WO2012053373A1 - Composition adhésive conductrice, dispositif électronique, et procédé de production du dispositif électronique - Google Patents

Composition adhésive conductrice, dispositif électronique, et procédé de production du dispositif électronique Download PDF

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WO2012053373A1
WO2012053373A1 PCT/JP2011/073143 JP2011073143W WO2012053373A1 WO 2012053373 A1 WO2012053373 A1 WO 2012053373A1 JP 2011073143 W JP2011073143 W JP 2011073143W WO 2012053373 A1 WO2012053373 A1 WO 2012053373A1
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layer
conductive
electronic device
adhesive composition
photoelectric conversion
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PCT/JP2011/073143
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English (en)
Japanese (ja)
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豪志 武藤
和恵 上村
邦久 加藤
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リンテック株式会社
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    • 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
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/10—Homopolymers or copolymers of methacrylic acid esters
    • 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
    • C09J11/08—Macromolecular 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
    • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
    • C09J9/02—Electrically-conducting adhesives
    • 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
    • H10K71/50—Forming devices by joining two substrates together, e.g. lamination techniques
    • 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
    • H10K71/60—Forming conductive regions or layers, e.g. electrodes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/301—Details of OLEDs
    • H10K2102/331—Nanoparticles used in non-emissive layers, e.g. in packaging layer
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
    • H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof

Definitions

  • the present invention relates to a conductive pressure-sensitive adhesive composition, an electronic device, and a method for producing an electronic device.
  • an organic photoelectric conversion or electro-optic conversion device represented by an organic thin film solar cell is usually produced by laminating an organic semiconductor material on an electrode made of a transparent conductive film.
  • Various conductive films such as metal thin films, metal oxide thin films, and conductive nitride thin films have been studied as transparent conductive films, but at present, both transparency and conductivity can be achieved and durability is excellent. Therefore, metal oxide thin films are the mainstream.
  • indium oxide (ITO) doped with tin is well-balanced between transparency and conductivity, and is widely used (Patent Document 1).
  • Patent Document 2 there is a sheet in which a fine metal mesh or grid is formed on a transparent substrate such as polyethylene terephthalate (PET) (Patent Document 2). Since these sheets can be controlled in transparency and conductivity depending on the mesh design (opening ratio determined by pitch and line width), they can be used as transparent electrodes.
  • electronic devices such as organic thin film devices have been conventionally laminated with a layer made of an organic element material, such as a vacuum deposition method and a wet process represented by a dry process or coating similar thereto, or a laminate via an adhesive layer. It has been manufactured by a process (Patent Document 3).
  • a transparent conductive film having adhesiveness is desired, but in the conventional transparent conductive film, balance of transparency, adhesiveness and conductivity is a problem. Therefore, as a conductive component, a layer composed of a conductive polymer such as a conductive organic polymer compound such as polythiophene or a derivative thereof and a conductive polymer adhesive containing an organic additive is used as a transparent conductive film. It has been proposed to manufacture an electronic device by a laminating process (see Patent Document 4 and Non-Patent Document 1). However, the above-described method has a problem that the performance of the electronic device is deteriorated, for example, the carrier injection efficiency at the laminate interface is lowered or the adhesive force at the interface is low.
  • a method of using an aqueous conductive resin emulsion obtained by polymerizing an aromatic monomer having a hetero atom in the presence of polyvinyl alcohol containing a sulfonic acid group as an adhesive conductive film is disclosed.
  • the conductive film formed from this emulsion has a high surface resistivity for use as an electronic device, and may not provide sufficient performance as an electronic device.
  • This invention is made
  • the objective of this invention is providing the manufacturing method of the electroconductive adhesive composition which solved the above problems, an electronic device, and an electronic device. .
  • the present invention provides the following (1) a conductive adhesive composition comprising a conductive organic polymer compound and an aqueous emulsion adhesive, (2) The conductive adhesive composition according to (1), wherein the conductive organic polymer compound is at least one selected from polyanilines, polypyrroles, polythiophenes, and derivatives thereof, (3) The conductive adhesive composition according to (1), wherein the conductive organic polymer compound is a derivative of polythiophene, (4) The conductive pressure-sensitive adhesive composition according to any one of (1) to (3), wherein the water-based emulsion pressure-sensitive adhesive is an acrylic emulsion pressure-sensitive adhesive.
  • the conductive pressure-sensitive adhesive composition is the above ( 1) An electronic device characterized by being a conductive adhesive composition according to any one of (4), (6) The method for producing an electronic device according to (5), wherein a step of forming an anode laminate by forming a conductive layer on the anode layer using the conductive adhesive composition, on the cathode layer Forming a cathode laminate by forming the photoelectric conversion layer on the substrate, and bonding the surface of the cathode conversion layer of the cathode laminate and the conductive layer of the anode laminate.
  • a manufacturing method is provided.
  • the conductive pressure-sensitive adhesive composition of the present invention has excellent transparency by adding a conductive organic polymer compound to a water-based emulsion pressure-sensitive adhesive, and the conductive layer formed from the conductive pressure-sensitive adhesive composition has excellent transparency. Since the surface resistivity is low, it can be used as a conductive layer of an electronic device. In addition, since the conductive layer itself has adhesiveness, it is possible to manufacture an electronic device by a laminating process. In the method for producing an electronic device of the present invention, since the conductive layer formed from the conductive adhesive composition and the photoelectric conversion layer are bonded together, the electronic device can be easily produced by a laminating process.
  • the metal layer becomes uneven or a metal layer is formed.
  • the photoelectric conversion layer is not damaged by the energy of time, and the performance of the electronic device is not deteriorated.
  • FIG. 1A is a schematic view showing a cross section of an example of an electronic device having a conductive layer of the present invention.
  • FIG. 1B is a schematic view showing the production of the electronic device of the present invention.
  • 2 is a current-voltage curve measured for the electronic device 1 obtained in Example 1.
  • FIG. 6 is a current-voltage curve measured for the electronic device 2 obtained in Example 2.
  • 6 is a current-voltage curve measured for the electronic device 3 obtained in Example 3.
  • ⁇ Conductive organic polymer compound As the conductive organic polymer compound, at least one selected from polyanilines, polypyrroles, polythiophenes, and derivatives thereof, which are conductive organic polymer compounds having conductivity by ⁇ -electron conjugation, is used.
  • Polyanilines are high molecular weight compounds of compounds in which the 2-position, 3-position or N-position of aniline is substituted with an alkyl group having 1 to 18 carbon atoms, an alkoxy group, an aryl group, a sulfonic acid group or the like.
  • Methyl aniline poly 3-methyl aniline, poly 2-ethyl aniline, poly 3-ethyl aniline, poly 2-methoxy aniline, poly 3-methoxy aniline, poly 2-ethoxy aniline, poly 3-ethoxy aniline, poly N-methyl aniline Poly N-propyl aniline, poly N-phenyl-1-naphthyl aniline, poly 8-anilino-1-naphthalene sulfonic acid, poly 2-aminobenzene sulfonic acid, poly 7-anilino-4-hydroxy-2-naphthalene sulfonic acid Etc.
  • the polyaniline derivatives include those obtained by doping or mixing the above-mentioned polyanilines with a dopant.
  • halide ions such as chloride ion, bromide ion and iodide ion; perchlorate ion; tetrafluoroborate ion; hexafluoroarsenate ion; sulfate ion; nitrate ion; thiocyanate ion; hexafluoride Silicate ion; Phosphate ion such as phosphate ion, phenyl phosphate ion, hexafluorophosphate ion; trifluoroacetate ion; alkylbenzenesulfonate ion such as tosylate ion, ethylbenzenesulfonate ion, dodecylbenzenesulfonate ion; methylsulfone Alkyl sulfonate ions such as acid ions and ethyl sulfonate ions; or poly
  • polyacrylic acid ion polyvinyl sulfonic acid ion
  • polyvinyl sulfonic acid ion from the point that high conductivity can be obtained and it has a hydrophilic skeleton useful for retaining water molecules and is easily dispersed in water.
  • Polymer ions such as polystyrene sulfonate ion (PSS) and poly (2-acrylamido-2-methylpropane sulfonate) ion are preferred, and polystyrene sulfonate ion (PSS) which is a water-soluble and strongly acidic polymer is more preferred.
  • Polypyrroles are high molecular weight compounds of compounds in which 1-position, 3-position or 4-position of pyrrole is substituted with an alkyl group or alkoxy group having 1 to 18 carbon atoms, such as poly 1-methyl pyrrole, poly 3 -Methyl pyrrole, poly 1-ethyl pyrrole, poly 3-ethyl pyrrole, poly 1-methoxy pyrrole, 3-methoxy pyrrole, poly 1-ethoxy pyrrole, poly 3-ethoxy pyrrole, etc.).
  • Examples of the derivatives of polypyrroles include those obtained by doping or mixing the aforementioned polypyrroles with a dopant. As the dopant, those described above can be used.
  • Polythiophenes are high molecular weight compounds of compounds in which the 3-position or 4-position of thiophene is substituted with an alkyl group or alkoxy group having 1 to 18 carbon atoms, such as poly-3-methylthiophene, poly-3-ethylthiophene, poly Examples thereof include polymers such as 3-methoxythiophene, poly-3-ethoxythiophene, and poly (3,4-ethylenedioxythiophene) (PEDOT).
  • Examples of the derivatives of polythiophenes include those obtained by doping or mixing the above polythiophenes with a dopant. As a dopant, what was illustrated by the above-mentioned [0009] can be used.
  • poly (thiophene) derivatives include poly (3) from the viewpoint that high conductivity can be obtained, a hydrophilic skeleton useful for retaining water molecules, and easy dispersion in water.
  • PEDOT 4-ethylene oxide thiophene
  • PSS polystyrene sulfonate ions
  • the water-based emulsion pressure-sensitive adhesive is not particularly limited as long as it has film-forming properties and has pressure-sensitive adhesive properties, such as acrylic emulsion pressure-sensitive adhesive, vinyl acetate-based emulsion pressure-sensitive adhesive, and ethylene-vinyl acetate copolymer-based emulsion pressure-sensitive adhesive. Is mentioned. Among these, an acrylic emulsion pressure-sensitive adhesive is preferable from the viewpoint that weatherability, heat resistance, oil resistance and the like can be imparted in addition to tackiness and transparency.
  • Acrylic emulsion pressure-sensitive adhesive is composed mainly of an acrylic copolymer, uses water as a dispersion medium, and is usually unsaturated (meth) acrylic acid alkyl ester etc. using various emulsifiers.
  • a monomer and, if desired, a functional group-containing monomer and other monomers can be produced by emulsion polymerization.
  • the (meth) acrylic acid alkyl ester is preferably a (meth) acrylic acid ester having an alkyl group having 1 to 20 carbon atoms, specifically, methyl (meth) acrylate, ethyl (meth) acrylate, ( (Meth) propyl acrylate, (meth) butyl acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isooctyl (meth) acrylate, Examples include decyl (meth) acrylate, dodecyl (meth) acrylate, myristyl (meth) acrylate, palmityl (meth) acrylate, stearyl (meth) acrylate, and the like. These may be used alone or in combination of two or more.
  • Examples of the functional group-containing monomer include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, ( (Meth) acrylic acid hydroxyalkyl esters such as 3-hydroxybutyl (meth) acrylate and 4-hydroxybutyl (meth) acrylate; acetoacetoxymethyl (meth) acrylate; acrylamide, methacrylamide, N-methylacrylamide, N, Acrylamides such as N-dimethylacrylamide, N-methylmethacrylamide, N, N-dimethylmethacrylamide, N-methylolacrylamide, N-methylolmethacrylamide, diacetoneacrylamide; (meth) acrylic acid mono or dimethyl Aminoethyl, (meth) a Mono- or dialkylaminoalkyl (meth) acrylates such as mono- or diethylaminoethyl crylate
  • the functional group-containing monomers may be used alone or in combination of two or more.
  • the functional group-containing monomer is usually preferably 0.1 to 5.0% by mass, preferably 0.3 to 5.0% by mass, and preferably 0.5 to 3.0% by mass with respect to the total amount of monomers. It is further preferable to include it. Within this range, the stability of the conductive pressure-sensitive adhesive composition and the adhesion between the conductive layer formed from the conductive pressure-sensitive adhesive composition and the photoelectric conversion layer described later are good.
  • Examples of other monomers include vinyl esters such as vinyl acetate and vinyl propionate; olefins such as ethylene, propylene, and isobutylene; halogenated olefins such as vinyl chloride and vinylidene chloride; styrene, ⁇ -methylstyrene, and the like. Styrene monomers; diene monomers such as butadiene, isoprene and chloroprene; nitrile monomers such as acrylonitrile and methacrylonitrile. These may be used alone or in combination of two or more.
  • the other monomer is usually preferably 0.1 to 5.0% by mass, preferably 0.3 to 5.0% by mass, and preferably 1.0 to 3.0% by mass with respect to the total amount of monomers. % Is more preferable.
  • emulsifier those usually used for emulsion polymerization can be used, and are not particularly limited.
  • an anion having a radical polymerizable functional group such as vinyl group, propenyl group, isopropenyl group, vinyl ether group, allyl ether group, etc.
  • Known emulsifiers such as type, nonionic type reactive emulsifier, or non-reactive emulsifier are used.
  • non-reactive emulsifier examples include sodium lauryl sulfate, ammonium lauryl sulfate, sodium dodecylbenzenesulfonate, polyoxyethylene sodium lauryl sulfate, polyoxyethylene alkyl ether sodium sulfate, polyoxyethylene alkylphenyl ether ammonium sulfate, and polyoxyethylene alkylphenyl Anionic emulsifiers such as sodium ether sulfate and sodium polyoxyethylene alkyl sulfosuccinate, for example, nonionic systems such as polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene fatty acid ester, polyoxyethylene polyoxypropylene block polymer And emulsifiers.
  • anionic reactive emulsifier examples include commercially available products such as “ADEKA rear soap SE-20N”, but are not particularly limited as long as they have reactivity.
  • nonionic reactive emulsifier examples include commercially available products such as “ADEKA rear soap NE-10”. However, the nonionic reactive emulsifier is not particularly limited as long as it has reactivity.
  • the amount of these emulsifiers used is preferably 0.1 to 8.0 parts by weight, preferably 0.5 to 5.0 parts by weight, based on 100 parts by weight of the monomer mixture as an active ingredient (a component excluding solvents and various additives). Part is more preferable.
  • the amount used is within this range, the emulsion polymerization stability, the storage stability of the resulting aqueous emulsion adhesive, and the mechanical stability are good.
  • the conditions for emulsion polymerization are not particularly limited, and the conditions applied in normal emulsion polymerization can be applied as they are.
  • the temperature is increased while stirring under reflux, and the polymerization is carried out in the temperature range of about 40 to 100 ° C. for about 1 to 8 hours.
  • a polymerization initiator is usually used.
  • azo compounds such as 2,2′-azobis (2-methylpropionamidine) dihydrochloride, persulfates such as potassium persulfate, and peroxides such as benzoyl peroxide can be used. .
  • the concentration of the acrylic copolymer in the acrylic emulsion adhesive is usually preferably 30 to 70% by mass.
  • the weight average molecular weight of the acrylic copolymer is preferably 100,000 to 3,000,000, more preferably 400,000 to 2,000,000 in terms of adhesive performance.
  • the water-based emulsion pressure-sensitive adhesive is not strongly basic.
  • the conductive organic polymer compound may be deposited when the conductive organic polymer compound is blended.
  • the liquid property of the water-based emulsion pressure-sensitive adhesive is preferably less than pH 13.
  • the average particle diameter of the emulsion particles of the water-based emulsion pressure-sensitive adhesive is about 100 to 500 nm, preferably 100 to 300 nm.
  • an adhesive having an excellent balance of emulsion polymerization stability, storage stability of the resulting emulsion, and mechanical stability can be obtained. If the average particle diameter is within this range, stable emulsion particles can be obtained, and the amount of emulsifier used can be prevented from increasing.
  • the average particle size of the emulsion particles can be controlled by the type and concentration of the emulsifier added during polymerization, the concentration of the polymerization initiator, and the like.
  • the water-based emulsion pressure-sensitive adhesive is, as necessary, an antifoaming agent, an antiseptic, a rust-proofing agent, a solvent, a tackifier, a stabilizer, and a thickener, as long as the effects of the present invention are not impaired.
  • Various known additives such as a crosslinking agent, a plasticizer, a wetting agent, a filler such as an inorganic powder or a metal powder, a pigment, a colorant, and an ultraviolet absorber can be added.
  • the conductive adhesive composition of the present invention is a composition containing the conductive organic polymer compound and an aqueous emulsion adhesive.
  • the blending ratio is 1 to 300 parts by weight, preferably 10 to 250 parts, more preferably 15 to 150 parts by weight for the conductive organic polymer compound with respect to 100 parts by weight (in terms of solid content) of the water-based emulsion adhesive.
  • the glass transition temperature of the conductive pressure-sensitive adhesive composition of the present invention is preferably in the range of ⁇ 50 to 50 ° C. from the viewpoint of easy production of an electronic device described later.
  • the electronic device of the present invention has a conductive layer formed from a conductive pressure-sensitive adhesive composition.
  • the thickness of the conductive layer is preferably 5 to 500 nm, more preferably 30 to 300 nm. If it is less than 5 nm, adhesiveness does not appear, and if it exceeds 500 nm, the conductivity is lowered.
  • the surface resistivity of the conductive layer is preferably 1 to 1.0 ⁇ 10 9 ⁇ / ⁇ . More preferably, it is 1 to 1.0 ⁇ 10 4 ⁇ / ⁇ . When the surface resistivity is 1.0 ⁇ 10 9 ⁇ / ⁇ or more, the conductivity is lowered, and the performance as an electronic device is deteriorated.
  • the surface resistivity can be measured by a known method.
  • the transparency of the conductive layer can be evaluated by the total light transmittance of the anode laminate.
  • the total light transmittance of the anode laminate is a value of the total light transmittance of the conductive layer for convenience.
  • the total light transmittance of the conductive layer is preferably 70 to 100%. When the total light transmittance is within this range, transparency as an electronic device is sufficient.
  • the total light transmittance can be measured by a known method.
  • the electronic device of this invention arrange
  • organic devices such as an organic transistor, organic memory, and organic EL; Liquid crystal display; Electronic paper; Thin-film transistor; Electrochromic; Electrochemiluminescence device; Touch panel; Display; Solar cell; Piezoelectric conversion device; electricity storage device; and the like.
  • FIG. 1 (a) each layer which comprises the electronic device of this invention is demonstrated in order with FIG. 1 (a).
  • 1 is an anode layer
  • 4 is a conductive layer
  • 3 is a photoelectric conversion layer
  • 2 is a cathode layer.
  • the material of the anode layer 1 is preferably a material having a small energy barrier and a relatively large work function with respect to the HOMO level of a p-type organic semiconductor or intrinsic semiconductor layer described later.
  • a conductive metal oxide can be used as a material of the anode layer 1.
  • the conductive metal oxide include tin-doped indium oxide (ITO), iridium oxide (IrO 2 ), indium oxide (In 2 O 3 ), tin oxide (SnO 2 ), fluorine-doped tin oxide (FTO), and indium oxide.
  • conductive metal oxides can be preferably formed by sputtering.
  • the thickness of the anode layer 1 is preferably 10 to 300 nm, and particularly preferably 30 to 150 nm, from the viewpoint that both transparency and conductivity can be achieved.
  • the photoelectric conversion layer 3 is a layer that performs photoelectric conversion, and is formed from an organic semiconductor from the viewpoints of cost reduction, flexibility, ease of formation, high extinction coefficient, weight reduction, impact resistance, and the like of raw materials. A layer is preferred.
  • the photoelectric conversion layer 3 may be composed of a single layer or a plurality of layers. In the case of a single layer, the photoelectric conversion layer 3 is usually formed from an intrinsic semiconductor layer (i-type semiconductor). In the case of a plurality of layers, a stack of (p-type semiconductor layer / n-type semiconductor layer) or (p-type semiconductor layer / intrinsic semiconductor layer / n-type semiconductor layer) is used.
  • the thickness of the photoelectric conversion layer 3 differs depending on whether it is a single layer or a plurality of layers, but it is generally preferably 30 nm to 2 ⁇ m from the viewpoint of not inhibiting efficient light absorption and carrier movement. In particular, the thickness is preferably 40 nm to 300 nm.
  • An intrinsic semiconductor layer is an organic layer having a pn junction interface made of a p-type semiconductor material and an n-type semiconductor material.
  • the material of the intrinsic semiconductor layer include a first material composed of at least one of fullerene, fullerene derivatives, semiconducting carbon nanotubes (CNT) and CNT compounds, a polyphenylene vinylene (PPV) derivative, or a polythiophene-based material. It is possible to use a mixture in which the second material made of a molecular material is mixed so that the obtained semiconductor becomes an intrinsic semiconductor.
  • fullerene derivative for example, [6,6] -phenyl-C61-butyric acid methyl ester (PCBM) can be used, and a fullerene dimer or an alkali metal or alkaline earth metal is introduced.
  • PCBM phenyl-C61-butyric acid methyl ester
  • a fullerene compound or the like can also be used.
  • CNT carbon nanotubes or the like including fullerene or metal-encapsulated fullerene can be used.
  • a CNT compound in which various molecules are added to the side wall or tip of the CNT can also be used.
  • polyphenylene vinylene poly [2-methoxy, 5- (2′-ethyl-hexyloxy) -p-phenylene-vinylene] (MEH-PPV) or the like can be used.
  • polythiophene polymer material Poly (3-alkylthiophene) such as poly-3-hexylthiophene (P3HT), dioctylfluorene-bithiophene copolymer (F8T2), and the like can be used.
  • a particularly preferable intrinsic semiconductor is a mixture of PCBM and P3HT mixed at a mass ratio of 1: 0.3 to 1: 4.
  • the material of the p-type semiconductor layer is not particularly limited as long as it is an electron-donating material.
  • polyalkylthiophene and derivatives thereof, polyphenylene and derivatives thereof, polyphenylene vinylene and derivatives thereof, polysilane and Examples thereof include porphyrin derivatives, phthalocyanine derivatives, and organometallic polymers.
  • polyalkylthiophene and its derivatives are preferable.
  • these organic materials may be used independently and the mixture which combined 2 or more types may be sufficient.
  • n-type semiconductor layer The material of the n-type semiconductor layer is not particularly limited as long as it is an electron-accepting material.
  • NTCDA 1,4,5,8-naphthalenetetracarboxylic dianhydride
  • PTCDA 3, 4,9,10-perylenetetracarboxylic dianhydride
  • PTCBI 3,4,9,10-perylenetetracarboxylic bisbenzimidazole
  • PTCBI 3, N′-dioctyl-3,4,9,10- Naphthyltetracarboxydiimide
  • PPD 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole
  • PPD 2,5-di (1- Oxazole derivatives such as naphthyl) -1,3,4-oxadiazole (BND), 3- (4-biphenylyl) -4-phenyl-5
  • NTCDA 1,4,5,8-
  • fullerene derivatives are particularly preferable because they are n-type semiconductor materials that are stable and have high carrier mobility. In addition, you may use these materials individually or in combination of 2 or more types.
  • the fullerene derivative is not particularly limited, and for example, [6,6] -phenyl-C61-butyric acid methyl ester (PCBM) can be used. [6,6] -Phenyl-C61-butyric acid methyl ester (PCBM) or the like can be used, and a fullerene dimer or a fullerene compound into which an alkali metal or an alkaline earth metal is introduced may be used. it can.
  • a material of the cathode layer 2 As a material of the cathode layer 2, a material having a small energy barrier and a relatively small work function with respect to the LUMO level of the n-type semiconductor or the intrinsic semiconductor layer is preferable.
  • metals such as platinum, gold, aluminum, iridium, chromium, and zinc oxide, metal oxides or alloys, carbon nanotubes, or composites of carbon nanotubes and the above metals, metal oxides, or alloys can be given.
  • the thickness of the cathode layer 2 is preferably 20 nm to 1 ⁇ m, particularly preferably 30 to 200 nm.
  • both the anode layer 1 and the cathode layer 2 are preferably provided on a substrate.
  • the substrate glass (plate) or plastic (plate or film) is generally used.
  • the plastic film include films made of resins such as polyethylene terephthalate, polyethylene naphthalate, tetraacetylcellulose, syndiotactic polystyrene, polyphenylene sulfide, polycarbonate, polyarylate, polysulfone, polyestersulfone, polyetherimide, and cyclic polyolefin. Among them, those excellent in mechanical strength, durability, transparency and the like are preferable.
  • the thickness of the substrate is generally 3 ⁇ m to 5 mm, preferably 5 ⁇ m to 1 mm, particularly preferably 10 ⁇ m to 300 ⁇ m, from the viewpoint of mechanical strength, durability and transparency.
  • the method for producing an electronic device of the present invention includes a step of forming an anode laminate by forming a conductive layer made of the conductive adhesive composition on the anode layer, and forming the photoelectric conversion layer on the cathode layer.
  • FIG. 1B 1 is an anode layer
  • 4 is a conductive layer
  • 3 is a photoelectric conversion layer
  • 2 is a cathode layer.
  • a structure in which the anode layer 1 and the conductive layer 4 are integrated is referred to as an anode laminate.
  • What integrated the cathode layer 2 and the photoelectric converting layer 3 is called a cathode laminated body.
  • the downward arrow indicates that the anode laminate and the cathode laminate are bonded and integrated to form an electronic device.
  • the anode laminate is formed by forming the conductive layer 4 made of the conductive adhesive composition of the present invention on the anode layer 1.
  • the anode layer 1 is preferably provided on a substrate. Examples of the substrate include those described above.
  • PVD physical vapor deposition
  • CVD chemical vapor deposition
  • thermal CVD thermal CVD
  • atomic layer deposition ALD
  • dry processes such as dip coating, spin coating, spray coating, bar coating, gravure coating, die coating, doctor blade and other wet processes such as electrochemical deposition, etc. It is selected as appropriate.
  • the formation method for forming the conductive layer 4 on the anode layer 1 includes various processes such as dip coating, spin coating, spray coating, bar coating, gravure coating, die coating, and doctor blade, and wet processes such as electrochemical deposition. Are selected as appropriate.
  • the cathode laminate is formed by forming the photoelectric conversion layer 3 on the cathode layer 2.
  • the cathode layer 2 is preferably provided on a substrate.
  • PVD physical vapor deposition
  • CVD chemical vapor deposition
  • thermal CVD thermal CVD
  • atomic layer deposition A dry process or the like can be used, and is appropriately selected depending on the material of the cathode layer 2.
  • the formation method for forming the photoelectric conversion layer 3 on the cathode layer 2 is PVD (physical vapor deposition) such as vacuum deposition, sputtering, ion plating, or CVD (chemical vapor deposition) such as thermal CVD or atomic layer deposition (ALD).
  • PVD physical vapor deposition
  • CVD chemical vapor deposition
  • thermal CVD thermal CVD
  • atomic layer deposition ALD
  • the material of the photoelectric conversion layer 3 includes a dry process such as phase deposition) or a wet process such as various coatings such as dip coating, spin coating, spray coating, gravure coating, and bar coating doctor blade, and electrochemical deposition. It is appropriately selected depending on.
  • the surface of the photoelectric conversion layer 3 of the cathode laminate and the surface of the conductive layer 4 of the anode laminate are bonded together to manufacture an electronic device. Since the conductive layer 4 of the anode laminate has excellent adhesiveness, the conductive layer 4 and the photoelectric conversion layer 3 can be favorably bonded together by bonding to the surface of the photoelectric conversion layer 3.
  • the surface of the photoelectric conversion layer 3 and the surface of the conductive layer 4 are bonded together, they may be bonded at room temperature, and are bonded while being heated to a temperature higher than the temperature at which the conductive adhesive composition is softened. You may combine them.
  • the photoelectric conversion layer 3 and the conductive layer 4 are preferably bonded to each other while being heated from the viewpoint that the photoelectric conversion layer 3 and the conductive layer 4 can be bonded well and good rectification characteristics for functioning as an electronic device can be obtained.
  • the temperature at which the conductive pressure-sensitive adhesive composition is softened is a temperature equal to or higher than the glass transition temperature (Tg) of the conductive pressure-sensitive adhesive composition. Specifically, it is about 80 to 150 ° C. from the viewpoint of easy production.
  • Tg glass transition temperature
  • a known laminating method can be used as a known laminating method.
  • the electronic device can be easily produced by a laminating process. it can. Further, in this method, there is no step of forming the cathode layer 2 on the photoelectric conversion layer 3 after the photoelectric conversion layer 3 is formed, and the cathode layer 2 becomes non-uniform or the cathode layer 2 is formed. Since the photoelectric conversion layer 3 is not damaged by the energy of time, the performance of the electronic device is not deteriorated.
  • a conductive organic polymer compound a mixture of poly (3,4-ethylenedioxythiophene) (PEDOT) and polystyrene sulfonate ion (PSS) (hereinafter referred to as PEDOT: PSS) water 10 parts by weight of a dispersion (manufactured by Japan Agfa Material Co., Ltd., product name: HBS-5, solid content: 1.1% by mass) was added and stirred at room temperature to make uniform, thereby preparing a conductive adhesive composition 1. .
  • PEDOT polystyrene sulfonate ion
  • ITO glass manufactured by Technoprint Co., Ltd., surface resistivity 14 ⁇ / ⁇ ] was prepared by sputtering on a glass plate so that tin-doped indium oxide (ITO) had a thickness of 150 nm. .
  • ITO tin-doped indium oxide
  • the surface of the ITO glass was immersed in a neutral detergent for ultrasonic cleaning, boiled in 2-propanol, and further cleaned with a UV-ozone cleaner (manufactured by Filgen, product name “UV253E”). .
  • the conductive pressure-sensitive adhesive composition 1 is dropped on the anode layer of ITO glass, spin-coated (rotation speed: 1500 rpm, time: 60 seconds), and then dried at 100 ° C. for 10 minutes to conduct electricity.
  • a conductive layer made of an adhesive composition was formed.
  • the film thickness of the conductive layer was measured by the product name “F20” manufactured by Filmetrics.
  • the film thickness of the conductive layer was 160 nm.
  • the film thickness of an Example and a comparative example is the value measured using said apparatus.
  • PCBM poly-3-hexylthiophene
  • P3HT poly-3-hexylthiophene
  • a solution photoelectric conversion layer forming solution in which C61-butyric acid methyl ester was dissolved to 0.75% by mass was prepared.
  • this liquid was filtered through a filter having a pore diameter of 0.45 ⁇ m, dropped onto the cathode layer (aluminum layer) of the PET film, spin-coated at 2500 rpm for 60 seconds, allowed to stand at room temperature for 30 minutes, and then at 100 ° C.
  • a heat treatment was performed for 10 minutes to form a photoelectric conversion layer having a thickness of 120 nm.
  • the temperature of the roller was set to 120 ° C. with the surface of the conductive layer of the obtained anode laminate and the surface of the photoelectric conversion layer of the cathode laminate.
  • the electronic device 1 was obtained by pressure bonding while heating.
  • Example 2 A conductive pressure-sensitive adhesive composition 2 was prepared in the same procedure as in Example 1 except that the water-based emulsion pressure-sensitive adhesive was changed to 0.5 parts by mass and the PEDOT: PSS aqueous dispersion was changed to 10 parts by mass. Obtained (the thickness of the conductive layer was 140 nm).
  • Example 3 A conductive pressure-sensitive adhesive composition 3 was prepared in the same procedure as in Example 1 except that the water-based emulsion pressure-sensitive adhesive was changed to 0.25 parts by mass and the PEDOT: PSS aqueous dispersion was changed to 10 parts by mass. Obtained (the thickness of the conductive layer was 165 nm).
  • Example 4 A conductive pressure-sensitive adhesive composition 4 was prepared in the same procedure as in Example 1 except that the water-based emulsion pressure-sensitive adhesive was changed to 0.1 parts by mass and the PEDOT: PSS aqueous dispersion was changed to 10 parts by mass. Obtained (the thickness of the conductive layer was 145 nm).
  • Example 5 Instead of PEDOT: PSS aqueous dispersion, 1.0 part by mass of an aqueous emulsion adhesive, instead of PEDOT: PSS aqueous dispersion, polyaniline aqueous dispersion [manufactured by Nissan Chemical Industries, product name: D1033W, solid content 2.5 [Mass%]
  • a conductive pressure-sensitive adhesive composition 5 was prepared in the same procedure as in Example 1 except that 4 parts by mass were added, to obtain an electronic device 5 (the thickness of the conductive layer was 170 nm).
  • aqueous emulsion adhesive is added to 1.0 part by mass, and as a conductive organic polymer compound, instead of PEDOT: PSS aqueous dispersion, a polypyrrole aqueous dispersion (manufactured by Sigma-Aldrich, product name: 482552, solid content 5 mass%)
  • a conductive pressure-sensitive adhesive composition 6 was prepared in the same procedure as in Example 1 except that 2 parts by mass were added, and an electronic device 6 was obtained (the film thickness of the conductive layer was 190 nm).
  • a water-based emulsion pressure-sensitive adhesive was not added, and only 10 parts by mass of PEDOT: PSS as a conductive organic polymer was used as a comparative composition 1 and compared in the same procedure as in Example 1.
  • An electronic device 1 was obtained (the film thickness of the layer made of the composition 1 for comparison was 40 nm).
  • PEDOT: PSS was not added as the conductive organic polymer, and only the water-based emulsion pressure-sensitive adhesive was used as the comparative composition 2, and the comparative electrons were prepared in the same procedure as in Example 1.
  • Device 2 was obtained (the film thickness of the layer made of Comparative Composition 2 was 100 nm).
  • Compositions of conductive adhesive compositions 1 to 6 obtained in Examples 1 to 6, comparative compositions obtained in Comparative Examples 1 and 2, and electronic devices 1 to 6 obtained in Examples 1 to 6 The characteristics of the comparative electronic devices 1 and 2 obtained in Example 6 and Comparative Examples 1 and 2 were measured and shown in Table 1.
  • the conductive layer of the example has excellent adhesiveness, bonding of the conductive layer and the photoelectric conversion layer can be obtained by bonding the adhesive conductive layer to the photoelectric conversion layer by a laminating process. , Confirmed to function as an electronic device.
  • the layer composed of the comparative composition 1 of Comparative Example 1 is excellent in transparency, conductivity, and film formability, but has no adhesiveness, so that the bonding property of the photoelectric conversion layer is poor and rectifying. An electronic device could not be obtained.
  • the layer which consists of the composition 2 for a comparison of the comparative example 2 was able to join with a photoelectric converting layer, when it was used as an electronic device with a high surface resistivity, a favorable rectification characteristic was acquired. There wasn't.
  • the conductive adhesive composition of the present invention has excellent adhesiveness and low surface resistivity, organic devices such as organic transistors, organic memories, and organic ELs; liquid crystal displays; electronic paper; thin film transistors; electrochromic An electrochemiluminescence device; a touch panel; a display; a solar cell; a thermoelectric conversion device; a piezoelectric conversion device; an electricity storage device; Furthermore, it is useful in the field of electronic devices by a laminating process.
  • Anode layer 2 Cathode layer 3: Photoelectric conversion layer 4: Conductive layer

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Laminated Bodies (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

La présente invention concerne le problème de fourniture d'un dispositif électronique dans lequel une couche conductrice possède une excellente adhésivité et une faible résistivité de surface et un procédé de production de celui-ci. Le problème est résolu par une composition adhésive conductrice, un dispositif électronique et un procédé de production du dispositif électronique. La composition adhésive conductrice contient un composé polymère organique conducteur et une composition adhésive d'émulsion à base d'eau. Le dispositif électronique comprend une couche anodique, une couche conductrice formée de la composition adhésive conductrice, une couche de conversion photoélectrique, et une couche de cathode disposées dans cet ordre, caractérisées en ce que la composition adhésive conductrice est une composition adhésive d'émulsion à base d'eau contenant un composé polymère organique conducteur. Le procédé de production pour le dispositif électronique est caractérisé en ce qu'il inclut : une étape de formation d'une structure stratifiée d'anode par formation, sur une couche anodique, d'une couche conductrice utilisant la composition adhésive conductrice ; une étape de formation d'une structure stratifiée de cathode par formation de la couche de conversion photoélectrique sur une couche de cathode ; et une étape d'adhérence de la surface de la couche de conversion photoélectrique de la structure stratifiée de cathode à la surface de la couche conductrice de la structure stratifiée d'anode.
PCT/JP2011/073143 2010-10-22 2011-10-06 Composition adhésive conductrice, dispositif électronique, et procédé de production du dispositif électronique WO2012053373A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012124336A (ja) * 2010-12-08 2012-06-28 Dainippon Printing Co Ltd 有機薄膜太陽電池の製造方法
US9353298B2 (en) 2012-10-09 2016-05-31 Lg Chem, Ltd. Acrylic emulsion pressure sensitive adhesive composition including nanometer scale latex particles with monomodal particle size distribution and method of preparing the same
WO2017142074A1 (fr) * 2016-02-19 2017-08-24 積水化学工業株式会社 Transducteur photoélectrique à jonction solide et son procédé de production

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59227966A (ja) * 1983-06-08 1984-12-21 Hitachi Chem Co Ltd 導電性粘着剤の製造方法
JPH02115290A (ja) * 1988-10-24 1990-04-27 Denki Kagaku Kogyo Kk 導電性粘着剤
JPH03227386A (ja) * 1990-01-31 1991-10-08 Sekisui Chem Co Ltd 水性エマルジョン型導電性粘着剤
JP2007051173A (ja) * 2005-08-15 2007-03-01 Shin Etsu Polymer Co Ltd 帯電防止性粘接着剤、帯電防止性粘接着層および保護材
JP2007204689A (ja) * 2006-02-03 2007-08-16 Seiko Pmc Corp 水性導電性樹脂エマルション
JP2008106243A (ja) * 2006-09-29 2008-05-08 Diatex Co Ltd 易剥離性粘着テープの製造方法
JP2009500832A (ja) * 2005-06-30 2009-01-08 ザ リージェンツ オブ ザ ユニバーシティー オブ カリフォルニア 導電性ポリマー接着剤、導電性ポリマー接着剤を使用して生成されるデバイス、及び製造方法
WO2009070504A2 (fr) * 2007-11-26 2009-06-04 3M Innovative Properties Company Feuille adhésive et son procédé de fabrication
JP2010163586A (ja) * 2008-03-04 2010-07-29 Lintec Corp 粘着剤組成物及び粘着シート

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59227966A (ja) * 1983-06-08 1984-12-21 Hitachi Chem Co Ltd 導電性粘着剤の製造方法
JPH02115290A (ja) * 1988-10-24 1990-04-27 Denki Kagaku Kogyo Kk 導電性粘着剤
JPH03227386A (ja) * 1990-01-31 1991-10-08 Sekisui Chem Co Ltd 水性エマルジョン型導電性粘着剤
JP2009500832A (ja) * 2005-06-30 2009-01-08 ザ リージェンツ オブ ザ ユニバーシティー オブ カリフォルニア 導電性ポリマー接着剤、導電性ポリマー接着剤を使用して生成されるデバイス、及び製造方法
JP2007051173A (ja) * 2005-08-15 2007-03-01 Shin Etsu Polymer Co Ltd 帯電防止性粘接着剤、帯電防止性粘接着層および保護材
JP2007204689A (ja) * 2006-02-03 2007-08-16 Seiko Pmc Corp 水性導電性樹脂エマルション
JP2008106243A (ja) * 2006-09-29 2008-05-08 Diatex Co Ltd 易剥離性粘着テープの製造方法
WO2009070504A2 (fr) * 2007-11-26 2009-06-04 3M Innovative Properties Company Feuille adhésive et son procédé de fabrication
JP2010163586A (ja) * 2008-03-04 2010-07-29 Lintec Corp 粘着剤組成物及び粘着シート

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012124336A (ja) * 2010-12-08 2012-06-28 Dainippon Printing Co Ltd 有機薄膜太陽電池の製造方法
US9353298B2 (en) 2012-10-09 2016-05-31 Lg Chem, Ltd. Acrylic emulsion pressure sensitive adhesive composition including nanometer scale latex particles with monomodal particle size distribution and method of preparing the same
WO2017142074A1 (fr) * 2016-02-19 2017-08-24 積水化学工業株式会社 Transducteur photoélectrique à jonction solide et son procédé de production

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