WO2015115234A1 - 有機薄膜トランジスタの製造方法およびその製造方法により製造された有機薄膜トランジスタ - Google Patents

有機薄膜トランジスタの製造方法およびその製造方法により製造された有機薄膜トランジスタ Download PDF

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WO2015115234A1
WO2015115234A1 PCT/JP2015/051256 JP2015051256W WO2015115234A1 WO 2015115234 A1 WO2015115234 A1 WO 2015115234A1 JP 2015051256 W JP2015051256 W JP 2015051256W WO 2015115234 A1 WO2015115234 A1 WO 2015115234A1
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thin film
film transistor
organic thin
organic
group
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PCT/JP2015/051256
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English (en)
French (fr)
Japanese (ja)
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佑一 早田
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富士フイルム株式会社
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    • 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]
    • H10K10/468—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics
    • H10K10/471—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics the gate dielectric comprising only organic materials
    • 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
    • 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]
    • 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
    • H10K10/80—Constructional details
    • H10K10/82—Electrodes
    • H10K10/84—Ohmic electrodes, e.g. source or drain electrodes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/621—Providing a shape to conductive layers, e.g. patterning or selective deposition

Definitions

  • the present invention relates to a method for producing an organic thin film transistor and an organic thin film transistor produced by the method.
  • organic devices such as FETs (field effect transistors), RFIDs (RF tags), and memories that are used in liquid crystal displays and organic EL displays
  • organic TFT organic thin film transistor
  • organic semiconductor layer An organic thin film transistor (organic TFT) having a semiconductor film (organic semiconductor layer) is used.
  • a metal fine particle layer (metal fine particles having an average particle size of 50 nm or less is obtained by patterning a metal fine particle dispersion such as gold, silver, copper, etc. by a printing method on a source electrode and a drain electrode.
  • Patent Document 1 describes a method of forming an electrode by thermally fusing metal fine particles by forming a layer substantially consisting of a group) and then performing heat treatment.
  • the organic thin film transistor is required to further improve the operation speed and reliability.
  • the method for producing an organic thin film transistor described in Patent Document 1 it was found that there was room for improvement in operating speed (carrier mobility) and reliability (migration resistance, electrode adhesion). It was done.
  • the migration resistance is intended to prevent the occurrence of metal ion migration between the source electrode and the drain electrode
  • the electrode adhesion is a gate insulating film layer adjacent to the electrode (source electrode and / or drain electrode). Intended to adhere to.
  • this invention makes it a subject to provide the organic thin-film transistor manufactured by the manufacturing method of the organic thin-film transistor for manufacturing the organic thin-film transistor excellent in carrier mobility, migration resistance, and electrode adhesiveness, and its manufacturing method To do.
  • the present inventor can obtain a desired effect by forming a source electrode and / or a drain electrode using a predetermined composition for forming a conductive film.
  • the present invention was completed. That is, the present inventors have found that the above problem can be solved by the following configuration.
  • a gate electrode, a gate insulating film layer containing an organic insulating material, a source electrode, a drain electrode, and an organic semiconductor layer are provided, the gate insulating film layer and the source electrode, and the gate insulating film layer and the drain electrode.
  • the manufacturing method of an organic thin-film transistor including the process of forming at least one among a source electrode and a drain electrode by performing heat baking or light baking with respect to the coating film formed using the composition for electrically conductive film formation.
  • the organic insulating material includes an organic insulating material having a siloxane group or a perfluoro group.
  • the heating and baking in the step of forming at least one of the source electrode and the drain electrode is performed by heat treatment at a temperature equal to or higher than the glass transition temperature of the organic insulating material in the gate insulating film layer.
  • For producing an organic thin film transistor for producing an organic thin film transistor.
  • At least one metal particle or salt containing at least one metal element selected from the group consisting of Group 8 to 11 elements of the Periodic Table is selected from the group consisting of Group 10 elements of the Periodic Table
  • an organic thin film transistor manufacturing method and an organic thin film transistor manufactured by the manufacturing method for manufacturing an organic thin film transistor excellent in carrier mobility, migration resistance, and electrode adhesion.
  • FIG. 1 is a cross-sectional view of one embodiment of a bottom gate-bottom contact type organic thin film transistor.
  • FIG. 2 is a cross-sectional view of another embodiment of a bottom gate-bottom contact type organic thin film transistor.
  • FIG. 3 is a cross-sectional view of one embodiment of a top gate-top contact type organic thin film transistor.
  • FIG. 4 is a cross-sectional view of another embodiment of a top gate-top contact type organic thin film transistor.
  • FIG. 5 is a plan view of the metal mask used in the example.
  • a numerical range represented by using “to” means a range including numerical values described before and after “to” as a lower limit value and an upper limit value.
  • a source electrode is formed using a conductive film forming composition containing a predetermined component. And / or the point which produces the drain electrode is mentioned.
  • a gate insulating film layer containing an organic insulating material is in contact with a source electrode and a drain electrode. Therefore, when a source electrode and / or a drain electrode are produced by performing heat baking or light baking using a conductive film forming composition described later, the organic insulating material of the gate insulating film layer and the conductive film forming composition are derived. By the interaction with this component, the adhesion of the formed electrode to the gate insulating film layer is improved. In addition, in the case of light baking, it is estimated that adhesiveness improves according to the heat
  • FIG. 1 shows a cross-sectional view of one embodiment of a bottom gate-bottom contact type organic thin film transistor.
  • the organic thin film transistor 10 includes a support 12, a gate electrode 14 disposed on the support 12, a gate insulating film layer 16 in contact with the gate electrode 14, and a gate of the gate insulating film layer 16.
  • the source electrode 18 and the drain electrode 20 disposed so as to be in contact with the surface opposite to the electrode 14 side, the source electrode 18, the drain electrode 20, and the gate in the region sandwiched between the source electrode 18 and the drain electrode 20.
  • the organic semiconductor layer 22 is disposed so as to cover the insulating film layer 16.
  • the gate insulating film layer 16 includes an organic insulating material.
  • the production method of the present invention is a step of forming at least one of the source electrode 18 and the drain electrode 20 by subjecting a coating film formed using the composition for forming a conductive film, which will be described later, to heat baking or light baking.
  • source / drain formation step at least, and the formation method of other members (gate electrode 14, gate insulating film layer 16, organic semiconductor layer 22) is not particularly limited, Step of forming gate electrode 14 (gate forming step), step of forming gate insulating film layer 16 (insulating film layer forming step), source / drain forming step, and step of forming organic semiconductor layer 22 (organic semiconductor) It is preferable to carry out the forming step in this order.
  • the procedure which has the said process is explained in full detail as one of the suitable aspects of the manufacturing method of the organic thin-film transistor 10 shown in FIG.
  • This step is a step of forming a gate electrode on the support.
  • the type of the support is not particularly limited, and is mainly composed of glass or a flexible resin sheet.
  • a plastic film can be used as the sheet.
  • the plastic film include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyether ether ketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC), cellulose triacetate (TAC), and cellulose acetate propionate.
  • PET polyethylene terephthalate
  • PEN polyethylene naphthalate
  • PEN polyether ether ketone
  • polyphenylene sulfide polyarylate
  • polyimide polyimide
  • PC polycarbonate
  • TAC cellulose triacetate
  • CAP cellulose acetate propionate
  • CAP cellulose triacetate
  • the material constituting the gate electrode is not particularly limited as long as it is a conductive material.
  • a conductive material For example, gold (Au), silver, aluminum (Al), copper, chromium, nickel, cobalt, titanium, platinum, magnesium, calcium, barium, Metals such as sodium; conductive oxides such as InO 2 , SnO 2 , ITO; conductive polymers such as polyaniline, polypyrrole, polythiophene, polyacetylene, polydiacetylene; semiconductors such as silicon, germanium, gallium arsenide; fullerene, carbon Examples thereof include carbon materials such as nanotubes and graphite. Especially, it is preferable that it is a metal, and it is more preferable that they are silver and aluminum.
  • the method for forming the gate electrode is not particularly limited.
  • a method of etching on a metal foil using a resist such as thermal transfer or ink jet.
  • a conductive polymer solution or dispersion, or a conductive fine particle dispersion may be directly patterned by ink jetting, or may be formed from a coating film by lithography or laser ablation.
  • a method of patterning an ink containing a conductive polymer or conductive fine particles, a conductive paste, or the like by a printing method such as relief printing, intaglio printing, planographic printing, or screen printing can also be used.
  • the thickness of the gate electrode is not particularly limited, but is preferably 20 to 200 nm.
  • This step is a step of forming a gate insulating film layer in contact with the gate electrode on the support.
  • the gate insulating film layer is usually disposed so as to cover the gate electrode.
  • the gate insulating film layer includes an organic insulating material.
  • an organic insulating material in the gate insulating film layer By including an organic insulating material in the gate insulating film layer, excellent adhesion between the source electrode and / or the drain electrode is achieved at the time of heat baking or light baking in the source / drain formation process described later. .
  • the content of the organic insulating material in the gate insulating film layer is not particularly limited, but is preferably included as a main component.
  • the main component means that the content of the organic insulating material is 75% by mass or more with respect to the total mass of the gate insulating film layer, and the source electrode and / or drain electrode, the gate insulating film layer, 90 mass% or more is preferable at the point which is more excellent in adhesiveness, and 100 mass% is more preferable.
  • the organic insulating material is not particularly limited as long as it is an organic substance (organic compound) exhibiting insulating properties.
  • an insulating resin is preferable, and more specifically, polyimide, polyamide, polyester, polyacrylate, photo-curing resin of photo radical polymerization type or photo cationic polymerization type, copolymer containing acrylonitrile component, polyvinyl phenol, polyvinyl Alcohol, novolac resin, epoxy resin, cyanoethyl pullulan, silicon polymer, fluorine polymer, or the like can be used.
  • the organic insulating material having a siloxane group or a perfluoro group a siloxane group-containing polymer or a perfluoro group-containing polymer is preferably used.
  • the siloxane group-containing polymer include polydimethylsiloxane and polysilsesquioxane.
  • Examples of the perfluoro group-containing polymer include Teflon (R) (Mitsui / DuPont Fluorochemicals), Cytop (R ) (Manufactured by Asahi Glass Co., Ltd.), and amorphous fluororesins such as NEOFLON TM (manufactured by Daikin).
  • the siloxane group means a group represented by Si—O
  • the perfluoro group means a group in which all hydrogen atoms are substituted with fluorine atoms.
  • a method for forming the gate insulating film layer is not particularly limited.
  • the gate insulating film layer is formed by applying a composition for forming a gate insulating film layer containing the organic insulating material onto a support on which a gate electrode is formed. And a method of forming a gate insulating film layer by vapor deposition or sputtering of the organic insulating material.
  • the composition for forming a gate insulating film layer may contain a solvent (water or an organic solvent) as necessary.
  • the composition for forming a gate insulating film layer may contain a crosslinking component.
  • a crosslinked structure can be introduced into the gate insulating film layer by adding a crosslinking component such as melamine to an organic insulating material containing a hydroxy group.
  • the method for applying the gate insulating film layer forming composition is not particularly limited, and is applied by spray coating, spin coating, blade coating, dip coating, casting, roll coating, bar coating, die coating, or the like.
  • a wet process such as a method using a patterning method or a method using a patterning method such as inkjet is preferable.
  • a gate insulating film layer-forming composition is applied to form a gate insulating film layer, it may be heated (baked) after application for the purpose of solvent removal, crosslinking and the like.
  • the thickness of the gate insulating film layer is not particularly limited, but is preferably 50 nm to 3 ⁇ m, and more preferably 200 nm to 1 ⁇ m.
  • This step is a step of forming at least one of a source electrode and a drain electrode by subjecting a coating film formed using a predetermined conductive film forming composition to heat baking or light baking. More specifically, the conductive film forming composition is applied onto the gate insulating film layer in the laminate including the support, the gate electrode, and the gate insulating film layer to form a coating film, Heat baking or light baking is performed.
  • the conductive film forming composition is applied onto the gate insulating film layer in the laminate including the support, the gate electrode, and the gate insulating film layer to form a coating film, Heat baking or light baking is performed.
  • the composition for electrically conductive film formation used at this process is explained in full detail first.
  • composition for forming a conductive film is at least one selected from the group consisting of copper oxide particles having an average primary particle size of 100 nm or less and Group 8 to 11 elements of the periodic table Metal particles or salts containing the above metal elements and an alcohol compound.
  • a composition is at least one selected from the group consisting of copper oxide particles having an average primary particle size of 100 nm or less and Group 8 to 11 elements of the periodic table Metal particles or salts containing the above metal elements and an alcohol compound.
  • Copper oxide particles having an average primary particle diameter of 100 nm or less contains copper oxide particles having an average primary particle diameter of 100 nm or less (hereinafter sometimes referred to as “copper oxide particles (A)”).
  • copper oxide particles (A) the copper oxide is reduced to metallic copper by a sintering process described later, and constitutes a metal conductor in the electrode film.
  • copper oxide copper (I) oxide, copper (II) oxide or a mixture thereof is preferable, and copper (II) oxide is more preferable because it is available at low cost and is more stable in the air.
  • the “copper oxide” in the present invention is a compound that does not substantially contain copper that has not been oxidized. Specifically, in crystal analysis by X-ray diffraction, a peak derived from copper oxide is detected, and metallic copper. It refers to a compound for which no peak is detected.
  • substantially free of copper means that the copper content is 1% by mass or less based on the copper oxide particles.
  • the average primary particle diameter of the copper oxide particles (A) is not particularly limited as long as it is 100 nm or less, but is preferably 1 to 80 nm, and more preferably 10 to 50 nm. As the average primary particle size is smaller, copper oxide is more easily reduced, and a conductive film having high conductivity can be produced even when sintered at a lower sintering temperature. When the average primary particle size is 10 nm or more, better dispersion stability can be obtained.
  • the average primary particle diameter of the copper oxide particles (A) is the horizontal ferret diameter and vertical ferret diameter of 100 particles randomly selected from a scanning electron microscope (hereinafter sometimes referred to as “SEM”) image. The diameter is measured, and the larger measured value among them is calculated as the primary particle diameter of the particles by arithmetic averaging. When the horizontal ferret diameter and the vertical ferret diameter are the same, any value may be used.
  • the conductive film forming composition is a metal particle or salt containing at least one metal element selected from the group consisting of Group 8 to 11 elements of the periodic table (hereinafter referred to as “metal particle or salt (B)”) Is included.)
  • the Group 8-11 elements are iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co) in which stable isotopes exist among Groups 8-11 of the IUPAC periodic table. ), Rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), and gold (Au).
  • palladium, rhodium, platinum or a combination of two or more of these elements is preferable, palladium, platinum or a combination thereof is more preferable, and palladium is more preferable.
  • metal ions contained in the metal particles containing the metal element or the salt containing the metal element The simple substance of the metal produced by reduction of the copper promotes the reduction of the copper oxide particles (A) and promotes the fusion of the copper particles produced by reducing the copper oxide of the copper oxide particles (A).
  • a conductive film (electrode) having conductivity can be manufactured.
  • Metal particles containing at least one metal element selected from the group consisting of Group 8 to 11 elements of the periodic table are iron, ruthenium, osmium, Metal particles containing one or more elements selected from cobalt, rhodium, iridium, nickel, palladium, platinum, copper, silver and gold.
  • the metal particles (B1) are metal particles containing a Group 8-11 element, preferably 85% by mass or more, more preferably 90% by mass or more, and further preferably 95% by mass or more.
  • the surfaces of the metal particles (B1) may be coated with a coating agent such as sodium polyacrylate or a protective colloid in order to prevent oxidation, aggregation and the like.
  • the average primary particle diameter of the metal particles (B1) is not particularly limited, but is preferably 1 to 50 nm, more preferably 1 to 10 nm, and further preferably 1 to 5 nm.
  • the average primary particle diameter of the metal particles (B1) is determined by measuring the horizontal ferret diameter and the vertical ferret diameter of 100 particles randomly selected from the SEM image, and taking the larger measured value of them.
  • the primary particle diameter of the particles is calculated by arithmetic averaging. When the horizontal ferret diameter and the vertical ferret diameter are the same, any value may be used.
  • metal salt (B2) The salt of at least one metal element selected from the group consisting of Group 8 to 11 elements of the periodic table (hereinafter sometimes referred to as “metal salt (B2)”) is iron, ruthenium, osmium, cobalt, It is a salt (including a complex) containing one or more elements selected from rhodium, iridium, nickel, palladium, platinum, copper, silver and gold.
  • metal salt (B2) examples include palladium chloride (II), halide salts such as chloride such as potassium tetrachloroparadate; nitrates such as palladium nitrate; sulfates; carbonates; palladium acetate (II) Carboxylates such as acetate; ammine complexes; tetraammine nitrates such as tetraamminepalladium (II) nitrate and tetraammineplatinum (II) nitrate; metal carbonyl complexes such as triruthenium dodecacarbonyl (dodecacarbonyltriruthenium); di (acetyl Acetylacetonate salts such as acetonato) palladium; phosphine complexes such as tetrakis (triphenylphosphine) palladium, tetrakis (triphenylphosphine) platinum, dichloro [bis (1,
  • composition for electrically conductive film formation used for the manufacturing method of the organic thin-film transistor of this invention contains an alcohol compound (Hereinafter, it may be mentioned "alcohol (C).”).
  • Alcohol (C) acts as a reducing agent for reducing the copper oxide of the copper oxide particles (A) during the heat treatment.
  • Alcohol (C) is not particularly limited as long as it is a compound having one or more alcoholic hydroxy groups in one molecule.
  • alcohol (C) examples include methanol, ethanol, propanol, 2-propanol, allyl alcohol, butanol, 2-butanol, pentanol, 2-pentanol, 3-pentanol, cyclopentanol, Hexanol, 2-hexanol, 3-hexanol, cyclohexanol, heptanol, 2-heptanol, 3-heptanol, 4-heptanol, cycloheptanol, octanol, 2-octanol, 3-octanol, 4-octanol, cyclooctanol, nonanol, 2-nonanol, 3,5,5-trimethyl-1-hexanol, 3-methyl-3-octanol, 3-ethyl-2,2-dimethyl-3-pentanol, 2,6-dimethyl-4-heptanol, decanol ,
  • the alcohol (C) preferably contains a divalent or trivalent alcohol, and more preferably contains a trivalent alcohol in terms of better migration resistance between electrodes and electrode adhesion.
  • a divalent or trivalent alcohol preferably contains a trivalent alcohol in terms of better migration resistance between electrodes and electrode adhesion.
  • trimethylolpropane is particularly preferable.
  • the composition for forming a conductive film may further contain a solvent (however, alcohol (C) is not included).
  • the solvent is not particularly limited as long as it can disperse or dissolve copper oxide particles (A), metal particles or salt (B) and alcohol (C) and does not react with them, but alcohol. Is not included.
  • the solvent include one selected from water, ethers, esters, hydrocarbons, and aromatic hydrocarbons, or a mixture of two or more compatible.
  • water an alkyl ether derived from a water-soluble alcohol, an alkyl ester derived from a water-soluble alcohol, or a mixture thereof is preferably used because of excellent compatibility with the alcohol (C).
  • water what has the purity of the level more than ion-exchange water, for example, reverse osmosis filtered water (RO water), milli Q water, distilled water, etc. are preferable.
  • RO water reverse osmosis filtered water
  • milli Q water milli Q water
  • distilled water etc.
  • the main solvent is a solvent having the highest content in the solvent.
  • the conductive film-forming composition may contain other components in addition to the copper oxide particles (A), metal particles or salt (B), alcohol (C), and solvent.
  • the composition for forming a conductive film may contain a surfactant.
  • the surfactant plays a role of improving the dispersibility of the copper oxide particles.
  • the type of the surfactant is not particularly limited, and examples thereof include an anionic surfactant, a cationic surfactant, a nonionic surfactant, a fluorine surfactant, and an amphoteric surfactant. These surfactants can be used alone or in combination of two or more.
  • the composition for forming a conductive film can be produced by mixing copper oxide particles (A), metal particles or salt (B), alcohol (C), and solvent (D), if desired.
  • the mass ratio (B / A) between the copper oxide particles (A) and the metal particles or the salt (B) in the conductive film forming composition is not particularly limited, but the source electrode and / or drain electrode and the gate insulating film layer are not limited. 0.005 in terms of better adhesion to the electrode, better migration resistance between the electrodes, or better mobility of the organic thin film transistor (hereinafter also referred to simply as “the better effect of the present invention”). To 0.1 is preferable, and 0.01 to 0.05 is more preferable.
  • the mass ratio (C / A) between the copper oxide particles (A) and the alcohol (C) in the composition for forming a conductive film is not particularly limited, but is 0.1 to 10 in that the effect of the present invention is more excellent. Is preferable, and 0.3 to 6.0 is more preferable.
  • the mass ratio (D / A) between the copper oxide particles (A) and the solvent (D) in the composition for forming a conductive film is not particularly limited, but is 0.2 to 5 in that the effect of the present invention is more excellent. 0.0 is preferable, and 0.3 to 3.0 is more preferable.
  • the source electrode and the drain electrode can be formed by subjecting a coating film formed using the above-described conductive film forming composition to heat baking or light baking. More specifically, the composition for forming a conductive film described above is applied on the gate insulating film layer (applied in a pattern), and the obtained coating film is subjected to heat baking or light baking to obtain a source. An electrode and a drain electrode are formed.
  • the method for applying the conductive film forming composition is not particularly limited, and a known method is employed.
  • the composition for forming a conductive film can be patterned at a predetermined position by a printing method such as letterpress printing, screen printing, planographic printing, intaglio printing, stencil printing, or ink jet printing.
  • a printing method such as letterpress printing, screen printing, planographic printing, intaglio printing, stencil printing, or ink jet printing.
  • the conductive film forming composition is applied, it is applied in a pattern so as to have a predetermined shape of the source electrode and the drain electrode.
  • the thickness of the coating film formed is adjusted so that it may become the suitable thickness of the source electrode and drain electrode which are mentioned later.
  • the ink jet method is a method of patterning by discharging a conductive film forming composition from an ink jet head.
  • an on-demand type such as a piezo method or a bubble jet (R) method
  • Patterning can be performed by a known method such as a continuous jet type ink jet method such as an electrostatic suction method.
  • a drying process as needed. By applying the drying treatment, the solvent in the coating film can be removed.
  • a conductive film is formed by subjecting the obtained coating film (layer of the composition for forming a conductive film) to a sintering process such as heat baking or light baking, and the source electrode and the drain electrode are formed. .
  • the heating temperature is preferably 150 to 220 ° C., more preferably 160 to 200 ° C.
  • the heating time is preferably 5 to 120 minutes, more preferably 5 to 30 minutes.
  • the heating means is not particularly limited, and known heating means such as an oven and a hot plate can be used.
  • the light irradiation treatment at the time of photo-firing makes it possible to reduce and sinter to metallic copper by irradiating light on the part to which the coating film is applied at room temperature for a short time.
  • the base material (gate insulating film layer) is not deteriorated by heating for a long time, and the adhesion of the conductive film to the base material becomes better.
  • the light source used in the light irradiation treatment is not particularly limited, and examples thereof include a mercury lamp, a metal halide lamp, a xenon lamp, a chemical lamp, and a carbon arc lamp.
  • Examples of radiation include electron beams, X-rays, ion beams, and far infrared rays.
  • g-line, i-line, deep-UV light, and high-density energy beam (laser beam) are used.
  • Specific examples of preferred embodiments include scanning exposure with an infrared laser, high-illuminance flash exposure such as a xenon discharge lamp, and infrared lamp exposure.
  • the light irradiation is preferably light irradiation with a flash lamp, and more preferably pulsed light irradiation with a flash lamp. Irradiation with high-energy pulsed light can concentrate and heat the surface of the portion to which the coating film has been applied in a very short time, so that the influence of heat on the substrate can be extremely reduced.
  • the irradiation energy of the pulse light is preferably 1 ⁇ 100J / cm 2, more preferably 1 ⁇ 30J / cm 2, preferably from 1 ⁇ sec ⁇ 100 m sec as a pulse width, and more preferably 10 ⁇ sec ⁇ 10 m sec.
  • the irradiation time of the pulsed light is preferably 1 to 100 milliseconds, more preferably 1 to 50 milliseconds, and further preferably 1 to 20 milliseconds. Note that the light irradiation treatment can be performed in an air atmosphere, an inert gas atmosphere, or the like, but is preferably performed in an air atmosphere.
  • the above heat treatment and light irradiation treatment may be performed alone or both may be performed simultaneously. Moreover, after performing one process, you may perform the other process further.
  • the thickness of the source electrode and drain electrode to be formed is not particularly limited, but is preferably 10 nm to 1 ⁇ m, and more preferably 50 to 500 nm.
  • This step is a step of further forming an organic semiconductor layer on the gate insulating film layer on which the above-described source electrode and drain electrode are disposed. More specifically, in this step, the organic semiconductor layer is formed so as to cover the source electrode, the drain electrode, and the gate insulating film layer in a region sandwiched between the source electrode and the drain electrode. Note that this step is not limited to the mode shown in FIG. 1. For example, as shown in the organic thin film transistor 100 in FIG. 2, the gate insulating film layer 16 in a region sandwiched between the source electrode 18 and the drain electrode 20 is covered. It is sufficient that at least the organic semiconductor layer 22 is formed. Below, the material which comprises an organic-semiconductor layer is explained in full detail.
  • ⁇ -conjugated material is used as the organic semiconductor material.
  • ⁇ -conjugated materials include polypyrroles such as polypyrrole, poly (N-substituted pyrrole), poly (3-substituted pyrrole), and poly (3,4-disubstituted pyrrole); polythiophene, poly (3-substituted thiophene) ), Poly (3,4-disubstituted thiophene), polythiophenes such as polybenzothiophene; polyisothianaphthenes such as polyisothianaphthene; polychenylene vinylenes such as polychenylene vinylene; poly (p-phenylene) Poly (p-phenylene vinylene) s such as vinylene); polyanilines such as polyaniline, poly (N-substituted aniline), poly (3-substituted aniline), poly (2,3-substituted aniline); polyace
  • these polymers have the same repeating unit, for example, ⁇ -sexithiophene, ⁇ , ⁇ -dihexyl- ⁇ -sexualthiophene, ⁇ , ⁇ -dihexyl- ⁇ -kinkethiophene, ⁇ , ⁇ , which are thiophene hexamers
  • Oligomers such as -bis (3-butoxypropyl) - ⁇ -sexithiophene and styrylbenzene derivatives can also be preferably used.
  • metal phthalocyanines such as copper phthalocyanine and fluorine-substituted copper phthalocyanine described in JP-A-11-251601, naphthalene 1,4,5,8-tetracarboxylic acid diimide, N, N′-bis (4-trifluoromethyl) Benzyl) naphthalene 1,4,5,8-tetracarboxylic acid diimide with N, N′-bis (1H, 1H-perfluorooctyl), N, N′-bis (1H, 1H-perfluorobutyl) and N, N '-Dioctylnaphthalene-1,4,5,8-tetracarboxylic acid diimide derivative, naphthalene tetracarboxylic acid diimides such as naphthalene-2,3,6,7-tetracarboxylic acid diimide, and anthracene-2,3,6 Condensation of anthracene tetracar
  • thiophene, vinylene, chelenylene vinylene, phenylene vinylene, p-phenylene, a substituent thereof, or two or more of these are used as repeating units, and the number n of the repeating units is 4 to 4 At least one selected from the group consisting of 10 oligomers or polymers having 20 or more repeating units, condensed polycyclic aromatic compounds such as pentacene, fullerenes, condensed ring tetracarboxylic diimides, and metal phthalocyanines. Is preferred.
  • organic semiconductor materials include tetrathiafulvalene (TTF) -tetracyanoquinodimethane (TCNQ) complex, bisethylenetetrathiafulvalene (BEDTTTTF) -perchloric acid complex, BEDTTTTF-iodine complex, TCNQ-iodine complex.
  • TTF tetrathiafulvalene
  • TCNQ bisethylenetetrathiafulvalene
  • BEDTTTTF bisethylenetetrathiafulvalene
  • TCNQ-iodine complex TCNQ-iodine complex
  • Organic molecular complexes such as can also be used.
  • ⁇ conjugated polymers such as polysilane and polygerman, and organic / inorganic hybrid materials described in JP-A-2000-260999 can also be used.
  • organic semiconductor materials examples include DNTT (dinaphtho [2,3-b: 2 ′, 3′-f] thieno [3,2-b] thiophene), DPh-BTBT (2,7-diphenyl [1] benzothieno).
  • the organic semiconductor layer is made of, for example, a material having a functional group such as acrylic acid, acetamide, dimethylamino group, cyano group, carboxyl group, nitro group, benzoquinone derivative, tetracyanoethylene and tetracyanoquino Materials that accept electrons, such as dimethane and derivatives thereof, materials having functional groups such as amino group, triphenyl group, alkyl group, hydroxyl group, alkoxy group, phenyl group, phenylenediamine, etc.
  • a functional group such as acrylic acid, acetamide, dimethylamino group, cyano group, carboxyl group, nitro group, benzoquinone derivative, tetracyanoethylene and tetracyanoquino Materials that accept electrons, such as dimethane and derivatives thereof, materials having functional groups such as amino group, triphenyl group, alkyl group, hydroxyl group, alkoxy group, phenyl group, phenylenediamine
  • Doping means introducing an electron-donating molecule (acceptor) or an electron-donating molecule (donor) into the thin film as a dopant. Therefore, the doped thin film is a thin film containing the condensed polycyclic aromatic compound and the dopant.
  • Either an acceptor or a donor can be used as the dopant used in the present invention.
  • alkali metals such as Li, Na, K, Rb and Cs
  • alkaline earth metals such as Ca, Sr and Ba
  • Y La, Ce, Pr, Nd, Sm, Eu
  • Rd metals such as Gd, Tb, Dy, Ho, Er, Yb, ammonium ions
  • R 4 P + , R 4 As + , R 3 S + each R represents an alkyl group, an aryl group, etc.
  • acetylcholine and the like.
  • either an organic semiconductor layer is prepared in advance and a dopant is introduced later, or a dopant is introduced when an organic semiconductor layer is produced can be used.
  • gas phase doping using a dopant in a gas state gas phase doping using a dopant in a gas state
  • a solid phase doping method for diffusion doping can be mentioned.
  • the efficiency of doping can be adjusted by applying electrolysis.
  • a mixed solution or dispersion of an organic semiconductor compound and a dopant may be simultaneously applied and dried.
  • a dopant when using a vacuum evaporation method, can be introduce
  • an organic semiconductor layer is formed by a sputtering method
  • a dopant can be introduced into a thin film by sputtering using a binary target of an organic semiconductor compound and a dopant.
  • Still other methods include chemical doping such as electrochemical doping, photoinitiated doping, and physics such as ion implantation shown in a publication (Industrial Materials, Vol. 34, No. 4, p. 55, 1986). Any of the chemical dopings can be used.
  • the method for producing the organic semiconductor layer is not particularly limited, and for example, vacuum deposition, molecular beam epitaxial growth, ion cluster beam, low energy ion beam, ion plating, CVD, sputtering, plasma polymerization, electrolysis Examples include polymerization methods, chemical polymerization methods, spray coating methods, spin coating methods, blade coating methods, dip coating methods, cast methods, roll coating methods, bar coating methods, die coating methods, and LB methods, which can be used depending on the material. .
  • spin coating method, blade coating method, dip coating method, roll coating method, bar coating method, die coating method, etc. that can form a thin film easily and precisely using an organic semiconductor solution.
  • the organic semiconductor layer may be formed by discharging an organic semiconductor solution or dispersion with an ink jet and drying and removing the solvent.
  • the characteristic of the obtained transistor is largely influenced by the film thickness of the active layer which consists of organic semiconductors, and the film thickness changes with organic semiconductors. Is preferably 1 ⁇ m or less, more preferably 10 to 300 nm.
  • FIG. 3 shows a schematic view of one embodiment of a top gate-top contact type organic thin film transistor.
  • the organic thin film transistor 200 includes a support 12, an organic semiconductor layer 22 disposed on the support 12, and a source electrode 18 and a drain electrode 20 disposed so as to be in contact with the organic semiconductor layer 22.
  • the gate insulating film layer 16 disposed on the organic semiconductor layer 22 so as to cover the source electrode 18 and the drain electrode 20 is in contact with the surface of the gate insulating film layer 16 opposite to the source electrode 18 and the drain electrode 20 side.
  • the gate electrode 14 arranged as described above.
  • the members constituting the organic thin film transistor 200 shown in FIG. 3 are the same as the members constituting the organic thin film transistor 10 shown in FIG.
  • the organic thin film transistor 200 shown in FIG. 3 and the organic thin film transistor 10 shown in FIG. As in the first embodiment described above, at least one of the source electrode and the drain electrode in the organic thin film transistor 200 is heated or light-baked with respect to the coating film formed using the conductive film-forming composition. It is formed by applying. That is, the method for manufacturing the organic thin film transistor 200 includes at least the source / drain formation step. The method for producing the organic thin film transistor 200 is not particularly limited, and it is sufficient that the organic thin film transistor 200 has the source / drain forming step.
  • the step of forming the organic semiconductor layer 22 on the support 12 (organic semiconductor forming step), Step of forming source electrode 18 and drain electrode 20 (source / drain formation step), step of forming gate insulating film layer 16 (insulating film layer forming step), and step of forming gate electrode 14 (gate forming step) are preferably carried out in this order.
  • the procedure of each process is the same as the procedure of each process in the first embodiment described above.
  • the organic semiconductor layer 22 is not limited to the mode shown in FIG. 3, and the organic semiconductor layer is formed in a region sandwiched between the source electrode 18 and the drain electrode 20 as shown in the organic thin film transistor 300 in FIG. 4. It is sufficient that at least 22 is formed.
  • composition for forming conductive film [Preparation of composition for forming conductive film] ⁇ Composition 1 for electrically conductive film formation> Copper oxide particles (Cai Kasei Co., Ltd., NanoTek CuO; average primary particle size 48 nm) (45 parts by mass) and water (20 parts by mass) were mixed, and a rotating / revolving mixer (Sinky Co., Ltd., Awatori Kentaro ARE-310) was treated for 5 minutes to obtain an aqueous dispersion of copper oxide particles.
  • Copper oxide particles Cai Kasei Co., Ltd., NanoTek CuO; average primary particle size 48 nm
  • water 20 parts by mass
  • Trimethylolpropane (225 parts by weight) and palladium acetate (2 parts by weight) are added to an aqueous dispersion of copper oxide particles, and the mixture is treated for 5 minutes with a rotating / revolving mixer (Shinky Corp., Awatori Kentaro ARE-310).
  • a composition for forming a conductive film was prepared. This composition for forming a conductive film was designated as Composition 1 for forming a conductive film.
  • composition 2 for electrically conductive film formation A conductive film forming composition 2 was prepared in the same manner as the conductive film forming composition 1, except that 1,6-hexanediol (225 parts by weight) was used instead of trimethylolpropane (225 parts by weight). did.
  • composition 3 for forming conductive film A conductive film-forming composition 3 was prepared in the same manner as the conductive film-forming composition 1, except that 1,7-heptanediol (225 parts by weight) was used instead of trimethylolpropane (225 parts by weight). did.
  • composition 4 for forming conductive film A conductive film forming composition 4 was prepared in the same manner as the conductive film forming composition 1 except that triruthenium dodecacarbonyl (2 parts by weight) was used instead of palladium acetate (2 parts by weight).
  • a conductive film forming composition 5 was prepared in the same manner as the conductive film forming composition 1 except that palladium acetate was not used.
  • Table 1 summarizes the compositions of the conductive film forming compositions 1 to 5.
  • Example 1 Production of Organic Semiconductor Transistor Element (Organic Thin Film Transistor)
  • the bottom gate / bottom contact type organic semiconductor transistor element shown in FIG. 1 was produced.
  • Gate electrode formation A silver nanoink (silver nanocolloid H-1, manufactured by Mitsubishi Materials Corporation) is printed on an alkali-free glass substrate (5 cm ⁇ 5 cm) by ink jet printing using DMP2831 (1 picoliter head), and a wiring having a width of 100 ⁇ m and a film thickness of 100 nm. After forming a pattern, the gate electrode wiring was formed by baking at 200 degreeC for 90 minute (s) on a hotplate in air
  • the metal mask 51 was placed on the center of the substrate coated with the insulating film and irradiated with UV ozone for 30 minutes to modify the mask opening to a hydrophilic treatment surface.
  • the metal mask 51 includes a mask portion 52 that blocks light and openings 53 and 54.
  • the conductive film forming composition 1 was ejected by inkjet printing using DMP2831 (1 picoliter head) around the modified portion to form source / drain electrode patterns having a channel length of 50 ⁇ m and a channel width of 320 ⁇ m. The obtained substrate was heated and fired at 200 ° C.
  • Electrode Adhesion Evaluation A tape in accordance with JIS K 6854-1: 1999, using the substrate at the stage where the source / drain electrodes were formed on the gate insulating film layer before forming the organic semiconductor layer as an electrode adhesion evaluation test piece. A peeling test was conducted, and the level of peeling of the wiring portion (source / drain electrode) was evaluated according to the following evaluation criteria. The evaluation results are shown in the column of electrode adhesion in Table 2. A: No peeling at all B: Peeling at an area of less than 5% C: Peeling at an area of 5% or more and less than 20% D: Peeling at an area of 20% or more and less than 90% E: Peeling of an area of 90% or more Yes
  • Carrier Mobility Evaluation Carrier mobility was measured using a semiconductor device analyzer B1500A (manufactured by Agilent). The measurement results are shown in the carrier mobility column of Table 2.
  • Example 2 An organic thin film transistor was fabricated and evaluated in the same manner as in Example 1 except that the thickness of the gate insulating film layer was changed to 300 nm and 1000 nm, respectively. The evaluation results are shown in Table 2.
  • Example 4 As in Example 1, except that an amorphous fluororesin solution (Cytop (R) CTX-807AP, manufactured by Asahi Glass Co., Ltd.) was used as a solution for forming the gate insulating film layer.
  • the organic thin film transistor was fabricated and evaluated in various ways. The evaluation results are shown in Table 2.
  • Example 5 Except that the gate insulating film layer was formed using an amorphous fluororesin solution (Teflon (R) AF-1601S, manufactured by Mitsui DuPont Fluorochemical Co., Ltd.) as a solution for forming the gate insulating film layer.
  • an organic thin film transistor was prepared and various evaluations were performed. The evaluation results are shown in Table 2.
  • Example 6 As a solution for forming a gate insulating film layer, a solution in which polysilsesquioxane (HBSQ101, manufactured by Arakawa Chemical Industries, Ltd.) (100 parts by mass), isophorone diisocyanate (10 parts by mass) and 100 parts by weight of dimethyl glycol is mixed. An organic thin film transistor was prepared and evaluated in the same manner as in Example 1 except that the gate insulating film layer was formed by using it. The evaluation results are shown in Table 2.
  • HBSQ101 polysilsesquioxane
  • Example 7 to 9 organic thin film transistors were produced and evaluated in the same manner as in Example 4 except that the conductive film forming compositions 2 to 4 were used as the conductive film forming compositions, respectively. .
  • the evaluation results are shown in Table 2.
  • Example 10 to 12 firing at the time of forming the source / drain electrodes was performed by heat treatment to light irradiation treatment using pulsed light (Xenon's light sintering apparatus Sinteron 2000, irradiation energy: 5 J / m 2 , pulse width: 2 msec.
  • the organic thin film transistor was prepared and various evaluations were performed in the same manner as in Examples 7 to 9 except that the above was changed. The evaluation results are shown in Table 2.
  • Example 13 firing during the formation of the source / drain electrodes is changed from heat treatment to light irradiation treatment with pulsed light (Xenon's photosintering apparatus Sinteron 2000, irradiation energy: 5 J / m 2 , pulse width: 2 msec). Except for the changed points, the organic thin film transistor was produced and evaluated in the same manner as in Example 6. The evaluation results are shown in Table 2.
  • Comparative Example 1 In Comparative Example 1, an organic thin film transistor was fabricated and evaluated in the same manner as in Example 1 except that the gate insulating film layer was a SiO 2 vapor deposition film. The evaluation results are shown in Table 2.
  • Comparative Example 2 In Comparative Example 2, an organic thin film transistor was fabricated and evaluated in the same manner as in Example 1 except that the source electrode and the drain electrode were fabricated using silver nanocolloid H-1. The evaluation results are shown in Table 2.
  • Comparative Example 3 In Comparative Example 3, a conductive film forming composition 5 (containing no metal particles of Group 8 to 11 elements or salts of Group 8 to 11 elements) was used as the conductive film forming composition, In the same manner as in Example 1, an organic thin film transistor was produced and carrier mobility was evaluated. The evaluation results are shown in Table 2.
  • Comparative Example 4 firing during the formation of the source / drain electrodes is changed from heat treatment to light irradiation treatment with pulsed light (Xenon's light sintering apparatus Sinteron 2000, irradiation energy: 5 J / m 2 , pulse width: 2 msec). Except for the changed points, the organic thin film transistor was produced and evaluated in the same manner as in Comparative Example 1. The evaluation results are shown in Table 2.
  • the transistor manufactured by the method for manufacturing an organic thin film transistor of the present invention is excellent in carrier mobility, migration resistance, and electrode adhesion. From the comparison with Examples 1 to 3, it can be seen that good electrode adhesion can be obtained when the thickness of the gate insulating film layer is at least in the range of 200 nm to 1 ⁇ m. From the comparison between Example 1 and Examples 4 to 6, it can be seen that better electrode adhesion and carrier mobility can be obtained by using a siloxane group-containing polymer or a perfluoro group-containing polymer as a gate insulating film material. .
  • Example 1 and Examples 7 and 8 From the comparison between Example 1 and Examples 7 and 8, it can be seen that when the alcohol compound in the composition for forming a conductive film is a trivalent alcohol, migration resistance superior to that of a divalent alcohol can be obtained. . From the comparison between Example 1 and Example 9, it can be seen that when the palladium salt is included as the salt of the Group 8-11 element, the migration resistance and the electrode adhesion are more excellent than when the ruthenium complex is included. From the comparison between Comparative Example 1 and Example 1, it can be seen that when the gate insulating film layer does not contain an organic compound, the electrode adhesion and the carrier mobility are inferior.

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