WO2018061384A1 - 感光性樹脂組成物、導電性パターンの製造方法、基板、タッチパネル及びディスプレイ - Google Patents
感光性樹脂組成物、導電性パターンの製造方法、基板、タッチパネル及びディスプレイ Download PDFInfo
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- WO2018061384A1 WO2018061384A1 PCT/JP2017/024787 JP2017024787W WO2018061384A1 WO 2018061384 A1 WO2018061384 A1 WO 2018061384A1 JP 2017024787 W JP2017024787 W JP 2017024787W WO 2018061384 A1 WO2018061384 A1 WO 2018061384A1
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- Prior art keywords
- meth
- resin composition
- photosensitive resin
- substrate
- acrylate
- Prior art date
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- 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
- G03F7/0042—Photosensitive materials with inorganic or organometallic light-sensitive compounds not otherwise provided for, e.g. inorganic resists
- G03F7/0043—Chalcogenides; Silicon, germanium, arsenic or derivatives thereof; Metals, oxides or alloys thereof
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- G03F7/004—Photosensitive materials
- G03F7/0047—Photosensitive materials characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing
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- 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
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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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
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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
- G03F7/20—Exposure; Apparatus therefor
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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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
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- G—PHYSICS
- G06—COMPUTING; CALCULATING OR COUNTING
- G06F—ELECTRIC DIGITAL DATA PROCESSING
- G06F3/00—Input arrangements for transferring data to be processed into a form capable of being handled by the computer; Output arrangements for transferring data from processing unit to output unit, e.g. interface arrangements
- G06F3/01—Input arrangements or combined input and output arrangements for interaction between user and computer
- G06F3/03—Arrangements for converting the position or the displacement of a member into a coded form
- G06F3/041—Digitisers, e.g. for touch screens or touch pads, characterised by the transducing means
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/20—Conductive material dispersed in non-conductive organic material
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/20—Conductive material dispersed in non-conductive organic material
- H01B1/22—Conductive material dispersed in non-conductive organic material the conductive material comprising metals or alloys
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B13/00—Apparatus or processes specially adapted for manufacturing conductors or cables
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B13/00—Apparatus or processes specially adapted for manufacturing conductors or cables
- H01B13/0036—Details
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B5/00—Non-insulated conductors or conductive bodies characterised by their form
- H01B5/14—Non-insulated conductors or conductive bodies characterised by their form comprising conductive layers or films on insulating-supports
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices 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; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/02—Details
- H01L31/0224—Electrodes
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/02—Details
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/09—Use of materials for the conductive, e.g. metallic pattern
- H05K1/092—Dispersed materials, e.g. conductive pastes or inks
- H05K1/095—Dispersed materials, e.g. conductive pastes or inks for polymer thick films, i.e. having a permanent organic polymeric binder
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- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/02—Apparatus or processes for manufacturing printed circuits in which the conductive material is applied to the surface of the insulating support and is thereafter removed from such areas of the surface which are not intended for current conducting or shielding
- H05K3/027—Apparatus or processes for manufacturing printed circuits in which the conductive material is applied to the surface of the insulating support and is thereafter removed from such areas of the surface which are not intended for current conducting or shielding the conductive material being removed by irradiation, e.g. by photons, alpha or beta particles
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- 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
- H01L27/14601—Structural or functional details thereof
- H01L27/14636—Interconnect structures
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- 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
- H01L27/14683—Processes or apparatus peculiar to the manufacture or treatment of these devices or parts thereof
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices 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; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/02—Details
- H01L31/0224—Electrodes
- H01L31/022408—Electrodes for devices characterised by at least one potential jump barrier or surface barrier
- H01L31/022425—Electrodes for devices characterised by at least one potential jump barrier or surface barrier for solar cells
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
- H05K2201/01—Dielectrics
- H05K2201/0137—Materials
- H05K2201/0154—Polyimide
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
- H05K2201/02—Fillers; Particles; Fibers; Reinforcement materials
- H05K2201/0203—Fillers and particles
- H05K2201/0206—Materials
- H05K2201/0224—Conductive particles having an insulating coating
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/621—Providing a shape to conductive layers, e.g. patterning or selective deposition
Definitions
- the present invention relates to a photosensitive resin composition, a method for producing a conductive pattern, a substrate, a touch panel, and a display.
- the demand for miniaturization of electronic wiring has increased with the increase in the definition of displays and the miniaturization or increase in density of electronic components.
- a method for producing a conductive pattern used for electronic wiring by using a resin composition containing conductive particles the conductive particles are brought into contact by heating after forming the pattern on the substrate.
- a method for obtaining a pattern is common.
- the method for forming a pattern on the substrate include a screen printing method, an ink jet method, and a photolithography method. Among them, the screen printing method and the ink jet method are not suitable for forming a fine pattern, and the photolithography method is suitable for forming the fine pattern.
- an exposed portion and an unexposed portion are formed on the coating film by irradiating ultraviolet rays or the like through a photomask on which the shape of a fine wiring pattern is drawn after application and drying of the photosensitive composition.
- a photomask on which the shape of a fine wiring pattern is drawn after application and drying of the photosensitive composition.
- it is developed with a developer to form a fine pattern on the substrate.
- a method of forming a fine electroconductive pattern by subsequent electroconductivity processing is composed of conductive particles, a photosensitive agent, a resin, and the like (Patent Documents 1 to 4).
- the present invention was devised in view of the drawbacks of the related art, and the object is to achieve both fine pattern resolution and residue suppression on a substrate even on a film containing an organic component. It is in providing the photosensitive resin composition which can be carried out. By using such a photosensitive resin composition, a fine conductive pattern having a very good appearance and high reliability can be obtained.
- the present invention relates to a photosensitive resin comprising conductive particles (A) whose surface is coated with a carbon simple substance and / or a carbon compound, an alkali-soluble resin (B) having an acid dissociable group, and a metal chelate compound (C).
- a composition is provided.
- the photosensitive resin composition of the present invention it is possible to obtain a fine conductive pattern having a good appearance and high reliability.
- the photosensitive resin composition of the present invention comprises conductive particles (A) surface-coated with a carbon simple substance and / or a carbon compound, an alkali-soluble resin (B) having an acid dissociable group, and a metal chelate compound (C). It is characterized by containing.
- the photosensitivity in the photosensitive resin composition may be positive photosensitivity or negative photosensitivity, but is preferably negative photosensitivity.
- the conductive particles (A) whose surface is coated with a carbon simple substance and / or a carbon compound have a surface coating layer (hereinafter referred to as “surface coating layer”), so that the conductive particles are melted at a low temperature. Wear can be suppressed.
- a method of coating the particle surface with a carbon simple substance and / or a carbon compound for example, a method of contacting a reactive gas when producing conductive particles by a thermal plasma method (Japanese Patent Application Laid-Open No. 2007-138287). Can be mentioned.
- the surface of the conductive particles is preferably completely covered. However, as long as this object is achieved, the presence of partially incompletely covered particles is allowed.
- Examples of the conductive particles (A) whose surface is coated with a carbon simple substance and / or a carbon compound include gold (Au), silver (Ag), copper (Cu), nickel (Ni), tin (Sn), and bismuth.
- Examples thereof include fine metal particles such as (Bi), lead (Pb), zinc (Zn), palladium (Pd), platinum (Pt), aluminum (Al), tungsten (W), and molybdenum (Mo).
- metal fine particles containing at least one element selected from the group consisting of gold, silver, copper, nickel, tin, bismuth, lead, zinc, palladium, platinum, aluminum and carbon are preferable. More preferably.
- the primary particle diameter of the conductive particles (A) whose surface is coated with a carbon simple substance and / or a carbon compound is preferably 1 to 700 nm in order to form a fine conductive pattern having desired conductivity.
- the primary particle size of the conductive particles (A) whose surface is coated with a carbon simple substance and / or a carbon compound is the particle size of 100 primary particles randomly selected using a scanning electron microscope. The average value can be calculated. The particle diameter of each primary particle can be calculated from the average value obtained by measuring the major and minor diameters of the primary particles.
- the primary particle diameter of the conductive particles (A) whose surface is coated with a carbon simple substance and / or a carbon compound is preferably 10 to 200 nm, and more preferably 10 to 60 nm.
- the average thickness of the surface coating layer is preferably 0.1 to 10 nm. Within this range, the fine pattern processability can be improved by suppressing the fusion of the conductive fine particles, and desired conductivity can be exhibited by heat treatment at a temperature of 300 ° C. or lower.
- the average thickness of the surface coating layer is determined by measuring the mass loss due to the thermobalance of the conductive particles (A) surface-coated with the carbon simple substance and / or the carbon compound, and assuming that all the values are due to carbon combustion.
- the average thickness of the surface coating layer can be calculated from the particle diameter, assuming that the carbon density is 2.0. It is assumed that carbon is coated with an average thickness A ( ⁇ m) on conductive particles whose particle diameter (Dp) is known. Let n be the number of particles coated with carbon.
- the content of the carbon simple substance and / or the conductive particles (A) surface-coated with the carbon compound in the photosensitive resin composition is preferably 65 to 95% by mass, and preferably 70 to 95% by mass. More preferred is 70 to 90% by mass.
- the total solid content means all components excluding the solvent among the components contained in the photosensitive resin composition.
- the proportion of the carbon particles and / or the conductive particles (A) whose surface is coated with a carbon compound in the total solid content can be calculated by quantitatively analyzing all the components of the photosensitive resin composition. In addition, the ratio of each component mentioned later can be calculated by the same method.
- the method for analyzing all components of the photosensitive resin composition is as follows.
- the photosensitive resin composition is diluted with an organic solvent, and its outline is examined by 1 H-NMR measurement, GC measurement, and GC / MS measurement.
- the photosensitive resin composition is extracted with an organic solvent and then centrifuged to separate soluble and insoluble components.
- the insoluble matter is extracted with a highly polar organic solvent and then centrifuged to further separate the soluble and insoluble matters.
- IIv Perform IR measurement, 1 H-NMR measurement and GC / MS measurement on the mixture of the soluble components obtained in (ii) and (iii) above. Further, the above mixed solution is collected by GPC.
- the obtained fraction is subjected to IR measurement and 1 H-NMR measurement. Moreover, about this fraction, GC measurement, GC / MS measurement, pyrolysis GC / MS measurement, and MALDI / MS measurement are performed as needed.
- V Perform IR measurement or TOF-SIMS measurement on the insoluble matter obtained in (iii) above. When it is confirmed that organic substances are present, pyrolysis GC / MS or TPD / MS measurement is performed.
- Vi By comprehensively determining the measurement results of (i), (iv) and (v) above, the content of each component contained in the photosensitive resin composition can be determined. In addition, as a highly polar organic solvent used by said (iii), chloroform or methanol is preferable.
- Alkali-soluble resin having acid-dissociable group (B) By including an acid-dissociable group in the alkali-soluble resin, the acid-dissociable group is desorbed and vaporized by heat treatment after pattern formation, and the pattern shrinks. Thereby, it is possible to promote contact between the conductive particles (A) whose surfaces are covered with a carbon simple substance and / or a carbon compound, improve conductivity, and form a fine pattern.
- the alkali-soluble resin (B) having an acid dissociable group is generally obtained by copolymerizing a compound having a carboxyl group, a compound having an acid dissociable group, and another monomer.
- the alkali-soluble resin (B) having an acid dissociable group is preferably a (meth) acrylic copolymer.
- the (meth) acrylic copolymer refers to a copolymer containing at least a (meth) acrylic monomer as a copolymerization component.
- the (meth) acrylic monomer include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, and sec-butyl.
- a compound having a carbon-carbon double bond can be used as the copolymerization component other than the (meth) acrylic monomer.
- examples of such compounds include aromatic vinyl compounds such as styrene, p-methylstyrene, o-methylstyrene, m-methylstyrene, and ⁇ -methylstyrene, (meth) acrylamide, N-methylol (meth) acrylamide, or Amide unsaturated compounds such as N-vinylpyrrolidone, (meth) acrylonitrile, allyl alcohol, vinyl acetate, cyclohexyl vinyl ether, n-propyl vinyl ether, i-propyl vinyl ether, n-butyl vinyl ether, i-butyl vinyl ether, 2-hydroxyethyl Examples include vinyl ether or 4-hydroxybutyl vinyl ether.
- Examples of the compound containing a carboxyl group that is a copolymerization component that imparts alkali solubility to the alkali-soluble resin (B) having an acid-dissociable group include (meth) acrylic acid, itaconic acid, crotonic acid, maleic acid, and fumaric acid. An acid or these acid anhydrides are mentioned.
- a (meth) acrylic copolymer in order to increase the speed of the curing reaction by exposure of the photosensitive resin composition, a (meth) acrylic compound having a carbon-carbon double bond in the side chain or molecular end It is preferable to use a copolymer.
- the functional group having a carbon-carbon double bond include a vinyl group, an allyl group, and a (meth) acryl group.
- Examples of the compound having a glycidyl group and a carbon-carbon double bond include glycidyl (meth) acrylate, allyl glycidyl ether or glycidyl ethyl acrylate, crotonyl glycidyl ether, glycidyl crotonate or glycidyl isocrotonate.
- Examples of the compound having an isocyanate group and a carbon-carbon double bond include (meth) acryloyl isocyanate or (meth) acryloyloxyethyl isocyanate.
- Examples of the compound having an acid dissociable group include (meth) acrylic acid esters having an acid dissociable group.
- the acid dissociable group is preferably an organic group having 4 to 15 carbon atoms, more preferably an organic group having 6 to 15 carbon atoms.
- the number of carbon atoms of the acid dissociable group is less than 4, the gas is vaporized at a low temperature after desorption, so that large bubbles are generated in the film, and the conductive particles whose surface is covered with a carbon simple substance and / or a carbon compound ( A) Contact with each other may be hindered and conductivity may deteriorate.
- the conductive particles (A) having the dissociable group remaining in the film after desorption and having a surface coated with a carbon simple substance and / or a carbon compound are bonded together. May also interfere with the contact, and the conductivity may also deteriorate.
- the acid-dissociable group of the acid-dissociable group is an organic group having 6 to 15 carbon atoms, even if bubbles are generated in the film, they can be easily eliminated by post-baking and have good conductivity. A conductive pattern can be formed.
- Examples of the acid dissociable group include a tert-butyl group, a tert-butoxycarbonyl group, a benzyl group, a methyladamantyl group, and a tetrahydropyranyl group.
- Examples of the (meth) acrylic acid ester having an acid dissociable group include 1-methyladamantyl (meth) acrylate, tert-butyl (meth) acrylate, benzyl (meth) acrylate or tetrahydropyrani (meth) acrylate. Le.
- the content of the alkali-soluble resin (B) having an acid dissociable group is in the range of 5 to 30% by mass with respect to the total solid content in consideration of the expression of photosensitivity. It is preferable.
- the alkali-soluble resin (B) having an acid-dissociable group is preferably an alkali-soluble resin obtained by radical copolymerization of a compound having an acid-dissociable group with 20 to 80 mol%.
- (meth) acrylic acid ester having an acid dissociable group is preferably contained in an alkali-soluble resin as a monomer component in an amount of 20 to 80 mol%.
- concentration of the electroconductive particle (A) surface-coated with the carbon simple substance in the inside and / or a carbon compound can be raised easily.
- concentration of the electroconductive particle (A) surface-coated with the carbon simple substance in the inside and / or a carbon compound can be raised easily.
- a thermal acid generator and / or a photoacid generator described later are used in combination, the effect becomes more remarkable.
- the carboxylic acid equivalent of the alkali-soluble resin (B) having an acid dissociable group is preferably 200 to 1,400 g / mol, more preferably 400 to 1,000 g / mol.
- the carboxylic acid equivalent of the acrylic resin can be calculated by measuring the acid value.
- the double bond equivalent of the alkali-soluble resin (B) having an acid dissociable group is preferably 150 to 10,000 g / mol because both hardness and crack resistance can be achieved at a high level.
- the double bond equivalent of the acrylic resin can be calculated by measuring the iodine value.
- the weight average molecular weight (Mw) of the alkali-soluble resin (B) having an acid-dissociable group is preferably 1,000 to 100,000 in terms of polystyrene measured by gel permeation chromatography (GPC).
- GPC gel permeation chromatography
- Metal chelate compound (C) is a compound having a central metal and a ligand coordinated to the central metal at two or more sites, and the ligand is easily detached and an alkali-soluble functional group. And complex formation is possible. By complexing with an alkali-soluble resin, the developability of the resin component can be controlled, and the effect of suppressing pattern peeling becomes remarkable.
- Examples of the metal element of the metal chelate compound (C) include Au (gold), Ag (silver), Cu (copper), Cr (chromium), Fe (iron), Co (cobalt), Ni (nickel), and Bi. (Bismuth), Sn (tin), Pb (lead), Zn (zinc), Pd (palladium), In (indium), Pt (platinum), Mg (magnesium), Al (aluminum), Ti (titanium), Zr (Zirconium), W (tungsten), and Mo (molybdenum).
- Mg magnesium
- Al aluminum
- Ti titanium
- Zr zirconium
- Bi bismuth
- Al aluminum
- Zr zirconium
- Bi bismuth
- the metal chelate compound (C) can be easily obtained by reacting a metal alkoxide with a chelating agent.
- the chelating agent examples include ⁇ -diketones such as acetylacetone, benzoylacetone or dibenzoylmethane, or ⁇ -ketoesters such as ethyl acetoacetate or ethyl benzoylacetate.
- Examples of the metal chelate compound (C) include bis (acetylacetonate) magnesium, bis (ethylacetoacetate) magnesium, isopropoxymono (acetylacetonate) magnesium, and isopropoxymono (ethylacetoacetate) magnesium.
- Aluminum chelate compounds such as magnesium chelate compounds, ethyl acetoacetate aluminum diisopropylate, aluminum trisethyl acetoacetate, alkyl acetoacetate aluminum diisopropylate, aluminum monoacetylacetonate bis (ethylacetoacetate), aluminum tris (acetylacetonate) , Tetrakis (acetylacetonate) titanium, diisopropoxybis (ethylacetoacetate) Tan, diisopropoxybis (acetylacetonato) titanium, di-n-octyloxybis (octylene glycolate) titanium, diisopropoxybis (triethanolaminato) titanium, dihydroxybis (2-hydroxypropionate) titanium Titanium chelate compounds such as dihydroxybis (2-hydroxypropionate) titanium ammonium salt, zirconium tetracetyl acetonate, zirconium dibutoxy bis (ethyl acetoacetate), zi
- Zirconium chelate compounds gold chelate compounds such as bis (acetylacetonato) gold or bis (ethylacetoacetate) gold, bis (acetylacetonate) )
- Silver chelate compounds such as silver or bis (ethylacetoacetate) silver
- copper chelate compounds such as bis (acetylacetonate) copper or bis (ethylacetoacetate) copper
- bis (acetylacetonate) chromium or bis (ethyl) Chromium chelate compounds such as acetoacetate) chromium
- iron chelate compounds such as bis (acetylacetonate) iron or bis (ethylacetoacetate) iron, bis (acetylacetonate) cobalt or bis (ethylacetoacetate) cobalt Cobalt chelate compounds
- nickel chelate compounds such as bis (acetylacetonato) nickel or bis (ethylacetoacetate) nickel, bis (acet
- Examples of the metal chelate compound (C) include a compound represented by the general formula (1).
- R 1 represents magnesium, aluminum, titanium, zirconium or bismuth
- R 1 represents hydrogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 4 to 10 carbon atoms, or an aryl group having 6 to 15 carbon atoms
- R 2 and R 3 each independently represent hydrogen, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 4 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, or an alkyl group having 1 to 6 carbon atoms.
- R 1 is preferably hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 4 to 7 carbon atoms, or an aryl group having 6 to 10 carbon atoms
- R 2 and R 3 are each independently hydrogen
- An alkyl group having 1 to 18 carbon atoms, a cycloalkyl group having 4 to 7 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a hydroxy group is preferable.
- the alkyl group, cycloalkyl group, aryl group, and alkoxy group may be either unsubstituted or substituted.
- M is preferably aluminum, zirconium or bismuth.
- Examples of the compound represented by the general formula (1) include bis (acetylacetonate) magnesium, bis (ethylacetoacetate) magnesium, isopropoxymono (acetylacetonate) magnesium, and isopropoxymono (ethylacetoacetate).
- Magnesium chelate compounds such as magnesium, ethyl acetoacetate aluminum diisopropylate, aluminum trisethyl acetoacetate, alkyl acetoacetate aluminum diisopropylate, aluminum monoacetylacetonate bis (ethylacetoacetate), aluminum tris (acetylacetonate), etc.
- Aluminum chelate compounds tetrakis (acetylacetonato) titanium, diisopropoxybis (ethylacetoacetator) ) Titanium, diisopropoxybis (acetylacetonate) titanium, di-n-octyloxybis (octylene glycolate) titanium, diisopropoxybis (triethanolaminato) titanium, dihydroxybis (2-hydroxypropionate) titanium Or titanium chelate compounds such as dihydroxybis (2-hydroxypropionate) titanium ammonium salt, zirconium tetracetylacetonate, zirconium dibutoxybis (ethylacetoacetate), zirconium tributoxymonoacetylacetonate, zirconium tributoxymonostearate Zirconium chelate compounds such as bis (acetylacetonato) bismuth or bis (ethylacetoacetate) bismuth It is.
- the ratio of the metal chelate compound (C) in the total solid content is preferably 0.01 to 10% by mass, more preferably 0.05 to 5% by mass, and 0.1 to 5% by mass. More preferably it is.
- the content of the metal chelate compound (C) is 0.01% by mass or more, the effect of suppressing residues on the substrate becomes even more remarkable.
- the content of the metal chelate compound (C) is 10% by mass or less, the conductivity is high and a fine pattern can be formed.
- the photosensitive resin composition of the present invention may contain a dispersant.
- a dispersing agent By containing a dispersing agent, the electroconductive particle (A) surface-coated with the carbon simple substance and / or a carbon compound can be made to exist stably in the photosensitive resin composition.
- the dispersant is preferably an amine-based one.
- examples of commercially available amine-based dispersants include DISPERBYK (registered trademark) 106, 108, 112, 116, 142, 145, 166, 180, 2001, 2008, 2022, 2150, 6919, or 21116 (all of which are Big Chemie). (Made by Japan) or Efka (registered trademark) 4300, 4400, 4401, 4403, 4406, 4510, 4570, 4800, 5054, 5055, or 5207 (all are made by BASF).
- the dispersant preferably has an acrylic block copolymer structure.
- acrylic block copolymer structure examples include DISPERBYK (registered trademark) 2001, 2008, 2022, 2150, 6919, or 21116, or Efka (registered trademark) 4300.
- content of the dispersing agent in the photosensitive resin composition it is 1 with respect to 100 mass parts in total of the electroconductive particle (A) surface-coated with the carbon simple substance and / or a carbon compound, and the other particle
- the photosensitive resin composition of the present invention may contain a photopolymerization initiator. By containing a photopolymerization initiator, negative photosensitivity can be imparted to the photosensitive resin composition.
- Examples of the photopolymerization initiator include acetophenone compounds, benzophenone compounds, benzoin ether compounds, ⁇ -aminoalkylphenone compounds, thioxanthone compounds, organic peroxides, imidazole compounds, titanocene compounds, and triazine compounds. , Acylphosphine oxide compounds, quinone compounds or oxime ester compounds. An oxime ester compound having high sensitivity even when added in a small amount is preferable, and an oxime ester compound having a carbazole skeleton is more preferable.
- Examples of the oxime ester compound having no carbazole skeleton include Irgacure (registered trademark) OXE01 (manufactured by BASF), and examples of the oxime ester compound having a carbazole skeleton include Irgacure (registered trademark) OXE02 ( BASF), Adekaoptomer (registered trademark) N1919 (produced by ADEKA) or Adeka Arcles (registered trademark) NCI-831 (produced by ADEKA).
- the photosensitive resin composition of the present invention may contain a solvent.
- the solvent include propylene glycol monomethyl ether, propylene glycol monobutyl ether, 2-heptanol, cyclohexanol, cyclopentanol, 2-butanol, 2-pentanol, t-butanol, diacetone alcohol, ⁇ -terpineol, 2- Methyl hydroxyisoisobutyrate, ethyl 2-hydroxyisoisobutyrate, propylene glycol monoethyl ether acetate, ethyl acetoacetate, methyl acetoacetate, methyl-3-methoxypropionate, 3-methyl-3-methoxybutylacetate, cyclopentanone, Cyclohexanone, benzyl ethyl ether, dihexyl ether, acetonyl acetone, isophorone, benzyl acetate, ethyl
- the photosensitive resin composition of the present invention may contain particles other than the conductive particles (A) whose surface is coated with a carbon simple substance and / or a carbon compound for the purpose of improving dispersibility and controlling conductivity. I do not care.
- the other particles include metal fine particles or metal oxide fine particles, organic pigments, or inorganic pigments that are not surface-coated.
- the particle diameter of these other particles is preferably 10 to 100 nm.
- the particle diameter is less than 10 nm, the use of a dispersant for stabilizing the dispersion increases, and it may be difficult to obtain desired conductivity.
- the particle diameter exceeds 100 nm, the resolution of the pattern is lowered, and it may be difficult to form an ultrafine pattern of 5 ⁇ m or less.
- These other particles are preferably carbon black, which contributes to conductivity control.
- Examples of carbon black include MA77, 7, 8, 11, 100, 100R, 100S, 230, 220, or 14 (all of which are manufactured by Mitsubishi Chemical Corporation), # 52, 47, 45, 45L, 44, 40. 33, 32, 30, 25, 20, 10, 5, 95, 85 or 260 (all are manufactured by Mitsubishi Chemical Corporation), Special Black 100, 250, 350 or 550 (all are manufactured by Evonik Degussa) Or Printex95, 90, 55, 45, 40, P, 60, L6, L, 300, 30, ES23, 9, ES22, 35, 25, 200, A or G (all of which are manufactured by Evonik Degussa) be able to.
- MA77, 7, 8, 11, 100, 100R, 100S, 230, 220, or 14 or Special Black 100, 250, 350, or 550 having a pH value of 4 or less is preferable.
- the pH value of carbon black can be measured according to JIS K5101.
- the photosensitive resin composition of the present invention may contain a thermal acid generator and / or a photoacid generator.
- the generated acid promotes the decomposition of the acid-dissociable group in the alkali-soluble resin (B) having an acid-dissociable group, so that the heat treatment temperature under air can be lowered.
- thermal acid generator that is a compound that generates an acid by heat
- examples of the thermal acid generator that is a compound that generates an acid by heat include SI-60, SI-80, SI-100, SI-110, SI-145, SI-150, SI-60L, SI-80L, SI-100L, SI-110L, SI-145L, SI-150L, SI-160L, SI-180L or SI-200 (all of which are manufactured by Sanshin Chemical Industry Co., Ltd.), 4-hydroxyphenyldimethylsulfonium, benzyl -4-hydroxyphenylmethylsulfonium, 2-methylbenzyl-4-hydroxyphenylmethylsulfonium, 2-methylbenzyl-4-acetylphenylmethylsulfonium, 2-methylbenzyl-4-benzoyloxyphenylmethylsulfonium, or methanesulfonic acid thereof Salt
- trifluoromethanes Hong salts include camphorsulfonate or p- toluenesul
- Phenylmethylsulfonium or a methanesulfonate, trifluoromethanesulfonate, camphorsulfonate or p-toluenesulfonate can be preferably used.
- the content of the thermal acid generator in the photosensitive resin composition is preferably 0.01 to 20 parts by mass with respect to 100 parts by mass of the alkali-soluble resin (B) having an acid dissociable group.
- the content of the thermal acid generator is preferably 0.01 to 20 parts by mass with respect to 100 parts by mass of the alkali-soluble resin (B) having an acid dissociable group.
- the acid generated from the photoacid generator that is a compound that generates an acid by light is preferably a strong acid such as perfluoroalkylsulfonic acid or p-toluenesulfonic acid in order to promote the decomposition of the acid dissociable group.
- Examples of the photoacid generator include SI-101, SI-105, SI-106, SI-109, PI-105, PI-106, PI-109, NAI-100, NAI-1002, NAI-1003, and NAI. -1004, NAI-101, NAI-105, NAI-106, NAI-109, NDI-101, NDI-105, NDI-106, NDI-109, PAI-01, PAI-101, PAI-106 or PAI-1001 (All as above, manufactured by Midori Chemical Co., Ltd.), SP-077 or SP-082 (all as described above, manufactured by ADEKA), TPS-PFBS (manufactured by Toyo Gosei Co., Ltd.), CGI-MDT or CGI -NIT (all of which are manufactured by Ciba Japan) or WPAG-281, WPAG-336, WPAG 339, WPAG-342, WPAG-344, WPAG-350, WPAG-370, W
- the content of the photoacid generator in the photosensitive resin composition is preferably 0.01 to 20 parts by mass with respect to 100 parts by mass of the alkali-soluble resin (B) having an acid dissociable group.
- the decomposition of the acid dissociable group in the alkali-soluble resin (B) having an acid dissociable group is promoted, and the surface is coated with a carbon simple substance and / or a carbon compound. This is because contact between the formed conductive particles (A) is not hindered and higher conductivity is obtained.
- a thermal acid generator and a photoacid generator may be used in combination.
- the photosensitive resin composition of the present invention may contain a polymerization inhibitor.
- a polymerization inhibitor By containing a suitable amount of a polymerization inhibitor, the resolution after development is improved.
- the polymerization inhibitor is not particularly limited, and known ones can be used. Examples thereof include di-t-butylhydroxytoluene, butylhydroxyanisole, hydroquinone, 4-methoxyphenol, 1,4-benzoquinone, and t-butylcatechol.
- IRGANOX 1010 When the photosensitive resin composition of the present invention contains a photoacid generator, the photosensitive resin composition may further contain a sensitizer.
- the sensitizer is preferably one that vaporizes by heat treatment, or one that fades when irradiated with light even when it remains in the cured film. From the viewpoint of high resolution in pattern processing, it is more preferable that the sensitizer is discolored by light irradiation.
- coumarin such as 3,3′-carbonylbis (diethylaminocoumarin)
- anthraquinone such as 9,10-anthraquinone
- benzophenone 4,4 ′.
- -Aromatic ketones such as dimethoxybenzophenone, acetophenone, 4-methoxyacetophenone or benzaldehyde or biphenyl, 1,4-dimethylnaphthalene, 9-fluorenone, fluorene, phenanthrene, triphenylene, pyrene, anthracene, 9-phenylanthracene, 9-methoxyanthracene 9,10-diphenylanthracene, 9,10-bis (4-methoxyphenyl) anthracene, 9,10-bis (triphenylsilyl) anthracene, 9,10-dimethoxyanthracene 9,10-diethoxyanthracene, 9,10-dipropoxyanthracene (DPA; manufactured by Kawasaki Kasei Co., Ltd.), 9,10-dibutoxyanthracene (DBA; manufactured by Kawasaki Kasei Co., Ltd.), 9,10-dipenta Examples include
- the sensitizer that is vaporized by the heat treatment a sensitizer that sublimates, evaporates, or thermally decomposed by thermal decomposition by the heat treatment is preferable.
- the vaporization temperature of the sensitizer is not vaporized at the pre-baking temperature, but decomposes and vaporizes during thermal curing to contact and fuse the conductive particles (A) whose surface is coated with a carbon simple substance and / or a carbon compound. 150 to 300 ° C. is preferable.
- the sensitizer is preferably an anthracene compound from the viewpoint that high sensitivity and high resolution can be achieved, and dimerization and fading by light irradiation.
- it is preferably a 9,10-disubstituted anthracene compound that is stable to heat, and is represented by the general formula (2) from the viewpoint of improving the solubility of the sensitizer and the reactivity of the photodimerization reaction. More preferably, it is a 9,10-dialkoxyanthracene compound.
- R 4 ⁇ R 11 each independently represent hydrogen, an alkyl group having 1 to 20 carbon atoms, an alkoxy group, an alkenyl group, an ethynyl group, an aryl group or an acyl group or an organic group which they are substituted
- R 12 And R 13 each independently represents an alkoxy group having 1 to 20 carbon atoms or an alkoxy group substituted with another organic group.
- Examples of the alkyl group for R 4 to R 11 include a methyl group, an ethyl group, and an n-propyl group.
- the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a pentyloxy group.
- alkenyl group examples include a vinyl group, an acryloxypropyl group, and a methacryloxypropyl group.
- an aryl group a phenyl group, a tolyl group, or a naphthyl group is mentioned, for example.
- the acyl group examples include an acetyl group.
- R 4 to R 11 are preferably hydrogen or an organic group having 1 to 6 carbon atoms, and R 4 , R 7 , R 8 and R 11 More preferably, is hydrogen.
- Examples of the substituent that substitutes the alkoxy group in R 12 and R 13 include an alkoxy group and an acyl group.
- Examples of the alkoxy group in this case include methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, methoxyethoxy group, 1-methoxy-2-propoxy group or 1-acetyl-2-propoxy group.
- a propoxy group or a butoxy group is preferable from the viewpoint of the solubility of the compound and the fading reaction due to photodimerization.
- the sensitizer content in the photosensitive resin composition is preferably 0.001 to 20 parts by mass and more preferably 0.005 to 15 parts by mass with respect to 100 parts by mass of the alkali-soluble resin (B).
- the sensitizing effect for sensitizing the photoacid generator is sufficient, and the conductive particles (A) whose surfaces are coated with a carbon simple substance and / or a carbon compound are combined. This is because contact with the film is not hindered and higher conductivity is obtained.
- the photosensitive resin composition of the present invention inhibits contact and fusion between conductive particles (A) whose surfaces are coated with a pigment and / or dye that absorbs visible light with a carbon simple substance and / or a carbon compound. You may contain in the range which does not. Visible light reflection of the conductive pattern after post-baking can be suppressed because the photosensitive resin composition contains a pigment and / or dye that absorbs visible light.
- pigments that absorb visible light include lactam pigments, perylene pigments, phthalocyanine pigments, isoindoline pigments, diaminoanthraquinone pigments, dioxazine pigments, indanthrone pigments, carbon black, and inorganic pigments. It is done.
- Examples of blue pigments include C.I. I. Pigment Blue (hereinafter “PB”) 15, PB15: 1, PB15: 2, PB15: 3, PB15: 4, PB15: 5, PB15: 6, PB16 or PB60.
- Examples of purple pigments include C.I. I. Pigment violet (hereinafter referred to as “PV”) 19, PV23 or PV37.
- Examples of red pigments include C.I. I. Pigment red (hereinafter “PR”) 149, PR166, PR177, PR179, PR209, or PR254.
- Examples of the green pigment include C.I. I. Pigment Green (hereinafter referred to as “PG”) 7, PG36 or PG58.
- Examples of yellow pigments include C.I. I.
- Pigment yellow (hereinafter “PY”) 150, PY138, PY139, or PY185.
- the black pigment include furnace black such as HCF, MCF, LFF, RCF, SAF, ISAF, HAF, XCF, FEF, GPF or SRF, thermal black such as FT or MT, carbon such as channel black or acetylene black.
- black or lactam pigments for example, “Irgaphor” (registered trademark) black S0100CF; manufactured by BASF).
- carbon black excellent in heat resistance, light resistance and visible light absorption is preferable, and furnace black or lactam pigment is more preferable from the viewpoint of conductivity and dispersibility.
- Examples of carbon black include MA77, 7, 8, 11, 100, 100R, 100S, 230, 220, or 14 (all of which are manufactured by Mitsubishi Chemical Corporation), # 52, 47, 45, 45L, 44, 40. 33, 32, 30, 25, 20, 10, 5, 95, 85 or 260 (all are manufactured by Mitsubishi Chemical Corporation), Special Black 100, 250, 350 or 550 (all are manufactured by Evonik Degussa) Or Printex 95, 90, 55, 45, 40, P, 60, L6, L, 300, 30, ES23, 9, ES22, 35, 25, 200, A or G.
- MA77, 7, 8, 11, 100, 100R, 100S, 230, 220, or 14, or Special Black 100, 250, 350, or 550 having a pH value of 4 or less is preferable.
- the pH value of carbon black can be measured according to JIS K5101.
- the addition amount of the pigment having absorption in visible light in the photosensitive resin composition is preferably 0.1 to 10% by mass with respect to the total solid content in the composition.
- dyes that absorb visible light include, for example, ferrocene dyes, fluorenone dyes, perylene dyes, triphenylmethane dyes, coumarin dyes, diphenylamine dyes, quinacridone dyes, quinophthalone dyes, phthalocyanine dyes or Xanthene dyes may be mentioned, but black dyes having excellent heat resistance, light resistance and absorption of visible light are preferable.
- VALIFAST registered trademark
- VALIFAST registered trademark
- VALIFAST registered trademark
- VALIFAST registered trademark
- Black 3830 VALIFAST (registered trademark) Black 3830
- NUBIAN registered trademark
- Black PA- 2802 or OIL Black 860 is preferred.
- the addition amount of the dye having absorption in visible light in the photosensitive resin composition is preferably 0.1 to 10% by mass with respect to the total solid content in the composition.
- the conductive resin (A) having the acrylic monomer surface-coated with a carbon simple substance and / or a carbon compound from the viewpoint of adjusting the photosensitivity and improving the pattern processability, the conductive resin (A) having the acrylic monomer surface-coated with a carbon simple substance and / or a carbon compound. You may contain in the range which does not inhibit a contact and melt
- acrylic monomer examples include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol penta (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, or di Pentaerythritol penta (meth) acrylate or an alkyl modified product, an alkyl ether modified product or an alkyl ester modified product thereof may be mentioned.
- the photosensitive resin composition of the present invention may further contain an adhesion improver, a surfactant, a polymerization inhibitor or the like, if necessary.
- adhesion improving agent examples include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2-amino Ethyl) -3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyl
- silane coupling agents such as trimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, and 3-mercaptopropyltrimethoxysilane.
- the surfactant examples include an anionic surfactant such as ammonium lauryl sulfate or polyoxyethylene alkyl ether sulfate triethanolamine, a cationic surfactant such as stearylamine acetate or lauryltrimethylammonium chloride, lauryldimethylamine oxide, or lauryl.
- Amphoteric surfactants such as carboxymethylhydroxyethyl imidazolium betaine
- nonionic surfactants such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether or sorbitan monostearate, fluorosurfactants or silicon surfactants Can be mentioned.
- the addition amount of the surfactant in the photosensitive resin composition is preferably 0.001 to 10% by mass with respect to the entire composition in order to improve the coating property and the uniformity of the coating film surface, and 0.01 More preferably, it is ⁇ 1% by mass.
- the addition amount is less than 0.001% by mass, the effect of coating property and coating surface uniformity may be insufficient.
- the addition amount exceeds 10% by mass, coating film defects such as cissing and dents and particle aggregation may occur.
- polymerization inhibitor examples include hydroquinone, catechol, phosphorus, sulfur, amine or hindered phenol compounds.
- hydroquinone and catechol-based compounds are preferably hydroquinone-based or catechol-based compounds that do not inhibit solubility in solvents and pigment dispersion stability.
- Hydroquinone, tert-butylhydroquinone, 2,5-bis ( 1,1,3,3-tetramethylbutyl) hydroquinone, 2,5-bis (1,1-dimethylbutyl) hydroquinone, catechol or tert-butylcatechol is more preferred.
- the photosensitive resin composition of the present invention is produced using a dispersing machine such as a ball mill, a sand grinder, a 3 roll mill, a mild disperser, or a medialess disperser.
- a dispersing machine such as a ball mill, a sand grinder, a 3 roll mill, a mild disperser, or a medialess disperser.
- a dispersion in which the conductive particles (A) are dispersed is prepared, and this dispersion is produced by mixing with a solution containing a monomer, a polymer, an adhesion improver, a surfactant, a polymerization inhibitor and the like. Also good.
- the dispersion liquid of the conductive particles (A) whose surface is coated with the carbon simple substance and / or the carbon compound is dispersed using a mild disperser or a medialess disperser. It is preferable to disperse using a medialess disperser.
- the dispersion liquid of the conductive particles (A) whose surface is coated with a carbon simple substance and / or a carbon compound is, for example, mild disperser Nanogetter (registered trademark) (Ashizawa Finetech Co., Ltd.) or high pressure wet medialess atomization.
- a disperser such as an apparatus nanomizer (Nanomizer Co., Ltd.)
- the conductive particles (A) whose surface is coated with a carbon simple substance and / or a carbon compound are dispersed in an organic solvent.
- the method for producing a conductive pattern of the present invention comprises a coating step of applying the photosensitive resin composition of the present invention on a substrate surface, a pre-baking step of drying the substrate, a step of exposing and developing it to form a pattern (exposure) Step, development step) and a post-baking step for post-baking the same.
- Examples of the substrate used in the coating process include a silicon wafer, a ceramic substrate, and an organic substrate.
- the ceramic substrate include glass substrates such as soda glass, non-alkali glass, borosilicate glass, and quartz glass, alumina substrates, aluminum nitride substrates, and silicon carbide substrates.
- the organic substrate include an epoxy substrate, a polyetherimide resin substrate, a polyether ketone resin substrate, a polysulfone resin substrate, a polyimide film, and a polyester film.
- Examples of the method for coating the photosensitive resin composition of the present invention on a substrate surface include coating using a spin coater, bar coater, blade coater, roll coater, die coater, calendar coater or meniscus coater, screen printing, and spraying. Application or dip coating may be mentioned.
- drying method in the pre-baking step examples include hot plate, hot air dryer (oven), vacuum drying, vacuum drying, and drying by infrared irradiation.
- the prebaking temperature and time may be appropriately determined depending on the composition of the photosensitive resin composition and the thickness of the coating film to be dried, but it is preferably heated at a temperature range of 50 to 150 ° C. for 10 seconds to 30 minutes.
- the ultimate pressure for drying under reduced pressure is preferably 10 to 200 Pa, more preferably 30 to 100 Pa.
- the light source used in the exposure process for example, j-ray, i-line, h-line or g-line of a mercury lamp is preferable.
- alkaline substance used for the alkaline developer in the development step examples include inorganic alkalis such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium silicate, sodium metasilicate, or aqueous ammonia, ethylamine, or n-propyl.
- inorganic alkalis such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium silicate, sodium metasilicate, or aqueous ammonia, ethylamine, or n-propyl.
- Primary amines such as amines, secondary amines such as diethylamine or di-n-propylamine, tertiary amines such as triethylamine or methyldiethylamine, tetraalkylammonium hydroxides such as tetramethylammonium hydroxide (TMAH) , Quaternary ammonium salts such as choline, triethanolamine, diethanolamine, monoethanolamine, alcoholamines such as dimethylaminoethanol or diethylaminoethanol, or pillows And organic alkalis such as cyclic amines such as piperidine, 1,8-diazabicyclo [5,4,0] -7-undecene, 1,5-diazabicyclo [4,3,0] -5-nonane or morpholine. It is done.
- a water-soluble organic solvent such as ethanol, ⁇ -butyrolactone, dimethylformamide, or N-methyl-2-pyrrolidone may be appropriately added to these al
- a surfactant such as a nonionic surfactant to these alkaline developers.
- drying method in the post-bake process examples include the same as those in the pre-bake process.
- the post-baking atmosphere, temperature, and time may be appropriately determined depending on the composition of the photosensitive resin composition and the thickness of the coating film to be dried, but in the temperature range of 100 to 300 ° C. for 5 to 120 minutes. It is preferable to heat.
- the conductive pattern is formed in a mesh shape on the substrate, it can be used as a transparent conductive wiring provided in a touch panel, a display panel such as liquid crystal or organic EL, or a wearable terminal.
- the conductive pattern is not transparent, if the pattern width is large, the user of the device can visually recognize the wiring. For this reason, it is preferable that the width
- membrane containing the organic component used in this invention is demonstrated. It is preferable to contain alkali-soluble resin as a component which comprises the film
- alkali-soluble resin By having an alkali-soluble group, complex formation with the metal chelate compound (C) in the photosensitive resin composition of the present invention becomes possible. Since the metal chelate (C) can be complexed with the alkali-soluble resin (B) having an acid dissociable group in the photosensitive resin composition of the present invention, the development adhesion is improved. As a result, processing under severe development conditions is possible, and development residues can be reduced.
- the alkali-soluble resin in the film containing an organic component preferably has a polar group.
- the polar group include a hydroxyl group, a carbonyl group, a carboxyl group, an amino group, a nitro group, and a cyano group, and a carboxyl group is preferable from the viewpoint of alkali developability.
- a cardo resin having a high film density after curing is preferable from the viewpoint of reliability.
- an acrylic polymer is contained, and the content of the cardo resin and the acrylic polymer is preferably 1:10 to 10: 1 by weight, and preferably 1: 8 to 7: 1. More preferred.
- the cardo-based resin in the film containing the organic component commercially available products can be preferably used.
- “WR-301 (trade name)” manufactured by ADEKA
- “V-259ME (trade name)” (Nippon Steel) Manufactured by Sumikin Chemical Co., Ltd.)
- “Ogsol CR-TR1 (trade name)” “Ogsol CR-TR2 (trade name)”
- “Ogsol CR-TR4 (trade name)” “ Ogsol CR-TR5 (trade name) ”,“ Ogsol CR-TR6 (trade name) ”(above, manufactured by Osaka Gas Chemical Co., Ltd.), and the like.
- an acrylic polymer having an alicyclic skeleton in the side chain can be used.
- the acrylic polymer is obtained by radical copolymerization of a carboxyl group and / or an acid anhydride group-containing (meth) acrylic compound, (meth) acrylic acid ester, and / or maleimide or maleimide derivative, and then an ethylenically unsaturated double bond group. What is obtained by addition-reacting an epoxy compound having a hydrogen atom is preferred.
- the radical polymerization catalyst is not particularly limited, and an azo compound such as azobisisobutyronitrile, an organic peroxide such as benzoyl peroxide, or the like is generally used.
- the catalyst used for the addition reaction of the epoxy compound having an ethylenically unsaturated double bond group is not particularly limited, and a known catalyst can be used.
- a known catalyst can be used.
- Amino catalysts such as phenol and dimethylbenzylamine
- tin catalysts such as tin 2-ethylhexanoate (II) and dibutyltin laurate
- titanium catalysts such as titanium 2-ethylhexanoate (IV)
- phosphorus-based catalysts such as acetylacetonate chromium and chromium chloride.
- Examples of the (meth) acrylic compound containing a carboxyl group and / or an acid anhydride group include (meth) acrylic acid, (meth) acrylic anhydride, itaconic acid, itaconic anhydride, and succinic acid mono (2-acryloyloxyethyl) Mono (2-acryloyloxyethyl) phthalate, mono (2-acryloyloxyethyl) tetrahydrophthalate and the like are used.
- (Meth) acrylic acid esters include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, cyclopropyl (meth) acrylate, cyclopentyl (meth) acrylate, (meth) acrylic acid Cyclohexyl, cyclohexenyl (meth) acrylate, 4-methoxycyclohexyl (meth) acrylate, 2-cyclopropyloxycarbonylethyl (meth) acrylate, 2-cyclopentyloxycarbonylethyl (meth) acrylate, (meth) acrylic acid 2-cyclohexyloxycarbonylethyl, (meth) acrylic acid 2-cyclohexenyloxycarbonylethyl, (meth) acrylic acid 2- (4-methoxycyclohexyl) oxycarbonylethyl, (meth) acrylic acid norbornyl, (meth) acrylic Isobonyl acid
- an aromatic vinyl compound such as styrene, p-methylstyrene, o-methylstyrene, m-methylstyrene, ⁇ -methylstyrene or the like is copolymerized with the above (meth) acrylic acid or (meth) acrylic acid ester. Also good.
- maleimides or maleimide derivatives include maleimide, N-methylmaleimide, N-ethylmaleimide, Nn-propylmaleimide, N-isobutylmaleimide, Nn-butylmaleimide, Nt-butylmaleimide, Nn -Hexylmaleimide, N-dodecylmaleimide, N-cyclopentylmaleimide, N-cyclohexylmaleimide, N- (2,4-dimethylcyclohexyl) maleimide, N-vinylmaleimide, N- (meth) acrylmaleimide, N-methoxymethylmaleimide, N- (2-ethoxyethyl) maleimide, N- [3- (meth) acryloxypropyl] maleimide, N-methoxycarbonylmaleimide, N- (3-methoxycarbonylpropyl) maleimide, N- (2-hydroxyethyl) male N- (4-hydroxy-
- Examples of the epoxy compound having an ethylenically unsaturated double bond group include glycidyl (meth) acrylate, ⁇ -ethylglycidyl (meth) acrylate, ⁇ -n-propylglycidyl (meth) acrylate, and (meth) acrylic.
- acrylic polymer a polymer obtained by polymerizing a polyfunctional (meth) acrylate compound and a polyvalent mercapto compound by Michael addition ( ⁇ position with respect to the carbonyl group) can also be used.
- Preferred specific examples of the polyfunctional (meth) acrylate compound include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, and tetramethylene glycol.
- polyvalent mercapto compound examples include 1,2-dimercaptoethane, 1,3-dimercaptopropane, 1,4-dimercaptobutane, bisdimercaptoethanethiol (HS—CH 2 CH 2 —S—CH 2 CH 2 -SH), trimethylolpropane tri (mercaptoacetate), trimethylolpropane tri (mercaptopropionate), pentaerythritol tetra (mercaptoacetate), pentaerythritol tri (mercaptoacetate), pentaerythritol tetra (mercaptopropionate), Examples include dipentaerythritol hexa (mercaptoacetate), dipentaerythritol hexa (mercaptopropionate), and the like. These compounds may be used alone or in combination of two or more.
- [Metal chelate compound (C)] (C-1) ALCH: ethyl acetoacetate aluminum diisopropylate (manufactured by Kawaken Fine Chemical Co., Ltd.) (C-2) ALCH-TR: Aluminum trisethyl acetoacetate (manufactured by Kawaken Fine Chemical Co., Ltd.) (C-3) Aluminum chelate M: alkyl acetoacetate aluminum diisopropylate (manufactured by Kawaken Fine Chemical Co., Ltd.) (C-4) Aluminum chelate D: Aluminum monoacetylacetonate bis (ethylacetoacetate) (manufactured by Kawaken Fine Chemical Co., Ltd.) (C-5) Aluminum chelate A (W): Aluminum tris (acetylacetonate) (manufactured by Kawaken Fine Chemical Co., Ltd.) (C-6) ZC-150: zirconium tetracetyl acetonate (manu
- NCI-831 registered trademark (oxime ester compound; manufactured by ADEKA Corporation).
- the pre-baked film was exposed through a desired mask using a parallel light mask aligner (“PLA-501F (trade name)” manufactured by Canon Inc.) using an ultrahigh pressure mercury lamp as a light source.
- PPA-501F parallel light mask aligner
- AD-2000 automatic developing device manufactured by Takizawa Sangyo Co., Ltd.
- shower development is performed with 0.045 wt% potassium hydroxide aqueous solution for 60 seconds, and then rinsed with water for 30 seconds.
- Pattern processing was performed.
- a film (Y-1) containing an organic component was produced by post-baking at 230 ° C. for 30 minutes (in the air) using an oven (“IHPS-222”; manufactured by Espec Corp.).
- the composition (X-2) was placed on an alkali-free glass substrate (OA-10G; manufactured by Nippon Electric Glass Co., Ltd.) using a spin coater (“1H-360S (trade name)” manufactured by Mikasa Co., Ltd.) at 650 rpm.
- the substrate was spin-coated under conditions of 5 seconds, and the substrate was pre-baked at 100 ° C. for 2 minutes using a hot plate (“SCW-636 (trade name)” manufactured by Dainippon Screen Mfg. Co., Ltd.). After obtaining the pre-baked film, it was post-baked at 230 ° C. for 30 minutes (in the air) using an oven (“IHPS-222”; manufactured by Espec Corp.), so that the film containing organic components (Y-2 ) Was produced.
- the resolution is preferably 5 ⁇ m or less, and more preferably 2 ⁇ m or less.
- the surface resistance value ⁇ s ( ⁇ / ⁇ ) measured with a surface resistance measuring device (“Loresta (registered trademark) -FP” manufactured by Mitsubishi Yuka Co., Ltd.) and surface roughness shape measurement Volume resistivity ( ⁇ ⁇ cm) is calculated by measuring the film thickness t (cm) measured by the machine (“Surfcom (registered trademark) 1400D” manufactured by Tokyo Seimitsu Co., Ltd.) and multiplying both values. did.
- the volume resistivity is preferably less than 100 ⁇ ⁇ cm, more preferably less than 65 ⁇ ⁇ cm.
- the residue on the substrate was evaluated by transmittance evaluation. Specifically, the transmittance at 400 nm before and after film formation was measured for an unexposed portion using an ultraviolet-visible spectrophotometer (“MultiSpec-1500 (trade name)” manufactured by Shimadzu Corporation). Then, the transmittance change represented by the formula (T0 ⁇ T) / T0 was calculated, where T0 was the transmittance before film formation and T was the transmittance after film formation.
- the change in transmittance is preferably less than 1.0%, more preferably less than 0.7%.
- Example 1 First, 80.00 g of conductive particles (A-1) surface-coated with a carbon simple substance and / or a carbon compound, 6.25 g of DISPERBYK21116, PGMEA146.25 g, and DPM150.00 g were analyzed with a homogenizer at 1200 rpm, 30 The mixture was further dispersed using a high-pressure wet medialess atomizer Nanomizer (Nanomizer Co., Ltd.) to obtain a silver particle dispersion.
- the photosensitive resin composition 1 is applied on a film (Y-1) containing an organic component using a spin coater (“1H-360S (trade name)” manufactured by Mikasa Co., Ltd.) for 10 seconds at 300 rpm and 2 at 500 rpm.
- the substrate was spin-coated for 2 seconds, and the substrate was prebaked at 100 ° C. for 2 minutes using a hot plate (“SCW-636 (trade name)” manufactured by Dainippon Screen Mfg. Co., Ltd.) to obtain a prebaked film having a thickness of 1 ⁇ m It was.
- the pre-baked film was exposed through a desired mask using a parallel light mask aligner (“PLA-501F (trade name)” manufactured by Canon Inc.) using an ultrahigh pressure mercury lamp as a light source.
- PPA-501F parallel light mask aligner
- AD-2000 automatic developing device manufactured by Takizawa Sangyo Co., Ltd.
- shower development is performed with 0.045 wt% potassium hydroxide aqueous solution for 60 seconds, and then rinsed with water for 30 seconds.
- Pattern processing was performed.
- the exposure amount (hereinafter referred to as “optimum exposure amount”) for forming a 5 ⁇ m line-and-space pattern in a one-to-one width was defined as sensitivity.
- the exposure amount was measured with an I-line illuminometer. Then, the minimum pattern size after development at the optimum exposure amount was measured to obtain the resolution.
- the photosensitive resin composition 1 was separately provided on a film (Y-1) containing an organic component using a spin coater (“1H-360S (trade name)” manufactured by Mikasa Co., Ltd.) at 300 rpm for 10 seconds. Spin coat at 500 rpm for 2 seconds, pre-bake the substrate for 2 minutes at 100 ° C. using a hot plate (“SCW-636 (trade name)” manufactured by Dainippon Screen Mfg. Co., Ltd.), and prebake with a film thickness of 1 ⁇ m A membrane was obtained. The pre-baked film was exposed through a desired mask using a parallel light mask aligner (“PLA-501F (trade name)” manufactured by Canon Inc.) using an ultrahigh pressure mercury lamp as a light source.
- a spin coater (“1H-360S (trade name)” manufactured by Mikasa Co., Ltd.) at 300 rpm for 10 seconds. Spin coat at 500 rpm for 2 seconds, pre-bake the substrate for 2 minutes at 100 ° C. using
- the surface resistance value ⁇ s ( ⁇ / ⁇ ) measured with a surface resistance measuring machine (Loresta (registered trademark) -FP; manufactured by Mitsubishi Yuka Co., Ltd.), and a surface roughness shape measuring machine The film thickness t (cm) measured by (Surfcom (registered trademark) 1400D; manufactured by Tokyo Seimitsu Co., Ltd.) was measured, and the volume resistivity ( ⁇ ⁇ cm) was calculated by multiplying both values.
- substrate was evaluated by transmittance
- the transmittance at 400 nm before and after film formation was measured for the unexposed part using a spectrophotometer (U-3410; manufactured by Hitachi, Ltd.).
- the transmittance change represented by the formula (T 0 -T) / T 0 was calculated, where T 0 is the transmittance before film formation and T is the transmittance after film formation. If the change in transmittance is less than 1%, it can be determined that the effect of suppressing residue is sufficient.
- Table 1 shows the measured resolution and the calculated volume resistivity and transmittance change results.
- Examples 2 to 21 and Comparative Examples 1 to 11 A photosensitive resin composition having the composition described in Table 1 was obtained in the same manner as in Example 1, and each photosensitive resin composition was evaluated in the same manner as in Example 1 on the substrates described in Tables 1 to 3. . The evaluation results are shown in Tables 1 to 3.
- a non-alkali glass substrate (OA-10G; manufactured by Nippon Electric Glass Co., Ltd.) was used as the glass substrate in the table.
- Comparative Examples 1 to 9 since the alkali-soluble resin did not have an acid dissociable group, formation of a fine pattern was insufficient. In Comparative Examples 10 and 11, since the metal chelate compound was not added, the effect of suppressing the residue was insufficient.
- the photosensitive resin composition of the present invention can be suitably used for forming a conductive pattern used for a touch panel, a display, an image sensor, organic electroluminescence illumination, a solar cell, or the like.
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Abstract
Description
炭素単体物および/または炭素化合物で表面被覆された導電性粒子(A)は、表面を被覆する層(以下、「表面被覆層」)が存在することにより、低温での導電性粒子同士の融着を抑制することができる。
W2=π/6×Dp3ρ×n
そして、以下の式から表面被覆層の平均厚みAを算出することができる。
W1-W2={4/3×π(Dp/2+A)3-π/6×Dp3}×2.0×n
感光性樹脂組成物中の炭素単体物および/または炭素化合物で表面被覆された導電性粒子(A)の含有量としては、65~95質量%であることが好ましく、70~95質量%であることがより好ましく、70~90質量%であることがさらに好ましい。その範囲内で含有することで、パターン加工性と導電性の発現とを両立させることができる。ここで全固形分とは、感光性樹脂組成物が含有する成分の内、溶剤を除く全成分をいう。
(i) 感光性樹脂組成物を有機溶媒で希釈し、1H-NMR測定、GC測定及びGC/MS測定をしてその概要を調べる。
(ii) 感光性樹脂組成物を有機溶媒抽出した後に遠心分離を行い、可溶分と不溶分とを分離する。
(iii) 上記不溶分について、高極性有機溶媒で抽出した後に遠心分離を行い、可溶分と不溶分とをさらに分離する。
(iv) 上記(ii)及び(iii)で得られた可溶分の混合液について、IR測定、1H-NMR測定及びGC/MS測定を行う。さらに、上記混合液をGPC分取する。得られた分取物についてIR測定及び1H-NMR測定を行う。また、該分取物については、必要に応じてGC測定、GC/MS測定、熱分解GC/MS測定及びMALDI/MS測定を行う。
(v) 上記(iii)で得られた不溶分についてIR測定又はTOF-SIMS測定を行う。有機物が存在することが確認された場合には、熱分解GC/MS又はTPD/MS測定を行う。
(vi) 上記(i)、(iv)及び(v)の測定結果を総合的に判断することで、感光性樹脂組成物が含有する各成分の含有率を求めることができる。なお、上記(iii)で用いる高極性有機溶媒としては、クロロホルム又はメタノール等が好ましい。
アルカリ可溶性樹脂に酸解離性基を含有させることで、パターン形成後の熱処理で酸解離性基が脱離分解、気化し、パターンが収縮する。これにより、炭素単体物および/または炭素化合物で表面被覆された導電性粒子(A)同士の接触を促進し、導電性を向上させると共に、微細なパターンを形成することが可能である。
酸解離性基を有するアルカリ可溶性樹脂(B)は、一般的に、カルボキシル基を含有する化合物と酸解離性基を有する化合物および他モノマーとを共重合させることにより得られる。酸解離性基を有するアルカリ可溶性樹脂(B)は、(メタ)アクリル系共重合体であることが好ましい。ここで(メタ)アクリル系共重合体とは、共重合成分に少なくとも(メタ)アクリル系モノマーを含む共重合体をいう。ここで(メタ)アクリル系モノマーとしては、例えば、メチル(メタ)アクリレート、エチル(メタ)アクリレート、n-プロピル(メタ)アクリレート、イソプロピル(メタ)アクリレート、n-ブチル(メタ)アクリレート、sec-ブチル(メタ)アクリレート、イソブチル(メタ)アクリレート、tert-ブチル(メタ)アクリレート、n-ペンチル(メタ)アクリレート、アリル(メタ)アクリレート、ベンジル(メタ)アクリレート、ブトキシエチル(メタ)アクリレート、ブトキシトリエチレングリコール(メタ)アクリレート、シクロへキシル(メタ)アクリレート、ジシクロペンタニル(メタ)アクリレート、ジシクロペンテニル(メタ)アクリレート、2-エチルへキシル(メタ)アクリレート、グリセロール(メタ)アクリレート、グリシジル(メタ)アクリレート、ヘプタデカフロロデシル(メタ)アクリレート、2-ヒドロキシエチル(メタ)アクリレート、イソボニル(メタ)アクリレート、2-ヒドロキシプロピル(メタ)アクリレート、イソデキシル(メタ)アクリレート、イソオクチル(メタ)アクリレート、ラウリル(メタ)アクリレート、2-メトキシエチル(メタ)アクリレート、メトキシエチレングリコール(メタ)アクリレート、メトキシジエチレングリコール(メタ)アクリレート、オクタフロロペンチル(メタ)アクリレート、フェノキシエチル(メタ)アクリレート、ステアリル(メタ)アクリレート、トリフロロエチル(メタ)アクリレート、(メタ)アクリルアミド、アミノエチル(メタ)アクリレート、フェニル(メタ)アクリレート、1-ナフチル(メタ)アクリレート、2-ナフチル(メタ)アクリレート、チオフェノール(メタ)アクリレート又はベンジルメルカプタン(メタ)アクリレートが挙げられる。
酸解離性基を有する化合物としては、酸解離性基を有する(メタ)アクリル酸エステルが挙げられる。
金属キレート化合物(C)は、中心金属と、該中心金属に二以上の部位で配位した配位子と、を有する化合物のことであり、配位子が容易に脱離し、アルカリ可溶性官能基と錯形成が可能である。アルカリ可溶性樹脂と錯形成することにより、樹脂成分の現像性を制御可能とし、パターン剥がれ抑制効果が顕著なものとなる。
R1は、水素、炭素数1~6のアルキル基、炭素数4~7のシクロアルキル基又は炭素数6~10のアリール基が好ましく、R2及びR3は、それぞれ独立して、水素、炭素数1~18のアルキル基、炭素数4~7のシクロアルキル基、炭素数6~10のアリール基、炭素数1~4のアルコキシ基又はヒドロキシ基が好ましい。上記のアルキル基、シクロアルキル基、アリール基及びアルコキシ基は、無置換体又は置換体のいずれであっても構わない。Mは、アルミニウム、ジルコニウムまたはビスマスが好ましい。
本発明の感光性樹脂組成物は、分散剤を含有しても構わない。分散剤を含有することで、感光性樹脂組成物中に炭素単体物および/または炭素化合物で表面被覆された導電性粒子(A)を安定的に存在させることができる。
本発明の感光性樹脂組成物は、光重合開始剤を含有しても構わない。光重合開始剤を含有することで、感光性樹脂組成物にネガ型感光性を付与することができる。
本発明の感光性樹脂組成物は、溶剤を含有しても構わない。
溶剤としては、例えば、プロピレングリコールモノメチルエーテル、プロピレングリコールモノブチルエーテル、2-ヘプタノール、シクロヘキサノール、シクロペンタノール、2-ブタノール、2-ペンタノール、t-ブタノール、ダイアセトンアルコール、α-テルピネオール、2-ヒドロキシイソイソ酪酸メチル、2-ヒドロキシイソイソ酪酸エチル、プロピレングリコールモノエチルエーテルアセテート、アセト酢酸エチル、アセト酢酸メチル、メチル-3-メトキシプロピオネート、3-メチル-3-メトキシブチルアセテート、シクロペンタノン、シクロヘキサノン、ベンジルエチルエーテル、ジヘキシルエーテル、アセトニルアセトン、イソホロン、酢酸ベンジル、安息香酸エチル、シュウ酸ジエチル、マレイン酸ジエチル、炭酸エチレン、炭酸プロピレン、メチルベンゾエート、エチルベンゾエート、マロン酸ジエチル、β-プロピオラクトン、γ-ブチロラクトン、γ-バレロラクトン、δ-バレロラクトン、γ-カプロラクトン、ε-カプロラクトン、エチレングリコールモノブチルエーテルアセテート、ジエチレングリコールモノエチルエーテルアセテート、ジエチレングリコールモノブチルエーテルアセテート、ジエチレングリコールジメチルエーテル、ジエチレングリコールジエチルエーテル、ジエチレングリコールメチルエチルエーテル、ジプロピレングリコールメチルエーテルアセテート、ジプロピレングリコールジメチルエーテル、プロピレングリコールジアセテート、1,3-ブチレングリコールジアセテート、シクロヘキサノールアセテート、ジメチルスルホキシド、メチルエチルケトン、酢酸イソブチル、酢酸イソブチル、酢酸ブチル、酢酸プロピル、酢酸イソプロピル、アセチルアセトン、トリアセチン又は2-ヘプタノンが挙げられる。
本発明の感光性樹脂組成物は、分散性向上や、導電性コントロールのため、炭素単体物および/または炭素化合物で表面被覆された導電性粒子(A)以外の他の粒子を含有しても構わない。他の粒子としては、例えば、表面被覆されていない金属微粒子若しくは金属酸化物微粒子、有機顔料又は無機顔料が挙げられる。
本発明の感光性樹脂組成物は、熱酸発生剤および/または光酸発生剤を含有しても構わない。発生した酸によって、酸解離性基を有するアルカリ可溶性樹脂(B)中の酸解離性基の分解が促進され、空気下での熱処理温度を低下させることが可能となる。
(重合禁止剤)
本発明の感光性樹脂組成物は、重合禁止剤を含有してもよい。重合禁止剤を適量含有することで、現像後の解像度が向上する。重合禁止剤としては特に限定はなく公知のものが使用できる。たとえば、ジ-t-ブチルヒドロキシトルエン、ブチルヒドロキシアニソール、ハイドロキノン、4-メトキシフェノール、1,4-ベンゾキノン、t-ブチルカテコールが挙げられる。また、市販の重合禁止剤としては、「IRGANOX1010」、「IRGANOX 1035」、「IRGANOX 1076」、「IRGANOX 1098」、「IRGANOX 1135」、「IRGANOX 1330」、「IRGANOX1726」、「IRGANOX 1425」、「IRGANOX 1520」、「IRGANOX 245」、「IRGANOX 259」、「IRGANOX 3114」、「IRGANOX565」、「IRGANOX 295」(以上、BASF製)等が挙げられる。
(増感剤)
本発明の感光性樹脂組成物が光酸発生剤を含有する場合、感光性樹脂組成物はさらに増感剤を含有しても構わない。増感剤は、熱処理により気化するもの、又は、硬化膜に残存した場合においても、光照射によって退色するものが好ましい。パターン加工における高解像性の観点から、増感剤は光照射によって退色するものがより好ましい。
R4~R11におけるアルキル基としては、例えば、メチル基、エチル基又はn-プロピル基が挙げられる。アルコキシ基としては、例えば、メトキシ基、エトキシ基、プロポキシ基、ブトキシ基又はペンチルオキシ基が挙げられる。アルケニル基としては、例えば、ビニル基、アクリロキシプロピル基又はメタクリロキシプロピル基が挙げられる。アリール基としては、例えば、フェニル基、トリル基又はナフチル基が挙げられる。アシル基としては、例えば、アセチル基が挙げられる。なお、化合物の気化性及び光二量化の反応性の観点から、R4~R11は水素又は炭素数は1~6の有機基であることが好ましく、R4、R7、R8及びR11は水素であることがより好ましい。
本発明の感光性樹脂組成物は、可視光に吸収を有する顔料及び/又は染料を、炭素単体物および/または炭素化合物で表面被覆された導電性粒子(A)同士の接触及び融着を阻害しない範囲で含有しても構わない。感光性樹脂組成物が可視光に吸収を有する顔料および/または染料を含有することより、ポストベーク後の導電性パターンの可視光反射を抑制できる。
本発明の感光性樹脂組成物は、感光性能を調整し、パターン加工性を向上する観点から、アクリルモノマーを、炭素単体物および/または炭素化合物で表面被覆された導電性粒子(A)同士の接触及び融着を阻害しない範囲内で含有しても構わない。
本発明の感光性樹脂組成物は、ボールミルや、サンドグラインダー、3本ロールミル、マイルド分散機、メディアレス分散機等の分散機を用いて製造される。炭素単体物および/または炭素化合物で表面被覆された導電性粒子(A)を均一に分散したい場合は、分散剤を用いて、予め有機溶剤中に炭素単体物および/または炭素化合物で表面被覆された導電性粒子(A)を分散させた分散液を調製し、この分散液を、モノマ、ポリマー、密着改良剤、界面活性剤及び重合禁止剤等を含有する溶液と混合する方法により製造しても良い。炭素単体物および/または炭素化合物で表面被覆された導電性粒子(A)の分散液は、表面被覆層が損傷を受けるのを防ぐために、マイルド分散機又はメディアレス分散機を用いて分散させることが好ましく、メディアレス分散機を用いて分散させることがより好ましい。炭素単体物および/または炭素化合物で表面被覆された導電性粒子(A)の分散液は、例えば、マイルド分散機ナノゲッター(登録商標)(アシザワファインテック(株))又は高圧湿式メディアレス微粒化装置ナノマイザー(ナノマイザー(株))等の分散機を用いて、有機溶剤中に炭素単体物および/または炭素化合物で表面被覆された導電性粒子(A)を分散させて製造される。
次に、本発明の感光性樹脂組成物を用いた、フォトリソ法による導電性パターンの製造方法について説明する。
本発明中で使用される有機成分を含む膜について説明する。
本発明で使用される有機成分を含む膜を構成する成分として、アルカリ可溶性樹脂を含有することが好ましい。アルカリ可溶性基を有することで、本発明の感光性樹脂組成物中の金属キレート化合物(C)と錯形成が可能となる。金属キレート(C)は本発明の感光性樹脂組成物中の酸解離性基を有するアルカリ可溶性樹脂(B)とも錯形成可能であるため、現像密着性が向上する。これにより、厳しい現像条件での処理が可能となり、現像残渣を低減させることができる。
アクリルポリマーは、カルボキシル基及び/または酸無水物基含有(メタ)アクリル化合物、及び(メタ)アクリル酸エステル、及び/またはマレイミドまたはマレイミド誘導をラジカル共重合したのち、エチレン性不飽和二重結合基を有するエポキシ化合物を付加反応して得られるものが好ましい。
(A-1)表面炭素被覆層の平均厚みが1nmで、1次粒子径が50nmの銀粒子(日清エンジニアリング株式会社製)。
(B-1)
500mLのフラスコに2,2’-アゾビス(イソブチロニトリル)を2g、PGMEAを50g仕込んだ。その後、メタクリル酸を15.69g、スチレンを37.45g、ジシクロペンタニルメタクリレートを46.86g仕込み、室温でしばらく撹拌し、フラスコ内をバブリングによって十分に窒素置換した後、70℃で5時間加熱撹拌した。次に、得られた溶液にメタクリル酸グリシジルを10.46g、ジメチルベンジルアミンを1g、p-メトキシフェノールを0.2g、PGMEAを100g添加し、90℃で4時間加熱撹拌し、アクリル樹脂(B-1)の溶液を得た。得られたアクリル樹脂(B-1)の溶液に固形分濃度が40質量%になるようにPGMEAを加えた。アクリル樹脂(B-1)の重量平均分子量(Mw)は25,000であった。
500mLのフラスコに2,2’-アゾビス(イソブチロニトリル)を2g、PGMEA(プロピレングリコールメチルエーテルアセテート)を50g仕込んだ。その後、メタクリル酸を23.26g、ベンジルメタクリレートを31.46g、ジシクロペンタニルメタクリレートを32.80g仕込み、室温でしばらく撹拌し、フラスコ内をバブリングによって十分に窒素置換した後、70℃で5時間加熱撹拌した。次に、得られた溶液にメタクリル酸グリシジルを12.69g、ジメチルベンジルアミンを1g、p-メトキシフェノールを0.2g、PGMEAを100g添加し、90℃で4時間加熱撹拌し、アクリル樹脂(B-2)の溶液を得た。得られたアクリル樹脂(B-2)の溶液に固形分濃度が40質量%になるようにPGMEAを加えた。アクリル樹脂(B-2)の重量平均分子量(Mw)は24,000であった。
(C-1)ALCH:エチルアセトアセテートアルミニウムジイソプロピレート(川研ファインケミカル(株)製)
(C-2)ALCH-TR:アルミニウムトリスエチルアセトアセテート(川研ファインケミカル(株)製)
(C-3)アルミキレートM:アルキルアセトアセテートアルミニウムジイソプロピレート(川研ファインケミカル(株)製)
(C-4)アルミキレートD:アルミニウムモノアセチルアセトネートビス(エチルアセトアセテート)(川研ファインケミカル(株)製)
(C-5)アルミキレートA(W):アルミニウムトリス(アセチルアセトネート)(川研ファインケミカル(株)製)
(C-6)ZC-150:ジルコニウムテトラセチルアセトネート(マツモトファインケミカル(株)製)
(C-7)ZC-540:ジルコニウムトリブトキシモノアセチルアセトネート(マツモトファインケミカル(株)製)
(C-8)ネオスタンU-600:ビスマストリオクテート/2-エチルヘキサン酸(日東化成(株)製)
[分散剤]
DISPERBYK(登録商標)21116(ビックケミー・ジャパン株式会社製)。
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(三協化学(株)製)
DPM:ジプロピレングリコールモノメチルエーテル(東邦化学工業(株)製)。
NCI-831(登録商標)(オキシムエステル系化合物;ADEKA(株)製)。
ライトアクリレート(登録商標)PE-3A(共栄社化学(株)製)。
(X-1)
500mlのフラスコにAIBNを1g、PGMEAを50g仕込んだ。その後、メタクリル酸を38.6g、メタクリル酸メチルを16.4g、スチレンを16.4g仕込み、室温でしばらく撹拌し、フラスコ内をバブリングによって十分に窒素置換した後、70℃で5時間加熱撹拌した。次に、得られた溶液にメタクリル酸グリシジルを28.6g、ジメチルベンジルアミンを1g、p-メトキシフェノールを0.2g、PGMEAを100g添加し、90℃で4時間加熱撹拌し、アクリルポリマーの溶液を得た。得られたアクリルポリマーの重量平均分子量(Mw)は29,000であった。
黄色灯下にて、OXE-02:0.25g、LA-87:0.50g、10wt%PGMEA溶液としたTBC:0.50gをPGMEA:14.19g、DAA:30.00gに溶解させ、10wt%PGMEA溶液としたBYK-333:0.30g(濃度300ppmに相当)を加え、撹拌した。そこへ、50wt%PGMEA溶液としたTEPIC-VL:6.49g、20wt%PGMEA溶液としたEG-200:12.49g、DPHA:6.19g、得られたアクリルポリマー:9.36g、「V-259ME(商品名)」(新日鉄住金化学(株)製):18.73g、及びKBM-403:1.00gを加え、撹拌した。次いで0.45μmのフィルターでろ過を行い、組成物(X-1)を得た。
「スミカエクセルPES 4100P(商品名)」(住友化学(株)製)10gにシクロヘキサノンを40g添加攪拌した。このようにして固形分濃度が20wt%の組成物(X-2)を得た。
乾燥窒素気流下、2,2-ビス(3-アミノ-4-ヒドロキシフェニル)ヘキサフルオロプロパン(BAHF;セントラル硝子(株)製)29.3g(0.08モル)、1,3-ビス(3-アミノプロピル)テトラメチルジシロキサン1.24g(0.005モル)、末端封止剤として、3-アミノフェノール3.27g(0.03モル)をN-メチル-2-ピロリドン(NMP)150gに溶解した。ここに3,3’,4,4’-ジフェニルエーテルテトラカルボン酸二無水物(ODPA;マナック(株)製)31.0g(0.1モル)をNMP50gとともに加えて、20℃で1時間撹拌し、次いで50℃で4時間撹拌した。その後、キシレンを15g添加し、水をキシレンとともに共沸しながら、150℃で5時間撹拌した。撹拌終了後、溶液を水3Lに投入して白色沈殿を集めた。この沈殿をろ過で集めて、水で3回洗浄した後、80℃の真空乾燥機で24時間乾燥し、ポリイミドポリマーを得た。このポリイミドポリマー7.5gにGBLを42.5g添加攪拌した。このようにして固形分濃度が15wt%の組成物(X-3)を得た。
黄色灯下にて、「PBG-305(商品名)」(強力電子社製):0.25g、「LA-87(商品名)」(ADEKA(株)製):0.50g、10wt%PGMEA溶液としたTBC:0.50gをPGMEA:2.24g、DAA:30.00gに溶解させ、10wt%PGMEA溶液としたBYK-333:0.30g(濃度300ppmに相当)を加え、撹拌した。そこへ、「TAIC(商品名)」(日本化成(株)製):4.25g、10wt%PGMEA溶液とした「オグソールPG-100(商品名)」(大阪ガスケミカル(株)製):24.50g、「オグソールEA-0250P(商品名)」(大阪ガスケミカル(株)製):1.25g、「M-315(商品名)」(共栄社(株)製):2.75g、「SIRIUS-501(商品名)」(大阪有機工業(株)製):3.12g、「V-259ME(商品名)」(新日鉄住金化学(株)製):29.34g、及び「KBM-403(商品名)」(信越化学工業(株)製):1.00gを加え、撹拌した。次いで0.45μmのフィルターでろ過を行い、組成物(X-4)を得た。
(Y-1)
組成物(X-1)を、無アルカリガラス基板(OA-10G;日本電気硝子株式会社製)上に、スピンコーター(ミカサ(株)製「1H-360S(商品名)」)を用いて650rpmで5秒の条件でスピンコートし、基板をホットプレート(大日本スクリーン製造(株)製「SCW-636(商品名)」)を用いて100℃で2分間プリベークし、膜厚2.5μmのプリベーク膜を得た。プリベーク膜をパラレルライトマスクアライナー(キヤノン(株)製「PLA-501F(商品名)」)を用いて超高圧水銀灯を光源とし、所望のマスクを介して露光した。この後、自動現像装置(滝沢産業(株)製「AD-2000(商品名)」)を用いて、0.045wt%水酸化カリウム水溶液で60秒間シャワー現像し、次いで水で30秒間リンスし、パターン加工を行った。その後、オーブン(「IHPS-222」;エスペック(株)製)を用いて、230℃で30分(空気中)ポストベークを施すことで、有機成分を含む膜(Y-1)を作製した。
組成物(X-2)を、無アルカリガラス基板(OA-10G;日本電気硝子株式会社製)上に、スピンコーター(ミカサ(株)製「1H-360S(商品名)」)を用いて650rpmで5秒の条件でスピンコートし、基板をホットプレート(大日本スクリーン製造(株)製「SCW-636(商品名)」)を用いて100℃で2分間プリベークし、膜厚2.5μmのプリベーク膜を得たその後、オーブン(「IHPS-222」;エスペック(株)製)を用いて、230℃で30分(空気中)ポストベークを施すことで、有機成分を含む膜(Y-2)を作製した。
上記(Y-2)の作製方法と同様の手順により、(X-3)から(Y-3)を作製した。
上記(Y-1)の作製方法と同様の手順により、(X-4)から(Y-4)を作製した。
無アルカリガラス基板(OA-10;日本電気硝子株式会社製)または前記(Y-1)~(Y-4)の塗布された基板を用い、感光性樹脂組成物のパターン加工性評価を行った。なお、膜厚をプリベーク後2.5μmとし、露光時は感度測定用のグレースケールマスクを用いた。
現像後、30μmのラインアンドスペースパターンを1対1の幅に形成する露光量(以下、これを最適露光量という)を感度とし、最適露光量における現像後の最小パターン寸法を解像度とした。
無アルカリガラス基板(OA-10;日本電気硝子株式会社製)または前記(Y-1)~(Y-4)の塗布された基板を用い、体積抵抗率評価用導電パターンを作製した。なお、膜厚はプリベーク後0.6μmとし、長方形の透光パターン(10mm×15mm)を有するフォトマスクを介し露光した。
上記の体積抵抗率評価パターンが形成された基板の未露光部分について、透過率評価により、基板上の残渣を評価した。具体的には、未露光部分について、膜形成前後の400nmにおける透過率を、紫外可視分光光度計((株)島津製作所製「MultiSpec-1500(商品名)」)を用いて、測定した。そして、膜形成前の透過率をT0、膜形成後の透過率をTとしたときに、式(T0-T)/T0で表される透過率変化を算出した。透過率変化は好ましくは1.0%未満、より好ましくは0.7%未満である。
まず、炭素単体物および/または炭素化合物で表面被覆された導電性粒子(A-1)80.00g、DISPERBYK21116を6.25g、PGMEA146.25g、DPM150.00gに対し、ホモジナイザーにて、1200rpm、30分の混合処理を施し、さらに、高圧湿式メディアレス微粒化装置ナノマイザー(ナノマイザー(株))を用いて分散して、銀粒子分散体を得た。この銀微粒子分散体382.50gに対し、酸解離性基を有するアルカリ可溶性樹脂(B)を10.00g、金属キレート化合物(C-1)、0.3g、NCI-831を1.20g、PE-3Aを6.00g混合したものに、PGMEA50.00g、DPM50.00gを添加し撹拌することにより、感光性樹脂組成物1を得た。
実施例1と同様の方法で、表1記載の組成の感光性樹脂組成物を得て、それぞれの感光性樹脂組成物について表1~3記載の基板上で実施例1と同様の評価をした。評価結果を、表1~3に示す。なお、表中のガラス基板として無アルカリガラス基板(OA-10G;日本電気硝子株式会社製)を使用した。
Claims (22)
- 炭素単体物および/または炭素化合物で表面被覆された導電性粒子(A)、酸解離性基を有するアルカリ可溶性樹脂(B)および金属キレート化合物(C)を含有する、感光性樹脂組成物。
- 前記金属キレート化合物(C)が、Au、Ag、Cu、Cr、Fe、Co、Ni、Bi、Pb、Zn、Pd、Pt、Al、Ti、Zr、Wおよび/またはMoを含む、請求項1記載の感光性樹脂組成物。
- 前記金属キレート化合物(C)がAl、Zrおよび/またはBiを含む、請求項1または2記載の感光性樹脂組成物。
- 前記金属キレート化合物(C)が、2以上の配位子を含む、請求項1~3のいずれか一項記載の感光性樹脂組成物。
- 前記導電性粒子(A)が、銀を含む、請求項1~4のいずれか一項記載の感光性樹脂組成物。
- 前記導電性粒子(A)の1次粒子径が1~700nmである、請求項1~5のいずれか一項記載の感光性樹脂組成物。
- 請求項1~6のいずれか一項記載の感光性樹脂組成物を基板上に塗布して塗布膜を得る、塗布工程と、
前記塗布膜を乾燥して乾燥膜を得る、乾燥工程と、
前記乾燥膜を露光及び現像してパターンを形成する、露光現像工程と、
前記パターンをポストベークして導電性パターンを得る、ポストベーク工程と、を備える、導電性パターンの製造方法。 - 前記導電性パターンの幅が、5μm以下である、請求項7記載の導電性パターンの製造方法。
- 請求項1~6のいずれか一項記載の感光性樹脂組成物の硬化物からなる導電性パターンを具備する、基板。
- 少なくとも有機成分を含む膜上に、導電性パターンを具備する、請求項9記載の基板。
- 少なくとも基材側から、導電性パターン、有機成分を含む膜、および導電性パターンの積層体を具備する、請求項9または10記載の基板。
- 前記有機成分を含む膜が、アルカリ可溶性樹脂を含有する、請求項10または11記載の基板。
- 前記有機成分を含む膜中のアルカリ可溶性樹脂が、極性基を含有する、請求項12記載の基板。
- 前記有機成分を含む膜中のアルカリ可溶性樹脂が、カルド系樹脂を含有する、請求項12記載の基板。
- 前記有機成分を含む膜中のアルカリ可溶性樹脂が、さらにアクリル樹脂を含み、カルド系樹脂とアクリル樹脂の含有量比(重量比)が1:10~10:1である、請求項14記載の基板。
- 前記有機成分を含む膜が、ポリイミド樹脂、ポリイミドシロキサン樹脂、ポリエーテルスルホン樹脂、ポリベンゾオキサゾール樹脂、アラミド樹脂、エポキシ樹脂および/またはスルホンアミド樹脂を含有する、請求項10~15のいずれか一項記載の基板。
- 前記有機成分を含む膜が、ポリイミド樹脂、ポリイミドシロキサン樹脂、ポリベンゾオキサゾール樹脂および/またはアラミド樹脂を含有する、請求項16記載の基板。
- 少なくとも請求項1~6のいずれか一項記載の感光性樹脂組成物を基板上に塗布、乾燥して得られた膜を露光、現像する工程を備える、タッチパネルの製造方法。
- 少なくとも請求項1~6のいずれか一項記載の感光性樹脂組成物を現像する工程を備える、ディスプレイの製造方法。
- 少なくとも請求項1~6のいずれか一項記載の感光性樹脂組成物を現像する工程を備える、イメージセンサの製造方法。
- 少なくとも請求項1~6のいずれか一項記載の感光性樹脂組成物を現像する工程を備える、有機エレクトロルミネッセンス照明の製造方法。
- 少なくとも請求項1~6のいずれか一項記載の感光性樹脂組成物を現像する工程を備える、太陽電池の製造方法。
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JP6841233B2 (ja) | 2021-03-10 |
CN109791352B (zh) | 2022-07-29 |
KR20190058465A (ko) | 2019-05-29 |
TW201831613A (zh) | 2018-09-01 |
KR102399714B1 (ko) | 2022-05-19 |
TWI797084B (zh) | 2023-04-01 |
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