WO2012043025A1 - 導電性接着剤組成物、電子デバイス、陽極積層体及び電子デバイスの製造方法 - Google Patents
導電性接着剤組成物、電子デバイス、陽極積層体及び電子デバイスの製造方法 Download PDFInfo
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- WO2012043025A1 WO2012043025A1 PCT/JP2011/066493 JP2011066493W WO2012043025A1 WO 2012043025 A1 WO2012043025 A1 WO 2012043025A1 JP 2011066493 W JP2011066493 W JP 2011066493W WO 2012043025 A1 WO2012043025 A1 WO 2012043025A1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
- C08L2203/204—Applications use in electrical or conductive gadgets use in solar cells
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
- Y10T428/2804—Next to metal
Definitions
- the present invention relates to a conductive adhesive composition, an electronic device, an anode laminate, and an electronic device manufacturing method. About.
- an organic photoelectric conversion or electro-optic conversion device represented by an organic thin film solar cell is usually produced by laminating a 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, it is possible to achieve both light transmission and conductivity, and it is also durable.
- Metal oxide thin films are the mainstream because of their superiority.
- indium oxide (ITO) doped with tin is widely used because it has a good balance between light transmittance and conductivity, and it is easy to form an electrode fine pattern by wet etching using an acid solution ( 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 PET (Patent Document 2). These sheets can be used as transparent electrodes because the translucency and conductivity can be controlled depending on the mesh design (opening ratio determined by pitch and line width).
- electronic devices are conventionally manufactured by a vacuum deposition method, a dry process or similar wet process represented by coating, or a laminating process via an adhesive layer when laminating layers made of organic element materials. (Patent Document 3).
- the present inventors have conducted intensive studies, and as a result, the above-mentioned problems can be solved by adding a specific organic additive together with the conductive organic polymer compound to the water-soluble polyvinyl polymer.
- the present invention has been completed.
- the present invention is a conductive adhesive composition
- a conductive adhesive composition comprising the following (1) (A) water-soluble polyvinyl polymer, (B) an organic additive, and (C) a conductive organic polymer compound, (B)
- the organic additive is at least one selected from water-soluble polyhydric alcohols, water-soluble pyrrolidones or hydrophilic aprotic solvents, and (C) the conductive organic polymer compound is polyaniline, polypyrrole or A conductive adhesive composition characterized by being at least one selected from polythiophenes and derivatives thereof;
- T1 glass transition temperature of the water-soluble polyvinyl polymer
- T2 melting point of the organic additive
- the boiling point of the organic additive at 0.101 MPa (760 mmHg) is T3, T2 ⁇ T1 ⁇ T3
- the conductive adhesive composition according to (1) which satisfies (3)
- the conductive adhesive composition of the present invention is obtained by adding a specific (co) polymer and a specific organic additive to a conductive organic polymer compound. It has a low surface resistance, is highly transparent, and can be used as a conductive layer for electronic devices. Moreover, since the conductive layer made of the conductive adhesive composition of the present invention itself has excellent adhesiveness, an electronic device can be manufactured by a lamination process.
- 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 a method for manufacturing an electronic device of the present invention.
- FIG. 2 is a graph showing the relationship between current density and voltage in a solar cell which is one of the electronic devices of the present invention.
- the conductive adhesive composition is for imparting sufficient adhesion to a conductive layer made of a conductive adhesive composition without reducing the conductivity of the conductive layer.
- the water-soluble polyvinyl polymer also includes a warm water-soluble polyvinyl polymer.
- the glass transition temperature (Tg) of the water-soluble polyvinyl polymer is preferably in the range of ⁇ 50 to 150 ° C., preferably 20 to 140 ° C., more preferably 30 from the viewpoints of film formability, adhesion, and handling. -130 ° C, more preferably 40-120 ° C.
- the water-soluble polyvinyl polymer has a structural unit of —CH 2 —CH (R) — in the polymer.
- the structure unit is not particularly limited as long as it has at least 30 mol% or more in the polymer.
- the water-soluble polyvinyl polymer may be a homopolymer containing this structural unit or a copolymer.
- R is any one of a hydroxyl group, a carboxyl group, a pyrrolidone group, and an acrylamide group.
- Those having a carboxyl group in the polymer are those having a structural unit of —CH 2 —CH (COOH) —.
- Specific examples of the water-soluble polyvinyl polymer having a carboxyl group include polyacrylic acid (PAA).
- PAA polyacrylic acid
- Those having a hydroxyl group in the polymer are those having a structural unit of —CH 2 —CH (OH) —.
- water-soluble polyvinyl polymer having a hydroxyl group examples include, for example, polyvinyl alcohol (PVA), polyvinyl alcohol-ethylene copolymer, polyvinyl alcohol- (N-vinylformamide) copolymer, polyvinyl alcohol-vinyl acetate copolymer. Examples include coalescence.
- the water-soluble polyvinyl polymer having a hydroxyl group may be partially saponified or completely saponified. The degree of saponification is preferably 20 to 100 mol%, more preferably 35 to 100 mol%, still more preferably 40 to 100 mol%. When the saponification degree is less than 20 mol%, the solubility is lowered.
- the water-soluble polyvinyl polymer having a pyrrolidone group has a structural unit of —CH 2 —CH (NC 4 O) —, and specific examples thereof include, for example, polyvinyl pyrrolidone (PVP), N-vinyl-2- Examples include pyrrolidone-ethylene copolymer and N-vinyl-2-pyrrolidone-vinyl acetate copolymer.
- the water-soluble polyvinyl polymer having an acrylamide group has a structural unit of —CH 2 —CH (CONH 2 ) —, and specific examples thereof include polyacrylamide and the like.
- the water-soluble polyvinyl polymer has a functional group such as a hydrophobic group, a cationic group, an anionic group including a sulfonic acid group, a thiol group, a carbonyl group, and a silanol group other than the above structural units for the purpose of imparting various functions. You may contain in.
- these water-soluble polyvinyl polymers those in which R is any one of a hydroxyl group, a carboxyl group, and a pyrrolidone group are preferable, and PVA, PVP, and PAA are preferable because an electronic device described later can be easily manufactured.
- the weight average molecular weight (Mw) of the water-soluble polyvinyl polymer is usually 500 to 500,000, preferably 500 to 300,000, more preferably 1,000 to 200,000, and 3,000 to 15 More preferably, it is 10,000. When the Mw of the water-soluble polyvinyl polymer is within this range, sufficient film formability and adhesiveness are exhibited in the electronic device and anode laminate of the present invention.
- the Mw is a standard polystyrene conversion numerical value measured by gel permeation chromatography (GPC).
- the other ethylenically unsaturated monomer which can be copolymerized may be copolymerized 1 type (s) or 2 or more types. .
- Examples of other copolymerizable ethylenically unsaturated monomers include: Carboxylic acids such as vinyl formate, vinyl acetate, vinyl propionate, isopropenyl acetate, vinyl valelate, vinyl caprate, vinyl caprate, vinyl laurate, vinyl stearate, vinyl benzoate, vinyl versatate, vinyl pivalate Vinyl ester monomers; olefins such as ethylene, propylene, butylene; aromatic vinyls such as styrene and ⁇ -methylstyrene; methacrylic acid, fumaric acid, maleic acid, itaconic acid, monoethyl fumarate, maleic anhydride, anhydrous Ethylenically unsaturated carboxylic acid monomers such as itaconic acid; methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate
- the organic additive of component (B) is at least one selected from water-soluble polyhydric alcohols, water-soluble pyrrolidones, and hydrophilic aprotic solvents.
- the organic additive is added for the purpose of improving conductivity. Although details are unknown, by adding such an organic additive, the orientation of the conductive organic polymer compound of the component (C) described later is improved, so that the conductivity is improved.
- the organic additive of component (B) those having a boiling point of 100 ° C. or higher at 1.101 MPa (760 mmHg) are preferable.
- boiling point is below 100 ° C.
- the organic additive volatilizes and scatters during the mixing process of the conductive adhesive composition, during storage, and in various heating processes when manufacturing electronic devices described later, resulting in a reduction in the blending ratio. Since the effect which improves electroconductivity falls, it is not preferable.
- a more preferred boiling point is in the range of 120 to 300 ° C., more preferably 140 to 300 ° C.
- water-soluble polyhydric alcohol that is one of the organic additives of component (B) include glycerin, diglycerin, polyglycerin, ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, 1,3-butanediol, 1, 4-butanediol, erythritol, sorbitol, sorbitan, glucose, maltitol, polyethylene glycol, 1,2-butylene glycol, 1,3-butylene glycol, 2,3-butylene glycol, 3-methyl-1,3-butylene glycol , Tetramethylene glycol, 1,2-pentanediol, 1,2-hexanediol, trimethylolpropane, pentaerythritol, methyl glucoside, polypropylene glycol, xylitol, trehalose, maltitol, man Tall and their alkylene oxide derivatives and the like, may be used alone or in
- Water-soluble pyrrolidones that are one of the organic additives of component (B) include N-methylpyrrolidone, N-ethylpyrrolidone, N-propylpyrrolidone, N-isopropylpyrrolidone, N-butylpyrrolidone, Nt-butyl Pyrrolidone, N-pentylpyrrolidone, N-hexylpyrrolidone, N-heptylpyrrolidone, N-cyclohexylpyrrolidone, N-octylpyrrolidone, N- (2-ethylhexyl) pyrrolidone, N-phenylpyrrolidone, N-benzylpyrrolidone, phenethylpyrrolidone, 2 -Methoxyethyl pyrrolidone, 2-methoxypropyl pyrrolidone, 2-hydroxypropyl pyrrolidone, vinyl
- an aprotic solvent is added as one of the component (B) organic additives.
- the aprotic solvent is blended in the conductive adhesive composition without volatilization / scattering.
- the hydrophilic aprotic solvent which is one of the organic additives of the component (B) include dimethyl sulfoxide and N, N-dimethylformamide.
- the component (B) is preferably selected in combination with the component (A) so as to satisfy the following relationship. That is, the glass transition temperature (Tg) of the water-soluble polyvinyl polymer of component (A) is T1, the melting point of the organic additive of component (B) is T2, and the boiling point at 0.101 MPa (760 mmHg) of the organic additive is T3. In such a case, the combination satisfies T2 ⁇ T1 ⁇ T3.
- the glass transition temperature T1 of the water-soluble vinyl polymer of the component (A) is a value measured by a [differential scanning calorimetry (DSC) measuring instrument].
- water-soluble polyhydric alcohol of component (B) that satisfy the above relationship with component (A) include, for example, glycerin [melting point T2: 18 ° C., boiling point T3: 290 ° C.], Ethylene glycol [melting point T2: ⁇ 11.5 ° C., boiling point T3: 197 ° C.], diethylene glycol [melting point T2: ⁇ 6.5 ° C., boiling point T3: 245 ° C.], propylene glycol [melting point T2: ⁇ 59 ° C., boiling point T3: 188.2 ° C.], dipropylene glycol [melting point T2: ⁇ 40 ° C., boiling point T3: 232 ° C.], 1,3-butanediol [melting point T2: ⁇ 50 ° C., boiling point T3: 207.5 ° C.], 1,4 -Butanediol [melting point T2: 19 ° C., boiling
- glycerin and 1,4-butanediol are preferable from the viewpoint of improving conductivity and adhesiveness.
- the water-soluble pyrrolidone derivative of component (B) include N-methylpyrrolidone [melting point T2: ⁇ 24 ° C., boiling point T3: 202 ° C.], vinylpyrrolidone [melting point T2: 13.5 ° C., boiling point T3: 214. 5 ° C], 2-pyrrolidone [melting point T2: 24.6 ° C, boiling point T3: 245 ° C], and the like.
- hydrophilic aprotic solvents examples include dimethyl sulfoxide (DMSO) [melting point T2: 19 ° C., boiling point T3: 189 ° C.], N, N-dimethylformamide (DMF) [melting point T2: ⁇ 61 ° C., boiling point T3: 153. ° C] and the like.
- DMSO dimethyl sulfoxide
- DMF N-dimethylformamide
- the conductive organic polymer compound of component (C) is at least one selected from polyanilines, polypyrroles or polythiophenes, and derivatives thereof. Yes.
- Polyanilines, polypyrroles or polythiophenes, and derivatives thereof are conductive polymers having conductivity through ⁇ -electron conjugation.
- 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.
- 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.).
- 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 poly3,4-ethylenedioxythiophene (PEDOT).
- PDOT poly3,4-ethylenedioxythiophene
- Examples of the derivatives of polyanilines, polypyrroles or polythiophenes include these dopant bodies.
- dopants 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
- polymer ions such as polyacrylate ion, polyvinyl sulfonate ion, polystyrene sulfonate ion (PSS), poly (2-acrylamido-2-methylpropane sulfonate) ion, and polystyrene sulfonate ion (PSS) is preferred. More preferred.
- polythiophene derivatives are preferable from the viewpoint of easily adjusting conductivity and dispersibility.
- such derivatives include poly (3,4-ethylene Oxide thiophene) and a dopant are preferably a mixture of polystyrene sulfonate ions (hereinafter sometimes referred to as “PEDOT: PSS”).
- PEDOT polystyrene sulfonate ions
- the conductive adhesive composition of the present invention is a composition containing (A) a water-soluble polyvinyl polymer, (B) an organic additive, and (C) a conductive organic polymer compound.
- the active ingredient standard] is 1 to 60 parts by mass, preferably 10 to 50 parts by mass, more preferably 100 parts by mass when the total amount of components (A), (B) and (C) is 100 parts by mass. Is 15 to 40 parts by mass.
- Component (B) is 0.1 to 90 parts by weight, preferably 10 to 70 parts by weight, more preferably 20 to 65 parts by weight.
- Component (C) is 0.1 to 90 parts by weight, preferably 0.5 to 75 parts by weight, more preferably 5 to 55 parts by weight.
- the adhesiveness is not developed, and when it exceeds 60 parts by mass, the conductivity is lowered, which is not preferable.
- the component (B) is less than 0.1 parts by mass, the conductivity is low, and when it exceeds 90 parts by mass, the adhesiveness is lowered, which is not preferable.
- the component (C) is less than 0.1 parts by mass, the conductivity is low, and when it exceeds 90 parts by mass, the adhesiveness is not exhibited, which is not preferable.
- the conductive adhesive composition may be a solution containing components (A), (B), and (C) and a solvent such as water, toluene, ethyl acetate, and methyl ethyl ketone. .
- a solvent such as water, toluene, ethyl acetate, and methyl ethyl ketone.
- the active ingredient concentration is preferably 0.5 to 80% by mass, more preferably 1 to 70% by mass.
- a tackifier In the conductive adhesive composition of the present invention, a tackifier, a plasticizer, a thickener, a wetting agent, and an antifoaming agent other than the components (A), (B), and (C) as necessary.
- Film forming aids, preservatives, rust inhibitors, freeze-melt stabilizers, pigments, colorants, fillers, metal powders, antioxidants, light stabilizers, ultraviolet absorbers, and the like can be added as appropriate.
- the electronic device of the present invention is characterized by having a conductive layer made of a conductive adhesive composition.
- the thickness of the conductive layer made of the conductive adhesive composition is preferably 5 to 10,000 nm, more preferably 30 to 3,000 nm. If it is less than 5 nm, the adhesiveness is not expressed, and if it exceeds 10,000 nm, the conductivity is lowered.
- the conductive layer has high conductivity applicable to an electronic device.
- the surface resistivity of such conductive layer, 10 10 ⁇ / ⁇ is preferably 1 ⁇ 1.0 ⁇ , 1 ⁇ 1.0 ⁇ 10 9 ⁇ / ⁇ , more preferably, 1 ⁇ 1.0 ⁇ 10 8 and more preferable.
- the conductivity will be low, and the performance as an electronic device will deteriorate.
- the surface resistivity of the conductive layer is in the above range, it is suitable as various electronic devices.
- the conductive layer made of the conductive adhesive composition has high transparency, and the total light transmittance is 70% or more. If the total light transmittance is within this range, the transparency is sufficient especially for various electronic devices such as organic electroluminescence (hereinafter referred to as organic EL) elements, solar cells, etc., and it is suitably used.
- electronic devices include organic devices such as organic transistors and organic memories in addition to organic EL and solar cells; liquid crystal displays; electronic paper; thin film transistors; electrochromic; electrochemiluminescent devices; touch panels; Conversion device; Various electronic devices such as an electricity storage device and an organic photoelectric conversion element are exemplified.
- the electronic device of the present invention is characterized in that an anode layer, the conductive layer, a photoelectric conversion layer or a light emitting layer, and a cathode layer are arranged in this order. And various electronic devices such as photodiodes and organic EL.
- FIG. 1A 1 is an anode layer
- 4 is a conductive layer
- 3 is a photoelectric conversion layer or a light emitting layer
- 2 is a cathode layer.
- a photoelectric conversion layer is a layer which receives the photoelectric effect which makes the center of an organic photoelectric conversion element, may consist of a single layer, and may consist of multiple layers.
- the photoelectric conversion layer is usually formed from an intrinsic semiconductor layer (i-type semiconductor).
- the photoelectric conversion layer is a stack of (p-type semiconductor layer / n-type semiconductor layer) or (p-type semiconductor layer / intrinsic semiconductor layer / n-type semiconductor layer).
- the photoelectric conversion layer is a layer that performs photoelectric conversion, and is preferably an organic semiconductor from the viewpoint of cost reduction, flexibility, ease of formation, high extinction coefficient, weight reduction, impact resistance, and the like of the raw material. .
- the intrinsic semiconductor layer is formed from an organic layer having a pn junction interface made of an electron donating material (p-type semiconductor material described later) and an electron accepting material (n-type semiconductor material described later).
- FIG. 1A shows an intrinsic semiconductor layer made of a single layer.
- the thickness of the photoelectric conversion layer varies depending on whether it is a single layer or a plurality of layers, but it is generally preferably 30 nm to 2 ⁇ m, particularly 40 nm to 300 nm from the viewpoint of conductivity and exciton diffusion distance. Is preferred.
- Intrinsic Semiconductor As an intrinsic semiconductor material, for example, a fullerene, a fullerene derivative, a first material composed of at least one of carbon nanotubes (CNT) and CNT compounds having semiconductivity, and a derivative of polyphenylene vinylene (PPV) Alternatively, it is possible to use a mixture in which a second material made of a polythiophene polymer material is mixed so that the obtained semiconductor becomes an intrinsic semiconductor.
- fullerene derivative for example, [6,6] -phenyl-C61-methyl butyrate (PCBM) and the like can be used, and fullerene into which a dimer of fullerene or an alkali metal or an alkaline earth metal is introduced. Compounds and the like can also be used. Further, as the CNT, carbon nanotubes or the like including fullerene or metal-encapsulated fullerene can be used. Furthermore, 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.
- polyalkylthiophene such as poly-3-hexylthiophene (P3HT) and derivatives thereof; polyphenylene and derivatives thereof, poly [2-methoxy-5- (2 ′ -Ethyl-hexyloxy) -p-phenylene-vinylene] (MEH-PPV) and the like, polyphenylene vinylene and derivatives thereof, polysilane and derivatives thereof, porphyrin derivatives, phthalocyanine derivatives, polyalkylthiophenes and derivatives thereof, organometallic polymers, etc. .
- polyalkylthiophene and derivatives thereof are preferred.
- the mixture of these organic materials may be sufficient.
- the conductive polymer poly (3,4) -ethylenedioxythiophene / polystyrene sulfonate (PEDOT: PSS) can be preferably used.
- n-type semiconductor The material of the n-type semiconductor is not particularly limited, and 1,4,5,8-naphthalene tetracarboxylic dianhydride (NTCDA), 3,4,9,10-perylene tetracarboxylic dian Hydride (PTCDA), 3,4,9,10-perylenetetracarboxylic bisbenzimidazole (PTCBI), N, N′-dioctyl-3,4,9,10-naphthyltetracarboxydiimide (PTCDI-C8H), 2 -(4-Biphenylyl) -5- (4-t-butylphenyl) -1,3,4-oxadiazole (PBD), 2,5-di (1-naphthyl) -1,3,4-oxadi Oxazole derivatives such as azole (BND), trizole such as 3- (4-biphenylyl) -4-phenyl-5- (4-t-
- fullerene compounds are particularly preferable because they are n-type semiconductors that are stable and have high carrier mobility.
- the fullerene compound for example, [6,6] -phenyl-C61-methyl butyrate (PCBM) can be used.
- PCBM is preferable from the viewpoint of having excellent electron acceptability.
- n-type semiconductors can be used alone or in combination of two or more.
- the light-emitting layer is not particularly limited as long as it is a light-emitting organic compound that generates excitons by recombination of electrons and holes and emits light when the excitons release energy and return to the ground state. It is usually formed from an organic substance that emits fluorescence, an organic substance that emits phosphorescence, or an organic substance and a dopant that assists the organic substance.
- an electron transporting compound and / or a hole transporting compound may be mixed in the light emitting layer.
- Examples of the material used for the light emitting layer include light emitting materials such as metal complex materials, polymer materials, dye materials, dopant materials, and the like.
- Examples of metal complex materials include aluminum complexes, beryllium complexes, zinc complexes, aluminoquinolinol complexes, europium complexes, iridium complexes, benzoquinolinol beryllium complexes, benzoxazolyl zinc complexes, benzothiazole zinc complexes, azomethyl zinc complexes, porphyrins.
- organometallic complex compounds such as zinc complexes and rare earth metal complexes.
- polymer material examples include polyparaphenylene vinylene derivatives, polythiophene derivatives, polyparaphenylene derivatives, polysilane derivatives, polyacetylene derivatives, polyfluorene derivatives, and polyvinylcarbazole derivatives.
- dye-based materials include cyclopentamine derivatives, tetraphenylbutadiene derivative compounds, triphenylamine derivatives, oxadiazole derivatives, pyrazoloquinoline derivatives, distyrylbenzene derivatives, distyrylarylene derivatives, pyrrole derivatives, thiophene ring compounds.
- Pyridine ring compounds perinone derivatives, perylene derivatives, oligothiophene derivatives, oxadiazole dimers, pyrazoline dimers, quinacridone derivatives, coumarin derivatives, and the like.
- the dopant material include perylene derivatives, coumarin derivatives, rubrene derivatives, quinacridone derivatives, squalium derivatives, porphyrin derivatives, styryl dyes, tetracene derivatives, pyrazolone derivatives, decacyclene, phenoxazone, and the like.
- the method for forming the light emitting layer various coating methods such as vacuum deposition, ionization deposition, spin coating (spin casting method), spray coating, gravure coating, bar coating, doctor blade, etc. It can be selected and used.
- the light emitting layer is preferably formed by a coating method.
- the thickness of the light emitting layer is 1 to 100 ⁇ m, preferably 2 to 1,000 nm, more preferably 5 nm to 500 nm, and still more preferably 20 nm to 200 nm.
- a material having a small energy barrier and a relatively large work function with respect to the HOMO level of the p-type organic semiconductor is preferable.
- a material capable of forming a transparent anode layer is preferable, and examples of such a material include metal oxide.
- the 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-oxide.
- the thickness of the anode layer is preferably 10 to 500 nm, and particularly preferably 30 to 300 nm, from the viewpoint of the balance between transparency and conductivity.
- the method for forming the anode layer is not particularly limited, and for example, methods such as vacuum deposition and various sputtering methods can be applied.
- the material of the cathode layer is not particularly limited as long as it functions as an electrode, but a material having a small energy barrier and a relatively small work function with respect to the LUMO level of the n-type semiconductor is preferable.
- a material having a small energy barrier and a relatively small work function with respect to the LUMO level of the n-type semiconductor is preferable.
- metals such as platinum, gold, silver, copper, 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 mentioned.
- the thickness of the cathode layer is preferably 20 nm to 1 ⁇ m, particularly preferably 30 to 200 nm.
- the method for forming the cathode layer is not particularly limited, and for example, methods such as vacuum deposition and various sputtering methods can be applied.
- both the anode layer and the cathode layer are preferably provided on a substrate.
- Base material generally, inorganic materials, such as glass (plate), or a plastic film is 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 and the like are preferable.
- the thickness of the substrate is generally 3 ⁇ m to 5 mm, preferably 10 ⁇ m to 1 mm, particularly preferably 20 ⁇ m to 300 ⁇ m from the viewpoint of mechanical strength and durability.
- the method for producing an electronic device of the present invention comprises a step of forming an anode laminate by forming a conductive layer made of the above-mentioned conductive adhesive composition on an anode layer, Forming a cathode laminate by forming the photoelectric conversion layer or the light emitting layer on the surface, and the surface of the photoelectric conversion layer or the light emitting layer of the cathode laminate and the anode at a temperature equal to or higher than the temperature at which the conductive adhesive composition is softened. It is characterized in that the conductive layer surfaces of the laminate are bonded together.
- FIG.1 (b) the manufacturing method of the electronic device of this invention is demonstrated in order with FIG.1 (b).
- a structure in which the anode layer 1 and the conductive layer 4 are integrated is referred to as an anode laminate (described later).
- a combination of 2 cathode layers and 3 photoelectric conversion layers or light emitting layers is referred to as a cathode laminate (described later).
- the downward arrow indicates that the anode laminate and the cathode laminate are heated and bonded together 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 is provided on the base material.
- PVD physical vapor deposition
- CVD chemical vapor deposition
- thermal CVD thermal CVD
- atomic layer deposition ALD
- dry processes wet coating processes such as dip coating, spin coating, spray coating, bar coating, gravure coating, die coating, doctor blade, and electrochemical deposition, depending on the anode layer material. Selected.
- a forming method for forming a conductive layer on the anode layer is a method of applying a conductive layer forming solution obtained by dissolving or dispersing the conductive adhesive composition in an appropriate solvent such as purified water on the anode layer,
- the obtained coating film can be dried and, if desired, formed by heating to such an extent that the organic additive in the conductive adhesive composition does not volatilize.
- the forming method include 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, and are appropriately selected.
- the cathode laminate is formed by forming the photoelectric conversion layer or the light emitting layer 3 on the cathode layer 2.
- the cathode layer 2 is provided on a base material.
- PVD physical vapor deposition
- CVD chemical vapor deposition
- thermal CVD thermal CVD
- atomic layer deposition ALD
- the formation method for forming the photoelectric conversion layer or the light emitting layer on the cathode layer is PVD (physical vapor deposition) such as vacuum deposition, sputtering, or ion plating, or CVD (chemical chemical vapor deposition) such as thermal CVD or atomic layer deposition (ALD).
- PVD physical vapor deposition
- CVD chemical chemical vapor deposition
- thermal CVD thermal CVD
- atomic layer deposition ALD
- dry processes such as vapor deposition, or wet processes such as various coatings such as dip coating, spin coating, spray coating, gravure coating, bar coating, doctor blade, and electrochemical deposition, and photoelectric conversion layers or It is suitably selected according to the material of the light emitting layer.
- the temperature at which the conductive adhesive composition is softened is a temperature equal to or higher than the glass transition temperature (Tg) of the component (A). From the viewpoint of easy manufacturing, the processing temperature at the time of bonding is specifically about 100 ° C.
- the surface of the conductive layer composed of the conductive adhesive composition of the present invention and the surface of the photoelectric conversion layer or the light emitting layer are bonded together, so that the electronic device can be easily produced by a laminating process. .
- the metal layer becomes non-uniform, or photoelectric conversion is performed depending on the energy at the time of forming the metal layer. Since the layer or the light emitting layer is not damaged, the performance of the electronic device is not deteriorated.
- ⁇ Example 1> [Preparation of conductive adhesive composition]
- organic additive of component (B) 50 parts by mass of glycerin [manufactured by Sigma Aldrich, product name “glycerin”, melting point (T2): 18 ° C., boiling point (T3): 290 ° C.] was used.
- polythiophene that is a conductive polymer of component (C)
- the said component (A), (B) and (C) was dissolved in 200 mass parts of purified water, and the coating liquid (active ingredient: 1.9 mass%) of the conductive adhesive composition was prepared.
- ITO glass sputtered so that the thickness of the tin-doped indium oxide (ITO) layer was 150 nm (manufactured by Technoprint, product name “ITO glass”) was used as the anode layer.
- the conductive adhesive composition obtained above is applied onto the anode layer by spin coating, dried at 100 ° C. for 30 minutes, and a conductive adhesive composition having a thickness of 100 nm. A conductive layer made of was formed.
- Example 2 and 3 An electronic device was obtained in the same manner as in Example 1 except that the composition shown in Table 1 was changed.
- Example 4 Example except that the organic additive of component (B) was changed to N-methylpyrrolidone [Wako Pure Chemical Industries, Ltd., T2: melting point ⁇ 24 ° C., T3: boiling point 202 ° C.] and changed to the composition shown in Table 1 below. 1 was used to obtain an electronic device.
- N-methylpyrrolidone Wako Pure Chemical Industries, Ltd., T2: melting point ⁇ 24 ° C., T3: boiling point 202 ° C.
- Example 5 In the same manner as in Example 1 except that the component (A) PVA is changed to polyvinyl pyrrolidone (Sigma Aldrich, Tg (T1): 80 ° C., described as PVP in Table 1) and changed to the composition shown in Table 1 below. To get an electronic device.
- polyvinyl pyrrolidone Sigma Aldrich, Tg (T1): 80 ° C., described as PVP in Table 1
- Example 6 Component (A) PVA was changed to polyvinylpyrrolidone [Sigma Aldrich, Tg (T1): 80 ° C.], and the organic additive of component (B) was N-methylpyrrolidone (T2: melting point ⁇ 24 ° C., T3: boiling point).
- the electronic device was obtained in the same manner as in Example 1, except that the composition was changed to the composition shown in Table 1 below.
- Example 7 The organic additive of component (B) was changed to dimethyl sulfoxide (manufactured by Wako Pure Chemical Industries, Ltd., the description in Table 1 is DMSO, T2: melting point 19 ° C., T3: boiling point 189 ° C.), An electronic device was obtained in the same manner as in Example 1 except that the composition was changed.
- dimethyl sulfoxide manufactured by Wako Pure Chemical Industries, Ltd., the description in Table 1 is DMSO, T2: melting point 19 ° C., T3: boiling point 189 ° C.
- Example 8 The organic additive of component (B) was changed to dimethylformamide (manufactured by Wako Pure Chemical Industries, Ltd., the description in Table 1 is DMF, T2: melting point ⁇ 61 ° C., T3: boiling point 153 ° C.), and An electronic device was obtained in the same manner as in Example 1 except that the composition was changed.
- dimethylformamide manufactured by Wako Pure Chemical Industries, Ltd., the description in Table 1 is DMF, T2: melting point ⁇ 61 ° C., T3: boiling point 153 ° C.
- Example 9 In place of polyaniline (manufactured by Sigma Aldrich Co., Ltd., 1% by mass of active ingredient, described as polyaniline 1 in Table 1) as the polyaniline which is the conductive organic polymer compound of component (C), An electronic device was obtained in the same manner as in Example 1 except for changing.
- polyaniline manufactured by Sigma Aldrich Co., Ltd., 1% by mass of active ingredient, described as polyaniline 1 in Table 1
- An electronic device was obtained in the same manner as in Example 1 except for changing.
- Example 10 The same procedure as in Example 1 was conducted except that polypyrrole, which is a conductive organic polymer compound of component (C), was changed to polypyrrole (manufactured by Sigma-Aldrich, 1 mass% active ingredient, described as polypyrroles in Table 1). Got a device.
- ⁇ Example 11> [Preparation of conductive adhesive composition]
- a water-soluble polyvinyl polymer of component (A) an acrylic acid polymer [manufactured by Sigma-Aldrich, product name “polyacrylic acid”, weight average molecular weight 100,000, active ingredient: 40 mass%, Tg (T1): 102 ° C. In Table 2, it is described as PAA], and 45 parts by mass was used as an active ingredient.
- polythiophene that is a conductive polymer of component (C)
- a mixture of poly (3,4-ethylene oxide thiophene) (PEDOT) and polystyrene sulfonic acid (PSS) (PEDOT: PSS) [manufactured by HC Starck, 1500 parts by mass (15 parts by mass as the active ingredient) of the product name “CleviousP VP.AI4083”, 1% by mass of the active ingredient and described as polythiophenes in Table 2 were used.
- the said component (A), (B) and (C) was dissolved in 200 mass parts of purified water, and the coating liquid (active ingredient: 7.8 mass%) of the conductive adhesive composition was prepared.
- An anode laminate was produced in the same manner as in Example 1 except that the formulation shown in Table 2 was changed and the thickness of the conductive layer was changed to 1,000 nm.
- cathode laminate As a base material, a polyethylene terephthalate film (manufactured by Toyobo Co., Ltd., product name “Cosmo Shine A4100”) is manufactured to have a thickness of 100 nm by vapor deposition of silver under a reduced pressure of 1 ⁇ 10 ⁇ 3 Pa or less. A cathode layer was formed by depositing and then depositing magnesium to a thickness of 10 nm.
- Example 12 and 13 An electronic device (solar cell and organic EL element) was obtained in the same manner as in Example 11 except that the formulation shown in Table 2 was changed.
- Example 14 to 15, 17> An electronic device (solar cell and organic EL element) was obtained in the same manner as in Example 11 except that the formulation shown in Table 2 was changed.
- Example 16> The composition of the following Table 1 is used instead of polyaniline (product name “D1033W” manufactured by Nissan Chemical Industries, Ltd., described as Polyaniline 2 in Table 2) as the polyaniline which is the conductive organic polymer compound of the component (C).
- An electronic device was obtained in the same manner as in Example 1 except that
- the characteristics described in Table 1 and Table 2 were measured as follows.
- Thickness of Conductive Layer The thickness of the conductive layer made of the conductive adhesive composition was measured with a stylus type surface shape measuring device [manufactured by Veeco, product name “Dektak 150”].
- Second Surface resistance value The surface resistance value of the conductive layer of the obtained anode laminate was measured by a four-terminal method using a surface resistance measuring device (product name “Loresta GP MCP-T600” manufactured by Mitsubishi Chemical Corporation). Was measured.
- Adhesive strength The adhesive strength shown in Table 2 was obtained by applying a coating solution of the conductive adhesive composition obtained in Examples 11 to 17 and Comparative Examples 8 to 10 to a polyethylene terephthalate film [manufactured by Toyobo Co., Ltd. , Product name “Cosmo Shine A4100”, thickness 100 ⁇ m], and dried at 100 ° C. for 10 minutes to form a conductive layer made of a conductive adhesive composition having a thickness of 1,000 nm. Produced.
- the measurement sample obtained was cut into 25 mm ⁇ 300 mm under a 23 ° C., 50% RH (relative humidity) environment in accordance with JIS Z0237 (2009) using a laminator [manufactured by Royal Sovereign, A product name “RSL-328J”] was attached to an adherend (glass plate, 800 mm ⁇ 1500 mm, thickness 3 mm) at a temperature of 100 ° C.
- the adhesive strength at 24 hours after pasting was measured by a 180 ° peeling method at a pulling speed of 300 mm / min.
- Glass transition temperature T1 of the water-soluble vinyl polymer of the component (A) is in accordance with JIS K 7121. Was used to measure the external glass transition start temperature in the temperature range of ⁇ 80 ° C. to 250 ° C.
- Table 1 confirms the following.
- the surface resistance was high and obtained.
- the electronic device was not rectifying and did not function as a device.
- the conductive adhesive compositions of Comparative Examples 5 and 6 consisting only of the component (B)
- the film formability was poor and the conductive layer could not be formed.
- the electroconductive layer which consists of an electroconductive adhesive composition of the comparative example 7 which consists only of (C) component has no adhesiveness, and an electronic device was not able to be produced by bonding.
- the conductive layers comprising the conductive adhesive compositions of Examples 1 to 10 comprising the components (A), (B) and (C) had low surface resistance values and high transparency. Moreover, since the adhesiveness was also good, it was found that the electronic device could be manufactured well by bonding, and the obtained electronic device was also rectifying, so that it was effective as a device.
- the surface resistance is high, and the obtained electronic device (solar cell) does not show rectification and does not function as a device. It was. Moreover, although it tried to measure the EL characteristic (luminance) of the obtained electronic device (organic EL element), it did not emit light. In the conductive layer made of the conductive adhesive composition of Comparative Examples 8 and 9 consisting only of the component (A) and the component (C), the surface resistance is high, and the obtained electronic device (solar cell) has a rectifying property. Did not function as a device. Moreover, although the EL characteristic (luminance) was measured, the luminance was low.
- the film formability was poor and the conductive layer could not be formed.
- the conductive layer made of the conductive adhesive composition of Comparative Example 15 consisting only of the component (C) had no adhesive property of the conductive layer, and an electronic device could not be produced by bonding.
- the conductive layers made of the conductive adhesive compositions of Examples 11 to 17 consisting of the components (A), (B) and (C) had low surface resistance and high transparency.
- the adhesiveness was also good, it was found that the electronic device could be manufactured well by bonding, and the obtained electronic device was also rectifying, so that it was effective as a device. Their EL characteristics (luminance) were high and good.
- the conductive adhesive composition of the present invention has excellent adhesiveness, low surface resistance, and high transparency, so organic devices such as organic transistors, organic memories, and organic ELs; liquid crystal displays; electronic papers; Thin film transistor; Electrochromic; Electrochemiluminescence device; Touch panel; Display; Solar cell; Thermoelectric conversion device; Piezoelectric conversion device; Power storage device; It is.
- Anode layer 2 Cathode layer 3: Photoelectric conversion layer or light emitting layer 4: Conductive layer
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Abstract
Description
に関する。
例えば、有機薄膜太陽電池に代表される有機光電変換あるいは電光変換デバイスは、通常、透明導電膜よりなる電極に材料を積層して作製される。透明導電膜としては金属薄膜、金属酸化物薄膜、導電性窒化物薄膜等の各種導電膜が検討されているが、現在は主に光透過性と導電性との両立が可能で耐久性にも優れるため金属酸化物薄膜が主流である。中でも特に錫をドープした酸化インジウム(ITO)は、光透過性と導電性とのバランスが良く、酸溶液を用いたウェットエッチングによる電極微細パターン形成が容易であることから、広く使用されている(特許文献1)。
一方、PET等の透明基材に金属製の微細なメッシュあるいはグリッドを形成したシートがある(特許文献2)。これらのシートは透光性および導電性がメッシュの設計(ピッチ、線幅で決まる開口率)次第で制御できるので、透明電極としての利用可能性がある。
ところで、従来から電子デバイスは、有機素子材料からなる層を積層する場合には、真空蒸着法およびそれに類するドライプロセスあるいは塗布に代表されるウェットプロセスや、粘接着層を介したラミネートプロセスにより製造されてきた(特許文献3)。このようなラミネートプロセスにおいては、粘着性を有する透明電極膜および透明導電フィルムが望まれているが、従来の透明導電性フィルムでは、透明性、粘着性及び低抵抗率のバランスが課題となっている。
そこで、導電性接着剤組成物中の導電性成分として、ポリチオフェンやその誘導体のような導電性有機高分子化合物を使用することが提案されており、より具体的には、導電性有機高分子化合物を含む粘接着層を介したラミネートプロセス(特許文献4等参照)により電子デバイスを製造することが提案されている。
しかしながら、導電性有機高分子化合物を含む粘接着層を介したラミネートプロセスは、界面の清浄性、均一性が重要な素子用途では利用が限られていた。また、粘接着層の導電性が低く、ラミネート界面でのキャリア注入効率が低下したり、界面の接着力が低かったりする等、電子デバイスの性能が低下するという問題があった。
すなわち、本発明は、下記
(1)(A)水溶性ポリビニル重合体、(B)有機添加剤及び(C)導電性有機高分子化合物を含む導電性接着剤組成物であって、
(B)有機添加剤は水溶性多価アルコール、水溶性ピロリドン類または親水性の非プロトン性溶媒から選ばれる少なくとも一種であり、(C)導電性有機高分子化合物は、ポリアニリン類、ポリピロール類またはポリチオフェン類及びその誘導体から選ばれる少なくとも1種であることを特徴とする導電性接着剤組成物、
(2)水溶性ポリビニル重合体のガラス転移温度をT1、(B)有機添加剤の融点をT2、有機添加剤の0.101MPa(760mmHg)における沸点をT3としたときに、T2<T1<T3を満たす上記(1)に記載の導電性接着剤組成物、
(3)水溶性ポリビニル重合体が、ポリビニルアルコール、ポリビニルピロリドン及びポリアクリル酸から選ばれる少なくとも1種である上記(1)に記載の導電性接着剤組成物、
(4)上記(1)に記載の導電性接着剤組成物からなる導電層を有することを特徴とする電子デバイス、
(5)陽極層と、前記(1)に記載の導電性接着剤組成物からなる導電層と、光電変換層と、陰極層をこの順に配置してなる上記(4)に記載の電子デバイス、
(6)陽極層と、前記(1)に記載の導電性接着剤組成物からなる導電層と、発光層と、陰極層をこの順に配置してなる上記(4)に記載の電子デバイス、
(7)基材上に陽極層、前記(1)に記載の導電性接着剤組成物からなる導電層がこの順に積層されてなることを特徴とする陽極積層体、
および
(8)上記(4)に記載の電子デバイスの製造方法であって、
陽極層上に前記(1)に記載の導電性接着剤組成物からなる導電層を形成して陽極積層体を形成させる工程と、陰極層上に前記光電変換層又は発光層を形成して陰極積層体を形成させる工程と、前記導電性接着剤組成物が軟化する温度以上で、前記陰極積層体の光電変換層又は発光層表面と前記陽極積層体の導電層表面を貼り合わせることを特徴とする電子デバイスの製造方法を提供する。
また、本発明の導電性接着剤組成物からなる導電層は、それ自体が優れた接着性を有しているため、ラミネートプロセスによる電子デバイスの製造が可能である。
〔1〕導電性接着剤組成物
まず、導電性接着剤組成物中の各成分について説明する。
水溶性ポリビニル重合体
成分(A)の水溶性ポリビニル重合体は、導電層の導電性を低下させずに導電性接着剤組成物からなる導電層に十分な接着性を付与するためのものである。水溶性ポリビニル重合体は温水可溶性ポリビニル重合体も含む。
水溶性ポリビニル重合体のガラス転移温度(Tg)は、成膜性、接着性、取り扱いの点から、-50~150℃の範囲が好ましく、20~140℃であることが好ましく、より好ましくは30~130℃、さらに好ましくは、40~120℃である。
水溶性ポリビニル重合体は、重合体中に-CH2-CH(R)-の構造単位を有するものである。この構造単位を重合体中に少なくとも30モル%以上有していれば、特に限定されない。水溶性ポリビニル重合体は、この構造単位を含む単独重合体であってもよく、共重合体であってもよい。これらのなかでもRが水酸基、カルボキシル基、ピロリドン基、アクリルアミド基のいずれかであるものが好ましい。
重合体中にカルボキシル基を有するものとは、-CH2-CH(COOH)-の構造単位を有するものである。カルボキシル基を有する水溶性ポリビニル重合体の具体例としては、例えば、ポリアクリル酸(PAA)等が挙げられる。
重合体中に水酸基を有するものは、-CH2-CH(OH)-の構造単位を有するものである。
水酸基を有する水溶性ポリビニル重合体の具体例としては、例えば、ポリビニルアルコール(PVA)、ポリビニルアルコール-エチレン共重合体、ポリビニルアルコール-(N-ビニルホルムアミド)共重合体、ポリビニルアルコール-酢酸ビニル共重合体等が挙げられる。
水酸基を有する水溶性ポリビニル重合体は、部分的にケン化されてなるものでもよく、完全にケン化されたものであってもよい。
ケン化度は、20~100モル%が好ましく、より好ましくは35~100モル%、さらに好ましくは40~100モル%である。ケン化度が20モル%未満の場合には、溶解性が低下する。
ピロリドン基を有する水溶性ポリビニル重合体は、-CH2-CH(NC4O)-の構造単位を有するものであり、具体例としては、例えば、ポリビニルピロリドン(PVP)、N-ビニル-2-ピロリドン-エチレン共重合体、N-ビニル-2-ピロリドン-酢酸ビニル共重合体等が挙げられる。
アクリルアミド基を有する水溶性ポリビニル重合体は、-CH2-CH(CONH2)-の構造単位を有するものであり、具体例としては、例えば、ポリアクリルアミド等が挙げられる。
水溶性ポリビニル重合体は、種々の機能を付与することを目的として疎水基やカチオン性基、スルホン酸基を含むアニオン性基、チオール基、カルボニル基、シラノール基などの官能基を上記構造単位以外に含有しても良い。
これら水溶性ポリビニル重合体の中でも、後述する電子デバイスの製造が容易に出来るという点から、Rが水酸基、カルボキシル基、ピロリドン基のいずれかであるものが好ましく、PVAまたはPVP、PAAが好ましい。これらの中でも、得られる導電層の導電性と接着性の点から、Rがカルボキシル基であるPAAであることがさらに好ましい。
水溶性ポリビニル重合体の重量平均分子量(Mw)は、通常500~50万であり、500~30万であることが好ましく、1,000~20万であることがより好ましく、3,000~15万であることがさらに好ましい。
水溶性ポリビニル重合体のMwがこの範囲であれば、本発明の電子デバイスや陽極積層体において十分な成膜性及び接着性が発現する。
なお、前記Mwはゲルパーミエイションクロマトグラフィー(GPC)で測定された標準ポリスチレン換算の数値である。
共重合可能なその他のエチレン性不飽和単量体としては、例えば、
蟻酸ビニル、酢酸ビニル、プロピオン酸ビニル、酢酸イソプロペニル、バレリン酸ビニル、カプリン酸ビニル、カプリン酸ビニル、ラウリン酸ビニル、ステアリン酸ビニル、安息香酸ビニル、バーサティック酸ビニル、ピバリン酸ビニル等のカルボン酸ビニルエステル単量体;エチレン、プロピレン、ブチレン等のオレフィン類;スチレン、α-メチルスチレン等の芳香族ビニル類;メタクリル酸、フマル酸、マレイン酸、イタコン酸、フマル酸モノエチル、無水マレイン酸、無水イタコン酸等のエチレン性不飽和カルボン酸単量体;(メタ)アクリル酸メチル、(メタ)アクリル酸エチル、(メタ)アクリル酸n-ブチル、(メタ)アクリル酸2-エチルヘキシル、フマル酸ジメチル、マレイン酸ジメチル、マレイン酸ジエチル、イタコン酸ジイソプロピル等のエチレン性不飽和カルボン酸アルキルエステル単量体;メチルビニルエーテル、n-プロピルビニルエーテル、イソブチルビニルエーテル、ドデシルビニルエーテル等のビニルエーテル単量体;(メタ)アクリロニトリル等のエチレン性不飽和ニトリル単量体;塩化ビニル、塩化ビニリデン、フッ化ビニル、フッ化ビニリデン等のハロゲン化ビニル単量体またはビニリデン単量体;酢酸アリル、塩化アリル等のアリル化合物;エチレンスルホン酸、(メタ)アリルスルホン酸、2-アクリルアミド-2-メチルプロパンスルホン酸等のスルホン酸基含有単量体;3-(メタ)アクリルアミドプロピルトリメチルアンモニウムクロライド等の第四級アンモニウム基含有単量体;ビニルトリメトキシシラン、N-ビニルホルムアミド、メタアクリルアミド等が挙げられ、これらの1種または2種以上を使用することができる。
本発明において、成分(B)の有機添加剤は水溶性多価アルコール、水溶性ピロリドン類および親水性の非プロトン性溶媒から選ばれる少なくとも一種であることを特徴としている。
有機添加剤は、導電性の向上を目的として添加される。詳細は不明であるが、このような有機添加剤を添加することで、後述する成分(C)の導電性有機高分子化合物の配向性が向上するため、導電性が向上する。
成分(B)の有機添加剤としては、1.101MPa(760mmHg)における沸点が100℃以上のものが好ましい。沸点が100℃を下回ると導電性接着剤組成物の混合過程、保存中や後述する電子デバイスを製造する際の種々の加熱過程において有機添加剤が揮発・飛散してその配合比率が低下するため導電性を向上させる効果が低下するので好ましくない。
より好ましい沸点は120~300℃、さらに好ましくは140~300℃の範囲である。
成分(B)の有機添加剤の一つである水溶性ピロリドン類としては、N-メチルピロリドン、N-エチルピロリドン、N-プロピルピロリドン、N-イソプロピルピロリドン、N-ブチルピロリドン、N-t-ブチルピロリドン、N-ペンチルピロリドン、N-ヘキシルピロリドン、N-ヘプチルピロリドン、N-シクロヘキシルピロリドン、N-オクチルピロリドン、N-(2-エチルヘキシル)ピロリドン、N-フェニルピロリドン、N-ベンジルピロリドン、フェネチルピロリドン、2-メトキシエチルピロリドン、2-メトキシプロピルピロリドン、2-ヒドロキシプロピルピロリドン、ビニルピロリドン、2-ピロリドン等が挙げられ、これらの1種または2種以上を用いてもよい。
本発明において、成分(B)有機添加剤の一つとして、非プロトン性溶媒が添加されている。本発明においては、非プロトン性溶媒は、導電性接着剤組成物中で、揮発・飛散せずに配合されているものである。このような成分(B)の有機添加剤の一つである親水性の非プロトン性溶媒としては、ジメチルスルホキシドおよびN,N-ジメチルホルムアミドが挙げられる。
すなわち、成分(A)の水溶性ポリビニル重合体のガラス転移温度(Tg)をT1、成分(B)の有機添加剤の融点をT2、有機添加剤の0.101MPa(760mmHg)における沸点をT3としたときに、T2<T1<T3を満たす組み合わせである。
ここで、成分(A)の水溶性ビニル重合体のガラス転移温度T1は、〔示差走査熱量測定(DSC)測定器〕で測定された値である。
成分(A)との間で上記のような関係を満たすような成分(B)の水溶性多価アルコールの具体例としては、例えば、グリセリン〔融点T2:18℃、沸点T3:290℃〕、エチレングリコール〔融点T2:-11.5℃、沸点T3:197℃〕、ジエチレングリコール〔融点T2:-6.5℃、沸点T3:245℃〕、プロピレングリコール〔融点T2:-59℃、沸点T3:188.2℃〕、ジプロピレングリコール〔融点T2:-40℃、沸点T3:232℃〕、1,3-ブタンジオール〔融点T2:-50℃、沸点T3:207.5℃〕、1,4-ブタンジオール〔融点T2:19℃、沸点T3:235℃〕等が挙げられる。中でも、導電性、粘着性の向上という観点からグリセリン、1,4-ブタンジオールが好ましい。
このような成分(B)の水溶性ピロリドン誘導体としては、N-メチルピロリドン〔融点T2:-24℃、沸点T3:202℃〕、ビニルピロリドン〔融点T2:13.5℃、沸点T3:214.5℃〕、2-ピロリドン〔融点T2:24.6℃、沸点T3:245℃〕等が挙げられる。
親水性の非プロトン性溶媒としては、ジメチルスルホキシド(DMSO)〔融点T2:19℃、沸点T3:189℃〕、N,N-ジメチルホルムアミド(DMF)〔融点T2:-61℃、沸点T3:153℃〕等が挙げられる。
本発明において、成分(C)の導電性有機高分子化合物はポリアニリン類、ポリピロール類またはポリチオフェン類、及びそれらの誘導体から選ばれる少なくとも1種であることを特徴としている。
ポリアニリン類、ポリピロール類またはポリチオフェン類、及びそれらの誘導体は、π電子共役により導電性を有する導電性高分子である。
ポリアニリン類は、アニリンの2位または3位あるいはN位を炭素数1~18のアルキル基、アルコキシ基、アリール基、スルホン酸基等で置換した化合物の高分子量体であり、例えば、ポリ2-メチルアニリン、ポリ3-メチルアニリン、ポリ2-エチルアニリン、ポリ3-エチルアニリン、ポリ2-メトキシアニリン、ポリ3-メトキシアニリン、ポリ2-エトキシアニリン、ポリ3-エトキシアニリン、ポリN-メチルアニリン、ポリN-プロピルアニリン、ポリN-フェニル-1-ナフチルアニリン、ポリ8-アニリノ-1-ナフタレンスルホン酸、ポリ2-アミノベンゼンスルホン酸、ポリ7-アニリノ-4-ヒドロキシ-2-ナフタレンスルホン酸等が挙げられる。
ポリピロール類とは、(ピロールの1位または3位、4位を炭素数1~18のアルキル基またはアルコキシ基等で置換した化合物の高分子量体であり、例えば、ポリ1-メチルピロール、ポリ3-メチルピロール、ポリ1-エチルピロール、ポリ3-エチルピロール、ポリ1-メトキシピロール、3-メトキシピロール、ポリ1-エトキシピロール、ポリ3-エトキシピロール等)が挙げられる。
ポリチオフェン類は、チオフェンの3位または4位を炭素数1~18のアルキル基またはアルコキシ基等で置換した化合物の高分子量体であり、例えば、ポリ3-メチルチオフェン、ポリ3-エチルチオフェン、ポリ3-メトキシチオフェン、ポリ3-エトキシチオフェン、ポリ3,4-エチレンジオキシチオフェン(PEDOT)等の高分子体が挙げられる。
これらの中でも、高い導電性を容易に調整でき、かつ、水分散液とした場合に、容易に分散するために有用な親水骨格を有することから、導電性有機高分子化合物に対して、ドーパントとしては、ポリアクリル酸イオン、ポリビニルスルホン酸イオン、ポリスチレンスルホン酸イオン(PSS)、ポリ(2-アクリルアミド-2-メチルプロパンスルホン酸)イオンなどの高分子イオンが好ましく、ポリスチレンスルホン酸イオン(PSS)がより好ましい。
上記の導電性有機高分子化合物の中でも、導電性を容易に調整でき、かつ、分散性の観点から、ポリチオフェン類の誘導体が好ましく、例えば、このような誘導体としては、ポリ(3,4-エチレンオキサイドチオフェン)とドーパントとして、ポリスチレンスルホン酸イオンの混合物(以下、「PEDOT:PSS」と記載することがある)等が好ましい。
成分(A)が1質量部未満の場合は、接着性が発現しなくなり、逆に60質量部を超える場合は、導電性が低くなるので好ましくない。
成分(B)が0.1質量部未満の場合は、導電性が低くなり、逆に90質量部を超える場合は接着性が低下するので好ましくない。
成分(C)が0.1質量部未満の場合は導電性が低くなり、逆に90質量部を超える場合は接着性が発現しなくなるので好ましくない。
本発明の電子デバイスは、導電性接着剤組成物からなる導電層を有することを特徴としている。
前記導電性接着剤組成物からなる導電層の厚さは5~10,000nmが好ましく、より好ましくは30~3,000nmである。5nm未満であると、接着性が発現せず、10,000nmを超えると導電性が低下してしまう。
導電層は電子デバイスに適用可能な高い導電性を有している。このような導電層の表面抵抗率は、1~1.0×1010Ω/□が好ましく、1~1.0×109Ω/□がより好ましく、1~1.0×108がさらに好ましい。1~1.0×1010Ω/□を超えると導電性が低くなり、電子デバイスとしての性能が悪くなる。導電層の表面抵抗率が上記の範囲であれば、種々の電子デバイスとして好適である。
前記導電性接着剤組成物からなる導電層は透明性も高く、全光線透過率は、70%以上である。全光線透過率がこの範囲であれば、特に有機エレクトロルミネッセンス(以下、有機ELと記載する)素子、太陽電池等種々の電子デバイスの導電層として透明性が十分であり、好適に用いられる。
電子デバイスの具体例としては、有機EL、太陽電池以外に有機トランジスタ、有機メモリー等の有機デバイス;液晶ディスプレイ;電子ペーパー;薄膜トランジスタ;エレクトロクロミック;電気化学発光デバイス;タッチパネル;ディスプレイ;熱電変換デバイス;圧電変換デバイス;蓄電デバイス、有機光電変換素子等の種々の電子デバイスが挙げられる。
このような電子デバイスとしては、有機太陽電池、フォトダイオード、有機EL等の種々の電子デバイスが挙げられる。
以下、本発明の電子デバイスを構成する各層を図1(a)により説明する。
図1(a)において、1は陽極層、4は導電層、3は光電変換層または発光層、2は陰極層である。
光電変換層は有機光電変換素子の中心をなす光電効果を受ける層であり、単層からなっていても良いし、複数層からなっていても良い。単層の場合には、光電変換層は、通常、真性半導体層(i型半導体)から形成される。
複数層の場合には、(p型半導体層/n型半導体層)の積層、または、(p型半導体層/真性半導体層/n型半導体層)等である。
光電変換層は、光電変換を行う層であり、原料の低コスト化、柔軟性、形成の容易性、吸光係数の高さ、軽量化、耐衝撃性等の観点から有機半導体であることが好ましい。
真性半導体層とは電子供与性材料(後述するp型半導体材料)及び電子受容性材料(後述するn型半導体材料)よりなるp-n接合界面を有する有機層から形成される。図1(a)は単層からなる真性半導体層を示している。
光電変換層の厚さは、単層または複数層の場合で異なるが導電性、励起子拡散距離という観点から、一般的には、30nm~2μmであることが好ましく、特に40nm~300nmであることが好ましい。
(1)真性半導体
真性半導体の材料としては、例えば、フラーレン、フラーレン誘導体、半導体性を有するカーボンナノチューブ(CNT)およびCNT化合物の少なくとも1種類からなる第1の材料と、ポリフェニレンビニレン(PPV)の誘導体またはポリチオフェン系高分子材料からなる第2の材料とを、得られる半導体が真性半導体となるように混合した混合物を使用することができる。
フラーレン誘導体としては、例えば、[6,6]-フェニル-C61-酪酸メチル(PCBM)等を用いることができ、また、フラーレンの二量体、またはアルカリ金属もしくはアルカリ土類金属等を導入したフラーレン化合物なども用いることができる。また、CNTとしては、フラーレンまたは金属内包フラーレンを内包したカーボンナノチューブ等を用いることができる。さらに、CNTの側壁や先端に、種々の分子を付加したCNT化合物等も用いることができる。
ポリフェニレンビニレンの誘導体としては、ポリ[2-メトキシ,5-(2’-エチル-ヘキシロキシ)-p-フェニレン-ビニレン](MEH-PPV)等を用いることができ、ポリチオフェン系高分子材料としては、ポリ-3-ヘキシルチオフェン(P3HT)などのポリ(3-アルキルチオフェン),ジオクチルフルオレンエン-ビチオフェン共重合体(F8T2)、等を用いることができる。
特に好ましい真性半導体としては、PCBMとP3HTとを質量比で1:0.3~1:4で混合した混合物が挙げられる。
p型半導体の材料としては、例えば、ポリ-3-ヘキシルチオフェン(P3HT)等のポリアルキルチオフェンおよびその誘導体;ポリフェニレンおよびその誘導体、ポリ[2-メトキシ-5-(2′-エチル-ヘキシロキシ)-p-フェニレン-ビニレン](MEH-PPV)等のポリフェニレンビニレンおよびその誘導体、ポリシランおよびその誘導体、ポルフィリン誘導体、フタロシアニン誘導体、ポリアルキルチオフェンおよびその誘導体、有機金属ポリマー等が挙げられる。中でもポリアルキルチオフェンおよびその誘導体が好ましい。また、それら有機材料の混合物であってもよい。導電性高分子としては、ポリ(3,4)-エチレンジオキシチオフェン/ポリスチレンスルフォネート(PEDOT:PSS)を好ましく使用することができる。
n型半導体の材料としては、特に限定されず、1,4,5,8-ナフタレンテトラカルボキシリックジアンハイドライド(NTCDA)、3,4,9,10-ペリレンテトラカルボキシリックジアンハイドライド(PTCDA)、3,4,9,10-ペリレンテトラカルボキシリックビスベンズイミダゾール(PTCBI)、N,N′-ジオクチル-3,4,9,10-ナフチルテトラカルボキシジイミド(PTCDI-C8H)、2-(4-ビフェニリル)-5-(4-t-ブチルフェニル)-1,3,4-オキサジアゾール(PBD)、2,5-ジ(1-ナフチル)-1,3,4-オキサジアゾール(BND)等のオキサアゾール誘導体、3-(4-ビフェニリル)-4-フェニル-5-(4-t-ブチルフェニル)-1,2,4-トリアゾール(TAZ)等のトリゾール誘導体、フェナントロリン誘導体、ホスフィンオキサイド誘導体、フラーレン化合物、カーボンナノチューブ(CNT)、CNTの側壁や先端に種々の分子を付加したCNT化合物、ポリ-p-フェニレンビニレン系重合体にシアノ基を導入した誘導体(CN-PPV)等が挙げられる。
これらの中でも、安定でキャリア移動度の高いn型半導体であることから特にフラーレン化合物が好ましい。
フラーレン化合物としては、例えば、[6,6]-フェニル-C61-酪酸メチル(PCBM)等を用いることができる。また、フラーレンの二量体、またはアルカリ金属もしくはアルカリ土類金属を導入したフラーレン化合物等が挙げられる。これらの中でも優れた電子受容性を有する観点からPCBMが好ましい。
なお、これらのn型半導体は、単独でまたは2種以上組み合わせて用いることができる。
本発明の電子デバイスにおいて、光電変換層の替わりに発光層を積層すると有機EL素子として使用することができる。
発光層は、電子とホールとの再結合により励起子が生成し、その励起子がエネルギーを放出して基底状態に戻る際に発光するような発光性有機化合物であれば、特に限定されることなく用いることができ、通常、蛍光発光する有機物、燐光を発光する有機物、または該有機物とこれを補助するドーパントとから形成される。
また、前記発光層の電荷輸送性を高めるために、前記発光層中に電子輸送性化合物及び/又はホール輸送性化合物を混合して用いてもよい。
発光層として用いられる材料としては、例えば、金属錯体系材料、高分子系材料、色素系材料、ドーパント材料等のような発光性材料が挙げられる。
金属錯体系材料としては、例えば、アルミニウム錯体、ベリリウム錯体、亜鉛錯体、アルミノキノリノール錯体、ユーロピウム錯体、イリジウム錯体、ベンゾキノリノールベリリウム錯体、ベンゾオキサゾリル亜鉛錯体、ベンゾチアゾール亜鉛錯体、アゾメチル亜鉛錯体、ポルフィリン亜鉛錯体若しくは希土類金属錯体等の有機金属錯体化合物が挙げられる。
高分子系材料としては、ポリパラフェニレンビニレン誘導体、ポリチオフェン誘導体、ポリパラフェニレン誘導体、ポリシラン誘導体、ポリアセチレン誘導体、ポリフルオレン誘導体、ポリビニルカルバゾール誘導体等が挙げられる。
色素系材料としては、例えば、シクロペンダミン誘導体、テトラフェニルブタジエン誘導体化合物、トリフェニルアミン誘導体、オキサジアゾール誘導体、ピラゾロキノリン誘導体、ジスチリルベンゼン誘導体、ジスチリルアリーレン誘導体、ピロール誘導体、チオフェン環化合物、ピリジン環化合物、ペリノン誘導体、ペリレン誘導体、オリゴチオフェン誘導体、オキサジアゾールダイマー、ピラゾリンダイマー、キナクリドン誘導体、クマリン誘導体等が挙げられる。
ドーパント材料としては、例えばペリレン誘導体、クマリン誘導体、ルブレン誘導体、キナクリドン誘導体、スクアリウム誘導体、ポルフィリン誘導体、スチリル系色素、テトラセン誘導体、ピラゾロン誘導体、デカシクレン、フェノキサゾン等が挙げられる。
発光層を形成する方法としては、真空蒸着法、イオン化蒸着法、スピンコーティング(スピンキャスト法)、スプレーコーティング、グラビアコーティング、バーコーティング、ドクターブレード等の各種コーティング法により前記発光性材料に応じて適宜選択して用いることができる。発光層は、コーティング法により形成されることが好ましい。
発光層の厚さは、1~100μm、好ましくは2~1,000nmであり、より好ましくは5nm~500nmであり、さらに好ましくは20nm~200nmである。
陽極層の材料としては、p型の有機半導体のHOMOレベルに対してエネルギー障壁が小さく、仕事関数が比較的大きいものが好ましい。
また、透明な陽極層を形成することができる材料が好ましく、このような材料としては、金属酸化物が挙げられる。
金属酸化物としては、例えば、スズドープ酸化インジウム(ITO)、酸化イリジウム(IrO2)、酸化インジウム(In2O3)、酸化スズ(SnO2)、フッ素ドープ酸化スズ(FTO)、酸化インジウム-酸化亜鉛(IZO)、酸化亜鉛(ZnO)、ガリウムドープ酸化亜鉛(GZO)、アルミニウムドープ酸化亜鉛(AZO)、酸化モリブデン(MoO3)、酸化チタン(TiO2)等が上げられる。
陽極層の厚さは透明性と導電性のバランスの観点から10~500nmであることが好ましく、30~300nmであることが特に好ましい。
陽極層の形成方法としては、特に制限はされず、例えば、真空蒸着、各種スパッタリング等の方法を適用できる。
陰極層の材料としては、電極として機能するものであれば特に制限されないが、n型半導体のLUMOレベルに対してエネルギー障壁が小さく、仕事関数が比較的小さいものが好ましい。例えば、白金、金、銀、銅、アルミニウム、イリジウム、クロム、酸化亜鉛等の金属、金属酸化物もしくは合金の他、カーボンナノチューブ、またはカーボンナノチューブと上記金属、金属酸化物もしくは合金との複合体が挙げられる。
陰極層の厚さは、20nm~1μmであることが好ましく、特に30~200nmであることが好ましい。
陰極層の形成方法としては、特に制限はされず、例えば、真空蒸着、各種スパッタリング等の方法を適用できる。
〔基材〕
基材としては、用途に応じて適宜選択できるが、一般的には、ガラス(板)等の無機材料またはプラスチックフィルムが使用される。
プラスチックフィルムとしては、例えば、ポリエチレンテレフタレート、ポリエチレンナフタレート、テトラアセチルセルロース、シンジオタクチックポリスチレン、ポリフェニレンスルフィド、ポリカーボネート、ポリアリレート、ポリスルホン、ポリエステルスルホン、ポリエーテルイミド、環状ポリオレフィン等の樹脂からなるフィルムが挙げられ、中でも機械的強度、耐久性等に優れたものが好ましい。
基材の厚さは、機械的強度、耐久性の点から一般的には3μm~5mmであり、好ましくは10μm~1mmであり、特に好ましくは20μm~300μmである。
本発明の電子デバイスの製造方法は、陽極層上に前記の導電性接着剤組成物からなる導電層を形成して陽極積層体を形成させる工程と、陰極層上に前記光電変換層または発光層を形成して陰極積層体を形成させる工程と、前記導電性接着剤組成物が軟化する温度以上で、前記陰極積層体の光電変換層または発光層表面と前記陽極積層体の導電層表面を貼り合わせることを特徴としている。
以下、本発明の電子デバイスの製造方法を図1(b)により順に説明する。
陽極層1と導電層4を一体化したものを陽極積層体(後述する)と称する。2の陰極層と3の光電変換層または発光層を一体化したものを陰極積層体(後述する)と称する。
下向きの矢印は陽極積層体と陰極積層体を加熱下、圧着して一体化して電子デバイスとすることを表わしている。
陽極積層体は、陽極層1の上に本発明の導電性接着剤組成物からなる前記導電層4が形成されたものからなっている。
一般的には、陽極層は、基材上に設けられている。
基材上に陽極を設ける方法としては、真空蒸着、スパッタリング、イオンプレーティング等のPVD(物理気相蒸着)、もしくは熱CVD、原子層蒸着(ALD)等のCVD(化学気相蒸着)などのドライプロセス、またはディップコーティング、スピンコーティング、スプレーコーティング、バーコーティング、グラビアコーティング、ダイコーティング、ドクターブレード等の各種コーティングや電気化学的ディポジションなどのウェットプロセスが挙げられ、陽極層の材料に応じて適宜選択される。
陽極層上に導電層を形成させる形成方法は、導電性接着剤組成物を、精製水等の適当な溶剤に溶解又は分散してなる導電層形成用溶液を、陽極層上に塗付し、得られた塗膜を乾燥させ、所望により、導電性接着剤組成物中の有機添加剤が揮発しない程度で加熱することより形成することができる。形成方法としては、ディップコーティング、スピンコーティング、スプレーコーティング、バーコーティング、グラビアコーティング、ダイコーティング、ドクターブレード等の各種コーティングや電気化学的ディポジションなどのウェットプロセスが挙げられ、適宜選択される。
陰極積層体は、前記陰極層2の上に前記光電変換層または発光層3が形成されたものからなっている。
一般的には、陰極層2は、基材上に設けられている。
基材上に陽極層を設ける方法としては、真空蒸着、スパッタリング、イオンプレーティング等のPVD(物理気相蒸着)、もしくは熱CVD、原子層蒸着(ALD)等のCVD(化学気相蒸着)などのドライプロセス等が挙げられ、陰極層の材料に応じて適宜選択される。
陰極層上に光電変換層または発光層を形成させる形成方法は、真空蒸着、スパッタリング、イオンプレーティング等のPVD(物理気相蒸着)、もしくは熱CVD、原子層蒸着(ALD)等のCVD(化学気相蒸着)などのドライプロセス、またはディップコーティング、スピンコーティング、スプレーコーティング、グラビアコーティング、バーコーティング、ドクターブレード等の各種コーティングや電気化学的ディポジションなどのウェットプロセスによりが挙げられ、光電変換層または発光層の材料に応じて適宜選択される。
本発明の電子デバイスの製造方法は、本発明の導電性接着剤組成物からなる導電層表面と光電変換層または発光層表面を貼り合わせるため、ラミネートプロセスにより容易に電子デバイスを製造することができる。
また、この方法では、光電変換層または発光層を形成させた後に陰極層として金属層を形成させる工程が存在せず、金属層が不均一になったり、金属層成膜時のエネルギーによって光電変換層または発光層がダメージを受けることがないため、電子デバイスの性能が低下することがない。
[導電性接着剤組成物の調製]
成分(A)の水溶性ポリビニル重合体として、ポリビニルアルコール〔シグマアルドリッチ社製、製品名「ポリビニルアルコール」、分子量Mw=9100、Tg(T1):50℃、表1中ではPVAと記載〕50質量部を使用した。成分(B)の有機添加剤として、グリセリン〔シグマアルドリッチ社製、製品名「グリセリン」、融点(T2):18℃、沸点(T3):290℃〕50質量部を使用した。成分(C)の導電性高分子であるポリチオフェン類としてポリ(3,4-エチレンオキサイドチオフェン)(PEDOT)とポリスチレンスルホン酸(PSS)の混合物(PEDOT:PSS)〔H.C.Starck社製、製品名「CleviousP VP.AI4083、有効成分1質量%」、表1中ではポリチオフェン類と記載〕10,000質量部を使用した。
前記成分(A)、(B)および(C)を精製水200質量部に溶解させ、導電性接着剤組成物の塗工液(有効成分:1.9質量%)を調製した。
スズドープ酸化インジウム(ITO)層の厚さが150nmになるようにスパッタリングされたITOガラス〔テクノプリント社製、製品名「ITOガラス」〕を陽極層として用いた。
次いで、上記陽極層上に、上記で得られた導電性接着剤組成物の塗工液をスピンコート法により塗工し、100℃で30分間乾燥させ、厚さ100nmの導電性接着剤組成物からなる導電層を形成させた。
基材として、ポリエチレンテレフタレートフィルム〔東洋紡績社製、製品名「コスモシャインA4100」〕上に、1×10-3Pa以下の減圧下、アルミニウムを蒸着法で製膜することにより、厚さ100nmのアルミニウム層を成膜し、陰極層を形成させた。
次いで、光電変換層として、ポリ-3-ヘキシルチオフェン(P3HT)と[6,6]-フェニル-C61-酪酸メチル(PCBM)とを質量比1:0.8で混合した混合物のクロロベンゼン溶液(濃度:2%)を、スピンキャスト法により塗布し、120℃で10分間乾燥して、厚さ100nmの真性半導体層を形成させた。
得られた陽極積層体の導電層表面と、陰極積層体の光電変換層表面とをロールラミネーター〔ロイヤルソブリン社製、製品名「RSL-328S」〕のローラーの温度を120℃に加熱し圧着して貼り合わせることで電子デバイスを得た。
下記表1の配合に変える以外は実施例1と同様にして、電子デバイスを得た。
成分(B)の有機添加剤をN-メチルピロリドン〔和光純薬工業株式会社製、T2:融点-24℃、T3:沸点202℃〕に変えて、下記表1の配合に変える以外は実施例1と同様にして電子デバイスを得た。
成分(A)のPVAをポリビニルピロリドン〔シグマアルドリッチ社製、Tg(T1):80℃、表1中ではPVPと記載〕に変えて、下記表1の配合に変える以外は実施例1と同様にして電子デバイスを得た。
成分(A)のPVAをポリビニルピロリドン〔シグマアルドリッチ社製、Tg(T1):80℃〕に変え、成分(B)の有機添加剤をN-メチルピロリドン(T2:融点-24℃、T3:沸点202℃)に変えて、下記表1の配合に変える以外は実施例1と同様にして電子デバイスを得た。
成分(B)の有機添加剤をジメチルスルホキサイド〔和光純薬工業株式会社製、表1中の記載はDMSO、T2:融点19℃、T3:沸点189℃〕に変えて、下記表1の配合に変える以外は実施例1と同様にして電子デバイスを得た。
成分(B)の有機添加剤をジメチルフォルムアミド〔和光純薬工業株式会社製、表1中の記載はDMF、T2:融点-61℃、T3:沸点153℃〕に変えて、下記表1の配合に変える以外は実施例1と同様にして電子デバイスを得た。
成分(C)の導電性有機高分子化合物であるポリアニリン類としてポリアニリン〔シグマアルドリッチ株式会社製、有効成分1質量%、表1中ではポリアニリン類1と記載〕に変えて、下記表1の配合に変える以外は実施例1と同様にして電子デバイスを得た。
成分(C)の導電性有機高分子化合物であるポリピロール類としてポリピロール〔シグマアルドリッチ社製、有効成分1質量%、表1中ではポリピロール類と記載〕に変える以外は実施例1と同様にして電子デバイスを得た。
成分(A)、(B)、(C)を下記表1の配合にする以外は実施例1と同様にして、電子デバイスを得た。
実施例1~10で得られた導電層および電子デバイスの各物性および比較例1~7で得られた導電層の各物性を表1に示す。
[導電性接着剤組成物の調製]
成分(A)の水溶性ポリビニル重合体として、アクリル酸重合体〔シグマアルドリッチ製、製品名「ポリアクリル酸」、重量平均分子量100,000、有効成分:40質量%、Tg(T1):102℃、表2中ではPAAと記載〕を有効成分として45質量部を使用した。成分(B)の有機添加剤として、グリセリン〔シグマアルドリッチ社製、製品名「グリセリン」、融点(T2):18℃、沸点(T3):290℃〕90質量部を使用した。成分(C)の導電性高分子であるポリチオフェン類としてポリ(3,4-エチレンオキサイドチオフェン)(PEDOT)とポリスチレンスルホン酸(PSS)の混合物(PEDOT:PSS)〔H.C.Starck社製、製品名「CleviousP VP.AI4083」、有効成分1質量%、表2中ではポリチオフェン類と記載〕を1500質量部(有効成分としては15質量部)使用した。前記成分(A)、(B)および(C)を精製水200質量部に溶解させ、導電性接着剤組成物の塗工液(有効成分:7.8質量%)を調製した。
下記表2の配合に変えて、かつ、導電層の厚さを1,000nmとした以外は実施例1と同様に行って、陽極積層体を作製した。
[陰極積層体の作製]
導電層を下記表2の配合に変えて、かつ、光電変換層として、厚さ1,000nmの真性半導体層を形成させ、陰極積層体において光電変換層を形成させた以外は実施例1と同様に行った。
得られた陽極積層体の導電層表面と、陰極積層体の光電変換層の表面とをロールラミネーター〔ロイヤルソブリン社製、製品名「RSL-328S」〕のローラーの温度を100℃に加熱し圧着して貼り合わせることで電子デバイス(太陽電池)を得た。
[陰極積層体の作製]
基材として、ポリエチレンテレフタレートフィルム〔東洋紡績株式会社製、製品名「コスモシャインA4100」〕上に、1×10-3Pa以下の減圧下、銀を蒸着法で厚さが100nmになるように製膜し、次いでマグネシウムを厚さが10nmになるように蒸着することで、陰極層を形成させた。
次いで、株式会社Luminescence Technology製の(ポリ(2-メトキシ-5-(3′,7′-ジメチルオクチルオキシ)-1,4-フェニレン-ビニレン))〔商品名「MDMO-PPV」〕をキシレンに溶解(濃度:1質量%)し、スピンキャスト法により塗布し、100℃で10分間乾燥して、厚さ100nmの発光層を形成させた。
[貼り合わせによる電子デバイス(有機EL素子)の作製]
下記表2の配合に変えて、かつ、導電層の厚さを1,000nmとした以外は実施例1と同様に行って得られた陽極積層体の導電層表面と、陰極積層体の発光層の表面とをロールラミネーター〔ロイヤルソブリン社製、製品名「RSL-328S」〕のローラーの温度を100℃に加熱し圧着して貼り合わせることで電子デバイス(有機EL素子)を得た。
下記表2の配合に変えた以外は実施例11と同様にして、電子デバイス(太陽電池および有機EL素子)を得た。
下記表2の配合に変えた以外は実施例11と同様にして、電子デバイス(太陽電池および有機EL素子)を得た。
<実施例16>
成分(C)の導電性有機高分子化合物であるポリアニリン類としてポリアニリン〔日産化学工業株式会社製、製品名「D1033W」、表2中ではポリアニリン類2と記載〕に変えて、下記表1の配合に変える以外は実施例1と同様にして電子デバイスを得た。
成分(A)、(B)、(C)を下記表2の配合とし、導電層の厚さを下記表2に記載のものとした以外は実施例11と同様にして、電子デバイス(太陽電池および有機EL素子)を得た。ただし、比較例11~14においては、陽極積層体の導電層表面と、陰極積層体の光電変換層または発光層の表面貼り合わせることができず電子デバイスを作製することができなかった。
実施例11~17および比較例8~10、15で得られた導電層および電子デバイスの各物性を表2に示す。
(1)アクリル酸重合体(表2中ではPAAと記載)
シグマアルドリッチ製、製品名「ポリアクリル酸」
(3)グリセリン
シグマアルドリッチ社製、製品名「グリセリン」
(4)N-メチルピロリドン
和光純薬工業株式会社製、製品名「N-メチルピロリドン」
(5)ジメチルスルホキシド(表2ではDMSOと記載)
和光純薬工業株式会社製、製品名「ジメチルスルホキシド」
(6)N,N-ジメチルホルムアミド(表2ではDMFと記載)
和光純薬工業株式会社製、製品名「N,N-ジメチルホルムアミド」
(7)ポリチオフェン類
H.C.Starck社製、製品名「CleviousP VP.AI4083」
(8)ポリアニリン類1
シグマアルドリッチ株式会社製、製品名「ポリアニリン」(実施例9)
ポリアニリン類2
日産化学工業株式会社製、製品名「D1033W」(実施例16)
(9)ポリピロール類
シグマアルドリッチ社製、製品名「ポリピロール」
(1)導電層の厚さ
導電性接着剤組成物からなる導電層の厚さは、触針式表面形状測定装置〔Veeco社製、製品名「Dektak150」〕により測定した。
(2)表面抵抗値
得られた陽極積層体の導電層表面を、表面抵抗測定装置〔三菱化学社製、製品名「ロレスタGP MCP-T600」〕により、四端子法で導電層の表面抵抗値を測定した。
(3)全光線透過率
得られた陽極積層体を、光線透過率測定装置〔日本電色工業社製、製品名「NDH-5000」〕を用いてJIS K7631-1に準じて、全光線透過率を測定し、導電層の全光線透過率とした。
(4)接着性
実施例および比較例で得られた導電性接着剤組成物の塗工液をポリエチレンテレフタレートフィルム〔東洋紡績社製、製品名「コスモシャインA4100」、厚み100μm〕上に塗工し、100℃で10分間乾燥させ、膜厚100nmの導電性接着剤組成物からなる導電層を形成させ、測定用サンプル(5×5cm)を作製した。
得られた測定用サンプルを、ラミネーター〔ロイヤルソブリン社製、製品名「RSL-328J」〕を用いて、温度120℃でガラス板(25mm×25mm、厚み1mm)に貼り合わせた。その後、常温まで冷却後、測定用サンプルを垂直にし、接着しているか否かを調べた。
下記の基準で″貼り合わせ評価″として表1および表2に記載した。
○:ガラス板から測定用サンプルが落ちずに接着している。
×:接着せずにガラス板から測定用サンプルが剥離した。
(5)接着力
表2に記載されている接着力は、実施例11~17および比較例8~10で得られた導電性接着剤組成物の塗工液をポリエチレンテレフタレートフィルム〔東洋紡績社製、製品名「コスモシャインA4100」、厚み100μm〕上に塗工し、100℃で10分間乾燥させ、膜厚1,000nmの導電性接着剤組成物からなる導電層を形成させ、測定用サンプルを作製した。
得られた測定用サンプルを、を用いてJIS Z0237(2009)に準じて、23℃、50%RH(相対湿度)環境下で25mm×300mmにカットした測定用サンプルをラミネーター〔ロイヤルソブリン社製、製品名「RSL-328J」〕を用いて、温度100℃で被着体(ガラス板、800mm×1500mm、厚み3mm)に貼り合わせた。貼付後24時間時点の粘着力を180°引き剥がし法によって、引っ張り速度300mm/分にて測定した。
(6)ガラス転移温度
成分(A)の水溶性ビニル重合体のガラス転移温度T1は、JIS K 7121に準拠し、入力補償示差走査熱量測定装置〔パーキンエルマー社製、装置名「Pyrisl DSG」〕を用いて、-80℃から250℃の温度範囲で、捕外ガラス転移開始温度を測定して求めた。
実施例および比較例で得られた電子デバイスを、ソースメジャーユニット〔ワコム電創社製〕を用いて電流電圧特性を測定し、得られた整流曲線を観察した。
○:整流性有
×:整流性無(貼り合せ不良により電子デバイスとして機能しない)
実施例11の配合で得られた電子デバイス(太陽電池)に関して得られた電流密度-電圧曲線を図2に示す。
実施例11~17および比較例8~10、15で得られた電子デバイス(有機EL素子)の電流-電圧特性は有機EL発光効率測定装置〔PRECISE GAUGES社製、製品名「EL1003」〕を用いて電流電圧特性を測定し、得られた整流曲線を観察した。
○:整流性有
×:整流性無(貼り合せ不良により電子デバイスとして機能しない)
また、電圧印加時の電子デバイス(有機EL素子)の輝度(cd/cm2)は輝度計〔コニカミノルタ社製、製品名「LS-110」〕を用いて測定を行った。結果を表2に示す。
(A)成分のみからなる比較例3および4、(A)成分と(C)成分からなる比較例1および2の導電性接着剤組成物からなる導電層では、表面抵抗が高く、得られた電子デバイスは整流性が見られず、デバイスとして機能しなかった。
(B)成分のみからなる比較例5および6の導電性接着剤組成物では、成膜性が悪く、導電層の膜形成が出来なかった。また、(C)成分のみからなる比較例7の導電性接着剤組成物からなる導電層は、接着性がなく、貼り合わせにより電子デバイスを作製することが出来なかった。
一方、成分(A)、(B)および(C)からなる実施例1~10の導電性接着剤組成物からなる導電層では、表面抵抗値が低く透明性も高かった。また、接着性も良好であるため、貼り合わせによる電子デバイスの作製が良好に出来、かつ得られた電子デバイスも整流性があったことからデバイスとしても有効であることがわかった。
(A)成分のみからなる比較例10の導電性接着剤組成物からなる導電層では、表面抵抗が高く、得られた電子デバイス(太陽電池)は整流性が見られず、デバイスとして機能しなかった。また、得られた電子デバイス(有機EL素子)のEL特性(輝度)の測定を試みたが発光しなかった。
(A)成分と(C)成分のみからなる比較例8および9の導電性接着剤組成物からなる導電層では、表面抵抗が高く、得られた電子デバイス(太陽電池)は整流性が見られず、デバイスとして機能しなかった。また、それらのEL特性(輝度)の測定をしたが輝度が低かった。(B)成分のみからなる比較例11~14の導電性接着剤組成物においては、成膜性が悪く、導電層の膜形成が出来なかった。また、(C)成分のみからなる比較例15の導電性接着剤組成物からなる導電層は、導電層の接着性がなく、貼り合わせにより電子デバイスを作製することが出来なかった。
一方、成分(A)、(B)および(C)からなる実施例11~17の導電性接着剤組成物からなる導電層では、表面抵抗値が低く透明性も高かった。また、接着性も良好であるため、貼り合わせによる電子デバイスの作製が良好に出来、かつ得られた電子デバイスも整流性があったことからデバイスとしても有効であることがわかった。また、それらのEL特性(輝度)は高く良好であった。
2:陰極層
3:光電変換層または発光層
4:導電層
Claims (8)
- (A)水溶性ポリビニル重合体、(B)有機添加剤及び(C)導電性有機高分子化合物を含む導電性接着剤組成物であって、
(B)有機添加剤は水溶性多価アルコール、水溶性ピロリドン類または親水性の非プロトン性溶媒から選ばれる少なくとも一種であり、(C)導電性有機高分子化合物は、ポリアニリン類、ポリピロール類またはポリチオフェン類及びその誘導体から選ばれる少なくとも1種であることを特徴とする導電性接着剤組成物。 - 水溶性ポリビニル重合体のガラス転移温度をT1、(B)有機添加剤の融点をT2、有機添加剤の0.101MPa(760mmHg)における沸点をT3としたときに、T2<T1<T3を満たす請求項1に記載の導電性接着剤組成物。
- 水溶性ポリビニル重合体が、ポリビニルアルコール、ポリビニルピロリドン及びポリアクリル酸から選ばれる少なくとも1種である請求項1に記載の導電性接着剤組成物。
- 請求項1に記載の導電性接着剤組成物からなる導電層を有することを特徴とする電子デバイス。
- 陽極層と、請求項1に記載の導電性接着剤組成物からなる導電層と、光電変換層と、陰極層をこの順に配置してなる請求項4に記載の電子デバイス。
- 陽極層と、請求項1に記載の導電性接着剤組成物からなる導電層と、発光層と、陰極層をこの順に配置してなる請求項4に記載の電子デバイス。
- 基材上に陽極層、請求項1に記載の導電性接着剤組成物からなる導電層がこの順に積層されてなることを特徴とする陽極積層体。
- 請求項4に記載の電子デバイスの製造方法であって、
陽極層上に前記請求項1に記載の導電性接着剤組成物からなる導電層を形成して陽極積層体を形成させる工程と、陰極層上に前記光電変換層又は発光層を形成して陰極積層体を形成させる工程と、前記導電性接着剤組成物が軟化する温度以上で、前記陰極積層体の光電変換層又は発光層表面と前記陽極積層体の導電層表面を貼り合わせることを特徴とする電子デバイスの製造方法。
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JP2020527974A (ja) * | 2017-07-27 | 2020-09-17 | ヘレウス ドイチェラント ゲーエムベーハー ウント カンパニー カーゲー | 自己粘着性電極貼付剤 |
JP7216702B2 (ja) | 2017-07-27 | 2023-02-01 | ヘレウス ドイチェラント ゲーエムベーハー ウント カンパニー カーゲー | 分散液、層状体(1)、層状体(1)を製造する方法、層状体(1)の使用、および治療的送電システムまたは受電システム |
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JP7100603B2 (ja) | 2019-03-22 | 2022-07-13 | 信越ポリマー株式会社 | 導電性接着剤組成物、導電性接着構造体及びその製造方法、並びに導電性積層体及びその製造方法 |
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Publication number | Publication date |
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EP2623574A1 (en) | 2013-08-07 |
CN103189463B (zh) | 2015-12-09 |
KR20130086352A (ko) | 2013-08-01 |
TW201224107A (en) | 2012-06-16 |
TWI488940B (zh) | 2015-06-21 |
EP2623574A4 (en) | 2014-06-18 |
JP5690833B2 (ja) | 2015-03-25 |
US20130306943A1 (en) | 2013-11-21 |
JPWO2012043025A1 (ja) | 2014-02-06 |
KR101488628B1 (ko) | 2015-01-30 |
US9159940B2 (en) | 2015-10-13 |
CN103189463A (zh) | 2013-07-03 |
EP2623574B1 (en) | 2016-06-15 |
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