WO2007125671A1 - Transistor a effet de champ - Google Patents

Transistor a effet de champ Download PDF

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Publication number
WO2007125671A1
WO2007125671A1 PCT/JP2007/053092 JP2007053092W WO2007125671A1 WO 2007125671 A1 WO2007125671 A1 WO 2007125671A1 JP 2007053092 W JP2007053092 W JP 2007053092W WO 2007125671 A1 WO2007125671 A1 WO 2007125671A1
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WIPO (PCT)
Prior art keywords
field effect
group
effect transistor
formula
semiconductor
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PCT/JP2007/053092
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English (en)
Japanese (ja)
Inventor
Masaaki Ikeda
Hirokazu Kuwabara
Chihaya Adachi
Kazuo Takimiya
Original Assignee
Nippon Kayaku Kabushiki Kaisha
Hiroshima University
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Application filed by Nippon Kayaku Kabushiki Kaisha, Hiroshima University filed Critical Nippon Kayaku Kabushiki Kaisha
Priority to JP2008513095A priority Critical patent/JP5167560B2/ja
Publication of WO2007125671A1 publication Critical patent/WO2007125671A1/fr

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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
    • H10K85/649—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
    • 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]
    • H10K10/464—Lateral top-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
    • 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
    • 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
    • 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

Definitions

  • the present invention relates to a field effect transistor. More specifically, the present invention relates to a field effect transistor having a specific organic heterocyclic compound and an electron transport semiconductor material.
  • a field effect transistor generally has a structure in which a semiconductor material on a substrate is provided with a source electrode, a drain electrode, a gate electrode and the like via these electrodes and an insulator layer, and a logic circuit element.
  • a semiconductor material on a substrate is provided with a source electrode, a drain electrode, a gate electrode and the like via these electrodes and an insulator layer, and a logic circuit element.
  • inorganic semiconductor materials centered on silicon are used for field effect transistors, and thin film transistors made of amorphous silicon on a substrate such as glass are used for displays and the like.
  • it is necessary to process the field effect transistor at a high temperature or in a vacuum, and it requires a large amount of energy for capital investment and manufacturing, so the cost becomes very high.
  • substrates that are not sufficiently heat resistant such as films and plastics cannot be used as substrates because they are exposed to high temperatures during the production of field effect transistors. Is limited.
  • DP h BDS compounds and DPh-BSBS compounds show excellent P-type semiconductor characteristics and are reported to be more stable, and as practical organic semiconductor materials, they can be used as organic field-effect transistors.
  • Expectations are high (see Patent Document 3, Non-Patent Document 1, and Non-Patent Document 2)
  • Organic semiconductor materials with electron transport (N-type) properties include fluorinated pentacene, fluorinated phthalocyanine, C60, and perylenetetracarboxylic anhydride.
  • ambipolar type field effect transistors that can be driven by N-type or P-type by changing the polarity of the gate voltage on the same element are attracting attention.
  • This realization makes it possible to fabricate CMOS circuits much more easily than combining the above-mentioned P-type and N-type separately, and opens the way for other applications.
  • ambipolar type electric For the production of field effect transistors, the above-mentioned pentacene and fluorinated pentacene are used, and phthalocyanine and fluorinated phthalocyanine are used for lamination and mixing. 3 and Non-Patent Document 4, Non-Patent Document 4).
  • an ambipolar type field effect transistor can be produced by using calcium having a low work function for an electrode using a single material.
  • Patent Document 1 Japanese Patent Application Laid-Open No. 2001-94107
  • Patent Document 2 JP-A-6-177380
  • Patent Document 3 Japanese Patent Laid-Open No. 2005-154371
  • Non-Patent Document 1 OK. AM. CHEM. SOC. 2004, 126, 5084-5085
  • Non-Patent Document 2 OK. AM. CHEM. SOC. 2006, 128, 3044- 3050
  • Non-Patent Document 3 OK. AM. CHEM. SOC. 2004, 126, 8138 -8140
  • Non-Patent Document 4 APPL PHYS. LETT. 86, 253505 (2005)
  • Non-Patent Document 5 APPL PHYS. LETT. 87, 093507 (2005)
  • An object of the present invention is to provide an ambipolar field effect transistor having a practical level of charge mobility and excellent stability in the atmosphere.
  • the present inventors have achieved excellent carrier mobility by using a bicyclic compound having a specific structure and an electron transport semiconductor material as constituent components.
  • a field effect transistor excellent in stability was obtained, and it was found that the device exhibited unpolar characteristics, and the present invention was completed.
  • the configuration of the present invention is as follows.
  • X to X each independently represent a sulfur atom, a selenium atom or a tellurium atom
  • the present invention is a field effect transistor using a specific organic compound and an electron transport semiconductor material as constituent components.
  • a bicyclic compound represented by the above formula (1), (2) or (3) is used as the organic compound. These compounds are materials that have been used as hole transport organic semiconductors. First, the compounds represented by formulas (1), (2), and (3) will be described.
  • X to X are each independently a sulfur atom, a selenium atom or a tellurium atom, preferably
  • R 1 to R may be independently substituted
  • aromatic group in the aromatic group which may be substituted examples include aromatic hydrocarbon groups such as phenyl group, naphthyl group, anthryl group, phenanthryl group, pyrenyl group and benzopyrenyl group, pyridyl group, and bilazyl group.
  • aromatic hydrocarbon groups such as phenyl group, naphthyl group, anthryl group, phenanthryl group, pyrenyl group and benzopyrenyl group, pyridyl group, and bilazyl group.
  • Pyrimidyl group Quinolyl group, Isoquinolyl group, Pyrrolyl group, Indolenyl group, Imidazolyl group, Carbazolyl group, Chenyl group, Furyl group, Viral group, Pyridonyl group And a condensed heterocyclic group such as a benzofuryl group.
  • Examples of the substituent in the aromatic group which may be substituted are not particularly limited, but may be an aliphatic hydrocarbon group which may have a substituent (for example, a halogen atom, a hydroxyl group as a substituent) A mercapto group, a carboxylic acid group, a sulfonic acid group, a nitro group, an alkoxyl group, an alkyl-substituted amino group, an aryl substituted amino group, an unsubstituted amino group, an aryl group, an acyl group, an alkoxycarbonyl group, etc.); ⁇ Aromatic group (as a substituent, for example, Alkyl group, halogen atom, hydroxyl group, mercapto group, carboxylic acid group, sulfonic acid group, nitro group, alkoxyl group, alkyl-substituted amino group, aryl-substituted amino group, unsubstituted amino group, ary
  • an aliphatic hydrocarbon group which may have a substituent an aromatic group which may have a substituent, a cyano group, a nitro group, an acyl group, a halogen atom, a hydroxyl group, a mercapto group, a substituted or non-substituted group.
  • a substituted amino group, an alkoxyl group, an aromatic oxy group which may have a substituent, and the like are preferable. More preferably, it may have a substituent! ⁇ ⁇ May have an aliphatic hydrocarbon group or a substituent! ⁇ Aromatic group, nitro group, halogen atom, substituted or unsubstituted amino group, alkoxyl group Etc. Most preferably, it may have an aliphatic hydrocarbon group which may have a substituent or may have a substituent, and examples thereof include V, an aromatic group and a halogen atom.
  • examples of the aliphatic hydrocarbon group include a saturated or unsaturated linear, branched or cyclic aliphatic hydrocarbon group, and the carbon number thereof is preferably 120.
  • examples of the saturated or unsaturated linear or branched aliphatic hydrocarbon group include, for example, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, iso-butyl group, and aryl group.
  • cyclic aliphatic hydrocarbon group examples include cycloalkyl groups having 3 to 12 carbon atoms such as a cyclohexyl group, a cyclopentyl group, an adamantyl group, and a norbornyl group.
  • the aromatic group is the same as the aromatic group in the optionally substituted aromatic group.
  • H H H H H H >> a H H s s 6
  • Table 2 shows examples (compound No. 112 to compound No. 137) of phenyl-substituted compounds represented by the following formula (5) among the compounds represented by the formula (2).
  • the phenyl group is abbreviated as Ph
  • the 4-phenylphenol group as 4 PhPh
  • the naphthyl group as Np
  • the phenyl group as Th.
  • All alkyl groups are linear alkyl groups.
  • Table 3 shows examples of phenyl-substituted ich compounds represented by the following formula (6) among the compounds represented by formula (3) (Dich compounds No. 1 52 to Compound No. 1). 228).
  • the phenyl group is abbreviated as Ph
  • the 4-monophenyl group as 41-PhPh
  • the 4-monopyridyl group as 41-Py
  • the naphthyl group as Np
  • the phenyl group as Th.
  • All alkyl groups not specifically mentioned are linear alkyl groups.
  • Examples of the electron transport semiconductor material include organic and inorganic materials.
  • Organic semiconductor materials include naphthalenetetracarboxylic anhydride and its imidized products, perylenetetracarboxylic acid anhydride and its imidized products, pentacene fluorides, phthalocyanine fluorides, oligothiophene alkyl fluoride derivatives, Fullerenes (such as C60 and C70), caged carbon nanomaterials such as carbon nanotubes and carbon nanohorns, and inorganic semiconductor materials include, for example, n- doped silicon, germanium, TiO, ZnO, SnO, Nb O, WO, In O
  • organic semiconductors and more preferred are fullerenes and cage-like carbon nanomaterials such as carbon nanotubes and carbon nanohorns.
  • fullerenes and cage-like carbon nanomaterials such as carbon nanotubes and carbon nanohorns.
  • Examples include fullerenes such as C60 and C70.
  • FET Field effect transistor
  • a field effect transistor has a structure in which a gate electrode is insulated by an insulating film (Metal
  • Insulator—Semiconductor; MIS structure) is generally used.
  • An insulating film that uses a metal oxide film is called a MOS structure.
  • Others have a structure (MES) in which a gate electrode is formed through a Schottky barrier, but an MIS structure is often used for FETs using organic semiconductor materials.
  • FIG. 1 shows some embodiments of the field effect transistor (device) of the present invention.
  • 1 represents a source electrode
  • 2 represents a semiconductor layer
  • 3 represents a drain electrode
  • 4 represents an insulator layer
  • 5 represents a gate electrode
  • 6 represents a substrate.
  • the arrangement of each layer and electrode can be appropriately selected depending on the use of the element.
  • a to D are called lateral FETs because current flows in parallel to the substrate.
  • A is called bottom contact type structure and B is called top contact type structure.
  • C is a structure often used to make organic single-crystal FETs.
  • a source and drain electrode and an insulator layer are provided on a semiconductor, and a gate electrode is formed thereon.
  • D is a structure called a top & bottom contact transistor.
  • E is a schematic diagram of an electrostatic induction transistor (SIT), which is a FET with a vertical structure.
  • SIT electrostatic induction transistor
  • a large amount of carriers can move at a time because the current flow spreads in a plane.
  • the source and drain electrodes are arranged vertically, the distance between the electrodes can be reduced, so that the response is fast. Therefore, it can be preferably applied to applications such as passing a large current or performing high-speed switching.
  • the substrate 6 needs to be able to hold each layer formed thereon without peeling off.
  • an insulating material such as a resin film, paper, glass, quartz, ceramic, etc., a material in which an insulating layer is formed on a conductive substrate such as a metal or an alloy, a material composed of various combinations such as a resin and an inorganic material Etc.
  • resin films that can be used include polyethylene terephthalate, polyethylene naphthalate, polyethersulfone, Examples include lyamide, polyimide, polycarbonate, cenorelose triacetate, and polyetherimide.
  • the thickness of the substrate is usually 1 ⁇ m to 10 mm, preferably 5 ⁇ m to 5 mm.
  • the source electrode 1, the drain electrode 3, and the gate electrode 5 are made of a conductive material.
  • Conductive polymer compounds such as polyacetylene, polyparaphenylene biylene, and polydiacetylene; semiconductors such as silicon, germanium, and gallium arsenide; carbon materials such as carbon black, fullerene, carbon nanotube, and graphite can be used.
  • the conductive polymer compound and the semiconductor may be doped. Examples of the dopant at that time include acids such as hydrochloric acid, sulfuric acid, and sulfonic acid, Lewis acids such as PF, AsF, and FeCl,
  • a halogen atom such as iodine or a metal atom such as lithium, sodium or potassium is used.
  • a conductive composite material in which carbon black, metal particles, or the like is dispersed in the above material is also used. These materials can change the work function of the electrode, adjust the mobility of electrons and holes, and obtain a field effect transistor having good anno-polar characteristics.
  • the force wiring in which wiring is connected to each electrode 1, 3, and 5 is also made of the same material as the electrode.
  • the insulator layer 4 is made of an insulating material.
  • an insulating material for example, polyparaxylylene, polyacrylate, polymethylmetatalylate, polystyrene, polybutylphenol, polyamide, polyimide, polycarbonate, polyester, polybutyl alcohol, polyacetate vinyl, polyurethane, polysulfone, epoxy resin, Polymers such as phenol resin and copolymers combining these; oxides such as silicon dioxide, aluminum oxide, titanium oxide and tantalum oxide; ferroelectric oxides such as SrTiO and BaTiO; silicon nitride , Aluminum nitride
  • Nitride such as sulfur; sulfide; dielectric such as fluoride, or particles of these dielectrics Scattered polymers can be used.
  • the film thickness of the insulator layer 4 varies depending on the material, but is usually 0.1 nm to: LOO ⁇ m, preferably 0.5 nm to 50 ⁇ m, more preferably 5 nm to: L0 ⁇ m.
  • the semiconductor layer 2 As a material for the semiconductor layer 2, at least one compound represented by the formula (1), (2) or (3) and the above-described electron transport semiconductor material are used as constituent components. As the material for the semiconductor layer 2, the compounds of the formulas (1) and (3) are particularly preferred.
  • the material of the semiconductor layer may contain a mixture of these components, but with respect to the total weight of the material, the compound represented by the formula (1), (2) or (3) and the above-mentioned It is necessary to contain a total of 50% by mass, preferably 80% by mass or more, and more preferably 95% by mass or more of electron transport semiconductor materials. In order to improve the characteristics of field effect transistors and to provide other characteristics, other semiconductor materials and various additives can be mixed or stacked as required! Don't hesitate! ⁇ .
  • the semiconductor layer 2 has a single layer structure in which the compound represented by the formula (1), (2), or (3) and the above-described electron transport semiconductor material are mixed. Therefore, it may have a laminated structure.
  • the thickness of the semiconductor layer 2 is preferably as thin as possible without losing necessary functions.
  • the device characteristics do not depend on the film thickness if the film thickness exceeds a predetermined value, while the leakage current increases as the film thickness increases. This is because there are cases.
  • an Inn to show the required functionality ⁇ 10 / ⁇ ⁇ , preferably 5 nm to 5 / ⁇ ⁇ , more preferably 10 ⁇ to 3 / ⁇ ⁇ .
  • the compound represented by the formula (1), (2) or (3) and the above-described electron transport semiconductor material have a laminated structure, the total film thickness is the same as described above. Each film thickness can be adjusted as long as necessary functions are not lost. Moreover, it is considered that the mobility of electrons and holes is changed by adjusting the mixing ratio and film thickness of these materials, and a field effect transistor having good unpolar characteristics can be obtained.
  • the field effect transistor of the present invention other layers can be provided between the layers or on the outer surface of the element as necessary.
  • a protective layer is formed directly on the semiconductor layer or via another layer, the influence of outside air such as humidity and oxygen can be reduced, and the ON ZOFF ratio of the element can be increased.
  • electrical characteristics can be stabilized.
  • the material of the protective layer is not particularly limited, but examples thereof include films made of various resins such as epoxy resin, acrylic resin such as polymethyl methacrylate, polyurethane, polyimide, polybutyl alcohol, fluorine resin, polyolefin, silicon oxide,
  • a film made of a dielectric such as an inorganic oxide film or a nitride film, such as aluminum oxide or silicon nitride, is preferably used.
  • a resin having a small oxygen or moisture permeability and low water absorption is preferred.
  • protective materials developed for organic EL displays can also be used.
  • the film thickness of the protective layer is a force capable of adopting an arbitrary film thickness depending on the purpose, usually lOOnm ⁇ : Lmm.
  • the characteristics of the element can be improved by performing surface treatment on a substrate or an insulator layer on which a semiconductor is stacked. For example, by adjusting the degree of hydrophilic Z-hydrophobicity of the substrate surface, the film quality of the film formed thereon can be improved.
  • the characteristics of organic semiconductor materials can vary greatly depending on the state of the film, such as molecular orientation. For this reason, it is considered that molecular orientation at the interface between the substrate and a semiconductor film formed thereafter is controlled by the substrate surface treatment, and characteristics such as carrier mobility are improved.
  • substrate treatment examples include hydrophobization treatment with hexamethyldisilazane, cyclohexene, octadecyltrichlorosilane, acid treatment with hydrochloric acid, sulfuric acid, acetic acid, etc., sodium hydroxide, sodium hydroxide, potassium hydroxide. , Alkali treatment with calcium hydroxide, ammonia, etc., ozone treatment, fluorination treatment, plasma treatment with oxygen, argon, etc., Langmuir's formation of a membrane film, other insulator or semiconductor thin film formation treatment, Examples thereof include mechanical treatment, electrical treatment such as corona discharge, and rubbing treatment using fibers.
  • a vacuum deposition method for example, a sputtering method, a coating method, a printing method, a sol-gel method, or the like can be appropriately employed.
  • This manufacturing method can be similarly applied to the field effect transistors of the other embodiments described above.
  • the substrate 6 It is manufactured by providing necessary layers and electrodes on the substrate 6 (see FIG. 2 (1)). As a substrate What was demonstrated above can be used. It is also possible to perform the above-mentioned surface treatment on this substrate.
  • the thickness of the substrate 6 is preferably thin as long as necessary functions are not hindered. Although it varies depending on the material, it is generally 1 ⁇ m to 10 mm, preferably 5 ⁇ m to 5 mm. Also, if necessary, let the substrate have the electrode function.
  • a gate electrode 5 is formed on the substrate 6 (see FIG. 2 (2)).
  • the electrode material described above is used as the electrode material.
  • Various methods can be used as the method for forming the electrode film. For example, a vacuum deposition method, a sputtering method, a coating method, a thermal transfer method, a printing method, a sol-gel method, and the like are employed. It is preferable to perform patterning as needed so as to obtain a desired shape during or after film formation.
  • Various methods can be used as the patterning method. For example, a photolithography method combining a photoresist patterning and etching can be used.
  • the film thickness of the gate electrode 5 varies depending on the material. Usually, it is 0.1 ⁇ to 10 / ⁇ , preferably 0.5 nm to 5 ⁇ m, more preferably lnm to 3 ⁇ m. Further, when the gate electrode serves as the substrate, it may be larger than the above film thickness.
  • An insulating layer 4 is formed on the gate electrode 5 (see FIG. 2 (3)).
  • the insulator material those described above are used.
  • Various methods are used to form the insulator layer 4. For example, spin coating, spray coating, dip coating, casting, bar coating, blade coating, etc., screen printing, offset printing, ink jet printing, vacuum deposition, molecular beam epitaxy, ion cluster single beam And dry process methods such as ion plating, sputtering, atmospheric pressure plasma, and CVD.
  • a method of forming an oxide film on a metal such as aluminium on silicon or a thermal oxide film of silicon is employed in the sol-gel method.
  • the insulator layer can be subjected to a predetermined surface treatment.
  • the surface treatment method the same surface treatment as that of the substrate can be used.
  • the thickness of the insulator layer 4 is preferably thin as long as its function is not impaired. Usually 0.1 ⁇ to 100 / ⁇ ⁇ , preferably 0.5 nm to 50 ⁇ m, more preferably 5 nm to LO ⁇ m.
  • the formation method of the source electrode 1 and the drain electrode 3 can be formed according to the case of the gate electrode 5 (see FIG. 2 (4)).
  • the materials described above are used.
  • Various methods can be used for forming the semiconductor layer. Formation methods in vacuum processes such as sputtering, CVD, molecular beam epitaxy, and vacuum deposition, and coating such as dip coating, die coater, roll coater, bar coater, and spin coating It can be broadly divided into formation methods by solution processes such as the method, ink jet method, screen printing method, offset printing method, and micro contact printing method.
  • solution processes such as the method, ink jet method, screen printing method, offset printing method, and micro contact printing method.
  • a method in which the semiconductor material is heated in a crucible metal boat under vacuum and the evaporated semiconductor material is deposited (deposited) on the substrate (exposed portions of the insulator layer, the source electrode and the drain electrode) (vacuum deposition method) ) Is preferably employed.
  • the degree of vacuum is usually 1.0 X 10 _1 Pa or less, preferably 1. OX 10 _4 Pa or less.
  • the semiconductor film Since the characteristics of the field effect transistor change, it is preferable to carefully select the substrate temperature.
  • the substrate temperature during vapor deposition is usually 0 to 200 ° C, preferably 10 to 150 ° C.
  • the deposition rate is usually from 0.001 nmZ seconds to lOnmZ seconds, and preferably from 0. Olm mZ seconds to InmZ seconds.
  • the film thickness of the semiconductor layer formed from a semiconductor material is usually In m to 10 ⁇ m, or preferably 5 nm to l ⁇ m.
  • a sputtering method is used in which accelerated ions such as argon collide with the material target to knock out material atoms and attach them to the substrate. May be.
  • accelerated ions such as argon collide
  • inorganic semiconductor materials have boiling points Various processes can be used because high deposition can be difficult.
  • each material is heated and evaporated sequentially.
  • a semiconductor layer having a structure in which the materials are mixed can be obtained by co-evaporation in which each material is heated and evaporated simultaneously.
  • the organic semiconductor material in the present invention is a relatively low molecular weight compound, such a vacuum process can be preferably used. Although such a vacuum process requires somewhat expensive equipment, it has the advantage that a uniform film can be easily obtained with good film formability.
  • the material is dissolved or dispersed in a solvent and applied to a substrate (exposed portions of the insulator layer, the source electrode, and the drain electrode).
  • Coating methods include casting, spin coating, dip coating, blade coating, wire bar coating, spray coating and other coating methods, inkjet printing, screen printing, offset printing, letterpress printing and other printing methods, and microcontact.
  • a soft lithography method such as a printing method, or a combination of these methods may be employed.
  • the Langmuir project method in which a monomolecular film formed on the water surface is transferred to the substrate and laminated, the liquid crystal is melted between two substrates or introduced between the substrates by capillary action.
  • the thickness of the semiconductor layer formed by these methods is preferably thin as long as the function is not impaired. There is a concern that the leakage current increases as the film thickness increases.
  • the thickness of the semiconductor layer is usually 1 ⁇ -10 / ⁇ , preferably 5 nm-5 ⁇ m, more preferably 10 nm-3 ⁇ m.
  • a mixed film of semiconductor materials can be easily obtained by dissolving each material together and forming the film by the above process.
  • the solubility of each material in a solvent and the film formed earlier during lamination may be eroded by the solution of the material to be formed later. Optimization is required.
  • a large-area field-effect transistor is used with relatively inexpensive equipment. The ability to manufacture a transistor is advantageous.
  • the semiconductor layer thus formed can be further improved in characteristics by post-processing.
  • the heat treatment can alleviate distortion in the film generated during film formation, and can improve characteristics and improve stability.
  • oxidizing or reducing gases or liquids such as oxygen and hydrogen
  • characteristics can be changed by adding a trace amount of elements, atomic groups, molecules, and polymers to the semiconductor layer.
  • elements for example, oxygen, hydrogen, hydrochloric acid, sulfuric acid, sulfonic acid, etc., PF
  • Lewis acids such as FeCl
  • halogens such as iodine 3
  • Atoms metal atoms such as sodium and potassium can be doped. This can be achieved by bringing these gases into contact with the semiconductor layer, immersing them in a solution, or applying an electrochemical doping treatment. These dopings can be added at the time of synthesizing the material, after the formation of the film, or added to the solution in the process of preparation from the solution, or added at the stage of the precursor film. It is also possible to co-deposit materials to be added at the time of vapor deposition, to mix them in the atmosphere at the time of film formation, or to accelerate ions in a vacuum and collide with the film to dobing.
  • These doping effects include changes in electrical conductivity due to increase or decrease in carrier density, changes in carrier polarity (P-type, n-type), changes in Fermi level, and the like. Such doping is often used in semiconductor devices.
  • Forming the protective layer 7 on the semiconductor layer has the advantage that the influence of outside air can be minimized and the electrical characteristics of the field effect transistor can be stabilized (see Fig. 2 (6)).
  • the above-mentioned materials are used as the protective layer material.
  • the film thickness of the protective layer 7 is a force that can adopt any film thickness depending on its purpose.
  • the protective layer is made of a resin
  • a method in which a resin solution is applied and then dried to form a resin film or a method in which a resin is applied or vapor deposited and then polymerized is exemplified. Perform cross-linking treatment after film formation May be.
  • the protective layer also has inorganic strength, for example, a formation method using a vacuum process such as a sputtering method or a vapor deposition method, or a formation method using a solution process such as a sol-gel method can be used.
  • a protective layer can be provided between the layers as needed, as well as on the semiconductor layer. These layers help to stabilize the electrical properties of the field effect transistor.
  • an organic material is mainly used as a semiconductor material, it can be manufactured in a relatively low temperature process. Accordingly, flexible materials such as plastic plates and plastic films that could not be used under conditions exposed to high temperatures can be used as the substrate. As a result, it is possible to manufacture a light, flexible, and hard-to-break element, and it can be used as a switching element for an active matrix of a display.
  • the display include a liquid crystal display, a polymer dispersion type liquid crystal display, an electrophoretic display, an EL display, an electochromic display, a particle rotation type display, and the like.
  • the field effect transistor of the present invention can be manufactured by a coating method or a printing process, it is also suitable for manufacturing a large area display.
  • the field effect transistor of the present invention is an ambipolar type, it is expected that a CMOS circuit can be easily formed. Normally, patterning N-type and P-type semiconductor materials separately makes it possible to fabricate CMOS circuits, which complicates the manufacturing process and increases costs. However, it is believed that the field effect transistor of the present invention can greatly reduce the cost.
  • the CMOS circuit formed by the field effect transistor of the present invention can also be used as a digital element or an analog element such as a memory circuit element, a signal driver circuit element, or a signal processing circuit element. Furthermore, by combining these, IC cards and IC tags can be manufactured. Furthermore, since the field effect transistor of the present invention can change its characteristics by external stimuli such as chemical substances, it can be used as an FET sensor.
  • the operational characteristics of the field effect transistor include the carrier mobility, conductivity, and insulating layer of the semiconductor layer. Capacitance, element configuration (distance and width between source and drain electrodes, film thickness of insulating layer, etc.). As the material for semiconductors used in field effect transistors, the higher the carrier mobility, the better.
  • a field effect characterized by having at least one compound represented by formula (1), formula (2) or formula (3) in the present invention and an electron transport semiconductor material.
  • Transistors exhibit high mobility in the atmosphere and have ambipolar characteristics.
  • each material has a layered structure that exhibits higher mobility and higher stability in the atmosphere than a single-layered state.
  • the field effect transistor of the present invention exhibits a stable ambipolar characteristic with little deterioration over a long period of time.
  • the field effect transistor of the present invention can produce an inexpensive semiconductor circuit without going through a complicated manufacturing process, and also has an electronic circuit having stable electrical characteristics over a long period of time and having a high stability and a long lifetime.
  • Synthesis Example 3 With reference to non-patent literature SYZherdeva et al.Zh.Organi.Khimi, 1980, 16,430, synthesis of 1 to 4 was carried out as follows. The commercially available compound 1 was quantitatively converted to 2 by heating in chlorosulfonic acid. Subsequently, 2 was suspended in acetic acid, 55% hydroiodic acid was added and heated, the resulting precipitate was filtered once, and the precipitate was mixed with bromine in acetic acid again and heated to 3 As a precipitate. Further, 3 and flaky tin were added to acetic acid and heated, and concentrated hydrochloric acid was gradually added to obtain 4 as a white precipitate.
  • a resist material was applied onto a wafer (surface resistance of 0.02 ⁇ 'cm or less), exposed to patterning, and chromium was deposited to 1 nm and gold was further deposited to 40 nm.
  • the resist was peeled off to form a source electrode (1) and a drain electrode (3) (a comb electrode having a channel length of 25 m ⁇ channel width of 4 mm ⁇ 19).
  • the silicon wafer provided with this electrode was placed in a vacuum vapor deposition apparatus and evacuated until the degree of vacuum in the apparatus became 1.0 X 10 _3 Pa or less. Resistance heating By vapor deposition, Compound No.
  • the thermal acid film in the n-doped silicon wafer with the thermal acid film has the function of the insulating layer (4), and the n-doped silicon wafer is It has the functions of the substrate (6) and the gate layer (5) (see Fig. 3).
  • the obtained field-effect transistor is placed in a vacuum professional bar, depressurized to about 5 X 10_ 3 Pa by a vacuum pump, and semiconductor characteristics are measured using a semiconductor parameter analyzer 4155C (Agilent). did.
  • the gate voltage was scanned from 10V to 100V in 10V steps, the drain voltage was scanned from 10V to 100V, and the drain current drain voltage was measured. As a result, current saturation was observed, and the hole mobility obtained from the saturation region force was 0.10 cm 2 ZVs.
  • the gate voltage was scanned from -10V to 100V in 10V steps, the drain voltage was scanned from 10V to 100V, and the drain current drain voltage was measured.
  • the electron mobility obtained from the saturation region force was 0.10 cm 2 ZVs, and the manifestation of unpolar characteristics was observed.
  • the hole mobility is 1.6 X 10 _2 cm 2 ZV ' S and the electron mobility is 5.9 X 10 _4 cm 2 ZV' s. showed that.
  • a field effect transistor of the present invention was produced in the same manner as in Example 1, except that Compound No. 34 was changed to Compound No. 1 (see Formula (4) and Table 1) in Example 1. .
  • As a result of measuring the semiconductor characteristics current saturation was observed.
  • the voltage current curve obtained, the device showed the property of Ann Neu polar type, the hole mobility is 0. 10cmVv- s, electron mobility was 0. 17cm 2 ZV 's.
  • the hole mobility is 1.2 X 10 _2 cm 2 / V 's and the electron mobility is 1.2 X 10 _3 cm 2 / V' s. showed that.
  • Example 1 Compound No. 34 (see Formula (4) and Table 1) as a semiconductor layer (2) was formed to a thickness of 30 ⁇ m, and then a co-evaporated layer of C60 fullerene and CuPc (l: l) was formed to a thickness of 10 nm. Thickness In addition to Example 1 except that C60 was further deposited to a thickness of 20 nm and 2,9-dimethylenole 4,7-diphenolone 1,10-phenanthroline was deposited to a thickness of lOnm at room temperature (25 ° C). Similarly, the field effect transistor of the present invention was produced. As a result of measuring semiconductor characteristics in the atmosphere, current saturation was observed. From the obtained voltage-current curve, this device exhibits the characteristics of an ambipolar type, whose hole mobility is 1.2 X 10 _1 cm 2 ZV 's and electron mobility is 7.0 X 10 cm ZV'. 7 s at s.
  • Example 1 Compound No. 1 (see Formula (4) and Table 1) as the semiconductor layer (2) is 10 ⁇ m thick, then C60 is lOnm thick, and Compound No. 1 is 60 nm thick.
  • a field-effect transistor of the present invention was produced in the same manner as in Example 1 except that deposition was performed at a room temperature (25 ° C). As a result of measuring the semiconductor characteristics, current saturation was observed, and from the obtained voltage current curve, this device showed the characteristics of an ambipolar type, and its hole mobility was 5.8 X 10 " 2 cmVv- s, electron mobility was 0.25 cm 2 ZV 's.
  • a field effect transistor of the present invention was produced in the same manner as in Example 1, except that Compound No. 34 was changed to Compound No. 152 (see Formula (6) and Table 3) in Example 1. .
  • As a result of measuring the semiconductor characteristics current saturation was observed, and from the obtained voltage-current curve, the device showed an unpolar characteristic, and its hole mobility was 8.5 X 10 " 4 cmVv- s, electron mobility was 6.6 X 10 _2 cm 2 ZV ' S.
  • the hole mobility when the same element was measured in the atmosphere was 2.5 X 10 _4 cm 2 / V' s.
  • the electron mobility was 6.1 x 10 " 4 cmVv-s.
  • Example 1 As the semiconductor layer (2), Compound No. 34 (see Formula (4) and Table 1) was formed to a thickness of 30 nm, then C60 was formed to a thickness of 30 nm, and 2, 9-dimethylene 4, A field effect transistor according to the present invention was produced in the same manner as in Example 1 except that 7-diphenyl-l, 10-phenant port phosphorus was deposited to a thickness of 30 nm at room temperature (25 ° C.). As a result of measuring the semiconductor characteristics, current saturation was observed, and from the obtained voltage-current curve, this device showed an ambipolar type characteristic, and its hole mobility was 9.4 X 10 " 2 cmVv-s The electron mobility is 0.14. cm 2 ZV's. In addition, when the same element is measured in the atmosphere, the hole mobility is 2. OX 10 _2 cm 2 / V 's and the electron mobility is 2. OX 10 _2 cm 2 / V' s. It was.
  • N-doped silicon wafer with 300nm SiO thermal oxide film surface resistance 0.02 ⁇ 'cm or less
  • Compound No. 34 (see formula (4) and Table 1) was deposited to a thickness of 15 nm and then C60 fullerene was deposited to a thickness of 40 nm at room temperature (25 ° C) by resistance heating vapor deposition. 2) formed. Subsequently, after the mask was set up for electrode fabrication, gold electrodes (source and drain electrodes: channel length 100 m X channel width 2 mm) were deposited to a thickness of 40 nm by resistance heating vapor deposition. An effect transistor was obtained.
  • the field effect transistor in this example is a top contact type, and the thermal oxide film in the n-doped silicon wafer with the thermal oxide film has the function of the insulator layer (4), and the n-doped silicon wafer is the substrate (6 ) And the gate electrode (5) function (see FIG. 1B).
  • the resulting field-effect transistor was placed in a vacuum pro one bar, the pressure was reduced to about 5 X 1 0_ 3 Pa by a vacuum pump, was measured use, semiconductor characteristics Te a semiconductor parameter analyzer 4155C (manufactured by Agilent Co.).
  • semiconductor characteristics Te a semiconductor parameter analyzer 4155C (manufactured by Agilent Co.).
  • the gate voltage was scanned from 10V to 60V in 10V steps, the drain voltage was scanned from 10V to 60V, and the drain current and drain voltage were measured.
  • the hole mobility obtained from the saturation region was 0.13 cm 2 ZVs, and the threshold voltage was –33 V.
  • the gate voltage was scanned from -10V to 60V in 10V steps, the drain voltage was scanned from -10V to 60V, and the drain current and drain voltage were measured.
  • current saturation was observed, the electron mobility obtained from the saturation region was 2.95 cm Vs, the threshold voltage was 37 V, and the manifestation of ambipolar characteristics was observed.
  • a field effect transistor of the present invention was produced in the same manner as in Example 7 except that the film thickness of Compound No. 34 was changed to 60 nm in Example 7.
  • the obtained field effect transistor was placed in a vacuum process bar, and the semiconductor characteristics were measured in the same manner.
  • current saturation The hole mobility obtained from the saturation region force was 0.15 cm Vs, and the electron mobility was 1.03 cm 2 ZVs.
  • the wafer (surface resistance 0.02 ⁇ 'cm or less) was placed in a vacuum deposition apparatus and evacuated until the degree of vacuum in the apparatus was 1.0 X 10 _3 Pa or less.
  • Compound No. 1 52 (see formula (6) and Table 3) was deposited to a thickness of 40 nm, then C60 fullerene was deposited to a thickness of 40 nm at room temperature (25 ° C).
  • a semiconductor layer (2) was formed.
  • gold electrodes source and drain electrodes: channel length 50 mX channel width 2 mm
  • the field effect transistor in this example is a top contact type, and the thermal oxide film in the n-doped silicon wafer with the thermal oxide film has the function of the insulator layer (4), and the n-doped silicon wafer is the substrate (6 ) And the gate electrode (5) function (see Figure 1-B).
  • the obtained field effect transistor was placed in a vacuum professional bar, and the semiconductor characteristics under the atmosphere were measured.
  • the gate voltage was scanned from 10V to -100V in 20V steps, the drain voltage was scanned from 10V to 100V, and the drain current and drain voltage were measured.
  • the hole mobility obtained from the saturation region was 0.23 cm Vs, and the threshold voltage was -45V.
  • the gate voltage was scanned from -10V to 100V in 20V steps, the drain voltage was scanned from -10V to 100V, and the drain current drain voltage was measured.
  • the electron mobility obtained from the saturation region was 0.21 cm 2 ZVs
  • the threshold voltage was 34 V
  • the expression of ambipolar characteristics was observed.
  • a field effect transistor having a specific organic heterocyclic compound and an electron transport semiconductor material according to the present invention has a practical level of charge mobility and excellent stability in the atmosphere. It can be widely used as a type field effect transistor.
  • FIG. 1 is a schematic view showing an example of a structural embodiment of a field effect transistor of the present invention.
  • FIG. 2 is a schematic view of a process for producing an embodiment of the field effect transistor of the present invention.
  • FIG. 3 is a schematic view of the field effect transistor of the present invention obtained in Example 1.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Thin Film Transistor (AREA)
  • Junction Field-Effect Transistors (AREA)

Abstract

L'invention concerne un transistor à effet de champ caractérisé en ce qu'il comprend au moins un composé représenté par la formule (1), (2) ou (3) ci-dessous, et un matériau semiconducteur transporteur d'électrons. (1) (2) (3) (Dans les formules, X1 à X6 représentent un atome de soufre, un atome de sélénium ou un atome de tellure, et R1 à R6 représentent indépendamment un groupe aromatique facultativement substitué).
PCT/JP2007/053092 2006-03-31 2007-02-20 Transistor a effet de champ WO2007125671A1 (fr)

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Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0364737A (ja) * 1989-08-02 1991-03-20 Sharp Corp 液晶表示装置
JP2009246140A (ja) * 2008-03-31 2009-10-22 Hiroshima Univ 発光素子
JP2009267132A (ja) * 2008-04-25 2009-11-12 Mitsui Chemicals Inc 有機トランジスタ
JP2010010549A (ja) * 2008-06-30 2010-01-14 Konica Minolta Holdings Inc 薄膜トランジスタの製造方法及び薄膜トランジスタ
JP2010016037A (ja) * 2008-07-01 2010-01-21 Konica Minolta Holdings Inc 薄膜トランジスタの製造方法
WO2010058833A1 (fr) * 2008-11-21 2010-05-27 国立大学法人広島大学 Nouveau composé hétérocyclique et utilisation de celui-ci
DE102010031897A1 (de) 2010-07-21 2012-01-26 Heraeus Clevios Gmbh Halbleiter auf Basis substituierter [1] Benzothieno[3,2-b][1]-benzothiophene
JP5370771B2 (ja) * 2007-05-24 2013-12-18 日本化薬株式会社 芳香族化合物の製造方法
JP2014033194A (ja) * 2012-07-13 2014-02-20 Semiconductor Energy Lab Co Ltd 半導体装置
JP2015053497A (ja) * 2011-03-10 2015-03-19 国立大学法人東京工業大学 有機半導体材料
JP2016105502A (ja) * 2008-07-16 2016-06-09 シーブライト・インコーポレイテッドＣｂｒｉｔｅ Ｉｎｃ． 金属酸化物半導体装置および半導体装置を製造する方法
JP2016136638A (ja) * 2010-01-22 2016-07-28 株式会社半導体エネルギー研究所 半導体装置
JP2016189476A (ja) * 2010-05-20 2016-11-04 株式会社半導体エネルギー研究所 半導体装置の作製方法
WO2017159025A1 (fr) * 2016-03-15 2017-09-21 ソニー株式会社 Élément de conversion photoélectrique et dispositif de prise d'image à semi-conducteurs
CN110862402A (zh) * 2018-08-28 2020-03-06 三星电子株式会社 化合物、有机薄膜、薄膜晶体管和电子器件
CN112992968A (zh) * 2015-07-17 2021-06-18 索尼公司 光电转换元件、图像拾取元件、层叠型图像拾取元件和固态图像拾取装置
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Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5487655B2 (ja) * 2008-04-17 2014-05-07 株式会社リコー ［１］ベンゾチエノ［３，２‐ｂ］［１］ベンゾチオフェン化合物およびその製造方法、それを用いた有機電子デバイス
KR101581065B1 (ko) * 2008-04-24 2015-12-29 메르크 파텐트 게엠베하 전자 디바이스
TWI394306B (zh) * 2008-08-26 2013-04-21 Univ Nat Chiao Tung 光電記憶體元件、其製造以及量測方法
US11066418B2 (en) 2018-11-26 2021-07-20 Samsung Electronics Co., Ltd. Compound and thin film transistor and electronic device

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005154371A (ja) * 2003-11-27 2005-06-16 Japan Science & Technology Agency 新規なベンゾジカルコゲノフェン誘導体、その製造方法およびそれを用いた有機半導体デバイス

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6278127B1 (en) * 1994-12-09 2001-08-21 Agere Systems Guardian Corp. Article comprising an organic thin film transistor adapted for biasing to form a N-type or a P-type transistor
JP2007273594A (ja) * 2006-03-30 2007-10-18 Nippon Kayaku Co Ltd 電界効果トランジスタ

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005154371A (ja) * 2003-11-27 2005-06-16 Japan Science & Technology Agency 新規なベンゾジカルコゲノフェン誘導体、その製造方法およびそれを用いた有機半導体デバイス

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHIKADA Y. ET AL.: "Benzo Selenophene Kokkaku o Kiban toshiba Shinki Yuki FET Zairyo no Kaihatsu", CSJ: THE CHEMICAL SOCIETY OF JAPAN KOEN YOKOSHU, vol. 85TH, no. 1, 11 March 2005 (2005-03-11), pages 500 + ABSTR. NO. 3H7-41, XP003018917 *
EBATA H. ET AL.: "[1]Benzothieno[2,3-b]Benzothiophene Yudotai no Gosei to Sono FET Tokusei", CSJ: THE CHEMICAL SOCIETY OF JAPAN KOEN YOKOSHU, vol. 86TH, no. 1, 11 March 2006 (2006-03-11), pages 561, XP003018937 *
EBATA H. ET AL.: "Denshi Kyuinsei Chikanki o Donyu shita Benzo [1,2-b:4,5-b'] Dichalcogenophene Yudotai no FET Tokusei", CSJ: THE CHEMICAL SOCIETY OF JAPAN KOEN YOKOSHU, vol. 85TH, no. 1, 11 March 2005 (2005-03-11), pages 500 *

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JPH0364737A (ja) * 1989-08-02 1991-03-20 Sharp Corp 液晶表示装置
JP5370771B2 (ja) * 2007-05-24 2013-12-18 日本化薬株式会社 芳香族化合物の製造方法
JP2009246140A (ja) * 2008-03-31 2009-10-22 Hiroshima Univ 発光素子
JP2009267132A (ja) * 2008-04-25 2009-11-12 Mitsui Chemicals Inc 有機トランジスタ
JP2010010549A (ja) * 2008-06-30 2010-01-14 Konica Minolta Holdings Inc 薄膜トランジスタの製造方法及び薄膜トランジスタ
JP2010016037A (ja) * 2008-07-01 2010-01-21 Konica Minolta Holdings Inc 薄膜トランジスタの製造方法
JP2016105502A (ja) * 2008-07-16 2016-06-09 シーブライト・インコーポレイテッドＣｂｒｉｔｅ Ｉｎｃ． 金属酸化物半導体装置および半導体装置を製造する方法
US8313671B2 (en) 2008-11-21 2012-11-20 Hiroshima University Heterocyclic compound and use thereof
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WO2010058833A1 (fr) * 2008-11-21 2010-05-27 国立大学法人広島大学 Nouveau composé hétérocyclique et utilisation de celui-ci
US9865744B2 (en) 2010-01-22 2018-01-09 Semiconductor Energy Laboratory Co., Ltd. Semiconductor device
JP2016136638A (ja) * 2010-01-22 2016-07-28 株式会社半導体エネルギー研究所 半導体装置
US9780229B2 (en) 2010-05-20 2017-10-03 Semiconductor Energy Laboratory Co., Ltd. Method for manufacturing semiconductor device
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WO2012010292A1 (fr) 2010-07-21 2012-01-26 Heraeus Clevios Gmbh Semi-conducteurs basés sur des [1]benzothiéno[3,2-b]-[1]-benzothiophènes substitués
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US10937964B2 (en) 2011-03-10 2021-03-02 Tokyo Institute Of Technology Organic semiconductor material
JP2015053497A (ja) * 2011-03-10 2015-03-19 国立大学法人東京工業大学 有機半導体材料
US10056557B2 (en) 2011-03-10 2018-08-21 Tokyo Institute Of Technology Organic semiconductor material
JP2014033194A (ja) * 2012-07-13 2014-02-20 Semiconductor Energy Lab Co Ltd 半導体装置
CN112992968A (zh) * 2015-07-17 2021-06-18 索尼公司 光电转换元件、图像拾取元件、层叠型图像拾取元件和固态图像拾取装置
US11398605B2 (en) 2016-03-15 2022-07-26 Sony Corporation Photoelectric conversion element and solid-state imaging device
JPWO2017159684A1 (ja) * 2016-03-15 2019-03-14 ソニー株式会社 光電変換素子および固体撮像装置
WO2017159025A1 (fr) * 2016-03-15 2017-09-21 ソニー株式会社 Élément de conversion photoélectrique et dispositif de prise d'image à semi-conducteurs
WO2017159684A1 (fr) * 2016-03-15 2017-09-21 ソニー株式会社 Élément de conversion photoélectrique et dispositif d'imagerie à l'état solide
JP7107217B2 (ja) 2016-03-15 2022-07-27 ソニーグループ株式会社 光電変換素子および固体撮像装置
JP2022130690A (ja) * 2016-03-15 2022-09-06 ソニーグループ株式会社 光電変換素子および固体撮像装置
CN110862402A (zh) * 2018-08-28 2020-03-06 三星电子株式会社 化合物、有机薄膜、薄膜晶体管和电子器件
KR20200024609A (ko) * 2018-08-28 2020-03-09 삼성전자주식회사 화합물, 박막 트랜지스터 및 전자 소자
US11450810B2 (en) 2018-08-28 2022-09-20 Samsung Electronics Co., Ltd. Compound and thin film transistor and electronic device
KR102631401B1 (ko) * 2018-08-28 2024-01-29 삼성전자주식회사 화합물, 박막 트랜지스터 및 전자 소자
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