JP2006237214A - Organic semiconductor material, organic semiconductor film, organic semiconductor element, organic tft, field effect transistor, and switching element - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a good characteristics as a transistor including the issue of degradation with passage of time, and to facilitate forming of a thin film by coating. <P>SOLUTION: The organic semiconductor material contains a compound represented by a general formula (1). In the formula, Ar<SB>1</SB>to Ar<SB>4</SB>are aromatic hydrocarbon ring or aromatic hetero cycle, respectively. However, at least one of Ar<SB>1</SB>to Ar<SB>4</SB>is aromatic heterocycle. R<SB>1</SB>to R<SB>8</SB>are hydrogen atom or substituent, respectively. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  The present invention relates to an organic semiconductor material, an organic semiconductor film using the same, an organic semiconductor element, an organic thin film transistor, a field effect transistor, and a switching element using the transistor.

  With the widespread use of information terminals, there is an increasing need for flat panel displays as computer displays. In addition, with the progress of computerization, the information provided by paper media has become more and more opportunities to be provided electronically. As a mobile display medium that is thin, light and easy to carry, electronic paper or digital The need for paper is also increasing.

  In general, in a flat display device, a display medium is formed using an element utilizing liquid crystal, organic EL, electrophoresis, or the like. In such display media, in order to ensure uniformity of screen brightness, screen rewriting speed, and the like, a technique using a TFT element that is active drive as an image drive element has become mainstream. For example, in a normal computer display, these TFT elements are formed on a glass substrate, and liquid crystal, organic EL elements, etc. are sealed.

  Here, semiconductors such as a-Si (amorphous silicon) and p-Si (polysilicon) can be mainly used for the TFT element, and these Si semiconductors (and metal films as necessary) are formed into a multilayer structure. The TFT element is manufactured by sequentially forming the drain and gate electrodes on the substrate. The manufacture of such TFT elements usually requires sputtering or other vacuum manufacturing processes.

  However, in the manufacture of such a TFT element, the vacuum system manufacturing process including the vacuum chamber must be repeated many times to form each layer, and the apparatus cost and running cost have become enormous. . For example, in a TFT element, it is usually necessary to repeat processes such as vacuum deposition, dope, photolithography, development, etc. many times to form each layer, and the element is formed on a substrate through tens of steps. Yes. As for the semiconductor portion that is the key to the switching operation, a plurality of types of semiconductor layers such as p-type and n-type are stacked. In such a conventional manufacturing method using a Si semiconductor, it is not easy to change the equipment, for example, a design change of a manufacturing apparatus such as a vacuum chamber is required in response to the need for a large display screen.

  In addition, since the formation of such a conventional TFT element using a Si material includes a process at a high temperature, the substrate material is restricted to be a material that can withstand the process temperature. For this reason, glass must be used in practice, and when a thin display such as the electronic paper or digital paper described above is constructed using such a conventionally known TFT element, the display is heavy and flexible. The product may break due to chipping or dropping impact. These characteristics resulting from the formation of TFT elements on a glass substrate are undesirable in satisfying the need for an easy-to-carry-type thin display with the progress of computerization.

  Meanwhile, in recent years, organic thin film transistor materials have been energetically studied as organic compounds having high charge transport properties. These compounds are not only charge transport materials for organic EL devices, but also organic laser oscillation devices such as those discussed in Science, 289, 599 (2000), (Nature) magazine, 403, 521 (2000), etc., application to organic thin film transistors reported in many papers is expected. If these organic semiconductor devices can be realized, there is a possibility of obtaining a semiconductor that can be made into a solution by simplifying the manufacturing process by vacuum or low-pressure deposition at a relatively low temperature and further improving the molecular structure appropriately. It is conceivable that the organic semiconductor solution is made into an ink and manufactured by a printing method including an ink jet method. Manufacturing by these low-temperature processes has been considered impossible for conventional Si-based semiconductor materials, but there is a possibility for devices using organic semiconductors, so the above-mentioned restrictions on substrate heat resistance are relaxed. For example, a TFT element may be formed on the transparent resin substrate. If a TFT element is formed on a transparent resin substrate and the display material can be driven by the TFT element, the display is lighter and more flexible than conventional ones, and will not crack even if dropped (or very difficult to break) It could be a display.

As organic semiconductor materials, polyphenylene vinylene, polypyrrole, polythiophene, oligothiophene, pentacene, and the like have been studied. In particular, polyacene compounds such as pentacene can provide high carrier mobility and excellent semiconductor device characteristics. It has been reported. Moreover, although the polyacene compound or the polyacene compound derivative is disclosed (for example, refer to Patent Documents 1 to 4 and Non-Patent Document 1), both of them are compatible with solution process suitability, carrier mobility, and semiconductor device characteristics. The development of further organic semiconductor materials has been desired.
International Publication No. 03/16599 pamphlet International Publication No. 03/28125 Pamphlet US Pat. No. 6,690,029 JP 2004-107216 A Science magazine, 303, 1644-1646 (2004)

  An object of the present invention is to provide an organic semiconductor material that has good characteristics as a transistor including deterioration over time and that can be easily formed into a thin film by coating, an organic semiconductor film using the same, an organic semiconductor element, an organic thin film transistor, and a field effect type A transistor and a switching element using the transistor are provided.

  The above object of the present invention has been achieved by the following constitution.

(Claim 1)
An organic semiconductor material comprising a compound represented by the following general formula (1):

(In the formula, Ar _{1 to} Ar ₄ each represent an aromatic hydrocarbon ring or an aromatic heterocyclic ring, provided that at least one of Ar _{1 to} Ar ₄ is an aromatic heterocyclic ring. R _{1 to} R ₈ are each Represents a hydrogen atom or a substituent.)
(Claim 2)
In the said General formula (1), the aromatic heterocyclic ring which Ar < ₁ > -Ar < ₄ > represents is a 5-membered ring, The organic-semiconductor material of Claim 1 characterized by the above-mentioned.

(Claim 3)
In the said General formula (1), the aromatic heterocyclic ring which Ar < ₁ > -Ar < ₄ > represents is a 6-membered ring, The organic-semiconductor material of Claim 1 characterized by the above-mentioned.

(Claim 4)
In the said General formula (1), the hetero atom which forms the aromatic heterocycle which Ar < ₁ > -Ar < ₄ > represents is chosen from N, S, O, The any one of Claims 1-3 characterized by the above-mentioned. Organic semiconductor materials.

(Claim 5)
In the said General formula (1), all R < ₁ > -R < ₈ > is a hydrogen atom, The organic-semiconductor material of any one of Claims 1-4 characterized by the above-mentioned.

(Claim 6)
In the general formula (1), R ₁ , R ₄ , R ₅ , and R ₈ each represent an alkyl group, and R ₂ , R ₃ , R ₆ , and R ₇ each represent a hydrogen atom. The organic-semiconductor material of any one of 1-4.

(Claim 7)
The general formula (1), wherein one of R ₁ and R ₈ is an alkyl group and the other is a hydrogen atom, one of R ₄ and R ₅ is an alkyl group, and the other is a hydrogen atom. The organic-semiconductor material of any one of 1-4.

(Claim 8)
An organic semiconductor film comprising the organic semiconductor material according to claim 1.

(Claim 9)
The organic-semiconductor element characterized by including the organic-semiconductor material of any one of Claims 1-7.

(Claim 10)
An organic thin film transistor comprising the organic semiconductor material according to claim 1 in a semiconductor layer.

(Claim 11)
A field effect transistor comprising the organic semiconductor material according to claim 1 in a semiconductor layer.

(Claim 12)
A switching element comprising the organic thin film transistor according to claim 10 or the field effect transistor according to claim 11.

  According to the present invention, an organic semiconductor material that has good characteristics as a transistor including deterioration over time and that can be easily formed into a thin film by coating, an organic semiconductor film, an organic semiconductor element, an organic thin film transistor, and a field effect transistor using the organic semiconductor material, In addition, a switching element using the transistor can be provided.

  Hereinafter, the present invention will be described in detail.

In the general formula (1), Ar _{1 to} Ar ₄ each represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring. However, at least one of Ar _{1 to} Ar ₄ is an aromatic heterocycle. The aromatic heterocycle is preferably a 5-membered or 6-membered ring, and the heteroatoms constituting it are preferably N, S, or O. Examples of the aromatic 5-membered heterocyclic ring include a pyrrole ring, an imidazole ring, a pyrazole ring, a thiophene ring, a furan ring, an isothiazole ring, and an isoxazole ring. Examples of the aromatic 6-membered heterocyclic ring include a pyridine ring, a pyrimidine ring, and a pyridazine ring. And a pyran ring. Examples of the aromatic hydrocarbon ring include a benzene ring, a naphthalene ring, and an anthracene ring.

The aromatic hydrocarbon ring or aromatic heterocyclic ring represented by Ar _{1 to} Ar ₄ may have a substituent. Examples of the substituent include an alkyl group (for example, a methyl group, an ethyl group, a propyl group, an isopropyl group). Tert-butyl group, pentyl group, hexyl group, octyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, etc.), cycloalkyl group (for example, cyclopentyl group, cyclohexyl group, etc.), alkenyl group (for example, vinyl group) Allyl group, etc.), alkynyl group (eg, ethynyl group, propargyl group, etc.), aryl group (eg, phenyl group, naphthyl group, etc.), heteroaryl group (eg, furyl group, thienyl group, pyridyl group, pyridazyl group, Pyrimidyl group, pyrazyl group, triazyl group, imidazolyl group, pyrazolyl group, thiazolyl group, benzimid Zolyl group, benzoxazolyl group, quinazolyl group, phthalazyl group, etc.), heterocyclic group (eg, pyrrolidyl group, imidazolidyl group, morpholyl group, oxazolidyl group, etc.), alkoxy group (eg, methoxy group, ethoxy group, propyloxy) Group, pentyloxy group, hexyloxy group, octyloxy group, dodecyloxy group, etc.), cycloalkoxy group (eg, cyclopentyloxy group, cyclohexyloxy group, etc.), aryloxy group (eg, phenoxy group, naphthyloxy group, etc.) , Alkylthio groups (eg, methylthio group, ethylthio group, propylthio group, pentylthio group, hexylthio group, octylthio group, dodecylthio group, etc.), cycloalkylthio groups (eg, cyclopentylthio group, cyclohexylthio group, etc.), arylthio groups (eg, For example, phenylthio group, naphthylthio group, etc.), alkoxycarbonyl group (eg, methyloxycarbonyl group, ethyloxycarbonyl group, butyloxycarbonyl group, octyloxycarbonyl group, dodecyloxycarbonyl group, etc.), aryloxycarbonyl group (eg, Phenyloxycarbonyl group, naphthyloxycarbonyl group, etc.), sulfamoyl group (for example, aminosulfonyl group, methylaminosulfonyl group, dimethylaminosulfonyl group, butylaminosulfonyl group, hexylaminosulfonyl group, cyclohexylaminosulfonyl group, octylaminosulfonyl group) , Dodecylaminosulfonyl group, phenylaminosulfonyl group, naphthylaminosulfonyl group, 2-pyridylaminosulfonyl group, etc.), acyl group (for example, aceto Group, ethylcarbonyl group, propylcarbonyl group, pentylcarbonyl group, cyclohexylcarbonyl group, octylcarbonyl group, 2-ethylhexylcarbonyl group, dodecylcarbonyl group, phenylcarbonyl group, naphthylcarbonyl group, pyridylcarbonyl group, etc.), acyloxy group ( For example, acetyloxy group, ethylcarbonyloxy group, butylcarbonyloxy group, octylcarbonyloxy group, dodecylcarbonyloxy group, phenylcarbonyloxy group, etc.), amide group (for example, methylcarbonylamino group, ethylcarbonylamino group, dimethylcarbonyl) Amino group, propylcarbonylamino group, pentylcarbonylamino group, cyclohexylcarbonylamino group, 2-ethylhexylcarbonylamino group, octylcal Nylamino group, dodecylcarbonylamino group, phenylcarbonylamino group, naphthylcarbonylamino group, etc.), carbamoyl group (for example, aminocarbonyl group, methylaminocarbonyl group, dimethylaminocarbonyl group, propylaminocarbonyl group, pentylaminocarbonyl group, cyclohexyl) Aminocarbonyl group, octylaminocarbonyl group, 2-ethylhexylaminocarbonyl group, dodecylaminocarbonyl group, phenylaminocarbonyl group, naphthylaminocarbonyl group, 2-pyridylaminocarbonyl group, etc.), ureido group (for example, methylureido group, ethylureido) Group, pentylureido group, cyclohexylureido group, octylureido group, dodecylureido group, phenylureido group, naphthylureido group, 2-pyri Dilaminoureido group, etc.), sulfinyl group (for example, methylsulfinyl group, ethylsulfinyl group, butylsulfinyl group, cyclohexylsulfinyl group, 2-ethylhexylsulfinyl group, dodecylsulfinyl group, phenylsulfinyl group, naphthylsulfinyl group, 2-pyridylsulfinyl group) Group), alkylsulfonyl group (for example, methylsulfonyl group, ethylsulfonyl group, butylsulfonyl group, cyclohexylsulfonyl group, 2-ethylhexylsulfonyl group, dodecylsulfonyl group, etc.), arylsulfonyl group (for example, phenylsulfonyl group, naphthylsulfonyl) Group, 2-pyridylsulfonyl group, etc.), amino group (for example, amino group, ethylamino group, dimethylamino group, butylamino group, cyclopentylamino group, -Ethylhexylamino group, dodecylamino group, anilino group, naphthylamino group, 2-pyridylamino group, etc.), halogen atom (eg, fluorine atom, chlorine atom, bromine atom etc.), fluorinated hydrocarbon group (eg, fluoromethyl group) , Trifluoromethyl group, pentafluoroethyl group, pentafluorophenyl group, etc.), cyano group, silyl group (for example, trimethylsilyl group, triisopropylsilyl group, triphenylsilyl group, phenyldiethylsilyl group, etc.) These substituents may be further substituted with the above substituents, or a plurality thereof may be bonded to each other to form a ring.

R _{1 to} R ₈ represent a hydrogen atom or a substituent, and examples of the substituent include those described above. Among the substituents, an alkyl group is preferable, R ₁ , R ₄ , R ₅ , and R ₈ each represent an alkyl group, and R ₂ , R ₃ , R ₆ , and R ₇ each preferably represent a hydrogen atom. Furthermore, it is preferable that all of R _{1 to} R ₈ are hydrogen atoms. It is also preferred that _one of R ₁ and R ₈ is an alkyl group and the other is a hydrogen atom, and one of R ₄ and R ₅ is an alkyl group and the other is a hydrogen atom.

  Hereinafter, although the specific example of a compound represented by the said General formula (1) based on this invention is shown, this invention is not limited to these.

  The compound represented by the general formula (1) according to the present invention can be synthesized, for example, by the following method.

  More specifically, J. et al. Org. Chem. , 55, 13, 1990, 4190 to 4198.

  An organic thin film transistor has a source electrode and a drain electrode connected by an organic semiconductor channel (active layer) on a support, and a top gate type having a gate electrode on the support and a support on the support first. It is roughly classified into a bottom gate type having a gate electrode and having a source electrode and a drain electrode connected by an organic semiconductor channel through a gate insulating layer.

  In order to install the compound according to the present invention in the active layer of the organic thin-film transistor element, it can be installed on the substrate by vacuum deposition, but it can be dissolved in an appropriate solvent, and a solution prepared by adding additives as necessary. It is preferable to install on the substrate by cast coating, spin coating, printing, ink jet method, ablation method or the like. In this case, the solvent for dissolving the organic semiconductor material of the present invention is not particularly limited as long as the organic semiconductor material can be dissolved to prepare a solution having an appropriate concentration. Specifically, diethyl ether or diisopropyl is used. Chain ether solvents such as ether, cyclic ether solvents such as tetrahydrofuran and dioxane, ketone solvents such as acetone and methyl ethyl ketone, alkyl halide solvents such as chloroform and 1,2-dichloroethane, toluene, o-dichlorobenzene, Examples thereof include aromatic solvents such as nitrobenzene and m-cresol, chain hydrocarbon solvents such as hexane, cyclic hydrocarbon solvents such as cyclohexane, N-methylpyrrolidone, carbon disulfide and the like.

  In the present invention, the material for forming the source electrode, the drain electrode and the gate electrode is not particularly limited as long as it is a conductive material. Platinum, gold, silver, nickel, chromium, copper, iron, tin, antimony lead, tantalum, Indium, palladium, tellurium, rhenium, iridium, aluminum, ruthenium, germanium, molybdenum, tungsten, tin oxide / antimony, indium tin oxide (ITO), fluorine-doped zinc oxide, zinc, carbon, graphite, glassy carbon, silver paste and Carbon paste, lithium, beryllium, sodium, magnesium, potassium, calcium, scandium, titanium, manganese, zirconium, gallium, niobium, sodium, sodium-potassium alloy, magnesium, lithium, aluminum, magnesium Copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide mixture, lithium / aluminum mixture, etc. are used, especially platinum, gold, silver, copper, aluminum, indium, ITO and carbon Is preferred. Alternatively, known conductive polymers whose conductivity is improved by doping or the like, for example, conductive polyaniline, conductive polypyrrole, conductive polythiophene, a complex of polyethylenedioxythiophene and polystyrenesulfonic acid, and the like are also preferably used. Among them, those having low electrical resistance at the contact surface with the semiconductor layer are preferable.

  As a method for forming an electrode, a method for forming an electrode using a known photolithographic method or a lift-off method, using a conductive thin film formed by a method such as vapor deposition or sputtering using the above as a raw material, a metal foil such as aluminum or copper There is a method of etching using a resist by thermal transfer, ink jet or the like. Alternatively, a conductive polymer solution or dispersion, or a conductive fine particle dispersion may be directly patterned by ink jetting, or may be formed from a coating film by lithography or laser ablation. Furthermore, a method of patterning an ink containing a conductive polymer or conductive fine particles, a conductive paste, or the like by a printing method such as relief printing, intaglio printing, planographic printing, or screen printing can also be used.

  Various insulating films can be used as the gate insulating layer, and an inorganic oxide film having a high relative dielectric constant is particularly preferable. Inorganic oxides include silicon oxide, aluminum oxide, tantalum oxide, titanium oxide, tin oxide, vanadium oxide, barium strontium titanate, barium zirconate titanate, lead zirconate titanate, lead lanthanum titanate, strontium titanate, Examples thereof include barium titanate, barium magnesium fluoride, bismuth titanate, strontium bismuth titanate, strontium bismuth tantalate, bismuth tantalate niobate, and yttrium trioxide. Of these, silicon oxide, aluminum oxide, tantalum oxide, and titanium oxide are preferable. Inorganic nitrides such as silicon nitride and aluminum nitride can also be suitably used.

  Examples of the method for forming the film include a vacuum process, a molecular beam epitaxial growth method, an ion cluster beam method, a low energy ion beam method, an ion plating method, a CVD method, a sputtering method, an atmospheric pressure plasma method, and a spray process. Wet processes such as coating methods, spin coating methods, blade coating methods, dip coating methods, casting methods, roll coating methods, bar coating methods, die coating methods, and other wet processes such as printing and ink jet patterning methods, etc. Can be used depending on the material.

  The wet process is a method of applying and drying a liquid in which fine particles of inorganic oxide are dispersed in an arbitrary organic solvent or water using a dispersion aid such as a surfactant as required, or an oxide precursor, for example, A so-called sol-gel method in which a solution of an alkoxide body is applied and dried is used.

  Among these, the atmospheric pressure plasma method and the sol-gel method are preferable.

  The method for forming an insulating film by plasma film formation under atmospheric pressure is a process in which a reactive gas is discharged under atmospheric pressure or a pressure near atmospheric pressure to excite reactive gas to form a thin film on a substrate. The method is described in JP-A-11-61406, JP-A-11-133205, JP-A-2000-121804, JP-A-2000-147209, and JP-A-2000-185362. Thereby, a highly functional thin film can be formed with high productivity.

  In addition, as an organic compound film, polyimide, polyamide, polyester, polyacrylate, photo radical polymerization type, photo cation polymerization type photo curable resin, or a copolymer containing an acrylonitrile component, polyvinyl phenol, polyvinyl alcohol, novolac resin, Also, cyanoethyl pullulan or the like can be used.

  As the method for forming the organic compound film, the wet process is preferable.

  An inorganic oxide film and an organic oxide film can be laminated and used together. The thickness of these insulating films is generally 50 nm to 3 μm, preferably 100 nm to 1 μm.

  Moreover, a support body is comprised with glass or a flexible resin-made sheet | seat, for example, a plastic film can be used as a sheet | seat. Examples of the plastic film include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC). And a film made of cellulose triacetate (TAC), cellulose acetate propionate (CAP), or the like. Thus, by using a plastic film, the weight can be reduced as compared with the case of using a glass substrate, the portability can be improved, and the resistance to impact can be improved.

  Below, the field effect type organic thin-film transistor using the organic thin film which consists of the organic-semiconductor material of this invention is demonstrated.

  FIG. 1 shows a configuration example of a field effect type organic thin film transistor using an organic semiconductor material of the present invention for an active layer. In FIG. 2A, a source electrode 2 and a drain electrode 3 are formed on a support 6 by a metal foil or the like, an active layer 1 made of the organic semiconductor material of the present invention is formed between both electrodes, and an insulating layer is formed thereon. 5 is formed, and a gate electrode 4 is further formed thereon to form a field effect transistor. FIG. 2B shows the active layer 1 formed between the electrodes in FIG. 1A so as to cover the entire surface of the electrode and the support using a coating method or the like. (C) shows that the active layer 1 is first formed on the support 6 by using a coating method or the like, and then the source electrode 2, the drain electrode 3, the insulating layer 5, and the gate electrode 4 are formed.

  In FIG. 4D, after forming the gate electrode 4 on the support 6 with a metal foil or the like, the insulating layer 5 is formed thereon, and the source electrode 2 and the drain electrode 3 are formed on the metal foil or the like. An active layer 1 made of the semiconductor material of the present invention is formed between the electrodes. In addition, the configuration as shown in FIGS.

  EXAMPLES Hereinafter, although an Example demonstrates this invention, the embodiment of this invention is not limited to these.

Example 1
A thermal oxide film having a thickness of 2000 mm was formed on a Si wafer having a specific resistance of 0.01 Ω · cm as a gate electrode to form a gate insulating layer, and then surface treatment with octyltrichlorosilane was performed. A cast film (thickness: 50 nm) was prepared by applying a chloroform solution of comparative compound <1> (poly (3-hexylthiophene) (regioregular, Aldrich, average molecular weight 89000, PHT)) using an applicator and air drying. And was heat-treated at 50 ° C. for 30 minutes in a nitrogen atmosphere. Furthermore, gold was deposited on the surface of this film using a mask to form source and drain electrodes. An organic thin film transistor element 1 having a width of 100 μm, a thickness of 200 nm, a channel width W = 3 mm, and a channel length L = 20 μm was prepared.

  Organic thin-film transistor element 2 was produced in the same manner as organic thin-film transistor element 1, except that comparative compound <1> was replaced with comparative compound <2> (pentacene, a commercially available reagent manufactured by Aldrich). .

  Further, organic thin film transistor elements 3 to 7 were produced in the same manner as the organic thin film transistor element 1 except that the comparative compound <1> was replaced with the exemplary compounds according to the present invention shown in Table 1.

  The organic thin film transistor elements 1 and 3 to 7 manufactured as described above showed good operating characteristics of p-channel enhancement type FETs. Further, for the organic thin film transistor elements 1 to 7, from the saturation region of the IV characteristics, the carrier mobility and the ON / OFF ratio (the drain bias value ratio when the drain bias is −50 V and the gate bias is −50 V and 0 V) are set. Asked. The obtained element was left in the atmosphere for one month, and the carrier mobility and the ON / OFF ratio were obtained again. The results are shown in Table 1.

  From the results shown in Table 1, it was found that the organic thin film transistor element of the present invention had good characteristics as a transistor and further suppressed deterioration over time.

  Moreover, although the result of the organic thin film transistor element 2 using the comparative compound <2> (pentacene) clearly shows that it is difficult to obtain a pentacene thin film functioning as an active layer by forming a thin film by coating, It was found that the thin film transistor element exhibits good characteristics as a transistor when a thin film is formed by coating.

It is a figure which shows the structural example of the field effect type organic thin-film transistor which used organic-semiconductor material for the active layer.

Explanation of symbols

DESCRIPTION OF SYMBOLS 1 Active layer 2 Source electrode 3 Drain electrode 4 Gate electrode 5 Insulating layer 6 Support body

Claims (12)

An organic semiconductor material comprising a compound represented by the following general formula (1):

(In the formula, Ar _{1 to} Ar ₄ each represent an aromatic hydrocarbon ring or an aromatic heterocyclic ring, provided that at least one of Ar _{1 to} Ar ₄ is an aromatic heterocyclic ring. R _{1 to} R ₈ are each Represents a hydrogen atom or a substituent.) In the said General formula (1), the aromatic heterocyclic ring which Ar < ₁ > -Ar < ₄ > represents is a 5-membered ring, The organic-semiconductor material of Claim 1 characterized by the above-mentioned. In the said General formula (1), the aromatic heterocyclic ring which Ar < ₁ > -Ar < ₄ > represents is a 6-membered ring, The organic-semiconductor material of Claim 1 characterized by the above-mentioned. In the said General formula (1), the hetero atom which forms the aromatic heterocycle which Ar < ₁ > -Ar < ₄ > represents is chosen from N, S, O, The any one of Claims 1-3 characterized by the above-mentioned. Organic semiconductor materials. In the said General formula (1), all R < ₁ > -R < ₈ > is a hydrogen atom, The organic-semiconductor material of any one of Claims 1-4 characterized by the above-mentioned. In the general formula (1), R ₁ , R ₄ , R ₅ , and R ₈ each represent an alkyl group, and R ₂ , R ₃ , R ₆ , and R ₇ each represent a hydrogen atom. The organic-semiconductor material of any one of 1-4. The general formula (1), wherein one of R ₁ and R ₈ is an alkyl group and the other is a hydrogen atom, one of R ₄ and R ₅ is an alkyl group, and the other is a hydrogen atom. The organic-semiconductor material of any one of 1-4. An organic semiconductor film comprising the organic semiconductor material according to claim 1. The organic-semiconductor element characterized by including the organic-semiconductor material of any one of Claims 1-7. An organic thin film transistor comprising the organic semiconductor material according to claim 1 in a semiconductor layer. A field effect transistor comprising the organic semiconductor material according to claim 1 in a semiconductor layer. A switching element comprising the organic thin film transistor according to claim 10 or the field effect transistor according to claim 11.

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