WO2006098121A1 - Organic semiconductor material, organic semiconductor film, organic semiconductor device, organic thin-film transistor, and method for manufacturing organic thin-film transistor - Google Patents

Abstract

Disclosed is an organic semiconductor material which can be produced by a simple process while having good characteristics as a transistor. This organic semiconductor material is suppressed in deterioration over time. Also disclosed are an organic semiconductor film using such an organic semiconductor material, an organic semiconductor device, an organic thin-film transistor and a method for manufacturing an organic thin-film transistor. Specifically disclosed is an organic semiconductor material characterized by containing a compound represented by the following general formula (1). General formula (1) Ar1-L-Ar2 (In the formula, Ar1 and Ar2 respectively represent a hydrogen atom or a substituent, and at least one of Ar1 and Ar2 is an aromatic hydrocarbon fused ring or an aromatic heterocyclic fused ring wherein aromatic hydrocarbon rings or aromatic heterocyclic rings are fused; and L represents a linked group connected by a conjugated system containing an aromatic hydrocarbon ring or an aromatic heterocyclic ring.

Description

 Specification

 Organic semiconductor material, organic semiconductor film, organic semiconductor device, organic thin film transistor, and method for forming organic thin film transistor

 Technical field

 The present invention relates to an organic semiconductor material, an organic semiconductor film, an organic semiconductor device, an organic thin film transistor, and a method for forming an organic thin film transistor.

 Background art

 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 been increasingly digitized, and electronic paper is a display medium for mopile that is thin, light, and easy to carry. There is a growing need for digital paper.

 [0003] Generally, in a flat display device, a display medium is formed by using elements utilizing liquid crystal, organic EL (organic electoluminescence), electrophoresis, or the like. In such display media, a technology using an active drive element (TFT element) as an image drive element has become mainstream to ensure uniformity of screen brightness, screen rewriting speed, and the like! For example, in an ordinary 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 TFT elements, and these S 泮 conductors (and metal films as required). The TFT element is manufactured by forming a multi-layered structure and sequentially forming source, drain, and gate electrodes on the substrate. The production of such TFT elements usually requires sputtering and other vacuum-based manufacturing processes.

[0005] 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, resulting in extremely high equipment costs and running costs. It was huge. For example, in TFT devices, it is usually necessary to repeat the steps of vacuum deposition, dope, photolithography, development, etc. many times to form each layer. The device is formed on the substrate through several tens of steps. For the semiconductor portion that is the key to the switching operation, multiple types of semiconductor layers such as p-type and n-type are stacked. In such a conventional manufacturing method using Si semiconductors, 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.

 [0006] In addition, since the formation of a TFT element using such a conventional Si material includes a process at a high temperature, the substrate material is limited to a material that can withstand the process temperature. Become. For this reason, in practice, glass must be used, and when the above-mentioned electronic paper or digital paper! /, And a thin display using such a conventionally known TFT element are used, the display Will be heavy and inflexible, and may be broken by the impact of a drop. These characteristics resulting from the formation of TFT elements on a glass substrate are desirable in satisfying the demand for easy-to-use thin displays for portable use as information technology advances.

[0007] On the other hand, research on organic semiconductor materials has been energetically advanced in recent years as an organic compound having a high charge transporting property. These compounds are reported in numerous papers such as organic laser oscillators as discussed in Non-Patent Document 1, etc., as well as, for example, Non-Patent Document 2, in addition to charge transport materials for organic EL devices. Applications to organic thin film transistor devices (organic TFT devices) are expected! If these organic semiconductor devices can be realized, it is possible to obtain a semiconductor that can be made into a solution by making the manufacturing process relatively low, vacuuming at a temperature, simplifying the manufacturing process by low-pressure deposition, and further improving the molecular structure appropriately. Production by printing methods including inkjet method by converting organic semiconductor solution into ink is also considered. Manufacturing using these low-temperature processes has been considered impossible for conventional Si-based semiconductor materials, but there are possibilities for devices using organic semiconductors, and therefore 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 will be lighter and more flexible than conventional ones, and will not crack even if dropped (or (It is difficult to break)). [0008] However, as an organic semiconductor for realizing such a TFT element, the acenes such as pentacene and tetracene have been studied so far (for example, see Patent Document 1), and phthalocyanines including lead phthalocyanine. Low molecular weight compounds such as perylene and its tetracarboxylic acid derivatives (see, for example, Patent Document 2), and aromatic oligomers represented by a thiophene hexamer called a chenille or sexithiophene (for example, Patent Document 3). ), Naphthalene, anthracene and symmetrical compounds of 5-membered aromatic heterocycles (for example, see Patent Document 4), modified oligos and polydithienopyridines (for example, see Patent Document 5), and polythiophene Conjugated polymers such as poly-ethylene biylene and poly-p-phenylene biylene, etc. The development of a semiconducting composition using a novel charge transporting material exhibiting a high carrier mobility that can only be achieved with a compound (for example, see Non-Patent Documents 1 to ₃ ) has been awaited.

[0009] In addition, in Japanese Patent Application Laid-Open No. 2003-292588, US Patent Application Publication No. 2003/136958, 2003Z160230, 2003,164495, "Integrated circuit logic for micro-elect port-tas" is disclosed. The use of polymer TFTs in the device greatly improves the mechanical durability and prolongs the useful life of the device, and many of the semiconductor polythiophenes are oxidatively doped with ambient oxygen, increasing the conductivity. As a result, the devices manufactured by these materials have a higher off-current and therefore a lower current-on-Z-off ratio. Many must be very careful to eliminate environmental oxygen during material processing and device manufacturing to avoid or minimize acid doping. To increase costs, the attractiveness of certain polymer TFTs as an economical alternative to amorphous silicon technology, especially for large area devices, is diminished. Therefore, an electronic device having a strong resistance to oxygen and a relatively high current ONNZOFF ratio is desired ”. Various means have been proposed (see, for example, Patent Documents 6, 7, and 8), but further improvements are desired that do not satisfy the level of improvement.

Patent Document 1: Japanese Patent Laid-Open No. 5-55568 Patent Document 2: JP-A-5-190877

 Patent Document 3: JP-A-8-264805

 Patent Document 4: JP-A-11-195790

 Patent Document 5: Japanese Patent Laid-Open No. 2003-155289

 Patent Document 6: Japanese Patent Laid-Open No. 2003-261655

 Patent Document 7: Japanese Unexamined Patent Publication No. 2003-264327

 Patent Document 8: Japanese Unexamined Patent Application Publication No. 2003-268083

 Non-Patent Document 1: Science 289 卷, 599 pages (2000)

 Non-Patent Document 2: “Nature” 403ature, 521 pages (2000)

 Non-Patent Document 3: "Advanced Material", 2002, No. 2, page 99

 Disclosure of the invention

 Problems to be solved by the invention

[0010] An object of the present invention is an organic semiconductor material that is manufactured by a simple process, has good characteristics as a transistor, and further suppresses deterioration over time, an organic semiconductor film using the organic semiconductor material, an organic semiconductor device, An organic thin film transistor and a method for forming the organic thin film transistor are provided.

 Means for solving the problem

[0011] The above-described problems of the present invention are achieved by the following configurations.

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

[0012] General formula (1) Ar -L-Ar

 1 2

 (In the formula, Ar and Ar represent a hydrogen atom or a substituent, and at least one of Ar and Ar is

 1 2 1 2 Aromatic hydrocarbon condensed ring or aromatic heterocyclic condensed ring condensed with aromatic hydrocarbon ring or aromatic heterocyclic ring, L is bonded with a conjugated system containing aromatic hydrocarbon ring or aromatic heterocyclic ring Represents a linking group. )

 2. Ar and Ar are aromatic condensed with an aromatic hydrocarbon ring or aromatic heterocycle

 1 2

2. The organic semiconductor material as described in 1 above, which is a hydrocarbon condensed ring or an aromatic hetero condensed ring. 3. An organic semiconductor material comprising a compound represented by the following general formula (2):

[Chemical formula 1] General formula>

[Wherein Ar and Ar represent a hydrogen atom or a substituent, and at least one of Ar and Ar

 21 22 21 22

 Is an aromatic hydrocarbon condensed ring or an aromatic hetero condensed ring condensed with an aromatic hydrocarbon ring or an aromatic hetero ring, and R

 21 and R

 22 represents a hydrogen atom or a substituent, L

 21 represents a linking group bonded with a conjugated system containing an aromatic hydrocarbon ring or an aromatic heterocycle. )

4. Aromatic condensed Ar or Ar force aromatic hydrocarbon ring or aromatic heterocycle

 21 22

 4. The organic semiconductor material as described in 3 above, which is a hydrocarbon condensed ring or an aromatic hetero condensed ring.

 5. The organic semiconductor material according to any one of 1 to 4 above, wherein the compound represented by the general formula (1) or (2) has a molecular weight of 10,000 or less.

 6. Compound power represented by the general formula (1) or (2) The organic compound according to any one of the above 1 to 5, which has a partial structure represented by the following general formula (3) Semiconductor material.

 [0015] [Chemical formula 2] General formula (3)

_{■ ΑΓ 3 Ί -Ar 3 - 2} , - Ar 3 '3

[In the formula, Ar to Ar are aromatic hydrocarbon rings or aromatic heterocyclic rings, and R is a substituent.

 31 33 31

 R and R represent a hydrogen atom or a substituent. )

 32 33

 7. L in the general formula (1) or L force in the general formula (2) The general formula (3)

 twenty one

6. The organic semiconductor material according to any one of 1 to 5, wherein the organic semiconductor material has a partial structure represented by: 8. L in the general formula (1) or L force in the general formula (2)

 twenty one

 6. The organic semiconductor material according to any one of 1 to 5 above, which contains a substituted thiophene ring.

 9. L in the general formula (1) or L force in the general formula (2)

 twenty one

 6. The organic semiconductor material according to any one of 1 to 5, wherein the organic semiconductor material has a partial structure in which two or more substituted thiophene rings are connected.

 10. The compound power represented by the general formula (1) or (2) has a partial structure represented by the following general formula (4), according to any one of the above 1 to 5, Organic semiconductor materials.

[0017] [Chemical 3] General formula (4>

[In the formula, R represents a substituent.]

 11. L in the general formula (1) or L force in the general formula (2)

 twenty one

 6. The organic semiconductor material according to any one of 1 to 5, which has a partial structure represented by:

 12. An organic semiconductor film comprising the organic semiconductor material according to any one of 1 to 11 above.

 13. An organic semiconductor device using the organic semiconductor material according to any one of 1 to 11 above.

 14. An organic thin film transistor, wherein the organic semiconductor material according to any one of 1 to 11 is used for a semiconductor layer.

15. A method for forming an organic thin film transistor, wherein the semiconductor layer is formed by applying a solution or dispersion containing the organic semiconductor material described in any one of 1 to 11 above. The invention's effect

 [0019] According to the present invention, an organic semiconductor material that is manufactured by a simple process, has good characteristics as a transistor, and further suppresses deterioration over time, an organic semiconductor film using the organic semiconductor material, an organic semiconductor device, An organic thin film transistor and a method for forming the organic thin film transistor can be provided.

 Brief Description of Drawings

[0020] Fig. 1 is a diagram showing a structural example of an organic thin film transistor of the present invention.

 FIG. 2 is an example of a schematic equivalent circuit diagram of the organic thin film transistor sheet of the present invention.

 Explanation of symbols

[0021] 1 Organic semiconductor layer

 2 Source electrode

 3 Drain electrode

 4 Gate electrode

 5 Insulation layer

 6 Support

 7 Gate bus line

 8 Sourcenos line

 10 Organic thin film transistor sheet

 11 Organic thin-film transistors

 12 Output element

 13 Storage capacitor

 14 Vertical drive circuit

 15 Horizontal drive circuit

 BEST MODE FOR CARRYING OUT THE INVENTION

[0022] In the organic semiconductor material of the present invention, an organic semiconductor material useful for a thin film transistor can be obtained by using the structure defined in any one of claims 1 to: L1. . The organic semiconductor of the present invention produced using the organic semiconductor material is also provided. Body films, organic semiconductor devices, and organic thin film transistors (hereinafter also referred to as organic TFTs) have excellent transistor characteristics such as high carrier mobility and high durability, and high durability. However, it was divided.

[0023] As an organic semiconductor material, pentacene is a well-known force-insoluble material, and conventionally, a force film cannot be formed by evaporation, and it is difficult to produce a coating film. A thiophene oligomer without a substituent such as unsubstituted 6T can easily form a π stack between molecules, but it is insoluble like pentacene and cannot form a force film by vapor deposition. It was. In addition, since the activity at the 4-position of terminal thiophene is high, there was a problem in the temporal stability of the material and the coating film.

 [0024] On the other hand, a thiophene polymer such as ΡΗΤ that has been proposed as a material that can be applied has been proposed. A polymer with a molecular weight distribution is not sufficient to form a π stack, and the molecular arrangement is disordered. We were able to achieve satisfactory TFT performance with many parts.

 [0025] As a result of various studies on the above problems, the present inventors have improved the stacking property between molecules by introducing an aromatic hydrocarbon condensed ring or an aromatic heterocondensed ring at the terminal, and moreover. By restricting the molecular weight to a specific range, it became possible to improve the molecular arrangement. Furthermore, it was possible to produce a film in which molecules regularly arranged such as those known in the prior art pentacene were arranged, and TFT performance could be improved.

 [0026] Further, as in the present invention, functional separation of a partial structure of thiophene oligomer or the like (separation into a solubility promoting unit and a π stack promoting unit) provides sufficient solvent solubility while maintaining molecular arrangement. It was possible to form a high film, and the TFT performance (mobility) could be improved.

 [0027] In addition, by replacing the 2-position of the thiophene ring with an aromatic hydrocarbon condensed ring or an aromatic heterocondensed ring, the active site of the thiophene ring is closed, and stability over time is improved.

[0028] Details of each component according to the present invention will be described below.

[0029] [Organic semiconductor material]

 (Compound represented by the general formula (1))

The organic semiconductor material of the present invention is characterized by containing a compound represented by the above general formula (1) or (2). [0030] The compound represented by the general formula (1) according to the present invention will be described.

 [0031] In the general formula (1), Ar and Ar represent a hydrogen atom or a substituent,

 1 2 1 2 At least one represents an aromatic hydrocarbon condensed ring or an aromatic hetero condensed ring in which an aromatic hydrocarbon ring or an aromatic heterocyclic ring is condensed. Furthermore, both Ar and Ar are aromatic charcoal

 1 2

 It is preferably an aromatic hydrocarbon condensed ring or an aromatic complex condensed ring in which a hydrogenated ring or an aromatic heterocyclic ring is condensed.

 In the present invention, the above-mentioned “aromatic hydrocarbon condensed ring or aromatic heterocondensed ring condensed with an aromatic hydrocarbon ring or aromatic heterocycle” means an aromatic hydrocarbon condensed composed only of an aromatic hydrocarbon ring. It means an aromatic heterocondensed ring composed only of a ring, an aromatic heterocycle, or an aromatic heterocondensed ring composed of an aromatic hydrocarbon ring and an aromatic heterocondensed ring.

 Here, the aromatic heterofused ring preferably contains at least one heteroatom selected from N, O and S. Furthermore, these condensed rings may optionally have a substituent. In addition, the condensed aromatic hydrocarbon condensed ring and aromatic heterocyclic condensed ring are preferably composed of a 5-membered ring or a 6-membered ring.

[0032] Further, an aromatic hydrocarbon condensed ring or an aromatic hetero condensed ring represented by Ar or Ar

 1 2

 In the case where the ring bonded to L is a 6-membered ring, the atom next to the atom involved in the bond to L is bonded to an atom other than hydrogen, and is bonded to other than the atoms constituting the ring Preferably not.

 [0033] The aromatic hydrocarbon condensed ring condensed with an aromatic hydrocarbon ring is an acene (acene is a compound in which a plurality of benzene rings are condensed, such as naphthalene, anthracene, tetracene, pentacene, Hexacene, phenanthrene, pyrene, etc.), azulene ring, taricene ring, naphthacene ring, acenaphthene ring, coronene ring, fluorene ring, fluoranthrene ring, naphthacene ring, perylene ring, pentaphen ring, picene ring, pyrene ring, pyranthrene Ring, anthraanthrene ring and the like. Preferably used are anthracene, tetracene, heptacene, hexacene and phenanthrene.

[0034] The aromatic heterocondensed ring in which the aromatic heterocycle is condensed, or the aromatic hydrocarbon ring and the aromatic heterocycle are condensed includes benzimidazole ring, indole ring, benzimidazo Ring, benzothiazole ring, benzoxazole ring, quinoxaline ring, quinazoline ring, phthalazine ring, force rubazole ring, carboline ring, diaza force rubazole ring (one of the carbon atoms of the hydrocarbon ring constituting the carboline ring) And a ring substituted with a nitrogen atom).

In addition, the aromatic hydrocarbon condensed ring or aromatic heterocyclic ring condensed with the above aromatic hydrocarbon ring or aromatic heterocyclic ring may be unsubstituted or may have a substituent. Is an alkyl group (for example, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, pentyl group, hexyl group, octyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, etc.), cycloalkyl Groups (for example, cyclopentyl group, cyclohexyl group, etc.), alkenyl groups (for example, vinyl group, allyl group, etc.), alkyl groups (for example, ethynyl group, propargyl group, etc.), aryl groups (for example, phenyl) Group, naphthyl group, etc.), aromatic heterocycle (for example, furyl group, chael group, pyridyl group, pyridazyl group, pyrimidinyl group, pyrajuryl group, triazinyl group) Group, imidazolyl group, pyrazolyl group, thiazolyl group, quinazolinyl group, phthaladyl group, etc.), heterocyclic group (eg, pyrrolidyl group, imidazolidyl group, morpholyl group, oxazolidyl group, etc.), alkoxy group (eg, methoxy group, ethoxy group) Group, propyloxy group, pentyloxy group, hexyloxy group, octyloxy group, dodecyloxy group, etc., cycloalkoxy group (for example, cyclopentyloxy group, cyclohexyloxy group, etc.), aryloxy group (for example, phenoxy group, naphthyloxy group, etc.) Etc.), alkylthio group (eg, methylthio group, ethylthio group, propylthio group, pentylthio group, hexylthio group, octylthio group, dodecylthio group, etc.), cycloalkylthio group (eg, cyclopentylthio group, cyclohexylthio group, etc.) Arylthio group (for example, phenylthio group, naphthylthio group, etc.), alkoxycarbonyl group (for example, methyloxycarbonyl group, ethyloxycarbonyl group, butyloxycarbonyl group, octyloxycarbon group) Group, dodecyloxycarbon group, etc.), aryloxycarbonyl group (eg, phenylcarbol group, naphthyloxycarbonyl group, etc.), sulfamoyl group (eg, aminosulfol group, methylaminosulfo group, etc.) -Luyl group, dimethylaminosulfol group, butylaminosulfol group, hexylaminosulfol group, cyclohexylaminosulfol group, octylaminosulfol group, dodecylamino Nosulfol group, phenolaminosulfol group, naphthylaminosulfol group, 2-pyridylaminosulfol group, etc.), acyl group (for example, acetyl group, ethylcarbol group, propylcarbol group, Pentyl carbo yl, cyclohexyl carbo yl, octyl carbo yl, 2-ethyl hexyl carbo ol, dodecyl carbo ol, phenol carbo yl, naphthyl carb ol, pyridyl carbo ol Group), an acyl group (eg, acetyloxy group, ethylcarbo-oxy group, butyl carboxy-oxy group, octyl carboxy-oxy group, dodecyl carboxy-oxy group, phenyl carbonyloxy group, etc.), an amide group (eg, methyl carbo-oxy group) Ruamino group, ethyl carbo amino group, dimethyl carbolumino group, propyl carbolumino group, pentylca Rubo-lumino group, cyclohexyl carbo-lumino group, 2-ethylhexyl carboamino group, octyl carbolumino group, dodecyl carbo-lumino group, vinyl carboxyamino group, naphthylcarbonylamino group, etc.) Rubamoyl groups (e.g. aminoamino groups, methylaminocarboxylic groups, dimethylaminocarboxylic groups, propylaminocarboxylic groups, pentylaminocarboxylic groups, cyclohexylaminocarboxylic groups) Group, octylaminocarbol group, 2-ethylhexylaminocarbol group, dodecylaminocarbole group, phenolaminocarbol group, naphthylaminocarbol group, 2-pyridylaminocarbol group Etc.), ureido group (for example, methylureido group, ethylureido group, pentylureido group, cyclohexylureido group, octyl) Ureido group, dodecylureido group, phenol-ureido group naphthylureido group, 2-pyridylaminoureido group, etc.), sulfier group (eg methylsulfyl group, ethylsulfuryl group, butylsulfuryl group, cyclohexylsulfyl group) 2-ethylhexylsulfyl group, dodecylsulfuryl group, phenylsulfyl group, naphthylsulfuryl group, 2-pyridylsulfyl group, etc.), alkylsulfol group (for example, methylsulfol group) , Ethylsulfyl group, butylsulfol group, cyclohexylsulfol group, 2-ethylhexylsulfol group, dodecylsulfol group, etc.), arylsulfol group (phenylsulfol group, naphthylsulfol group) Group, 2-pyridylsulfol group, etc.), amino group (for example, amino group, ethylamino group, dimethyl group) Amino groups, Buchiruamino group, cyclopentyl Rua amino group, alkoxy Ruamino group to 2-Echiru, Dodeshiruamino group, § - Rinomoto, Nafuchiruamino group, 2-Pirijiruamino group) Halogen atoms (eg fluorine atom, chlorine atom, bromine atom, etc.), fluorohydrocarbon groups (eg fluoromethyl group, trifluoromethyl group, pentafluoroethyl group, pentafluorophenyl group, etc.), cyano Group, nitro group, hydroxy group, mercapto group, silyl group (for example, trimethylsilyl group, triisopropylpropyl silyl group, triphenylsilyl group, ferroethylsilyl group, etc.).

 [0036] These substituents may be further substituted with the above-described substituents. In addition, a plurality of these substituents may be bonded to each other to form a ring.

 [0037] L represents a linking group bonded with a conjugated system including an aromatic hydrocarbon ring or an aromatic heterocyclic ring.

 [0038] Examples of the aromatic hydrocarbon ring include a benzene ring, a biphenyl ring, a naphthalene ring, an azulene ring, an anthracene ring, a phenanthrene ring, a pyrene ring, a thalylene ring, a naphthacene ring, a triphenylene ring, and o-terfene ring. Ring, m-terfel ring, p-terfel ring, acenaphthene ring, coronene ring, fluorene ring, fluoranthrene ring, naphthacene ring, pentacene ring, perylene ring, pentaphen ring, picene ring, pyrene ring, Examples include a pyranthrene ring and anthraanthrene ring. Of these, a benzene ring is preferably used. Further, these aromatic hydrocarbon rings may be unsubstituted or have a substituent. Examples of the substituent include an aromatic hydrocarbon ring in which two or more of the aforementioned rings are condensed, and 2 Examples of the substituent include those described for the aromatic heterocyclic ring in which two or more rings are condensed.

 [0039] Examples of the aromatic heterocycle include furan ring, thiophene ring, pyridine ring, pyridazine ring, pyrimidin ring, pyrazine ring, triazine ring, benzimidazole ring, oxadiazole ring, triazole ring, imidazole ring, pyrazole ring, Carbon atom of the hydrocarbon ring constituting the thiazole ring, indole ring, benzimidazole ring, benzothiazole ring, benzoxazole ring, quinoxaline ring, quinazoline ring, phthalazine ring, force rubazole ring, carboline ring, carboline ring Examples include a ring in which at least one is further substituted with a nitrogen atom.

[0040] (Compound represented by formula (2))

The organic semiconductor material of the present invention is characterized by containing a compound represented by the above general formula (1) or (2). [0041] The compound represented by the general formula (2) according to the present invention will be described.

 [0042] In the general formula (2), Ar and Ar represent a hydrogen atom or a substituent, and Ar and Ar

 At least one of 21 22 21 22 is an aromatic hydrocarbon condensed ring or an aromatic hetero condensed ring condensed with an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and R

 21 and R

 22 represents a hydrogen atom or a substituent, and L is bonded with a conjugated system including an aromatic hydrocarbon ring or an aromatic heterocyclic ring.

 twenty one

 Represents a linking group.

 [0043] An aromatic charcoal in which an aromatic hydrocarbon ring or an aromatic heterocycle represented by Ar or Ar is condensed

 21 22

 The hydrogen fluoride condensed ring or the aromatic hetero condensed ring is represented by Ar or Ar in the general formula (1).

 It is synonymous with an aromatic hydrocarbon condensed ring or an aromatic hetero condensed ring condensed with an aromatic hydrocarbon ring or an aromatic heterocyclic ring.

[0044] The substituent represented by R and R is an aromatic group in which two or more rings of the general formula (1) are condensed.

 21 22

 It is synonymous with a substituent of an aromatic heterocyclic ring in which an aromatic hydrocarbon ring and two or more rings are condensed.

[0045] Bonded with a conjugated system containing an aromatic hydrocarbon ring or an aromatic heterocycle represented by L

 twenty one

 The linking group is synonymous with the linking group L bonded through a synergistic system containing the aromatic hydrocarbon ring or aromatic heterocycle of the general formula (1).

[0046] Regarding the compound represented by the general formula (2), both Ar and Ar have two or more rings.

 21 22

 It is preferably a condensed aromatic hydrocarbon ring or an aromatic heterocyclic ring in which two or more rings are condensed.

 [0047] The weight molecular weight of the compound represented by the general formula (1) or (2) is preferably 10,000 or less, and more preferably in the range of 100 to 5,000. By limiting the molecular weight to this range, the stackability and orientation between molecules can be improved, a film in which molecules are regularly arranged can be produced, and the TFT performance can be improved. The weight average molecular weight or number average molecular weight of the organic semiconductor material of the present invention is measured using GPC (gel permeation chromatography) using tetrahydrofuran as a column solvent.

 The compound represented by the general formula (1) or (2) preferably has a partial structure represented by the general formula (3).

[0048] Further, L in the general formula (1) or L in the general formula (2)

 twenty one

It is preferable to have a partial structure represented by the formula (3). Having such a partial structure This improves the stackability of molecules and improves the TFT performance.

[0049] In the general formula (3), Ar to Ar are an aromatic hydrocarbon ring or an aromatic heterocyclic ring.

 31 33

 , R is a substituent, and R 1 and R 2 represent a hydrogen atom or a substituent.

 31 32 33

 [0050] The aromatic hydrocarbon condensed ring or the aromatic heterocyclic condensed ring represented by Ar to Ar is the above-mentioned

 31 33

 The substituent represented by R 1, R 2 and R 3 is synonymous with the aromatic hydrocarbon ring or aromatic heterocycle described for the linking group L in the general formula (1), and the substituent represented by R 1, R 2 and R 3 is the aromatic carbon ring of the general formula (1). water

 31 32 33

 It is synonymous with the substituent of the aromatic hydrocarbon condensed ring or aromatic heterocyclic condensed ring in which the elemental ring or aromatic heterocyclic ring is condensed.

[0051] L in the general formula (1) or L in the general formula (2) is substituted or unsubstituted.

 twenty one

 It is preferred to have a substituted thiophene ring.

[0052] L or L is a partial structure in which two or more substituted or unsubstituted thiophene rings are linked.

 twenty one

 The number of thiophene rings contained in L or L is 2 to 40.

 twenty one

 More preferably, it is 3-20, and more preferably 4-10. The compound represented by the general formula (1) or (2) preferably has a partial structure represented by the general formula (4).

[0053] More preferably, the L or L force has a partial structure represented by the general formula (4).

 twenty one

 It is.

[0054] In the general formula (4), R represents a substituent. Examples of the substituent include an alkyl group (for example, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, pentyl group, hexyl group, octyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group). Group), cycloalkyl group (eg, cyclopentyl group, cyclohexyl group, etc.), alkenyl group (eg, vinyl group, aryl group, etc.), alkynyl group (eg, ethynyl group, propargyl group, etc.), aryl Group (e.g., phenyl group, p-chlorophenyl group, mesityl group, tolyl group, xylyl group, naphthyl group, anthryl group, azulenyl group, acenaphthyl group, fluoride group, phenanthryl group, indur group, pyrethyl group) Group, bif ヱ -ryl group, etc.), aromatic heterocycle (eg furyl group, chenyl group, pyridyl group, pyridazyl group, Mijiru group, Birajiru group, triazyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, Benzoimi Dazoriru group, benzo O hexa benzotriazolyl group, quinazolyl group, phthalazyl group), a Hajime Tamaki (eg Pyrrolidyl group, imidazolidyl group, morpholyl group, oxazolidyl group, etc.), alkoxy group (for example, methoxy group, ethoxy group, propyloxy group, pentyloxy group, hexyloxy group, octyloxy group, dodecyloxy group, etc.), cycloalkoxy group ( For example, cyclopentyloxy group, cyclohexyloxy group, etc.), aryloxy group (eg, phenoxy group, naphthyloxy group, etc.), alkylthio group (eg, methylthio group, ethylthio group, propylthio group, pentylthio group, hexylthio group) Group, octylthio group, dodecylthio group, etc.), cycloalkylthio group (for example, cyclopentylthio group, cyclohexylthio group, etc.), arylthio group (for example, furylthio group, naphthylthio group, etc.), alkoxycarbonyl group (for example, For example, methylo Xyloxy group, ethyoxycarbol group, butyloxycarbol group, octyloxycarbol group, dodecyloxycarbol group, etc.), aryloxycarboro group (For example, phenylcarbol group, naphthyloxycarol group, etc.), sulfamoyl group (for example, aminosulfol group, methylaminosulfol group, dimethylaminosulfol group, butylaminosulfol group) Group, hexylaminosulfol group, cyclohexylaminosulfol group, octylaminosulfol group, dodecylaminosulfol group, phenolaminosulfol group, naphthylaminosulfol group, 2 —Pyridylaminosulfol group, etc.), acyl group (eg, acetyl group, ethyl carbonate group, propyl carbon group, pentyl carbonate group, cyclohexyl carbon group, octyl group) A carboxy group, a 2-ethylhexyl carbo yl group, a dodecyl carbo ol group, a vinyl carbo ol group, a naphthyl carbo ol group, a pyridyl carbo ol group, etc.), an acyloxy group (for example, an acetyloxy group, Ethyl carbo-loxy group, Butyl carbo-loxy group, Octyl carbo- loxy group, Dodecyl carbonyloxy group, Phenol carbonyloxy group, etc.) Amide group (for example, methylcarbonylamino group, ethylcarbo-lamino group, dimethylcarboxyl group) -Luamino group, propyl carbolumino group, pentyl carbolumino group, cyclohexyl carbolumino group, 2-ethyl hexyl carbolumino group, octyl carbolumino group, dodecyl carbolumino group, phenol carbolumino group , Naphthylcarbo-amino groups, etc.), rubamoyl groups (eg amino Carbo - group, methyl § amino carbo - group, dimethyl § amino carbo - group, flop port pills aminocarboxy - group, pentyl Rua amino carbo - group, hexyl § amino carbonitrile cyclohexane Group, octylaminocarbol group, 2-ethylhexylaminocarbol group, dodecylaminocarbol group, phenolaminocarbol group, naphthylaminocarbol group, 2-pyridyl Aminocarbole group, etc.), ureido group (for example, methylureido group, ethylureido group, pentylureido group, cyclohexylureido group, octylureido group, dodecylureido group, phenolureido group, naphthylureido group, 2- Pyridylaminoureido group, etc.), sulfier groups (for example, methylsulfuryl group, ethylsulfyl group, butylsulfuryl group, cyclohexylsulfuryl group, 2-ethylhexylsulfuryl group, dodecylsulfuryl group, phenol) -Rulsulfyl group, naphthylsulfuryl group, 2-pyridylsulfyl group, etc.), alkylsulfol group ( For example, a methylsulfol group, an ethylsulfol group, a butylsulfol group, a cyclohexylsulfol group, a 2-ethylhexylsulfol group, a dodecylsulfol group, etc.), an arylsulfol group (for example, A phenylsulfol group, a naphthylsulfol group, a 2-pyridylsulfol group, etc.), an amino group (for example, an amino group, an ethylamino group, a dimethylamino group, a butylamino group, a cyclopentylamino group, a 2-ethylhexylamino group, Dodecylamino group, arlino 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, etc.) Group, pentafluoroethyl group, pentafluorophenyl group, etc.), cyan group, silyl group (for example, trimethyl) Silyl group, tri-isopropyl building silyl group, triflate - Rushiriru group, full - Rujechirushiri Le group). Among these, R is preferably an alkyl group or an alkoxy group.

 [0055] These substituents may be further substituted with the above-described substituents, or a plurality thereof may be bonded to each other to form a ring.

[0056] The thiophene oligomer according to the present invention preferably has no head-to-head structure in the structure, more preferably a head-to-tail structure or a Tai 1 to-tail structure. It is to have. For the head-to-head structure, head-to-tail structure, and tail-to-tail structure according to the present invention, for example, “π-electron organic solids” (1998, published by the Japan Society of Chemistry) 27-32 pages, Adv. Mater. 1998, 10, No. 2, pages 93-116, etc. Hereinafter, specific examples of the compound represented by the general formula (1) or (2) according to the present invention will be shown, but the present invention is not limited thereto.

[0058] [Chemical 4]

[0059] [Chemical 5]

[9 ^] [0900]

[ΐ9οο]

[ΐ9οο]

lllC0C / 900Zdf / X3d 61 · 860 / 900Ζ OAV

[] [2900]

TllC0C / 900Zdf / X3d 03 ΪΖΪ860 / 900Ζ OAV

[6 ^] [S900]

TllC0C / 900Zdf / X3d ΪΖΪ860 / 900Ζ OAV

[Οΐ ^] 900]

TllC0C / 900Zdf / X3d zz ΪΖΪ860 / 900Ζ OAV [π¾] [S900]

TllC0C / 900Zdf / X3d ΪΖΪ860 / 900Ζ OAV

[0066] [Chemical 12]

[ετ ^] [900]

lllf0f / 900ldf / 13d 93 ΙΠ860 / 900Ζ ΟΛ

[fl ^] [8900]

Ul £ 0 £ / 900Zd £ / 13d 93 IJ1860 / 900Z OAV

[0069] Synthesis examples of these compounds are shown below.

[0070] (Synthesis of Compound 12)

 Compound 12 was synthesized according to the following scheme.

[0071] [Chemical 15]

<Synthesis of Intermediate 2>

Intermediate synthesized according to J. Phys. Chem., 99, 10, 1995, 3218-3224 was dissolved in a mixed solvent of 240 ml of dichloromethane and 120 ml of acetic acid, and 2 g of N-bromosuccinimide was added in portions at room temperature. . After stirring under reflux for 3 hours, the reaction mixture obtained by returning to room temperature was washed with 5 mass% aqueous potassium hydroxide solution, water and saturated brine. After the solvent was distilled off, the target product was isolated by column chromatography to obtain 3.8 g of intermediate 2. Rate 55%).

 <Synthesis of Compound 12>

Under a nitrogen atmosphere, Intermediate 2 1. 2 g in 40 ml of THF, Intermediate 3 2 g, tetrakis (triflates E - Le phosphine) palladium 0. 3 g, 20 weight _^0/0 aqueous solution of potassium carbonate lml the a (0) Karoe The mixture was stirred for 72 hours under reflux. The obtained reaction mixture was washed with water and saturated brine, the solvent was evaporated, and 0.5 g of Compound 12 was obtained by column chromatography (yield 19%). The molecular structure of the resulting compound 12 was confirmed by 1H-NMR (nuclear magnetic resonance spectrum) and mass spectral measurement to be consistent with the target product. Furthermore, it was confirmed that the purity was 99% or more from the result of HPLC measurement.

 [0074] Other compounds can be synthesized in the same manner.

 [Organic Semiconductor Film, Organic Semiconductor Device, Organic Thin Film Transistor, and Organic Thin Film Transistor Forming Method]

 The method for forming the organic semiconductor film, organic semiconductor device, organic thin film transistor, and organic thin film transistor of the present invention will be described.

 [0076] By using the organic semiconductor material of the present invention for the semiconductor layer of an organic semiconductor film, an organic semiconductor device, or an organic thin film transistor, an organic semiconductor device and an organic thin film transistor that are driven well can be provided. An organic thin film transistor has a source electrode and a drain electrode connected with an organic semiconductor as a semiconductor layer on a support, a top gate type having a gate electrode on the gate electrode via a gate insulating layer, and a support. First, it is roughly divided into a bottom gate type having a gate electrode and having a source electrode and a drain electrode connected by an organic semiconductor through a gate insulating layer.

 [0077] In order to install the organic semiconductor material of the present invention on a semiconductor layer of an organic semiconductor film, an organic semiconductor device, or an organic thin film transistor, it can be installed on a substrate by vacuum deposition.

The solution prepared by dissolving in an appropriate solvent and adding additives as necessary is preferably placed on the substrate by cast coating, spin coating, printing, ink jet method, abrasion 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 it can prepare a solution having an appropriate concentration by dissolving the organic semiconductor material. Chain ether solvents such as ethyl ether diisopropyl ether, cyclic ether solvents such as tetrahydrofuran and dioxane, keton solvents such as acetone methylethyl ketone, halogenated forms such as chloroform and 1,2-dichloroethane. Examples include alkyl solvents, toluene, aromatic solvents such as o-dichlorobenzene, nitrobenzene, and m-talezole, N-methylpyrrolidone, and carbon dioxide. Among these solvents, a solvent containing a non-halogen solvent is preferably a non-halogen solvent.

 [0079] In the organic thin film transistor of the present invention, the organic semiconductor material of the present invention is preferably used for the semiconductor layer as described above. In the method for forming an organic thin film transistor of the present invention, the semiconductor layer is preferably formed by applying a solution or dispersion containing these organic semiconductor materials. The solvent that dissolves the organic semiconductor material is preferably composed of a non-halogen solvent that is preferably a solvent containing the non-halogen solvent.

 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 bell, tantalum, indium, palladium, tellurium, rhenium, iridium, ano-remium, ruthenium, germanium, molybdenum, tungsten, tin oxide 'antimony, indium oxide' tin (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 monopotassium alloy, magnesium, Lithium, Anoleum, Mug Cium Z copper mixture, magnesium Z silver mixture, magnesium Z aluminum mixture, magnesium Z indium mixture, aluminum Z acid-aluminum mixture, lithium Z aluminum mixture, etc. are used, especially platinum, gold, silver, copper Aluminum, indium, ιτο and carbon are preferred. Alternatively, known conductive polymers whose conductivity has been improved by doping, for example, conductive polyarlin, conductive polypyrrole, conductive polythiophene, polyethylene dioxythiophene and polystyrene sulfonic acid complex, etc. are also suitably used. . Of these, those having low electrical resistance on the contact surface with the semiconductor layer are preferred.

[0081] As a method for forming the electrode, a method such as vapor deposition or sputtering using the above as a raw material is used. There are a method of forming an electrode by using a known photolithographic method and a lift-off method, and a method of etching a metal foil such as aluminum or copper using a resist by thermal transfer, ink jet or the like. Alternatively, the conductive polymer solution or dispersion, or the conductive fine particle dispersion may be directly patterned by inkjet, or may be formed from the coating film by lithography, laser abrasion, or the like. In addition, 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.

 As a gate insulating layer, various insulating films can be used. In particular, an inorganic oxide film having a high relative dielectric constant is preferable. Examples of inorganic oxides include silicon oxide, aluminum oxide, tantalum oxide, titanium oxide, tin oxide, vanadium oxide, barium strontium titanate, barium zirconate titanate, lead zirconate titanate, titanate Examples include lead lanthanum, strontium titanate, barium titanate, barium magnesium fluoride, bismuth titanate, strontium bismuth titanate, strontium bismuth tantanoate, bismuth tantalate niobate, and trioxide yttrium. Among them, preferable are silicon oxide, acid aluminum, acid tantalum, and acid titanium. Inorganic nitrides such as silicon nitride and aluminum nitride can also be suitably used.

 [0083] Examples of the method for forming the coating include vacuum deposition, molecular beam epitaxy, ion cluster beam, low energy ion beam, ion plating, CVD, sputtering, and atmospheric pressure plasma. Dry process, spray coating method, spin coating method, blade coating method, dip coating method, casting method, roll coating method, bar coating method, die coating method, and other methods by patterning such as printing and inkjet Etc., and can be used depending on the material.

 [0084] The wet process includes 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 necessary, or an oxide precursor. A so-called sol-gel method in which a solution of a body, for example, an alkoxide body is applied and dried is used. Among these, the atmospheric pressure plasma method and the sol-gel method are preferable.

[0085] A method for forming an insulating film by plasma film formation under atmospheric pressure is a process in which discharge is performed under atmospheric pressure or a pressure near atmospheric pressure, and a reactive gas is plasma-excited 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, JP-A-2000-185362, etc. Also referred to as atmospheric pressure plasma method). As a result, a highly functional thin film can be formed with high productivity.

 [0086] Further, as an organic compound film, polyimide, polyamide, polyester, polyacrylate, photo-radical polymerization system, photopower thione polymerization system photocurable resin, or copolymer containing acrylonitrile component, polybutanol, Polybulal alcohol, novolak rosin, and cyanoethyl pullulan can also be used. The wet process is preferred as a method for forming the organic compound film. An inorganic oxide film and an organic oxide film can be laminated and used together. The film thickness of these insulating films is generally 5011111 to 3111, preferably 100 nm to l μm.

 [0087] Further, the support is composed of glass or a flexible resin sheet. For example, a plastic film can be used as the sheet. Examples of the plastic film include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyethylene-sulfuride, polyarylate, polyimide, polycarbonate ( PC), cellulose triacetate (TAC), and cellulose acetate propionate (CAP). In this way, by using a plastic film, it is possible to achieve lighter weight than when a glass substrate is used, to improve portability, and to improve resistance to impact.

 Hereinafter, an organic thin film transistor using an organic semiconductor film formed using the organic semiconductor material of the present invention will be described.

FIG. 1 is a diagram showing a configuration example of an organic thin film transistor of the present invention. In FIG. 2 (a), a source electrode 2 and a drain electrode 3 are formed on a support 6 with a metal foil or the like, an organic semiconductor layer 1 made of the organic semiconductor material of the present invention is formed between the two electrodes, and the organic semiconductor layer 1 is formed thereon. An insulating layer 5 is formed, and further a gate electrode 4 is formed thereon to form an organic thin film transistor. FIG. 2B shows the organic semiconductor 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) First on the support 6 The organic semiconductor layer 1 is formed 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.

[0090] In FIG. 4 (d), 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. Then, an organic semiconductor layer 1 formed of the organic semiconductor material of the present invention is formed between the electrodes. Other configurations such as shown in (e) and (f) of FIG.

FIG. 2 is a diagram showing an example of a schematic equivalent circuit diagram of an organic thin film transistor sheet.

The organic thin film transistor sheet 10 has a large number of organic thin film transistors 11 arranged in a matrix. 7 is a gate bus line of each organic thin film transistor 11, and 8 is a source bus line of each organic thin film transistor 11. An output element 12 is connected to the source electrode of each organic thin film transistor 11, and this output 12 is, for example, a liquid crystal, an electrophoretic element or the like, and constitutes a pixel in the display device. The pixel electrode may be used as the input electrode of the photosensor. In the illustrated example, the liquid crystal is shown as an output element in an equivalent circuit having resistance and capacitor power. 13 is a storage capacitor, 14 is a vertical drive circuit, and 15 is a horizontal drive circuit. Example

 Hereinafter, the present invention will be described in detail with reference to examples, but the present invention is not limited thereto.

 [0094] Examples

 (Preparation of organic thin film transistor 1)

 A 200-nm-thick thermal oxide film was formed on a Si wafer with a specific resistance of 0.01 Ω'cm as the gate electrode to form a gate insulating layer, followed by surface treatment with octadecyltrichlorosilane.

 [0095] A coated film of comparative compound 1 (poly (3-hexylthiophene), regioregular, Aldrich, average molecular weight 89000, PHT) was applied using an applicator and allowed to dry naturally to form a cast film ( And a heat treatment was performed 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 a source electrode and a drain electrode. Source and drain electrodes are 100 m wide, 200 nm thick, and channel width W An organic thin film transistor 1 having a thickness of 3 mm and a channel length L of 20 μm was fabricated.

[0097] (Preparation of organic thin film transistors 2 and 3)

 In the production of the organic thin film transistor 1, the organic thin film transistors 2 and 3 were respectively prepared in the same manner except that the comparative compound 1 was changed to comparative compounds 2 and 3 (Pentacene, Aldrich commercial reagent was used after sublimation purification). Was made.

[0098] [Compound 16] Comparative compound 1 Comparative compound 2

比較化合物 3

Comparative compound 3

[0099] (Production of organic thin film transistors 4-9)

 Organic thin film transistors 4 to 9 were produced in the same manner as in the production of the organic thin film transistor 1, except that the organic semiconductor material of the present invention described in Table 1 was used instead of the comparative compound 1. All of the molecular weights of the organic semiconductor materials of the present invention were 10,000 or less.

 [0100] (Evaluation of carrier mobility and ONZOFF value)

 With respect to the obtained organic thin film transistors 1 to 9, the carrier mobility and ON / OFF value of each element were determined immediately after fabrication and after being left in the atmosphere for 1 month. In the present invention, the saturation region force carrier mobility of the IV characteristic is obtained, and further, the ONZOFF ratio is obtained from the ratio of the drain current value when the drain bias is 50 V and the gate bias is 50 V and 0 V.

 [0101] The results obtained are shown in Table 1.

[0102] [Table 1] Immediately after fabrication After Rikitsu S

 Organic TFT Organic semiconductor

 Element No. Mobility Mobility Remarks

 Material ON / OFF value ON / OFF value

 (cnVVsec)

1 Comparative compound 1 t .0X10— ² 1.2X10 ³ 2.0X1CT ¹ 1.1 X10 'Comparative example

2 Comparative compound 2 6.8X10 " ³ 4.2X10 ⁵ 1.5X10" ⁴ 3.2X10 ⁴ Comparative example

3 Comparative compound 3 3.2X10 " ⁵ 2.2X10 ¹ Unmeasurable Unmeasurable Comparative example

4 Exemplary compounds 9 2.7X10 " ¹ 4.5X10 ⁵ 2.1 X10"'4.3X10 ^{5 The} present invention

5 Exemplary compounds 12 2,2Χί0 ^_1 5.0X10 ⁵ 1.4X10— ¹ 4.8X10 ^{5 The} present invention

6 Exemplary compounds 18 3.8X10 " ¹ 4.8X10 ⁵ 3.2X1CT '4.4X10 ^{5 The} present invention

7 Exemplified compound 23 1,5X10 "'4.6X10 ⁵ 0.9X1CT ¹ 4.0X10 ⁵

8 Exemplified Compound 26 2.0X10- ¹ 4.2X10 ⁵ 1.4X10 one ¹ 3.7 × 10 ⁵ invention

9 Exemplary compounds 0 2.5X10— '4.7X10 ⁵ 1.9X10 "' 4.0X10 ⁵ Present invention From Table 1, the organic semiconductor material of the present invention is used in comparison with the comparative organic thin film transistor fabricated using the comparative organic semiconductor material. It can be seen that the organic thin film transistors 4 to 9 produced in this way have excellent transistor characteristics even immediately after production and have high durability with little deterioration with time.

Claims

The scope of the claims  [1] An organic semiconductor material comprising a compound represented by the following general formula (1):  General formula (1) Ar -L-Ar  1 2  (In the formula, Ar and Ar represent a hydrogen atom or a substituent, and at least one of Ar and Ar is  1 2 1 2 Aromatic hydrocarbon condensed ring or aromatic heterocyclic condensed ring condensed with aromatic hydrocarbon ring or aromatic heterocyclic ring, L is bonded with a conjugated system containing aromatic hydrocarbon ring or aromatic heterocyclic ring Represents a linking group. ) [2] Aromatic carbon in which Ar and Ar are condensed with an aromatic hydrocarbon ring or an aromatic heterocyclic ring  1 2  2. The organic semiconductor material according to claim 1, which is a hydrogen fluoride condensed ring or an aromatic hetero condensed ring.  [3] An organic semiconductor material comprising a compound represented by the following general formula (2): [Chemical formula 1] General formula>

(Wherein Ar and Ar represent a hydrogen atom or a substituent, and at least one of Ar and Ar  21 22 21 22  Is an aromatic hydrocarbon condensed ring or an aromatic hetero condensed ring condensed with an aromatic hydrocarbon ring or an aromatic hetero ring, R and R represent a hydrogen atom or a substituent, and L is an aromatic  21 22 Represents a linking group bonded through a conjugated system containing a group 21 hydrocarbon ring or aromatic heterocycle. Aromatic charcoal in which Ar and Ar force aromatic hydrocarbon rings or aromatic heterocycles are condensed 21 22  4. The organic semiconductor material according to claim 3, which is a hydrogen fluoride condensed ring or an aromatic hetero condensed ring.  The organic semiconductor material according to any one of claims 1 to 4, wherein the compound represented by the general formula (1) or (2) has a molecular weight of 10,000 or less. 6. The compound according to any one of claims 1 to 5, wherein the compound represented by the general formula (1) or (2) has a partial structure represented by the following general formula (3). Organic half as described in Conductor material.  [Chemical 2] General formula (3)

(In the formula, Ar to Ar are aromatic hydrocarbon rings or aromatic heterocyclic rings, and R is a substituent.  31 33 31 and R and R represent a hydrogen atom or a substituent. )  32 33  [7] L in the general formula (1) or L 1S in the general formula (2) In the general formula (3)  twenty one  The organic semiconductor material according to any one of claims 1 to 5, wherein the organic semiconductor material has a partial structure represented. [8] L in the general formula (1) or L in the general formula (2) or unsubstituted  twenty one  6. The organic semiconductor material according to claim 1, comprising a thiophene ring.  [9] L in the general formula (1) or L force in the general formula (2) Substituted or unsubstituted  twenty one  6. The organic semiconductor material according to claim 1, wherein the organic semiconductor material has a partial structure in which two or more thiophene rings are connected. [10] The compound according to any one of claims 1 to 5, wherein the compound represented by the general formula (1) or (2) has a partial structure represented by the following general formula (4): Or the organic semiconductor material according to item 1.  [Chemical 3] —General formula (4>

(In the formula, R represents a substituent.) L in the general formula (1) or L force in the general formula (2) In the general formula (4) The organic semiconductor material according to any one of claims 1 to 5, wherein the organic semiconductor material has a partial structure represented. [12] An organic semiconductor film comprising the organic semiconductor material according to any one of claims 1 to 11. [13] An organic semiconductor device characterized by using the organic semiconductor material according to any one of claims 1 to 11. [14] An organic thin film transistor, wherein the organic semiconductor material according to any one of claims 1 to 11 is used for a semiconductor layer. [15] The organic thin film transistor, wherein the semiconductor layer is formed by applying a solution or a dispersion containing the organic semiconductor material according to any one of claims 1 to 11. Forming method.