WO2010010791A1 - 有機トランジスタ及びその製造方法 - Google Patents
有機トランジスタ及びその製造方法 Download PDFInfo
- Publication number
- WO2010010791A1 WO2010010791A1 PCT/JP2009/061837 JP2009061837W WO2010010791A1 WO 2010010791 A1 WO2010010791 A1 WO 2010010791A1 JP 2009061837 W JP2009061837 W JP 2009061837W WO 2010010791 A1 WO2010010791 A1 WO 2010010791A1
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- WO
- WIPO (PCT)
- Prior art keywords
- organic
- organic semiconductor
- transistor
- insulating layer
- fluorine
- Prior art date
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Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
-
- 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
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
- H10K10/488—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions the channel region comprising a layer of composite material having interpenetrating or embedded materials, e.g. a mixture of donor and acceptor moieties, that form a bulk heterojunction
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
-
- 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
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/15—Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used
Definitions
- the present invention relates to an organic transistor using an organic semiconductor used for a liquid crystal display, electronic paper, an EL display device, an RF-ID tag, and the like, and a method for manufacturing the same.
- Transistors are widely used as important electronic elements (electronic parts) that make up televisions and computer equipment, and are currently manufactured using inorganic materials such as silicon as the main material.
- organic transistors using an organic substance as a member of such a transistor has attracted attention (see Non-Patent Document 1).
- Organic transistors can be formed by a wet process such as a printing method, so there is no need for expensive vacuum equipment, which was essential in conventional silicon processes, and production costs including capital investment can be drastically reduced.
- An organic transistor is an organic semiconductor element having three electrodes, an insulating layer, and a semiconductor layer as essential members.
- a wet process such as a printing method and a dry process such as vacuum deposition and sputtering as a method for forming an electrode layer, an insulating layer, and a semiconductor layer constituting the element, but a wet process is preferable in view of cost reduction (non-patent) Reference 2).
- the surface of the gate insulating layer is treated with a surface treatment agent typified by a silane coupling agent for the purpose of improving the crystallinity of the organic semiconductor layer constituting the channel formation region.
- a surface treatment agent typified by a silane coupling agent for the purpose of improving the crystallinity of the organic semiconductor layer constituting the channel formation region.
- an example in which a channel formation region is formed using an organic semiconductor material thereon has been introduced (see Non-Patent Document 3 and Patent Document 1).
- an ideal surface treatment that completely covers the substrate surface with silane coupling without any gap inevitably increases the liquid repellency of the insulating film surface.
- the surface treatment is performed by applying a limited silane coupling agent, limiting processing conditions, or using a limited solvent.
- a limited silane coupling agent limiting processing conditions, or using a limited solvent.
- the solvent that can be used is limited, so that the wet process method is inevitably limited, which is the most characteristic of the organic transistor, flexible. Therefore, it has been difficult to realize a large-area transistor element at a practical level.
- Examples of adding a resin to an organic semiconductor solution include P3HT (Poly (3-hexylthiophene)) and PQT-12 (poly [5,5′-bis (3-dodecyl-2-thienyl) -2,2′-bithiophene). And a polymethyl methacrylate resin dissolved in dichlorophenol is used.
- a PMMA having a protective film function was spontaneously separated into layers by spin-coating the blend solution on a silicon oxide insulating film surface-treated with a silane coupling agent, and formed on the silicon oxide. It has been shown that a layer separation structure covering an organic semiconductor layer is formed (see Non-Patent Document 4).
- a fluorosurfactant there is no description regarding the addition of a fluorosurfactant, and there is no finding that the performance of a transistor element can be improved by using an organic semiconductor to which a fluorosurfactant is added.
- An object of the present invention is to provide an organic transistor having an improved transistor characteristic in an organic transistor using an organic semiconductor and a method for manufacturing the same.
- the present invention provides: (a) a substrate, (b) a gate electrode, (c) an insulating layer, (d) a channel forming region formed in an organic semiconductor layer in contact with the insulating layer, and (e) a source.
- a substrate is provided with (b) a gate electrode, (c) an insulating layer, (d) a channel formation region formed in an organic semiconductor layer in contact with the insulating layer, and (e) a source / drain electrode.
- D a step of forming an organic semiconductor layer by printing or coating an organic semiconductor solution containing a fluorine-based surfactant on the insulating layer, or (d) a fluorine-based method
- the present invention provides a method for producing an organic transistor comprising a step of forming an insulating layer by printing or coating on an organic semiconductor layer containing a surfactant.
- transistor characteristics can be improved by forming an organic semiconductor layer containing a fluorine-based compound (surfactant) in an organic transistor.
- the effect of improving characteristics is high in an organic semiconductor having crystallinity. This is presumed that the addition of the fluorosurfactant increases the alignment and crystallinity of the organic semiconductor molecules and improves the transistor performance, but of course this does not limit the present invention.
- an organic semiconductor containing a fluorosurfactant by using an organic semiconductor containing a fluorosurfactant, it is difficult to form an organic semiconductor film in the past. Can be easily formed.
- high-performance organic materials that exhibit uniform and excellent transistor characteristics even on wet processes such as printing methods, even on highly liquid-repellent insulating films that are highly SAM-treated with various silane coupling agents.
- a semiconductor thin film can be formed easily.
- the present invention relates to an organic transistor element, and its structure is formed on (a) a substrate, (b) a gate electrode, (c) an insulating layer, and (d) an organic semiconductor layer in contact with the insulating layer.
- the present invention relates to an organic transistor having a channel formation region and (e) source / drain electrodes.
- the organic semiconductor layer is characterized by containing a fluorine compound (surfactant).
- the organic transistor of the present invention is manufactured by the following process. That is, it includes (a) a step of forming a gate electrode on a substrate, (c) a step of forming an insulating layer, and (d) a step of forming an organic semiconductor layer in contact with the insulating layer.
- the relative positional relationship between (c) the insulating layer and (d) the organic semiconductor layer in contact with the insulating layer is, for example, that the organic semiconductor layer may be formed after the insulating layer is formed.
- An insulating layer may be formed after the semiconductor layer is formed.
- Each layer is preferably formed by printing or coating.
- the organic transistor of the present invention can have a horizontal and vertical transistor structure.
- a bottom-gate (BG) or top-gate (TG) transistor defined by the positional relationship of the gate electrode with the transistor component can be used.
- a transistor structure such as a bottom contact type, a top contact type, and a bottom top contact type can be adopted.
- an organic semiconductor layer containing a fluorosurfactant when forming a bottom gate type organic transistor, an organic semiconductor layer containing a fluorosurfactant may be stacked after forming an insulating layer, or a top gate type organic transistor is formed.
- the insulating layer may be formed after the organic semiconductor layer containing the fluorosurfactant is formed.
- the substrate applicable to the organic transistor of the present invention.
- silicon thermally oxidized film silicon whose surface is oxidized to be an insulating layer, glass, stainless steel and other thin metal plates
- PC polycarbonate
- PET polyethylene terephthalate
- PET polyethylene terephthalate
- PI polyimide
- PES polyethersulfone
- PEN polyethylene naphthalate
- composite films obtained by adding a gas barrier property and a hard coat layer to these films can be used.
- a plastic film can be suitably used from the viewpoint of making the transistor flexible.
- the method for forming each functional layer excluding the organic semiconductor layer is not particularly limited, and may be a dry process or a wet process.
- the gate electrode (b) can be formed by a dry process represented by sputtering, vapor deposition, ion plating, photolithography, etching, or a wet process such as a printing method.
- the wet process is a preferred embodiment of the present invention because a dramatic reduction in manufacturing cost can be expected.
- inkjet method for example, inkjet method, screen printing method, spin coating method, bar coating method, slit coating method, dip coating method, spray coating method, gravure printing method, flexographic printing method, gravure offset method, letterpress offset method, micro A contact printing method, a letterpress reverse printing method, or the like is used.
- the conductive ink for forming the gate electrode for example, gold, silver, copper, nickel, zinc, aluminum, calcium, magnesium, iron, platinum, palladium, tin, chromium, lead in a suitable solvent
- Metal particles such as silver, alloys of these metals such as silver / palladium, etc., thermally decomposable metal compounds that give a conductive metal by thermal differentiation at relatively low temperatures, such as silver oxide, organic silver, and organic gold, zinc oxide (ZnO)
- conductive metal oxide particles such as indium tin oxide (ITO) may be included as a conductive component, and conductive polymers such as polyethylenedioxythiophene / polystyrene sulfonic acid (PEDOT / PSS) and polyaniline are included.
- distribution of this electroconductive material can be selected suitably.
- various organic solvents such as water, hydrocarbon, alcohol, ketone, ether, ester, and fluorine can be used.
- the ink contains a binder component such as a resin, an antioxidant, various catalysts for promoting film formation, various interfacial energy regulators, leveling agents, mold release accelerators, and the like as necessary. Can be added.
- the ink in which nano silver particles are dispersed in a solvent and mixed with a release agent such as low molecular silicone and an interfacial energy modifier such as a fluorosurfactant is particularly suitable for the relief offset method. It can be suitably used because it exhibits excellent patterning properties and high conductivity at low temperature firing. Conversion from the ink film layer to the functional material layer that constitutes the electronic component is a method that is optimal for the ink characteristics and the electronic component, such as room temperature drying, heat treatment, and treatment such as ultraviolet ray and electron beam irradiation. Can be implemented.
- the method for forming each functional layer excluding the organic semiconductor layer is not particularly limited, and may be a dry process or a wet process.
- a dry process represented by sputtering, vapor deposition, ion plating, photolithography, etching, or a wet process such as a printing method can be applied.
- the wet process is a preferred embodiment of the present invention because a dramatic reduction in manufacturing cost can be expected.
- inkjet method for example, inkjet method, screen printing method, spin coating method, bar coating method, slit coating method, dip coating method, spray coating method, gravure printing method, flexographic printing method, gravure offset method, letterpress offset method, letterpress A reverse printing method or the like is used.
- the insulating ink for forming the insulating layer (c) may contain an insulating material, such as an epoxy resin, a polyimide resin, a polyvinyl pyrrolidone resin, a polyvinyl alcohol resin, an acrylic resin.
- an insulating material such as an epoxy resin, a polyimide resin, a polyvinyl pyrrolidone resin, a polyvinyl alcohol resin, an acrylic resin.
- Nitrile resins, methacryl resins, polyamide resins, polyvinyl phenol resins, phenol resins, polyamide imide resins, fluorine resins, melamine resins, urethane resins, polyester resins, alkyd resins, and the like can be applied.
- these may be used alone or in combination of two or more, and if necessary, constitutions such as high relative dielectric constant particles such as alumina fine particles, silica fine particles and tantalum oxide fine particles, and low relative dielectric constant particles such as hollow silica fine particles Ingredients may be added.
- various organic solvents such as water, hydrocarbon type, alcohol type, ketone type, ether type, ester type, glycol ether type, a fluorine type, can be used.
- binder components such as resin, antioxidant, a leveling agent, a mold release accelerator, and various catalysts for film formation promotion can be used as needed.
- silicone-based and fluorine-based surfactants can be added. Conversion from the ink film layer to the functional material layer that constitutes the transistor is performed in a method that is optimal for the ink characteristics and electronic components, such as room temperature drying, heat treatment, and ultraviolet light, electron beam irradiation, etc. it can.
- the gate electrode (b) and the insulating layer (c) may be formed by a dry process or a wet process.
- the formation of the organic semiconductor layer (d) is characterized by requiring a wet process such as a printing method.
- a solvent-soluble organic semiconductor that can be wet-processed can be applied.
- Solvent-soluble organic semiconductors such as P3HT (poly (3-hexylthiophene)), PQT-12 (poly [5,5′-bis (3-dodecyl-2-thienyl1) -2,2′-bithiophene]), etc.
- Thiophene-thienothiophene such as PB10TTT, PB12TTT, PB14TTT, PB16PBTTT (PBTT: poly (2,5-bis (3-alkylthiophen-2-yl) thieno [3,2-b] thiophene)) Copolymers, soluble thiophene oligomers, fluorene polymers such as F8T2, phenylene vinylene polymers, triarylamine polymers, TIPS pentacene, and precursors and mixtures of these organic semiconductors can be suitably used.
- PBTT poly (2,5-bis (3-alkylthiophen-2-yl) thieno [3,2-b] thiophene)
- P3HT poly (3-hexylthiophene)
- PQT-12 poly [5,5′-bis (3-dodecyl-2-thienyl1) -2,2′-bithiophene]
- Polythiophene polymers such as PB10TTT, PB12TTT, PB14TTT, PB16PBTTT, etc.
- PBTT poly (2,5-bis (3-alkylthiophen-2-yl) thieno [3,2-b] thiophene)
- a copolymer or a mixture of two or more of TIPS pentacene is preferred.
- Solvents applicable to these organic semiconductor inks only need to be able to dissolve the organic semiconductor at room temperature or with some heating, have appropriate volatility, and form an organic semiconductor thin film after volatilization of the solvent.
- toluene, xylene, mesitylene Chlorobenzene solvents such as chloroform, anisole, methylene chloride, tetrahydrofuran, cyclohexanone, dichlorobenzene and trichlorobenzene, and fluorinated solvents may be used alone or as a mixed solvent containing these solvents.
- the organic semiconductor ink for forming the organic semiconductor layer in the organic transistor of the present invention is characterized by containing a fluorine-based surfactant.
- a fluorosurfactant for a crystalline organic semiconductor ink contributes not only to improving ink characteristics but also to improving characteristics of a semiconductor film formed by drying the ink, such as field effect mobility.
- a small amount of a silicone-based or hydrocarbon-based surfactant can be supplementarily added.
- an organic transistor has a surface of a gate insulating film, for example, hexamethyldisilazane (HMDS), octyltrichlorosilane (OTS-8), octadecyltrichlorosilane, (OTS-18), dodecyltrichlorosilane (DTS), fluorine.
- HMDS hexamethyldisilazane
- OTS-8 octyltrichlorosilane
- OTS-18 dodecyltrichlorosilane
- Transistor characteristics are improved by applying a SAM (self-assembled film) treatment with a silane coupling agent such as substituted octatrichlorosilane (PFOTS) or ⁇ -phenethyltrichlorosilane.
- POTS substituted octatrichlorosilane
- ⁇ -phenethyltrichlorosilane ⁇ -phenethy
- a densely SAM-treated surface inevitably increases liquid repellency, and it has been difficult to form a uniform organic semiconductor thin film on the surface. For this reason, there are significant limitations on the applicable transistor structure, solvent type, and printing method.
- a fluorosurfactant to the organic semiconductor ink and adjusting the surface energy of the organic semiconductor ink or organic semiconductor film, a uniform organic semiconductor can be easily formed on the gate insulating film having high liquid repellency. A layer can be formed.
- the optimum SAM treatment agent and conditions for the type of organic semiconductor to be applied can be selected without limitation, and transistor characteristics that have not been achieved so far are realized.
- the fluorosurfactant a surfactant in which a fluorine-containing group, a hydrophilic group and / or a lipophilic group are present in the same molecule can be used.
- the fluorine-containing group is not particularly limited, but a perfluoroalkyl group in which all or part of the alkyl group's hydrogen atoms are substituted with fluorine atoms, or a perfluoroalkyl group having a structure in which the perfluoroalkyl group has an oxygen atom interposed therebetween.
- Polyether groups are preferred.
- the fluorine-containing group is a perfluoroalkyl group, the number of carbon atoms is preferably 6 or more.
- the fluorosurfactant is preferably a fluorinated (meth) acrylic polymer.
- the fluorine-containing group may be present in any of the main chain, the side chain, and the molecular end.
- the fluorine-containing group is preferably present in the side chain, and it is industrially simple and preferable to obtain a polymer using fluorinated (meth) acrylate as a raw material.
- (meth) acrylate methacrylate, acrylate, haloacrylate, and cyanoacrylate are collectively referred to as (meth) acrylate.
- the fluorinated (meth) acrylate is represented by the following general formula (A-1).
- CH 2 C (R 1 ) COO (X) a C m F 2m + 1 (A-1)
- X is a divalent linking group, specifically, — (CH 2 ) n —, —CH 2 CH (OH) (CH 2 ) n -,-(CH 2 ) n N (R 2 ) SO 2 -,-(CH 2 ) n N (R 2 ) CO- (where n is an integer from 1 to 10 and R 2 is H Or an alkyl group having 1 to 18 carbon atoms.), —CH (CH 3 ) —, —CH (CH 2 CH 3 ) —, —C (CH 3 ) 2 —, —CH (CF 3 ) —, — C (CF 3 ) 2 —, CH 2 CFH— and the like, a is 0 or 1, and m is an integer of 1 to 20.)
- fluorinated (meth) acrylate examples include the following.
- the fluorinated (meth) acrylic polymer is preferably a copolymer with non-fluorine (meth) acrylate in consideration of compatibility with other components.
- a non-fluorine (meth) acrylate is not particularly limited, but a macromonomer type non-fluorine (meth) acrylate containing a polyoxyalkylene group is preferable from the viewpoint of compatibility with other components.
- non-fluorine (meth) acrylates other than those described above.
- examples of such compounds include styrene, butadiene, nucleus-substituted styrene, acrylonitrile, vinyl chloride, vinylidene chloride, vinyl pyridine, N-vinyl pyrrolidone, vinyl sulfonic acid, vinyl acetate, butyl vinyl ether, cyclohexyl vinyl ether, hydroxyl butyl vinyl ether, and other vinyl ethers.
- ⁇ , ⁇ -ethylenically unsaturated carboxylic acids that is, mono- or divalent carboxylic acids such as acrylic acid, methacrylic acid, maleic acid, fumaric acid, itaconic acid, ⁇ , ⁇ -ethylenically unsaturated carboxylic acids
- Metal acrylic acid alkyl ester having 1 to 18 carbon atoms in the alkyl group as a derivative (hereinafter, this expression generically refers to both acrylic acid alkyl ester and methacrylic acid alkyl ester), that is, (meth) acrylic acid Methyl, Tyl, propyl, butyl, octyl, 2-ethylhexyl, decyl, dodecyl, stearyl ester, etc., and hydroxyalkyl esters of (meth) acrylic acid having 1 to 18 carbon atoms, ie, 2-hydroxyethyl ester, hydroxypropyl ester, hydroxybutyl Examples of the ester
- aminoalkyl esters of (meth) acrylic acid having 1 to 18 carbon atoms that is, dimethylaminoethyl ester, diethylaminoethyl ester, diethylaminopropyl ester, etc.
- acrylic acid containing ether oxygen having 3 to 18 carbon atoms Alkyl esters such as methoxyethyl ester, ethoxyethyl ester, methoxypropyl ester, methyl carbyl ester, ethyl carbyl ester, butyl carbyl ester and the like, and further cyclic structure-containing monomers such as dicyclopentanyloxyl ethyl (meth) acrylate, isobol Nyloxylethyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, dimethyladamantyl (meth) acrylate, dicyclopentanyl (
- non-fluorinated (meth) acrylates may be used alone or in combination of two or more.
- the production method of the fluorinated (meth) acrylic polymer according to the present invention is not limited at all, and a known method, that is, a solution polymerization method based on a polymerization mechanism such as a radical polymerization method, a cationic polymerization method, an anionic polymerization method, although it can be produced by a bulk polymerization method or an emulsion polymerization method, the radical polymerization method is particularly convenient and industrially preferable.
- the polymerization initiator those known in the art can be used, for example, peroxides such as benzoyl peroxide and diacyl peroxide, and azo compounds such as azobisisobutyronitrile and phenylazotriphenylmethane. And metal chelate compounds such as Mn (acac) 3 .
- the molecular weight of the polymer can also be controlled by the polymerization method, polymerization initiator, etc., but chain transfer agents known in the industry can be used as necessary. Examples of the chain transfer agent include lauryl mercaptan, 2-mercaptoethanol, ethylthioglycolic acid, octylthioglycolic acid and the like.
- the fluorine-based random or block copolymer according to the present invention can also be obtained by photopolymerization in the presence of a photosensitizer or photoinitiator, or by polymerization using radiation or heat as an energy source.
- the polymerization can be carried out in the presence or absence of a solvent, but is preferably in the presence of a solvent from the viewpoint of workability.
- Solvents include ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, esters such as methyl acetate, ethyl acetate, butyl acetate, polar solvents such as dimethylformamide, dimethyl sulfoxide, 1,1,1-trichloroethane, chloroform, etc. Any of the above halogenated solvents, ethers such as tetrahydrofuran and dioxane, aromatics such as benzene, toluene and xylene, and fluorinated inner-trikids such as perfluorooctane and perfluorotri-n-butylamine can be used. .
- the molecular weight of the fluorinated (meth) acrylic polymer according to the present invention is preferably 3,000 to 1,000,000, preferably 5,000 to 500,000, and more preferably 10,000 to 1,000, in terms of weight average molecular weight. 300,000 is good.
- the fluorine-containing surfactant to be added may be one kind or a mixture of two or more kinds.
- a small amount of silicone-based or hydrocarbon-based surfactant can be mixed with the fluorine-based surfactant.
- Specific examples include, for example, Megafuck F-482, Megafuck F-470 (R-08), Megafuck F-472SF, Megafuck R-30, Megafuck F-484, Megafuck F-486, There are MegaFuck F-172D, MegaFuck MCF-350SF, MegaFuck F-178RM (trade name, manufactured by DIC), etc., but there is no particular limitation. These may be used alone or in combination of two or more.
- These fluorinated surfactants are contained in the total ink composition in an amount of 0.01 to 5.0% by mass, preferably 0.05 to 1.0% by mass of the active component.
- fluorine surfactants with high surface segregation properties is particularly effective in improving transistor characteristics such as field effect mobility and ON / OFF ratio.
- An organic semiconductor layer containing a fluorosurfactant can be easily formed by a wet process.
- inkjet method screen printing method, spin coating method, bar coating method, slit coating method, dip coating method, spray coating method, gravure printing method, flexographic printing method, gravure offset method, relief printing offset method, micro contact printing method, relief printing A reverse printing method or the like can be used.
- the formation of the source and drain electrodes (e) is not particularly limited, and may be a dry process or a wet process. Similar to the formation of the gate electrode (b), a dry process represented by sputtering, vapor deposition, ion plating, photolithography, and etching, and a wet process such as a printing method can be applied. In particular, the wet process is a preferred embodiment of the present invention because a significant reduction in manufacturing cost can be expected.
- inkjet method for example, inkjet method, screen printing method, spin coating method, bar coating method, slit coating method, dip coating method, spray coating method, gravure printing method, flexographic printing method, gravure offset method, letterpress offset method, micro A contact printing method, a letterpress reverse printing method, or the like is used.
- the conductive ink for forming the source and drain electrodes (e) is, for example, gold, silver, copper, nickel, zinc, aluminum in an appropriate solvent, as in the formation of the gate electrode (b). , Calcium, magnesium, iron, platinum, palladium, tin, chromium, lead, etc. metal particles such as silver / palladium alloys, silver oxide, organic silver, organic gold, etc.
- conductive metal oxide particles such as zinc oxide (ZnO) and indium tin oxide (ITO) may be included as a conductive component, or polyethylenedioxythiophene / polystyrenesulfonic acid Conductive polymers such as (PEDOT / PSS) and polyaniline may be included.
- conductive metal oxide particles such as zinc oxide (ZnO) and indium tin oxide (ITO)
- ZnO zinc oxide
- ITO indium tin oxide
- PES polyethylenedioxythiophene / polystyrenesulfonic acid
- Conductive polymers such as (PEDOT / PSS) and polyaniline may be included.
- distribution of this electroconductive material can be selected suitably.
- various organic solvents such as water, hydrocarbon, alcohol, ketone, ether and ester can be used.
- the ink contains a binder component such as a resin, an antioxidant, various catalysts for promoting film formation, various interfacial energy regulators, leveling agents, mold release accelerators, and the like as necessary.
- a binder component such as a resin, an antioxidant, various catalysts for promoting film formation, various interfacial energy regulators, leveling agents, mold release accelerators, and the like as necessary.
- inks in particular, inks in which nano silver particles are dispersed in a solvent and mixed with a release agent such as low molecular weight silicone and an interfacial energy adjusting agent such as a fluorosurfactant are suitable for the letterpress offset method. It can be preferably used because of its high patterning properties and high conductivity at low temperature firing. Conversion from the ink film layer to the source and drain electrodes that constitute the organic transistor is a method that is optimal for ink characteristics and electronic components, such as drying at room temperature, heat treatment, and ultraviolet light, electron beam irradiation, etc. Can be implemented.
- a test element having a bottom gate bottom contact (BGBC) structure shown in FIG. 1 was prepared, and the characteristics of the organic transistor of the present invention were evaluated.
- the field effect mobility and ON / OFF value were calculated from the measured values of Id-Vg and Id-Vd.
- Example 1 The transistor characteristic measuring element having the bottom gate bottom contact (BGBC) structure shown in FIG. 1 was prepared by the following procedure.
- Source and drain electrode patterns made of gold with a channel length of 50 ⁇ m and a channel width of 2 mm were formed on the previously formed gate insulating layer by vacuum deposition using a metal mask.
- the fabricated device was subjected to heat treatment in a glow box at 150 ° C.
- Example 2 An organic transistor element was prepared in the same manner as in Example 1 except that the polymer obtained in Synthesis Example 2 was used as the fluorosurfactant added to the organic semiconductor (P3HT) solution. The obtained transistor characteristics are shown in Table 1.
- Example 3 A transistor characteristic measuring element having a bottom gate bottom contact (BGBC) structure shown in FIG. 1 was prepared.
- gate electrode A polycarbonate film with a hard cord having a thickness of about 125 ⁇ m is cut into a predetermined size, and a conductive ink in which nano-particle silver is uniformly dispersed is applied uniformly on the film by spin coating, Firing was performed at 180 ° C. for 30 minutes in a clean oven.
- Formation of an insulating layer using an insulating ink containing polyvinylphenol and polymethacrylate copolymer as an insulating resin component, it is applied on a Cr electrode by a spin coating method, and heat-treated in a clean oven at 140 ° C.
- the organic semiconductor ink prepared is formed on a smooth polydimethylsiloxane (PDMS) rubber using a bar coater
- the insulating layer with the source and drain electrodes prepared above is pressed against the coated film
- the semiconductor coating film was transferred onto the insulating layer, and a P3HT semiconductor layer having a thickness of about 70 nm was formed on the insulating layer.
- the fabricated element was heat-treated in a glow box at 150 ° C. for about 5 minutes, and Id-Vg and Id-Vd characteristics were measured using a semiconductor parameter measuring device (Keithley 4200) to transfer the field effect.
- the degree and ON / OFF were determined by a known method.
- the obtained transistor characteristics are shown in Table 1.
- Example 4 Substrate, gate electrode, insulating layer: A silicon wafer with 300 nm thick thermally oxidized silicon was cut into a predetermined size, and the surface of the thermally oxidized silicon was modified with octyltrichlorosilane (OTS-8). As the gate electrode, a silicon surface obtained by scraping silicon oxide with a diamond pen was used.
- OTS-8 octyltrichlorosilane
- OTS-8 octyltrichlorosilane
- the fabricated device was heat-treated in a glow box at 150 ° C. for about 5 minutes, and measured for Id-Vg and Id-Vd characteristics using a semiconductor parameter measuring device (Keithley 4200). The ON / OFF ratio was determined by a known method. The obtained transistor characteristics are shown in Table 1.
- Example 1 A transistor element was prepared in the same manner as in Example 1 except that no fluorine-based surfactant was added to the organic semiconductor ink, and its characteristics were measured. The obtained characteristics are shown in Table 1.
- Example 4 (Comparative Example 2) In Example 4, the P3HT xylene solution to which no fluorosurfactant was added was repelled on the silicon oxide treated with OTS-8 during spin coating, and a coating film could not be formed.
- the organic semiconductor element of the present invention can be suitably applied to the production of electronic elements used for liquid crystal displays, electronic paper, EL display devices, RF-ID tags, and the like.
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Abstract
Description
(ここで、R1はH、CH3、Cl、FまたはCNであり、Xは2価の連結基で具体的には、-(CH2)n-、-CH2CH(OH)(CH2)n-、-(CH2)nN(R2)SO2-、-(CH2)nN(R2)CO-(但し、nは1~10の整数であり、R2はHまたは炭素数1~18のアルキル基である。)、-CH(CH3)-、-CH(CH2CH3)-、-C(CH3)2-、-CH(CF3)-、-C(CF3)2-、CH2CFH-等であり、aは0または1、mは1~20の整数である。)
A-1 :CH2=CHCOOCH2CH2C8F17
A-2 :CH2=C(CH3)COOCH2CH2C8F17
A-3 :CH2=CHCOOCH2CH2C12F25
A-4 :CH2=CHCOOCH2CH2C6F13
A-5 :CH2=CHCOOCH2CH2C4F9
A-6 :CH2=CFCOOCH2CH2C6F13
A-7 :CH2=CHCOOCH2CF3
A-8 :CH2=C(CH3)COOCH2CF(CF3)2
A-9 :CH2=C(CH3)COOCH2CFHCF3
A-10 :CH2=CHCOOCH2(CF2)6H
A-11 :CH2=CHCOOCH2CH(OH)CH2C8F17
A-12 :CH2=CHCOOCH2CH2N(C3H7)SO2C8F17
A-13 :CH2=CHCOOCH2CH2N(C2H5)COC7F15
撹拌装置、コンデンサー、温度計、滴下ロートを備えたガラスフラスコに、フッ素化(メタ)アクリレートとして(A-1)を27重量部、非フッ素(メタ)アクリレートとして、ポリオキシプロピレンモノメタクリレート(平均重合度;5)を21.6重量部、3-メタクリロキシプロピルトリス(トリメチルシロキシ)シランを5.4重量部、重合溶媒としてメチルエチルケトン(MEK)を66.1重量部、および重合開始剤としてジメチル2,2‘-アゾビス(2-メチルプロピオネート)を0.54重量部、秤量し仕込む。また、(A-1)を63重量部、ポリオキシプロピレンモノメタクリレート(平均重合度;5)を50.4重量部、3-メタクリロキシプロピルトリス(トリメチルシロキシ)シランを12.6重量部、MEKを124.2重量部、ジメチル2,2‘-アゾビス(2-メチルプロピオネート)を1.26重量部、別途予め混合した溶液(滴下溶液)を調製する。ガラスフラスコ内に窒素気流を通じ、80℃まで昇温した後、滴下液を2時間かけて滴下し、80℃にて3時間ホールドする。その後、ジメチル2,2‘-アゾビス(2-メチルプロピオネート)0.9重量部をMEK9重量部に溶解させた溶液を加えて,さらに7時間ホールドし、フッ素化(メタ)アクリル重合体(1)を得た。得られた重合体(1)のゲルパーミエーションクロマトグラフィー(GPC)によるポリスチレン換算の重量平均分子量はMw=185,000であった。
ガラス製重合管に、フッ素化(メタ)アクリレートとして(A-1)を9.3g、非フッ素(メタ)アクリレートとして4-(6-アクリロイルオキシヘキシルオキシ)フェニルベンゼンを18g、重合溶媒としてトルエン220mL、重合開始剤として2,2’アゾビス(2,4-ジメチルバレロニトリルと(A-1)0.55gを秤量し仕込む。この溶液に窒素気流を通じ酸素を取り除いた後、60℃で24時間反応させた。反応終了後、反応液を濃縮し、濃縮液を1Lのメタノール中に滴下した。沈殿した固体をメタノールで良く洗浄し、フッ素化(メタ)アクリル重合体(2)を得た。得られた重合体(2)のGPCによるポリスチレン換算の重量平均分子量はMw=47,000であった。
以下の手順で、図1に示すボトムゲートボトムコンタクト(BGBC)構造を有するトランジスタ特性測定用素子を作成した。
(1)ゲート電極の形成:無アルカリガラス上にスパッタ方式によりCr膜を形成しこれを所望のパターンにエッチングすることによりゲート電極を形成した。
(2)ゲート絶縁層の形成:ポリビニルフェノールとポリメタクリレート共重合体を絶縁樹脂成分とする絶縁インキを用い、スピンコート法によりCr電極上に塗布し、クリーンオーブン中で140℃約1時間熱処理し膜厚約1μmの有機ゲート絶縁層を形成した。
(3)ソース、ドレイン電極の形成:先に形成したゲート絶縁層上にメタルマスクを用いて真空蒸着法により金からなるチャネル長50μm、チャネル幅2mmのソース、ドレイン電極パターンを形成した。
(4)有機半導体層の形成:有機半導体P3HTのキシレン0.5重量%溶液にフッ素系界面活性剤(商品名メガファック MCF350SF(フッ素化(メタ)アクリル重合体,重量平均分子量Mw=53,000):DIC社製品)を1wt%添加し、スピンコート法により、上記ゲート絶縁層上にP3HT薄膜を形成した。
(5)作成した素子はグローボックス中で150℃、約5分の熱処理を行った後にId-Vg、Id-Vd特性を半導体パラメター測定装置(ケースレー社4200)を用いて測定し、これより電界効果移動度及びON/OFF比を周知の方法より求めた。電界効果移動度の単位は、cm2/Vsである。結果を表1に示す。
有機半導体(P3HT)溶液に添加するフッ素系界面活性剤として合成例2で得た重合体を使用した以外実施例1と同様に有機トランジスタ素子を作成した。得られたトランジスタ特性を表1に示す。
図1に示すボトムゲートボトムコンタクト(BGBC)構造を有するトランジスタ特性測定用素子を作成した。
(1)ゲート電極の形成:厚さ約125μmのハードコード付ポリカーボネートフィルムを所定の大きさにカットし、ナノ粒子銀を均一に分散させた導電インキをスピンコートによりフィルム上に均一に塗布し、クリーンオーブン中で180℃、30分焼成した。
(2)絶縁層の形成:ポリビニルフェノールとポリメタクリレート共重合体を絶縁樹脂成分とする絶縁インキを用い、スピンコート法によりCr電極上に塗布し、クリーンオーブン中で140℃約1時間熱処理し膜厚約0.8μmの有機ゲート絶縁層を形成した。
(3)ソース、ドレイン電極の形成:反転印刷用の導電性インキを用い凸版反転印刷により、先に形成したゲート絶縁層上にチャネル長50μm、チャネル幅4mmのソース、ドレイン電極パターンを形成し、クリーンオーブン中で180℃、30分焼成し、銀電極を形成した。
(4)有機半導体層の形成:
P3HTのキシレン0.5重量%溶液に、フッ素系界面活性剤として合成例1で得た重合体(1)と合成例2で得た重合体(2)の40/60wt%混合体を1%添加し有機半導体インキを調製した。調製した有機半導体インキを、バーコーターを用いて平滑なポリジメチルシロキサン(PDMS)ゴム上に塗膜を形成した後、該塗膜に先に調製したソース、ドレイン電極付の絶縁層を押し当て、該半導体塗膜を該絶縁層上に転写し、膜厚約70nmのP3HT半導体層を絶縁層上に形成した。
(5)作成した素子はグローボックス中で150℃、約5分の熱処理を行い、Id-Vg、Id-Vd特性を、半導体パラメター測定装置(ケースレー社4200)を用いて測定し、電界効果移動度及びON/OFFを周知の方法より求めた。得られたトランジスタ特性を表1に示す。
(1)基板、ゲート電極、絶縁層:厚さ300nm熱酸化シリコン付きシリコンウエハーより所定の大きさに切り出し、熱酸化シリコン表面をオクチルトリクロロシラン(OTS-8)で表面修飾した。ゲート電極は酸化シリコンをダイヤモンドペンで削りだしたシリコン面を使用した。
(2)有機半導体層の形成:P3HTのキシレン0.5重量%溶液に、フッ素系界面活性剤として合成例1で得た重合体(1)を3%添加し有機半導体インキを調製した。OTS-8で表面処理した熱酸化シリコン基板上にスピンコート法により厚さ約70nmの有機半導体層を形成した。
(3)作成した素子はグローボックス中で150℃、約5分の熱処理を行い、Id-Vg、Id-Vd特性を半導体パラメター測定装置(ケースレー社4200)を用いて測定し、電界効果移動度及びON/OFF比を周知の方法より求めた。得られたトランジスタ特性を表1に示す。
有機半導体インキにフッ素系界面活性剤を添加しない以外実施例1と同様の方法でトランジスタ素子を作成し、その特性を測定した。得られた特性を表1に示す。
実施例4においてフッ素系界面活性剤を添加しないP3HTのキシレン溶液はスピンコート塗布時にOTS-8処理した酸化シリコン上で液がハジキ、塗膜が形成できなかった。
2.ゲート電極
3.絶縁膜
4.有機半導体層
5.ソース、ドレイン電極
Claims (4)
- (a)基板上に、(b)ゲート電極、(c)絶縁層、(d)該絶縁層に接する有機半導体層に形成されたチャネル形成領域及び(e)ソース/ドレイン電極を有する有機トランジスタであって、該有機半導体層にフッ素系界面活性剤を含有することを特徴とする有機トランジスタ。
- 有機半導体が結晶性を有する有機半導体材料である請求項1に記載の有機トランジスタ。
- フッ素系界面活性剤がフッ素化(メタ)アクリル重合体である請求項1又は2に記載の有機トランジスタ。
- (a)基板上に、(b)ゲート電極、(c)絶縁層、(d)該絶縁層に接する有機半導体層に形成されたチャネル形成領域及び(e)ソース/ドレイン電極を有する有機トランジスタの製造方法であって、該絶縁層上に、フッ素系界面活性剤を含有する有機半導体溶液の印刷又は塗布により(d)有機半導体層を形成する工程、又は、(d)フッ素系界面活性剤を含有する有機半導体層上に、印刷又は塗布により絶縁層を形成する工程を有することを特徴とする有機トランジスタの製造方法。
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US13/055,303 US9166182B2 (en) | 2008-07-22 | 2009-06-29 | Organic transistor and method for producing the same |
CN2009801289919A CN102105987B (zh) | 2008-07-22 | 2009-06-29 | 有机晶体管及其制造方法 |
EP09800306.4A EP2312637A4 (en) | 2008-07-22 | 2009-06-29 | ORGANIC TRANSISTOR AND METHOD FOR MANUFACTURING THE SAME |
KR1020107024250A KR101238356B1 (ko) | 2008-07-22 | 2009-06-29 | 유기 트랜지스터 및 그 제조 방법 |
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WO2014189116A1 (ja) * | 2013-05-23 | 2014-11-27 | 富士フイルム株式会社 | 有機半導体組成物および有機薄膜トランジスタならびに電子ペーパーおよびディスプレイデバイス |
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JP2017054876A (ja) * | 2015-09-08 | 2017-03-16 | 富士フイルム株式会社 | 有機半導体膜形成用組成物、有機半導体膜およびその製造方法、並びに有機半導体素子 |
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JPWO2010010791A1 (ja) | 2012-01-05 |
CN102105987A (zh) | 2011-06-22 |
JP4582430B2 (ja) | 2010-11-17 |
EP2312637A4 (en) | 2013-08-07 |
KR20100139107A (ko) | 2010-12-31 |
CN102105987B (zh) | 2013-04-03 |
KR101238356B1 (ko) | 2013-02-28 |
US9166182B2 (en) | 2015-10-20 |
US20110121281A1 (en) | 2011-05-26 |
EP2312637A1 (en) | 2011-04-20 |
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