of a liquid crystal display, and unevenness in optical density that causes color unevenness and roughness of a solid-state imaging device. There is a need for a high degree of fastness, such as heat resistance, light resistance, moisture resistance, and the like, a large molar extinction coefficient, and a thin film.
  • compositions for forming a colored region of a color filter compositions described in Patent Documents 1 to 6 are known.
  • composition for forming the colored region of the color filter after the cured film is formed using the composition, the variation in the line width of the pattern due to standing for a long time until exposure is suppressed (hereinafter, “ Also referred to as “long-term detachability”), it is required to suppress the generation of foreign matter when the prepared composition is stored for a long time, and to suppress the generation of residues after exposure and development. .
  • the present invention solves such a problem, the radiation sensitive composition capable of suppressing the generation of foreign matter and the residue, while improving the long-term retention, and a method for producing the same, a cured film,
  • the present invention relates to a color filter, a manufacturing method thereof, a pattern forming method, a solid-state imaging device, and an image display device.
  • the mass ratio of CI Pigment Yellow 185 is in the range of 65.4: 35.6 to 79.0: 21.0, and the radiation sensitivity is such that the ratio of the acid value of the resin and the amine value to the acid value of the resin is in a specific range
  • the above problem has been solved by the following means ⁇ 1>, preferably by means ⁇ 2> to ⁇ 14>.
  • ⁇ 1> C.I. I. Pigment green 36, C.I. I. Pigment yellow 150, C.I. I. Containing pigments and resins including Pigment Yellow 185; C.I. with respect to 100 parts by mass of the pigment.
  • Pigment Green 36 is contained in an amount of 80 to 86 parts by mass; I. Pigment yellow 150 and C.I. I. Pigment Yellow 185 has a mass ratio in the range of 65.4: 35.6 to 79.0: 21.0,
  • the radiation sensitive composition wherein the resin has an acid value of 20 to 50 mgKOH / g and a ratio of an amine value to an acid value of 0.85 to 1.45.
  • the radiation-sensitive composition according to ⁇ 1> further comprising at least one of an acidic derivative, an amine salt of the acidic derivative, and a metal salt of the acidic derivative.
  • ⁇ 4> The radiation-sensitive composition according to any one of ⁇ 1> to ⁇ 3>, wherein a mass ratio of the resin to the pigment is 0.2 to 0.4.
  • ⁇ 5> The radiation-sensitive composition according to any one of ⁇ 1> to ⁇ 4>, further comprising a polymerizable compound and a polymerization initiator.
  • ⁇ 6> The radiation-sensitive composition according to any one of ⁇ 1> to ⁇ 5>, which is used for forming a colored layer of a color filter.
  • ⁇ 7> C.I. I. Pigment green 36, C.I. I. Pigment yellow 150, C.I. I. Containing pigments and resins including Pigment Yellow 185; C.I. with respect to 100 parts by mass of the pigment.
  • Pigment Green 36 is contained in an amount of 80 to 86 parts by mass; I. Pigment yellow 150 and C.I. I. Pigment Yellow 185 has a mass ratio in the range of 65.4: 35.6 to 79.0: 21.0, A method for producing a radiation-sensitive composition, wherein a co-dispersion liquid in which the acid value of the resin is 20 to 50 mgKOH / g and the ratio of the amine value to the acid value is 0.85 to 1.45 is used. ⁇ 8> Using the above resin, C.I. I. Pigment green 36, C.I. I. Pigment yellow 150 and C.I. I.
  • the method for producing a radiation-sensitive composition according to ⁇ 7> comprising co-dispersing a pigment containing CI Pigment Yellow 185.
  • a cured film obtained by curing the radiation-sensitive composition according to any one of ⁇ 1> to ⁇ 6>.
  • ⁇ 12> A step of applying the radiation-sensitive composition according to any one of ⁇ 1> to ⁇ 6> on a support to form a radiation-sensitive composition layer, and patterning the radiation-sensitive composition layer
  • a method for producing a color filter which includes a step of exposing the substrate to a shape and a step of developing and removing an unexposed portion to form a pattern.
  • a solid-state imaging device having a color filter according to ⁇ 10> or a color filter obtained by the method for producing a color filter according to ⁇ 12>.
  • ⁇ 14> An image display device having the color filter according to ⁇ 10> or the color filter obtained by the method for producing a color filter according to ⁇ 12>.
  • a radiation-sensitive composition capable of suppressing the generation of foreign substances and the generation of residues while improving the long-term retention.
  • a method for producing a radiation-sensitive composition, a cured film, a color filter and a method for producing the same, a pattern forming method, a solid-state imaging device, and an image display device can be provided.
  • the total solid content refers to the total mass of the components excluding the solvent from the total composition of the composition.
  • the solid content at 25 ° C.
  • the notation which does not describe substitution and non-substitution includes a group (atomic group) having a substituent together with a group (atomic group) having no substituent. To do.
  • the “alkyl group” includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
  • radiation in the present specification means, for example, an emission line spectrum of a mercury lamp, far ultraviolet rays represented by excimer laser, extreme ultraviolet rays (EUV light), X-rays, electron beams, and the like.
  • light means actinic rays or radiation.
  • exposure in this specification is not only exposure with far-ultraviolet rays such as mercury lamps and excimer lasers, X-rays, EUV light, but also drawing with particle beams such as electron beams and ion beams. Are also included in the exposure.
  • (meth) acrylate represents both and / or acrylate and methacrylate
  • (meth) acryl represents both and / or acryl and “(meth) acrylic”
  • "Acryloyl” represents both and / or acryloyl and methacryloyl.
  • “monomer” and “monomer” are synonymous.
  • a monomer is distinguished from an oligomer and a polymer, and refers to a compound having a weight average molecular weight of 2,000 or less.
  • the polymerizable compound means a compound having a polymerizable functional group, and may be a monomer or a polymer.
  • the polymerizable functional group refers to a group that participates in a polymerization reaction.
  • Me in the chemical formula represents a methyl group
  • Et represents an ethyl group
  • Pr represents a propyl group
  • Bu represents a butyl group
  • Ph represents a phenyl group.
  • the term “process” is not limited to an independent process, and is included in the term if the intended action of the process is achieved even when it cannot be clearly distinguished from other processes.
  • a weight average molecular weight and a number average molecular weight are defined as a polystyrene conversion value by GPC measurement.
  • the weight average molecular weight (Mw) and the number average molecular weight (Mn) are, for example, HLC-8220 (manufactured by Tosoh Corporation), and TSKgel Super AWM-H (manufactured by Tosoh Corporation, 6) as a column.
  • 0.0 mm ID ⁇ 15.0 cm can be determined by using a 10 mmol / L lithium bromide NMP (N-methylpyrrolidinone) solution as the eluent.
  • the radiation-sensitive composition of the present invention (hereinafter also referred to as “the composition of the present invention”) is C.I. I. Pigment green 36, C.I. I. Pigment yellow 150, C.I. I. A pigment containing CI Pigment Yellow 185 and a resin having an amine value and an acid value; I. Pigment Green 36 is contained in an amount of 80 to 86 parts by mass; I. Pigment yellow 150 and C.I. I. Pigment Yellow 185 mass ratio, that is, (C. I. Pigment Yellow 150 Mass: C. I. Pigment Yellow 185 Mass) is in the range of 65.4: 35.6 to 79.0: 21.0.
  • the resin has an acid value of 20 to 50 (mg KOH / g) and an amine value to acid value ratio of 0.85 to 1.45 (mg KOH / g). According to the present invention, it is possible to suppress the generation of foreign substances and the generation of residues while improving the long-term retention. Moreover, according to this invention, the filterability of a composition can also be made favorable and the roughness of the surface when it is set as a cured film can also be suppressed.
  • the composition of the present invention is preferably used for forming a colored layer of a color filter.
  • the composition of the present invention comprises C.I. I. Pigment green 36, C.I. I. Pigment yellow 150, C.I. I.
  • the pigment containing Pigment Yellow 185 and the resin having an amine value and an acid value it may further contain a polymerizable compound, a polymerization initiator, and the like.
  • the composition of the present invention contains C.I. I. Pigment green 36, C.I. I. Pigment yellow 150, C.I. I.
  • the pigment containing Pigment Yellow 185 and the resin having an amine value and an acid value a polymerizable compound, a polymerization initiator, and an alkali-soluble resin are preferably contained. Further, it may contain a surfactant, a solvent and the like.
  • the composition of the present invention contains C.I. I. Pigment green 36, C.I. I. Pigment yellow 150, C.I. I.
  • a polymerizable compound is preferably contained.
  • components such as a surfactant and a solvent may be included.
  • the composition of the present invention contains C.I. I. Pigment green 36, C.I. I. Pigment yellow 150 and C.I. I. Pigment Yellow 185 is contained at least.
  • the content of Pigment Green 36 is 80 to 86 parts by mass, preferably 81 to 85 parts by mass, and more preferably 82 to 84 parts by mass. C.I. to 100 parts by mass of pigment. I.
  • C.I. I. The content of Pigment Yellow 185 is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, and even more preferably 2 to 10 parts by mass.
  • C.I. I. The content of Pigment Yellow 150 is preferably 1 to 40 parts by mass, more preferably 5 to 20 parts by mass, and still more preferably 8 to 15 parts by mass.
  • C.I. I. Pigment yellow 150 and C.I. I. Pigment Yellow 185 has a mass ratio of 65.4: 35.6 to 79.0: 21.0, preferably 65.4: 35.6 to 75.0: 25.0, and 68.0. : The range of 32.0 to 72.0: 28.0 is more preferable.
  • the average primary particle size of the pigment used in the composition of the present invention is practically 10 nm or more.
  • the upper limit is preferably 1 ⁇ m or less, more preferably 500 nm or less, further preferably 200 nm or less, further preferably 100 nm or less, and particularly preferably 50 nm or less from the viewpoint of obtaining better contrast.
  • the ratio (Mv / Mn) of the volume average particle diameter (Mv) and the number average particle diameter (Mn) is used as an index representing the monodispersity of the particles unless otherwise specified.
  • the monodispersity of the pigment fine particles (primary particles), that is, Mv / Mn is preferably 1.0 to 2.0, more preferably 1.0 to 1.8, and 1.0 to 1. 5 is particularly preferred.
  • the average primary particle diameter of the particles is obtained by obtaining the equivalent circle diameter from an image observed with a transmission electron microscope, and taking the average value of the 500 particles.
  • the pigment particles may be prepared by a normal method, for example, by pulverizing by milling (breakdown method) or by precipitation using a good solvent and a poor solvent (build-up method). Also good.
  • breakdown method a pigment particle can be refined
  • the latter build-up method is also referred to as a reprecipitation method and the like.
  • JP 2011-026452 A, JP 2011-012214 A, JP 2011-001501 A, JP 2010-235895 A Reference can be made to JP 2010-2091 A, JP 2010-209160 A, and the like.
  • the composition of the present invention contains an inorganic pigment, C.I. for adjusting the spectral transmittance of the composition.
  • C.I. for adjusting the spectral transmittance of the composition.
  • I. Pigment green 36, C.I. I. Pigment yellow 150 and C.I. I. Colorants such as organic pigments and dyes other than CI Pigment Yellow 185 may be added as appropriate.
  • Examples of the inorganic pigment that can be appropriately added to the composition of the present invention include metal compounds represented by metal oxides, metal complex salts, and the like. Specifically, iron, cobalt, aluminum, silicon, cadmium, lead, copper And metal oxides such as titanium, zirconium, magnesium, chromium, zinc and antimony, and complex pigments of the above metals, black pigments such as carbon black and titanium black.
  • Known dyes that can be appropriately added to the composition of the present invention include, for example, JP-A 64-90403, JP-A 64-91102, JP-A-1-94301, JP-A-6-11614, Japanese Patent No. 2592207, US Pat. No. 4,808,501, US Pat. No. 5,667,920, US Pat. No. 505950, US Pat. No. 5,667,920, JP-A-5-333207, JP-A-6-35183, The dyes disclosed in Kaihei 6-51115 and JP-A-6-194828 can be used.
  • pyrazole azo compounds When classified as a chemical structure, pyrazole azo compounds, pyromethene compounds, anilinoazo compounds, triphenylmethane compounds, anthraquinone compounds, benzylidene compounds, oxonol compounds, pyrazolotriazole azo compounds, pyridone azo compounds, cyanine compounds, phenothiazine compounds, pyrrolopyrazole azomethine compounds, etc. Can be used.
  • a dye multimer may be used as the dye. Examples of the dye multimer include compounds described in JP2011-213925A and JP2013-041097A.
  • the blending amount of the pigment contained in the composition of the present invention can be 10% by mass or more in the total solid content of the radiation-sensitive composition, can be 20% by mass or more, and can be 30% by mass or more. You can also Although there is no restriction
  • the total amount of Pigment Yellow 185 is preferably 95% by mass or more of the total amount of the colorant.
  • the total amount of the colorant means the total amount of the colorant including the dye when the dye is included in addition to the pigment.
  • C.I. I. Pigment green 36 In the total amount of the colorant contained in the composition of the present invention, C.I. I. Pigment green 36, C.I. I. Pigment yellow 150 and C.I. I.
  • the content of the colorant other than CI Pigment Yellow 185 can be 10% by mass or less, 5% by mass or less, 1% by mass or less, and 0% by mass. You can also.
  • the specific dispersion resin used in the present invention (hereinafter also referred to as “specific dispersion resin”) has an amine value and an acid value, an acid value of 20 to 50, and a ratio of the amine value to the acid value of 0. .85 to 1.45.
  • the ratio of the amine value to the acid value (amine value / acid value) of the specific dispersion resin is 0.85 to 1.45, preferably 0.85 to 1.45, more preferably 0.90 to 1.42.
  • 1.00 to 1.40 is more preferable. By setting it as such a range, the effect of this invention can be show
  • the acid value of the specific dispersion resin is 20 to 50 mgKOH / g, preferably 25 to 45 mgKOH / g, and more preferably 30 to 40 mgKOH / g.
  • the amine value of the specific dispersion resin is preferably 17 to 72.5 mgKOH / g, more preferably 20 to 70 mgKOH / g, and further preferably 30 to 60 mgKOH / g.
  • the mass ratio of the specific dispersion resin to the pigment is preferably 0.2 to 0.4, and more preferably 0.25 to 0.35.
  • the amine value and acid value of the specific dispersion resin used in the present invention are values measured by the following methods.
  • the amine value of the specific dispersion resin is represented by the weight of potassium hydroxide (KOH) equivalent to the basic component per 1 g of the solid content.
  • KOH potassium hydroxide
  • the measurement sample was dissolved in acetic acid, and the obtained solution was neutralized and titrated with a 0.1 M perchloric acid / acetic acid solution using a potentiometric titrator (trade name: AT-510, manufactured by Kyoto Electronics Industry).
  • the amine value was calculated by the following formula using the inflection point of the titration pH curve as the titration end point.
  • Vs Amount of 0.1 M perchloric acid / acetic acid solution required for titration (mL)
  • f titer of 0.1M perchloric acid / acetic acid solution
  • w weight (g) of measurement sample (in solid content)
  • the acid value of the specific dispersion resin represents the weight of potassium hydroxide required to neutralize the acidic component per gram of solid content.
  • the acid value was calculated by the following formula using the inflection point of the titration pH curve as the titration end point.
  • A 56.11 ⁇ Vs ⁇ 0.5 ⁇ f / w
  • Vs Amount of 0.1 M sodium hydroxide aqueous solution required for titration (mL)
  • f Potency of 0.1 M aqueous sodium hydroxide solution
  • w Weight of measurement sample (g) (converted to solid content)
  • the specific dispersion resin used in the present invention preferably has a main chain portion composed of an oligomer or polymer containing a known amino group, more preferably a primary or secondary amino group. More specifically, oligomers or polymers containing amino groups include poly (lower alkylene imine), polyallylamine, polydiallylamine, metaxylenediamine-epichlorohydrin polycondensate, polyvinylamine, 3-dialkylaminopropyl (meth).
  • the main chain structure is preferably selected from an acrylic amide copolymer, a (meth) acrylic acid 2-dialkylaminoethyl copolymer, and the like.
  • the poly (lower alkyleneimine) may be chain-like or network-like, but is preferably network-like.
  • the number average molecular weight of the main chain portion in the specific dispersion resin is preferably 100 to 10,000, more preferably 200 to 5,000, further preferably 300 to 2,000, and further preferably in the range of 500 to 1500.
  • the main chain portion of the specific dispersion resin is particularly preferably composed of poly (lower alkyleneimine) or a polyallylamine skeleton.
  • poly (lower alkyleneimine) “lower” means 1 to 5 carbon atoms
  • “lower alkyleneimine” means an alkyleneimine having 1 to 5 carbon atoms.
  • the specific dispersion resin has a structure having a repeating unit represented by the general formula (I-1) and a repeating unit represented by the general formula (I-2), or a repeating unit represented by the general formula (II-1). It preferably includes a structure containing a unit and a repeating unit represented by formula (II-2). (Repeating unit represented by general formula (I-1) and repeating unit represented by general formula (I-2))
  • the repeating unit represented by formula (I-1) and the repeating unit represented by formula (I-2) will be described in detail.
  • R 1 and R 2 each independently represents a hydrogen atom, a halogen atom or an alkyl group.
  • a independently represents an integer of 1 to 5; * Represents a connecting part between repeating units.
  • X represents a group having a functional group of pKa14 or less.
  • Y represents an oligomer chain or a polymer chain having 40 to 10,000 atoms.
  • the specific dispersion resin has a repeating unit represented by the general formula (I-3) as a copolymer component in addition to the repeating units represented by the general formula (I-1) and the general formula (I-2). It is preferable.
  • R 1 , R 2 and a have the same meanings as R 1, R 2, and a in the general formula (I-1).
  • Y ′ represents an oligomer chain or polymer chain having an anion group and having 40 to 10,000 atoms.
  • the repeating unit represented by formula (I-3) is reacted by adding an oligomer or polymer having a group that reacts with an amine to form a salt to a resin having a primary or secondary amino group in the main chain. Can be formed.
  • R 1 and R 2 are particularly preferably hydrogen atoms.
  • a is preferably 2 from the viewpoint of obtaining raw materials.
  • the specific dispersion resin includes a lower alkylene having a primary or tertiary amino group in addition to the repeating units represented by the general formula (I-1), the general formula (I-2), and the general formula (I-3). It may contain imine as a repeating unit. In addition, the group shown by said X, Y, or Y 'may couple
  • the repeating unit represented by the general formula (I-1) is a repeating unit having a basic nitrogen atom to which a partial structure X having a functional group of pKa14 or less is bonded, and such a repeating unit having a basic nitrogen atom. From the viewpoint of storage stability and developability, it is preferably contained in an amount of 1 to 80 mol%, particularly preferably 3 to 50 mol%, in all repeating units contained in the specific dispersion resin.
  • the repeating unit represented by the general formula (I-2) is a repeating unit having an oligomer chain or a polymer chain having 40 to 10,000 atoms, and such a repeating unit is specified from the viewpoint of storage stability.
  • the content is preferably 10 to 90 mol%, particularly preferably 30 to 70 mol%, in all repeating units contained in the dispersion resin. From the viewpoint of the balance between dispersion stability and hydrophilicity / hydrophobicity, the content ratio [(I-1) :( I-2)] of the repeating unit (I-1) and the repeating unit (I-2) is 10 in molar ratio. The range is preferably 1: 1 to 1: 100, and more preferably 1: 1 to 1:10.
  • the repeating unit represented by the general formula (I-3) used in combination optionally has a partial structure containing an oligomer chain or polymer chain Y ′ having 40 to 10,000 atoms in the main chain nitrogen atom. And is preferably contained in an amount of 0.5 to 20 mol%, particularly preferably 1 to 10 mol% in all repeating units contained in the specific dispersion resin. In addition, it can confirm that the polymer chain Y 'has ionically bonded by infrared spectroscopy or base titration.
  • R 3 , R 4 , R 5 and R 6 each independently represents a hydrogen atom, a halogen atom or an alkyl group.
  • *, X and Y have the same meanings as *, X and Y in formulas (I-1) and (I-2).
  • the specific dispersion resin includes a repeating unit represented by the following general formula (II-3) in addition to the repeating unit represented by the general formula (II-1) and the repeating unit represented by the general formula (II-2).
  • a unit may be included as a copolymerization component.
  • R 3, R 4, R 5 and R 6 have the same meanings as R 3, R 4, R 5 and R 6 in Formula (II-1).
  • Y ′ has the same meaning as Y ′ in formula (I-3).
  • R 3 , R 4 , R 5 and R 6 are preferably hydrogen atoms from the viewpoint of availability of raw materials.
  • the general formula (II-1) is a repeating unit having a basic nitrogen atom to which a partial structure X having a functional group of pKa14 or less is bonded, and such a repeating unit having a basic nitrogen atom has storage stability, From the viewpoint of developability, the content is preferably 1 to 80 mol%, particularly preferably 3 to 50 mol%, in all repeating units contained in the specific dispersion resin.
  • the general formula (II-2) is a repeating unit having an oligomer chain or polymer chain Y having 40 to 10,000 atoms, and such a repeating unit is included in the specific dispersion resin from the viewpoint of storage stability.
  • the content is preferably 10 to 90 mol%, particularly preferably 30 to 70 mol%, in all repeating units.
  • the content ratio [(II-1) :( II-2)] of the repeating unit (II-1) and the repeating unit (II-2) is 10 in molar ratio.
  • the range is preferably 1: 1 to 1: 100, and more preferably 1: 1 to 1:10.
  • the repeating unit represented by the general formula (II-3) used in combination is preferably contained in an amount of 0.5 to 20 mol%, preferably 1 to 10 mol%, in all repeating units of the specific dispersion resin. It is particularly preferable.
  • the specific dispersion resin is particularly preferably an embodiment including both the repeating unit represented by the general formula (I-1) and the repeating unit represented by the general formula (I-2). preferable.
  • ⁇ Partial structure X having a functional group of pKa14 or less The partial structure X having a functional group of pKa14 or less will be described. X has a functional group having a pKa of 14 or less at a water temperature of 25 ° C.
  • pKa has the definition described in Chemical Handbook (II) (4th revised edition, 1993, edited by The Chemical Society of Japan, Maruzen Co., Ltd.).
  • the “functional group of pKa14 or less” is not particularly limited as long as the physical properties satisfy this condition, and examples thereof include those having a pKa satisfying the above range with known functional groups.
  • the following functional groups are preferred, and those having a pKa of 11 or less are particularly preferred.
  • partial structure X examples include, for example, a carboxylic acid group (pKa: about 3 to 5), a sulfonic acid (pKa: about ⁇ 3 to ⁇ 2), —COCH 2 CO— (pKa: about 8 to 10), —COCH 2 CN (pKa: about 8 to 11), —CONHCO—, phenolic hydroxyl group, —R F CH 2 OH or — (R F ) 2 CHOH (R F represents a perfluoroalkyl group.
  • a carboxylic acid group pKa: about 3 to 5
  • a sulfonic acid pKa: about ⁇ 3 to ⁇ 2
  • —COCH 2 CO— pKa: about 8 to 10
  • —COCH 2 CN pKa: about 8 to 11
  • CONHCO— phenolic hydroxyl group
  • R F CH 2 OH or — (R F ) 2 CHOH R F represents a perfluoroalkyl group
  • PKa 9 to 11 Degree
  • sulfonamide groups pKa: about 9 to 11
  • carboxylic acid groups pKa: about 3 to 5
  • sulfonic acid groups pKa: about ⁇ 3 to ⁇ 2
  • —COCH 2 CO -(PKa: about 8 to 10) is preferable.
  • the partial structure X having a functional group of pKa14 or less is preferably directly bonded to the basic nitrogen atom in the repeating unit having the basic nitrogen atom.
  • the nitrogen atom of the repeating unit having a basic nitrogen atom and the partial structure X may be linked in a form that forms a salt by ionic bonding as well as a covalent bond.
  • U represents a single bond or a divalent linking group.
  • d and e each independently represents 0 or 1;
  • Q represents an acyl group or an alkoxycarbonyl group.
  • Examples of the divalent linking group represented by U include alkylene (more specifically, for example, —CH 2 —, —CH 2 CH 2 —, —CH 2 CHMe—, — (CH 2 ) 5 — , —CH 2 CH (n—C 10 H 21 ) —, etc.), oxygen-containing alkylene (more specifically, for example, —CH 2 OCH 2 —, —CH 2 CH 2 OCH 2 CH 2 —, etc.) , Arylene groups (eg, phenylene, tolylene, biphenylene, naphthylene, furylene, pyrrolylene, etc.), alkyleneoxy (eg, ethyleneoxy, propyleneoxy, phenyleneoxy, etc.), etc.
  • alkylene more specifically, for example, —CH 2 —, —CH 2 CH 2 —, —CH 2 CHMe—, — (CH 2 ) 5 — , —CH 2 CH (n—C 10 H 21 ) —,
  • an arylene group having 6 to 20 carbon atoms is preferable, and an alkylene having 1 to 20 carbon atoms or an arylene group having 6 to 15 carbon atoms is particularly preferable.
  • d is preferably 1, and e is preferably 0.
  • Q represents an acyl group or an alkoxycarbonyl group.
  • acyl group in Q an acyl group having 1 to 30 carbon atoms (eg, formyl, acetyl, n-propanoyl, benzoyl, etc.) is preferable, and acetyl is particularly preferable.
  • alkoxycarbonyl group in Q Q is particularly preferably an acyl group, and an acetyl group is preferable from the viewpoint of easy production and availability of a raw material (precursor X ′ of X).
  • the partial structure X is preferably bonded to a basic nitrogen atom in a repeating unit having a basic nitrogen atom. Thereby, the dispersibility and dispersion stability of the titanium dioxide particles can be further improved. Furthermore, since partial structure X includes a functional group of pKa14 or less, it also functions as an alkali-soluble group. As a result, energy is imparted to the coating film formed from the composition of the present invention to partially cure it, and when unexposed areas are dissolved and removed to form a pattern, development of the uncured area into an alkaline developer is performed. Improve the dispersibility, dispersion stability, and developability.
  • the content of the functional group having a pKa of 14 or less in the partial structure X is not particularly limited, but is preferably 0.01 to 5 mmol, particularly preferably 0.05 to 1 mmol, with respect to 1 g of the specific dispersion resin. Within this range, the dispersibility and dispersion stability of the titanium dioxide particles are improved, and when a cured film is formed from the composition of the present invention, the developability of the uncured portion is excellent. From the viewpoint of the acid value, it is preferable that the acid value of the specific dispersion resin is contained in an amount of about 5 to 50 mgKOH / g.
  • the oligomer chain or polymer chain Y having 40 to 10,000 atoms will be described.
  • Examples of Y include known polymer chains such as polyester, polyamide, polyimide, and poly (meth) acrylic acid ester that can be connected to the main chain portion of the specific dispersion resin.
  • the binding site with the specific dispersion resin in Y is preferably the terminal of the oligomer chain or polymer chain Y.
  • Y is at least one selected from a poly (lower alkyleneimine) -based repeating unit, a polyallylamine-based repeating unit, a polydiallylamine-based repeating unit, a metaxylenediamine-epichlorohydrin polycondensate-based repeating unit, and a polyvinylamine-based repeating unit. It is preferably bonded to the above nitrogen atom of the repeating unit having a nitrogen atom.
  • the bonding mode between the main chain portion such as a repeating unit having a nitrogen atom and Y is a covalent bond, an ionic bond, or a mixture of a covalent bond and an ionic bond.
  • Y is preferably ionically bonded as an amide bond or carboxylate with the nitrogen atom of the repeating unit having the basic nitrogen atom.
  • the number of atoms of the oligomer chain or polymer chain Y is preferably 50 to 5,000, more preferably 60 to 3,000, from the viewpoints of dispersibility, dispersion stability, and developability.
  • the number average molecular weight of Y is particularly preferably 1,000 to 50,000, and particularly preferably 1,000 to 30,000 from the viewpoints of dispersibility, dispersion stability, and developability. It is preferable that two or more side chain structures represented by Y are connected to the main chain in one molecule of the resin, and more preferably five or more are connected.
  • Y preferably has a structure represented by the general formula (III-1).
  • Z is a polymer or oligomer having a polyester chain as a partial structure, and represents a group obtained by removing a carboxyl group from a polyester having a free carboxylic acid represented by the following general formula (IV) .
  • Z has the same meaning as Z in general formula (III-1).
  • Y ′ is also preferably the general formula (III-2).
  • Z has the same meaning as Z in general formula (III-1).
  • a polyester having a carboxyl group at one end includes (IV-1) polycondensation of carboxylic acid and lactone, (IV-2) polycondensation of hydroxy group-containing carboxylic acid, IV-3) It can be obtained by polycondensation of a dihydric alcohol and a dicarboxylic acid (or a cyclic acid anhydride).
  • the carboxylic acid used in the polycondensation reaction of carboxylic acid and lactone is preferably an aliphatic carboxylic acid (a linear or branched carboxylic acid having 1 to 30 carbon atoms, such as formic acid, acetic acid, propionic acid, butyric acid, Valeric acid, n-hexanoic acid, n-octanoic acid, n-decanoic acid, n-dodecanoic acid, palmitic acid, 2-ethylhexanoic acid, cyclohexane acid, etc.), hydroxy group-containing carboxylic acid (directly having 1 to 30 carbon atoms) A chain or branched hydroxy group-containing carboxylic acid is preferable.
  • aliphatic carboxylic acid a linear or branched carboxylic acid having 1 to 30 carbon atoms, such as formic acid, acetic acid, propionic acid, butyric acid, Valeric acid, n-hexanoic acid,
  • glycolic acid for example, glycolic acid, lactic acid, 3-hydroxypropionic acid, 4-hydroxydodecanoic acid, 5-hydroxydodecanoic acid, ricinoleic acid, 12-hydroxydodecanoic acid, 12-hydroxystearic acid Acid, 2,2-bis (hydroxymethyl) butyric acid, etc.).
  • Hydroxy group-containing carboxylic acid aliphatic carboxylic acid or 1 to 20 carbon atoms are preferred. These carboxylic acids may be used as a mixture.
  • lactone a known lactone can be used, for example, ⁇ -propiolactone, ⁇ -butyrolactone, ⁇ -butyrolactone, ⁇ -hexanolactone, ⁇ -octanolactone, ⁇ -valerolactone, ⁇ -hexalanolactone. , ⁇ -octanolactone, ⁇ -caprolactone, ⁇ -dodecanolactone, ⁇ -methyl- ⁇ -butyrolactone, etc., and ⁇ -caprolactone is particularly preferred from the viewpoint of reactivity and availability.
  • lactones may be used as a mixture of plural kinds.
  • the hydroxy group-containing carboxylic acid in the polycondensation of the hydroxy group-containing carboxylic acid is the same as the hydroxy group-containing carboxylic acid in (IV-1), and the preferred range is also the same.
  • a linear or branched aliphatic diol (a diol having 2 to 30 carbon atoms is preferred)
  • aliphatic diols having 2 to 20 carbon atoms are preferred.
  • the divalent carboxylic acid a linear or branched divalent aliphatic carboxylic acid (a divalent aliphatic carboxylic acid having 1 to 30 carbon atoms is preferable.
  • succinic acid, maleic acid, adipic acid, sebacic acid, Dodecanedioic acid, glutaric acid, suberic acid, tartaric acid, oxalic acid, malonic acid, etc. Particularly, divalent carboxylic acids having 3 to 20 carbon atoms are preferred.
  • acid anhydrides equivalent to these divalent carboxylic acids for example, succinic anhydride, glutaric anhydride, etc.
  • the divalent carboxylic acid and the dihydric alcohol are preferably charged at a molar ratio of 1: 1. This makes it possible to introduce a carboxylic acid at the terminal.
  • the polycondensation during the production of the polyester is preferably performed by adding a catalyst.
  • a catalyst that functions as a Lewis acid is preferable.
  • a Ti compound for example, Ti (OBu) 4 , Ti (O—Pr) 4, etc.
  • a Sn compound for example, tin octylate, dibutyltin oxide, dibutyltin laurate
  • Monobutyltin hydroxybutyl oxide stannic chloride, etc.
  • protonic acids for example, sulfuric acid, paratoluenesulfonic acid, etc.
  • the amount of the catalyst is preferably from 0.01 mol% to 10 mol%, particularly preferably from 0.1 mol% to 5 mol%, based on the number of moles of all monomers.
  • the reaction temperature is preferably from 80 ° C to 250 ° C, particularly preferably from 100 ° C to 180 ° C.
  • the reaction time varies depending on the reaction conditions, but is generally 1 to 24 hours.
  • the number average molecular weight of the polyester can be measured as a polystyrene converted value by the GPC method.
  • the number average molecular weight of the polyester is 1,000 to 1,000,000, preferably 2,000 to 100,000, and particularly preferably 3,000 to 50,000. When the molecular weight is in this range, both dispersibility and developability can be achieved.
  • the polyester partial structure forming the polymer chain in Y is particularly a polyester obtained by (IV-1) polycondensation of a carboxylic acid and a lactone, and (IV-2) polycondensation of a hydroxy group-containing carboxylic acid. Is preferable from the viewpoint of ease of manufacture.
  • p and q represent the number of linked polyester chains, and each independently represents 5 to 100,000.
  • R ′ represents a hydrogen atom or an alkoxycarbonyl group.
  • the specific dispersion resin preferably has a weight average molecular weight of 3,000 to 100,000, more preferably 5,000 to 55,000, and still more preferably 7,000 to 20,000.
  • the presence of the nitrogen atom in the repeating unit (i) having a nitrogen atom in the specific dispersion resin can be confirmed by a method such as acid titration, the presence of a functional group having a pKa of 14 or less, and the functional group Can be confirmed by a method such as base titration, nuclear magnetic resonance spectroscopy, and infrared spectroscopy.
  • the point of having an oligomer chain or polymer chain Y having 40 to 10,000 atoms in the side chain can be confirmed by a method such as nuclear magnetic resonance spectroscopy or GPC method.
  • the weight average molecular weight of the specific dispersion resin is 10,000.
  • the amine value of the specific dispersion resin is 45 (mgKOH / g), and the acid value is 32.3 (mgKOH / g).
  • 1 type of specific dispersion resin may be contained in the composition of this invention, and may be contained 2 or more types.
  • the composition of the present invention may further contain a pigment derivative.
  • the pigment derivative is a compound having a structure in which a part of an organic pigment is substituted with an acidic group, a basic group or a phthalimidomethyl group.
  • the pigment derivative preferably contains a pigment derivative having an acidic group (acidic derivative) or a pigment derivative having a basic group (basic derivative) from the viewpoint of dispersibility and dispersion stability of the pigment. It is more preferable to contain the acidic derivative.
  • amine salts or metal salts of acidic derivatives for example, salts of iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony, etc.).
  • organic pigment for constituting the pigment derivative examples include diketopyrrolopyrrole pigments, azo pigments, phthalocyanine pigments, anthraquinone pigments, quinacridone pigments, dioxazine pigments, perinone pigments, perylene pigments, thioindigo pigments , Isoindoline pigments, isoindolinone pigments, quinophthalone pigments, metal complex pigments, and the like.
  • the acidic group possessed by the pigment derivative is preferably a sulfonic acid, a carboxylic acid or a salt thereof (the salt is preferably a quaternary ammonium salt such as tetramethylammonium salt or tetrabutylammonium salt).
  • An acid group is more preferable, and a sulfonic acid group is particularly preferable.
  • the basic group possessed by the pigment derivative is preferably an amino group, particularly preferably a tertiary amino group.
  • quinoline-based, benzimidazolone-based and isoindoline-based pigment derivatives are particularly preferable, and quinoline-based and benzimidazolone-based pigment derivatives are more preferable.
  • a pigment derivative having the following structure is preferable.
  • A represents a partial structure selected from the following general formulas (PA-1) to (PA-3).
  • B represents a single bond or a (t + 1) -valent linking group.
  • C represents a single bond, —NH—, —CONH—, —CO 2 —, —SO 2 NH—, —O—, —S— or SO 2 —.
  • D represents a single bond, an alkylene group, a cycloalkylene group or an arylene group.
  • E represents —SO 3 H, —SO 3 M (M represents an alkali metal atom), —CO 2 H or N (Rpa) (Rpb).
  • Rpa and Rpb each independently represents an alkyl group or an aryl group, and Rpa and Rpb may be linked to each other to form a ring.
  • t represents an integer of 1 to 5.
  • Rp1 represents an alkyl group having 1 to 5 carbon atoms or an aryl group.
  • Rp2 represents a hydrogen atom, a halogen atom, an alkyl group, or a hydroxyl group.
  • s represents an integer of 1 to 4. When s is 2 or more, the plurality of Rp2s may be the same as or different from each other.
  • Rp3 represents a single bond, —NH—, —CONH—, —CO 2 —, —SO 2 NH—, —O—, —S— or Represents SO 2 —. * Represents a connecting portion with B.
  • Rp1 is particularly preferably a methyl group or a phenyl group, and most preferably a methyl group.
  • Rp2 is preferably a hydrogen atom or a halogen atom, and most preferably a hydrogen atom or a chlorine atom.
  • examples of the (t + 1) -valent linking group represented by B include an alkylene group, a cycloalkylene group, an arylene group, and a heteroarylene group.
  • linking groups represented by the following structural formulas (PA-4) to (PA-9) are particularly preferable.
  • pigment derivatives having a linking group represented by the structural formula (PA-5) or (PA-8), particularly as B are more excellent in dispersibility. This is preferable.
  • examples of the alkylene group, cycloalkylene group and arylene group represented by D include methylene, ethylene, propylene, butylene, pentylene, hexylene, decylene, cyclopropylene, cyclobutylene, cyclopentylene, Examples include cyclohexylene, cyclooctylene, cyclodecylene, phenylene, naphthylene, and the like.
  • an alkylene group is particularly preferable, and alkylene having 1 to 5 carbon atoms is more preferable.
  • examples of the alkyl group and aryl group in Rpa and Rpb include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group.
  • the present invention is not limited thereto.
  • the descriptions in paragraphs 0162 to 0183 of JP2011-252065A and paragraphs 0019 to 0035 of JP2004217784A can be referred to, and the contents thereof are incorporated in the present specification.
  • the content of the pigment derivative is preferably 1 to 30% by mass and more preferably 3 to 20% by mass with respect to the total mass of the pigment in the composition. Only one pigment derivative may be used, or two or more pigment derivatives may be used in combination.
  • the composition of the present invention may further contain a polymerizable compound.
  • a polymerizable compound a known polymerizable compound that can be crosslinked by a radical, acid, or heat can be used.
  • a polymerizable compound containing an ethylenically unsaturated bond, a cyclic ether (epoxy, oxetane), methylol, or the like can be used.
  • the polymerizable compound is suitably selected from compounds having at least one terminal ethylenically unsaturated bond, preferably two or more, from the viewpoint of sensitivity.
  • a polyfunctional polymerizable compound having 4 or more functional groups is preferable, and a polyfunctional polymerizable compound having 5 or more functional groups is more preferable.
  • Such compound groups are widely known in the industrial field, and these can be used without particular limitation in the present invention. These may be in any chemical form such as, for example, monomers, prepolymers, ie dimers, trimers and oligomers or mixtures thereof and multimers thereof.
  • the polymeric compound in this invention may be used individually by 1 type, and may use 2 or more types together.
  • examples of monomers and prepolymers thereof include unsaturated carboxylic acids (for example, acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, maleic acid, etc.), esters thereof, amides, And multimers thereof, preferably esters of unsaturated carboxylic acids and aliphatic polyhydric alcohol compounds, amides of unsaturated carboxylic acids and aliphatic polyhydric amine compounds, and multimers thereof. is there.
  • unsaturated carboxylic acids for example, acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, maleic acid, etc.
  • esters thereof for example, acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, maleic acid, etc.
  • esters thereof for example, acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, maleic acid, etc.
  • a dehydration condensation reaction product with a functional carboxylic acid is also preferably used.
  • an addition reaction product of an unsaturated carboxylic acid ester or amide having an electrophilic substituent such as an isocyanate group or an epoxy group with a monofunctional or polyfunctional alcohol, amine, or thiol, and a halogen group A substitution reaction product of an unsaturated carboxylic acid ester or amide having a detachable substituent such as a tosyloxy group and a monofunctional or polyfunctional alcohol, amine or thiol is also suitable.
  • compounds described in paragraphs [0095] to [0108] of JP-A-2009-288705 can be preferably used in the present invention.
  • a compound having an ethylenically unsaturated group having a boiling point of 100 ° C. or higher under normal pressure and having at least one addition-polymerizable ethylene group is also preferable.
  • examples include monofunctional acrylates and methacrylates such as polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, and phenoxyethyl (meth) acrylate; polyethylene glycol di (meth) acrylate, trimethylolethanetri ( (Meth) acrylate, neopentyl glycol di (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, hexanedio
  • polyfunctional acrylates and methacrylates such as epoxy acrylates which are reaction products of epoxy resin and (meth) acrylic acid, and mixtures thereof.
  • a polyfunctional (meth) acrylate obtained by reacting a polyfunctional carboxylic acid with a compound having a cyclic ether group such as glycidyl (meth) acrylate and an ethylenically unsaturated group can also be used.
  • fluorene rings described in JP 2010-160418 A, JP 2010-129825 A, JP 4364216 A, etc., and ethylenically unsaturated groups.
  • a compound having two or more functions, a cardo resin can also be used.
  • radically polymerizable monomers represented by the following general formulas (MO-1) to (MO-5) can also be suitably used.
  • T is an oxyalkylene group
  • the terminal on the carbon atom side is bonded to R.
  • n is 0 to 14, and m is 1 to 8.
  • a plurality of R and T present in one molecule may be the same or different.
  • at least one of a plurality of R is —OC ( ⁇ O) CH ⁇ CH 2 or —OC A group represented by ( ⁇ O) C (CH 3 ) ⁇ CH 2 is represented.
  • Specific examples of the polymerizable compounds represented by the above general formulas (MO-1) to (MO-5) include the compounds described in paragraph numbers 0248 to 0251 of JP-A-2007-2699779. It can be suitably used in the invention.
  • dipentaerythritol triacrylate (KAYARAD D-330 as a commercial product; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetraacrylate (KAYARAD D-320 as a commercial product); Nippon Kayaku Co., Ltd.
  • dipentaerythritol penta (meth) acrylate (as a commercial product, KAYARAD D-310; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol hexa (meth) acrylate (as a commercial product, KAYARAD DPHA; Nippon Kayaku Co., Ltd.) ), Ethyleneoxy-modified dipentaerythritol hexaacrylate (commercially available product is A-DPH-12E; manufactured by Shin-Nakamura Chemical Co., Ltd.) and these (meth) acryloyl groups are substituted with ethylene glycol and propylene glycol residues. It preferred to have structure. These oligomer types can also be used. Further, M-305 manufactured by Toagosei Co., Ltd. can also be used as a commercial product.
  • the polymerizable compound is a polyfunctional monomer and may have an acid group such as a carboxyl group, a sulfonic acid group, or a phosphoric acid group. If the ethylenic compound has an unreacted carboxyl group as in the case of a mixture as described above, this can be used as it is. Non-aromatic carboxylic acid anhydrides may be reacted to introduce acid groups.
  • non-aromatic carboxylic acid anhydride examples include tetrahydrophthalic anhydride, alkylated tetrahydrophthalic anhydride, hexahydrophthalic anhydride, alkylated hexahydrophthalic anhydride, succinic anhydride, anhydrous Maleic acid is mentioned.
  • the monomer having an acid group is an ester of an aliphatic polyhydroxy compound and an unsaturated carboxylic acid, and an unreacted hydroxyl group of the aliphatic polyhydroxy compound is reacted with a non-aromatic carboxylic acid anhydride to form an acid group.
  • the polyfunctional monomer provided is preferred, and particularly preferably in this ester, the aliphatic polyhydroxy compound is pentaerythritol and / or dipentaerythritol. Examples of commercially available products include M-510 and M-520 as polybasic acid-modified acrylic oligomers manufactured by Toagosei Co., Ltd.
  • a preferable acid value of the polyfunctional monomer having an acid group is 0.1 mgKOH / g to 40 mgKOH / g, and particularly preferably 5 mgKOH / g to 30 mgKOH / g.
  • the acid value of the polyfunctional monomer is too low, the developing dissolution properties are lowered, and if it is too high, the production and handling are difficult, the photopolymerization performance is lowered, and the curability such as the surface smoothness of the pixel is deteriorated. Therefore, when two or more polyfunctional monomers having different acid groups are used in combination, or when a polyfunctional monomer having no acid group is used in combination, the acid groups as the entire polyfunctional monomer should be adjusted to fall within the above range. Is preferred.
  • polyfunctional monomer which has a caprolactone structure is not particularly limited as long as it has a caprolactone structure in the molecule.
  • R 1 represents a hydrogen atom or a methyl group
  • m represents a number of 1 or 2
  • “*” represents a bond
  • R 1 represents a hydrogen atom or a methyl group, and “*” represents a bond.
  • the polyfunctional monomer which has a caprolactone structure can be used individually or in mixture of 2 or more types.
  • the specific monomer in the present invention is preferably at least one selected from the group of compounds represented by the following general formula (Z-4) or (Z-5).
  • each E is independently — ((CH 2 ) yCH 2 O) — or — ((CH 2 ) yCH (CH 3 ) O) —.
  • Each represents independently an integer of 0 to 10
  • each X independently represents an acryloyl group, a methacryloyl group, a hydrogen atom, or a carboxyl group.
  • the total number of acryloyl groups and methacryloyl groups is 3 or 4
  • each m independently represents an integer of 0 to 10
  • the total of each m is an integer of 0 to 40. is there. However, when the total of each m is 0, any one of X is a carboxyl group.
  • the total number of acryloyl groups and methacryloyl groups is 5 or 6, each n independently represents an integer of 0 to 10, and the total of each n is an integer of 0 to 60. However, when the total of each n is 0, any one of X is a carboxyl group.
  • m is preferably an integer of 0 to 6, and more preferably an integer of 0 to 4.
  • the total of each m is preferably an integer of 2 to 40, more preferably an integer of 2 to 16, and particularly preferably an integer of 4 to 8.
  • n is preferably an integer of 0 to 6, and more preferably an integer of 0 to 4.
  • the total of each n is preferably an integer of 3 to 60, more preferably an integer of 3 to 24, and particularly preferably an integer of 6 to 12.
  • — ((CH 2 ) yCH 2 O) — or — ((CH 2 ) yCH (CH 3 ) O) — represents an oxygen atom side.
  • a form in which the terminal of X is bonded to X is preferred.
  • the compounds represented by the general formula (Z-4) or the general formula (Z-5) may be used alone or in combination of two or more.
  • a form in which all six Xs are acryloyl groups is preferable.
  • the total content of the compound represented by the general formula (Z-4) or the general formula (Z-5) in the polymerizable compound is preferably 20% by mass or more, and more preferably 50% by mass or more.
  • the compound represented by the general formula (Z-4) or the general formula (Z-5) is a conventionally known process, in which ethylene oxide or propylene oxide is ring-opened to pentaerythritol or dipentaerythritol. It can be synthesized from a step of bonding a ring-opening skeleton by an addition reaction and a step of introducing a (meth) acryloyl group by reacting, for example, (meth) acryloyl chloride with a terminal hydroxyl group of the ring-opening skeleton. Each step is a well-known step, and a person skilled in the art can easily synthesize a compound represented by the general formula (i) or (ii).
  • pentaerythritol derivatives and / or dipentaerythritol derivatives are more preferable.
  • Specific examples include compounds represented by the following formulas (a) to (f) (hereinafter also referred to as “exemplary compounds (a) to (f)”).
  • exemplary compounds (a), (f) b), (e) and (f) are preferred.
  • Examples of commercially available polymerizable compounds represented by the general formulas (Z-4) and (Z-5) include SR-494, a tetrafunctional acrylate having four ethyleneoxy chains manufactured by Sartomer, Nippon Kayaku Examples thereof include DPCA-60, which is a hexafunctional acrylate having six pentyleneoxy chains, and TPA-330, which is a trifunctional acrylate having three isobutyleneoxy chains.
  • polymerizable compound examples include urethane acrylates as described in JP-B-48-41708, JP-A-51-37193, JP-B-2-32293, and JP-B-2-16765. Also suitable are urethane compounds having an ethylene oxide skeleton as described in JP-B-58-49860, JP-B-56-17654, JP-B-62-39417, and JP-B-62-39418. Furthermore, addition polymerizable compounds having an amino structure or a sulfide structure in the molecule described in JP-A-63-277653, JP-A-63-260909, and JP-A-1-105238 are described as polymerizable compounds.
  • polymerizable compounds include urethane oligomers UAS-10, UAB-140 (Sanyo Kokusaku Pulp Co., Ltd.), UA-7200 (Shin Nakamura Chemical Co., Ltd., DPHA-40H (Nippon Kayaku Co., Ltd.), UA- 306H, UA-306T, UA-306I, AH-600, T-600, AI-600 (manufactured by Kyoeisha) and the like.
  • cyclic ether examples include those having an epoxy group such as bisphenol A type epoxy resin, JER-827, JER-828, JER-834, JER-1001, JER-1002, JER-1003.
  • JER-1055, JER-1007, JER-1009, JER-1010 manufactured by Japan Epoxy Resin Co., Ltd.
  • EPICLON 860, EPICLON 1050, EPICLON 1051, EPICLON 1055 manufactured by DIC Corporation
  • bisphenol F As type epoxy resins, JER-806, JER-807, JER-4004, JER-4005, JER-4007, JER-4010 (above, manufactured by Japan Epoxy Resins Co., Ltd.), EPICLON83 EPICLON 835 (above, manufactured by DIC Corporation), LCE-21, RE-602S (above, manufactured by Nippon Kayaku Co., Ltd.), etc., and phenol novolac type epoxy resins such as JER-152, JER-154, JER -157S70, JER-157S65 (above, manufactured by Japan Epoxy Resin Co., Ltd.), EPICLONICN-740, EPICLON N-740,
  • the details of usage methods can be arbitrarily set according to the final performance design of a coloring composition.
  • a structure having a high unsaturated group content per molecule is preferable, and in many cases, a bifunctional or higher functionality is preferable.
  • those having three or more functional groups are preferable, and further, different numbers of functional groups / different polymerizable groups (for example, acrylic acid ester, methacrylic acid ester, styrenic compound, A method of adjusting both sensitivity and strength by using a combination of vinyl ether compounds) is also effective.
  • a tri- or higher functional polymerizable compound having a different ethylene oxide chain length in that the developability of the colored composition can be adjusted and an excellent pattern forming ability can be obtained.
  • the compatibility and dispersibility with other components (for example, photopolymerization initiators, dispersions, alkali-soluble resins, etc.) contained in the colored composition are also selected and used as a polymerizable compound. This is an important factor. For example, compatibility may be improved by using a low-purity compound or using two or more kinds in combination.
  • a specific structure may be selected from the viewpoint of improving adhesion to a hard surface such as a support.
  • the content of the polymerizable compound in the composition of the present invention is preferably 0.1% by mass to 90% by mass, and more preferably 1.0% by mass to 60% by mass with respect to the total solid content in the colored composition. 2.0 mass% to 40 mass% is particularly preferable.
  • the composition of the present invention may contain only one type of polymerizable compound or two or more types. When two or more types are included, the total amount is preferably within the above range.
  • the composition of the present invention may contain a polyfunctional thiol compound having two or more mercapto groups in the molecule for the purpose of promoting the reaction of the polymerizable compound.
  • the polyfunctional thiol compound is preferably a secondary alkanethiol, and particularly preferably a compound having a structure represented by the following general formula (I).
  • n represents an integer of 2 to 4
  • L represents a divalent to tetravalent linking group.
  • the linking group L is preferably an aliphatic group having 2 to 12 carbon atoms, particularly preferably n is 2 and L is an alkylene group having 2 to 12 carbon atoms.
  • Specific examples of the polyfunctional thiol compound include compounds represented by the following structural formulas (II) to (IV), and a compound represented by (II) is particularly preferable. These polyfunctional thiols can be used alone or in combination.
  • the content of the polyfunctional thiol compound in the composition of the present invention is preferably 0.3 to 8.9% by mass, more preferably 0.8 to 6.4% by mass with respect to the total solid content in the composition. .
  • the polyfunctional thiol compound may contain only 1 type, and may contain 2 or more types. When two or more types are included, the total amount is preferably within the above range.
  • Polyfunctional thiols may be added for the purpose of improving stability, odor, resolution, developability, adhesion and the like.
  • the composition of the present invention may further contain a polymerization initiator.
  • a polymerization initiator By containing a polymerization initiator, the sensitivity can be further improved.
  • a photopolymerization initiator is preferable.
  • the photopolymerization initiator is not particularly limited as long as it has the ability to initiate polymerization of a polymerizable compound, and can be appropriately selected from known photopolymerization initiators. For example, those having photosensitivity to visible light from the ultraviolet region are preferable. Further, it may be an activator that generates some action with a photoexcited sensitizer and generates an active radical, or may be an initiator that initiates cationic polymerization according to the type of monomer.
  • the photopolymerization initiator preferably contains at least one compound having a molecular extinction coefficient of at least about 50 within a range of about 300 nm to 800 nm (more preferably 330 nm to 500 nm).
  • the photopolymerization initiator examples include halogenated hydrocarbon derivatives (for example, those having a triazine skeleton, those having an oxadiazole skeleton, etc.), acylphosphine compounds such as acylphosphine oxide, and biimidazole compounds (for example, hexagonal compounds).
  • Arylbiimidazole oxime compounds such as oxime derivatives, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, ketoxime ethers, aminoacetophenone compounds, hydroxyacetophenone, and the like, and oxime compounds are preferred.
  • the biimidazole compound for example, the description in paragraphs 0067 to 0076 of JP2013-209623A can be referred to, and the contents thereof are incorporated herein.
  • trihalomethyltriazine compounds trihalomethyltriazine compounds, benzyldimethylketal compounds, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds, acylphosphine compounds, phosphine oxide compounds, metallocene compounds, oxime compounds, triallylimidazole dimers, oniums
  • compounds selected from the group consisting of compounds, benzothiazole compounds, benzophenone compounds, acetophenone compounds and derivatives thereof, cyclopentadiene-benzene-iron complexes and salts thereof, halomethyloxadiazole compounds, and 3-aryl substituted coumarin compounds are preferred.
  • trihalomethyltriazine compounds More preferred are trihalomethyltriazine compounds, ⁇ -aminoketone compounds, acylphosphine compounds, phosphine oxide compounds, oxime compounds, triallylimidazole dimers, triarylimidazole compounds, benzimidazole compounds, onium compounds, benzophenone compounds, and acetophenone compounds.
  • At least one compound selected from the group consisting of a trihalomethyltriazine compound, an ⁇ -aminoketone compound, an oxime compound, a triallylimidazole compound, a benzophenone compound, a triarylimidazole compound, and a benzimidazole compound is particularly preferable.
  • the triarylimidazole compound may be a mixture with benzimidazole.
  • examples of the trihalomethyltriazine compound include the following compounds. Note that Ph is a phenyl group.
  • Examples of the triarylimidazole compound and the benzimidazole compound include the following compounds.
  • a commercially available product can be used as the trihalomethyltriazine compound, for example, TAZ-107 (manufactured by Midori Chemical Co., Ltd.) can also be used.
  • TAZ-107 manufactured by Midori Chemical Co., Ltd.
  • TAZ-107 manufactured by Midori Chemical Co., Ltd.
  • stepper exposure is used for curing exposure, but this exposure machine may be damaged by halogen, and it is necessary to keep the addition amount of a polymerization initiator low.
  • an oxime compound as a photopolymerization initiator for forming a fine pattern such as a solid-state imaging device.
  • halogenated hydrocarbon compound having a triazine skeleton examples include those described in Wakabayashi et al., Bull. Chem. Soc. Japan, 42, 2924 (1969), a compound described in British Patent No. 1388492, a compound described in JP-A-53-133428, a compound described in German Patent No. 3333724, F.I. C. J. Schaefer et al. Org. Chem. 29, 1527 (1964), compound described in JP-A-62-258241, compound described in JP-A-5-281728, compound described in JP-A-5-34920, US Pat. No. 4,221,976 And the compounds described in paragraph No. 0075 of JP2013-077009A, and the like.
  • acridine derivatives are exemplified as photopolymerization initiators other than those described above.
  • Specific examples include the compounds described in paragraph No. 0076 of JP2013-077009A, and the contents thereof are incorporated in the present specification.
  • Examples of the ketone compounds include compounds described in paragraph No. 0077 of JP2013-077009A, and the contents thereof are incorporated in the present specification.
  • hydroxyacetophenone compounds As the photopolymerization initiator, hydroxyacetophenone compounds, aminoacetophenone compounds, and acylphosphine compounds can also be suitably used. More specifically, for example, aminoacetophenone initiators described in JP-A-10-291969 and acylphosphine oxide initiators described in Japanese Patent No. 4225898 can also be used.
  • hydroxyacetophenone-based initiator IRGACURE-184, DAROCUR-1173, IRGACURE-500, IRGACURE-2959, IRGACURE-127 (trade names: all manufactured by BASF) can be used.
  • aminoacetophenone-based initiator commercially available products IRGACURE-907, IRGACURE-369, and IRGACURE-379 (trade names: all manufactured by BASF) can be used.
  • aminoacetophenone-based initiator compounds described in JP-A-2009-191179 whose absorption wavelength is matched with a long wave light source of 365 nm or 405 nm can also be used.
  • acylphosphine initiator commercially available products such as IRGACURE-819 and DAROCUR-TPO (trade names: both manufactured by BASF) can be used.
  • More preferred examples of the photopolymerization initiator include oxime compounds.
  • Specific examples of the oxime compound include compounds described in JP-A No. 2001-233842, compounds described in JP-A No. 2000-80068, and compounds described in JP-A No. 2006-342166.
  • Examples of oxime compounds such as oxime derivatives that are preferably used as the photopolymerization initiator in the present invention include 3-benzoyloxyiminobutan-2-one, 3-acetoxyiminobutan-2-one, and 3-propionyloxyimino.
  • oxime compounds include J.M. C. S. Perkin II (1979) pp. 1653-1660), J.M. C. S. Perkin II (1979) pp. 156-162, Journal of Photopolymer Science and Technology (1995) pp. 202-232, compounds described in JP-A No.
  • IRGACURE-OXE01 manufactured by BASF
  • IRGACURE-OXE02 manufactured by BASF
  • TR-PBG-304 manufactured by Changzhou Strong Electronic New Materials Co., Ltd.
  • oxime compounds other than those described above compounds described in JP-A-2009-519904 in which an oxime is linked to the carbazole N-position, compounds described in US Pat. No. 7,626,957 in which a hetero substituent is introduced into the benzophenone moiety, Compounds described in Japanese Patent Application Laid-Open No. 2010-15025 and US Patent Publication No. 2009-292039, in which a nitro group is introduced into the dye moiety, a ketoxime compound described in International Patent Publication No. 2009-131189, a triazine skeleton and an oxime skeleton in the same molecule
  • a compound described in US Pat. No. 7,556,910 contained therein a compound described in JP-A-2009-221114 having an absorption maximum at 405 nm and good sensitivity to a g-line light source, and the like may be used.
  • cyclic oxime compounds described in JP-A-2007-231000 and JP-A-2007-322744 can also be suitably used for the cyclic oxime compounds described in JP-A-2007-231000 and JP-A-2007-322744.
  • cyclic oxime compounds in particular, cyclic oxime compounds fused to carbazole dyes described in JP2010-32985A and JP2010-185072A have high light absorptivity and high sensitivity. preferable.
  • the compounds described in JP-A-2009-242469 having an unsaturated bond at a specific site of the oxime compound can be preferably used because high sensitivity can be achieved by regenerating the active radical from the polymerization inert radical. it can.
  • oxime compounds having a specific substituent as disclosed in JP 2007-26997A and oxime compounds having a thioaryl group as disclosed in JP 2009-191061 A are particularly preferred.
  • the oxime compound that is a photopolymerization initiator is preferably a compound represented by the following general formula (OX-1).
  • the oxime N—O bond may be an (E) oxime compound, a (Z) oxime compound, or a mixture of (E) and (Z) isomers. .
  • R and B each independently represent a monovalent substituent
  • A represents a divalent organic group
  • Ar represents an aryl group.
  • the monovalent substituent represented by R is preferably a monovalent nonmetallic atomic group.
  • the monovalent nonmetallic atomic group include an alkyl group, an aryl group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a heterocyclic group, an alkylthiocarbonyl group, and an arylthiocarbonyl group.
  • these groups may have one or more substituents.
  • the substituent mentioned above may be further substituted by another substituent.
  • substituents examples include a halogen atom, an aryloxy group, an alkoxycarbonyl group or an aryloxycarbonyl group, an acyloxy group, an acyl group, an alkyl group, and an aryl group.
  • the oxime compound has a maximum absorption wavelength in a wavelength region of 350 nm to 500 nm, preferably has an absorption wavelength in a wavelength region of 360 nm to 480 nm, and particularly preferably has a high absorbance at 365 nm and 455 nm.
  • the molar extinction coefficient at 365 nm or 405 nm of the oxime compound is preferably 1,000 to 300,000, more preferably 2,000 to 300,000, more preferably 5,000 to 200, from the viewpoint of sensitivity. Is particularly preferred.
  • a known method can be used for the molar extinction coefficient of the compound. Specifically, for example, 0.01 g of an ultraviolet-visible spectrophotometer (Varian Inc., Carry-5 spctrophotometer) is used with an ethyl acetate solvent. It is preferable to measure at a concentration of / L.
  • the content of the photopolymerization initiator is preferably 0.1 to 50% by mass, and 0.5 to 30% by mass with respect to the total solid content of the composition. More preferred is 1 to 20% by mass. By setting it as such a range, a more favorable sensitivity and pattern formation property are obtained.
  • the composition of the present invention may contain only one type of photopolymerization initiator, or may contain two or more types. When two or more types are included, the total amount is preferably within the above range.
  • the composition of the present invention may further contain an alkali-soluble resin.
  • the alkali-soluble resin is a linear organic polymer, and promotes at least one alkali-solubility in a molecule (preferably a molecule having an acrylic copolymer or a styrene copolymer as a main chain). It can be suitably selected from alkali-soluble resins having a group. From the viewpoint of heat resistance, polyhydroxystyrene resins, polysiloxane resins, acrylic resins, acrylamide resins, and acryl / acrylamide copolymer resins are preferable. From the viewpoint of development control, acrylic resins and acrylamide resins are preferable. Resins and acrylic / acrylamide copolymer resins are preferred.
  • Examples of the group that promotes alkali solubility include a carboxyl group, a phosphoric acid group, a sulfonic acid group, and a phenolic hydroxyl group.
  • the group is soluble in an organic solvent and developed with a weak alkaline aqueous solution. Possible are preferable, and (meth) acrylic acid is particularly preferable.
  • These acid groups may be used alone or in combination of two or more.
  • Examples of the monomer capable of imparting an acid group after the polymerization include, for example, a monomer having a hydroxyl group such as 2-hydroxyethyl (meth) acrylate, a monomer having an epoxy group such as glycidyl (meth) acrylate, and 2-isocyanatoethyl (methacrylate). ) Monomers having an isocyanate group such as acrylate. These monomers for introducing an acid group may be only one type or two or more types.
  • a monomer having an acid group and / or a monomer capable of imparting an acid group after polymerization (hereinafter sometimes referred to as “monomer for introducing an acid group”) .) May be polymerized as a monomer component.
  • a treatment for imparting an acid group as described later is required after the polymerization.
  • a known radical polymerization method can be applied.
  • Polymerization conditions such as temperature, pressure, type and amount of radical initiator, type of solvent, etc. when producing an alkali-soluble resin by radical polymerization can be easily set by those skilled in the art, and the conditions are determined experimentally. It can also be done.
  • a polymer having a carboxylic acid in the side chain is preferable, such as a methacrylic acid copolymer, an acrylic acid copolymer, an itaconic acid copolymer, and a crotonic acid copolymer.
  • a copolymer of (meth) acrylic acid and another monomer copolymerizable therewith is suitable as the alkali-soluble resin.
  • examples of other monomers copolymerizable with (meth) acrylic acid include alkyl (meth) acrylates, aryl (meth) acrylates, and vinyl compounds.
  • alkyl (meth) acrylate and aryl (meth) acrylate methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, pentyl (meth) acrylate,
  • vinyl compounds such as hexyl (meth) acrylate, octyl (meth) acrylate, phenyl (meth) acrylate, benzyl (meth) acrylate, tolyl (meth) acrylate, naphthyl (meth) acrylate, cyclohexyl (meth) acrylate, styrene, ⁇ -methylstyrene, vinyltoluene, glycidyl methacrylate, acrylonitrile, vinyl acetate, N-vinylpyrrolidone, tetrahydrofurfury
  • a compound represented by the following general formula (ED) and / or a compound represented by the following general formula (ED2) (hereinafter, these compounds may be referred to as “ether dimers”) are essential. It is also preferable to include a polymer (a) obtained by polymerizing the monomer component.
  • R 1 and R 2 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms which may have a substituent.
  • General formula (ED2) In general formula (ED2), R represents a hydrogen atom or an organic group having 1 to 30 carbon atoms. As a specific example of the general formula (ED2), the description in JP 2010-168539 A can be referred to.
  • the composition of this invention can form the cured coating film which was very excellent also in heat resistance and transparency.
  • the hydrocarbon group having 1 to 25 carbon atoms which may have a substituent represented by R 1 and R 2 is not particularly limited.
  • Linear or branched alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, tert-amyl, stearyl, lauryl, 2-ethylhexyl; aryl groups such as phenyl; Alicyclic groups such as cyclohexyl, tert-butylcyclohexyl, dicyclopentadienyl, tricyclodecanyl, isobornyl, adamantyl, 2-methyl-2-adamantyl; substituted with alkoxy such as 1-methoxyethyl, 1-ethoxyethyl An alkyl group substituted with an aryl group such as benzyl; and the like.
  • an acid such as methyl, ethyl, cyclohexyl, benzyl or the like, or a primary or secondary carbon substituent which is
  • ether dimer examples include dimethyl-2,2 ′-[oxybis (methylene)] bis-2-propenoate, diethyl-2,2 ′-[oxybis (methylene)] bis-2-propenoate, (N-propyl) -2,2 ′-[oxybis (methylene)] bis-2-propenoate, di (isopropyl) -2,2 ′-[oxybis (methylene)] bis-2-propenoate, di (n-butyl) ) -2,2 ′-[oxybis (methylene)] bis-2-propenoate, di (isobutyl) -2,2 ′-[oxybis (methylene)] bis-2-propenoate, di (tert-butyl) -2, 2 ′-[oxybis (methylene)] bis-2-propenoate, di (tert-butyl) -2, 2 ′-[oxybis (methylene)] bis-2-propenoate, di (tert-butyl)
  • dimethyl-2,2 ′-[oxybis (methylene)] bis-2-propenoate, diethyl-2,2 ′-[oxybis (methylene)] bis-2-propenoate, dicyclohexyl-2,2′- [Oxybis (methylene)] bis-2-propenoate and dibenzyl-2,2 ′-[oxybis (methylene)] bis-2-propenoate are preferred.
  • These ether dimers may be only one kind or two or more kinds.
  • the structure derived from the compound represented by the general formula (ED) may be copolymerized with other monomers.
  • alkali-soluble resin may contain the structural unit derived from the ethylenically unsaturated monomer shown by following formula (X).
  • Formula (X) (In Formula (X), R 1 represents a hydrogen atom or a methyl group, R 2 represents an alkylene group having 2 to 10 carbon atoms, and R 3 represents a hydrogen atom or a benzene ring which may contain a benzene ring. And represents an alkyl group of 20. n represents an integer of 1 to 15.)
  • the alkylene group of R 2 preferably has 2 to 3 carbon atoms.
  • the alkyl group of R 3 has 1 to 20 carbon atoms, more preferably 1 to 10, and the alkyl group of R 3 may contain a benzene ring.
  • Examples of the alkyl group containing a benzene ring represented by R 3 include a benzyl group and a 2-phenyl (iso) propyl group.
  • an alkali-soluble resin having a polymerizable group may be used.
  • the effect of the present invention tends to improve the solvent resistance.
  • light resistance and heat resistance tend to be further improved.
  • an alkali-soluble resin having a polymerizable group an alkali-soluble resin containing an allyl group, a (meth) acryl group, an allyloxyalkyl group or the like in the side chain is useful.
  • Examples of the above-described polymer containing a polymerizable group include a dial NR series (manufactured by Mitsubishi Rayon Co., Ltd.), Photomer 6173 (COOH-containing polyurethane acrylic oligomer. Diamond Shamrock Co.Ltd.), Biscote R-264, KS resist 106 (all manufactured by Osaka Organic Chemical Industry Co., Ltd.), Cyclomer P series, Plaxel CF200 series (all manufactured by Daicel Chemical Industries, Ltd.), Ebecryl 3800 (manufactured by Daicel UCB Co., Ltd.), and the like.
  • an alkali-soluble resin containing these polymerizable groups an isocyanate group and an OH group are reacted in advance to leave one unreacted isocyanate group and a compound containing a (meth) acryloyl group and an acrylic resin containing a carboxyl group; Urethane-modified polymerizable double bond-containing acrylic resin obtained by the above reaction, unsaturated group-containing acrylic obtained by reaction of an acrylic resin containing a carboxyl group and a compound having both an epoxy group and a polymerizable double bond in the molecule Resin, acid pendant type epoxy acrylate resin, OH group-containing acrylic resin and polymerizable double bond-containing acrylic resin obtained by reacting a polymerizable double bond, OH group-containing acrylic resin and isocyanate Resin obtained by reacting compound having polymerizable group, JP 2002-229207 A Resin obtained by basic treatment of a resin having an ester group having a leaving group such as a halogen atom or a sulf
  • alkali-soluble resin in particular, a benzyl (meth) acrylate / (meth) acrylic acid copolymer or a multi-component copolymer composed of benzyl (meth) acrylate / (meth) acrylic acid / other monomers is suitable. .
  • benzyl (meth) acrylate / (meth) acrylic acid / (meth) acrylic acid-2-hydroxyethyl copolymer copolymerized with 2-hydroxyethyl methacrylate 2 described in JP-A-7-140654 -Hydroxypropyl (meth) acrylate / polystyrene macromonomer / benzyl methacrylate / methacrylic acid copolymer, 2-hydroxy-3-phenoxypropyl acrylate / polymethyl methacrylate macromonomer / benzyl methacrylate / methacrylic acid copolymer, 2-hydroxyethyl Methacrylate / polystyrene macromonomer / methyl methacrylate / methacrylic acid copolymer, 2-hydroxyethyl methacrylate / polystyrene macromonomer / benzyl methacrylate / methacrylic acid copolymer, etc.
  • the acid value of the alkali-soluble resin is preferably 30 mgKOH / g to 200 mgKOH / g, more preferably 50 mgKOH / g to 150 mgKOH / g, and still more preferably 70 mgKOH / g to 120 mgKOH / g.
  • the weight average molecular weight (Mw) of the alkali-soluble resin is preferably 2,000 to 50,000, more preferably 5,000 to 30,000, and particularly preferably 7,000 to 20,000.
  • the content of the alkali-soluble resin is preferably 1% by mass to 15% by mass, more preferably 2% by mass with respect to the total solid content of the coloring composition. It is ⁇ 12% by mass, and particularly preferably 3% by mass to 10% by mass.
  • the composition of the present invention may contain only one kind of alkali-soluble resin, or may contain two or more kinds. When two or more types are included, the total amount is preferably within the above range.
  • the composition of the present invention may further contain a solvent.
  • the solvent is basically not particularly limited as long as the solubility of each component and the coating property of the composition are satisfied.
  • the solvent is preferably an organic solvent.
  • organic solvents include esters such as ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, cyclohexyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, and methyl lactate.
  • Ethyl lactate alkyl oxyacetate (eg, methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate (eg, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate)), 3-oxy Propionic acid alkyl esters (eg, methyl 3-oxypropionate, ethyl 3-oxypropionate, etc.
  • alkyl oxyacetate eg, methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate (eg, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate)
  • 3-oxy Propionic acid alkyl esters eg, methyl 3-oxypropionate, ethyl 3-oxyprop
  • ethers for example, diethylene glycol dimethyl ether, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, Propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, etc., and ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, 3-heptanone, and aromatic hydrocarbons Suitable examples include toluene and xylene.
  • the content of the solvent in the composition of the present invention is preferably 50 to 95% by mass, more preferably 60 to 90% by mass.
  • the composition of the present invention may contain only one type of solvent or two or more types of solvents. When two or more types are included, the total amount is preferably within the above range.
  • the composition of the present invention may further contain an ultraviolet absorber. By setting it as such a structure, generation
  • the ultraviolet absorber salicylate-based, benzophenone-based, benzotriazole-based, substituted acrylonitrile-based, and triazine-based ultraviolet absorbers can be used. In the present invention, it is particularly preferable to use an ultraviolet absorber having an aminobutadiene skeleton.
  • Examples of salicylate-based UV absorbers include phenyl salicylate, p-octylphenyl salicylate, pt-butylphenyl salicylate, and the like.
  • benzophenone-based UV absorbers examples include 2,2′-dihydroxy-4- Methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2,2 ', 4,4'-tetrahydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2,4-dihydroxybenzophenone, 2- And hydroxy-4-octoxybenzophenone.
  • benzotriazole ultraviolet absorbers examples include 2- (2′-hydroxy-3 ′, 5′-di-tert-butylphenyl) -5-chlorobenzotriazole, 2- (2′-hydroxy-3) '-Tert-butyl-5'-methylphenyl) -5-chlorobenzotriazole, 2- (2'-hydroxy-3'-tert-amyl-5'-isobutylphenyl) -5-chlorobenzotriazole, 2- ( 2'-hydroxy-3'-isobutyl-5'-methylphenyl) -5-chlorobenzotriazole, 2- (2'-hydroxy-3'-isobutyl-5'-propylphenyl) -5-chlorobenzotriazole, 2 -(2'-hydroxy-3 ', 5'-di-tert-butylphenyl) benzotriazole, 2- (2'-hydroxy-5'-methylphenyl) benzoto Azole, 2- [2'-hydroxy-5 '
  • substituted acrylonitrile ultraviolet absorbers examples include ethyl 2-cyano-3,3-diphenyl acrylate, 2-ethylhexyl 2-cyano-3,3-diphenyl acrylate, and the like.
  • triazine ultraviolet absorbers examples include 2- [4-[(2-hydroxy-3-dodecyloxypropyl) oxy] -2-hydroxyphenyl] -4,6-bis (2,4-dimethylphenyl).
  • the content of the ultraviolet absorber is preferably 0.001 to 15% by mass, more preferably 1 to 8% by mass, based on the total solid content of the composition. 2 to 6% by mass is more preferable.
  • the composition of the present invention may contain only one type of ultraviolet absorber, or may contain two or more types. When two or more types are included, the total amount is preferably within the above range.
  • Adhesion improver The composition of the present invention may further contain an adhesion improver.
  • adhesion improver include adhesion improvers described in JP-A Nos. 5-11439, 5-341532, and 6-43638.
  • the adhesion improving agent a silane coupling agent is preferable.
  • the silane coupling agent preferably has an alkoxysilyl group as a hydrolyzable group that can be chemically bonded to an inorganic material.
  • it preferably has a group that interacts or forms a bond with an organic resin and exhibits an affinity, and such a group has a (meth) acryloyl group, a phenyl group, a mercapto group, a glycidyl group, and an oxetanyl group.
  • those having a (meth) acryloyl group or a glycidyl group are preferable.
  • the silane coupling agent is also preferably a silane compound having at least two types of functional groups having different reactivity in one molecule, and particularly preferably one having an amino group and an alkoxy group as functional groups.
  • silane coupling agents include N- ⁇ -aminoethyl- ⁇ -aminopropyl-methyldimethoxysilane (trade name: KBM-602, manufactured by Shin-Etsu Chemical Co., Ltd.), N- ⁇ -aminoethyl- ⁇ -amino.
  • Propyl-trimethoxysilane (trade name KBM-603, manufactured by Shin-Etsu Chemical Co., Ltd.), N- ⁇ -aminoethyl- ⁇ -aminopropyl-triethoxysilane (trade name KBE-602, manufactured by Shin-Etsu Chemical Co., Ltd.) ), ⁇ -aminopropyl-trimethoxysilane (trade name KBM-903 manufactured by Shin-Etsu Chemical Co., Ltd.), ⁇ -aminopropyl-triethoxysilane (trade name KBE-903 manufactured by Shin-Etsu Chemical Co., Ltd.), 3-methacryloxypropyltri Methoxysilane (trade name: KBM-503, manufactured by Shin-Etsu Chemical Co., Ltd.)
  • silane coupling agent examples include, but are not limited to, the following compounds.
  • the content of the adhesion improving agent is preferably 0.001% by mass to 20% by mass, more preferably 0.01% by mass to 10% by mass and 0.1% by mass to 5% by mass with respect to the solid content of the composition of the present invention. % Is particularly preferred.
  • the composition of the present invention may contain various surfactants from the viewpoint of further improving coatability.
  • various surfactants such as a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and a silicone-based surfactant can be used.
  • the composition of the present invention contains a fluorosurfactant
  • the liquid properties (particularly fluidity) when prepared as a coating liquid are further improved. Sex can be improved more. That is, when a film is formed using a coating liquid to which a composition containing a fluorosurfactant is applied, the wettability to the coated surface is reduced by reducing the interfacial tension between the coated surface and the coating liquid. Is improved, and the coating property to the coated surface is improved. For this reason, even when a thin film of about several ⁇ m is formed with a small amount of liquid, it is effective in that it is possible to more suitably form a film having a uniform thickness with small thickness unevenness.
  • the fluorine content in the fluorosurfactant is preferably 3% by mass to 40% by mass, more preferably 5% by mass to 30% by mass, and particularly preferably 7% by mass to 25% by mass.
  • a fluorine-based surfactant having a fluorine content within this range is effective in terms of uniformity of coating film thickness and liquid-saving properties, and has good solubility in the composition.
  • fluorosurfactant examples include Megafac F171, F172, F173, F176, F176, F177, F141, F142, F143, F144, R30, F437, F475, F479, F482, F554, F780, F780, F781 (above DIC Corporation), Florard FC430, FC431, FC171 (above, Sumitomo 3M Limited), Surflon S-382, SC-101, SC-103, SC-104, SC-105, SC1068, SC-381, SC-383, S393, KH-40 (above, manufactured by Asahi Glass Co., Ltd.) and the like.
  • nonionic surfactant examples include glycerol, trimethylolpropane, trimethylolethane, and ethoxylates and propoxylates thereof (for example, glycerol propoxylate, glycerol ethoxylate, etc.), polyoxyethylene lauryl ether, polyoxyethylene Stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, sorbitan fatty acid ester (Pluronic L10, L31, L61, L62 manufactured by BASF, 10R5, 17R2, 25R2, Tetronic 304, 701, 704, 901, 904, 150R1) Solsperse 20000 (Lubrizol Japan Co., Ltd.), and the like.
  • cationic surfactant examples include phthalocyanine derivatives (trade name: EFKA-745, manufactured by Morishita Sangyo Co., Ltd.), organosiloxane polymer KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), (meth) acrylic acid ( Co) polymer polyflow no. 75, no. 90, no. 95 (manufactured by Kyoeisha Chemical Co., Ltd.) and W001 (manufactured by Yusho Co., Ltd.).
  • phthalocyanine derivatives trade name: EFKA-745, manufactured by Morishita Sangyo Co., Ltd.
  • organosiloxane polymer KP341 manufactured by Shin-Etsu Chemical Co., Ltd.
  • (meth) acrylic acid ( Co) polymer polyflow no. 75, no. 90, no. 95 manufactured by Kyoeisha Chemical Co., Ltd.
  • W001 manufactured by Yusho Co., Ltd.
  • anionic surfactants include W004, W005, W017 (manufactured by Yusho Co., Ltd.) and the like.
  • silicone surfactant examples include “Toray Silicone DC3PA”, “Toray Silicone SH7PA”, “Toray Silicone DC11PA”, “Tore Silicone SH21PA”, “Tore Silicone SH28PA”, “Toray Silicone” manufactured by Toray Dow Corning Co., Ltd.
  • the addition amount of the surfactant is preferably 0.001% by mass to 2.0% by mass, more preferably 0.001% by mass with respect to the total mass of the composition. 005 mass% to 1.0 mass%.
  • the composition of the present invention may contain only one type of surfactant or two or more types of surfactant. When two or more types are included, the total amount is preferably within the above range.
  • the composition of the present invention may contain a polymerization inhibitor.
  • polymerization inhibitors include hydroquinone, p-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, t-butylcatechol, benzoquinone, 4,4′-thiobis (3-methyl-6-t-butylphenol ), 2,2′-methylenebis (4-methyl-6-tert-butylphenol), N-nitrosophenylhydroxyamine primary cerium salt, and the like.
  • the content of the polymerization inhibitor is preferably 0.001 to 1% by mass, more preferably 0.005 to 0.1% by mass, based on the total solid content of the composition of the present invention.
  • composition of the present invention may contain a polymerization inhibitor.
  • polymerization inhibitors include hydroquinone, p-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, t-butylcatechol, benzoquinone, 4,4′-thiobis (3-methyl-6-t-butylphenol ), 2,2′-methylenebis (4-methyl-6-tert-butylphenol), N-nitrosophenylhydroxyamine primary cerium salt, and the like.
  • the content of the polymerization inhibitor is preferably 0.001 to 1% by mass, more preferably 0.005 to 0.1% by mass, based on the total solid content of the composition of the present invention. Only one type of polymerization inhibitor may be used, or two or more types may be used in combination.
  • the method for producing the composition of the present invention includes C.I. I. Pigment green 36, C.I. I. Pigment yellow 150, C.I. I. Pigment Yellow 185 and a resin, C.I. I. Pigment Green 36 is contained in an amount of 80 to 86 parts by mass; I. Pigment yellow 150 and C.I. I. Pigment Yellow 185 has a mass ratio in the range of 65.4: 35.6 to 79.0: 21.0, an acid value of the resin of 20 to 50, and a ratio of amine value to acid value of 0.00. It is characterized in that a co-dispersion liquid of 85 to 1.45 is used. Moreover, the manufacturing method of the composition of this invention is C.I.
  • the cured film of the present invention is formed by curing the composition of the present invention. Such a cured film is preferably used for a color filter.
  • the composition of the present invention is applied onto a support to form a radiation-sensitive composition layer, unnecessary portions are removed, and a colored pattern is formed.
  • the pattern forming method of the present invention can be suitably applied to the formation of a colored pattern (pixel) included in a color filter.
  • the composition of the present invention may produce a color filter by pattern formation by a so-called photolithography method, or may form a pattern by dry etching.
  • a method for producing a color filter including a step of developing and removing a non-exposed portion to form a colored pattern.
  • a color filter comprising: forming a photoresist layer on the substrate; patterning the photoresist layer by exposure and development to obtain a resist pattern; and dry etching the colored layer using the resist pattern as an etching mask.
  • the process of forming a radiation sensitive composition layer >> In the step of forming the radiation-sensitive composition layer, the radiation-sensitive composition layer is formed on the support by applying the composition of the present invention.
  • a solid-state imaging in which an imaging element (light receiving element) such as a CCD (Charge Coupled Device) or a CMOS (Complementary Metal-Oxide Semiconductor) is provided on a substrate (for example, a silicon substrate).
  • An element substrate can be used.
  • the colored pattern in the present invention may be formed on the imaging element forming surface side (front surface) of the solid-state imaging element substrate, or may be formed on the imaging element non-forming surface side (back surface).
  • a light shielding film may be provided between the colored patterns in the solid-state image sensor or on the back surface of the substrate for the solid-state image sensor.
  • an undercoat layer may be provided on the support for improving adhesion with the upper layer, preventing diffusion of substances, or flattening the substrate surface.
  • a solvent, an alkali-soluble resin, a polymerizable compound, a polymerization inhibitor, a surfactant, a photopolymerization initiator, and the like can be blended, and each of these components is derived from the components blended in the above-described composition of the present invention. It is preferable to select appropriately.
  • composition of the present invention As a method for applying the composition of the present invention on the support, various coating methods such as slit coating, ink jet method, spin coating, cast coating, roll coating, screen printing method and the like can be applied.
  • Drying (pre-baking) of the radiation-sensitive composition layer coated on the support can be performed at a temperature of 50 ° C. to 140 ° C. for 10 seconds to 300 seconds using a hot plate, oven or the like.
  • Exposure Step the radiation-sensitive composition layer formed in the radiation-sensitive composition layer forming step is subjected to pattern exposure through a mask having a predetermined mask pattern using an exposure apparatus such as a stepper, for example. Thereby, a cured film is obtained.
  • radiation (light) that can be used for exposure ultraviolet rays such as g-line and i-line are particularly preferable (particularly preferably i-line).
  • Irradiation dose is more preferably 30mJ / cm 2 ⁇ 1500mJ / cm 2 is preferably 50mJ / cm 2 ⁇ 1000mJ / cm 2, 80mJ / cm 2 ⁇ 500mJ / cm 2 is particularly preferred.
  • the thickness of the cured film (colored film) is preferably 1.0 ⁇ m or less, more preferably 0.1 ⁇ m to 0.9 ⁇ m, and further preferably 0.2 ⁇ m to 0.8 ⁇ m. It is preferable to set the film thickness to 1.0 ⁇ m or less because high resolution and high adhesion can be obtained.
  • a cured film having a thin film thickness of 0.7 ⁇ m or less can also be suitably formed, and the obtained cured film is developed in a pattern forming process described later, thereby forming a thin film.
  • the coloring pattern excellent in developability, surface roughness suppression, and pattern shape can be obtained.
  • the developer is preferably an organic alkali developer that does not cause damage to the underlying image sensor or circuit.
  • the development temperature is usually 20 ° C. to 30 ° C., and the development time is conventionally 20 seconds to 90 seconds. In order to remove the residue more, in recent years, it may be carried out for 120 seconds to 180 seconds. Furthermore, in order to further improve residue removability, the process of shaking off the developer every 60 seconds and further supplying a new developer may be repeated several times.
  • alkaline agent used in the developer examples include ammonia water, ethylamine, diethylamine, dimethylethanolamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, benzyltrimethylammonium hydroxide.
  • Organic alkaline compounds such as choline, pyrrole, piperidine, 1,8-diazabicyclo- [5,4,0] -7-undecene, and the concentration of these alkaline agents is 0.001 to 10% by mass
  • An alkaline aqueous solution diluted with pure water so as to be preferably 0.01% by mass to 1% by mass is preferably used as the developer.
  • an inorganic alkali may be used for the developer, and as the inorganic alkali, for example, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogencarbonate, sodium oxalate, sodium metaoxalate and the like are preferable.
  • a developer composed of such an alkaline aqueous solution it is generally washed (rinsed) with pure water after development.
  • post-bake heat treatment after drying. If a multicolor coloring pattern is to be formed, a cured film can be produced by sequentially repeating the above steps for each color. Thereby, a color filter is obtained.
  • the post-baking is a heat treatment after development for complete curing, and a heat curing treatment is usually performed at 100 ° C. to 240 ° C., preferably 200 ° C. to 240 ° C.
  • This post-bake treatment is performed continuously or batchwise using a heating means such as a hot plate, a convection oven (hot air circulation dryer), a high-frequency heater, or the like so that the coating film after development is in the above-described condition. be able to.
  • the manufacturing method of this invention may have a well-known process as a manufacturing method of the color filter for solid-state image sensors as a process other than the above as needed.
  • a curing step of curing the formed colored pattern by heating and / or exposure may be included as necessary.
  • the colored composition according to the present invention when used, for example, clogging of the nozzle of the coating device discharge section or the piping section, contamination due to adhesion, sedimentation, or drying of the colored composition or pigment in the coating machine may occur. is there. Therefore, in order to efficiently clean the contamination caused by the composition of the present invention, it is preferable to use the solvent related to the present composition as the cleaning liquid.
  • the cleaning liquids described in JP-A-2007-2101, JP-A-2007-2102, JP-A-2007-281523 and the like can also be suitably used for cleaning and removing the colored composition according to the present invention.
  • alkylene glycol monoalkyl ether carboxylates and alkylene glycol monoalkyl ethers are preferred. These solvents may be used alone or in combination of two or more.
  • the mass ratio of the solvent having a hydroxyl group and the solvent having no hydroxyl group is from 1/99 to 99/1, preferably from 10/90 to 90/10, more preferably from 20/80 to 80/20.
  • a mixed solvent of propylene glycol monomethyl ether acetate (PGMEA) and propylene glycol monomethyl ether (PGME) the ratio is particularly preferably 60/40.
  • a surfactant related to the present composition described above may be added to the cleaning liquid.
  • the color filter of the present invention uses the composition of the present invention, the exposure can be performed with excellent exposure margin, and the formed colored pattern (colored pixel) is excellent in pattern shape, and the pattern surface is rough and developed. Since the residue in the portion is suppressed, the color characteristics are excellent.
  • the color filter of the present invention can be suitably used for a solid-state imaging device such as a CCD or CMOS, and is particularly suitable for a CCD or CMOS having a high resolution exceeding 1 million pixels.
  • the color filter for a solid-state imaging device of the present invention can be used as a color filter disposed between, for example, a light receiving portion of each pixel constituting a CCD or CMOS and a microlens for condensing light.
  • the size (pattern width) of the colored pattern (colored pixel) is preferably 2.5 ⁇ m or less, more preferably 2.0 ⁇ m or less, and particularly preferably 1.7 ⁇ m or less.
  • an oxygen blocking film may be formed on the color filter.
  • the oxygen barrier film is preferably provided on the surface of the color filter layer made of the composition of the present invention. Examples of the oxygen barrier film used in the present invention include an oxygen barrier film having an oxygen permeability of 200 ml / m 2 ⁇ day ⁇ atm or more.
  • the description in paragraphs 0217 to 0221 of JP 2011-248197 A can be referred to, and the contents thereof are incorporated in the present specification.
  • the solid-state imaging device of the present invention includes the above-described color filter of the present invention.
  • the configuration of the solid-state imaging device of the present invention is a configuration provided with the color filter in the present invention, and is not particularly limited as long as it is a configuration that functions as a solid-state imaging device. .
  • a transfer electrode made of a plurality of photodiodes and polysilicon constituting a light receiving area of a solid-state imaging device (CCD image sensor, CMOS image sensor, etc.) is provided on a support, and the photodiode and the transfer electrode are disposed on the support
  • light collecting means for example, a microlens, etc., the same shall apply hereinafter
  • the color filter of the present invention can be used not only for the solid-state imaging device but also for image display devices such as liquid crystal display devices and organic EL display devices, and is particularly suitable for use in liquid crystal display devices.
  • the liquid crystal display device provided with the color filter of the present invention can display a high-quality image with a good display image color and excellent display characteristics.
  • display devices For the definition of display devices and details of each display device, refer to, for example, “Electronic Display Device (Akio Sasaki, Kogyo Kenkyukai, 1990)”, “Display Device (Junsho Ibuki, Industrial Books Co., Ltd.) Issued in the first year).
  • the liquid crystal display device is described, for example, in “Next-generation liquid crystal display technology (edited by Tatsuo Uchida, Industrial Research Co., Ltd., published in 1994)”.
  • the liquid crystal display device to which the present invention can be applied is not particularly limited, and can be applied to, for example, various types of liquid crystal display devices described in the “next generation liquid crystal display technology”.
  • the color filter of the present invention may be used in a color TFT liquid crystal display device.
  • the color TFT liquid crystal display device is described in, for example, “Color TFT liquid crystal display (issued in 1996 by Kyoritsu Publishing Co., Ltd.)”.
  • the present invention is applied to a liquid crystal display device with a wide viewing angle, such as a horizontal electric field driving method such as IPS and a pixel division method such as MVA, STN, TN, VA, OCS, FFS, and R-OCB. it can.
  • the color filter in the present invention can be used for a bright and high-definition COA (Color-filter On Array) system.
  • COA Color-filter On Array
  • the required characteristics for the color filter layer require the required characteristics for the interlayer insulating film, that is, the low dielectric constant and the resistance to the stripping solution, in addition to the normal required characteristics as described above.
  • the color filter of the present invention since a dye multimer excellent in hue is used, the color purity, light transmittance, etc. are good and the color pattern (pixel) is excellent in color, so the resolution is high and the long-term durability is excellent.
  • a COA type liquid crystal display device can be provided.
  • a resin film may be provided on the color filter layer.
  • micro O red system micro OLED
  • the liquid crystal display device provided with the color filter of the present invention includes various members such as an electrode substrate, a polarizing film, a retardation film, a backlight, a spacer, and a viewing angle guarantee film.
  • the color filter of the present invention can be applied to a liquid crystal display device composed of these known members.
  • these components for example, “'94 Liquid Crystal Display Peripheral Materials / Chemicals Market (Kentaro Shima CMC 1994)”, “2003 Liquid Crystal Related Markets Current Status and Future Prospects (Volume 2)” Fuji Chimera Research Institute, Ltd., published in 2003) ”.
  • backlighting SID meeting Digest 1380 (2005) (A. Konno et.al), Monthly Display December 2005, pages 18-24 (Yasuhiro Shima), pages 25-30 (Takaaki Yagi), etc. Are listed.
  • the color filter according to the present invention When the color filter according to the present invention is used in a liquid crystal display device, a high contrast can be realized when combined with a conventionally known three-wavelength tube of a cold cathode tube, and further, red, green and blue LED light sources (RGB-LED).
  • RGB-LED red, green and blue LED light sources
  • PGMEA propylene glycol monomethyl ether acetate
  • the mixed solution was mixed and dispersed with a bead mill (high pressure disperser NANO-3000-10 with a pressure reducing mechanism (manufactured by Nippon BEE Co., Ltd.)) for 3 hours using 0.3 mm diameter zirconia beads.
  • a pigment dispersion composition G-1 was prepared.
  • the weight average molecular weight of the specific dispersion resin (A) is 10,000.
  • the amine value of the specific dispersion resin (A) is 45 (mgKOH / g), and the acid value is 32.3 (mgKOH / g). The amine value and acid value of the specific dispersion resin (A) were measured by the methods described above.
  • Pigment dispersion compositions G-2 to G-18 were obtained in the same manner except that the components in the pigment dispersion composition G-1 were changed as shown in the following table.
  • the obtained sulfonated paste was redispersed in 5000 parts of water (pH of the redispersed slurry was 2.3), and 25% by mass of caustic soda solution was added with stirring to adjust the pH to 11.5.
  • the reaction solution changed from a yellow slurry state to a red solution state.
  • the pH was finely adjusted every 5 minutes and continued for 1 hour. Furthermore, it heated at 60 degreeC at pH11.5, and stirred for 3 hours.
  • an aqueous solution in which 47 parts of aluminum chloride (hexahydrate) was dissolved was added dropwise little by little to obtain a yellow precipitate.
  • the pH after addition of the entire amount was 3.5. Filtration, washing with water and drying yielded 40 parts of pigment derivative (A).
  • ⁇ Pigment derivative (B)> Into 300 parts of methanol, 20 parts of 5-aminobenzimidazolone and 25 parts of cyanuric chloride were charged and reacted at 20 ° C. or lower for 2 hours, and then 34 parts of aminoethanesulfonic acid, 27 parts of sodium hydroxide and 700 parts of water were added. Heat to reflux for 4 hours. Next, the mixture was cooled to 60 ° C, charged with 170 parts of a 10 mass% aqueous aluminum sulfate solution, stirred at 60 ° C for 1 hour, filtered, washed with water, and dried to obtain 60 parts of a pigment dispersant (B).
  • ⁇ Pigment derivative (C)> In 500 parts of methanol, 40 parts of 5-aminobenzimidazolone and 25 parts of cyanuric chloride are charged and reacted at 50 ° C. for 2 hours, and then 18 parts of 6-aminocaproic acid, 22 parts of sodium hydroxide and 1000 parts of water are added. Heated to reflux for hours. Next, the mixture was cooled to 60 ° C., charged with 450 parts of a 10% by mass stearylamine acetate aqueous solution, stirred at 60 ° C. for 1 hour, filtered, washed with water, and dried to obtain 94 parts of a pigment dispersant (C).
  • the radiation sensitive compositions of Examples 2 to 13 and Comparative Examples 1 to 8 were similarly obtained except that the components in the radiation sensitive composition of Example 1 were changed as shown in Table 7 below. Obtained.
  • the radiation-sensitive composition of Example 3 was blended with the above-described pigment dispersion compositions G-3, G-4, and G-5 at a mass ratio of 83: 12: 5.
  • the following evaluation was performed about the radiation-sensitive composition obtained by the Example and the comparative example.
  • ⁇ Filtration evaluation> About the composition made from a radiation sensitivity obtained by the Example and the comparative example, filterability was evaluated by measuring a filtration flow rate using the filtration filter CWOHOS1S3 by Entegris. The results are shown in the table below.
  • the time during which the radiation-sensitive composition layer is allowed to stand before exposure (PCD (post coating delay) is set to two conditions of 0 hour or 24 hours) .
  • PCD post coating delay
  • paddle development was performed on the radiation-sensitive composition layer after exposure using a 0.3% aqueous solution of tetramethylammonium hydroxide (TMAH) at 23 ° C. for 60 seconds.
  • TMAH tetramethylammonium hydroxide
  • the line width of the pattern was observed using a length measurement SEM (trade name: S-7800H, manufactured by Hitachi, Ltd.). And the difference of the average value of the line width of each pattern was calculated
  • TMAH tetramethylammonium hydroxide
  • Residue amount is less than 0.5% 4: Residue amount is 0.5% or more and less than 0.9% 3: Residue amount is 0.9% or more and less than 1.3% 2: Residue amount is 1.3 % Or more, less than 2.0% 1: Residue amount is 2.0% or more
  • the obtained colored resin film for color filter is placed between the observation lens and the light source of the optical microscope to irradiate the light toward the observation lens, and the transmitted light state is installed by a digital camera with a magnification of 1000 times Was observed with an optical microscope.
  • a digital camera installed in the optical microscope is equipped with a CCD with 1.28 million pixels, and the surface of the coating film in a transmitted light state was photographed.
  • the photographed image was stored as digitally converted data (digital image) in an 8-bit bitmap format.
  • the film surface was photographed on 20 arbitrarily selected areas.
  • the digitally converted data was digitized and stored as a density distribution of 256 gradations in which the luminance of each of the three primary colors RGB was 0 to 255.
  • the stored digital image was divided into a lattice shape so that one lattice size corresponds to 2 ⁇ m square on the actual substrate, and the luminance in one partition was averaged.
  • 2 ⁇ m on the actual substrate was 2 mm on the captured image
  • the image size on the display was 452 mm ⁇ 352 mm.
  • the total number of sections in one area was 39976. For all the sections in each region, an arbitrary luminance and the average luminance of all adjacent sections adjacent to it were measured.
  • each symbol means the following compounds.
  • XAN Abbreviated resin of cyclohexanone 1: Weight average molecular weight 11,000 Resin 2: Weight average molecular weight 14,000 Resin 3: Weight average molecular weight 12,000 Resin 4: Weight average molecular weight 11,000
  • DPCA-20 Additive 1: UV-503, manufactured by Daito Chemical Co., Ltd.
  • Additive 2 p-methoxyphenol Additive 3: (Product name: SM-1, manufactured by Kobe Natural Products Chemicals)

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PCT/JP2015/054421 2014-02-28 2015-02-18 感放射線性組成物およびその製造方法、硬化膜、カラーフィルタおよびその製造方法、パターン形成方法、固体撮像素子ならびに画像表示装置 WO2015129521A1 (ja)

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WO2018116988A1 (ja) * 2016-12-22 2018-06-28 東レ株式会社 有機ｅｌ表示装置
KR102300781B1 (ko) * 2017-08-31 2021-09-10 후지필름 가부시키가이샤 경화성 조성물, 경화물, 컬러 필터, 컬러 필터의 제조 방법, 고체 촬상 소자 및 화상 표시 장치
KR102440063B1 (ko) * 2018-01-10 2022-09-02 동우 화인켐 주식회사 착색 감광성 조성물, 컬러필터 및 촬상 소자

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