WO2015111738A1 - Adhésif en forme de film comprenant des particules revêtues de fibres électroconductrices - Google Patents
Adhésif en forme de film comprenant des particules revêtues de fibres électroconductrices Download PDFInfo
- Publication number
- WO2015111738A1 WO2015111738A1 PCT/JP2015/051941 JP2015051941W WO2015111738A1 WO 2015111738 A1 WO2015111738 A1 WO 2015111738A1 JP 2015051941 W JP2015051941 W JP 2015051941W WO 2015111738 A1 WO2015111738 A1 WO 2015111738A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- film
- conductive
- coated particles
- conductive fiber
- film adhesive
- Prior art date
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
- C09J9/02—Electrically-conducting adhesives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/10—Adhesives in the form of films or foils without carriers
-
- 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
-
- 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
- C08K2201/00—Specific properties of additives
- C08K2201/001—Conductive additives
-
- 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
- C08K9/00—Use of pretreated ingredients
- C08K9/02—Ingredients treated with inorganic substances
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/314—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive layer and/or the carrier being conductive
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
- C09J2301/408—Additional features of adhesives in the form of films or foils characterized by the presence of essential components additives as essential feature of the adhesive layer
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2400/00—Presence of inorganic and organic materials
- C09J2400/20—Presence of organic materials
- C09J2400/22—Presence of unspecified polymer
-
- 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
- H10K50/80—Constructional details
- H10K50/84—Passivation; Containers; Encapsulations
- H10K50/842—Containers
- H10K50/8426—Peripheral sealing arrangements, e.g. adhesives, sealants
Definitions
- the present invention relates to a film adhesive containing conductive fiber-coated particles made of a particulate material and a fibrous conductive material.
- the film adhesive is useful as a sheet-like sealing material for semiconductor elements such as organic EL elements.
- An organic electroluminescence (sometimes referred to as “organic EL” in this specification) element is composed of a structure in which a light emitting layer is sandwiched between a pair of counter electrodes, and electrons are injected from one of the electrodes, Holes are injected from the other electrode. Light emission occurs when the injected electrons and holes recombine in the light emitting layer.
- An organic EL device including the organic EL element is expected as a full-color flat panel display or as an alternative to an LED due to high impact resistance and high visibility and a variety of emission colors.
- There are two types of light extraction methods for organic EL devices There are two types of light extraction methods for organic EL devices, a top emission type and a bottom emission type.
- the top emission type is preferable because it has a high aperture ratio and is excellent in light extraction efficiency.
- organic EL elements are more susceptible to moisture than other electronic components, and moisture that penetrates into the organic EL elements can cause electrode oxidation or organic modification, resulting in a significant decrease in light emission characteristics.
- Met As a method for solving this problem, a method of sealing the periphery of the organic EL element with a sealing material having moisture resistance is known.
- the sealing material is disposed in the light extraction direction, it is required to seal with a sealing material having moisture resistance and transparency.
- a method for sealing the periphery of the organic EL element with a moisture-proof sealing material a method of providing a dam around the organic EL element, filling the inside of the dam with a liquid sealing material, and curing it, or a sheet form
- a method in which a sealing material is bonded to an organic EL element and cured is preferable in that the sealing work can be easily performed and contamination of the substrate due to the sealing material flowing out as in the case of using a liquid sealing material can be prevented.
- the organic EL element can be protected without impairing the light extraction efficiency, and the electrodes can be reliably conductively connected.
- a method for imparting conductivity to the sealing material conductive fine particles obtained by coating a metal on the surface of resin fine particles are blended with an insulating curable compound (for example, a thermosetting compound). There is known a method of curing (see Patent Documents 1 to 4).
- the conductive fine particles have a problem that since the entire surface of the resin fine particles is coated with a metal, many expensive metal materials are used and the raw material costs are high. Moreover, since it is necessary to manufacture by special methods, such as an electroplating method and an alternate adsorption method, it was necessary to use a special apparatus or to pass through many processes, and also had the problem that manufacturing cost was high.
- the conductive fine particles are colored because the entire surface is coated with metal, and in addition, in order to impart conductivity to the sealing material, it is necessary to contact the conductive fine particles in the sealing material. As a result, it is difficult to obtain a cured product having both transparency and conductivity as a result of being incorporated in a large amount.
- a method of imparting conductivity while maintaining the transparency of the sealing material a method of coating a conductive ink on the surface of the sealing material or a method of forming a metal wiring or the like can be considered. According to this method, it is possible to impart conductivity while ensuring the transparency of the sealing material, but it is only possible to impart surface conductivity to the surface of the sealing material. It was impossible to develop conductivity in the thickness direction.
- Conductive fiber-coated particles can be obtained easily and inexpensively by mixing particulate matter and fibrous conductive material. Since the conductive fiber-coated particles can impart conductivity by containing a small amount in the cured product, the cured product of the film-like adhesive containing this has excellent conductivity without impairing its transparency ( 2. In particular, having conductivity in the thickness direction) and suppressing an increase in raw material costs. When the conductive fiber-coated particles are added to the film adhesive, the organic EL device can be easily sealed with a cured product having excellent transparency and conductivity (especially conductivity in the thickness direction). Obtaining an adhesive The present invention has been completed based on these findings.
- the present invention provides a film-like adhesive comprising conductive fiber-coated particles (A) containing a particulate substance, and a fibrous conductive substance covering the particulate substance, and a resin (B). To do.
- the present invention also provides the film adhesive, wherein the fibrous conductive material constituting the conductive fiber-coated particles (A) is a conductive nanowire.
- the present invention also provides the film adhesive, wherein the conductive nanowire is at least one selected from the group consisting of metal nanowires, semiconductor nanowires, carbon fibers, carbon nanotubes, and conductive polymer nanowires.
- the present invention also provides the above film adhesive, wherein the conductive nanowire is a silver nanowire.
- the present invention also provides the film adhesive, wherein the content of the conductive fiber-coated particles (A) is 0.01 to 10% by weight of the total amount of the film adhesive.
- the present invention also provides the film adhesive, wherein the median diameter of the particulate material constituting the conductive fiber-coated particles (A) is 70 to 100% of the film adhesive thickness.
- the present invention also provides the film adhesive for sealing a semiconductor element.
- the present invention also provides a sealing sheet obtained by laminating a film substrate on the film adhesive.
- the present invention also provides a cured product obtained by curing the film adhesive.
- the present invention also provides the above cured product having a total light transmittance [converted to a thickness of 10 ⁇ m] in a visible light wavelength region of 87% or more.
- the present invention also provides a semiconductor device in which a semiconductor element is sealed with the cured product.
- a film-like adhesive comprising conductive fiber-coated particles (A) containing a particulate substance, and a fibrous conductive substance covering the particulate substance, and a resin (B).
- a film adhesive according to [1] wherein the fibrous conductive substance constituting the conductive fiber-coated particles (A) is a conductive nanowire.
- the conductive nanowire is at least one selected from the group consisting of metal nanowires, semiconductor nanowires, carbon fibers, carbon nanotubes, and conductive polymer nanowires.
- the film-like adhesive of the present invention makes it easy to bond a semiconductor element to a semiconductor element by directly bonding and curing it without forming a dam around the semiconductor element and filling a liquid sealing material. It can be sealed and has excellent workability.
- the film-like adhesive of the present invention comprises conductive fiber-coated particles that can impart excellent conductivity (especially conductivity in the thickness direction) to a resin molded into a sheet by adding a small amount. Since it contains, the hardened
- the conductive fiber-coated particles can be produced by a simple method without using a special device, and in addition, a large amount of expensive conductive material (material having conductivity) is used as a raw material. There is no need. Therefore, the film adhesive of the present invention can suppress an increase in raw material costs and can be provided at a low cost.
- the conductive fiber-coated particles include conductive fiber-coated particles having flexibility
- the conductive fiber-coated particles having flexibility are deformed following the concavo-convex structure of the semiconductor element. Since it can spread, generation
- the conductive fiber-coated particles of the present invention include a conductive material including a particulate material and a fibrous conductive material that coats the particulate material (sometimes referred to herein as “conductive fiber”). Coated particles.
- “cover” means a state in which the conductive fibers cover part or all of the surface of the particulate matter.
- the particulate matter and the conductive fiber are not necessarily in contact with each other, but usually a part of the conductive fiber is in contact with the surface of the particulate matter. Yes.
- FIG. 1 is an example of a scanning electron microscope image of the conductive fiber-coated particles of the present invention.
- the conductive fiber-coated particles of the present invention at least a part of the particulate material (the true spherical material in FIG. 1) is coated with the conductive fiber (the fibrous material in FIG. 1). It has a configuration.
- the particulate matter constituting the conductive fiber-coated particles of the present invention is a particulate structure.
- the material (raw material) constituting the particulate matter is not particularly limited, and examples thereof include known or commonly used materials such as metal, plastic, rubber, ceramic, glass, and silica. In the present invention, among these, it is preferable to use a transparent material such as transparent plastic, glass, and silica, and it is particularly preferable to use a transparent plastic.
- the transparent plastic includes a thermosetting resin and a thermoplastic resin.
- the thermosetting resin include poly (meth) acrylate resin; polystyrene resin; polycarbonate resin; polyester resin; polyurethane resin; epoxy resin; polysulfone resin; amorphous polyolefin resin; divinylbenzene, hexatriene, divinyl ether, Divinyl sulfone, diallyl carbinol, alkylene diacrylate, oligo or polyalkylene glycol diacrylate, oligo or polyalkylene glycol dimethacrylate, alkylene triacrylate, alkylene tetraacrylate, alkylene trimethacrylate, alkylene tetramethacrylate, alkylene bisacrylamide, alkylene bismethacryl Polyfunctional monomers such as amides and polybutadiene oligomers modified at both ends with acrylic In or polymerized with other monomers network polymer obtained; phenol-formaldehyde resins,
- thermoplastic resin examples include ethylene / vinyl acetate copolymer, ethylene / vinyl acetate / unsaturated carboxylic acid copolymer, ethylene / ethyl acrylate copolymer, ethylene / methyl methacrylate copolymer, and ethylene / acrylic acid.
- Copolymer ethylene / methacrylic acid copolymer, ethylene / maleic anhydride copolymer, ethylene / aminoalkyl methacrylate copolymer, ethylene / vinyl silane copolymer, ethylene / glycidyl methacrylate copolymer, ethylene / hydroxyethyl methacrylate
- Examples include copolymers, methyl (meth) acrylate / styrene copolymers, acrylonitrile / styrene copolymers, and the like.
- the shape of the particulate matter is not particularly limited.
- it is spherical (true spherical, substantially true spherical, elliptical spherical, etc.), polyhedral, rod-like (cylindrical, prismatic, etc.), flat, flake, indefinite Examples include shape.
- the conductive fiber-coated particles can be produced with high productivity, can be easily dispersed uniformly in the resin (B), and can easily impart conductivity to the entire cured product.
- a spherical shape and a rod shape are preferable, and a spherical shape (particularly a true spherical shape) is particularly preferable.
- the average aspect ratio of the particulate matter is not particularly limited, but is preferably less than 20 (for example, 1 or more and less than 20), particularly preferably 1 to 10. When the average aspect ratio exceeds the above range, it may be difficult to develop excellent conductivity in the resin (B) by blending a small amount of the conductive fiber-coated particles.
- the average aspect ratio of the particulate matter is, for example, a sufficient number (for example, 100 or more, preferably 300 or more; in particular, 100 or 300) using an electron microscope (SEM, TEM). It is obtained by taking an electron microscope image of the substance, measuring the aspect ratio of these particulate substances, and arithmetically averaging them.
- the configuration of the particulate matter is not particularly limited, and may be a single layer configuration or a multilayer (multilayer) configuration.
- the particulate material may be any of solid particles, hollow particles, porous particles, and the like.
- the average particle size of the particulate material is 70 to 100% (in particular, 80 to 100%) of the thickness of the film adhesive of the present invention, and has excellent conductivity (particularly conductivity in the thickness direction). Is preferable, for example, 0.1 to 100 ⁇ m, particularly preferably 1 to 50 ⁇ m, and most preferably 5 to 30 ⁇ m.
- the average particle diameter is less than the above range, the thickness of the obtained film-like adhesive becomes thin, so that the sealing performance is deteriorated.
- the average particle diameter exceeds the above range, the thickness of the obtained film-like adhesive is increased, so that the transparency may be lowered.
- the average particle diameter in the long axis (longest long axis) direction is controlled within the above range.
- the average particle diameter of the said particulate matter is a median diameter (D50) by a laser diffraction / scattering method.
- the particulate matter is preferably transparent.
- the total light transmittance in the visible light wavelength region of the particulate matter is not particularly limited, but is preferably 70% or more, and particularly preferably 75% or more. If the total light transmittance is below the above range, the transparency of the film adhesive or its cured product may be lowered.
- the total light transmittance in the visible light wavelength region of the particulate matter is, when the particulate matter is plastic particles, the monomer as the raw material of the particulate matter at a temperature of 80 to 150 ° C. between the glasses. Polymerization is performed in a region to obtain a flat plate having a thickness of 1 mm, and the total light transmittance in the visible light wavelength region of the flat plate is determined according to JIS K7361-1.
- the particulate matter preferably has flexibility, and the 10% compressive strength is, for example, 10 kgf / mm 2 or less, preferably 5 kgf / mm 2 or less, particularly preferably 3 kgf / mm 2 or less.
- Conductive fiber-coated particles containing particulate matter having a 10% compressive strength in the above range are deformed following a fine uneven structure by applying pressure. Therefore, when the film-like adhesive containing the conductive fiber-coated particles is used for sealing an organic EL element having a fine concavo-convex structure, the conductive fiber-coated particles can be distributed in detail, Generation
- the refractive index of the particulate material is not particularly limited, but is preferably 1.4 to 2.7, and particularly preferably 1.5 to 1.8.
- the refractive index of the particulate matter is such that when the particulate matter is plastic particles, the monomer that is the raw material of the particulate matter is polymerized in the temperature range of 80 to 150 ° C., and the length is 20 mm ⁇ width 6 mm.
- a multi-wavelength Abbe refractometer (trade name “DR-M2”, manufactured by Atago Co., Ltd.) with the prism and the test piece in close contact using monobromonaphthalene as an intermediate solution. Can be obtained by measuring the refractive index at 25 ° C. and sodium D line.
- the particulate matter preferably has a small difference in refractive index from the resin (B) described later or a cured product thereof, and the particulate matter and the resin (B) constituting the conductive fiber-coated particles (A) are cured.
- the absolute value of the difference in refractive index between the objects (at 25 ° C. and at a wavelength of 589.3 nm) is preferably 0.02 or less (preferably 0.01 or less, particularly preferably 0.005 or less). That is, the conductive fiber-coated particles (A) and the resin (B) contained in the film adhesive of the present invention preferably satisfy the following formula.
- the coefficient of variation in the volume-based particle size distribution of the particulate matter is calculated from the following equation.
- the particle size distribution can be measured using a particle size distribution measuring device (trade name “Coulter Multisizer”, manufactured by Beckman Coulter, Inc.).
- Coefficient of variation (CV value) (%) (S2 / Dn) ⁇ 100 (In the formula, S2 represents the standard deviation in the volume-based particle size distribution, and Dn represents the median diameter (D50) based on the volume)
- the particulate matter can be produced by a known or common method, and the production method is not particularly limited.
- metal particles it can be produced by a vapor phase method such as a CVD method or a spray pyrolysis method, a wet method using a chemical reduction reaction, or the like.
- plastic particles for example, a method of polymerizing monomers constituting the resin (polymer) exemplified above by a known polymerization method such as a suspension polymerization method, an emulsion polymerization method, a seed polymerization method, or a dispersion polymerization method. Etc. can be manufactured.
- thermosetting resin examples include, for example, trade names “Techpolymer MBX series”, “Techpolymer BMX series”, “Techpolymer ABX series”, “Techpolymer ARX series”, and “Techpolymer AFX series”.
- trade names “Techpolymer MBX series”, “Techpolymer BMX series”, “Techpolymer ABX series”, “Techpolymer ARX series”, and “Techpolymer AFX series”. trade names “Techpolymer MBX series”, “Techpolymer BMX series”, “Techpolymer ABX series”, “Techpolymer ARX series”, and “Techpolymer AFX series”.
- trade names “Micropearl SP”, “Micropearl SI” trade name “Soft Bead” (manufactured by Sumitomo Seika Co., Ltd.), trade name “Duo Master” (manufactured by Sekisui Plastics Co., Ltd.), and the like.
- the conductive fiber constituting the conductive fiber-coated particle of the present invention is a fibrous structure (linear structure) having conductivity.
- the shape of the conductive fiber is not particularly limited as long as it is fibrous (fibrous), but the average aspect ratio is preferably 10 or more (for example, 20 to 5000), particularly preferably 50 to 3000, and most preferably. Is 100-1000. When the average aspect ratio is less than the above range, it may be difficult to develop excellent conductivity by blending a small amount of conductive fiber-coated particles.
- the average aspect ratio of the conductive fiber is determined by the same procedure as that for the average aspect ratio of the particulate matter. Note that the concept of “fibrous” in the conductive fibers includes shapes of various linear structures such as “wire” and “rod”. In the present specification, fibers having an average thickness of 1000 nm or less may be referred to as “nanowires”.
- the average thickness (average diameter) of the conductive fibers is not particularly limited, but is preferably 1 to 400 nm, particularly preferably 10 to 200 nm, and most preferably 50 to 100 nm. When the average thickness is less than the above range, the conductive fibers are likely to aggregate and it may be difficult to produce the conductive fiber-coated particles. On the other hand, if the average thickness exceeds the above range, it may be difficult to coat the particulate matter, and it may be difficult to obtain conductive fiber-coated particles efficiently.
- the average thickness of the conductive fibers is an electron microscope for a sufficient number of conductive fibers (for example, 100 or more, preferably 300 or more; in particular, 100 or 300) using an electron microscope (SEM, TEM). It is obtained by taking an image, measuring the thickness (diameter) of these conductive fibers, and arithmetically averaging them.
- the average length of the conductive fibers is not particularly limited, but is preferably 1 to 100 ⁇ m, particularly preferably 5 to 80 ⁇ m, and most preferably 10 to 50 ⁇ m. If the average length is less than the above range, it may be difficult to coat the particulate matter, and it may not be possible to obtain conductive fiber-coated particles efficiently. On the other hand, if the average length exceeds the above range, the conductive fibers may adhere to or be adsorbed on a plurality of particles, which may cause aggregation (deterioration of dispersibility) of the conductive fiber-coated particles.
- the average length of the conductive fibers is an electron microscope for a sufficient number of conductive fibers (for example, 100 or more, preferably 300 or more; in particular, 100 or 300) using an electron microscope (SEM, TEM). It is calculated
- the material (raw material) constituting the conductive fiber may be a conductive material, and examples thereof include metals, semiconductors, carbon materials, and conductive polymers.
- the metal examples include known or commonly used metals such as gold, silver, copper, iron, nickel, cobalt, tin, and alloys thereof.
- silver is particularly preferable in terms of excellent conductivity.
- Examples of the semiconductor include known or conventional semiconductors such as cadmium sulfide and cadmium selenide.
- Examples of the carbon material include known and commonly used carbon materials such as carbon fibers and carbon nanotubes.
- the conductive polymer examples include polyacetylene, polyacene, polyparaphenylene, polyparaphenylene vinylene, polypyrrole, polyaniline, polythiophene, and derivatives thereof (for example, an alkyl group, a hydroxyl group, a carboxyl group, a common polymer skeleton, And those having a substituent such as ethylenedioxy group; specifically, polyethylenedioxythiophene and the like).
- polyacetylene, polyaniline and derivatives thereof, polypyrrole and derivatives thereof, polythiophene and derivatives thereof are particularly preferable.
- the conductive polymer may contain a known or commonly used dopant (for example, an acceptor such as a halogen, a halide or a Lewis acid; a donor such as an alkali metal or an alkaline earth metal).
- the conductive fiber of the present invention is preferably a conductive nanowire, in particular, at least one conductive nanowire selected from the group consisting of metal nanowires, semiconductor nanowires, carbon fibers, carbon nanotubes, and conductive polymer nanowires, In particular, silver nanowires are most preferable in terms of excellent conductivity.
- the conductive fiber can be produced by a known or conventional production method.
- the metal nanowire can be manufactured by a liquid phase method, a gas phase method, or the like. More specifically, silver nanowires are described in, for example, Mater. Chem. Phys. 2009, 114, p333-338, Adv. Mater. 2002, 14, p833-837, Chem. Mater. 2002, 14, p4736-4745, and the method described in JP-T-2009-505358.
- the gold nanowire can be manufactured, for example, by the method described in JP-A-2006-233252.
- a copper nanowire can be manufactured by the method as described in Unexamined-Japanese-Patent No.
- cobalt nanowire can be manufactured by the method as described in Unexamined-Japanese-Patent No. 2004-148771, for example.
- the semiconductor nanowire can be manufactured by, for example, a method described in JP 2010-208925 A.
- the carbon fiber can be produced, for example, by the method described in JP-A-06-081223.
- the carbon nanotube can be produced, for example, by the method described in JP-A-06-157016.
- the said conductive polymer nanowire can be manufactured by the method of Unexamined-Japanese-Patent No. 2006-241334, Unexamined-Japanese-Patent No. 2010-76044, for example.
- a commercial item can also be used as the conductive fiber.
- the conductive fiber-coated particles (A) can be produced by mixing the above-mentioned particulate material and conductive fibers in a solvent.
- any one of the following methods (1) to (4) Can be manufactured.
- (1) Mixing a dispersion in which the particulate matter is dispersed in a solvent (referred to as “particle dispersion”) and a dispersion in which the conductive fibers are dispersed in a solvent (referred to as “fiber dispersion”). Then, if necessary, the solvent is removed to obtain the conductive fiber-coated particles of the present invention (or a dispersion of the conductive fiber-coated particles).
- the solvent is removed if necessary, and the conductive fiber-coated particles of the present invention (or a dispersion of the conductive fiber-coated particles).
- the solvent is removed if necessary, and the conductive fiber-coated particles of the present invention (or a dispersion of the conductive fiber-coated particles).
- the solvent is removed as necessary to disperse the conductive fiber-coated particles of the present invention (or dispersion of the conductive fiber-coated particles). Liquid).
- the method (1) is preferable because homogeneous conductive fiber-coated particles can be obtained.
- Examples of the solvent used in producing the conductive fiber-coated particles of the present invention include water; alcohols such as methanol, ethanol, propanol, isopropanol, and butanol; acetone, methyl ethyl ketone (MEK), and methyl isobutyl ketone (MIBK).
- alcohols such as methanol, ethanol, propanol, isopropanol, and butanol
- MEK methyl ethyl ketone
- MIBK methyl isobutyl ketone
- Ketones such as benzene, toluene, xylene and ethylbenzene; ethers such as diethyl ether, dimethoxyethane, tetrahydrofuran and dioxane; esters such as methyl acetate, ethyl acetate, isopropyl acetate and butyl acetate; N, N- Examples thereof include amides such as dimethylformamide and N, N-dimethylacetamide; nitriles such as acetonitrile, propionitrile and benzonitrile. These can be used individually by 1 type or in combination of 2 or more types (that is, as a mixed solvent). In the present invention, alcohol and ketone are particularly preferable.
- the resin (B) described later contains a liquid curable compound (for example, an epoxy compound), it can be used as a solvent.
- a liquid curable compound for example, an epoxy compound
- a film-like adhesive containing conductive fiber-coated particles (A) and a resin (B) can be formed without going through a step of removing the solvent.
- the viscosity of the solvent is not particularly limited, but the viscosity at 25 ° C. is preferably 10 cP or less (for example, 0.1 to 10 cP) in that the conductive fiber-coated particles can be efficiently produced, Particularly preferred is 0.1 to 5 cP.
- the viscosity of the solvent at 25 ° C. can be measured using, for example, an E-type viscometer (rotor: 1 ° 34 ′ ⁇ R24, rotation speed: 0.5 rpm, measurement temperature: 25 ° C.).
- the boiling point at 1 atm of the solvent is preferably 200 ° C. or less, particularly preferably 150 ° C. or less, and most preferably 120 ° C. or less, from the viewpoint that the conductive fiber-coated particles can be efficiently produced.
- the content of the particulate matter when mixing the particulate matter and the conductive fiber in the solvent is, for example, about 0.1 to 50 parts by weight, preferably 1 to 30 parts by weight with respect to 100 parts by weight of the solvent.
- the content of the conductive fibers is, for example, about 0.1 to 50 parts by weight, preferably 1 to 30 parts by weight with respect to 100 parts by weight of the solvent.
- the ratio of the particulate matter and the conductive fiber when mixing the particulate matter and the conductive fiber in the solvent is the ratio of the surface area of the particulate matter and the projected area of the conductive fiber [surface area / projected area]
- the ratio is preferably about 100/1 to 100/100, preferably 100/10 to 100/50.
- the surface area of the said particulate matter is calculated
- the projected area of the conductive fiber is a sufficient number (for example, 100 or more, preferably 300 or more; in particular, 100 or 300) using an electron microscope (SEM, TEM). It is obtained by taking an electron microscopic image of the conductive fibers, calculating the projected area of these conductive fibers using an image analyzer, and calculating the arithmetic average.
- SEM electron microscope
- the conductive fiber-coated particles can be obtained as a solid by removing the solvent.
- the removal of the solvent is not particularly limited, and can be performed by a known or conventional method such as heating, distillation under reduced pressure, or the like.
- the solvent is not necessarily removed, and for example, the dispersion of conductive fiber-coated particles (A) can be added to the resin (B) as it is.
- the conductive fiber-coated particles can be produced by mixing raw materials (particulate matter and conductive fibers) in a solvent, and do not require a complicated process. It is advantageous.
- a particulate material having an average particle diameter A [ ⁇ m] and an average length of, for example, A ⁇ 0.5 [ ⁇ m] or more (preferably A ⁇ 1.0 [ ⁇ m ], Particularly preferably, A ⁇ 1.5 [ ⁇ m] or more) can be used to produce conductive fiber-coated particles more efficiently.
- a particulate material having an average circumference B [ ⁇ m] and an average length (B ⁇ 1/6) [ ⁇ m] or more preferably B [ ⁇ m It is preferable to use the above-mentioned conductive fibers.
- the average perimeter of the particulate matter is a sufficient number (for example, 100 or more, preferably 300 or more; in particular, 100, 300, etc.) of particulate matter using an electron microscope (SEM, TEM). It is calculated
- the ratio of the particulate matter and the conductive fiber constituting the conductive fiber-coated particle of the present invention is such that the ratio of the surface area of the particulate matter to the projected area of the conductive fiber [surface area / projected area] is, for example, 100/1 ⁇ A ratio that is about 100/100 (particularly 100/10 to 100/50) is to provide conductivity more efficiently while ensuring the transparency of the film adhesive or its cured product. It is preferable at the point which can do.
- the surface area of the particulate matter and the projected area of the conductive fiber are determined by the above-described methods.
- the conductive fiber-coated particles of the present invention have the above-described configuration, excellent conductivity (particularly, conductivity in the thickness direction) can be imparted by adding a small amount to the cured product, and transparency and conductivity. It is possible to form an excellent cured product.
- grain is made into a fine unevenness
- Conductive fiber-coated particles (A) can be used singly or in combination of two or more.
- the content (blending amount) of the conductive fiber-coated particles (A) in the film adhesive is, for example, about 0.01 to 10 parts by weight, preferably 0.1 to 5 parts per 100 parts by weight of the resin (B). Part by weight, more preferably 0.1 to 2 parts by weight.
- the content of the conductive fiber-coated particles (A) in the film adhesive is preferably 0.01 to 10% by weight, more preferably 0. 0% by weight with respect to the total amount of the film adhesive (100% by weight). It is 1 to 5% by weight, particularly preferably 0.1 to 2% by weight.
- the content (mixing amount) of the particulate matter (particulate matter contained in the conductive fiber-coated fine particles) in the film adhesive is 0.005 to 5% by weight with respect to the total amount of the film adhesive (100% by weight). Is more preferably 0.05 to 2.5% by weight, particularly preferably 0.05 to 1% by weight.
- the content (blending amount) of conductive fibers (conductive fibers contained in the conductive fiber-coated fine particles) in the film-like adhesive is 0.005 to 5% by weight with respect to the total amount of the film-like adhesive (100% by weight). %, More preferably 0.05 to 2.5% by weight, particularly preferably 0.05 to 1% by weight.
- the conductive fiber-coated particles (A) are contained in the above range, a film adhesive excellent in conductivity and transparency or a cured product thereof can be obtained.
- grains (A) is less than the said range, depending on a use, the electroconductivity of a film adhesive or its hardened
- the transparency of the film adhesive or its cured product may be insufficient depending on the application.
- the film-like adhesive of the present invention contains conductive fibers in a state of being coated with particulate matter, it has sufficient conductivity even if the amount of the conductive material is reduced to the above range. Things can be formed. Therefore, the reduction in transparency caused by containing a conductive material can be reduced extremely low, and the raw material costs can be greatly reduced.
- the resin (B) of the present invention can maintain a sheet-like shape at room temperature (5-35 ° C.), and the cured product obtained by curing the resin (B) has transparency. Good.
- the term “having transparency” means that the total light transmittance in a visible light wavelength region of a cured product having a thickness of 10 ⁇ m is, for example, 87% or more, preferably 90% or more.
- the total light transmittance in the visible light wavelength region of the cured product can be measured according to JIS K7361-1.
- Examples of a method for keeping the shape of the resin (B) molded into a sheet shape at room temperature include the following methods. 1. A method of reducing tackiness by blending a curable compound having a cationic polymerizable group and / or a radical polymerizable group in one molecule, which is liquid at room temperature, and a solid resin component at room temperature 2. Two or more types of curable compounds with different curing mechanisms (for example, a curable compound having a cationic polymerizable group in one molecule and a curable compound having a radical polymerizable group in one molecule) are mixed and molded into a sheet shape 2. A method for reducing tackiness by curing only a curable compound that is cured by one of the curing mechanisms. 3.
- Method for reducing tackiness by reacting a part of the cationic polymerizable group or radical polymerizable group after molding a curable compound having a cationic polymerizable group or radical polymerizable group in one molecule into a sheet Method of reducing tackiness by reacting one group of a cation polymerizable group or a radical polymerizable group after molding a curable compound having a cation polymerizable group and a radical polymerizable group in one molecule into a sheet shape
- the resin (B) of the present invention comprises a curable compound having a cationic polymerizable group and / or a radical polymerizable group in one molecule (including a curable compound that is liquid at normal temperature and a resin that is solid at normal temperature). It is preferable to contain at least.
- a curable compound having a cationic polymerizable group and / or a radical polymerizable group in one molecule including a curable compound that is liquid at normal temperature and a resin that is solid at normal temperature. It is preferable to contain at least.
- an epoxy group etc. can be mentioned, for example.
- the radical polymerizable group include a (meth) acryloyl group and a vinyl group.
- curable compound having a cationically polymerizable group in one molecule examples include unsaturated group-containing epoxy compounds (for example, epoxidized polybutadiene, epoxidized butadiene-styrene block copolymer, etc.), copolymerized epoxy compounds (for example, Copolymer of glycidyl methacrylate and styrene, copolymer of glycidyl methacrylate, styrene and methyl methacrylate, copolymer of glycidyl methacrylate and cyclohexylmaleimide, copolymer of 3,4-epoxycyclohexylmethyl (meth) acrylate and styrene, 3 , 4-epoxycyclohexylmethyl (meth) acrylate, copolymer of styrene and methyl methacrylate, etc.), novolac type epoxy compounds (for example, phenol, cresol, phenol
- curable compound having a radical polymerizable group in one molecule examples include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, pentyl (meth) acrylate, and hexyl.
- (Meth) acrylic acid alkyl esters such as (meth) acrylate; 2-hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxybutyl (meth) acrylate, caprocactone-modified 2-hydroxyethyl (meth) acrylate, etc.
- curable compound having a cationically polymerizable group and a radically polymerizable group in one molecule examples include oxetane ring-containing (meth) acrylic acid ester compounds described in JP2012-242459A. .
- the content (blending amount) of the resin (B) in the total amount (100% by weight) of the film adhesive of the present invention is, for example, 50 to 99, 99% by weight, particularly preferably 60 to 99% by weight, most preferably 70 to 98% by weight.
- the content (blending amount) of the curable compound having a cationic polymerizable group and / or a radical polymerizable group in one molecule in the total amount of the resin (B) contained in the film adhesive of the present invention is, for example, 20% by weight or more. It is preferably 20 to 100% by weight, most preferably 40 to 100% by weight.
- the content of the curable compound is less than the above range, when used for sealing an organic EL element, the progress of curing becomes insufficient and the sealing performance tends to be lowered.
- Examples of the resin component that is solid at room temperature when the above method 1 is adopted include, for example, polyamide, polyester, polycarbonate, polyacetal, polyphenylene ether, polyphenylene sulfide, polyether ether ketone, polyallyl ether ketone, and polyamide.
- Examples include imide, polyetherimide, polysulfone, polyethersulfone, olefin resin, styrene resin, (meth) acrylic resin, and polymer alloys containing these resins.
- a solid component at room temperature among curable compounds having a cationic polymerizable group and / or a radical polymerizable group in one molecule can be used. These can be used alone or in combination of two or more.
- the content (blending amount) of the resin component that is solid at room temperature in the total amount (100% by weight) of the film adhesive of the present invention is preferably about 5 to 90% by weight, for example. It is preferably 10 to 80% by weight, and most preferably 20 to 70% by weight. If the content of the resin component that is solid at room temperature is below the above range, it tends to be difficult to maintain the sheet-like shape. On the other hand, when the content of the resin component that is solid at room temperature exceeds the above range, when used for sealing an organic EL element, the progress of curing tends to be insufficient and the sealing performance tends to be lowered.
- the film adhesive of the present invention may contain other components in addition to the conductive fiber-coated particles (A) and the resin (B).
- other components for example, a polymerization initiator, a crosslinking agent, a curing agent, a curing retarder, a curing accelerator, a conductive material other than the conductive fiber-coated particles (A), a filler (organic filler, inorganic filler), Polymerization inhibitor, silane coupling agent, antioxidant, light stabilizer, plasticizer, leveling agent, antifoaming agent, organic solvent, ultraviolet absorber, ion adsorbent, pigment, phosphor, release agent, surfactant And flame retardants.
- the content of other components in the total amount of the film adhesive of the present invention is, for example, 30% by weight or less, preferably 0.1 to 20% by weight, particularly preferably 0.1 to 10% by weight.
- the film adhesive of the present invention preferably contains a polymerization initiator.
- the polymerization initiator may be a light irradiation such as a known or conventional photocationic polymerization initiator (photoacid generator), a thermal cationic polymerization initiator, or the like. It is preferable to use a material that can cause cationic polymerization by heat treatment.
- Examples of the cationic photopolymerization initiator include sulfonium salts such as triarylsulfonium hexafluorophosphate and triarylsulfonium hexafluoroantimonate; diaryliodonium hexafluorophosphate, diphenyliodonium hexafluoroantimonate, bis (dodecylphenyl) iodonium tetrakis ( Pentafluorophenyl) borate, iodonium salts such as iodonium [4- (4-methylphenyl-2-methylpropyl) phenyl] hexafluorophosphate; phosphonium salts such as triphenylphosphonium hexafluorophosphate; and pyridium salts.
- Commercial products such as a trade name “CPI-100P” (manufactured by San Apro Co., Ltd.) can also be used.
- thermal cationic polymerization initiator examples include diazonium salts, iodonium salts, sulfonium salts, phosphonium salts, selenium salts, oxonium salts, ammonium salts, and the like.
- the amount of the polymerization initiator used in the cationic polymerization reaction is 0.1 to 5 with respect to 100 parts by weight of the compound having a cationic polymerizable group contained in the film adhesive (the total amount when containing two or more types). Part by weight is preferred.
- radical polymerization is performed by performing light irradiation or heat treatment of a photo radical polymerization initiator, a thermal radical polymerization initiator or the like as a polymerization initiator. It is preferable to use what can be caused.
- photo radical polymerization initiator examples include trade name “Irgacure 184” (manufactured by Ciba Specialty Chemicals), acetophenone benzyl ketal, benzyl dimethyl ketone, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, dimethoxyacetophenone.
- thermal radical polymerization initiator examples include 2,2′-azobisisobutyronitrile, 2,2′-azobis (2,4-dimethylvaleronitrile), 2,2′-azobis (4-methoxy-2). , 4-dimethylvaleronitrile), dimethyl-2,2′-azobis (2-methylpropionate), 2,2-azobis (isobutyric acid) dimethyl, diethyl-2,2′-azobis (2-methylpropio) Azo), dibutyl-2,2′-azobis (2-methylpropionate); benzoyl peroxide, lauroyl peroxide, t-butylperoxypivalate, 1,1-bis (t-butylperoxy) cyclohexane, etc. And organic peroxides such as hydrogen peroxide. When a peroxide is used as a radical polymerization initiator, a redox initiator may be combined with a reducing agent.
- the amount of the polymerization initiator used in the radical polymerization reaction is 0.1 to 5 with respect to 100 parts by weight of the compound having a radical polymerizable group contained in the film adhesive (total amount when containing two or more types). Part by weight is preferred.
- the resin (B) contains a curable compound having a cationic polymerizable group and / or a radical polymerizable group in one molecule, it can react with the curable compound to form a three-dimensional crosslinked structure.
- An agent may be contained.
- crosslinking agent a compound having two or more groups having reactivity with the cationic polymerizable group and / or the radical polymerizable group (for example, a polyfunctional epoxy compound, a polyfunctional acrylic ester, a polyfunctional amine compound, And polyfunctional acid anhydrides and polyfunctional vinyl compounds). These can be used alone or in combination of two or more.
- the content of the crosslinking agent is, for example, about 0 to 20 parts by weight, preferably 0 to 10 parts by weight with respect to 100 parts by weight of the curable compound.
- curing accelerator examples include 2-methylimidazole, 2-ethylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-phenylimidazole, 1,2-dimethylimidazole, and 2-ethyl-4-methylimidazole.
- conductive material other than conductive fiber-coated particles (A) As the conductive material other than the conductive fiber-coated particles (A) (hereinafter sometimes referred to as “other conductive material”), a known or commonly used conductive substance can be used, and is not particularly limited. For example, you may use the above-mentioned conductive fiber.
- the content (blending amount) of other conductive materials (for example, conductive fibers) in the film adhesive of the present invention is, for example, about 0 to 10 parts by weight, preferably 100 parts by weight of the conductive fiber-coated particles. Is 0 to 5 parts by weight, particularly preferably 0 to 1 part by weight.
- the film-like adhesive of the present invention contains the above-mentioned conductive fiber-coated particles (A) (or a dispersion of conductive fiber-coated particles (A)), a resin (B), and other components as necessary, for example, A composition obtained by mixing uniformly using a generally known mixing device such as a revolving type stirring deaerator, a homogenizer, a planetary mixer, a three roll mill, a bead mill, and an ultrasonic wave.
- a generally known mixing device such as a revolving type stirring deaerator, a homogenizer, a planetary mixer, a three roll mill, a bead mill, and an ultrasonic wave.
- a dispersion of conductive fiber-coated particles (A) obtained by mixing a particulate substance and a fibrous conductive substance in a solvent, a resin (B) and other components as required is applied onto release paper or the like to form a sheet, and then the solvent is evaporated and dried (for example, 1 to 10 at about 50 to 150 ° C.).
- a method of reacting a part of the curable compound by a method such as heating or light irradiation (2) Obtained by stirring and mixing the conductive fiber-coated particles (A) obtained through the following Step A and Step B, the resin (B), and other components as necessary, at a predetermined ratio.
- Step A Step of obtaining a conductive fiber-coated particle dispersion by mixing particulate matter and fibrous conductive material in a solvent
- Step B From the conductive fiber-coated particle dispersion obtained through Step A A step of obtaining conductive fiber-coated particles as a solid by removing the solvent (for example, distillation by heating and / or filtration under reduced pressure).
- the conductive fiber-coated particles (A) are highly dispersed in the resin (B).
- it is preferably discharged while stirring by a screw-type discharge method that discharges the composition by rotating the screw using a discharger having a rotational drive structure such as a screw.
- the rotational speed of the screw, the size of the blade of the screw, and the like are preferably adjusted as appropriate according to the viscosity of the film adhesive, the size of the conductive fiber-coated particles (A), and the like.
- the thickness of the film adhesive of the present invention is not particularly limited as long as the purpose of protecting the semiconductor element can be achieved.
- the thickness is about 0.1 to 100 ⁇ m, preferably 1 to 50 ⁇ m. is there.
- variety and length in the surface direction of the film adhesive of this invention are not restrict
- the film adhesive of the present invention can be suitably used as a sheet-like sealing material.
- the film-like adhesive of the present invention is directly attached to the semiconductor element without passing through a process such as forming a dam around the semiconductor element and filling the liquid sealing material.
- the semiconductor element can be easily sealed, and the workability is excellent.
- the resin (B) contains a curable compound having a cationic polymerizable group and / or a radical polymerizable group in one molecule, after being bonded to a semiconductor element, by cation or radical polymerization, A cured product having excellent transparency and conductivity (particularly conductivity in the thickness direction) can be formed.
- the film adhesive of this invention contains the conductive fiber covering particle
- the semiconductor device is deformed following the concavo-convex structure of the semiconductor element and spreads to details, so that it can be sealed while preventing the occurrence of a portion with poor conductivity, and a semiconductor device having excellent conductivity performance (for example, organic EL) Devices, organic transistors, organic thin-film solar cells, etc.) can be formed.
- organic EL organic EL
- the film adhesive of the present invention contains a curable compound having a cationic polymerizable group and / or a radical polymerizable group in one molecule as the resin (B) and contains a photopolymerization initiator, light irradiation is applied. It can be quickly cured to form a cured product.
- the light irradiation is preferably performed by irradiating light of 500 mJ / cm 2 or more with a mercury lamp or the like. Further, after light irradiation, using an oven or the like, for example, at 40 to 150 ° C. (particularly preferably 60 to 120 ° C., most preferably 80 to 110 ° C.) for 10 to 200 minutes (particularly preferably 30 to 120 minutes). ) It may be heated (post bake).
- the film adhesive of the present invention contains a curable compound having a cationic polymerizable group and / or a radical polymerizable group in one molecule as the resin (B) and contains a thermal polymerization initiator, heat treatment Can be quickly cured to form a cured product.
- heat treatment for example, it is preferable to heat at a temperature of 50 to 180 ° C. for about 5 minutes to 2 hours.
- the cured product obtained by curing the film adhesive of the present invention is excellent in transparency, and the total light transmittance in the visible light wavelength region of the cured product (thickness: 10 ⁇ m) is 87% or more, preferably 90% or more. It is.
- the total light transmittance in the visible light wavelength region of the cured product can be measured according to JIS K7361-1.
- the turbidity (haze) of the cured product (thickness: 10 ⁇ m) is, for example, 5% or less, preferably 2% or less.
- the turbidity of the cured product of the present invention can be measured in accordance with JIS K 7136, JIS K 7361, and ASTM D 1003.
- the cured product obtained by curing the film adhesive of the present invention is excellent in electrical conductivity, and its electrical resistivity (at 25 ° C. and 1 atm) is about 0.1 ⁇ ⁇ cm to 10 M ⁇ ⁇ cm, preferably 0.1 ⁇ ⁇ cm to 1 M ⁇ ⁇ cm.
- the film-like adhesive of the present invention has the above-described configuration, a cured product excellent in transparency and conductivity by sealing an organic EL element (particularly, a top emission type organic EL element) through the following method 1.
- an organic EL element can be sealed, and an organic EL device with a long lifetime and high reliability can be provided.
- the light irradiation and heat treatment methods can be performed by the above methods.
- Process 1 An organic EL element is installed on a substrate, and a lid is attached to the organic EL element installation surface side via the film adhesive of the present invention.
- Process 2 The film adhesive is cured.
- a moisture-proof base material for example, a glass substrate such as soda glass or non-alkali glass; a metal substrate such as stainless steel or aluminum; a polyethylene trifluoride or a polytrifluoride.
- Polyfluorinated ethylene polymers such as chlorinated ethylene chloride (PCTFE), polyvinylidene fluoride (PVDF), copolymers of PCTFE and PVDF, copolymers of PVDF and polyfluoroethylene chloride, polyimides, polycarbonates, dicyclopentadiene Examples thereof include cycloolefin resins such as polyethylene, polyesters such as polyethylene terephthalate, resin substrates such as polyethylene and polystyrene, and the like.
- the organic EL element includes an anode / light emitting layer / negative electrode laminate. If necessary, a passivation film such as a SiN film may be provided.
- the film adhesive of the present invention can form a cured product having both transparency and conductivity. Therefore, if the organic EL element is sealed using the film adhesive of the present invention, it can be protected without lowering the light extraction efficiency, and the electrodes can be reliably conductively connected.
- the organic EL device for example, a display, illumination, etc.
- the organic EL device obtained by the said method is protected by the hardened
- the sealing sheet of the present invention is formed by laminating a film-like base material on the film-like adhesive.
- the sheet for sealing of the present invention includes those having a film-like substrate / film-like adhesive laminate structure and those having a film-like substrate / film-like adhesive / film-like substrate laminate structure.
- the film-like base material is bonded to protect the surface of the film-like adhesive and to prevent blocking, and is peeled off when the film-like adhesive is used.
- the film-like substrate may be a substrate having a single layer structure or a substrate having a multilayer laminate structure of two or more layers.
- the film-like substrate examples include paper or plastic film (for example, polyester such as polyethylene terephthalate, polyethylene, polypropylene, etc., surface-treated with a release agent such as silicone, long chain alkyl, fluorine, or molybdenum sulfide.
- Plastic film made of olefin resin polytetrafluoroethylene, polychlorotrifluoroethylene, polyvinyl fluoride, polyvinylidene fluoride, tetrafluoroethylene / hexafluoropropylene copolymer, chlorofluoroethylene / vinylidene fluoride copolymer 1 type, or 2 or more types can be used for the low adhesive base material etc. which consist of fluorine-type polymers, such as.
- Silver nanowires are manufactured according to the method described in “Materials Chemistry and Physics, vol. 114, p333-338,“ Preparation of Aganorods with high heels by polyol processes ””. The specific procedure is shown below. Ethylene glycol solution of FeCl 3: a (FeCl 3 concentration 6 ⁇ 10 -4 M) 0.5mL, was added to the flask containing the ethylene glycol 6 mL, was heated to 0.99 ° C.. Thereafter, 6 mL of an ethylene glycol mixed solution containing 0.052 M AgNO 3 and 0.067 M polyvinylpyrrolidone was added dropwise to the heated solution.
- FeCl 3 FeCl 3 concentration 6 ⁇ 10 -4 M
- the average diameter (average thickness) and average length of the obtained silver nanowires are measured using a scanning electron microscope (SEM) to measure the diameter (thickness) and length of 100 silver nanowires, and each is arithmetically averaged. The average diameter was 80 nm and the average length was 30 ⁇ m.
- Production Example 2 (Production of conductive fiber-coated fine particles) Dispersion of plastic fine particles (trade name “Micropearl SP”, manufactured by Sekisui Chemical Co., Ltd., average particle size: 8.5 ⁇ m) 0.3 parts by weight in 29.7 parts by weight of ethanol and dispersed. A liquid was prepared. Then, the obtained dispersion of plastic fine particles and 17.4 parts by weight of the dispersion of silver nanowires obtained in Production Example 1 (0.5 part by weight of silver nanowires) were mixed, and then 30 ° C. at 30 ° C. The solvent was removed by stirring while heating for minutes to obtain conductive fiber-coated fine particles.
- plastic fine particles trade name “Micropearl SP”, manufactured by Sekisui Chemical Co., Ltd., average particle size: 8.5 ⁇ m
- the plastic particles (a-1) the surface area per one is 226.9Myuemu 2
- the projected area per one silver nanowires is 2.4 [mu] m 2.
- 20 silver nanowires are adsorbed to one plastic fine particle (a-1).
- Surface area) / projection area of silver nanowire (total projection area) is about 100/15.
- the obtained conductive fiber-coated particles were observed with a scanning electron microscope (SEM) (magnification: 100,000). As a result, as shown in FIG. 1, it was confirmed that the silver nanowires were adsorbed on the surface of the plastic fine particles (the surface of the plastic fine particles was covered with the silver nanowires).
- Example 1 Phenoxy resin (trade name “YP-50S”, manufactured by Nippon Steel & Sumikin Chemical Co., Ltd., weight average molecular weight: 60000) 57 parts by weight, polyfunctional epoxy resin (trade name “1032H60”, manufactured by Mitsubishi Chemical Co., Ltd.) 48 parts by weight 5 parts by weight of a bisphenol A type epoxy compound (trade name “jER828”, manufactured by Mitsubishi Chemical Corporation, weight average molecular weight: 370), cationic polymerization initiator (trade name “CPI-100P”, manufactured by San Apro Co., Ltd.) 3
- a composition (1) was obtained by blending 0.5 parts by weight of the conductive fiber-coated particles obtained in Production Example 2 with parts by weight.
- composition (1) was applied to a PET film (thickness: 80 ⁇ m) with one surface treated using an applicator and dried with hot air at 70 ° C. for 10 minutes to obtain a film adhesive (1) (width 2 mm, thickness 10 ⁇ m).
- the obtained film adhesive (1) was bonded to the surface of a conductive glass substrate (manufactured by Luminescence Technology, size: 25 mm ⁇ 25 mm, ITO: 0.14 ⁇ m), and the PET film was peeled off. Further, a conductive glass substrate is bonded onto the film adhesive, UV irradiation (irradiation amount: 2000 mJ / cm 2 ) is performed, and then post baking is performed at 100 ° C. for 5 minutes to obtain a film thickness of 8.5 ⁇ m. A cured product 1 having a sealing material layer was obtained.
- Example 2 450 parts by weight of a glycidyl group-containing acrylate copolymer resin (trade name “HTR-860P-3”, manufactured by Nagase ChemteX Corporation, weight average molecular weight: 800,000), hydrogenated bisphenol A type epoxy resin (trade name “ 5. 89 parts by weight of EPICONEXA-7015 "(manufactured by DIC), 4.51 parts by weight of curing agent (trade name” XLC-LL “, manufactured by Mitsui Chemicals, Inc., phenol aralkyl resin), curing accelerator (trade name” trade name " Curazole 2PZ-CN ", Shikoku Kasei Kogyo Co., Ltd.
- a glycidyl group-containing acrylate copolymer resin trade name “HTR-860P-3”, manufactured by Nagase ChemteX Corporation, weight average molecular weight: 800,000
- hydrogenated bisphenol A type epoxy resin trade name “ 5. 89 parts by weight of EPICONEX
- composition (2) 0.242 parts by weight, cyclohexanone (Wako Pure Chemical Industries, Ltd., special grade) 64 parts by weight, and conductive fiber coated particles obtained in Production Example 2 0.5 part by weight was blended to obtain a composition (2).
- the obtained composition (2) was applied to a PET film (thickness: 80 ⁇ m) with one surface treated using an applicator and dried with hot air at 110 ° C. for 15 minutes to obtain a film adhesive (2) (width 2 mm, thickness 10 ⁇ m).
- the obtained film adhesive (2) was bonded to the surface of a conductive glass substrate (manufactured by Luminescence Technology, size: 25 mm ⁇ 25 mm, ITO: 0.14 ⁇ m), and the PET film was peeled off. Furthermore, the hardened
- micropearl AU the surface of a particulate material composed of a crosslinked polymer containing divinylbenzene as a main component was gold-plated, trade name “Micropearl AU- 2085 ”, manufactured by Sekisui Chemical Co., Ltd., average particle size: 7.3 ⁇ m
- Comparative Example 2 The same procedure as in Example 1 was performed except that the conductive fiber-coated particles obtained in Production Example 2 were not used.
- the film adhesive of the present invention can be easily sealed by bonding and curing directly on the semiconductor element, and is excellent in workability. Moreover, the hardened
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Dispersion Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Conductive Materials (AREA)
- Adhesive Tapes (AREA)
Abstract
L'invention concerne : un adhésif en forme de film, un élément semi-conducteur pouvant être scellé aisément par le collage de l'adhésif en forme de film sur l'élément semi-conducteur et l'élément semi-conducteur pouvant être scellé par un produit durci présentant une excellente transparence et une excellente conductivité électrique (en particulier une conductivité électrique dans la direction de l'épaisseur) ; et un dispositif semi-conducteur dans lequel un élément semi-conducteur est scellé par le produit durci de l'adhésif en forme de film. Cet adhésif en forme de film est caractérisé par l'inclusion de particules revêtues de fibres électroconductrices (A), comprenant un matériau particulaire et un matériau électroconducteur fibreux pour revêtir le matériau particulaire, et d'une résine (B). Des nanofils électroconducteurs, en particulier des nanofils en argent, sont préférés comme matériau électroconducteur fibreux constituant les particules revêtues de fibres électroconductrices (A).
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JP2015559156A JP6434428B2 (ja) | 2014-01-23 | 2015-01-19 | 導電性繊維被覆粒子を含むフィルム状接着剤 |
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JP2014-010771 | 2014-01-23 | ||
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PCT/JP2015/051941 WO2015111738A1 (fr) | 2014-01-23 | 2015-01-19 | Adhésif en forme de film comprenant des particules revêtues de fibres électroconductrices |
Country Status (3)
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JP (1) | JP6434428B2 (fr) |
TW (1) | TWI640595B (fr) |
WO (1) | WO2015111738A1 (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107102489A (zh) * | 2017-06-20 | 2017-08-29 | 深圳市华星光电技术有限公司 | 一种异方性导电胶、导电球及其制作方法 |
JP2021504907A (ja) * | 2017-12-01 | 2021-02-15 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | グラフェン系導電性接着剤の方法およびその用途 |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2019092960A1 (fr) | 2017-11-13 | 2019-05-16 | 日東電工株式会社 | Composition pour liaison par frittage, feuille pour liaison par frittage et bande de découpage en dés pourvue d'une feuille pour liaison par frittage |
CN114381223B (zh) * | 2022-03-24 | 2022-07-12 | 天津六0九电缆有限公司 | 一种半导电胶及复合电缆 |
TWI807879B (zh) * | 2022-06-24 | 2023-07-01 | 國立宜蘭大學 | 奈米纖維薄膜之製作方法 |
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JP2006049369A (ja) * | 2004-07-30 | 2006-02-16 | Denso Corp | 電極接合構造及びその接合方法並びに導電性接着剤及びその製造方法 |
JP2006054066A (ja) * | 2004-08-10 | 2006-02-23 | Toray Ind Inc | 導電性粒子および異方導電性材料用組成物 |
KR100888324B1 (ko) * | 2007-05-04 | 2009-03-12 | 앰코 테크놀로지 코리아 주식회사 | 도전성 접착제의 제조방법 |
JP2011138711A (ja) * | 2009-12-28 | 2011-07-14 | Panasonic Electric Works Co Ltd | 透明導電性接着剤及び透明導電性接着剤から形成される透明導電性接着層を備える光電変換素子 |
WO2012126391A1 (fr) * | 2011-03-22 | 2012-09-27 | Nano And Advanced Materials Institute Limited | Nanomatériaux adhésifs de fixation de puce (daas) haute performance pour led à luminosité élevée |
WO2014017658A1 (fr) * | 2012-07-24 | 2014-01-30 | 株式会社ダイセル | Particule revêtue de fibre conductrice, composition durcissable et article durci dérivé de la composition durcissable |
Family Cites Families (1)
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JP5875311B2 (ja) * | 2011-09-30 | 2016-03-02 | 三菱マテリアル株式会社 | 導電性粒子およびその用途 |
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2015
- 2015-01-19 JP JP2015559156A patent/JP6434428B2/ja not_active Expired - Fee Related
- 2015-01-19 WO PCT/JP2015/051941 patent/WO2015111738A1/fr active Application Filing
- 2015-01-21 TW TW104101896A patent/TWI640595B/zh not_active IP Right Cessation
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JPH11241054A (ja) * | 1997-10-28 | 1999-09-07 | Sony Chem Corp | 異方導電性接着剤および接着用膜 |
JP2006049369A (ja) * | 2004-07-30 | 2006-02-16 | Denso Corp | 電極接合構造及びその接合方法並びに導電性接着剤及びその製造方法 |
JP2006054066A (ja) * | 2004-08-10 | 2006-02-23 | Toray Ind Inc | 導電性粒子および異方導電性材料用組成物 |
KR100888324B1 (ko) * | 2007-05-04 | 2009-03-12 | 앰코 테크놀로지 코리아 주식회사 | 도전성 접착제의 제조방법 |
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WO2012126391A1 (fr) * | 2011-03-22 | 2012-09-27 | Nano And Advanced Materials Institute Limited | Nanomatériaux adhésifs de fixation de puce (daas) haute performance pour led à luminosité élevée |
WO2014017658A1 (fr) * | 2012-07-24 | 2014-01-30 | 株式会社ダイセル | Particule revêtue de fibre conductrice, composition durcissable et article durci dérivé de la composition durcissable |
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Publication number | Priority date | Publication date | Assignee | Title |
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CN107102489A (zh) * | 2017-06-20 | 2017-08-29 | 深圳市华星光电技术有限公司 | 一种异方性导电胶、导电球及其制作方法 |
JP2021504907A (ja) * | 2017-12-01 | 2021-02-15 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | グラフェン系導電性接着剤の方法およびその用途 |
Also Published As
Publication number | Publication date |
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JP6434428B2 (ja) | 2018-12-05 |
TWI640595B (zh) | 2018-11-11 |
TW201533206A (zh) | 2015-09-01 |
JPWO2015111738A1 (ja) | 2017-03-23 |
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