WO2019059075A1 - 着色組成物、硬化膜、パターン形成方法、カラーフィルタ、固体撮像素子及び画像表示装置 - Google Patents
着色組成物、硬化膜、パターン形成方法、カラーフィルタ、固体撮像素子及び画像表示装置 Download PDFInfo
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- WO2019059075A1 WO2019059075A1 PCT/JP2018/033896 JP2018033896W WO2019059075A1 WO 2019059075 A1 WO2019059075 A1 WO 2019059075A1 JP 2018033896 W JP2018033896 W JP 2018033896W WO 2019059075 A1 WO2019059075 A1 WO 2019059075A1
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- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- C—CHEMISTRY; METALLURGY
- 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
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/109—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing other specific dyes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/372—Sulfides, e.g. R-(S)x-R'
- C08K5/3725—Sulfides, e.g. R-(S)x-R' containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/378—Thiols containing heterocyclic rings
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/004—Diketopyrrolopyrrole dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- 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
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0034—Mixtures of two or more pigments or dyes of the same type
-
- 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
-
- 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
- C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
- C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
- C09B68/44—Non-ionic groups, e.g. halogen, OH or SH
- C09B68/441—Sulfonic acid derivatives, e.g. sulfonic acid amides or sulfonic acid esters
-
- 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
- C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
- C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
- C09B68/44—Non-ionic groups, e.g. halogen, OH or SH
- C09B68/443—Carboxylic acid derivatives, e.g. carboxylic acid amides, carboxylic acid esters or CN groups
-
- 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
- C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
- C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
- C09B68/44—Non-ionic groups, e.g. halogen, OH or SH
- C09B68/444—Polyether
-
- 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
- C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
- C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
- C09B68/44—Non-ionic groups, e.g. halogen, OH or SH
- C09B68/446—Amines or polyamines, e.g. aminopropyl, 1,3,4,-triamino-pentyl or polyethylene imine
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/41—Organic pigments; Organic dyes
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
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- G02B5/20—Filters
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- G—PHYSICS
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- 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
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—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
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- 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
- 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
-
- 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
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
-
- 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
Definitions
- the present invention relates to a coloring composition. More specifically, the present invention relates to a coloring composition containing a pigment having a diketopyrrolopyrrole skeleton. The invention also relates to a cured film using a coloring composition, a pattern forming method, a color filter, a solid-state imaging device, and an image display device.
- Color filters are used as key devices for displays and optical elements.
- the color filter usually has pixels (colored patterns) of three primary colors of red, green and blue, and plays a role of separating transmitted light into the three primary colors.
- a coloring composition for forming a red pixel As a coloring composition for forming a red pixel, a diketopyrrolopyrrole pigment such as Color Index Pigment Red 254 is used (see Patent Document 1).
- Patent Document 2 describes an invention relating to an organic transistor having a thin film formed using an organic semiconductor.
- organic semiconductor a compound having a diketopyrrolopyrrole skeleton is mentioned.
- Patent Document 2 mentions a compound having a diketopyrrolopyrrole skeleton as one type of organic semiconductor, Patent Document 2 mentions a compound having a diketopyrrolopyrrole skeleton and a compound having a curable group. There is no description or suggestion about the coloring composition to be contained.
- an object of the present invention is to provide a coloring composition capable of forming a cured film having desired spectral characteristics even if it is a thin film.
- Another object of the present invention is to provide a cured film, a pattern forming method, a color filter, a solid-state imaging device, and an image display device.
- the present invention provides the following. ⁇ 1> A pigment A having a structure in which an aromatic ring group in which an oxygen atom, a sulfur atom or a group to which a nitrogen atom is bonded is introduced to an aromatic ring is bonded to a diketopyrrolopyrrole skeleton; A colored composition comprising a compound having a curable group, Colored composition whose content of the pigment A in the total solid of a coloring composition is 40 mass% or more.
- the pigmented composition according to ⁇ 1> or ⁇ 2> which is a compound represented by the following formula (1);
- R 11 and R 13 each independently represent a substituent
- R 12 and R 14 each independently represent a hydrogen atom, an alkyl group, an aryl group or a heteroaryl group
- n11 and n13 each independently represent an integer of 0 to 4
- X 12 and X 14 each independently represent an oxygen atom, a sulfur atom or a nitrogen atom, When X 12 is an oxygen atom or a sulfur atom, m 12 represents 1; and when X 12 is a nitrogen atom, m 12 represents 2; If X 14 is an oxygen atom or a sulfur atom, m14 represents 1, if X 14 is a nitrogen atom, m14 represents 2.
- the pigmented composition according to ⁇ 1> or ⁇ 2> which is a compound represented by the following formula (2):
- R 11 and R 13 each independently represent a substituent
- R 12 and R 14 each independently represent a hydrogen atom, an alkyl group, an aryl group or a heteroaryl group
- n11 and n13 each independently represent an integer of 0 to 4
- X 12 and X 14 each independently represent an oxygen atom, a sulfur atom or a nitrogen atom, When X 12 is an oxygen atom or a sulfur atom, m 12 represents 1; and when X 12 is a nitrogen atom, m 12 represents 2; If X 14 is an oxygen atom or a sulfur atom, m14 represents 1, if X 14 is a nitrogen atom, m14 represents 2.
- ⁇ 7> The colored composition according to any one of ⁇ 1> to ⁇ 6>, wherein the compound having a curable group contains a compound having an ethylenically unsaturated group, and further contains a photopolymerization initiator.
- a ⁇ 8> coloring composition contains the monomer which has an ethylenically unsaturated group, and resin, A ratio of a mass M1 of a monomer having an ethylenically unsaturated group contained in the coloring composition to a mass B1 of a resin contained in the coloring composition is less than or equal to 0.2.
- the coloring composition in any one of 7>.
- ⁇ 9> A cured film obtained from the coloring composition according to any one of ⁇ 1> to ⁇ 8>.
- ⁇ 10> A step of forming a colored composition layer on a support using the colored composition according to any one of ⁇ 1> to ⁇ 8>, and a colored composition layer by a photolithography method or a dry etching method And forming a pattern.
- the color filter which has a cured film as described in ⁇ 11> ⁇ 9>.
- the solid-state image sensor which has a cured film as described in ⁇ 12> ⁇ 9>.
- the image display apparatus which has a cured film as described in ⁇ 13> ⁇ 9>.
- the coloring composition which can form the cured film which has a desired spectral characteristic can be provided.
- a cured film, a pattern formation method, a color filter, a solid-state imaging device, and an image display apparatus can be provided.
- the notation not describing substitution and non-substitution includes a group having a substituent together with a group having no substituent.
- 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).
- "exposure” means not only exposure using light but also drawing using particle beams such as electron beams and ion beams.
- a bright line spectrum of a mercury lamp far ultraviolet rays represented by an excimer laser, extreme ultraviolet rays (EUV light), actinic rays such as X-rays, electron beams and the like can be mentioned.
- EUV light extreme ultraviolet rays
- a numerical range represented using “to” means a range including the numerical values described before and after “to” as the lower limit value and the upper limit value.
- total solids refers to the total amount of all components of the composition excluding the solvent.
- (meth) acrylate represents both or either of acrylate and methacrylate
- (meth) acryl represents both or either of acrylic and methacryl
- Allyl represents both or any of allyl and methallyl
- (meth) acryloyl represents both or any of acryloyl and methacryloyl.
- step does not only mean an independent step, but if the intended function of that step is achieved even if it can not be clearly distinguished from other steps, this term include.
- the weight average molecular weight (Mw) and the number average molecular weight (Mn) are defined as polystyrene conversion values measured by gel permeation chromatography (GPC).
- the coloring composition of the present invention is A pigment A having a structure in which an aromatic ring group in which an oxygen atom, a sulfur atom or a group to which a nitrogen atom is bonded is introduced to an aromatic ring is bonded to a diketopyrrolopyrrole skeleton; A compound having a curable group, It is characterized in that the content of the pigment A in the total solid content of the coloring composition is 40% by mass or more.
- the coloring composition of the present invention contains 40% by mass or more of the pigment A in the total solid content of the coloring composition, but the pigment A has a red color value higher than that of a conventional red pigment, so A cured film having desired spectral characteristics can be formed.
- the pigment A has a structure in which an aromatic ring group in which the above-described group is introduced is bonded to a diketopyrrolopyrrole skeleton, and therefore, transition is caused by extension of the HOMO (Highest Occupied Molecular Orbital) -LUMO (Lowest Unoccupied Molecular Orbital) transition.
- the color value of red is high because the moment is increased and, as a result, the molar absorption coefficient ⁇ in the red wavelength region (for example, 450 to 600 nm) of pigment A is increased.
- the pigment A has a red color value higher than that of a conventional red pigment, the desired spectrum can be obtained with a blending amount smaller than the blending amount required to achieve the same spectral characteristics as the conventional red pigment.
- the blending amount of components other than the pigment can be increased, and the degree of freedom in formulation design is high.
- the pigment A is excellent also in the dispersibility in a composition.
- the coloring composition of the present invention comprises a pigment A having a structure in which an aromatic ring group in which an oxygen atom, a sulfur atom or a group having a nitrogen atom bonded thereto is introduced to an aromatic ring is bonded to a diketopyrrolopyrrole skeleton. contains.
- This pigment is a pigment having a diketopyrrolopyrrole skeleton.
- the aromatic ring group is preferably a group represented by formula (AR-1).
- Formula (AR-1) In the formula, R 1 represents a substituent, R 2 represents a hydrogen atom, an alkyl group, an aryl group or a heteroaryl group, n1 represents an integer of 0 to 4; X represents an oxygen atom, a sulfur atom or a nitrogen atom, When X is an oxygen atom or a sulfur atom, m is 1; when X is a nitrogen atom, m is 2; The wavy line indicates the binding site to the diketopyrrolopyrrole skeleton.
- examples of the substituent represented by R 1 include the groups listed as the substituent T described later, and an alkyl group, an aryl group, a halogen atom, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group And a heteroaryloxycarbonyl group, an amido group, a cyano group, a nitro group, a trifluoromethyl group, a sulfoxide group, a sulfo group and the like are mentioned as preferable specific examples.
- R 2 represents a hydrogen atom, an alkyl group, an aryl group or a heteroaryl group.
- the carbon number of the alkyl group represented by R 2 is preferably 1 to 20, more preferably 1 to 15, and still more preferably 1 to 8.
- the alkyl group may be linear, branched or cyclic, and is preferably linear or branched.
- the alkyl group may have a substituent.
- the group mentioned by the substituent T mentioned later is mentioned.
- Number of carbon atoms of the aryl group represented by R 2 is preferably 6 to 30, more preferably 6 to 20, more preferably 6 to 12.
- the aryl group may have a substituent.
- the group mentioned by the substituent T mentioned later is mentioned.
- the heteroaryl group represented by R 2 may be a single ring or a fused ring.
- the number of heteroatoms constituting the ring of the heteroaryl group is preferably 1 to 3.
- the heteroatom constituting the ring of the heteroaryl group is preferably a nitrogen atom, an oxygen atom or a sulfur atom.
- the heteroaryl group is preferably a 5- or 6-membered ring.
- the number of carbon atoms constituting the ring of the heteroaryl group is preferably 3 to 30, more preferably 3 to 18, and still more preferably 3 to 12.
- the heteroaryl group may have a substituent. As a substituent, the group mentioned by the substituent T mentioned later is mentioned.
- n1 represents an integer of 0 to 4, preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and still more preferably 0 or 1. Particularly preferred is 0.
- X represents an oxygen atom, a sulfur atom or a nitrogen atom. It is preferably an oxygen atom or a nitrogen atom because the molar absorption coefficient of the pigment A at a wavelength of 500 to 600 nm can be further increased, and an oxygen atom is particularly preferable.
- R 2 is preferably a hydrogen atom or an alkyl group because it can further increase the molar absorption coefficient of the pigment A at a wavelength of 500 to 600 nm, and it is preferably an alkyl group More preferable.
- a wavy line represents a binding site to the diketopyrrolopyrrole skeleton.
- the diketopyrrolopyrrole skeleton means the following structure.
- a wavy line represents a bonding position with a substituent such as a group represented by Formula (AR-1).
- substituent other than the group represented by Formula (AR-1) include an aryl group and the like.
- the aryl group may have a substituent.
- the group mentioned by the substituent T mentioned later is mentioned.
- the pigment A is preferably a compound represented by the following formula (1), and is a compound represented by the following formula (2) because the molar absorption coefficient at a wavelength of 500 to 600 nm can be further enhanced. Is more preferred.
- R 11 and R 13 each independently represent a substituent
- R 12 and R 14 each independently represent a hydrogen atom, an alkyl group, an aryl group or a heteroaryl group
- n11 and n13 each independently represent an integer of 0 to 4
- X 12 and X 14 each independently represent an oxygen atom, a sulfur atom or a nitrogen atom
- m 12 represents 1
- X 12 is a nitrogen atom
- m 12 represents 2
- the substituents R 11 and R 13 represent, include the groups listed below substituents T, an alkyl group, an aryl group, a halogen atom, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, Heteroaryloxycarbonyl Preferred examples are groups, amido groups, cyano groups, nitro groups, trifluoromethyl groups, sulfoxide groups, sulfo groups and the like.
- R 12 and R 14 each independently represent a hydrogen atom, an alkyl group, an aryl group or a heteroaryl group.
- the carbon number of the alkyl group represented by R 12 and R 14 is preferably 1 to 20, more preferably 1 to 15, and still more preferably 1 to 8.
- the alkyl group may be linear, branched or cyclic, and is preferably linear or branched.
- the alkyl group may have a substituent. As a substituent, the group mentioned by the substituent T mentioned later is mentioned.
- the number of carbon atoms of the aryl group R 12 and R 14 represent is preferably 6 to 30, more preferably 6 to 20, more preferably 6 to 12.
- the aryl group may have a substituent.
- the heteroaryl group represented by R 12 and R 14 may be a single ring or a fused ring.
- the number of heteroatoms constituting the ring of the heteroaryl group is preferably 1 to 3.
- the heteroatom constituting the ring of the heteroaryl group is preferably a nitrogen atom, an oxygen atom or a sulfur atom.
- the heteroaryl group is preferably a 5- or 6-membered ring.
- the number of carbon atoms constituting the ring of the heteroaryl group is preferably 3 to 30, more preferably 3 to 18, and still more preferably 3 to 12.
- the heteroaryl group may have a substituent.
- the group mentioned by the substituent T mentioned later is mentioned.
- n11 and n13 each independently represent an integer of 0 to 4, preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and still more preferably 0 or 1. Is particularly preferred.
- Each of X 12 and X 14 independently represents an oxygen atom, a sulfur atom or a nitrogen atom. It is preferable that X 12 and X 14 each independently be an oxygen atom or a nitrogen atom, since it is possible to further increase the molar absorption coefficient of the pigment A at a wavelength of 500 to 600 nm, and an oxygen atom is particularly preferable.
- R 12 and R 14 are preferably a hydrogen atom or an alkyl group, and more preferably an alkyl group, because the molar absorption coefficient of the pigment A at a wavelength of 500 to 600 nm can be further increased.
- an alkyl group preferably an alkyl group having 1 to 30 carbon atoms
- an alkenyl group preferably an alkenyl group having 2 to 30 carbon atoms
- an alkynyl group preferably an alkynyl group having 2 to 30 carbon atoms
- an aryl group preferably An aryl group having 6 to 30 carbon atoms, an amino group (preferably an amino group having 0 to 30 carbon atoms), an alkoxy group (preferably an alkoxy group having 1 to 30 carbon atoms), an aryloxy group (preferably 6 to carbon atoms 30) aryloxy group), heteroaryloxy group
- acyl group preferably having 1 to 30 carbon atoms
- alkoxycarbonyl group preferably having 2 to 30 carbon atoms
- aryloxycarbonyl group preferably having 2 to 30 carbon atoms
- pigment A examples include compounds having the following structure.
- the designation of the substituent is "-"
- DPP-1 is a compound in which Z 1 and Z 3 to Z 10 are hydrogen atoms, and Z 2 is -OCH 3 .
- Me represents a methyl group
- Ph represents a phenyl group.
- the content of the pigment A is 40% by mass or more, preferably 45% by mass or more, and more preferably 50% by mass or more in the total solid content of the coloring composition.
- the upper limit can be 80% by mass or less.
- the proportion of the pigment A in the total mass of the compound having a diketopyrrolopyrrole skeleton contained in the coloring composition is preferably 80% by mass or more, more preferably 90% by mass or more, and 95% by mass % Or more is more preferable, and substantially only the pigment A is particularly preferable.
- the pigment A in the total mass of the compound having a diketopyrrolopyrrole skeleton contained in the coloring composition is used. Of 99% by mass or more is preferable, 99.5% by mass or more is preferable, 99.9% by mass or more is more preferable, and it is particularly preferable that the pigment A is composed of only preferable.
- the proportion of the pigment A in the total mass of the colorant contained in the coloring composition is preferably 60% by mass or more, more preferably 70% by mass or more, and 80% by mass or more. More preferable.
- the upper limit can be 90% by mass or less.
- the coloring composition of the present invention can contain a colorant other than the pigment A described above (hereinafter, also referred to as another colorant).
- Other colorants may be pigments or dyes.
- the pigment and the dye may be used in combination.
- the colorant used in the present invention preferably contains a pigment.
- the content of the pigment in the colorant is preferably 50% by mass or more, more preferably 70% by mass or more, still more preferably 80% by mass or more, and 90% by mass or more. Is particularly preferred.
- the colorant may be only a pigment.
- Examples of the pigment include inorganic pigments and organic pigments, and organic pigments are preferable.
- Examples of the organic pigment include those shown below.
- Red pigment C. I. Pigment green 7, 10, 36, 37, 58, 59 (above, green pigment), C. I. Pigment violet 1,19,23,27,32,37,42 etc (above, purple pigment), C. I. Pigment blue 1, 2, 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 22, 60, 64, 66, 79, 80 (the above, blue pigment).
- a green pigment a halogenated zinc phthalocyanine pigment having an average of 10 to 14 halogen atoms in one molecule, an average of 8 to 12 bromine atoms and an average of 2 to 5 chlorine atoms is used. It can also be done. Specific examples include the compounds described in International Publication WO 2015/118720. Moreover, the aluminum phthalocyanine compound which has a phosphorus atom can also be used as a blue pigment. Specific examples thereof include the compounds described in paragraphs 0022 to 0030 of JP-A-2012-247591 and paragraph 0047 of JP-A-2011-157478.
- the dye is not particularly limited, and known dyes can be used.
- the chemical structure includes pyrazole azo, anilinoazo, triarylmethane, anthraquinone, anthrapyridone, benzylidene, oxonol, pyrazolotriazole azo, pyridone azo, cyanine, phenothiazine, pyrrolopyrazole azomethine, Dyes such as xanthene dyes, phthalocyanine dyes, benzopyran dyes, indigo dyes, and pyromethene dyes can be used.
- a thiazole compound described in JP-A-2012-158649, an azo compound described in JP-A-2011-184493, and an azo compound described in JP-A-2011-145540 can also be preferably used.
- a yellow dye a quinophthalone compound described in paragraph 0011 to 0034 of JP-A-2013-54339, a quinophthalone compound described in paragraph 0013 to 0058 of JP-A 2014-26228, or the like can be used.
- dye multimer can also be used as another coloring agent.
- the dye multimer is preferably a dye used by being dissolved in a solvent, but the dye multimer may form particles, and when the dye multimer is particles, it is usually dispersed in a solvent. Used.
- the dye multimer in a particulate state can be obtained, for example, by emulsion polymerization, and the compounds and production methods described in JP-A-2015-214682 can be mentioned as specific examples.
- the dye multimer has two or more dye structures in one molecule, and preferably three or more dye structures. The upper limit is not particularly limited, but may be 100 or less. Plural dye structures in one molecule may be the same dye structure or different dye structures.
- the weight average molecular weight (Mw) of the dye multimer is preferably 2,000 to 50,000.
- the lower limit is more preferably 3000 or more, and still more preferably 6000 or more.
- the upper limit is more preferably 30000 or less, further preferably 20000 or less.
- compounds described in JP-A-2011-213925, JP-A-2013-041097, JP-A-2015-028144, JP-A-2015-030742 and the like can also be used.
- the other colorant is preferably a yellow colorant from the viewpoint of color reproducibility, more preferably a yellow pigment, and C.I. I. Pigment yellow 139, C.I. I. Pigment yellow 150 and C.I. I. Pigment yellow 185 or more preferably one or more selected from C.I. I. Pigment yellow 139 and C.I. I. Pigment yellow 185 or more preferably one or more selected from C.I. I. Pigment Yellow 139 is particularly preferable.
- a yellow pigment is used as another colorant, the effect of further improving the dispersibility of the pigment A can be obtained.
- content of another coloring agent is 40 mass parts or less with respect to 100 mass parts of the pigment A.
- the lower limit can be 1 part by mass or more, and can be 5 parts by mass or more.
- the upper limit is preferably 30 parts by mass or less, and more preferably 20 parts by mass or less.
- the content of the yellow colorant is preferably 40 parts by mass or less with respect to 100 parts by mass of the pigment A.
- the lower limit can be 1 part by mass or more, and can be 5 parts by mass or more.
- the upper limit is preferably 30 parts by mass or less, and more preferably 20 parts by mass or less.
- the total content of the pigment A and the other coloring agent is preferably 50 to 90% by mass in the total solid content of the coloring composition.
- the lower limit is preferably 51% by mass or more, and more preferably 55% by mass or more.
- the upper limit is preferably 85% by mass or less and more preferably 80% by mass or less.
- the total content of the pigment A and the yellow colorant is preferably 50 to 90% by mass in the total solid content of the coloring composition.
- the lower limit is preferably 51% by mass or more, and more preferably 55% by mass or more.
- the upper limit is preferably 85% by mass or less and more preferably 80% by mass or less.
- the coloring composition of the present invention contains a compound having a curable group.
- the reaction mechanism when the compound having a curable group cures is not particularly limited. Radical polymerization reaction, cationic polymerization reaction, condensation polymerization reaction, nucleophilic addition reaction, crosslinking reaction by substitution reaction, etc. may be mentioned.
- the compound having a curable group is preferably a compound which is cured by radical polymerization reaction. As a hardenable group, an ethylenically unsaturated group, an epoxy group, etc. are mentioned.
- Examples of the ethylenically unsaturated group include vinyl group, vinyloxy group, allyl group, methallyl group, (meth) acryloyl group, styrene group, cinnamoyl group and maleimide group, and (meth) acryloyl group, styrene group and maleimide group are mentioned.
- a (meth) acryloyl group is more preferable, and an acryloyl group is particularly preferable.
- the compound having a curable group may be a monomer or a resin such as a polymer.
- a curable compound of monomer type and a curable compound of resin type can also be used in combination.
- the compound having an ethylenically unsaturated group used as a curable compound may be a monomer (a monomer having an ethylenically unsaturated group), and a resin (ethylene) Resin having a unsaturated unsaturated group).
- a compound having an ethylenically unsaturated group is also referred to as a polymerizable compound.
- a monomer having an ethylenically unsaturated group is also referred to as a polymerizable monomer.
- a resin having an ethylenically unsaturated group is also referred to as a polymerizable resin.
- the molecular weight of the polymerizable monomer is preferably less than 3000.
- the upper limit is more preferably 2000 or less, still more preferably 1500 or less.
- the lower limit is preferably 100 or more, more preferably 150 or more, and still more preferably 250 or more.
- the polymerizable monomer is preferably a compound containing 3 or more ethylenically unsaturated groups, more preferably a compound containing 3 to 15 ethylenically unsaturated groups, and 3 to 6 ethylenically unsaturated groups. More preferably, it is a compound containing one.
- the polymerizable monomer is preferably a 3 to 15 functional (meth) acrylate compound, and more preferably a 3 to 6 functional (meth) acrylate compound.
- Specific examples of the polymerizable monomer are described in paragraph Nos. 0095 to 0108 of JP2009-288705A, paragraph 0227 of JP2013-29760A, and paragraph 0254-0257 of JP2008-292970A. Compounds are included, the contents of which are incorporated herein.
- the polymerizable monomer is dipentaerythritol triacrylate (commercially available as KAYARAD D-330; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetraacrylate (commercially available as KAYARAD D-320; Nippon Kayaku Co., Ltd.) Made, Dipentaerythritol penta (meth) acrylate (Commercial product: KAYARAD D-310; Nippon Kayaku Co., Ltd.), Dipentaerythritol hexa (meth) acrylate (Commercial product: KAYARAD DPHA; Nippon Kayaku ( Ltd.
- NK ester A-DPH-12E Shin-Nakamura Chemical Co., Ltd. product
- the compound of the structure where these (meth) acryloyl groups are linked via ethylene glycol and / or propylene glycol residue is preferable.
- NK ester A-TMMT manufactured by Shin-Nakamura Chemical Co., Ltd.
- KAYARAD RP-1040 KAYARAD RP-1040
- DPCA-20 manufactured by Nippon Kayaku Co., Ltd.
- trimethylolpropane tri (meth) acrylate trimethylolpropane propyleneoxy modified tri (meth) acrylate, trimethylolpropane ethyleneoxy modified tri (meth) acrylate, isocyanuric acid ethyleneoxy modified tri (meth) acrylate
- a trifunctional (meth) acrylate compound such as pentaerythritol tri (meth) acrylate.
- Commercially available products of trifunctional (meth) acrylate compounds include Alonics M-309, M-310, M-321, M-350, M-360, M-313, M-315, M-306, and M-305.
- M-303, M-452, M-450 (manufactured by Toagosei Co., Ltd.), NK ester A9300, A-GLY-9E, A-GLY-20E, A-TMM-3, A-TMM-3L, A -TMM-3LM-N, A-TMPT, TMPT (manufactured by Shin-Nakamura Chemical Co., Ltd.), KAYARAD GPO-303, TMPTA, THE-330, TPA-330, PET-30 (manufactured by Nippon Kayaku Co., Ltd.) Etc.
- the polymerizable monomer may have an acid group.
- an acid group a carboxyl group, a sulfo group, a phosphoric acid group etc. are mentioned, A carboxyl group is preferable.
- Commercially available products of the polymerizable monomer having an acid group include ALONIX M-510, M-520, ALONIX TO-2349 (manufactured by Toagosei Co., Ltd.), and the like.
- the acid value of the polymerizable monomer having an acid group is preferably 0.1 to 40 mg KOH / g, and more preferably 5 to 30 mg KOH / g.
- the acid value of the polymerizable monomer is 0.1 mg KOH / g or more, the solubility in a developer is good, and more excellent developability can be obtained.
- the acid value of the polymerizable monomer is 40 mg KOH / g or less, it is advantageous in terms of production and handling.
- a compound having a caprolactone structure is also a preferable embodiment.
- examples of the polymerizable compound having a caprolactone structure are commercially available from Nippon Kayaku Co., Ltd. as KAYARAD DPCA series, and include DPCA-20, DPCA-30, DPCA-60, DPCA-120 and the like.
- the polymerizable monomer a compound having an alkyleneoxy group can also be used.
- the polymerizable monomer having an alkyleneoxy group is preferably a compound having an ethyleneoxy group and / or a propyleneoxy group, more preferably a compound having an ethyleneoxy group, and having 4 to 20 ethyleneoxy groups. More preferably, it is a 3- to 6-functional (meth) acrylate compound.
- SR-494 which is a tetrafunctional (meth) acrylate having four ethyleneoxy groups manufactured by Sartomer, a trifunctional (meth) having three isobutylene oxy groups
- examples thereof include KAYARAD TPA-330 which is an acrylate.
- urethane acrylates as described in JP-B-48-41708, JP-A-51-37193, JP-B-2-32293 and JP-B-2-16765
- the urethane compounds having an ethylene oxide skeleton described in JP-B-58-49860, JP-B-56-17654, JP-B-62-39417 and JP-B-62-39418 are also suitable.
- UA-7200 Shin-Nakamura Chemical Co., Ltd. product
- DPHA-40H Nippon Kayaku Co., Ltd. product
- UA-306H, UA-306T, UA-306I, AH-600, T- 600, AI-600 manufactured by Kyoeisha Chemical Co., Ltd.
- the polymerizable monomer it is also preferable to use 8UH-1006, 8UH-1012 (all manufactured by Taisei Fine Chemical Co., Ltd.), light acrylate POB-A0 (manufactured by Kyoeisha Chemical Co., Ltd.), and the like.
- compounds described in JP-A-2017-48367, JP-A-6057891, and JP-A-6031807 can also be used.
- the weight average molecular weight of the polymerizable resin is preferably 3,000 or more, more preferably 5,000 or more, still more preferably 7,000 or more, and particularly preferably 10,000 or more.
- the weight average molecular weight of the synthetic resin is preferably 50,000 or less, more preferably 40,000 or less, and still more preferably 30,000 or less.
- the upper limit is more preferably 4.0 mmol / g or less, and still more preferably 3.0 mmol / g or less.
- the lower limit is more preferably 0.3 mmol / g or more.
- the polymerizable resin preferably contains a repeating unit having an ethylenically unsaturated group in a side chain, and more preferably contains a repeating unit represented by the following formula (A-1-1).
- the repeating unit having an ethylenically unsaturated group is preferably contained in an amount of 10 mol% or more, and more preferably 10 to 80 mol%, in all repeating units of the polymerizable resin. It is more preferable to contain 70 mol%.
- X 1 represents a main chain of a repeating unit
- L 1 represents a single bond or a divalent linking group
- Y 1 represents an ethylenically unsaturated group.
- an alkylene group preferably an alkylene group having 1 to 12 carbon atoms
- an alkyleneoxy group preferably an alkylene having 1 to 12 carbon atoms
- Oxy group oxyalkylene carbonyl group
- arylene group preferably arylene group having 6 to 20 carbon atoms
- examples of the ethylenically unsaturated group represented by Y 1 include vinyl group, vinyloxy group, allyl group, methallyl group, (meth) acryloyl group, styrene group, cinnamoyl group and maleimide group.
- (Meth) acryloyl group, styrene group and maleimide group are preferable, (meth) acryloyl group is more preferable, and acryloyl group is particularly preferable.
- the polymerizable resin preferably further contains a repeating unit having a graft chain.
- the polymerizable resin preferably contains a repeating unit having a graft chain in an amount of 1.0 to 60 mol%, and more preferably 1.5 to 50 mol%, based on all repeating units of the polymerizable resin.
- a polymerizable resin containing a repeating unit having a graft chain is preferably used as a dispersant.
- a graft chain means a polymer chain which branches and extends from the main chain of a repeating unit.
- the length of the graft chain is not particularly limited, but the longer the graft chain, the higher the steric repulsion effect, and the dispersibility of the pigment A and the like can be enhanced.
- the graft chain preferably has 40 to 10,000 atoms excluding hydrogen atoms, more preferably 50 to 2,000 atoms excluding hydrogen atoms, and 60 to 60 atoms excluding hydrogen atoms. More preferably, it is 500.
- the graft chain possessed by the polymerizable resin preferably includes at least one structure selected from polyester structure, polyether structure, poly (meth) acrylic structure, polyurethane structure, polyurea structure and polyamide structure, and polyester structure, polyether It is more preferable to include at least one structure selected from a structure and a poly (meth) acrylic structure, and it is further preferable to include a polyester structure.
- the polyester structure include structures represented by the following Formula (G-1), Formula (G-4) or Formula (G-5).
- the polyether structure a structure represented by the following formula (G-2) can be mentioned.
- examples of the poly (meth) acrylic structure include a structure represented by the following formula (G-3).
- R G1 and R G2 each represent an alkylene group.
- the alkylene group represented by R G1 and R G2 is not particularly limited, but a linear or branched alkylene group having 1 to 20 carbon atoms is preferable, and a linear or branched alkylene having 2 to 16 carbon atoms is preferable. A group is more preferable, and a linear or branched alkylene group having 3 to 12 carbon atoms is further preferable.
- R G3 represents a hydrogen atom or a methyl group.
- Q G1 represents -O- or -NH-
- L G1 represents a single bond or a divalent linking group.
- Examples of the divalent linking group include an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an alkyleneoxy group (preferably an alkyleneoxy group having 1 to 12 carbon atoms), and an oxyalkylene carbonyl group (preferably having 1 carbon atom).
- an alkylene group preferably an alkylene group having 1 to 12 carbon atoms
- an alkyleneoxy group preferably an alkyleneoxy group having 1 to 12 carbon atoms
- an oxyalkylene carbonyl group preferably having 1 carbon atom.
- arylene group preferably arylene group having 6 to 20 carbon atoms
- R G4 represents a hydrogen atom or a substituent.
- substituents examples include an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthioether group, an arylthioether group, a heteroarylthioether group and the like.
- the graft chain may contain only one type of polyester structure may include R G1 is different polyester structure of two or more.
- R G1 is different polyester structure of two or more.
- the graft chain may contain only one type of polyether structure, and R G2 may contain two or more different polyether structures.
- the graft chain contains a poly (meth) acrylic structure, it may contain only one poly (meth) acrylic structure, and at least one selected from R G3 , Q G1 , L G1 and R G4 is Two or more kinds of different poly (meth) acrylic structures may be included.
- the terminal structure of the graft chain is not particularly limited. It may be a hydrogen atom or a substituent.
- substituents include an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthioether group, an arylthioether group, a heteroarylthioether group and the like.
- a group having a steric repulsion effect is preferable, and an alkyl group having 5 to 24 carbon atoms or an alkoxy group is preferable, from the viewpoint of improving the dispersibility of the coloring material and the like.
- the alkyl group and the alkoxy group may be linear, branched or cyclic, and linear or branched is preferable.
- a structure represented by the following formula (G-1a), formula (G-2a), formula (G-3a), formula (G-4a) or formula (G-5a) Is preferred.
- R G1 and R G2 each represent an alkylene group
- R G3 represents a hydrogen atom or a methyl group
- Q G1 represents -O- or -NH-
- L G1 represents a single bond
- R G4 represents a hydrogen atom or a substituent
- W 100 represents a hydrogen atom or a substituent.
- n1 to n5 each independently represent an integer of 2 or more.
- Q G1 , L G1 , Formula (G1) ⁇ (G-5 ) has the same meaning as R G1 ⁇ R G4, Q G1 , L G1 described in, the preferred range is also the same is there.
- W 100 is preferably a substituent.
- the substituent include an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthioether group, an arylthioether group, a heteroarylthioether group and the like.
- a group having a steric repulsion effect is preferable, and an alkyl group having 5 to 24 carbon atoms or an alkoxy group is preferable, from the viewpoint of improving the dispersibility of the coloring material and the like.
- the alkyl group and the alkoxy group may be linear, branched or cyclic, and linear or branched is preferable.
- n1 to n5 each independently represent an integer of 2 or more, more preferably 3 or more, and still more preferably 5 or more.
- the upper limit is preferably 100 or less, more preferably 80 or less, and still more preferably 60 or less.
- R G1 's in the respective repeating units may be the same or different.
- the arrangement of each repeating unit is not particularly limited, and may be random, alternating, or block. The same applies to formulas (G-2a) to (G-5a).
- repeating unit having a graft chain examples include repeating units represented by the following formula (A-1-2).
- Examples of the main chain of the repeating unit represented by X 2 in Formula (A-1-2) include the structures described in X 1 of Formula (A-1-1), and preferred ranges are also the same.
- the divalent linking group represented by L 2 in Formula (A-1-2) includes an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms) and an arylene group (preferably an arylene group having 6 to 20 carbon atoms) And -NH-, -SO-, -SO 2- , -CO-, -O-, -COO-, OCO-, -S- and a group formed by combining two or more of these.
- Examples of the graft chain represented by W 1 in formula (A-1-2) include the graft chains described above.
- the weight average molecular weight (Mw) of the repeating unit having a graft chain is preferably 1000 or more, more preferably 1000 to 10000, and 1000 to 7500. It is further preferred that In the present invention, the weight average molecular weight of the repeating unit having a graft chain is a value calculated from the weight average molecular weight of the raw material monomer used for the polymerization of the same repeating unit.
- a repeating unit having a graft chain can be formed by polymerizing a macromonomer.
- the macromonomer means a polymer compound in which a polymerizable group is introduced at the polymer end.
- the polymerizable resin further contains a repeating unit having an acid group.
- the dispersibility of the pigment A and the like can be further improved.
- developability can also be improved.
- the acid group include a carboxyl group, a sulfo group and a phosphate group.
- repeating unit having an acid group examples include repeating units represented by the following formula (A-1-3).
- the divalent linking group represented by L 3 in Formula (A-1-3) includes an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms) and an alkenylene group (preferably an alkenylene group having 2 to 12 carbon atoms) , An alkyleneoxy group (preferably an alkyleneoxy group having 1 to 12 carbon atoms), an oxyalkylene carbonyl group (preferably an oxyalkylene carbonyl group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms) And —NH—, —SO—, —SO 2 —, —CO—, —O—, —COO—, OCO—, —S— and groups in which two or more of these are combined.
- the alkylene group, the alkylene group in the alkyleneoxy group, and the alkylene group in the oxyalkylene carbonyl group may be linear, branched or cyclic, and is preferably linear or branched. Further, the alkylene group, the alkylene group in the alkyleneoxy group, and the alkylene group in the oxyalkylene carbonyl group may have a substituent or may be unsubstituted. As a substituent, a hydroxyl group etc. are mentioned.
- Examples of the acid group represented by A 1 in formula (A-1-3) include a carboxyl group, a sulfo group and a phosphoric acid group.
- the acid value of the polymerizable resin is preferably 20 to 150 mg KOH / g.
- the upper limit is more preferably 100 mg KOH / g or less.
- the lower limit is preferably 30 mg KOH / g or more, and more preferably 35 mg KOH / g or more. If the acid value of the polymerizable resin is in the above range, particularly excellent dispersibility is easily obtained. Furthermore, excellent developability is easily obtained.
- the polymerizable resin may also be referred to as a compound represented by the following formula (ED1) and / or a compound represented by the following formula (ED2) as the other repeating unit (hereinafter, these compounds are referred to as "ether dimer” And B.) can be included.
- ED1 a compound represented by the following formula
- ED2 a compound represented by the following formula
- 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.
- R represents a hydrogen atom or an organic group having 1 to 30 carbon atoms.
- the description in JP-A-2010-168539 can be referred to.
- ether dimer for example, paragraph “0317” of JP-A-2013-29760 can be referred to, and the contents thereof are incorporated in the present specification.
- the ether dimer may be only one type, or two or more types.
- a compound having two or more epoxy groups in one molecule is preferably used as a compound having an epoxy group (hereinafter, also referred to as an epoxy compound) used as a curable compound.
- the upper limit of the epoxy group of the epoxy compound is preferably 100 or less, more preferably 10 or less, and still more preferably 5 or less.
- the epoxy compound may be a low molecular weight compound (for example, a molecular weight of less than 1000) or a macromolecular compound (for example, a molecular weight of 1000 or more, and in the case of a polymer, a weight average molecular weight of 1000 or more).
- the molecular weight (weight average molecular weight in the case of a polymer) of the epoxy compound is preferably 200 to 100,000, and more preferably 500 to 50,000. 3000 or less is preferable, as for the upper limit of molecular weight (in the case of a polymer, weight average molecular weight), 2000 or less is more preferable, and 1500 or less is still more preferable.
- the epoxy compounds are compounds described in paragraphs 0034 to 0036 in JP 2013-011869A, paragraphs 0147 to 0156 in JP 2014-043556 A, and paragraphs 0085 to 0092 in JP 2014-089408 A. Can also be used. The contents of these are incorporated herein.
- the epoxy compound for example, as bisphenol A type epoxy resin, jER825, jER827, jER828, jER834, jER1001, jER1002, jER1003, jER1055, jER1007, jER1009, jER1010 (all manufactured by Mitsubishi Chemical Corporation), EPICLON 860, EPICLON 1050, EPICLON 1051, EPICLON 1055 (all manufactured by DIC Corporation) and the like, and as a bisphenol F-type epoxy resin, jER806, jER807, jER4004, jER4005, jER4007, jER4010 (all manufactured by Mitsubishi Chemical Corporation), EPICLON 830, EPICLON 835 (above, DIC Corporation), LCE-21, RE-602S (above, Japan Drugs, etc., and as phenol novolac type epoxy resins, jER152, jER154, jER157S70, jER157S65 (abo
- EPICLON N-695 (all, DIC Corporation), EOCN-1020 (Nippon Kayaku Co., Ltd.), etc.
- ADEKA RESIN EP-4080S As aliphatic epoxy resins, ADEKA RESIN EP-4080S, EP 4085S, EP-4088S (above, made by ADEKA Co., Ltd.), Celoxide 2021 P, Celoxide 2081, Celoxide 2083, Celoxide 2085, EHPE 3150, EPOLEAD PB 3600, same PB 4700 (above, made by Daicel), Denacol EX- 212L, EX-214L, EX-216L, EX-321L, EX-850L (all manufactured by Nagase ChemteX Co., Ltd.) and the like.
- ADEKA RESIN EP-4000S, EP-4003S, EP-4010S, EP-4011S (above, made by ADEKA), NC-2000, NC-3000, NC-7300, XD-1000, EPPN-501, EPPN-502 (all manufactured by ADEKA Co., Ltd.), jER1031S (manufactured by Mitsubishi Chemical Corporation), and the like can be mentioned.
- the content of the curable compound is preferably 5 to 50% by mass in the total solid content of the coloring composition.
- the lower limit is preferably 8% by mass or more, and more preferably 10% by mass or more.
- the upper limit is preferably 45% by mass or less, and more preferably 40% by mass or less.
- the content of the polymerizable compound is preferably 5 to 50% by mass in the total solid content of the coloring composition.
- the lower limit is preferably 8% by mass or more, and more preferably 10% by mass or more.
- the upper limit is preferably 45% by mass or less, and more preferably 40% by mass or less.
- the content of the polymerizable monomer is preferably 0.1 to 40% by mass in the total solid content of the coloring composition.
- the lower limit is preferably 1% by mass or more, and more preferably 2% by mass or more.
- the upper limit is preferably 30% by mass or less, and more preferably 20% by mass or less.
- the content of the polymerizable resin is preferably 5 to 50% by mass in the total solid content of the coloring composition.
- the lower limit is preferably 8% by mass or more, and more preferably 10% by mass or more.
- the upper limit is preferably 45% by mass or less, and more preferably 40% by mass or less.
- the content of the polymerizable resin in the total amount of the polymerizable monomer and the polymerizable resin is preferably 70% by mass or more, and more preferably 80% by mass or more.
- the content of the epoxy compound is preferably 0.1 to 40% by mass in the total solid content of the coloring composition.
- the lower limit is, for example, preferably 1% by mass or more, and more preferably 2% by mass or more.
- the upper limit is, for example, more preferably 30% by mass or less, and still more preferably 20% by mass or less.
- the epoxy compounds may be used alone or in combination of two or more.
- the ratio (mass ratio) of both is preferably such that the mass of the polymerizable compound: the mass of the compound having an epoxy group is 100: 1 to 100: 400. 100: 1 to 100: 100 is more preferable, and 100: 1 to 100: 50 is further preferable.
- the coloring composition comprises a monomer having an ethylenically unsaturated group, and a resin, M1 / B1 which is a ratio of the mass M1 of the monomer having an ethylenically unsaturated group contained in the coloring composition to the mass B1 of the resin contained in the coloring composition is 0.3 or less, preferably 0.2
- M1 / B1 which is a ratio of the mass M1 of the monomer having an ethylenically unsaturated group contained in the coloring composition to the mass B1 of the resin contained in the coloring composition is 0.3 or less, preferably 0.2
- mass B1 of resin is the total amount of polymeric resin mentioned above and other resin mentioned later.
- the coloring composition does not contain another resin
- the mass B1 of the resin is the mass of the above-described polymerizable resin.
- mass B1 of resin is mass of other resin.
- the coloring composition of this invention contains an epoxy compound as a curable compound. According to the coloring composition of this aspect, it can be preferably used as a coloring composition for dry etching.
- the coloring composition of the present invention can further contain a resin containing no curable group (hereinafter, also referred to as another resin).
- a resin containing no curable group hereinafter, also referred to as another resin.
- Other resins are blended, for example, in applications in which particles such as pigments are dispersed in a composition and applications in binders.
- grains, such as a pigment is also called a dispersing agent.
- such application of the resin is an example, and the resin can also be used for purposes other than such application.
- the weight average molecular weight (Mw) of the other resin is preferably 2,000 to 2,000,000.
- the upper limit is preferably 1,000,000 or less, and more preferably 500000 or less. 3000 or more are preferable and, as for a lower limit, 5000 or more are more preferable.
- (meth) acrylic resin, ene thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyether sulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, polyimide resin, polyamide Imide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, etc. may be mentioned.
- One of these resins may be used alone, or two or more thereof may be mixed and used.
- resins may have an acid group.
- an acid group a carboxyl group, a phosphoric acid group, a sulfo group, a phenolic hydroxyl group etc. are mentioned, for example, A carboxyl group is preferable.
- These acid groups may be of only one type, or of two or more types.
- the resin having an acid group can also be used as an alkali-soluble resin.
- a polymer having a carboxyl group in a side chain is preferable.
- alkali-soluble polymers such as methacrylic acid copolymer, acrylic acid copolymer, itaconic acid copolymer, crotonic acid copolymer, maleic acid copolymer, partially esterified maleic acid copolymer, novolac resin, etc.
- a phenol resin, an acidic cellulose derivative having a carboxyl group in a side chain, and a resin obtained by adding an acid anhydride to a polymer having a hydroxyl group are mentioned.
- copolymers of (meth) acrylic acid and other monomers copolymerizable therewith are suitable as the alkali-soluble resin.
- Other monomers copolymerizable with (meth) acrylic acid include alkyl (meth) acrylates, aryl (meth) acrylates, vinyl compounds and the like.
- 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, Hexyl (meth) acrylate, octyl (meth) acrylate, phenyl (meth) acrylate, benzyl (meth) acrylate, tolyl (meth) acrylate, naphthyl (meth) acrylate, cyclohexyl (meth) acrylate, glycidyl (meth) acrylate, etc.
- vinyl compound examples include styrene, ⁇ -methylstyrene, vinyl toluene, acrylonitrile, vinyl acetate, N-vinyl pyrrolidone, polystyrene macromonomer, polymethyl methacrylate macromonomer and the like.
- N-substituted maleimide monomers described in JP-A-10-300922 such as N-phenyl maleimide, N-cyclohexyl maleimide and the like can also be used.
- These other monomers copolymerizable with (meth) acrylic acid may be only one type, or two or more types.
- Resin having an acid group is benzyl (meth) acrylate / (meth) acrylic acid copolymer, benzyl (meth) acrylate / (meth) acrylic acid / 2-hydroxyethyl (meth) acrylate copolymer, benzyl (meth)
- a multicomponent copolymer consisting of acrylate / (meth) acrylic acid / other monomers can be preferably used. Further, those obtained by copolymerizing 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate / polystyrene macromonomer / benzyl methacrylate / methacrylic acid copolymer described in JP-A No.
- the resin having an acid group is a polymer containing a repeating unit derived from a monomer component including the above-mentioned ether dimer.
- the resin having an acid group may contain a repeating unit derived from a compound represented by the following formula (X).
- R 1 represents a hydrogen atom or a methyl group
- R 2 represents an alkylene group having 2 to 10 carbon atoms
- R 3 has a hydrogen atom or 1 to 20 carbon atoms which may contain a benzene ring.
- Represents an alkyl group of n represents an integer of 1 to 15.
- the resin having an acid group is described in JP-A-2012-208494, paragraphs 0558 to 0571 (corresponding US patent application publication No. 2012/0235099, paragraphs 0685 to 0700), JP-A-2012-198408. No. 0076-0099 can be referred to, and the contents thereof are incorporated herein. Moreover, the resin which has an acidic radical can also use a commercial item.
- the acid value of the resin having an acid group is preferably 30 to 200 mg KOH / g.
- the lower limit is preferably 50 mg KOH / g or more, and more preferably 70 mg KOH / g or more.
- 150 mgKOH / g or less is preferable and 120 mgKOH / g or less of an upper limit is more preferable.
- resin which has an acidic radical resin of the following structure etc. are mentioned, for example.
- the coloring composition of the present invention can also contain a resin as a dispersant.
- the dispersant includes an acidic dispersant (acidic resin) and a basic dispersant (basic resin).
- the acidic dispersant (acidic resin) represents a resin in which the amount of acid groups is larger than the amount of basic groups.
- the acidic dispersant (acidic resin) is preferably a resin in which the amount of acid groups accounts for 70 mol% or more when the total amount of the amount of acid groups and the amount of basic groups is 100 mol%. Resins consisting only of groups are more preferred.
- the acid group of the acidic dispersant (acidic resin) is preferably a carboxyl group.
- the acid value of the acidic dispersant is preferably 40 to 105 mg KOH / g, more preferably 50 to 105 mg KOH / g, and still more preferably 60 to 105 mg KOH / g.
- a basic dispersing agent represents resin whose quantity of a basic group is larger than the quantity of an acidic radical.
- the basic dispersant is preferably a resin in which the amount of basic groups exceeds 50% by mole, where the total amount of the amount of acid groups and the amount of basic groups is 100% by mole.
- the basic group possessed by the basic dispersant is preferably an amino group.
- the resin used as the dispersant preferably contains a repeating unit having an acid group.
- the resin used as the dispersing agent contains a repeating unit having an acid group, it is possible to further reduce the residue generated on the base of the pixel when forming a pattern by photolithography.
- a resin used as a dispersant it is preferable to use a graft resin having a poly (meth) acrylate structure as a main chain and containing a repeating unit A having a graft chain of a polyester structure in a side chain (hereinafter also referred to as graft resin A).
- graft resin A a graft resin having a poly (meth) acrylate structure as a main chain and containing a repeating unit A having a graft chain of a polyester structure in a side chain
- the repeating number of the polyester in the graft chain is preferably 3 or more, more preferably 4 or more, and still more preferably 5 or more from the viewpoint of pigment dispersibility.
- the terminal structure of the graft chain is not particularly limited. It may be a hydrogen atom or a substituent.
- substituent include an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthioether group, an arylthioether group, a heteroarylthioether group and the like.
- a group having a steric repulsion effect is preferable, and an alkyl group having 5 to 24 carbon atoms or an alkoxy group is preferable.
- the alkyl group and the alkoxy group may be linear, branched or cyclic, and linear or branched is preferable.
- the repeating unit A in the graft resin A is preferably a repeating unit represented by the following formula (GA).
- R A1 represents a hydrogen atom or an alkyl group
- L A1 represents a single bond or a divalent linking group
- W A1 represents a graft chain of a polyester structure.
- the carbon number of the alkyl group represented by R A1 is preferably 1 to 5, more preferably 1 to 3, and still more preferably 1.
- R A1 is preferably a hydrogen atom or a methyl group.
- Examples of the divalent linking group represented by L A1 include an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), -NH-, -SO-, And -SO 2- , -CO-, -O-, -COO-, OCO-, -S- and a group formed by combining two or more of these.
- the alkylene group may be linear, branched or cyclic, and is preferably linear or branched.
- W A1 represents a graft chain of polyester structure.
- the graft chain of the polyester structure is preferably a graft chain of the structure represented by the above-mentioned formula (G-1a), formula (G-4a) or formula (G-5a).
- the graft resin A preferably contains 20 mol% or more of the repeating unit A in all repeating units of the graft resin A.
- the upper limit may be 100 mol%, 90 mol% or less, 80 mol% or less, 70 mol% or less, or 60 mol% or less. it can.
- graft resin A Details of the graft resin A can be referred to the description of Paragraph Nos. 0025 to 0094 of JP-A-2012-255128, the contents of which are incorporated herein. Moreover, the following resin is mentioned as a specific example of graft resin A.
- an oligoimine dispersant containing a nitrogen atom in at least one of the main chain and the side chain as the resin used as the dispersant.
- the oligoimine dispersant comprises a structural unit having a partial structure X having a functional group having a pKa of 14 or less and a side chain containing a side chain Y having an atom number of 40 to 10,000, and having a main chain and a side chain
- the resin which has a basic nitrogen atom in at least one side is preferable.
- the basic nitrogen atom is not particularly limited as long as it is a nitrogen atom exhibiting basicity.
- oligoimine dispersant With regard to the oligoimine dispersant, the description in paragraphs [0102] to [0166] of JP 2012-255128 A can be referred to, and the contents thereof are incorporated herein. As the oligoimine dispersant, resins described in paragraph Nos. 0168 to 0174 of JP-A-2012-255128 can be used.
- Dispersants are also available as commercial products, and specific examples thereof include the Disperbyk series (eg, Disperbyk-111 etc.) manufactured by BYK Chemie, the Solsperse series manufactured by Nippon Lubrizol Corporation (eg, And so forth).
- pigment dispersants described in paragraphs 0041 to 0130 of JP-A-2014-130338 can also be used, the contents of which are incorporated herein.
- the resin etc. which have an acidic radical mentioned above can also be used as a dispersing agent.
- the content of the other resin is preferably 30% by mass or less and 20% by mass or less in the total solid content of the coloring composition of the present invention. Is more preferably 10% by mass or less.
- the coloring composition of the present invention can be substantially free of other resins.
- the content of the other resins in the total solid content of the coloring composition of the present invention is preferably 0.1% by mass or less It is more preferable that it is 0.05 mass% or less, and it is especially preferable not to contain.
- the total content of the above-mentioned curable compound and other resin is preferably 10 to 50% by mass in the total solid content of the colored composition of the present invention.
- the lower limit is preferably 12% by mass or more, and more preferably 14% by mass or more.
- the upper limit is preferably 45% by mass or less, and more preferably 40% by mass or less.
- the coloring composition of the present invention preferably further contains a photopolymerization initiator.
- a photoinitiator It can select suitably from well-known photoinitiators.
- compounds having photosensitivity to light in the ultraviolet to visible region are preferred.
- it may be a compound which produces an active radical by causing an action with a photoexcited sensitizer.
- a halogenated hydrocarbon derivative for example, a compound having a triazine skeleton, a compound having an oxadiazole skeleton, etc.
- an acylphosphine compound for example, a hexaarylbiimidazole, an oxime compound, an organic peroxide, Thio compounds, ketone compounds, aromatic onium salts, ⁇ -hydroxy ketone compounds, ⁇ -amino ketone compounds and the like
- an organic peroxide for example, a compound having a triazine skeleton, a compound having an oxadiazole skeleton, etc.
- an acylphosphine compound for example, a compound having a triazine skeleton, a compound having an oxadiazole skeleton, etc.
- an acylphosphine compound for example, a compound having a triazine skeleton, a compound having an oxadiazole skeleton, etc.
- the photopolymerization initiator is a trihalomethyl triazine compound, a benzyl dimethyl ketal compound, an ⁇ -hydroxy ketone compound, an ⁇ -amino ketone compound, an acyl phosphine compound, a phosphine oxide compound, a metallocene compound, an oxime compound, a triaryl imidazole from the viewpoint of exposure sensitivity.
- Dimers, onium compounds, benzothiazole compounds, benzophenone compounds, acetophenone compounds, cyclopentadiene-benzene-iron complexes, halomethyl oxadiazole compounds and 3-aryl substituted coumarin compounds are preferred, and oxime compounds, ⁇ -hydroxy ketone compounds, ⁇ -hydroxy ketone compounds More preferred are compounds selected from amino ketone compounds and acyl phosphine compounds, and more preferred are oxime compounds.
- the description of paragraph Nos. 0065 to 0111 of JP-A-2014-130173 and paragraph Nos. 0274 to 0306 of JP-A-2013-29760 can be referred to, and the contents thereof are incorporated in the present specification. .
- Examples of commercially available ⁇ -hydroxy ketone compounds include IRGACURE-184, DAROCUR-1173, IRGACURE-500, IRGACURE-2959, IRGACURE-127 (manufactured by BASF Corporation) and the like.
- Examples of commercially available ⁇ -amino ketone compounds include IRGACURE-907, IRGACURE-369, IRGACURE-379, and IRGACURE-379EG (manufactured by BASF Corporation).
- Examples of commercially available products of acyl phosphine compounds include IRGACURE-819, DAROCUR-TPO (all manufactured by BASF Corp.) and the like.
- Examples of the oxime compound include the compounds described in JP-A-2001-233842, the compounds described in JP-A-2000-80068, the compounds described in JP-A-2006-342166, and the like.
- C. S. Perkin II (1979, pp. 1653-1660) a compound described in J. Am. C. S. A compound described in Perkin II (1979, pp. 156-162), a compound described in Journal of Photopolymer Science and Technology (1995, pp.
- oxime compound examples include, for example, 3-benzoyloxyiminobutan-2-one, 3-acetoxyiminobutan-2-one, 3-propionyloxyiminobutan-2-one, 2-acetoxyiminopentane-3- On, 2-acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropan-1-one, 3- (4-toluenesulfonyloxy) iminobutan-2-one, and 2-ethoxy Examples include carbonyloxyimino-1-phenylpropan-1-one and the like.
- IRGACURE-OXE01, IRGACURE-OXE02, IRGACURE-OXE03 and IRGACURE-OXE04 are also suitably used.
- TRONLY TR-PBG-304, TRONLY TR-PBG-309, TRONLY TR-PBG-305 (made by CHANGZHOU TRONLY NEW ELECTRONIC MATERIALS CO., LTD.), Adeka ARKules NCI-930 And Adeka Optomer N-1919 (photopolymerization initiator 2 of JP 2012-14052 A) (all manufactured by ADEKA Co., Ltd.).
- an oxime compound having a fluorene ring can also be used as a photopolymerization initiator.
- the oxime compound having a fluorene ring compounds described in JP-A-2014-137466 can be mentioned. This content is incorporated herein.
- an oxime compound having a benzofuran skeleton can also be used as a photopolymerization initiator.
- Specific examples thereof include the compounds OE-01 to OE-75 described in International Publication WO 2015/036910.
- an oxime compound having a skeleton in which at least one benzene ring of a carbazole ring is a naphthalene ring can also be used as a photopolymerization initiator.
- an oxime compound having a skeleton in which at least one benzene ring of a carbazole ring is a naphthalene ring
- the compound described in International Publication WO 2013/083505 can be mentioned.
- an oxime compound having a fluorine atom can also be used as a photopolymerization initiator.
- Specific examples of the oxime compound having a fluorine atom include the compounds described in JP-A-2010-262028, the compounds 24 and 36 to 40 described in JP-A-2014-500852, and JP-A-2013-164471. And the like (C-3) and the like. This content is incorporated herein.
- an oxime compound having a nitro group can be used as a photopolymerization initiator.
- the oxime compound having a nitro group is also preferably a dimer.
- specific examples of the oxime compound having a nitro group compounds described in paragraphs 0031 to 0047 of JP 2013-114249 A, paragraphs 0008 to 0012 and 0070 to 0079 of JP 2014-137466 A, and patent 4223071 Compounds described in Paragraph Nos. 0007 to 0025 of the gazette, Adeka Arkles NCI-831 (manufactured by ADEKA Co., Ltd.), and the like.
- oxime compounds preferably used in the present invention are shown below, but the present invention is not limited thereto.
- the oxime compound is preferably a compound having a maximum absorption wavelength in the range of 350 to 500 nm, and more preferably a compound having a maximum absorption wavelength in the range of 360 to 480 nm. Moreover, the oxime compound is preferably a compound having a high absorbance at 365 nm and 405 nm.
- the molar absorption coefficient of the oxime compound at 365 nm or 405 nm is preferably 1,000 to 300,000, more preferably 2,000 to 300,000, and 5,000 to 200, Particularly preferred is 000.
- the molar extinction coefficient of a compound can be measured using a known method. For example, it is preferable to measure at a concentration of 0.01 g / L using an ethyl acetate solvent with a UV-visible spectrophotometer (Cary-5 spectrophotometer manufactured by Varian).
- a bifunctional or trifunctional or higher functional photopolymerization initiator may be used as the photopolymerization initiator.
- a photopolymerization initiator paragraph Nos. 0417 to 0412 of JP-A-2010-527339, JP-A-2011-524436, International Publication WO2015 / 004565, JP-A-2016-532675.
- the content of the photopolymerization initiator is preferably 0.1 to 30% by mass in the total solid content of the coloring composition.
- the lower limit is, for example, more preferably 0.5% by mass or more, and still more preferably 1% by mass or more.
- the upper limit is, for example, more preferably 20% by mass or less and still more preferably 10% by mass or less.
- the coloring composition may contain only one type of photopolymerization initiator, or may contain two or more types. When 2 or more types of photoinitiators are included, it is preferable that the total amount of them becomes said range.
- the coloring composition of the present invention preferably contains a solvent.
- the solvent is preferably an organic solvent.
- the solvent is not particularly limited as long as the solubility of each component and the coating property of the coloring composition are satisfied.
- organic solvent examples include, for example, the following organic solvents.
- esters for example, ethyl acetate, n-butyl acetate, isobutyl acetate, cyclohexyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl lactate, ethyl lactate, alkyl alkyl oxyacetate alkylate (Eg, methyl alkyl oxyacetate, ethyl alkyl oxyacetate, butyl alkyl oxyacetate (eg, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate etc.), alkyl 3-alkyloxypropionate Esters (eg, methyl 3-alkyloxypropionate,
- 2-alkyloxypropionic acid alkyl esters eg methyl 2-alkyloxypropionate, ethyl 2-alkyloxypropionate, propyl 2-alkyloxypropionate etc.
- 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 and the like can be mentioned.
- ketones include methyl ethyl ketone, cyclohexanone, cyclopentanone, 2-heptanone, 3-heptanone and the like.
- Preferred examples of the aromatic hydrocarbons include toluene and xylene. Further, 3-methoxy-N, N-dimethylpropanamide and 3-butoxy-N, N-dimethylpropanamide are also preferable from the viewpoint of solubility improvement.
- the organic solvents may be used alone or in combination of two or more. However, it may be better to reduce aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene etc.) as a solvent due to environmental reasons etc. (For example, 50 mass ppm (parts per part of the total amount of organic solvent) or less, 10 mass ppm or less, or 1 mass ppm or less).
- the organic solvents may be used alone or in combination of two or more.
- methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate is particularly preferable.
- a solvent having a low metal content as the solvent.
- the metal content in the solvent is preferably, for example, 10 parts by weight (pps) or less. If necessary, a solvent having a metal content of mass ppt (parts per trillion) level may be used, and such a high purity solvent is provided by, for example, Toyo Gosei Co., Ltd. (Chemical Industry Journal, November 13, 2015) Day).
- a method of removing impurities such as metal from the solvent for example, distillation (molecular distillation, thin film distillation, etc.) and filtration using a filter can be mentioned.
- distillation molecular distillation, thin film distillation, etc.
- filtration using a filter As a filter hole diameter of a filter used for filtration, 10 micrometers or less are preferred, 5 micrometers or less are more preferred, and 3 micrometers or less are still more preferred.
- the material of the filter is preferably polytetrafluoroethylene, polyethylene or nylon.
- the solvent may contain isomers (compounds having the same number of atoms but different structures). Moreover, only one type of isomer may be contained, or two or more types may be contained.
- the organic solvent preferably has a peroxide content of 0.8 mmol / L or less, and more preferably contains substantially no peroxide.
- the content of the solvent is preferably such that the total solid content of the coloring composition is 5 to 80% by mass.
- the lower limit is preferably 8% by mass or more, and more preferably 10% by mass or more. 60 mass% or less is preferable, 50 mass% or less is more preferable, 40 mass% or less is further more preferable, 35 mass% or less is still more preferable, 30 mass% or less is especially preferable.
- the coloring composition of the present invention may contain a curing accelerator for the purpose of improving the hardness of the pattern or for the purpose of lowering the curing temperature.
- the curing accelerator include thiol compounds.
- the polyfunctional thiol compound As a thiol compound, the polyfunctional thiol compound etc. which have a 2 or more mercapto group in a molecule
- the polyfunctional thiol compound may be added for the purpose of improving the stability, the odor, the resolution, the developability, the adhesion and the like.
- the polyfunctional thiol compound is preferably a secondary alkanethiol, and more preferably a compound having a structure represented by the following formula (T1).
- T1 In the formula (T1), n represents an integer of 2 to 4 and L represents a divalent to tetravalent linking group.
- L is preferably an aliphatic group having 2 to 12 carbon atoms.
- 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 (T2) to (T4), and a compound represented by formula (T2) is preferable.
- One type of thiol compound may be used, or two or more types may be used in combination.
- methylol compounds for example, compounds exemplified as a crosslinking agent in paragraph 0246 of JP-A-2015-34963
- amines for example, compounds exemplified as a crosslinking agent in paragraph 0246 of JP-A-2015-34963
- amines for example, compounds exemplified as a crosslinking agent in paragraph 0246 of JP-A-2015-34963
- amines for example, compounds exemplified as a crosslinking agent in paragraph 0246 of JP-A-2015-34963
- amines for example, compounds exemplified as a crosslinking agent in paragraph 0246 of JP-A-2015-34963
- amines for example, compounds exemplified as a crosslinking agent in paragraph 0246 of JP-A-2015-34963
- amines for example, compounds exemplified as a crosslinking agent in paragraph 0246 of JP-A-2015-34963
- amines for example,
- the content of the curing accelerator is preferably 0.3 to 8.9% by mass in the total solid content of the coloring composition, and is 0.8 to 6.4. % By mass is more preferred.
- the coloring composition of the present invention preferably contains a pigment derivative.
- the pigment derivative include compounds having a structure in which a part of a chromophore is substituted with an acid group, a basic group or a phthalimidomethyl group.
- the chromophores constituting the pigment derivative include quinoline skeleton, benzimidazolone skeleton, diketopyrrolopyrrole skeleton, azo skeleton, phthalocyanine skeleton, anthraquinone skeleton, quinacridone skeleton, dioxazine skeleton, perinone compound Skeletons, perylene skeletons, thioindigo skeletons, isoindoline skeletons, isoindolinone skeletons, quinophthalone skeletons, threne skeletons, metal complex skeletons, etc., and quinoline skeletons, benzimidazolone skeletons, diketo A pyrrolopyrrole skeleton, an azo skeleton, a quinophthalone skeleton, an isoindoline skeleton, and a phthalocyanine skeleton are preferable, and an azo skeleton and a
- a sulfo group and a carboxyl group are preferred, and a sulfo group is more preferred.
- a basic group which a pigment derivative has an amino group is preferable and a tertiary amino group is more preferable.
- the description in paragraphs [0162] to [0182] of JP-A-2011-252065 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 parts by mass, and more preferably 3 to 20 parts by mass with respect to 100 parts by mass of the pigment.
- the pigment derivative may use only 1 type and may use 2 or more types together.
- the coloring composition of the present invention preferably contains a surfactant.
- a surfactant various surfactants such as fluorinated surfactants, nonionic surfactants, cationic surfactants, anionic surfactants, silicone surfactants can be used to further improve the coating property. Fluorinated surfactants are preferred because they can be used.
- liquid properties when prepared as a coating liquid can be improved, and uniformity of coating thickness can be further improved. That is, in the case of film formation using a coating solution to which a coloring composition containing a fluorine-based surfactant is applied, the interfacial tension on the surface of the coating film is reduced, and the uniformity of drying is improved. For this reason, film formation with few coating nonuniformity can be performed more suitably.
- the fluorine content in the fluorine-based surfactant is preferably 3 to 40% by mass, more preferably 5 to 30% by mass, and particularly preferably 7 to 25% by mass.
- the fluorine-based surfactant having a fluorine content in the above range is effective in terms of the uniformity of the thickness of the coating film and the liquid saving property, and the solubility in the coloring composition is also good.
- fluorine-based surfactants for example, Megafac F171, F172, F173, F176, F177, F141, F142, F143, R304, F437, F475, F479, F482, F554, F780 (all, DIC Corporation) , Florard FC430, FC431, FC171 (above, Sumitomo 3M Co., Ltd.), Surfron S-382, SC-101, SC-103, SC-104, SC-105, SC-1068, SC-381, SC -383, S-393, KH-40 (all, manufactured by Asahi Glass Co., Ltd.), PF636, PF656, PF6320, PF6520, PF7002 (all, manufactured by OMNOVA) and the like.
- fluorine-based surfactant compounds described in paragraphs 0015 to 0158 of JP-A-2015-117327, and compounds described in paragraphs 0117 to 0132 of JP-A-2011-132503 can also be used.
- the fluorine-based surfactant is a molecular structure having a functional group containing a fluorine atom, and an acrylic compound in which a portion of the functional group containing a fluorine atom is cleaved when heat is applied and the fluorine atom is volatilized can also be suitably used.
- a fluorochemical surfactant Megafuck DS series (Chemical Chemical Daily, February 22, 2016) manufactured by DIC Corporation (Nikkei Sangyo Shimbun, February 23, 2016), for example, Megafuck DS -21 can be mentioned.
- fluorinated surfactant it is also preferable to use a polymer of a fluorine atom-containing vinyl ether compound having a fluorinated alkyl group or a fluorinated alkylene ether group and a hydrophilic vinyl ether compound as the fluorinated surfactant.
- fluorine-based surfactants can be referred to the description of JP-A-2016-216602, the contents of which are incorporated herein.
- the fluorine-based surfactant a block polymer can also be used.
- the fluorine-based surfactant has a repeating unit derived from a (meth) acrylate compound having a fluorine atom and two or more (preferably five or more) alkyleneoxy groups (preferably ethyleneoxy and propyleneoxy) (meth)
- a fluorine-containing polymer compound containing a repeating unit derived from an acrylate compound can also be preferably used.
- the following compounds are also exemplified as the fluorinated surfactant used in the present invention. In the following formulas,% indicating the proportion of repeating units is mol%.
- the weight average molecular weight of the above-mentioned compounds is preferably 3,000 to 50,000, for example, 14,000.
- a fluorine-containing polymer having an ethylenically unsaturated group in the side chain can also be used as the fluorine-based surfactant.
- Specific examples thereof include compounds described in paragraph Nos. 0050 to 0090 and paragraphs 0289 to 0295 of JP-A-2010-164965.
- Examples of commercially available products include Megafac RS-101, RS-102, RS-718-K, RS-72-K and the like manufactured by DIC Corporation.
- nonionic surfactants glycerol, trimethylolpropane, trimethylolethane and ethoxylates and propoxylates thereof (eg, glycerol propoxylate, glycerol ethoxylate, etc.), polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, Polyoxyethylene oleyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene nonyl phenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, sorbitan fatty acid ester, pluronic L10, L31, L61, L62, 10R5, 17R2, 25R2 (BASF Company), Tetronics 304, 701, 704, 901, 904, 150R1 (BA).
- BA nonionic surfactants
- KP 341 (manufactured by Shin-Etsu Chemical Co., Ltd.), Polyflow No. 1; 75, no. 90, no. 95 (manufactured by Kyoeisha Chemical Co., Ltd.), W001 (manufactured by Yusho Co., Ltd.), and the like.
- anionic surfactant examples include W004, W005, W017 (manufactured by Yusho Co., Ltd.), Sandet BL (manufactured by Sanyo Kasei Co., Ltd.), and the like.
- silicone type surfactant for example, Toray silicone DC3PA, Toray silicone SH7PA, Toray silicone DC11PA, Toray silicone SH21PA, Toray silicone SH28PA, Toray silicone SH29PA, Toray silicone SH30PA, Toray silicone SH8400 (more than Toray Dow Corning ), TSF-4440, TSF-4300, TSF-4445, TSF-4460, TSF-4452 (above, Momentive Performance Materials Inc.), KP341, KF6001, KF6002 (above, Shin-Etsu Silicone Co., Ltd.) , BYK 307, BYK 323, BYK 330 (above, manufactured by Big Chemie Co., Ltd.), and the like.
- the content of the surfactant is preferably 0.001 to 2.0% by mass, and more preferably 0.005 to 1.0% by mass, in the total solid content of the coloring composition. Only one surfactant may be used, or two or more surfactants may be combined. When two or more kinds are contained, the total amount is preferably in the above range.
- the coloring composition of the present invention can contain an ultraviolet absorber.
- an ultraviolet absorber conjugated diene compounds, aminobutadiene compounds, methyldibenzoyl compounds, coumarin compounds, salicylate compounds, benzophenone compounds, benzotriazole compounds, acrylonitrile compounds, hydroxyphenyl triazine compounds and the like can be used. The details of these can be referred to the descriptions of paragraphs 0052 to 0072 of JP 2012-208374 A and paragraphs 0317 to 0334 of JP 2013-68814 A, the contents of which are incorporated herein.
- Specific examples of the ultraviolet absorber include compounds having the following structure.
- UV-503 manufactured by Daito Kagaku Co., Ltd.
- MYUA series Chemical Industry Daily, February 1, 2016 made by Miyoshi Yushi may be used.
- the content of the UV absorber is preferably 0.1 to 10% by mass, and more preferably 0.1 to 5% by mass in the total solid content of the coloring composition. More preferably, 0.1 to 3% by mass is particularly preferable.
- an ultraviolet absorber may use only 1 type and may use 2 or more types. When 2 or more types of ultraviolet absorbers are contained, it is preferable that the total amount of them becomes the said range.
- the coloring composition of the present invention can contain a silane coupling agent.
- the silane coupling agent means a silane compound having a hydrolyzable group and other functional groups.
- the hydrolyzable group is a substituent which is directly bonded to a silicon atom and can form a siloxane bond by hydrolysis reaction and / or condensation reaction.
- a hydrolysable group a halogen atom, an alkoxy group, an acyloxy group etc. are mentioned, for example.
- the silane coupling agent includes at least one group selected from a vinyl group, an epoxy group, a styrene group, a methacryl group, an amino group, an isocyanurate group, an ureido group, a mercapto group, a sulfide group, and an isocyanate group, and an alkoxy group.
- the silane compound which has and is preferable.
- silane coupling agent examples include, for example, N- ⁇ -aminoethyl- ⁇ -aminopropylmethyl dimethoxysilane (Shin-Etsu Chemical Co., Ltd., KBM-602), N- ⁇ -aminoethyl- ⁇ -aminopropyl tri- trile Methoxysilane (Shin-Etsu Chemical Co., Ltd., KBM-603), N- ⁇ -aminoethyl- ⁇ -aminopropyltriethoxysilane (Shin-Etsu Chemical Co., Ltd., KBE-602), ⁇ -aminopropyltrimethoxysilane (Shin-Etsu Chemical) Manufactured by Kogyo Co., Ltd., KBM-903), ⁇ -aminopropyltriethoxysilane (Shin-Etsu Chemical Co., Ltd., KBE-903), 3-methacryloxypropyltrime
- the content of the silane coupling agent is preferably 0.001 to 20% by mass, and 0.01 to 10% by mass in the total solid content of the coloring composition. % Is more preferable, and 0.1 to 5% by mass is particularly preferable.
- the coloring composition of the present invention may contain only one type of silane coupling agent, or may contain two or more types. When 2 or more types of silane coupling agents are contained, it is preferable that the total amount of them becomes the said range.
- the coloring composition of the present invention can contain a polymerization inhibitor.
- a polymerization inhibitor hydroquinone, p-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, t-butyl catechol, benzoquinone, 4,4'-thiobis (3-methyl-6-t-butylphenol), Examples include 2,2′-methylenebis (4-methyl-6-t-butylphenol), N-nitrosophenylhydroxyamine salts (ammonium salts, cerous salts etc.) and the like.
- the content of the polymerization inhibitor is preferably 0.01 to 5% by mass in the total solid content of the coloring composition.
- the coloring composition of the present invention may contain only one type of polymerization inhibitor, or may contain two or more types. When it contains two or more types, it is preferable that the total amount of them becomes the said range.
- additives such as a filler, an adhesion promoter, an antioxidant, an aggregation inhibitor and the like can be blended, if necessary.
- these additives include the additives described in paragraphs [0155] to [0156] of JP-A-2004-295116, the contents of which are incorporated herein.
- the antioxidant for example, a phenol compound, a phosphorus compound (for example, a compound described in paragraph 0042 of JP-A-2011-90147), a thioether compound or the like can be used.
- Adekastab series (AO-20, AO-30, AO-40, AO-50, AO-50F, AO-60G, AO-60, AO-80, AO-A manufactured by ADEKA Co., Ltd.) 330).
- One type of antioxidant may be used or two or more types may be used.
- the coloring composition of the present invention can contain the sensitizer and the light stabilizer described in paragraph 0078 of JP-A-2004-295116, and the thermal polymerization inhibitor described in paragraph 0081 of the same publication.
- the metallic composition may be contained in the coloring composition depending on the raw materials used, etc.
- the content of the Group 2 element (such as calcium and magnesium) in the coloring composition is 50 mass ppm or less from the viewpoint of suppression of defect generation and the like. Is preferably 0.01 to 10 ppm by mass.
- the total amount of the inorganic metal salt in the coloring composition is preferably 100 mass ppm or less, and more preferably 0.5 to 50 mass ppm.
- the water content of the coloring composition of the present invention is usually 3% by mass or less, preferably 0.01 to 1.5% by mass, and more preferably 0.1 to 1.0% by mass.
- the moisture content can be measured by the Karl Fischer method.
- the solid content concentration of the coloring composition of the present invention is preferably 5 to 40% by mass.
- the upper limit is preferably 35% by mass or less, and more preferably 30% by mass or less.
- the lower limit is preferably 8% by mass or more, and more preferably 10% by mass or more.
- the smaller the solid content concentration of the coloring composition the easier it is to form a thin cured film.
- a cured film having a high color value specifically, a red color value
- a cured film having a desired spectral characteristic as a thin film is preferable. It can be formed into
- the coloring composition of the present invention can be used with its viscosity adjusted for the purpose of adjusting the film surface state (flatness and the like), adjusting the film thickness, and the like.
- the value of viscosity can be appropriately selected as necessary, and for example, 0.3 to 50 mPa ⁇ s at 25 ° C. is preferable, and 0.5 to 20 mPa ⁇ s is more preferable.
- As a method of measuring the viscosity for example, using a Toki Sangyo viscometer RE85L (rotor: 1 ° 34 ′ ⁇ R24, measurement range 0.6 to 1200 mPa ⁇ s) and performing temperature control at 25 ° C. It can be measured.
- a storage container of the coloring composition of this invention A well-known storage container can be used.
- a container for the purpose of suppressing the mixing of impurities into the raw materials and the composition, a multilayer bottle in which the inner wall of the container is composed of six types and six layers of resin or a bottle in which six types of resin are seven layers It is also preferred to use.
- a container for example, the container described in JP-A-2015-123351 can be mentioned.
- the colored composition of the present invention can be preferably used as a composition for forming a colored layer in a color filter.
- it can be preferably used as a composition for forming a red colored layer of a color filter.
- the voltage holding ratio of the liquid crystal display device provided with the color filter is preferably 70% or more, more preferably 90% or more .
- Known means for obtaining high voltage holding ratio can be suitably incorporated, and typical means include use of a high purity material (for example, reduction of ionic impurities) and control of the amount of acidic functional groups in the composition Can be mentioned.
- the voltage holding ratio can be measured, for example, by the method described in paragraph 0243 of JP-A-2011-008004 and paragraph 0123 to 0129 of JP-A-2012-224847.
- the coloring composition of the present invention can be prepared by mixing the above-mentioned components.
- all the components may be simultaneously dissolved and / or dispersed in a solvent to prepare a coloring composition, and if necessary, each component may be used as two or more solutions or dispersions as appropriate. Alternatively, they may be mixed at the time of use (at the time of application) to prepare a coloring composition.
- mechanical force used to disperse the pigment includes compression, squeezing, impact, shearing, cavitation and the like.
- specific examples of these processes include bead mills, sand mills, roll mills, ball mills, paint shakers, microfluidizers, high speed impellers, sand grinders, flow jet mixers, high pressure wet atomization, ultrasonic dispersion and the like.
- the process and the dispersing machine for dispersing the pigment are the dispersion technology and industrial application centering on “Dispersion Technology Complete, Information Technology Co., Ltd. issued July 15, 2005” and “suspension (solid / liquid dispersion system)” The process and the dispersing machine described in Paragraph No.
- the particles may be subjected to a refinement treatment in a salt milling step.
- the materials, equipment, processing conditions and the like used in the salt milling step can be referred to, for example, the descriptions of JP-A-2015-194521 and JP-A-2012-04629.
- a filter for the purpose of the removal of a foreign material, reduction of a defect, etc.
- a filter if it is a filter conventionally used for filtration applications etc., it can be used, without being limited in particular.
- a fluorine resin such as polytetrafluoroethylene (PTFE), a polyamide resin such as nylon (for example, nylon-6, nylon-6, 6), a polyolefin resin such as polyethylene or polypropylene (PP) (high density and / or super
- PP polypropylene
- a filter using a material such as a high molecular weight polyolefin resin can be mentioned.
- polypropylene including high density polypropylene
- nylon are preferable.
- the pore diameter of the filter is suitably about 0.01 to 7.0 ⁇ m, preferably about 0.01 to 3.0 ⁇ m, and more preferably about 0.05 to 0.5 ⁇ m.
- the filter using a fiber-like filter medium as a filter.
- the fibrous filter medium include polypropylene fiber, nylon fiber, glass fiber and the like.
- Specific examples of the filter using a fiber-like filter medium include filter cartridges of SBP type series (SBP 008, etc.), TPR type series (TPR 002, TPR 005, etc.), and SHPX type series (SHPX 003, etc.) manufactured by Loki Techno. .
- filters When using filters, different filters may be combined. In that case, filtration with each filter may be performed only once or may be performed twice or more.
- filters of different pore sizes may be combined within the range described above.
- the pore size here can refer to the nominal value of the filter manufacturer.
- a commercially available filter for example, it is selected from various filters provided by Nippon Pall Co., Ltd. (DFA4201 NXEY etc.), Advantech Toyo Co., Ltd., Japan Entegris Co., Ltd. (old Japan Microlith Co., Ltd.) or Kitz Micro Filter Co., Ltd. can do.
- filtration with a 1st filter may be performed only with a dispersion liquid, and you may filter with a 2nd filter, after mixing other components.
- the second filter one formed of the same material as the first filter can be used.
- the cured film of the present invention is a cured film obtained from the coloring composition of the present invention described above.
- the thickness of the cured film can be appropriately adjusted according to the purpose.
- the film thickness is preferably 20 ⁇ m or less, more preferably 10 ⁇ m or less, and still more preferably 5 ⁇ m or less.
- the lower limit of the film thickness is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, and still more preferably 0.3 ⁇ m or more.
- the pattern forming method of the present invention comprises the steps of forming a colored composition layer on a support using the above-mentioned colored composition of the present invention, and forming a pattern on the colored composition layer by photolithography or dry etching. And forming.
- the pattern formation by photolithography includes the steps of forming a colored composition layer on a support using a colored composition, exposing the colored composition layer in a pattern, and unexposed areas of the colored composition layer. And the step of removing by development to form a pattern. If necessary, a step of baking the colored composition layer (pre-baking step) and a step of baking the developed pattern (post-baking step) may be provided.
- a colored composition layer is formed on a support using a colored composition, and the colored composition layer is cured to form a cured product layer;
- the method includes the steps of forming a resist layer, patterning the resist layer to obtain a resist pattern, and dry etching the cured product layer using the resist pattern as an etching mask to form a pattern. Each step will be described below.
- the colored composition is used to form a colored composition layer on a support.
- a support body There is no limitation in particular as a support body, According to a use, it can select suitably.
- a glass substrate, a substrate for a solid-state imaging device provided with a solid-state imaging device (light receiving device) such as a CCD or a CMOS, a silicon substrate, etc. may be mentioned.
- a subbing layer may be provided to improve the adhesion with the upper layer, to prevent the diffusion of substances, or to planarize the surface.
- various methods such as slit coating, ink jet method, spin coating, cast coating, roll coating, screen printing can be used.
- the colored composition layer formed on the support may be dried (prebaked). In the case of forming a pattern by a low temperature process, the prebaking may not be performed.
- the prebaking temperature is preferably 150 ° C. or less, more preferably 120 ° C. or less, and still more preferably 110 ° C. or less.
- the lower limit may be, for example, 50 ° C. or more, and may be 80 ° C. or more.
- the pre-bake time is preferably 10 seconds to 300 seconds, more preferably 40 to 250 seconds, and still more preferably 80 to 220 seconds. Drying can be performed on a hot plate, an oven or the like.
- ⁇ exposure step the colored composition layer is exposed in a pattern (exposure step).
- pattern exposure can be performed by exposing the coloring composition layer through a mask having a predetermined mask pattern using an exposure apparatus such as a stepper. Thereby, the exposed portion can be cured.
- radiation which can be used at the time of exposure, ultraviolet rays such as g-line and i-line are preferably used (particularly preferably i-line).
- Irradiation dose (exposure dose) for example, preferably 0.03 ⁇ 2.5J / cm 2, more preferably 0.05 ⁇ 1.0J / cm 2.
- the oxygen concentration at the time of exposure can be appropriately selected, and in addition to being performed under the atmosphere, for example, under a low oxygen atmosphere having an oxygen concentration of 19% by volume or less (for example, 15% by volume, 5% by volume, or substantially It may be exposed with no oxygen, and may be exposed under a high oxygen atmosphere (for example, 22% by volume, 30% by volume, or 50% by volume) in which the oxygen concentration exceeds 21% by volume.
- the exposure intensity is can be set appropriately, usually 1000W / m 2 ⁇ 100000W / m 2 ( e.g., 5000W / m 2, 15000W / m 2, or, 35000W / m 2) selected from the range of Can.
- Oxygen concentration and exposure illuminance may appropriately combined conditions, for example, illuminance 10000 W / m 2 at an oxygen concentration of 10 vol%, oxygen concentration of 35 vol% can be such illuminance 20000W / m 2.
- the unexposed area of the colored composition layer is removed by development to form a pattern.
- the development removal of the unexposed part of a coloring composition layer can be performed using a developing solution.
- a developing solution an organic alkaline developing solution which does not cause damage to a solid-state imaging device or circuit of a base is desirable.
- the temperature of the developing solution is preferably, for example, 20 to 30.degree.
- the development time is preferably 20 to 180 seconds.
- the process of shaking off the developer every 60 seconds and supplying the developer anew may be repeated several times.
- an alkaline aqueous solution obtained by diluting an alkaline agent with pure water is preferably used.
- the alkaline agent include aqueous ammonia, ethylamine, diethylamine, dimethylethanolamine, diglycolamine, diethanolamine, hydroxyamine, ethylenediamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide and tetrabutylammonium hydroxide.
- Organic alkaline compounds such as benzyl, trimethyltrimethylammonium hydroxide, dimethylbis (2-hydroxyethyl) ammonium hydroxide, choline, pyrrole, piperidine, 1,8-diazabicyclo [5.4.0] -7-undecene, or water Inorganic materials such as sodium oxide, potassium hydroxide, sodium carbonate, sodium hydrogencarbonate, sodium silicate, sodium metasilicate Potassium compounds may be mentioned.
- the concentration of the alkaline agent in the alkaline aqueous solution is preferably 0.001 to 10% by mass, and more preferably 0.01 to 1% by mass.
- the developer may further contain a surfactant.
- the surfactant mentioned above is mentioned and nonionic surfactant is preferable.
- the developer may be prepared once as a concentrate and diluted to a concentration required for use, from the viewpoint of transportation and storage convenience.
- the dilution ratio is not particularly limited, but can be set, for example, in the range of 1.5 to 100 times.
- clean (rinse) when using the developing solution which consists of such alkaline aqueous solution, it is preferable to wash
- Post-baking is a heat treatment after development to complete curing, and the heating temperature is preferably 100 to 240 ° C., and more preferably 200 to 240 ° C., for example.
- the support on which the cured film is formed includes an organic electroluminescent (organic EL) element, an image sensor having a photoelectric conversion film made of an organic material, and the like
- the post-baking temperature is 150 ° C. or less Is preferred. The lower limit can be, for example, 50 ° C. or higher.
- Post-baking is performed continuously or batchwise using a heating means such as a hot plate, convection oven (hot air circulating dryer), high frequency heater or the like so that the film (cured film) after development becomes the above conditions. It can be carried out.
- the Young's modulus of the post-baked film (cured film) is preferably 0.5 to 20 GPa, and more preferably 2.5 to 15 GPa.
- the cured film preferably has high flatness.
- the surface roughness Ra is preferably 100 nm or less, more preferably 40 nm or less, and still more preferably 15 nm or less.
- the lower limit is not defined, but is preferably, for example, 0.1 nm or more.
- the surface roughness can be measured, for example, using an AFM (atomic force microscope) Dimension 3100 manufactured by Veeco.
- the contact angle of water on the cured film can be appropriately set to a preferable value, but is typically in the range of 50 to 110 °.
- the contact angle can be measured, for example, using a contact angle meter CV-DT ⁇ A type (manufactured by Kyowa Interface Science Co., Ltd.).
- the volume resistivity of each pattern (pixel) be high.
- the volume resistivity of the pixel is preferably 10 9 ⁇ ⁇ cm or more, and more preferably 10 11 ⁇ ⁇ cm or more.
- the upper limit is not specified, but is preferably 10 14 ⁇ ⁇ cm or less, for example.
- the volume resistance value of the pixel can be measured, for example, using an ultra-high resistance meter 5410 (manufactured by Advantest Corporation).
- Patterning by dry etching is performed by applying a coloring composition onto a support to cure the formed coloring composition layer to form a cured product layer, and then a resist layer patterned on the cured product layer. And then dry etching the cured product layer using the patterned resist layer as a mask.
- the resist layer is preferably formed by applying a positive or negative photosensitive composition on the cured product layer and drying it. As a composition used for formation of a resist layer, a positive photosensitive composition is preferable.
- photosensitive compositions sensitive to radiation such as ultraviolet (g-ray, h-ray, i-ray), far-ultraviolet radiation including KrF radiation, ArF radiation and the like, electron beam, ion beam and X-ray are preferred.
- the above-mentioned positive photosensitive composition is preferably a photosensitive composition sensitive to KrF ray, ArF ray, i ray, X ray), and from the viewpoint of fine processability, the photosensitive composition sensitive to KrF ray is more preferable preferable.
- positive photosensitive composition positive resist compositions described in JP-A-2009-237173 and JP-A-2010-134283 are suitably used.
- the color filter of the present invention has the cured film of the present invention described above.
- the thickness of the cured film can be appropriately adjusted according to the purpose.
- the film thickness is preferably 20 ⁇ m or less, more preferably 10 ⁇ m or less, and still more preferably 5 ⁇ m or less.
- the lower limit of the film thickness is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, and still more preferably 0.3 ⁇ m or more.
- the color filter of the present invention can be used for a solid-state imaging device such as a CCD (charge coupled device) or a CMOS (complementary metal oxide semiconductor) or an image display device.
- CCD charge coupled device
- CMOS complementary metal oxide semiconductor
- the solid-state imaging device of the present invention has the cured film of the present invention described above.
- the configuration of the solid-state imaging device of the present invention is not particularly limited as long as the cured film of the present invention is provided and functions as a solid-state imaging device, and examples thereof include the following configurations.
- the substrate there are a plurality of photodiodes forming the light receiving area of a solid-state imaging device (CCD (charge coupled device) image sensor, CMOS (complementary metal oxide semiconductor) image sensor, etc.) and transfer electrodes made of polysilicon etc.
- CCD charge coupled device
- CMOS complementary metal oxide semiconductor
- Device protective film formed of silicon nitride or the like formed on the light shielding film so as to cover the entire surface of the light shielding film and the photodiode light receiving portion. And has a color filter on the device protection film.
- the device has a light collecting means (for example, a micro lens etc., hereinafter the same) on the device protective film and under the color filter (closer to the substrate) or a structure having the light collecting means on the color filter It may be.
- the color filter may have a structure in which a cured film forming each colored pixel is embedded in a space partitioned into, for example, a grid shape by partition walls.
- the partition walls in this case preferably have a low refractive index for each colored pixel.
- an imaging device having such a structure devices described in JP 2012-227478 A and JP 2014-179577 A can be mentioned.
- the imaging device provided with the solid-state imaging device according to the present invention can be used not only for digital cameras and electronic devices (such as mobile phones) having an imaging function, but also for in-vehicle cameras and surveillance cameras.
- the cured film of the present invention can be used in an image display device such as a liquid crystal display device or an organic electroluminescence display device.
- an image display device such as a liquid crystal display device or an organic electroluminescence display device.
- an image display device such as a liquid crystal display device or an organic electroluminescence display device.
- electroluminescence display device for the definition of the image display device and details of each image display device, for example, “Electronic display device (authored by Akio Sasaki, Inc., Industrial Research Association, published in 1990)”, “Display device (authored by Ibuki, industrial book ( Co., Ltd., published in Heisei 1973).
- the liquid crystal display device is described, for example, in "Next-generation liquid crystal display technology (edited by Tatsuo Uchida, Industrial Research Association, Inc., 1994)".
- ⁇ Dispersion stability evaluation> The viscosity of the dispersion obtained above was measured with “RE-85L” manufactured by Toki Sangyo Co., Ltd., and after the dispersion was allowed to stand at 45 ° C. for 3 days, the viscosity was measured again. Dispersion stability was evaluated according to the following evaluation criteria from the viscosity difference ( ⁇ Vis) before and after standing. The smaller the viscosity difference ( ⁇ Vis), the better the dispersion stability. The viscosity of the dispersion was measured at a temperature of 25 ° C. A: ⁇ Vis is 0.5 or less B: ⁇ Vis is greater than 0.5 and 1.0 or less C: ⁇ Vis is greater than 1.0 and 2.0 or less D: ⁇ Vis is greater than 2.0
- P-4 Disperbyk-111 (manufactured by BYK Chemie)
- P-5 20 mass% PGMEA solution of resin of the following structure.
- Each coloring composition is spin-coated on a glass substrate so that the film thickness after post-baking becomes 0.4 ⁇ m, dried on a hot plate at 100 ° C. for 120 seconds, and then 300 ° C. using a hot plate at 200 ° C.
- Heat treatment was performed for a second to form a cured film.
- the spectral evaluation was evaluated by measuring the transmittance at a wavelength of 580 nm. The lower the transmittance at a wavelength of 580 nm, the better the spectral characteristics as a red colored layer.
- the example had a lower transmittance than the comparative example, and had preferable spectral characteristics as a red colored layer. Moreover, when pattern formation was performed by the photolithographic method in the following procedures about the coloring composition of an Example, it was excellent in pattern formability.
- the coloring composition of Examples 1 to 38 is spin coated on an 8-inch (20.32 cm) silicon wafer substrate so that the film thickness after post-baking becomes 0.4 ⁇ m, and dried with a hot plate at 100 ° C. for 120 seconds. Thus, a colored composition layer was obtained.
- An i-line stepper FPA-3000i5 + (Canon Co., Ltd.) is used for this coloring composition layer, and a mask pattern in which square pixels each having a side of 1.1 ⁇ m are arranged in an area of 4 mm ⁇ 3 mm on the substrate is used.
- the colored composition layer after exposure was subjected to paddle development at 23 ° C. for 60 seconds using a 0.3 mass% aqueous solution of tetramethyl ammonium hydroxide. Thereafter, rinsing was performed using water in a spin shower. Thereafter, the water droplets were blown off with high-pressure air, and the silicon wafer was naturally dried, and then post-baked at 220 ° C. for 300 seconds using a hot plate to form a pattern.
- the raw materials used for preparation of a coloring composition are as follows.
- Dispersion 3 Dispersion 6, Dispersion 10, Dispersion 12, Dispersion 14, Dispersion 16, Dispersion 18, Dispersion 20, Dispersion 24, Dispersion 26, Dispersion 34, Dispersion 37, Dispersion 41, dispersion liquid 43, dispersion liquid 45, dispersion liquid 49, dispersion liquid 51, dispersion liquid 55, dispersion liquid 57, dispersion liquid 65, dispersion liquid 68, dispersion liquid 72, dispersion liquid 72, dispersion liquid 74, dispersion liquid 76, Dispersion liquid 78, dispersion liquid 80, dispersion liquid 81, dispersion liquid 83, dispersion liquid 85, dispersion liquid 89, dispersion liquid 91, dispersion liquid 97, dispersion liquid 98, dispersion liquid 99, dispersion liquid 100, dispersion liquid 100, dispersion liquid 101, dispersion liquid 102, dispersion liquid 104, dispersion liquid 105, dispersion liquid 107, dispersion
- Yellow pigment dispersion Y1 prepared by the following method.
- C. 10.91 parts by mass of I pigment yellow 139, 1.5 parts by mass of the above-mentioned derivative 1, 3.78 parts by mass of dispersant P-6 (resin of the following structure), and 83.87 parts by mass of PEGMA
- 230 parts by mass of zirconia beads with a diameter of 0.3 mm were added, dispersion was performed for 5 hours using a paint shaker, and the beads were separated by filtration to produce a yellow pigment dispersion Y1.
- Dispersant P-6 30% by weight PGMEA solution of resin of the following structure.
- the numerical value appended to the main chain is the molar ratio
- E1 KAYARAD DPHA (manufactured by Nippon Kayaku Co., Ltd.)
- E2 Alonics M-305 (manufactured by Toagosei Co., Ltd.)
- E3 NK ester A-TMMT (manufactured by Shin-Nakamura Chemical Co., Ltd.)
- E4 KAYARAD RP-1040 (manufactured by Nippon Kayaku Co., Ltd.)
- E5 ALONIX TO-2349 (manufactured by Toagosei Co., Ltd.)
- F1 IRGACURE-OXE01 (manufactured by BASF)
- F2 IRGACURE-OXE02 (manufactured by BASF)
- F3 Compound of the following structure
- F4 IRGACURE 369 (manufactured by BASF)
- F5 compound of the following structure
- Colored Composition (Production Example 2) 70.8 parts by mass of the dispersion 14 described above as a red pigment dispersion, 18.9 parts by mass of the yellow pigment dispersion Y1, 2.6 parts by mass of the epoxy compound EP1, and 2.7 of the surfactant H2
- the colored composition 101 was prepared by mixing 50 parts by mass of PGMEA with the parts by mass.
- EP1 1,2-epoxy-4- (2-oxiranyl) cyclohexane adduct of 2,2-bis (hydroxymethyl) -1-butanol (manufactured by Daicel Corporation, EHPE 3150, Mw 23000)
- the resulting colored composition 101 is spin-coated on a glass substrate so that the film thickness after post-baking becomes 0.4 ⁇ m, dried on a hot plate at 100 ° C. for 120 seconds, and then a hot plate at 200 ° C. Heat treatment (post bake) was performed for 300 seconds to form a cured film. Transmission of light in the wavelength range of 300 to 1000 nm using a UV-visible near-infrared spectrophotometer U-4100 (manufactured by Hitachi High-Technologies Corp.) (ref. Glass substrate) on which the cured film has been formed. The rate was measured. The transmittance at a wavelength of 580 nm was 10%.
- the coloring composition 101 is spin-coated on a silicon wafer substrate of 8 inches (20.32 cm) so that the film thickness after post-baking becomes 0.4 ⁇ m, and dried with a hot plate at 100 ° C. for 120 seconds. Heat treatment (post bake) was performed for 300 seconds using a hot plate at 200 ° C. to form a colored layer. Next, a positive photoresist (FHi 622BC, manufactured by Fujifilm Electronics Materials Co., Ltd.) was applied onto the colored layer, and dried with a hot plate at 100 ° C. for 120 seconds to form a photoresist layer having a thickness of 0.8 ⁇ m.
- a positive photoresist FHi 622BC, manufactured by Fujifilm Electronics Materials Co., Ltd.
- RF (high frequency) power 800 W
- antenna bias 400 W
- wafer bias 200 W
- internal pressure of chamber 4.0 Pa
- substrate temperature 50 in a dry etching apparatus (U-621, manufactured by Hitachi High-Technologies Corp.)
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Abstract
Description
<1> 芳香族環に対して、酸素原子、硫黄原子または窒素原子が結合した基が導入された芳香族環基がジケトピロロピロール骨格に結合した構造を有する顔料Aと、
硬化性基を有する化合物と、を含む着色組成物であって、
着色組成物の全固形分中における顔料Aの含有量が40質量%以上である、着色組成物。
<2> 芳香族環基は、下記式(AR-1)で表される基である、<1>に記載の着色組成物;
式(AR-1)
R2は水素原子、アルキル基、アリール基またはヘテロアリール基を表し、
n1は0~4の整数を表し、
Xは酸素原子、硫黄原子または窒素原子を表し、
Xが酸素原子または硫黄原子の場合は、mは1を表し、Xが窒素原子の場合は、mは2を表し、
波線はジケトピロロピロール骨格との結合部位を表す。
<3> 顔料Aは、下記式(1)で表される化合物である、<1>または<2>に記載の着色組成物;
R12およびR14はそれぞれ独立して水素原子、アルキル基、アリール基またはヘテロアリール基を表し、
n11およびn13はそれぞれ独立して0~4の整数を表し、
X12およびX14はそれぞれ独立して酸素原子、硫黄原子または窒素原子を表し、
X12が酸素原子または硫黄原子の場合は、m12は1を表し、X12が窒素原子の場合は、m12は2を表し、
X14が酸素原子または硫黄原子の場合は、m14は1を表し、X14が窒素原子の場合は、m14は2を表す。
<4> 顔料Aは、下記式(2)で表される化合物である、<1>または<2>に記載の着色組成物;
R12およびR14はそれぞれ独立して水素原子、アルキル基、アリール基またはヘテロアリール基を表し、
n11およびn13はそれぞれ独立して0~4の整数を表し、
X12およびX14はそれぞれ独立して酸素原子、硫黄原子または窒素原子を表し、
X12が酸素原子または硫黄原子の場合は、m12は1を表し、X12が窒素原子の場合は、m12は2を表し、
X14が酸素原子または硫黄原子の場合は、m14は1を表し、X14が窒素原子の場合は、m14は2を表す。
<5> 硬化性基を有する化合物は、エチレン性不飽和基を有する化合物およびエポキシ基を有する化合物から選ばれる少なくとも1種を含む、<1>~<4>のいずれかに記載の着色組成物。
<6> 硬化性基を有する化合物は、エチレン性不飽和基を有する樹脂を含む、<1>~<5>のいずれかに記載の着色組成物。
<7> 硬化性基を有する化合物は、エチレン性不飽和基を有する化合物を含み、かつ、更に光重合開始剤を含む、<1>~<6>のいずれかに記載の着色組成物。
<8> 着色組成物は、エチレン性不飽和基を有するモノマーと、樹脂とを含み、
着色組成物に含まれるエチレン性不飽和基を有するモノマーの質量M1と、着色組成物に含まれる樹脂の質量B1との比であるM1/B1が0.2以下である、<1>~<7>のいずれかに記載の着色組成物。
<9> <1>~<8>のいずれかに記載の着色組成物から得られる硬化膜。
<10> <1>~<8>のいずれかに記載の着色組成物を用いて支持体上に着色組成物層を形成する工程と、フォトリソグラフィ法またはドライエッチング法により着色組成物層に対してパターンを形成する工程と、を有するパターン形成方法。
<11> <9>に記載の硬化膜を有するカラーフィルタ。
<12> <9>に記載の硬化膜を有する固体撮像素子。
<13> <9>に記載の硬化膜を有する画像表示装置。
本明細書における基(原子団)の表記において、置換および無置換を記していない表記は、置換基を有さない基と共に置換基を有する基を包含する。例えば、「アルキル基」とは、置換基を有さないアルキル基(無置換アルキル基)のみならず、置換基を有するアルキル基(置換アルキル基)をも包含する。
本明細書において「露光」とは、特に断らない限り、光を用いた露光を意味するのみならず、電子線、イオンビーム等の粒子線を用いた描画も露光に含まれる。また、露光に用いられる光としては、一般的に、水銀灯の輝線スペクトル、エキシマレーザーに代表される遠紫外線、極紫外線(EUV光)、X線、電子線等の活性光線または放射線が挙げられる。
本明細書において「~」を用いて表される数値範囲は、「~」の前後に記載される数値を下限値および上限値として含む範囲を意味する。
本明細書において、全固形分とは、組成物の全成分から溶剤を除いた成分の合計量をいう。
本明細書において、「(メタ)アクリレート」は、アクリレートおよびメタクリレートの双方、または、いずれかを表し、「(メタ)アクリル」は、アクリルおよびメタクリルの双方、または、いずれかを表し、「(メタ)アリル」は、アリルおよびメタリルの双方、または、いずれかを表し、「(メタ)アクリロイル」は、アクリロイルおよびメタクリロイルの双方、または、いずれかを表す。
本明細書において「工程」との語は、独立した工程を意味するだけではなく、他の工程と明確に区別できない場合であってもその工程の所期の作用が達成されれば、本用語に含まれる。
本明細書において、重量平均分子量(Mw)および数平均分子量(Mn)は、ゲルパーミエーションクロマトグラフィ(GPC)により測定したポリスチレン換算値として定義される。
本発明の着色組成物は、
芳香族環に対して、酸素原子、硫黄原子または窒素原子が結合した基が導入された芳香族環基がジケトピロロピロール骨格に結合した構造を有する顔料Aと、
硬化性基を有する化合物と、を含み、
着色組成物の全固形分中における上記顔料Aの含有量が40質量%以上であることを特徴とする。
また、顔料Aは従来の赤色顔料に比べて赤色の色価が高いため、従来の赤色顔料と同等の分光特性を達成するために必要とされる配合量よりも少ない配合量で所望の分光を達成することができるため、顔料以外の成分の配合量を高めることもでき、処方設計の自由度が高い。
また、顔料Aは組成物中における分散性にも優れる。顔料Aが有する上記の芳香族環基は、芳香族環に対して、酸素原子、硫黄原子または窒素原子が結合した基が導入されているので、芳香族環上のπ電子密度が増加して分散剤などとの相互作用性が向上したためであると推測される。
本発明の着色組成物は、芳香族環に対して、酸素原子、硫黄原子または窒素原子が結合した基が導入された芳香族環基がジケトピロロピロール骨格に結合した構造を有する顔料Aを含有する。この顔料はジケトピロロピロール骨格を有する顔料である。
式(AR-1)
R2は水素原子、アルキル基、アリール基またはヘテロアリール基を表し、
n1は0~4の整数を表し、
Xは酸素原子、硫黄原子または窒素原子を表し、
Xが酸素原子または硫黄原子の場合は、mは1を表し、Xが窒素原子の場合は、mは2を表し、
波線はジケトピロロピロール骨格との結合部位を表す。
R12およびR14はそれぞれ独立して水素原子、アルキル基、アリール基またはヘテロアリール基を表し、
n11およびn13はそれぞれ独立して0~4の整数を表し、
X12およびX14はそれぞれ独立して酸素原子、硫黄原子または窒素原子を表し、
X12が酸素原子または硫黄原子の場合は、m12は1を表し、X12が窒素原子の場合は、m12は2を表し、
X14が酸素原子または硫黄原子の場合は、m14は1を表し、X14が窒素原子の場合は、m14は2を表す。
置換基Tとして、次の基が挙げられる。アルキル基(好ましくは炭素数1~30のアルキル基)、アルケニル基(好ましくは炭素数2~30のアルケニル基)、アルキニル基(好ましくは炭素数2~30のアルキニル基)、アリール基(好ましくは炭素数6~30のアリール基)、アミノ基(好ましくは炭素数0~30のアミノ基)、アルコキシ基(好ましくは炭素数1~30のアルコキシ基)、アリールオキシ基(好ましくは炭素数6~30のアリールオキシ基)、ヘテロアリールオキシ基、アシル基(好ましくは炭素数1~30のアシル基)、アルコキシカルボニル基(好ましくは炭素数2~30のアルコキシカルボニル基)、アリールオキシカルボニル基(好ましくは炭素数7~30のアリールオキシカルボニル基)、ヘテロアリールオキシカルボニル基、アシルオキシ基(好ましくは炭素数2~30のアシルオキシ基)、アシルアミノ基(好ましくは炭素数2~30のアシルアミノ基)、アルコキシカルボニルアミノ基(好ましくは炭素数2~30のアルコキシカルボニルアミノ基)、アリールオキシカルボニルアミノ基(好ましくは炭素数7~30のアリールオキシカルボニルアミノ基)、スルファモイル基(好ましくは炭素数0~30のスルファモイル基)、カルバモイル基(好ましくは炭素数1~30のカルバモイル基)、アルキルチオ基(好ましくは炭素数1~30のアルキルチオ基)、アリールチオ基(好ましくは炭素数6~30のアリールチオ基)、ヘテロアリールチオ基(好ましくは炭素数1~30)、アルキルスルホニル基(好ましくは炭素数1~30)、アリールスルホニル基(好ましくは炭素数6~30)、ヘテロアリールスルホニル基(好ましくは炭素数1~30)、アルキルスルフィニル基(好ましくは炭素数1~30)、アリールスルフィニル基(好ましくは炭素数6~30)、ヘテロアリールスルフィニル基(好ましくは炭素数1~30)、ウレイド基(好ましくは炭素数1~30)、ヒドロキシ基、カルボキシル基、スルホ基、リン酸基、カルボン酸アミド基、スルホン酸アミド基、イミド酸基、メルカプト基、ハロゲン原子、シアノ基、アルキルスルフィノ基、アリールスルフィノ基、ヒドラジノ基、イミノ基、ヘテロアリール基(好ましくは炭素数1~30)。これらの基は、さらに置換可能な基である場合、さらに置換基を有してもよい。置換基としては、上述した置換基Tで説明した基が挙げられる。
また、着色組成物に含まれるジケトピロロピロール骨格を有する化合物の全質量中における顔料Aの割合は、80質量%以上であることが好ましく、90質量%以上であることがより好ましく、95質量%以上であることが更に好ましく、実質的に顔料Aのみであることが特に好ましい。なお、着色組成物に含まれるジケトピロロピロール骨格を有する化合物が実質的に顔料Aのみである場合とは、着色組成物に含まれるジケトピロロピロール骨格を有する化合物の全質量中における顔料Aの割合が99質量%以上であることを意味し、99.5質量%以上であることが好ましく、99.9質量%以上であることが更に好ましく、顔料Aのみで構成されていることが特に好ましい。
また、着色組成物に含まれる着色剤の全質量中における顔料Aの割合は、60質量%以上であることが好ましく、70質量%以上であることがより好ましく、80質量%以上であることが更に好ましい。上限は、90質量%以下とすることができる。
本発明の着色組成物は上述した顔料A以外の着色剤(以下、他の着色剤ともいう)を含有することができる。他の着色剤は、顔料であってもよく、染料であってもよい。顔料と染料とを併用してもよい。本発明で用いられる着色剤は、顔料を含むことが好ましい。また、着色剤中における顔料の含有量は、50質量%以上であることが好ましく、70質量%以上であることがより好ましく、80質量%以上であることが更に好ましく、90質量%以上であることが特に好ましい。また、着色剤は顔料のみであってもよい。
C.I.ピグメントオレンジ2,5,13,16,17:1,31,34,36,38,43,46,48,49,51,52,55,59,60,61,62,64等(以上、オレンジ色顔料)、
C.I.ピグメントレッド1,2,3,4,5,6,7,9,10,14,17,22,23,31,38,41,48:1,48:2,48:3,48:4,49,49:1,49:2,52:1,52:2,53:1,57:1,60:1,63:1,66,67,81:1,81:2,81:3,83,88,90,105,112,119,122,123,144,146,149,150,155,166,168,169,170,171,172,175,176,177,178,179,184,185,187,188,190,200,202,206,207,208,209,210,216,220,224,226,242,246,254,255,264,269,270,272,279等(以上、赤色顔料)、
C.I.ピグメントグリーン7,10,36,37,58,59等(以上、緑色顔料)、
C.I.ピグメントバイオレット1,19,23,27,32,37,42等(以上、紫色顔料)、
C.I.ピグメントブルー1,2,15,15:1,15:2,15:3,15:4,15:6,16,22,60,64,66,79,80等(以上、青色顔料)。
また、青色顔料として、リン原子を有するアルミニウムフタロシアニン化合物を用いることもできる。具体例としては、特開2012-247591号公報の段落0022~0030、特開2011-157478号公報の段落0047に記載の化合物などが挙げられる。
また、黄色着色剤の含有量は、顔料Aの100質量部に対して40質量部以下であることが好ましい。下限は、1質量部以上とすることができ、5質量部以上とすることもできる。上限は、30質量部以下であることが好ましく、20質量部以下であることがより好ましい。
また、顔料Aと他の着色剤との合計の含有量は着色組成物の全固形分中50~90質量%であることが好ましい。下限は、51質量%以上であることが好ましく、55質量%以上であることがより好ましい。上限は、85質量%以下であることが好ましく、80質量%以下であることがより好ましい。
また、顔料Aと黄色着色剤との合計の含有量は着色組成物の全固形分中50~90質量%であることが好ましい。下限は、51質量%以上であることが好ましく、55質量%以上であることがより好ましい。上限は、85質量%以下であることが好ましく、80質量%以下であることがより好ましい。
本発明の着色組成物は、硬化性基を有する化合物を含有する。硬化性基を有する化合物が硬化する際の反応機構については特に限定されない。ラジカル重合反応、カチオン重合反応、縮重合反応、求核付加反応、置換反応による架橋反応等が挙げられる。硬化性基はを有する化合物は、ラジカル重合反応により硬化する化合物であることが好ましい。硬化性基としては、エチレン性不飽和基、エポキシ基などが挙げられる。エチレン性不飽和基としては、ビニル基、ビニロキシ基、アリル基、メタリル基、(メタ)アクリロイル基、スチレン基、シンナモイル基およびマレイミド基が挙げられ、(メタ)アクリロイル基、スチレン基、マレイミド基が好ましく、(メタ)アクリロイル基がより好ましく、アクリロイル基が特に好ましい。
本発明において、硬化性化合物として用いられるエチレン性不飽和基を有する化合物(以下、重合性化合物ともいう)としては、モノマー(エチレン性不飽和基を有するモノマー)であってもよく、樹脂(エチレン性不飽和基を有する樹脂)であってもよい。以下、エチレン性不飽和基を有する化合物を重合性化合物ともいう。また、エチレン性不飽和基を有するモノマーを重合性モノマーともいう。また、エチレン性不飽和基を有する樹脂を重合性樹脂ともいう。
また、重合性モノマーとしては、8UH-1006、8UH-1012(以上、大成ファインケミカル(株)製)、ライトアクリレートPOB-A0(共栄社化学(株)製)などを用いることも好ましい。
また、重合性モノマーとしては、特開2017-48367号公報、特許第6057891号公報、特許第6031807号公報に記載されている化合物を用いることもできる。
重合性樹脂のC=C価[mmol/g]=(低分子成分(a)の含有量[ppm]/低分子成分(a)の分子量[g/mol])/(重合性樹脂の秤量値[g]×(重合性樹脂の固形分濃度[質量%]/100)×10)
上記式において、RG3は、水素原子またはメチル基を表す。
上記式において、QG1は、-O-または-NH-を表し、LG1は、単結合または2価の連結基を表す。2価の連結基としては、アルキレン基(好ましくは炭素数1~12のアルキレン基)、アルキレンオキシ基(好ましくは炭素数1~12のアルキレンオキシ基)、オキシアルキレンカルボニル基(好ましくは炭素数1~12のオキシアルキレンカルボニル基)、アリーレン基(好ましくは炭素数6~20のアリーレン基)、-NH-、-SO-、-SO2-、-CO-、-O-、-COO-、OCO-、-S-およびこれらの2以上を組み合わせてなる基が挙げられる。
RG4は、水素原子または置換基を表す。置換基としては、アルキル基、アリール基、ヘテロアリール基、アルコキシ基、アリールオキシ基、ヘテロアリールオキシ基、アルキルチオエーテル基、アリールチオエーテル基、ヘテロアリールチオエーテル基等が挙げられる。
式(A-1-3)におけるL3が表す2価の連結基としては、アルキレン基(好ましくは炭素数1~12のアルキレン基)、アルケニレン基(好ましくは炭素数2~12のアルケニレン基)、アルキレンオキシ基(好ましくは炭素数1~12のアルキレンオキシ基)、オキシアルキレンカルボニル基(好ましくは炭素数1~12のオキシアルキレンカルボニル基)、アリーレン基(好ましくは炭素数6~20のアリーレン基)、-NH-、-SO-、-SO2-、-CO-、-O-、-COO-、OCO-、-S-およびこれらの2以上を組み合わせてなる基が挙げられる。アルキレン基、アルキレンオキシ基におけるアルキレン基、オキシアルキレンカルボニル基におけるアルキレン基は、直鎖状、分岐状、及び、環状のいずれでもよく、直鎖状または分岐状が好ましい。また、アルキレン基、アルキレンオキシ基におけるアルキレン基、オキシアルキレンカルボニル基におけるアルキレン基は、置換基を有していてもよく、無置換であってもよい。置換基としては、ヒドロキシル基などが挙げられる。
式(A-1-3)におけるA1が表す酸基としては、カルボキシル基、スルホ基、リン酸基が挙げられる。
本発明において、硬化性化合物として用いられるエポキシ基を有する化合物(以下、エポキシ化合物ともいう)としては、1分子内にエポキシ基を2個以上有する化合物が好ましく用いられる。エポキシ化合物のエポキシ基の上限は、100個以下であることが好ましく、10個以下であることがより好ましく、5個以下であることが更に好ましい。
また、硬化性化合物として重合性化合物を用いる場合、重合性化合物の含有量は、着色組成物の全固形分中5~50質量%であることが好ましい。下限は8質量%以上であることが好ましく、10質量%以上であることがより好ましい。上限は、45質量%以下であることが好ましく、40質量%以下であることがより好ましい。
また、硬化性化合物として重合性モノマーを用いる場合、重合性モノマーの含有量は、着色組成物の全固形分中0.1~40質量%であることが好ましい。下限は1質量%以上であることが好ましく、2質量%以上であることがより好ましい。上限は、30質量%以下であることが好ましく、20質量%以下であることがより好ましい。
また、硬化性化合物として重合性樹脂を用いる場合、重合性樹脂の含有量は、着色組成物の全固形分中5~50質量%であることが好ましい。下限は8質量%以上であることが好ましく、10質量%以上であることがより好ましい。上限は、45質量%以下であることが好ましく、40質量%以下であることがより好ましい。また、重合性モノマーと重合性樹脂との合計量中における、重合性樹脂の含有量は70質量%以上であることが好ましく、80質量%以上であることがより好ましい。
また、硬化性化合物としてエポキシ化合物を用いる場合、エポキシ化合物の含有量は、着色組成物の全固形分中0.1~40質量%が好ましい。下限は、例えば1質量%以上がより好ましく、2質量%以上が更に好ましい。上限は、例えば、30質量%以下がより好ましく、20質量%以下が更に好ましい。エポキシ化合物は、1種単独であってもよいし、2種以上を併用してもよい。また、重合性化合物と、エポキシ基を有する化合物とを併用する場合、両者の割合(質量比)は、重合性化合物の質量:エポキシ基を有する化合物の質量=100:1~100:400が好ましく、100:1~100:100がより好ましく、100:1~100:50がさらに好ましい。
着色組成物が、エチレン性不飽和基を有するモノマーと、樹脂とを含み、
着色組成物に含まれるエチレン性不飽和基を有するモノマーの質量M1と、着色組成物に含まれる樹脂の質量B1との比であるM1/B1が0.3以下であり、好ましくは0.2以下である態様。この態様の着色組成物によれば、フォトリソグラフィ用の着色組成物として好ましく用いることができる。なお、樹脂の質量B1とは、上述した重合性樹脂と後述する他の樹脂との合計量である。着色組成物が、他の樹脂を含まない場合、樹脂の質量B1は、上述した重合性樹脂の質量である。また、着色組成物が、重合性樹脂を含まない場合、樹脂の質量B1は、他の樹脂の質量である。
着色組成物が、硬化性化合物としてエポキシ化合物を含む態様。この態様の着色組成物によれば、ドライエッチング用の着色組成物として好ましく用いることができる。
本発明の着色組成物は、硬化性基を含まない樹脂(以下、他の樹脂ともいう)をさらに含有することができる。他の樹脂は、例えば、顔料などの粒子を組成物中で分散させる用途やバインダーの用途で配合される。なお、主に顔料などの粒子を分散させるために用いられる樹脂を分散剤ともいう。ただし、樹脂のこのような用途は一例であって、このような用途以外の目的で樹脂を使用することもできる。
また、上述した硬化性化合物と他の樹脂との合計の含有量は、本発明の着色組成物の全固形分中10~50質量%であることが好ましい。下限は12質量%以上であることが好ましく、14質量%以上であることがより好ましい。上限は、45質量%以下であることが好ましく、40質量%以下であることがより好ましい。
本発明の着色組成物に用いられる硬化性基を有する化合物が、エチレン性不飽和基を有する化合物を含む場合、本発明の着色組成物は、更に光重合開始剤を含むことが好ましい。光重合開始剤としては、特に制限はなく、公知の光重合開始剤の中から適宜選択することができる。例えば、紫外線領域から可視領域の光線に対して感光性を有する化合物が好ましい。また、光励起された増感剤と何らかの作用を生じ、活性ラジカルを生成する化合物であってもよい。
本発明の着色組成物は、溶剤を含有することが好ましい。溶剤は有機溶剤が好ましい。溶剤は、各成分の溶解性や着色組成物の塗布性を満足すれば特に制限はない。
本発明の着色組成物は、パターンの硬度を向上させる目的や、硬化温度を下げる目的で、硬化促進剤を含んでもよい。硬化促進剤としては、チオール化合物などが挙げられる。
式(T1)
本発明の着色組成物は、顔料誘導体を含有することが好ましい。顔料誘導体としては、発色団の一部分を、酸基、塩基性基またはフタルイミドメチル基で置換した構造を有する化合物が挙げられる。
本発明の着色組成物は、界面活性剤を含有することが好ましい。界面活性剤としては、フッ素系界面活性剤、ノニオン系界面活性剤、カチオン系界面活性剤、アニオン系界面活性剤、シリコーン系界面活性剤などの各種界面活性剤を使用でき、塗布性をより向上できるという理由からフッ素系界面活性剤が好ましい。
本発明の着色組成物は、紫外線吸収剤を含有することができる。紫外線吸収剤としては、共役ジエン化合物、アミノブタジエン化合物、メチルジベンゾイル化合物、クマリン化合物、サリシレート化合物、ベンゾフェノン化合物、ベンゾトリアゾール化合物、アクリロニトリル化合物、ヒドロキシフェニルトリアジン化合物などを用いることができる。これらの詳細については、特開2012-208374号公報の段落番号0052~0072、特開2013-68814号公報の段落番号0317~0334の記載を参酌でき、これらの内容は本明細書に組み込まれる。紫外線吸収剤の具体例としては、下記構造の化合物などが挙げられる。紫外線吸収剤の市販品としては、例えば、UV-503(大東化学(株)製)などが挙げられる。また、ベンゾトリアゾール化合物としてはミヨシ油脂製のMYUAシリーズ(化学工業日報、2016年2月1日)を用いてもよい。
本発明の着色組成物は、シランカップリング剤を含有することができる。本発明において、シランカップリング剤は、加水分解性基とそれ以外の官能基とを有するシラン化合物を意味する。また、加水分解性基とは、ケイ素原子に直結し、加水分解反応および/または縮合反応によってシロキサン結合を生じ得る置換基をいう。加水分解性基としては、例えば、ハロゲン原子、アルコキシ基、アシルオキシ基などが挙げられる。
本発明の着色組成物は、重合禁止剤を含有することができる。重合禁止剤としては、ハイドロキノン、p-メトキシフェノール、ジ-t-ブチル-p-クレゾール、ピロガロール、t-ブチルカテコール、ベンゾキノン、4,4’-チオビス(3-メチル-6-t-ブチルフェノール)、2,2’-メチレンビス(4-メチル-6-t-ブチルフェノール)、N-ニトロソフェニルヒドロキシアミン塩(アンモニウム塩、第一セリウム塩等)等が挙げられる。
本発明の着色組成物が重合禁止剤を含有する場合、重合禁止剤の含有量は、着色組成物の全固形分中、0.01~5質量%が好ましい。本発明の着色組成物は、重合禁止剤を、1種類のみを含んでいてもよいし、2種類以上含んでいてもよい。2種類以上含む場合は、それらの合計量が上記範囲となることが好ましい。
本発明の着色組成物には、必要に応じて、各種添加剤、例えば、充填剤、密着促進剤、酸化防止剤、凝集防止剤等を配合することができる。これらの添加剤としては、特開2004-295116号公報の段落番号0155~0156に記載の添加剤を挙げることができ、この内容は本明細書に組み込まれる。また、酸化防止剤としては、例えばフェノール化合物、リン系化合物(例えば特開2011-90147号公報の段落番号0042に記載の化合物)、チオエーテル化合物などを用いることができる。市販品としては、例えば(株)ADEKA製のアデカスタブシリーズ(AO-20、AO-30、AO-40、AO-50、AO-50F、AO-60、AO-60G、AO-80、AO-330など)が挙げられる。酸化防止剤は1種のみを用いてもよく、2種以上を用いてもよい。本発明の着色組成物は、特開2004-295116号公報の段落番号0078に記載の増感剤や光安定剤、同公報の段落番号0081に記載の熱重合防止剤を含有することができる。
本発明の着色組成物は、前述の成分を混合して調製できる。着色組成物の調製に際しては、全成分を同時に溶剤に溶解および/または分散して着色組成物を調製してもよいし、必要に応じて、各成分を適宜2つ以上の溶液または分散液としておいて、使用時(塗布時)にこれらを混合して着色組成物を調製してもよい。
例えば、上述した範囲内で異なる孔径のフィルタを組み合わせてもよい。ここでの孔径は、フィルタメーカーの公称値を参照することができる。市販のフィルタとしては、例えば、日本ポール株式会社(DFA4201NXEYなど)、アドバンテック東洋株式会社、日本インテグリス株式会社(旧日本マイクロリス株式会社)または株式会社キッツマイクロフィルタ等が提供する各種フィルタの中から選択することができる。
また、第1のフィルタでのろ過は、分散液のみで行い、他の成分を混合した後で、第2のフィルタでろ過を行ってもよい。第2のフィルタとしては、第1のフィルタと同様の材料等で形成されたものを使用することができる。
本発明の硬化膜は、上述した本発明の着色組成物から得られる硬化膜である。硬化膜の膜厚は、目的に応じて適宜調整できる。例えば、膜厚は、20μm以下が好ましく、10μm以下がより好ましく、5μm以下がさらに好ましい。膜厚の下限は、0.1μm以上が好ましく、0.2μm以上がより好ましく、0.3μm以上がさらに好ましい。
次に、本発明のパターン形成方法について説明する。本発明のパターン形成方法は、上述した本発明の着色組成物を用いて支持体上に着色組成物層を形成する工程と、フォトリソグラフィ法またはドライエッチング法により着色組成物層に対してパターンを形成する工程と、を含む。
着色組成物層を形成する工程では、着色組成物を用いて、支持体上に着色組成物層を形成する。支持体としては、特に限定は無く、用途に応じて適宜選択できる。例えば、ガラス基板、CCDやCMOS等の固体撮像素子(受光素子)が設けられた固体撮像素子用基板、シリコン基板等が挙げられる。また、これらの基板上には、必要により、上部の層との密着改良、物質の拡散防止あるいは表面の平坦化のために下塗り層が設けられていてもよい。
<<露光工程>>
次に、着色組成物層をパターン状に露光する(露光工程)。例えば、着色組成物層に対し、ステッパー等の露光装置を用いて、所定のマスクパターンを有するマスクを介して露光することで、パターン露光することができる。これにより、露光部分を硬化することができる。露光に際して用いることができる放射線(光)としては、g線、i線等の紫外線が好ましく(特に好ましくはi線)用いられる。照射量(露光量)は、例えば、0.03~2.5J/cm2が好ましく、0.05~1.0J/cm2がより好ましい。露光時における酸素濃度については適宜選択することができ、大気下で行う他に、例えば酸素濃度が19体積%以下の低酸素雰囲気下(例えば、15体積%、5体積%、または、実質的に無酸素)で露光してもよく、酸素濃度が21体積%を超える高酸素雰囲気下(例えば、22体積%、30体積%、または、50体積%)で露光してもよい。また、露光照度は適宜設定することが可能であり、通常1000W/m2~100000W/m2(例えば、5000W/m2、15000W/m2、または、35000W/m2)の範囲から選択することができる。酸素濃度と露光照度は適宜条件を組み合わせてよく、例えば、酸素濃度10体積%で照度10000W/m2、酸素濃度35体積%で照度20000W/m2などとすることができる。
次に、着色組成物層の未露光部を現像除去してパターンを形成する。着色組成物層の未露光部の現像除去は、現像液を用いて行うことができる。これにより、露光工程における未露光部の着色組成物層が現像液に溶出し、光硬化した部分だけが残る。現像液としては、下地の固体撮像素子や回路などにダメージを起さない、有機アルカリ現像液が望ましい。現像液の温度は、例えば、20~30℃が好ましい。現像時間は、20~180秒が好ましい。また、残渣除去性を向上するため、現像液を60秒ごとに振り切り、さらに新たに現像液を供給する工程を数回繰り返してもよい。
また、硬化膜上の水の接触角は適宜好ましい値に設定することができるが、典型的には、50~110°の範囲である。接触角は、例えば接触角計CV-DT・A型(協和界面科学(株)製)を用いて測定できる。
ドライエッチング法でのパターン形成は、着色組成物を支持体上に塗布して形成した着色組成物層を硬化して硬化物層を形成し、次いで、この硬化物層上にパターニングされたレジスト層を形成し、次いで、パターニングされたレジスト層をマスクとして硬化物層に対してエッチングガスを用いてドライエッチングするなどの方法で行うことができる。レジスト層は、硬化物層上にポジ型またはネガ型の感光性組成物を塗布し、これを乾燥させて形成することが好ましい。レジスト層の形成に用いる組成物としては、ポジ型の感光性組成物が好ましい。ポジ型の感光性組成物としては、紫外線(g線、h線、i線)、KrF線、ArF線等を含む遠紫外線、電子線、イオンビームおよびX線等の放射線に感応する感光性組成物が好ましい。上述のポジ型の感光性組成物は、KrF線、ArF線、i線、X線)に感応する感光性組成物が好ましく、微細加工性の観点からKrF線に感応する感光性組成物がより好ましい。ポジ型の感光性組成物としては、特開2009-237173号公報や特開2010-134283号公報に記載のポジ型レジスト組成物が好適に用いられる。
次に、本発明のカラーフィルタについて説明する。本発明のカラーフィルタは、上述した本発明の硬化膜を有する。本発明のカラーフィルタにおいて、硬化膜の膜厚は、目的に応じて適宜調整できる。膜厚は、20μm以下が好ましく、10μm以下がより好ましく、5μm以下がさらに好ましい。膜厚の下限は、0.1μm以上が好ましく、0.2μm以上がより好ましく、0.3μm以上が更に好ましい。本発明のカラーフィルタは、CCD(電荷結合素子)やCMOS(相補型金属酸化膜半導体)などの固体撮像素子や画像表示装置などに用いることができる。
本発明の固体撮像素子は、上述した本発明の硬化膜を有する。本発明の固体撮像素子の構成としては、本発明の硬化膜を備え、固体撮像素子として機能する構成であれば特に限定はないが、例えば、以下のような構成が挙げられる。
本発明の硬化膜は、液晶表示装置や有機エレクトロルミネッセンス表示装置などの、画像表示装置に用いることができる。画像表示装置の定義や各画像表示装置の詳細については、例えば「電子ディスプレイデバイス(佐々木昭夫著、(株)工業調査会、1990年発行)」、「ディスプレイデバイス(伊吹順章著、産業図書(株)平成元年発行)」などに記載されている。また、液晶表示装置については、例えば「次世代液晶ディスプレイ技術(内田龍男編集、(株)工業調査会、1994年発行)」に記載されている。本発明が適用できる液晶表示装置に特に制限はなく、例えば、上記の「次世代液晶ディスプレイ技術」に記載されている色々な方式の液晶表示装置に適用できる。
樹脂の重量平均分子量は、以下の条件に従って、ゲルパーミエーションクロマトグラフィ(GPC)によって測定した。
カラムの種類:TOSOH TSKgel Super HZM-Hと、TOSOH TSKgel Super HZ4000と、TOSOH TSKgel Super HZ2000とを連結したカラム
展開溶媒:テトラヒドロフラン
カラム温度:40℃
流量(サンプル注入量):1.0μL(サンプル濃度0.1質量%)
装置名:東ソー(株)製 HLC-8220GPC
検出器:RI(屈折率)検出器
検量線ベース樹脂:ポリスチレン樹脂
下記の表に記載の原料を混合したのち、直径0.3mmのジルコニアビーズ230質量部を加えて、ペイントシェーカーを用いて5時間分散処理を行い、ビーズをろ過で分離して分散液を製造した。下記の表に記載の数値は質量部である。
上記で得られた分散液の粘度を、東機産業(株)製「RE-85L」にて測定後、分散液を45℃3日の条件にて静置した後、再度粘度を測定した。静置前後での粘度差(ΔVis)から下記評価基準に従って分散安定性を評価した。粘度差(ΔVis)の数値が小さいほど、分散安定性が良好であるといえる。分散液の粘度は25℃に温度調整を施した状態で測定した。
A:ΔVisが0.5以下
B:ΔVisが0.5より大きく1.0以下
C:ΔVisが1.0より大きく2.0以下
D:ΔVisが2.0より大きい
(顔料)
DPP-3、DPP-8、DPP-10、DPP-21、DPP-23、DPP-28、DPP-37、DPP-41、DPP-46、DPP-47、DPP-51、DPP-52、DPP-54、DPP-59、DPP-61、DPP-63、DPP-68、DPP-69、DPP-73、DPP-74、DPP-76:上述した顔料Aの具体例で挙げた化合物。
PR-254:C.I.ピグメントレッド254(下記構造の化合物PR-254)
PR-264:C.I.ピグメントレッド264(下記構造の化合物PR-264)
P-1:下記構造の樹脂の30質量%プロピレングリコールモノメチルエーテルアセテート(PGMEA)溶液。主鎖に付記した数値はモル比であり、側鎖に付記した数値は繰り返し単位の数である。Mw=20,000。
P-2:下記構造の樹脂の30質量%PGMEA溶液。主鎖に付記した数値はモル比であり、側鎖に付記した数値は繰り返し単位の数である。Mw=18,000。
P-3:下記構造の樹脂の30質量%PGMEA溶液。主鎖に付記した数値はモル比であり、側鎖に付記した数値は繰り返し単位の数である。Mw=22,000。
P-4:Disperbyk-111(BYKChemie社製)
P-5:下記構造の樹脂の20質量%PGMEA溶液。主鎖に付記した数値はモル比であり、側鎖に付記した数値は繰り返し単位の数である。Mw=22,900。
PGMEA:プロピレングリコールモノメチルエーテルアセテート
PGME:プロピレングリコールモノメチルエーテル
下記表に記載の原料を下記表に記載の質量部と、黄色顔料分散液Y1の12.4質量部と、界面活性剤H1の4.17質量部と、重合禁止剤(p-メトキシフェノール)の0.0006質量部と、PGMEAの7.66質量部とを混合して、着色組成物を調製した。下記表に記載の数値は質量部である。
各着色組成物をポストベーク後の膜厚が0.4μmとなるようにガラス基板上にスピンコートし、100℃、120秒間ホットプレートで乾燥した後、さらに、200℃のホットプレートを用いて300秒間加熱処理(ポストベーク)を行い、硬化膜を形成した。硬化膜が形成されたガラス基板を、紫外可視近赤外分光光度計U-4100((株)日立ハイテクノロジーズ製)(ref.ガラス基板)を用いて、波長300~1000nmの範囲における光の透過率を測定した。分光評価は波長580nmの透過率を測定して評価した。波長580nmの透過率が低いほど赤色の着色層としての分光特性に優れている。
実施例1~38の着色組成物をポストベーク後の膜厚が0.4μmとなるように8インチ(20.32cm)のシリコンウエハ基板にスピンコートし、100℃、120秒間ホットプレートで乾燥して着色組成物層を得た。
この着色組成物層に対して、i線ステッパーFPA-3000i5+(Canon(株)製)を使用し、一辺1.1μmの正方ピクセルがそれぞれ基板上の4mm×3mmの領域に配列されたマスクパターンを介し、365nmの波長の光を照射し、露光量500mJ/cm2にて露光を行った。
露光後の着色組成物層に対し、テトラメチルアンモニウムハイドロオキサイドの0.3質量%水溶液を用い、23℃で60秒間パドル現像を行った。その後、スピンシャワーにて水を用いてリンスを行った。その後、水滴を高圧のエアーで飛ばし、シリコンウエハを自然乾燥させたのち、ホットプレートを用いて220℃で300秒間ポストベークを行い、パターンを形成した。
分散液3、分散液6、分散液10、分散液12、分散液14、分散液16、分散液18、分散液20、分散液24、分散液26、分散液34、分散液37、分散液41、分散液43、分散液45、分散液47、分散液49、分散液51、分散液55、分散液57、分散液65、分散液68、分散液72、分散液74、分散液76、分散液78、分散液80、分散液81、分散液83、分散液85、分散液89、分散液91、分散液97、分散液98、分散液99、分散液100、分散液101、分散液102、分散液104、分散液105、分散液107、分散液109、分散液113:それぞれ上述した分散液
以下の方法で調製した黄色顔料分散液Y1。
C.Iピグメントイエロー139の10.81質量部と、上述した誘導体-1の1.5質量部と、分散剤P-6(下記構造の樹脂)の3.78質量部と、PEGMAの83.87質量部とを混合したのち、直径0.3mmのジルコニアビーズ230質量部を加えて、ペイントシェーカーを用いて5時間分散処理を行い、ビーズをろ過で分離して黄色顔料分散液Y1を製造した。
・分散剤P-6:下記構造の樹脂の30質量%PGMEA溶液。主鎖に付記した数値はモル比であり、側鎖に付記した数値は繰り返し単位の数である。Mw=24,000。
D1:下記構造の樹脂の40質量%PGMEA溶液。主鎖に付記した数値はモル比である。Mw=11,000。
D2:下記構造の樹脂の40質量%PGMEA溶液。主鎖に付記した数値はモル比である。Mw=14,000。
E1:KAYARAD DPHA(日本化薬(株)製)
E2:アロニックス M-305(東亞合成(株)製)
E3:NKエステル A-TMMT(新中村化学工業(株)製)
E4:KAYARAD RP-1040(日本化薬(株)製)
E5:アロニックスTO-2349(東亞合成(株)製)
F1:IRGACURE-OXE01(BASF製)
F2:IRGACURE-OXE02(BASF製)
F3:下記構造の化合物
F5:下記構造の化合物
赤色顔料分散液として上記の分散液14の70.8質量部と、黄色顔料分散液Y1の18.9質量部と、エポキシ化合物EP1の2.6質量部と、界面活性剤H2の2.7質量部と、PGMEAの50質量部とを混合して着色組成物101を調製した。
(エポキシ化合物)
EP1:2,2-ビス(ヒドロキシメチル)-1-ブタノールの1,2-エポキシ-4-(2-オキシラニル)シクロへキサン付加物((株)ダイセル製、EHPE3150、Mw23000)
(界面活性剤)
H2:下記混合物(Mw=14000)の0.2質量%シクロヘキサノン溶液。下記の式中、繰り返し単位の割合を示す%はモル%である。
得られた着色組成物101をポストベーク後の膜厚が0.4μmとなるようにガラス基板上にスピンコートし、100℃、120秒間ホットプレートで乾燥した後、さらに、200℃のホットプレートを用いて300秒間加熱処理(ポストベーク)を行い、硬化膜を形成した。硬化膜が形成されたガラス基板を、紫外可視近赤外分光光度計U-4100((株)日立ハイテクノロジーズ製)(ref.ガラス基板)を用いて、波長300~1000nmの範囲における光の透過率を測定した。波長580nmの透過率は10%であった。
着色組成物101をポストベーク後の膜厚が0.4μmとなるように8インチ(20.32cm)のシリコンウエハ基板上にスピンコートし、100℃、120秒間ホットプレートで乾燥した後、さらに、200℃のホットプレートを用いて300秒間加熱処理(ポストベーク)を行い、着色層を形成した。
次いで、着色層上に、ポジ型フォトレジスト(FHi622BC、富士フイルムエレクトロニクスマテリアルズ社製)を塗布し、100℃、120秒間ホットプレートで乾燥して膜厚0.8μmのフォトレジスト層を形成した。
次いで、フォトレジスト層の温度が90℃となる温度で1分間、加熱処理を行なった。その後、現像液(FHD-5、富士フイルムエレクトロニクスマテリアルズ社製)を用いて1分間の現像処理を行なったのち、110℃で1分間ポストベークを行いマスクを形成した。
次に、ドライエッチングを以下の手順で行った。
ドライエッチング装置((株)日立ハイテクノロジーズ製、U-621)にて、RF(高周波)パワー:800W、アンテナバイアス:400W、ウエハバイアス:200W、チャンバーの内部圧力:4.0Pa、基板温度:50℃、混合ガスのガス種及び流量:CF4=80mL/min、O2=40mL/min、Ar=800mL/minの条件で第1段階のエッチング処理を80秒間実施した。
次いで、同一のドライエッチング装置にて、RFパワー:600W、アンテナバイアス:100W、ウエハバイアス:250W、チャンバーの内部圧力:2.0Pa、基板温度:50℃、混合ガスのガス種及び流量:N2=500mL/min、O2=50mL/min、Ar=500mL/min(N2/O2/Ar=10/1/10(流量比))の条件で、第2段階エッチング処理を28秒間行った。
上記条件でドライエッチングを行った後、フォトレジスト剥離液(MS230C、富士フイルムエレクトロニクスマテリアルズ社製)を使用して120秒間、剥離処理を実施してレジストを除去し、更に純水による洗浄、スピン乾燥を実施した。その後、100℃で2分間の脱水ベーク処理を行った。以上により、パターンを形成した。この着色組成物は、ドライエッチング法でのパターン形成性が良好であった。
Claims (13)
- 芳香族環に対して、酸素原子、硫黄原子または窒素原子が結合した基が導入された芳香族環基がジケトピロロピロール骨格に結合した構造を有する顔料Aと、
硬化性基を有する化合物と、を含む着色組成物であって、
前記着色組成物の全固形分中における前記顔料Aの含有量が40質量%以上である、着色組成物。 - 前記硬化性基を有する化合物は、エチレン性不飽和基を有する化合物およびエポキシ基を有する化合物から選ばれる少なくとも1種を含む、請求項1~4のいずれか1項に記載の着色組成物。
- 前記硬化性基を有する化合物は、エチレン性不飽和基を有する樹脂を含む、請求項1~5のいずれか1項に記載の着色組成物。
- 前記硬化性基を有する化合物は、エチレン性不飽和基を有する化合物を含み、かつ、更に光重合開始剤を含む、請求項1~6のいずれか1項に記載の着色組成物。
- 前記着色組成物は、エチレン性不飽和基を有するモノマーと、樹脂とを含み、
前記着色組成物に含まれる前記エチレン性不飽和基を有するモノマーの質量M1と、前記着色組成物に含まれる前記樹脂の質量B1との比であるM1/B1が0.2以下である、請求項1~7のいずれか1項に記載の着色組成物。 - 請求項1~8のいずれか1項に記載の着色組成物から得られる硬化膜。
- 請求項1~8のいずれか1項に記載の着色組成物を用いて支持体上に着色組成物層を形成する工程と、フォトリソグラフィ法またはドライエッチング法により着色組成物層に対してパターンを形成する工程と、を有するパターン形成方法。
- 請求項9に記載の硬化膜を有するカラーフィルタ。
- 請求項9に記載の硬化膜を有する固体撮像素子。
- 請求項9に記載の硬化膜を有する画像表示装置。
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2019172006A1 (ja) * | 2018-03-05 | 2019-09-12 | 富士フイルム株式会社 | 感光性組成物 |
WO2020040043A1 (ja) * | 2018-08-22 | 2020-02-27 | 富士フイルム株式会社 | 着色組成物、硬化膜、パターン形成方法、カラーフィルタ、固体撮像素子および画像表示装置 |
WO2020184244A1 (ja) * | 2019-03-11 | 2020-09-17 | 富士フイルム株式会社 | 着色組成物、硬化膜、パターン形成方法、カラーフィルタ、固体撮像素子および画像表示装置 |
CN112782933A (zh) * | 2019-11-06 | 2021-05-11 | 东友精细化工有限公司 | 着色感光性树脂组合物、滤色器及图像显示装置 |
JPWO2021172142A1 (ja) * | 2020-02-26 | 2021-09-02 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005039515A1 (en) * | 2003-10-17 | 2005-05-06 | Ciba Specialty Chemicals Holding Inc. | Cosmetic formulations comprising diketo diphenyl pyrrolo-pyrrole pigments |
JP2011523433A (ja) * | 2008-05-28 | 2011-08-11 | ビーエーエスエフ ソシエタス・ヨーロピア | 改良された赤色フィルター組成物 |
JP2013161026A (ja) * | 2012-02-08 | 2013-08-19 | Toyo Ink Sc Holdings Co Ltd | カラーフィルタ用着色剤組成物およびカラーフィルタ |
JP2013186146A (ja) * | 2012-03-06 | 2013-09-19 | Toyo Ink Sc Holdings Co Ltd | カラーフィルタ用着色組成物およびカラーフィルタ |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0061426B1 (de) * | 1981-03-20 | 1985-02-13 | Ciba-Geigy Ag | Verfahren zum Färben von hochmolekularem organischem Material und neue polycyclische Pigmente |
US7977670B2 (en) | 2006-10-12 | 2011-07-12 | Toyo Ink Mfg. Co., Ltd. | Organic transistor |
JP5258280B2 (ja) * | 2007-12-18 | 2013-08-07 | 富士フイルム株式会社 | 顔料分散組成物、感光性樹脂組成物、カラーフィルタおよびその製造方法 |
JP5557073B2 (ja) | 2008-08-01 | 2014-07-23 | 大日本印刷株式会社 | 着色組成物およびカラーフィルタ |
JP5575825B2 (ja) * | 2011-03-17 | 2014-08-20 | 富士フイルム株式会社 | 着色感放射線性組成物、着色硬化膜、カラーフィルタ及びカラーフィルタの製造方法、固体撮像素子、液晶表示装置、並びに、染料の製造方法 |
-
2018
- 2018-09-13 WO PCT/JP2018/033896 patent/WO2019059075A1/ja active Application Filing
- 2018-09-13 KR KR1020207007732A patent/KR102292981B1/ko active IP Right Grant
- 2018-09-13 JP JP2019543590A patent/JP6892927B2/ja active Active
- 2018-09-17 TW TW107132683A patent/TWI740063B/zh active
-
2020
- 2020-03-17 US US16/821,057 patent/US11390752B2/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005039515A1 (en) * | 2003-10-17 | 2005-05-06 | Ciba Specialty Chemicals Holding Inc. | Cosmetic formulations comprising diketo diphenyl pyrrolo-pyrrole pigments |
JP2011523433A (ja) * | 2008-05-28 | 2011-08-11 | ビーエーエスエフ ソシエタス・ヨーロピア | 改良された赤色フィルター組成物 |
JP2013161026A (ja) * | 2012-02-08 | 2013-08-19 | Toyo Ink Sc Holdings Co Ltd | カラーフィルタ用着色剤組成物およびカラーフィルタ |
JP2013186146A (ja) * | 2012-03-06 | 2013-09-19 | Toyo Ink Sc Holdings Co Ltd | カラーフィルタ用着色組成物およびカラーフィルタ |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2019172006A1 (ja) * | 2018-03-05 | 2019-09-12 | 富士フイルム株式会社 | 感光性組成物 |
US11953831B2 (en) | 2018-03-05 | 2024-04-09 | Fujifilm Corporation | Photosensitive composition |
WO2020040043A1 (ja) * | 2018-08-22 | 2020-02-27 | 富士フイルム株式会社 | 着色組成物、硬化膜、パターン形成方法、カラーフィルタ、固体撮像素子および画像表示装置 |
WO2020184244A1 (ja) * | 2019-03-11 | 2020-09-17 | 富士フイルム株式会社 | 着色組成物、硬化膜、パターン形成方法、カラーフィルタ、固体撮像素子および画像表示装置 |
CN112782933A (zh) * | 2019-11-06 | 2021-05-11 | 东友精细化工有限公司 | 着色感光性树脂组合物、滤色器及图像显示装置 |
CN112782933B (zh) * | 2019-11-06 | 2024-04-02 | 东友精细化工有限公司 | 着色感光性树脂组合物、滤色器及图像显示装置 |
JPWO2021172142A1 (ja) * | 2020-02-26 | 2021-09-02 |
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JPWO2019059075A1 (ja) | 2020-11-05 |
JP6892927B2 (ja) | 2021-06-23 |
KR20200041955A (ko) | 2020-04-22 |
KR102292981B1 (ko) | 2021-08-24 |
US11390752B2 (en) | 2022-07-19 |
US20200239694A1 (en) | 2020-07-30 |
TWI740063B (zh) | 2021-09-21 |
TW201915105A (zh) | 2019-04-16 |
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