WO2012118174A1 - Transistor organique à effet de champ et matière de semi-conducteur organique - Google Patents

Transistor organique à effet de champ et matière de semi-conducteur organique Download PDF

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WO2012118174A1
WO2012118174A1 PCT/JP2012/055339 JP2012055339W WO2012118174A1 WO 2012118174 A1 WO2012118174 A1 WO 2012118174A1 JP 2012055339 W JP2012055339 W JP 2012055339W WO 2012118174 A1 WO2012118174 A1 WO 2012118174A1
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semiconductor material
organic semiconductor
effect transistor
field effect
organic
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Japanese (ja)
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和男 瀧宮
安達　千波矢
池田　征明
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Kyushu University NUC
Nippon Kayaku Co Ltd
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Kyushu University NUC
Nippon Kayaku Co Ltd
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Priority to JP2013502411A priority Critical patent/JP5840197B2/ja
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • 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]
    • H10K10/484—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
    • H10K10/486—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions the channel region comprising two or more active layers, e.g. forming pn heterojunctions

Definitions

  • the present invention relates to an organic field effect transistor. More specifically, the present invention relates to an organic field effect transistor having a semiconductor active layer made of an organic semiconductor material having a specific structure and an organic semiconductor material having a structure different from that of the organic semiconductor material. More particularly, the present invention relates to an organic field effect transistor in which a semiconductor active layer has a stacked structure of a layer containing an organic semiconductor material having a specific structure and a layer containing an organic semiconductor material different from the organic 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, and a gate electrode or the like via these electrodes and an insulator layer.
  • inorganic semiconductor materials centered on silicon, particularly amorphous silicon, are used for field effect transistors.
  • Thin film transistors manufactured using these semiconductor materials on a substrate such as glass are used for displays and the like, used as integrated circuits as logic circuit elements, and widely used as switching elements.
  • studies have been actively conducted on the use of inorganic oxide semiconductors as semiconductor materials.
  • field effect transistors using organic semiconductor materials that do not require high-temperature treatment during the manufacture of field effect transistors have also been developed. If an organic semiconductor material can be used, manufacturing by a low-temperature process becomes possible, and the range of usable substrate materials is expanded. As a result, it becomes possible to manufacture a field effect transistor that is more flexible, lightweight, and less likely to break. In the field effect transistor manufacturing process, a large-area field effect transistor may be manufactured at low cost by applying a solution containing an organic semiconductor material, a printing method using an inkjet, or the like.
  • Non-patent Document 1 Patent Document 1, Patent Document 1, and Patent Document 2
  • improvement of atmospheric stability brings problems such as lower mobility and lowering characteristics of electrification and injection from the electrode.
  • Patent Document 3 Patent Document 4, Non-Patent Document 2, Non-Patent Document 3
  • Studies have been made to improve transistor characteristics by stacking organic semiconductor layers.
  • Non-Patent Document 4 uses pentacene as a rubrene crystallinity control material
  • Non-Patent Document 5 uses pentacene as a benzodithiophene dimer crystallinity control material to increase crystallinity and transfer rubrene and benzothiophene dimer. The degree is improved.
  • An object of the present invention is to provide a practical field effect transistor having practical stability and excellent semiconductor characteristics such as carrier mobility, hysteresis and threshold stability.
  • the present inventors have found a novel compound having a specific structure useful for a semiconductor active layer, and organic semiconductor materials and other structures having a specific structure for the semiconductor active layer It has been found that an organic field effect transistor having a high charge transfer speed and excellent stability can be obtained by combining organic semiconductor materials having the above, and the present invention has been completed.
  • a field effect transistor comprising an organic semiconductor material (A) represented by the general formula (1) and an organic semiconductor material (B) other than the organic semiconductor material represented by the general formula (1).
  • X 1 represents an aliphatic hydrocarbon residue which may have a substituent or an aromatic residue which may have a substituent.
  • R 1 represents a hydrogen atom or an aliphatic hydrocarbon residue which may have a substituent.
  • a layer containing the organic semiconductor material (B) and a layer containing the organic semiconductor material (A) are sequentially stacked, and further a layer containing the organic semiconductor material (A)
  • the field effect transistor according to [6] which has a top contact bottom gate structure in which a source electrode and a drain electrode are respectively provided so as to be in contact with the uppermost portion.
  • a source electrode and a drain electrode are respectively provided on a substrate, and a layer containing an organic semiconductor material (A) and a layer containing an organic semiconductor material (B) are sequentially stacked thereon, and an organic semiconductor material ( [6]
  • the field effect transistor according to [6] which has a bottom contact top gate structure in which a gate electrode is provided on an insulator layer provided so as to be in contact with the top of the layer including B).
  • R 3 represents a C1-3 alkyl group.
  • a naphthodithiophene-based organic semiconductor material comprising the compound according to any one of [9] to [11].
  • a naphthodithiophene-based organic transistor material comprising the compound according to any one of [9] to [11].
  • a field effect transistor comprising the organic semiconductor material according to [12].
  • An organic field effect transistor having a high charge transfer speed and excellent stability can be obtained by combining an organic semiconductor material and an organic semiconductor material having a specific structure with the semiconductor active layer.
  • the present invention combines a heteroacene P-type organic semiconductor material represented by the general formula (1) and a P-type organic semiconductor material different from the heteroacene P-type organic semiconductor material represented by the general formula (1) in the semiconductor active layer.
  • a heteroacene P-type organic semiconductor material represented by the general formula (1) and a P-type organic semiconductor material different from the heteroacene P-type organic semiconductor material represented by the general formula (1) in the semiconductor active layer.
  • the organic semiconductor material (A) represented by the general formula (1) can have a substituent (in the formula (1), the substituent is represented by X 1 ).
  • the substituent include an aliphatic hydrocarbon residue which may be substituted or an aromatic residue which may be substituted.
  • examples of the aliphatic hydrocarbon group include a saturated or unsaturated linear, branched or cyclic aliphatic hydrocarbon group, preferably a linear or branched aliphatic hydrocarbon group, and more preferably It is a linear aliphatic hydrocarbon group.
  • the number of carbon atoms is usually C1-C36, preferably C1-C24, more preferably C1-C20, and most preferably C1-C12.
  • This aliphatic hydrocarbon group may be substituted with a halogen atom.
  • Specific examples of the linear or branched saturated aliphatic hydrocarbon group include methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, t-butyl, n-pentyl, iso-pentyl, t- Pentyl, sec-pentyl, n-hexyl, iso-hexyl, n-heptyl, sec-heptyl, n-octyl, n-nonyl, sec-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradec
  • cyclic saturated aliphatic hydrocarbon group examples include cyclohexyl, cyclopentyl, adamantyl, norbornyl and the like.
  • linear or branched unsaturated aliphatic hydrocarbon group examples include vinyl, allyl, eicosadienyl, 11,14-eicosadienyl, and geranyl (trans-3,7-dimethyl-2,6-octadien-1-yl).
  • Farnesyl trans, trans-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl
  • 4-pentenyl 1-propynyl, 1-hexynyl, 1-octynyl, 1-decynyl, 1 -Undecynyl, 1-dodecynyl, 1-tetradecynyl, 1-hexadecynyl, 1-nonadecynyl and the like.
  • linear or branched aliphatic hydrocarbon groups preferred are linear or branched aliphatic hydrocarbon groups, and more preferred are linear aliphatic hydrocarbon groups.
  • the saturated or unsaturated aliphatic hydrocarbon group includes a saturated alkyl group, an alkenyl group containing a carbon-carbon double bond, and an alkynyl group containing a carbon-carbon triple bond, more preferably an alkyl group or an alkynyl group. And more preferably an alkyl group.
  • the aliphatic hydrocarbon residue is a combination of these saturated or unsaturated aliphatic hydrocarbon groups, that is, a carbon-carbon double bond and a carbon-carbon triple bond are simultaneously formed at a site in the aliphatic hydrocarbon group.
  • the aliphatic hydrocarbon residue may be substituted with a halogen atom, and examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, preferably a fluorine atom, a chlorine atom, a bromine atom, Preferred are a fluorine atom and a bromine atom.
  • aromatic residue examples include an aromatic hydrocarbon group such as phenyl group, naphthyl group, anthryl group, phenanthryl group, pyrenyl group, benzopyrenyl group, pyridyl group, pyrazyl group, pyrimidyl group, quinolyl group, Heterocyclic groups such as isoquinolyl group, pyrrolyl group, indolenyl group, imidazolyl group, carbazolyl group, thienyl group, furyl group, pyranyl group, pyridonyl group, etc.
  • a cyclic group is mentioned. Of these, preferred are a phenyl group, a naphthyl group, a pyridyl group, and a thienyl group.
  • Examples of the substituent that can be possessed by the aromatic residue include, but are not limited to, the aliphatic hydrocarbon group and the halogen atom. Among them, an aliphatic hydrocarbon group is preferable, a C1-C3 lower alkyl group such as methyl, ethyl, iso-propyl, etc. is more preferable, and a methyl group is most preferable.
  • R 1 represents a hydrogen atom or an aliphatic hydrocarbon residue which may have a substituent.
  • the aliphatic hydrocarbon residue may be the same as the aliphatic hydrocarbon residue described above, and is preferably a C1-C3 lower alkyl group such as methyl, ethyl, iso-propyl, and the like is most preferably a methyl group. preferable.
  • Examples of the organic semiconductor material (B) other than the organic semiconductor material represented by the general formula (1) include pentacene, phthalocyanine, oligothiophene, benzothiophene, anthrathiophene, and benzothienobenzothiophene heteroacene organic semiconductor materials. Can be mentioned. Among them, a benzothienobenzothiophene derivative represented by the general formula (3) is preferable.
  • X 2 represents an aliphatic hydrocarbon residue which may have a substituent or an aromatic residue which may have a substituent. X 2 shown here can be the same as X 1 described above.
  • R 2 represents a hydrogen atom or an aliphatic hydrocarbon residue which may have a substituent.
  • the aliphatic hydrocarbon residue may be the same as the aliphatic hydrocarbon residue described above.
  • the method for producing the organic semiconductor material (A) represented by the formula (1) can be represented by, for example, the method described in Patent Document 5, that is, the following reaction formula.
  • bromination is repeated using 2,6-dihydroxynaphthalene as a starting material to obtain a tetrabromo compound, which is then dehalogenated using tin, and subsequently trifluoromethanesulfonic acid anhydride is allowed to act.
  • a precursor dibromo-diethynylnaphthalene derivative can be obtained by reacting this compound with a corresponding acetylene derivative in an aprotic polar solvent in the presence of a palladium catalyst or the like.
  • a sulfide salt such as sodium sulfide hydrate
  • the purification method of the compound is not particularly limited, and known methods such as recrystallization, column chromatography, and vacuum sublimation purification can be employed. Moreover, you may use combining these methods as needed.
  • the compound represented by the general formula (3) can be obtained by the methods described in Patent Document 1 and Patent Document 6, for example.
  • FIG. 1 shows some embodiments of the field effect transistor (element) of the present invention.
  • 1 is a source electrode
  • 2 is a semiconductor layer
  • 3 is a drain electrode
  • 4 is an insulator layer
  • 5 is a gate electrode
  • 6 is a substrate.
  • positioning of each layer and an electrode can be suitably selected according to the use of an element.
  • a to D and F are called lateral FETs because current flows in a direction parallel to the substrate.
  • A is called a bottom gate bottom contact type structure, and B is called a top contact bottom gate type structure.
  • B ′ is a mode in which the semiconductor layer of B is divided into two, that is, two layers are stacked.
  • C is a top gate top contact type structure in which source and drain electrodes and an insulator layer are provided on a semiconductor and a gate electrode is formed thereon.
  • D is a structure called a bottom gate bottom & top contact type transistor.
  • E is a schematic diagram of an electrostatic induction transistor (SIT) which is an FET having a vertical structure. According to this SIT structure, a large amount of carriers can move at a time because the current flow spreads in a plane. Further, since the source electrode and the drain electrode are arranged vertically, the distance between the electrodes can be reduced, so that the response is fast. Therefore, it can be preferably applied to uses such as flowing a large current or performing high-speed switching.
  • F is a top gate bottom contact type
  • F ′ is an embodiment in which the semiconductor layer of F is divided into two, that is, two layers are stacked.
  • the substrate 6 needs to be able to hold each layer formed thereon without peeling off.
  • insulative materials such as resin film, paper, glass, quartz, ceramic, etc., materials in which an insulating layer is formed on a conductive substrate such as metal or alloy by coating, materials made of various combinations such as resin and inorganic materials, etc. are used Yes.
  • the resin film that can be used include polyethylene terephthalate, polyethylene naphthalate, polyethersulfone, polyamide, polyimide, polycarbonate, cellulose triacetate, polyetherimide, and the like.
  • the element can have flexibility, is flexible and lightweight, and improves practicality.
  • the thickness of the substrate is usually 1 ⁇ m to 10 mm, preferably 5 ⁇ m to 5 mm.
  • a conductive material is used for the source electrode 1, the drain electrode 3, and the gate electrode 5.
  • metals such as platinum, gold, silver, aluminum, chromium, tungsten, tantalum, nickel, cobalt, copper, iron, lead, tin, titanium, indium, palladium, molybdenum, magnesium, calcium, barium, lithium, potassium, sodium, etc.
  • conductive oxides such as InO 2 , ZnO 2 , SnO 2 , ITO
  • conductive polymer compounds such as polyaniline, polypyrrole, polythiophene, polyacetylene, polyparaphenylene vinylene, polydiacetylene
  • silicon, germanium Semiconductors such as gallium arsenide
  • carbon materials such as carbon black, fullerene, carbon nanotubes, and graphite can be used.
  • the conductive polymer compound or the semiconductor may be doped.
  • Examples of the dopant used in this case include acids such as hydrochloric acid, sulfuric acid, and sulfonic acid, Lewis acids such as PF 5 , AsF 5 , and FeCl 3 , halogen atoms such as iodine, and metal atoms such as lithium, sodium, and potassium. It is done.
  • 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, and a field effect transistor having good charge injection characteristics can be obtained.
  • a wiring is connected to each of the electrodes 1, 3, and 5, and the wiring is also made of the same material as the electrode.
  • An insulating material is used for the insulator layer 4.
  • polymers such as polyparaxylylene, polyacrylate, polymethyl methacrylate, polystyrene, polyvinylphenol, polyamide, polyimide, polycarbonate, polyester, polyvinyl alcohol, polyvinyl acetate, polyurethane, polysulfone, epoxy resin, phenol resin, fluorine resin, and the like Copolymers combining these; oxides such as silicon dioxide, aluminum oxide, titanium oxide, and tantalum oxide; ferroelectric oxides such as SrTiO 3 and BaTiO 3 ; nitrides such as silicon nitride and aluminum nitride; sulfides; A dielectric such as fluoride, or a polymer in which particles of these dielectrics are dispersed can be used.
  • the film thickness of the insulator layer 4 varies depending on the material, but is usually 0.1 nm to 100 ⁇ m, preferably 0.5 nm to 50 ⁇ m
  • the organic semiconductor material (A) represented by the general formula (1) can be used alone as the material of the semiconductor layer 2, the organic semiconductor material (A) represented by the general formula (1) and the general An organic semiconductor material (B) other than the organic semiconductor material represented by the formula (1) can also be used in combination.
  • the organic semiconductor material (A) and the organic semiconductor material (B) can be mixed and used, or a layer of the organic semiconductor material (A) and a layer of the organic semiconductor material (B) are laminated. It can also be used.
  • the material of the semiconductor layer may further contain components other than these components, but the total amount of the organic semiconductor material (A) and the organic semiconductor material (B) is 50 mass with respect to the total weight of the material.
  • the thickness of the semiconductor layer 2 is preferably as thin as possible without losing necessary functions. This is because staggered field effect transistors as shown in B and F require movement of charges in the film thickness direction, and leakage current may increase as the film thickness increases. In order to show a necessary function, it is usually 1 nm to 1 ⁇ m, preferably 5 nm to 500 nm, more preferably 10 nm to 300 nm.
  • the layer containing the organic semiconductor material (A) and the layer containing the organic semiconductor material (B) have a laminated structure, the total film thickness may be the same as described above. Each film thickness can be arbitrarily adjusted as long as necessary functions are not lost. A field effect transistor having good semiconductor characteristics can be obtained by adjusting the mixing ratio and film thickness of these materials.
  • 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 / OFF ratio of the element can be increased.
  • the electrical characteristics can be stabilized.
  • membrane which consists of various resins, such as acrylic resins, such as an epoxy resin and polymethylmethacrylate, polyurethane, polyimide, polyvinyl alcohol, a fluororesin, polyolefin, silicon oxide, aluminum oxide,
  • a film made of a dielectric such as an inorganic oxide film or a nitride film such as silicon nitride is preferably used.
  • a resin (polymer) having low oxygen and moisture permeability and water absorption is preferable.
  • protective materials developed for organic EL displays can also be used.
  • the protective layer can have any thickness depending on the purpose, but is usually 100 nm to 1 mm.
  • the substrate surface treatment controls the molecular orientation at the interface portion between the substrate and the semiconductor film formed thereafter, and improves characteristics such as carrier mobility.
  • substrate treatment examples include hydrophobization treatment with hexamethyldisilazane, cyclohexene, octadecyltrichlorosilane, acid treatment with hydrochloric acid, sulfuric acid, acetic acid, sodium hydroxide, potassium hydroxide, calcium hydroxide, ammonia, etc.
  • Electrical treatment such as alkali treatment with ozone, ozone treatment, fluorination treatment, plasma treatment with oxygen and argon, Langmuir / Blodgett film formation process, other insulator and semiconductor thin film formation process, mechanical process, corona discharge, etc. Examples thereof include rubbing treatment using treatment, fibers, and the like.
  • a vacuum deposition method for example, a vacuum deposition method, a sputtering method, a coating method, a printing method, a sol-gel method, or the like can be appropriately employed.
  • the substrate and substrate processing It is manufactured by providing necessary layers and electrodes on the substrate 6 (see FIG. 2 (1)). As the substrate, those described above can be used. It is also possible to perform the above-described surface treatment or the like 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 usually 1 ⁇ m to 10 mm, preferably 5 ⁇ m to 5 mm. Further, if necessary, the substrate may have an electrode function.
  • a gate electrode 5 is formed on the substrate 6 (see FIG. 2B).
  • the electrode material described above is used as the electrode material.
  • various methods can be used. 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 necessary so as to obtain a desired shape during or after film formation.
  • Various methods can be used as the patterning method, and examples thereof include a photolithography method in which patterning and etching of a photoresist are combined.
  • patterning can also be performed using a printing method such as ink jet printing, screen printing, offset printing, letterpress printing, or the like, a soft lithography technique such as a microcontact printing technique, and a technique combining a plurality of these techniques.
  • the film thickness of the gate electrode 5 varies depending on the material, but is usually 0.1 nm to 10 ⁇ m, preferably 0.5 nm to 5 ⁇ m, more preferably 1 nm to 3 ⁇ m. Moreover, when it serves as a gate electrode and a board
  • insulator layer 4 is formed over the gate electrode 5 (see FIG. 2 (3)).
  • the insulator material those described above are used.
  • Various methods can be used to form the insulator layer 4. For example, spin coating, spray coating, dip coating, casting, bar coating, blade coating and other coating methods, screen printing, offset printing, inkjet printing methods, vacuum deposition, molecular beam epitaxial growth, ion cluster beam method, ion plating Examples thereof include dry process methods such as a coating method, a sputtering method, an atmospheric pressure plasma method, and a CVD method.
  • a sol-gel method, alumite on aluminum, a method of forming an oxide film on a metal such as a thermal oxide film of silicon, or the like is employed.
  • a predetermined surface treatment can be performed on the insulator layer in order to satisfactorily orient the semiconductor molecules at the interface between the two layers.
  • the surface treatment method the same surface treatment as the substrate can be used.
  • the thickness of the insulator layer 4 is preferably as thin as possible without impairing its function. Usually, the thickness is 0.1 nm to 100 ⁇ m, preferably 0.5 nm to 50 ⁇ m, more preferably 5 nm to 10 ⁇ m.
  • Formation of semiconductor layer As the semiconductor material, the materials described above are used. Various methods can be used for forming the semiconductor layer. Formation method in vacuum process such as sputtering method, CVD method, molecular beam epitaxial growth method, vacuum deposition method, coating method such as dip coating method, die coater method, roll coater method, bar coater method, spin coating method, ink jet method In addition, it is roughly classified into formation methods in solution processes such as screen printing, offset printing, and microcontact printing. Hereinafter, a method for forming a semiconductor layer will be described in detail.
  • a method for obtaining a semiconductor layer by depositing a material by a vacuum process will be described.
  • a method vacuum deposition method in which the semiconductor material is heated in a crucible or a metal boat under vacuum and the evaporated semiconductor material is attached (deposited) to a substrate (exposed portions of the insulator layer, the source electrode and the drain electrode).
  • the degree of vacuum is usually 1.0 ⁇ 10 ⁇ 1 Pa or less, preferably 1.0 ⁇ 10 ⁇ 4 Pa or less.
  • the substrate temperature since the characteristics of the semiconductor film and hence the field effect transistor vary depending on the substrate temperature during vapor deposition, it is preferable to select the substrate temperature carefully.
  • the substrate temperature during vapor deposition is usually 0 to 200 ° C., preferably 10 to 150 ° C.
  • the deposition rate is usually 0.001 nm / second to 10 nm / second, preferably 0.01 nm / second to 1 nm / second.
  • each material is obtained by heating and evaporating and laminating 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 compound, such a vacuum process can be preferably used. Although such a vacuum process requires somewhat expensive equipment, there is an advantage that a uniform film can be easily obtained with good film formability.
  • This method is generally used in the case of an organic semiconductor material that is soluble in a solvent.
  • 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 micro contact printing methods.
  • the method of soft lithography, etc., or a method combining a plurality of these methods may be employed.
  • the thickness of the semiconductor layer formed by these methods is preferably thin as long as the function is not impaired. As the film thickness increases, the leakage current increases, and there is a concern that energy is required for the movement of charges in the film thickness direction.
  • the thickness of the semiconductor layer is usually 1 nm to 1 ⁇ m, preferably 5 nm to 500 nm, more preferably 10 nm to 300 nm.
  • a mixed film of semiconductor materials can be easily obtained by dissolving each material together and forming the film by the above process. However, in order to obtain a laminated structure, 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. When such a solution process is used for forming a semiconductor layer, there is an advantage that a large-area field effect transistor can be manufactured with relatively inexpensive equipment. It is also possible to form a film in combination, such as using a vacuum process after the solution process.
  • the characteristics of the semiconductor layer thus formed can be further improved by post-processing.
  • the heat treatment can relieve distortion in the film generated during film formation, and can improve and stabilize characteristics.
  • a change in characteristics due to oxidation or reduction can be induced by exposure to an oxidizing or reducing gas or liquid such as oxygen or hydrogen. This can be used for the purpose of increasing or decreasing the carrier density in the film, for example.
  • the source electrode 1 and the drain electrode 3 can be formed according to the method for forming the gate electrode 5 (see FIG. 2 (5)).
  • a vacuum deposition method using a shadow mask is generally used, and conversely, in the case of a bottom contact structure located under a semiconductor layer, photolithography or Electrode patterning is often formed using various printing methods.
  • the protective layer 7 on the semiconductor layer can be formed using various methods.
  • the protective layer is made of a resin, for example, a method in which a resin solution is applied and then dried to form a resin film, or a method in which a resin monomer is applied or vapor-deposited and then polymerized is exemplified. Cross-linking treatment may be performed after film formation.
  • the protective layer is made of an inorganic material, for example, a formation method in a vacuum process such as a sputtering method or a vapor deposition method, or a formation method in a solution process such as a sol-gel method can be used.
  • a protective layer can be provided between the layers as needed in addition to the semiconductor layer. These layers may contribute to stabilization of the electrical characteristics of the field effect transistor.
  • the operating characteristics of the field effect transistor are determined by the carrier mobility of the semiconductor layer, the capacitance of the insulating layer, the element configuration (distance and width between source and drain electrodes, etc.), and the like.
  • a semiconductor material used for the field effect transistor a material having higher carrier mobility when a semiconductor layer is formed is preferable.
  • the semiconductor layer of the field effect transistor of the present invention can contain a naphthodithiophene compound represented by the general formula (5) and also contains an organic semiconductor material (A) represented by the general formula (1). And a layer containing an organic semiconductor material (B) other than the organic semiconductor material represented by the general formula (1) can be stacked as a semiconductor layer.
  • the stacked field effect transistor is advantageous in that it is stable in the atmosphere and has a long lifetime.
  • the driving voltage is lowered, and the power consumption is reduced as compared with the conventional one, thereby enabling energy saving.
  • the barrier for charge injection from the electrode to the semiconductor film is reduced by lowering the threshold voltage, so that the durability of the semiconductor element and the semiconductor device having the semiconductor element itself is also improved, and the uniformity and reliability are increased.
  • a field effect transistor can be obtained.
  • Example 2 Synthesis of 3,7-dibromo-2,6-bis (3-tolylethynyl) naphthalene The same operation as in Example 1 was performed except that 3-ethynyltoluene was used instead of 4-ethynyltoluene to obtain 3,7-dibromo-2,6-bis (3-tolylethynyl) naphthalene as a yellow solid. (54%).
  • Example 4 Synthesis of 2,7-bis (3-tolyl) -naphtho [2,3-b: 7,6-b ′] dithiophene (compound (7)) The same procedure as in Example 3 except that 3,7-dibromo-2,6-bis (3-triethynyl) naphthalene was used instead of 3,7-dibromo-2,6-bis (4-tolylethynyl) naphthalene. To give 2,7-bis (3-tolyl) -naphtho [2,3-b: 7,6-b ′] dithiophene (46%).
  • Example 5 Production of Field Effect Transistor of Compound (6) (p-tolyl NDT) An n-doped silicon wafer with 200 nm SiO 2 thermal oxide film (surface resistance 0.02 ⁇ ⁇ cm or less) treated with octadecyltrichlorosilane was vacuum deposited. It was installed in the apparatus and evacuated until the degree of vacuum in the apparatus was 5.0 ⁇ 10 ⁇ 3 Pa or less. The compound (6) was vapor-deposited on the electrode at a substrate temperature of about 100 ° C. at a deposition rate of 1 to 2 liters / sec to a thickness of 50 nm by a resistance heating vapor deposition method to form a semiconductor layer (2).
  • a shadow mask for electrode preparation is attached to this substrate, and it is placed in a vacuum vapor deposition apparatus.
  • the vacuum in the apparatus is evacuated to 1.0 ⁇ 10 ⁇ 4 Pa or less, and a gold electrode is formed by resistance heating vapor deposition. That is, the source electrode (1) and the drain electrode (3) were deposited to a thickness of 40 nm to obtain a TC (top contact) type field effect transistor (channel length 50 ⁇ m, channel width 1.5 mm) of the present invention. .
  • the thermal oxide film in the n-doped silicon wafer with the thermal oxide film has the function of the insulating layer (4), and the n-doped silicon wafer is the substrate (6) and the gate electrode (5). ) (See FIG. 3).
  • the obtained field effect transistor was installed in a prober, and the semiconductor characteristics were measured using a semiconductor parameter analyzer 4200SCS (manufactured by Keithley). The semiconductor characteristics were such that the drain voltage was ⁇ 60 V, the gate voltage was scanned from 60 V to ⁇ 60 V, and the drain current-gate voltage (transfer) characteristics were measured. From the obtained voltage-current curve, the carrier mobility of the device was 1.31cm 2 / Vs, the threshold voltage is 48V, Ion / Ioff was 10 6.
  • Example 6 Production of Field Effect Transistor of Compound (7) (m-tolyl NDT) An n-doped silicon wafer with 200 nm SiO 2 thermal oxide film (surface resistance 0.02 ⁇ ⁇ cm or less) treated with octyltrichlorosilane was vacuum deposited. It was installed in the apparatus and evacuated until the vacuum in the apparatus was 5.0 ⁇ 10 ⁇ 3 Pa or less. The compound (7) was vapor-deposited on this electrode at a thickness of 50 nm at a vapor deposition rate of 1 to 2 liters / sec on this electrode at a substrate temperature of about 100 ° C. to form a semiconductor layer (2).
  • a shadow mask for electrode preparation is attached to this substrate, and it is placed in a vacuum vapor deposition apparatus.
  • the vacuum in the apparatus is evacuated to 1.0 ⁇ 10 ⁇ 4 Pa or less, and a gold electrode is formed by resistance heating vapor deposition. That is, the source electrode (1) and the drain electrode (3) were deposited to a thickness of 40 nm to obtain a TC (top contact) type field effect transistor (channel length 50 ⁇ m, channel width 1.5 mm) of the present invention. .
  • the obtained field effect transistor was installed in a prober, and the semiconductor characteristics were measured using a semiconductor parameter analyzer 4200SCS (manufactured by Keithley). The semiconductor characteristics were such that the drain voltage was ⁇ 60 V, the gate voltage was scanned from 20 V to ⁇ 60 V, and the drain current-gate voltage (transfer) characteristics were measured. From the obtained voltage-current curve, the carrier mobility of the device was 0.34 cm 2 / Vs, the threshold voltage is -2 V, Ion / Ioff was 10 5.
  • Example 7 Production of Stacked Field Effect Transistor of Compound (6) (p-tolyl NDT) and Compound (23) (DPh-BTBT) n-Doped Silicon Wafer with 200 nm SiO 2 Thermal Oxide Film Treated with Octyltrichlorosilane Treatment ( A surface resistance of 0.02 ⁇ ⁇ cm or less) was placed in a vacuum deposition apparatus, and evacuated until the degree of vacuum in the apparatus was 5.0 ⁇ 10 ⁇ 3 Pa or less. The compound (23) was deposited on this electrode at a thickness of 50 nm at a deposition rate of 1 to 2 cm / sec under the condition of a substrate temperature of about 25 ° C. by resistance heating deposition, and then the compound (6) was deposited to 1 to 2 cm / sec.
  • a semiconductor layer (2) was formed by vapor deposition to a thickness of 5 nm at a deposition rate of sec.
  • a shadow mask for electrode preparation is attached to this substrate, and it is placed in a vacuum vapor deposition apparatus.
  • the vacuum in the apparatus is evacuated to 1.0 ⁇ 10 ⁇ 4 Pa or less, and a gold electrode is formed by resistance heating vapor deposition. That is, the source electrode (1) and the drain electrode (3) are deposited to a thickness of 40 nm to obtain a field effect transistor (channel length 50 ⁇ m, channel width 1.5 mm) of the present invention which is a TC (top contact) type. It was.
  • the obtained field effect transistor was installed in a prober, and the semiconductor characteristics were measured using a semiconductor parameter analyzer 4200SCS (manufactured by Keithley). The semiconductor characteristics were such that the drain voltage was ⁇ 60 V, the gate voltage was scanned from 20 V to ⁇ 60 V, and the drain current-gate voltage (transfer) characteristics were measured. From the obtained voltage-current curve, the carrier mobility of the device was 3.1 cm 2 / Vs, the threshold voltage is -7V, Ion / Ioff was 10 7.
  • Example 8 Production of Stacked Field Effect Transistor of Compound (5) (DPh-NDT) and Compound (23) (DPh-BTBT) Example 7 except that compound (5) was used instead of compound (6) A field effect transistor was obtained by the same method.
  • a shadow mask for electrode preparation is attached to this substrate, and it is placed in a vacuum vapor deposition apparatus.
  • the vacuum in the apparatus is evacuated to 1.0 ⁇ 10 ⁇ 4 Pa or less, and a gold electrode is formed by resistance heating vapor deposition. That is, the source electrode (1) and the drain electrode (3) were deposited to a thickness of 40 nm to obtain a TC (top contact) type field effect transistor (channel length 50 ⁇ m, channel width 1.5 mm) of the present invention. .
  • the obtained field effect transistor was installed in a prober, and the semiconductor characteristics were measured using a semiconductor parameter analyzer 4200SCS (manufactured by Keithley). The semiconductor characteristics were such that the drain voltage was ⁇ 60 V, the gate voltage was scanned from 20 V to ⁇ 60 V, and the drain current-gate voltage (transfer) characteristics were measured. From the obtained voltage-current curve, the carrier mobility of this device was 0.8 cm 2 / Vs, the threshold voltage was ⁇ 24 V, and Ion / Ioff was 10 8 .
  • Example 9 A field effect transistor was produced in the same manner as in Example 7, Example 8, and Comparative Example 1 except that the channel length L (20, 40 ⁇ m) of the field effect transistor was changed, and the mobility was measured. The results are shown in Table 1.
  • Example 10 Production of Stacked Field Effect Transistor of Compound (6) (p-tolyl NDT) and Compound (20) (C8-BTBT) n-doped silicon wafer with 300 nm SiO 2 thermal oxide film subjected to HMDS treatment (surface resistance) 0.02 ⁇ ⁇ cm or less) was placed in a vacuum vapor deposition apparatus and evacuated until the degree of vacuum in the apparatus was 1.0 ⁇ 10 ⁇ 3 Pa or less.
  • compound (20) was deposited on this electrode at a substrate temperature of about 25 ° C. at a deposition rate of 1 ⁇ / sec to a thickness of 50 nm, and then compound (6) was deposited at 1-2 ⁇ / sec.
  • a semiconductor layer (2) was formed by vapor deposition to a thickness of 5 nm at a vapor deposition rate.
  • a shadow mask for electrode preparation is attached to this substrate, and it is placed in a vacuum vapor deposition apparatus.
  • the vacuum in the apparatus is evacuated to 5.0 ⁇ 10 ⁇ 4 Pa or less, and a gold electrode is formed by resistance heating vapor deposition. That is, the source electrode (1) and the drain electrode (3) are deposited to a thickness of 50 nm to obtain a field effect transistor (channel length 200 ⁇ m, channel width 2.5 mm) of the present invention which is a TC (top contact) type. It was.
  • the obtained field effect transistor was installed in a prober, and the semiconductor characteristics were measured using a semiconductor parameter analyzer 4200SCS (manufactured by Keithley). The semiconductor characteristics were such that the drain voltage was ⁇ 100 V, the gate voltage was scanned from 20 V to ⁇ 100 V, and the drain current-gate voltage (transfer) characteristics were measured. From the obtained voltage-current curve, the carrier mobility of this device was 10.5 cm 2 / Vs, the threshold voltage was ⁇ 43 V, and Ion / Ioff was 4 ⁇ 10 8 .
  • the obtained field effect transistor was installed in a prober, and the semiconductor characteristics were measured using a semiconductor parameter analyzer 4200SCS (manufactured by Keithley). The semiconductor characteristics were such that the drain voltage was ⁇ 100 V, the gate voltage was scanned from 20 V to ⁇ 100 V, and the drain current-gate voltage (transfer) characteristics were measured. From the obtained voltage-current curve, the carrier mobility of this device was 6.0 cm 2 / Vs, the threshold voltage was ⁇ 36 V, and Ion / Ioff was 2 ⁇ 10 8 .
  • Comparative Example 1 the mobility is low when the channel length is short, but such a tendency is not seen in the transistor of the present invention, and the channel length is short. However, the mobility did not decrease. Further, it was found that the transistor of the present invention can operate with high mobility with a short channel length, so that a large current can flow and is suitable for high-density integration. It was also found that the field effect transistor of the present invention has good characteristics with less hysteresis than the short channel length voltage-current curve. As is clear from the above results, it was found that the field effect transistor in which the compound of the present invention was laminated exhibited a good semiconductor characteristic with a clearly high mobility.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Thin Film Transistor (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

L'invention concerne un transistor à effet de champ qui contient une matière de semi-conducteur organique (A), représentée par la formule générale (1), et une matière de semi-conducteur organique (B), qui n'est pas la matière de semi-conducteur organique représentée par la formule générale (1) (X1 représente un reste hydrocarboné aliphatique éventuellement substitué ou un reste aromatique éventuellement substitué).
PCT/JP2012/055339 2011-03-02 2012-03-02 Transistor organique à effet de champ et matière de semi-conducteur organique Ceased WO2012118174A1 (fr)

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JP2015156412A (ja) * 2014-02-20 2015-08-27 富士フイルム株式会社 有機薄膜トランジスタ、有機半導体薄膜および有機半導体材料
WO2016024484A1 (fr) * 2014-08-13 2016-02-18 富士フイルム株式会社 Composition pour la formation d'un film semi-conducteur organique, matériau semi-conducteur organique pour dispositif à semi-conducteur organique non électroluminescent, matériau pour transistor organique, solution de revêtement pour dispositif à semi-conducteur organique non électroluminescent, encre pour dispositif à semi-conducteur organique non électroluminescent, film semi-conducteur organique pour dispositif à semi-conducteur organique non électroluminescent, et transistor organique
JP2016050207A (ja) * 2014-08-29 2016-04-11 日本化薬株式会社 新規な縮合多環芳香族化合物及びその用途
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JP2017519351A (ja) * 2014-04-09 2017-07-13 南京大学Ｎａｎｊｉｎｇ Ｕｎｉｖｅｒｓｉｔｙ 極薄有機結晶層を表面にエピタキシャル成長させる方法、及びその応用
JP2020092261A (ja) * 2018-12-03 2020-06-11 三星電子株式会社Ｓａｍｓｕｎｇ Ｅｌｅｃｔｒｏｎｉｃｓ Ｃｏ．，Ｌｔｄ． 有機薄膜と有機薄膜トランジスタ及び電子素子
JP2021073189A (ja) * 2016-06-03 2021-05-13 エルジー・ケム・リミテッド 電気活性化合物
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JPWO2015016003A1 (ja) * 2013-07-31 2017-03-02 富士フイルム株式会社 有機半導体組成物、有機薄膜トランジスタ、電子ペーパー、ディスプレイデバイス
JP2015156412A (ja) * 2014-02-20 2015-08-27 富士フイルム株式会社 有機薄膜トランジスタ、有機半導体薄膜および有機半導体材料
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WO2016024484A1 (fr) * 2014-08-13 2016-02-18 富士フイルム株式会社 Composition pour la formation d'un film semi-conducteur organique, matériau semi-conducteur organique pour dispositif à semi-conducteur organique non électroluminescent, matériau pour transistor organique, solution de revêtement pour dispositif à semi-conducteur organique non électroluminescent, encre pour dispositif à semi-conducteur organique non électroluminescent, film semi-conducteur organique pour dispositif à semi-conducteur organique non électroluminescent, et transistor organique
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JP2021073189A (ja) * 2016-06-03 2021-05-13 エルジー・ケム・リミテッド 電気活性化合物
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US11242357B2 (en) 2017-10-18 2022-02-08 Samsung Electronics Co., Ltd. Fused polycyclic heteroaromatic compound and organic thin film and electronic device
US11450810B2 (en) 2018-08-28 2022-09-20 Samsung Electronics Co., Ltd. Compound and thin film transistor and electronic device
US11038116B2 (en) 2018-11-26 2021-06-15 Samsung Electronics Co., Ltd. Compound and organic thin film and thin film transistor and electronic device
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