WO2011065015A1 - Composition contenant un matériau semi-conducteur organique, et transistor à film mince organique utilisant ladite composition - Google Patents

Composition contenant un matériau semi-conducteur organique, et transistor à film mince organique utilisant ladite composition Download PDF

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WO2011065015A1
WO2011065015A1 PCT/JP2010/006921 JP2010006921W WO2011065015A1 WO 2011065015 A1 WO2011065015 A1 WO 2011065015A1 JP 2010006921 W JP2010006921 W JP 2010006921W WO 2011065015 A1 WO2011065015 A1 WO 2011065015A1
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group
carbon atoms
organic semiconductor
formula
composition according
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近藤浩史
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出光興産株式会社
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/731—Liquid crystalline 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
    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Definitions

  • the present invention relates to a composition capable of being subjected to a coating process and an organic thin film transistor using the composition for a semiconductor layer.
  • Thin film transistors are widely used as display switching elements for liquid crystal display devices and the like.
  • a typical TFT has a gate electrode, an insulator layer, and a semiconductor layer in this order on a substrate, and has a source electrode and a drain electrode formed on the semiconductor layer at a predetermined interval.
  • a semiconductor layer forms a channel region, and an on / off operation is performed by controlling a current flowing between the source electrode and the drain electrode with a voltage applied to the gate electrode.
  • this TFT has been manufactured using amorphous or polycrystalline silicon, but a chemical vapor deposition (CVD) apparatus used for manufacturing a TFT using such silicon is very expensive.
  • CVD chemical vapor deposition
  • Increasing the size of a display device or the like using the method has a problem that it involves a significant increase in manufacturing cost.
  • the process of forming amorphous or polycrystalline silicon is performed at a very high temperature, the types of materials that can be used as a substrate are limited, and a lightweight resin substrate cannot be used. It was.
  • R 11 and R 12 and R 13 and R 14 may be bonded to each other to form a saturated or unsaturated cyclic structure. ) 7).
  • R 11 to R 14 in the formula (4) are each a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, a haloalkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or 1 carbon atom.
  • An organic thin film transistor comprising an organic semiconductor film produced using the composition according to any one of 1 to 12.
  • An organic thin film transistor comprising an organic semiconductor film comprising an organic semiconductor material and a nonionic fatty acid, wherein the nonionic fatty acid is 10 parts by mass or more and 150 parts by mass or less with respect to 100 parts by mass of the organic semiconductor material.
  • composition suitable for a coating process and a high mobility field effect transistor can be provided.
  • the composition of the present invention comprises an organic semiconductor material, a solvent, and a nonionic fatty acid.
  • the content of the nonionic fatty acid is 10 parts by mass or more and 150 parts by mass or less with respect to 100 parts by mass of the organic semiconductor material.
  • the total amount thereof is 10 parts by mass or more and 150 parts by mass or less.
  • the organic semiconductor material is not particularly limited, and may be a p-type organic semiconductor material or an n-type organic semiconductor material.
  • oligophenylene vinylene compounds containing a styryl structure such as 4,4′-bis (styryl) biphenyl, acene such as pentacene, thiophene materials such as polythiophene, oligothiophene, thiophene / phenylene co-oligomer, phthalocyanine, fullerene, perylene
  • perylene-based materials such as tetracarboxylic diimide, pyrene-based materials such as tetraphenylpyrene, and these compounds may further have a substituent.
  • R 1 to R 10 are each a hydrogen atom, a halogen atom, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an alkyl group having 1 to 30 carbon atoms.
  • a ring structure including a nitrogen atom an alkylsulfonyl group having 1 to 30 carbon atoms, a haloalkylsulfonyl group having 1 to 30 carbon atoms, an aromatic hydrocarbon group having 6 to 60 carbon atoms, a carbon number
  • An aromatic heterocyclic group having 1 to 60 carbon atoms, an alkylsilyl group having 1 to 30 carbon atoms, or a cyano group, and these groups may further have a substituent.
  • two adjacent groups may be bonded to each other to form a saturated or unsaturated cyclic structure.
  • each group represented by R 1 to R 10 will be described.
  • the halogen atom include fluorine, chlorine, bromine and iodine atoms.
  • the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, Examples include n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group and the like.
  • haloalkyl group examples include chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, and 2,3-dichloro-t.
  • Examples of the saturated cyclic structure include a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a 1,4-dioxanyl group.
  • Examples of the unsaturated cyclic structure include the same examples as described for the aromatic hydrocarbon group.
  • Ar 2 in the formula (1) is an optionally substituted aromatic hydrocarbon group having 6 to 60 carbon atoms or an optionally substituted aromatic heterocyclic group having 1 to 60 carbon atoms. However, it is preferably an aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent.
  • aromatic hydrocarbon groups include, for example, divalent residues corresponding to benzene, naphthalene, anthracene, phenanthrene, tetracene, chrysene or pentacene.
  • the aromatic heterocyclic group having 1 to 60 carbon atoms is preferably a condensed polycyclic aromatic heterocyclic group having 6 to 60 carbon atoms (preferably 8 to 60 carbon atoms) (condensed polycyclic aromatic heterocyclic group).
  • the ring group is preferably a structure containing a benzene ring or a naphthalene ring, more preferably a structure containing a benzene ring), pyrrole, pyridine, pyrimidine, imidazole, thiazole, dithienobenzene, benzothiadiazole, quinoline, benzothiophene, Divalent residues such as dibenzothiophene, benzofuran or dibenzofuran can be mentioned.
  • Examples of the substituent added to Ar 2 include an alkyl group having 1 to 8 carbon atoms such as a methyl group, an ethyl group, and an n-hexyl group, and a halogen atom such as a fluorine atom.
  • R 1 , R 2 , R 4 to R 7 , R 9 and R 10 are all hydrogen atoms, and at least one of R 3 and R 8 is a halogen atom or carbon number
  • R 11 to R 14 in formula (4) are preferably each a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, a haloalkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, An alkylthio group having 1 to 8 carbon atoms, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms (the two alkyl groups may be bonded to each other to form a ring structure containing a nitrogen atom), An alkylsulfonyl group having 1 to 8 carbon atoms or a cyano group;
  • R 1 , R 2 , R 4 , R 5 , R 6 , R 7 and R 9 to R 14 in formula (4) are hydrogen atoms
  • at least one of R 3 and R 8 is halogen Atoms, alkyl groups having 1 to 30 carbon atoms, preferably 4 to 16 carbon atoms, haloalkyl groups having 1 to 30 carbon atoms, preferably 4 to 16 carbon atoms, 1 to 30 carbon atoms, preferably 4 to 16 carbon atoms
  • a ring structure containing a nitrogen atom may be formed), and R 3 or R 8 which are not these are hydrogen atoms.
  • R 3 and R 8 are more preferably an alkyl group having 4 to 16 carbon atom
  • any one of R 1 to R 14 is preferably a fluorine atom, a cyano group, a trifluoromethyl group, or a pentafluoroethyl group.
  • substituent added to these groups include alkyl groups having 1 to 8 carbon atoms such as a methyl group, an ethyl group, and an n-hexyl group.
  • R 15 to R 22 are the same as R 1 to R 10 in the formula (1).
  • R 15 , R 16 , R 21 , R 22 and R 17 to R 20 may be adjacent to each other to form a saturated or unsaturated cyclic structure.
  • Specific examples of the cyclic structure are the same as those described above. Is mentioned.
  • R 15 to R 22 in Formula (5) are preferably each a hydrogen atom, a halogen atom, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or a carbon number
  • R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 9 , R 10 and R 15 to R 22 in formula (5) are hydrogen atoms
  • R 3 and R 8 At least one of them is a halogen atom, an alkyl group having 1 to 30 carbon atoms, preferably 4 to 16 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, preferably 4 to 16 carbon atoms, 1 to 30 carbon atoms, preferably A haloalkoxy group having 4 to 16 carbon atoms, or a dialkylamino group having 2 to 30 carbon atoms, preferably 4 to 30 carbon atoms (the two alkyl groups may be bonded to each other to form a ring structure containing a nitrogen atom) R 3 or R 8 other than these is a hydrogen atom.
  • R 3 and R 8 are more preferably an alkyl group having 4 to 16 carbon atoms, preferably a chain alkyl group.
  • R 3 and R 8 is an alkyl group having 4 to 16 carbon atoms, a haloalkyl group having 4 to 16 carbon atoms, a haloalkoxy group having 4 to 16 carbon atoms, or a dialkylamino group having 4 to 30 carbon atoms, Since solubility is improved, it is convenient for the production of a coating film.
  • any of R 1 to R 10 is preferably a halogen atom, a cyano group, a trifluoromethyl group, or a pentafluoroethyl group.
  • Aromatic halogenated hydrocarbons such as 1,2,4-trichlorobenzene and o-dichlorobenzene, halogenated hydrocarbons such as 1,2-dichloroethane, 1,1,2,2-tetrachloroethane, chloroform and dichloromethane, Ketones such as cyclohexane and N-methyl-2-pyrrolidone (NMP), sulfoxides such as dimethyl sulfoxide (DMSO), ethers such as cyclohexanone, anisole, dioxane and tetrahydrofuran (THF), and cyclic esters such as ⁇ -butyllactone And the like.
  • the solvent is preferably an aromatic halogenated hydrocarbon or halogenated hydrocarbon in that it does not adversely affect the solubility of the organic semiconductor material and the performance of the organic thin film transistor.
  • the solvent is evaporated prior to the nonionic fatty acid during film formation, so that the solvent and the nonionic fatty acid do not azeotrope.
  • a solvent whose boiling point is 10 ° C. or more lower than that of nonionic fatty acid is used.
  • the amount of the solvent used is preferably 9 parts by mass or more and 999 parts by mass or less (solution concentration: 0.1 to 10% by weight) with respect to 1 part by mass of the organic semiconductor material. Within this range, a uniform thin film can be obtained.
  • the nonionic fatty acid used in the composition of the present invention is an electrically neutral fatty acid having no cation or anion moiety that becomes an ion.
  • salt formation can be suppressed, and operational problems such as hysteresis caused by ionic impurities can be prevented.
  • Nonionic fatty acids include butyric acid, valeric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, ⁇ -linolenic acid, stearidonic acid, Examples include eicosapentaenoic acid, docosahexaenoic acid, linoleic acid, ⁇ -linolenic acid, dihomo- ⁇ -linolenic acid, arachidonic acid, oleic acid, elaidic acid, erucic acid, nervonic acid, and 10-undecylenic acid.
  • Preferred nonionic fatty acids are those in the melting point range described below, and 10-undecylenic acid and caprylic acid are particularly preferred.
  • the melting point of the nonionic fatty acid is preferably 50 ° C. or lower, more preferably 25 ° C. or lower.
  • the lower limit is ⁇ 30 ° C.
  • the content of the nonionic fatty acid is 10 parts by mass or more and 150 parts by mass or less, preferably 25 parts by mass or more and 100 parts by mass or less with respect to 100 parts by mass of the organic semiconductor material. Particularly preferred is 60 parts by mass or more and 100 parts by mass or less from the viewpoint of production stability. Within this range, high mobility can be stably obtained.
  • the organic semiconductor film of the organic thin film transistor of the present invention contains an organic semiconductor material and a nonionic fatty acid, and the nonionic fatty acid is 10 parts by mass or more and 150 parts by mass or less with respect to 100 parts by mass of the organic semiconductor material.
  • the organic thin-film transistor of this invention contains the organic-semiconductor film manufactured using said composition.
  • the organic semiconductor layer is preferably produced by a coating process.
  • the structure of the organic thin film transistor is not particularly limited, and the structure other than the organic semiconductor layer may be a known element structure.
  • the structure other than the organic semiconductor layer may be a known element structure.
  • at least three terminals of a gate electrode, a source electrode, and a drain electrode, an insulator layer, and an organic semiconductor layer are provided on a substrate, and a source-drain current is controlled by applying a voltage to the gate electrode.
  • a specific example of the element structure of the organic thin film transistor will be described with reference to the drawings.
  • the organic thin film transistor 1 of FIG. 1 has a source electrode 20 and a drain electrode 30 formed on a substrate 10 so as to face each other with a predetermined interval.
  • An organic semiconductor layer 40 is formed so as to cover the source electrode 20, the drain electrode 30, and the gap between them, and an insulator layer 50 is further laminated.
  • a gate electrode 60 is formed on the insulating layer 50 and on the gap between the source electrode 20 and the drain electrode 30.
  • the organic thin film transistor 2 in FIG. 2 has a gate electrode 60 and an insulator layer 50 in this order on a substrate 10, and a pair of source electrode 20 and drain formed on the insulator layer 50 at a predetermined interval.
  • An electrode 30 is provided, and the organic semiconductor layer 40 is formed thereon.
  • the organic semiconductor layer 40 forms a channel region, and is turned on / off by controlling a current flowing between the source electrode 20 and the drain electrode 30 with a voltage applied to the gate electrode 60.
  • the insulating layer 50 and the gate electrode 60 are further provided in this order.
  • the organic thin film transistor has a field effect transistor structure. As described above, there are several configurations depending on the position of the electrodes, the layer stacking order, and the like.
  • the organic thin film transistor includes an organic semiconductor layer, a source electrode and a drain electrode formed so as to face each other with a predetermined interval, and a gate electrode formed with a predetermined distance from each of the source electrode and the drain electrode.
  • the current flowing between the source and drain electrodes is controlled by applying a voltage to the gate electrode.
  • the distance between the source electrode and the drain electrode is determined depending on the application, and is usually 0.1 ⁇ m to 1 mm, preferably 1 ⁇ m to 100 ⁇ m, and more preferably 5 ⁇ m to 100 ⁇ m.
  • FIG. 7 shows an organic thin film transistor including a substrate 12 having a function as a gate electrode and a lead wire connecting electrode 70.
  • a substrate 12 that functions as a gate electrode on a lead wire connection electrode 70 in which a Cr layer 74 is laminated on an Au layer 72.
  • An insulator layer 52 and an organic semiconductor layer 40 are formed thereon, and a pair of a source electrode 22 and a drain electrode 32 are formed on the organic semiconductor layer 40 at a predetermined interval.
  • the constituent members of the organic thin film transistor will be described.
  • the organic semiconductor layer is formed using the above composition.
  • the thickness of the organic semiconductor layer is not particularly limited, but is usually 0.5 nm to 1 ⁇ m, and preferably 2 nm to 250 nm.
  • the organic semiconductor layer can be formed by a coating method such as a dipping method, a spin coating method, a casting method, a bar coating method, a roll coating method, or an ink jet method.
  • the substrate plays a role in supporting the structure of the organic thin film transistor.
  • an inorganic compound such as a metal oxide or nitride, a plastic film (PET, PES, PC), a metal substrate, or a composite thereof. It is also possible to use a body or a laminate.
  • a silicon (Si) wafer is often used as a material for the substrate.
  • Si itself can be used as a gate electrode / substrate.
  • the surface of Si can be oxidized to form SiO 2 and used as an insulating layer.
  • a metal layer such as Au may be formed on the Si substrate serving as the substrate and gate electrode as an electrode for connecting the lead wire.
  • Examples of the method for forming the electrode include means such as vapor deposition, electron beam vapor deposition, sputtering, atmospheric pressure plasma method, ion plating, chemical vapor deposition, electrodeposition, electroless plating, spin coating, printing, and ink jet. .
  • a conductive thin film formed using the above method is formed using a known photolithographic method or a lift-off method, on a metal foil such as aluminum or copper.
  • Source electrodes, drain electrodes, gate electrodes, and formation methods thereof include those formed using fluid electrode materials such as solutions, pastes, inks, and dispersions containing the above conductive materials.
  • fluid electrode materials such as solutions, pastes, inks, and dispersions containing the above conductive materials.
  • a fluid electrode material containing a conductive polymer or metal fine particles containing platinum, gold, silver, and copper it is preferable to use a fluid electrode material containing a conductive polymer or metal fine particles containing platinum, gold, silver, and copper.
  • a dispersion containing metal fine particles for example, a known conductive paste may be used.
  • metal fine particle dispersions may be directly patterned by an ink jet method, or may be formed from a coating film by lithograph or laser ablation. Moreover, the patterning method by printing methods, such as a letterpress, an intaglio, a lithographic plate, and screen printing, can also be used. After the electrode is formed and the solvent is dried, the metal fine particles are heat-fused by heating in a shape within a range of 100 ° C. to 300 ° C., preferably 150 ° C. to 200 ° C., if necessary. An electrode pattern having the following shape can be formed.
  • a known conductive polymer whose conductivity is improved by doping is preferably used as another gate electrode, source electrode, and drain electrode material.
  • conductive polyaniline, conductive polypyrrole, conductive polythiophene A complex of polyethylene dioxythiophene and polystyrene sulfonic acid, etc.
  • These materials can reduce the contact resistance between the organic semiconductor layer of the source electrode and the drain electrode.
  • These forming methods may also be patterned by an ink jet method, or may be formed from a coating film by lithography, laser ablation, or the like.
  • the patterning method by printing methods such as a letterpress, an intaglio, a lithographic plate, and screen printing, can also be used.
  • the material for forming the source electrode and the drain electrode is preferably a material having a small electric resistance at the contact surface with the organic semiconductor layer among the examples described above.
  • the electrical resistance at this time corresponds to the field-effect mobility when the current control device is manufactured, and it is preferable that the resistance is as small as possible in order to obtain a large mobility. This is generally determined by the magnitude relationship between the work function of the electrode material and the energy level of the organic semiconductor layer.
  • ba ⁇ 1.5 eV (formula (I)) is preferable, and ba ⁇ 1.0 eV is more preferable. If the above relationship can be maintained in relation to the organic semiconductor layer, a high-performance device can be obtained.
  • the electrode material has a work function as large as possible, and the work function is 4.0 eV or more.
  • the work function is preferably 4.2 eV or more.
  • the work function of the electrode material is preferably as small as possible, and the work function is preferably 4.3 eV or less. More preferably, the work function is 3.7 eV or less.
  • low work function metals have a work function of 4.3 eV or less as described in Chemical Handbook, Basics, pages II-493 (Revised 3rd edition, edited by The Chemical Society of Japan, published by Maruzen Co., Ltd. 1983). What is necessary is just to select from the said list of effective metals, Ag (4.26 eV), Al (4.06, 4.28 eV), Ba (2.52 eV), Ca (2.9 eV), Ce (2.9 eV), Cs (1.95 eV), Er (2.97 eV), Eu (2.5 eV), Gd (3.1 eV), Hf (3.9 eV), In (4.09 eV), K (2.28), La (3.5 eV), Li (2.93 eV), Mg (3.66 eV), Na (2.36 eV), Nd (3.2 eV), Rb (4.25 eV), Sc (3.5 eV), Sm ( 2.7 eV), Ta (4.0, 4.15) V), Y (3.1eV),
  • the material of the insulator layer is not particularly limited as long as it is electrically insulating and can be formed as a thin film.
  • Metal oxide including silicon oxide
  • metal nitride including silicon nitride
  • a material having an electrical resistivity at room temperature of 10 ⁇ cm or higher such as a polymer material or an organic low molecular weight compound material.
  • an inorganic oxide thin film is preferable.
  • wax polyethylene, polypropylene, polyethylene terephthalate, polyoxymethylene, polyvinyl chloride, polyvinylidene fluoride, polysulfone, polyimide cyanoethyl pullulan, poly (vinylphenol) (PVP), poly (methyl methacrylate) (PMMA), polycarbonate (PC ), Polystyrene (PS), polyacrylamide, poly (acrylic acid), novolac resin, resole resin, polyxylylene, epoxy resin, and a polymer material having a high dielectric constant such as pullulan can be used.
  • the organic semiconductor layer can be formed with less damage. Therefore, it is an effective method.
  • the insulator layer may be a mixed layer using a plurality of inorganic or organic compound materials as described above, or may be a laminated structure of these.
  • the performance of the device can be controlled by mixing or laminating a material having a high dielectric constant and a material having water repellency, if necessary.
  • the insulator layer may include an anodic oxide film or the anodic oxide film as a component.
  • the anodized film is preferably sealed.
  • the anodized film is formed by anodizing a metal that can be anodized by a known method. Examples of the metal that can be anodized include aluminum and tantalum, and the anodizing method is not particularly limited, and a known method can be used.
  • An oxide film is formed by anodizing.
  • the thickness of the insulator layer As the thickness of the insulator layer, if the layer is thin, the effective voltage applied to the organic semiconductor increases, so the drive voltage and threshold voltage of the device itself can be lowered, but conversely between the source and gate. Therefore, it is necessary to select an appropriate film thickness, which is normally 10 nm to 5 ⁇ m, preferably 50 nm to 2 ⁇ m, and more preferably 100 nm to 1 ⁇ m.
  • An example is a method in which the film is brought into contact with the surface of the film to form a self-assembled film, followed by appropriate drying treatment.
  • a method in which a film made of polyimide or the like is provided on the surface of the insulating film and the surface is rubbed so as to be used for liquid crystal alignment is also preferable.
  • Examples of the method for forming the insulator layer include a vacuum process, a molecular beam epitaxial growth method, an ion cluster beam method, a low energy ion beam method, an ion plating method, a CVD method, a sputtering method, and an atmospheric pressure plasma method.
  • Wet processes such as spray coating method, spin coating method, blade coating method, dip coating method, casting method, roll coating method, bar coating method, coating method such as die coating method, and patterning methods such as printing and inkjet. Can be used depending on the material.
  • the wet process is a method of applying and drying a liquid in which fine particles of inorganic oxide are dispersed in an arbitrary organic solvent or water using a dispersion aid such as a surfactant as required, or an oxide precursor, for example,
  • a so-called sol-gel method in which a solution of an alkoxide body is applied and dried is used.
  • a method for forming the organic thin film transistor is not particularly limited, and may be a known method. According to a desired element configuration, the substrate is loaded, the gate electrode is formed, the insulator layer is formed, the organic semiconductor layer is formed, the source electrode is formed, and the drain electrode is formed. It is preferable to form a series of device manufacturing steps up to formation without being exposed to the atmosphere at all, since it is possible to prevent the device performance from being hindered by moisture, oxygen, etc. in the atmosphere due to contact with the atmosphere. When it is unavoidable that the atmosphere must be exposed to the atmosphere once, the process after the organic semiconductor layer deposition is not exposed to the atmosphere at all.
  • a gas barrier layer may be formed on the whole or part of the outer peripheral surface of the organic transistor element.
  • a material for forming the gas barrier layer those commonly used in this field can be used, and examples thereof include polyvinyl alcohol, ethylene-vinyl alcohol copolymer, polyvinyl chloride, polyvinylidene chloride, and polychlorotrifluoroethylene.
  • the inorganic substance which has the insulation illustrated in the said insulator layer can also be used.
  • Organic thin film light emitting transistor It is possible to provide an organic thin film light emitting transistor that emits light using a current flowing between a source electrode and a drain electrode and controls light emission by applying a voltage to a gate electrode. That is, an organic thin film transistor can be used as a light emitting element (organic EL). Since the transistor for controlling light emission and the light emitting element can be integrated, the aperture ratio of the display can be improved and the cost can be reduced by the simplification of the manufacturing process, which provides a great practical advantage. When used as an organic light emitting transistor, it is necessary to inject holes from one of the source electrode and the drain electrode and electrons from the other, and the following conditions are preferably satisfied in order to improve the light emitting performance.
  • At least one of the source electrode and the drain electrode is a hole injecting electrode in order to improve hole injecting property.
  • a hole injection electrode is an electrode containing a substance having a work function of 4.2 eV or higher.
  • it is an organic thin film light emitting transistor provided with an electrode in which one is hole injecting and the other is electron injecting.
  • the hole injection layer In order to improve the hole injection property, it is preferable to insert a hole injection layer between at least one of the source electrode and the drain electrode and the organic semiconductor layer.
  • the hole injection layer include amine-based materials used as a hole injection material and a hole transport material in an organic EL device.
  • an electron injection layer between at least one of the source electrode and the drain electrode and the organic semiconductor layer.
  • the electron injection material used for the organic EL element can be used for the electron injection layer as well as the hole.
  • it is an organic thin film light emitting transistor having a hole injection layer on one electrode and an electron injection layer on the other electrode.
  • Example 1 preparation of composition for forming an organic semiconductor layer
  • the following organic semiconductor material (175) was dissolved in 0.5 parts by mass in chloroform (boiling point: 61 ° C.), and 10-undecylenic acid (melting point: 25 ° C., boiling point: 275 ° C.) was added to 100 parts by mass of the organic semiconductor material.
  • seven different composition solutions added with 10, 25, 50, 60, 80, 100, and 150 parts by mass were prepared.
  • the glass substrate was ultrasonically cleaned with a neutral detergent, pure water, acetone, and ethanol for 30 minutes each, and then a gold (Au) film was formed to 40 nm by a sputtering method to produce a gate electrode.
  • this substrate was set in a film forming section of a thermal CVD apparatus.
  • 250 mg of a polyparaxylene derivative polyparaxylene chloride (Parylene)) (trade name: diX-C, manufactured by Daisan Kasei Co., Ltd.), which is a raw material for the insulating layer, was placed in a petri dish.
  • the evaporation part was heated to 180 ° C. and the polymerization part was heated to 680 ° C. and left for 2 hours to form an insulating layer having a thickness of 1 ⁇ m on the gate electrode.
  • a film was formed on a substrate on which an insulator layer was formed using a spin coater (Mikasa Co., Ltd .: 1H-D7) and dried at 80 ° C. in a nitrogen atmosphere to form an organic semiconductor layer. A film was formed. Next, a gold film was formed to a thickness of 50 nm through a metal mask using a vacuum evaporation apparatus, so that a source electrode and a drain electrode that were not in contact with each other were formed to have a gap (channel length) of 75 ⁇ m. At this time, an organic thin film transistor was manufactured by forming a film so that the width (channel width) of the source electrode and the drain electrode was 5 mm.
  • a gate voltage of ⁇ 40 V was applied to the gate electrode of the obtained organic thin film transistor, and a current was applied by applying a voltage between the source and drain. In this case, electrons were induced in the channel region (between the source and drain) of the organic semiconductor layer and operated as a p-type transistor.
  • the field effect mobility ⁇ of holes in the current saturation region was calculated from the following formula (A). The results are shown in Table 1.
  • I D (W / 2L) ⁇ C ⁇ ⁇ (V G ⁇ V T ) 2 (A)
  • ID is a source-drain current
  • W is a channel width
  • L is a channel length
  • C is a capacitance per unit area of the gate insulator layer
  • V T is a gate threshold voltage
  • V G is a gate voltage.
  • Comparative Example 1 Three different types of solutions were prepared in the same manner as in Example 1 except that the amount of 10-undecylenic acid added was 0.5, 200 parts by weight with respect to 100 parts by weight of the organic semiconductor material, and an organic thin film transistor was prepared. The hole field-effect mobility ⁇ was calculated. The results are shown in Table 1. The formed organic semiconductor film was analyzed by liquid chromatography in the same manner as in Example 1. In the organic semiconductor film, it was confirmed that the organic semiconductor material and 10-undecylenic acid were present at a ratio equivalent to the ratio in the composition solution used for formation.
  • Example 2 Preparation of composition for forming an organic semiconductor layer
  • caprylic acid melting point: 15 ° C., boiling point: 233 ° C.
  • Table 2 The results are shown in Table 2.
  • the organic-semiconductor material and caprylic acid of the ratio equivalent to the used composition solution were detected by the liquid chromatography analysis in the organic-semiconductor film.
  • Comparative Example 2 Three different types of solutions were prepared in the same manner as in Example 2 except that the amount of caprylic acid added was 0.5, 200 parts by mass with respect to 100 parts by mass of the organic semiconductor material. The field effect mobility ⁇ of the hole was calculated. The results are shown in Table 2. Moreover, the organic-semiconductor material and caprylic acid of the ratio equivalent to the used composition solution were detected by the liquid chromatography analysis in the organic-semiconductor film.
  • the composition of the present invention can be used for a semiconductor film of an organic thin film transistor.
  • the organic thin film transistor of the present invention can be used for display electronic devices such as electronic devices used for thin film displays, wearable electronic devices such as plastic IC cards and information tags, medical devices such as biosensors, and measuring devices.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Thin Film Transistor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne une composition composée d'un matériau semi-conducteur organique, d'un solvant, et d'un acide gras non ionique. La composition est caractérisée en ce que l'acide gras non ionique est contenu dans une quantité allant de 10 à 150 parties en masse (inclus) par rapport à 100 parties en masse du matériau semi-conducteur organique.
PCT/JP2010/006921 2009-11-30 2010-11-26 Composition contenant un matériau semi-conducteur organique, et transistor à film mince organique utilisant ladite composition WO2011065015A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2021136402A (ja) * 2020-02-28 2021-09-13 三菱ケミカル株式会社 光電変換層作成用インク、光電変換素子の製造方法、光電変換素子、及び光センサー

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006352143A (ja) * 2005-06-18 2006-12-28 Samsung Sdi Co Ltd 有機半導体のパターニング方法
JP2006351543A (ja) * 2005-06-18 2006-12-28 Samsung Sdi Co Ltd ナノ導電性膜のパターニング方法
JP2007137801A (ja) * 2005-11-16 2007-06-07 Fuji Xerox Co Ltd 電荷輸送性化合物、それを用いた電荷輸送性膜及び電界発光素子
WO2008044695A1 (fr) * 2006-10-12 2008-04-17 Idemitsu Kosan Co., Ltd. Dispositif de transistor organique à couche mince et transistor organique à couche mince émetteur de lumière

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006352143A (ja) * 2005-06-18 2006-12-28 Samsung Sdi Co Ltd 有機半導体のパターニング方法
JP2006351543A (ja) * 2005-06-18 2006-12-28 Samsung Sdi Co Ltd ナノ導電性膜のパターニング方法
JP2007137801A (ja) * 2005-11-16 2007-06-07 Fuji Xerox Co Ltd 電荷輸送性化合物、それを用いた電荷輸送性膜及び電界発光素子
WO2008044695A1 (fr) * 2006-10-12 2008-04-17 Idemitsu Kosan Co., Ltd. Dispositif de transistor organique à couche mince et transistor organique à couche mince émetteur de lumière

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2021136402A (ja) * 2020-02-28 2021-09-13 三菱ケミカル株式会社 光電変換層作成用インク、光電変換素子の製造方法、光電変換素子、及び光センサー

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