WO2007123030A1

WO2007123030A1 - Organic semiconductor material, organic semiconductor film, organic semiconductor device, and organic thin film transistor

Info

Publication number: WO2007123030A1
Application number: PCT/JP2007/057956
Authority: WO
Inventors: Rie Katakura; Hidekane Ozeki; Yasushi Okubo
Original assignee: Konica Minolta Holdings, Inc.
Priority date: 2006-04-19
Filing date: 2007-04-11
Publication date: 2007-11-01
Also published as: JP2007288034A; JP5157079B2

Abstract

Disclosed is a molecular design of an organic semiconductor material which is useful for thin film transistors. Also disclosed are an organic semiconductor film, an organic semiconductor device and an organic thin film transistor respectively using the designed organic semiconductor material and exhibiting high carrier mobility, high ON/OFF ratio and high durability (improved oxidation stability and long-term stability). Specifically disclosed is an organic semiconductor material containing a compound having a partial structure composed of an aromatic fused polycyclic ring wherein three or more rings are fused. This organic semiconductor material is characterized in that the aromatic fused polycyclic ring has three or more substituents represented by the following general formula (1).

Description

Specification

Organic semiconductor materials, organic semiconductor films, organic semiconductor devices, and organic thin film transistors

Technical field

The present invention relates to an organic semiconductor material, an organic semiconductor film, an organic semiconductor device, and 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, information that has been provided in paper media has been increasingly digitized, and electronic paper is a display media 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 not only charge transport materials for organic EL devices, but also organic laser oscillation devices (see Non-Patent Document 1, for example) and organic thin film transistor devices (organic TFT devices) reported in many papers. (See, for example, Non-Patent Document 2.) ₀

[0008] If these organic semiconductor devices can be realized, a relatively low !, vacuum at temperature! /, Simplification of the manufacturing process by low-pressure vapor deposition, and appropriate improvement of the molecular structure can be achieved. It is thought that there is a possibility of obtaining a semiconductor that can be used, and manufacturing by a printing method including an ink jet method by inking an organic semiconductor solution is also conceivable. 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, so the aforementioned restrictions on substrate heat resistance are relaxed. For example, a TFT element may be formed on a 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. Will be difficult to crack)) [0009] However, as organic semiconductors for realizing such TFT elements, the acenes such as pentacene and tetracene have been studied so far (see, for example, 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 typically represented by thiophene hexamer called oc-chenyl or sexithiophene (for example, see Patent Document 3) ), Naphthalene, anthracene and a compound in which a 5-membered aromatic heterocyclic ring is condensed symmetrically (for example, see Patent Document 4), a modified oligo and a polydithienopyridine (for example, see Patent Document 5), Polythiophene, polyethylene biylene, poly-p-phenylene birene, and conjugated polymers are limited. A material exhibiting sufficient carrier mobility and ONZOFF ratio has been found while maintaining sufficient solubility in a solvent that can only be achieved with other types of compounds (for example, see Non-Patent Documents 1 to 3). Nah ...

[0010] Recently, very high mobility has been reported by a single crystal of rubrene, which is a highly soluble acene (see, for example, Non-Patent Document 4), but a rubrene film formed by solution casting. Does not have such a single crystal structure, and sufficient mobility is not obtained. In addition, it has been reported that high V carrier mobility and excellent semiconductor device characteristics are exhibited! Pentacene has a problem that it is insoluble or hardly soluble in organic solvents. In order to improve this point, compounds including functional groups added to pentacene have been disclosed, and it has been reported that relatively good carrier mobility can be obtained by solution coating (for example, patents). (Ref. 6).

[0011] As a result, these acene compounds such as rubrene and pentacene are easily oxidized by air and converted into oxidants and dimers such as endoperoxide, and as field effect transistors. It is known that the performance is greatly deteriorated, and there are still problems to be solved regarding the storage stability in solution and the stability of the coating film. Examples of acene-based compounds that are relatively stable with respect to acids include some compounds that are substituted with silylethynyl groups at positions 6 and 13 of pentacene and positions 5 and 11 of anthradithiophene. (For example, see non-patent documents 5, 6, 7 and patent document 7.)

) o [0012] However, in these reports, the qualitative properties are only described as stability against acid and soot is improved. V, stability that can still withstand practical use is not obtained. Being! /,Absent.

[0013] Accordingly, a novel charge transporting material that is dissolved in a solvent having process suitability at a high concentration, has sufficient carrier mobility, onZoff ratio, and further has stability in a solution state. The development of a semiconducting composition using bismuth is awaited.

[0014] However, in the above-mentioned document, the compound is not studied as a semiconductor material, and only its usage is illustrated, and sufficient TFT performance is obtained.

[0015] Therefore, a novel charge transporting material that is dissolved in a solvent having process suitability at a high concentration, has sufficient carrier mobility, on Zoff ratio, and further has stability in a solution state. The development of semiconducting compositions using materials is awaited.

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: Pamphlet of International Publication No. 03Z016599

Patent Document 7: US Pat. No. 6690029 Specification

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

Non-Patent Document 4: Science, 2004, 303, 5664, 1644-1646

Non-Patent Document 5: Org. Lett., Vol. 4 (2002), p. 15

Non-Patent Document 6: J. Am. Chem. Soc., Vol. 127 (2005), p. 4986

Non-Patent Document 7: Adv. Mater., Vol. 15 (2003), 2009

Disclosure of the invention Problems to be solved by the invention

An object of the present invention is to molecularly design an organic semiconductor material useful for thin film transistor applications, and to use the obtained organic semiconductor material to exhibit high carrier mobility, a high ONZOFF ratio, and high durability ( It is to provide an organic semiconductor film, an organic semiconductor device, and an organic thin film transistor having both oxidation stability and stability over time. Means for solving the problem

[0017] The above object of the present invention has been achieved by the following configurations 1 to 17.

[0018] 1. For an organic semiconductor material containing a compound having, as a partial structure, an aromatic condensed polycycle in which three or more rings are condensed,

An organic semiconductor material characterized in that the aromatic condensed polycycle has three or more substituents represented by the following general formula (1).

[0019] [Chemical 1]

—General formula (1)

R—≡ ~ *

[Wherein R represents a hydrogen atom, a halogen atom or a substituent, and a plurality of R may be the same or different. * Represents a bonding site with the aromatic condensed polycycle. ]

2. The organic semiconductor material as described in 1 above, wherein the aromatic condensed polycycle contains at least one partial structure represented by the following general formula (2)!

[0021] [Chemical formula 2] General formula (2)

[In the formula, R and R each represent a hydrogen atom, a halogen atom or a substituent. However, R

1 2

May be the same or different, and the Rs may be the same or different.

1 2

]

3. The aromatic condensed polycycle contains two or more partial structures represented by the general formula (2)

3. The organic semiconductor material as described in 2 above, which is V.

[0023] 4. The organic semiconductor material as described in any one of 1 to 3 above, which comprises a compound having a partial structure represented by the following general formula (3).

[0024] [Chemical formula 3] General formula (3)

[Wherein, R to R each represents a hydrogen atom, a halogen atom or a substituent. nl to n3 are 0

3 6

It represents the integer above, 2≤nl + n2 + n3≤5. ]

5. R in the general formula (1), R and R in the general formula (2), R to R force in the general formula (3)

1 2 3 6

A cycloalkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, Si () or Ge () (where R ′ represents a substituent).

3 3

5. The organic semiconductor material according to any one of 1 to 4 above, wherein

[0026] 6. R in the general formula (1), R and R in the general formula (2), R to R force in the general formula (3)

1 2 3 6

Aromatic hydrocarbon ring group, aromatic heterocyclic group, Si (R ') or Ge (R') (R 'is a substituent

3 3

Represents. 6. The organic semiconductor material as described in 5 above, wherein

[0027] 7. R and R in the general formula (2), R to R force in the general formula (3)

1 2 3 6

The organic semiconductor material according to any one of 2 to 6, wherein the force is any one of the above 2 to 6.

[0028] 8. R in the general formula (1), R and R in the general formula (2), R to R force in the general formula (3) Aromatic coal 8. The organic semiconductor material as described in 6 or 7 above, which represents a hydrogenated ring group.

[0029] 9. The organic semiconductor material as described in 8 above, wherein the aromatic hydrocarbon ring group is a substituted phenyl group.

[0030] 10. The organic semiconductor material as described in 9 above, wherein the substitution position of the substituted phenol group is 2,6-substituted or 2,4,6-substituted.

[0031] 11. The organic semiconductor as described in 10 above, wherein the substituent in the 2,6-substituted or 2,4,6-substituted is also an alkyl group, an alkoxy group or a phenyl group. Material.

[0032] 12. The organic semiconductor material as described in any one of 8 to 11 above, wherein, in the general formula (3), nl = 1, n2 = 1, and n3 = 1.

[0033] 13. R and R in the general formula (2), R to R forces in the general formula (3), each of which is condensed with two or more rings

1 2 3 6

7. The organic semiconductor material according to any one of 2 to 6, which is an aromatic hydrocarbon ring group or an aromatic heterocyclic group.

[0034] 14. An organic semiconductor film comprising the organic semiconductor material according to any one of 1 to 13 above.

[0035] 15. It is formed by dissolving or dispersing the organic semiconductor material according to any one of 1 to 13 above in an organic solvent, and applying and drying the obtained solution or dispersion. An organic semiconductor film.

[0036] 16. An organic semiconductor device using the organic semiconductor material according to any one of 1 to 13 above.

[0037] 17. An organic thin film transistor, wherein the organic semiconductor material according to any one of 1 to 13 is used for a semiconductor layer.

The invention's effect

[0038] According to the present invention, organic semiconductor materials useful for thin film transistor applications are molecularly designed, and the resulting organic semiconductor materials exhibit high carrier mobility, a high ONZOFF ratio, and high durability ( An organic semiconductor film, an organic semiconductor device, and an organic thin film transistor having both oxidation stability and stability over time have been provided.

Brief Description of Drawings [0039] FIG. 1 is a diagram showing a configuration example of an organic TFT according to the present invention.

FIG. 2 is a diagram showing an example of a schematic equivalent circuit diagram of an organic TFT sheet.

FIG. 3 is a schematic view showing an example of a display device constituted by an organic EL element cover.

FIG. 4 is a schematic diagram of display unit A.

FIG. 5 is a schematic diagram of a pixel.

Explanation of symbols

[0040] 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 TFT sheet

11 Organic TFT

12 Output element

13 Storage capacitor

14 Vertical drive circuit

15 Horizontal drive circuit

21 display

23 pixels

25 scan lines

26 data lines

27 Power line

100 organic EL elements

110 Switching transistor

120 Ma District Motion Transistor 130 capacitors

A Display section

B Control unit

BEST MODE FOR CARRYING OUT THE INVENTION

[0041] In the organic semiconductor material of the present invention, an organic semiconductor material useful for thin film transistor applications was obtained by using the structure defined in any one of claims 1 to 13.

[0042] Using the obtained organic semiconductor material, an organic semiconductor film, an organic semiconductor device, and an organic thin film transistor (also referred to as organic TFT) exhibiting high carrier mobility and good ONZOf f characteristics were obtained. .

[0043] Further, it has been found that the organic electroluminescence device having the organic TFT of the present invention exhibits good light emission characteristics.

[0044] Details of each component according to the present invention will be sequentially described below.

[0045] << Organic Semiconductor Material >>

The organic semiconductor material according to the present invention will be described.

[0046] As a result of various investigations on the above problems, the present inventors have an aromatic condensed polycycle in which three or more rings are condensed as a partial structure, and the aromatic condensed polycycle is represented by the above general formula (1 It has been found that an organic semiconductor material containing a compound according to the present invention having three or more substituents represented by (II) has high mobility and high stability against oxidation. This is because the compound according to the present invention has, as a partial structure, an aromatic condensed polycycle having a large π-conjugated surface that is advantageous for carrier transfer, and further in a solution that is a major problem with the condensed polycyclic compound. It is also speculated that the stability of the molecule can be reduced by introducing three or more alkynyl substituents to the extent that it is sufficiently stable against acid. .

[0047] In addition, since the alkyl substituent has few elements that inhibit the π stack between aromatic rings, a highly crystalline film in which molecules are arranged more closely is formed, and as a result, the mobility of the coating film is increased. It is presumed that not only can it be made high, but also deterioration factors such as oxygen and moisture hardly permeate, forming a thin film and improving durability.

[0048] << Compound having three or more substituents represented by the general formula (1) >> According to the organic semiconductor material of the present invention, it has an aromatic condensed polycycle in which three or more rings are condensed as a partial structure, and the aromatic condensed polycycle has a substituent represented by the above general formula (1). The compounds having three or more are described.

[0049] 《Aromatic condensed polycycle》

The aromatic condensed polycycle according to the present invention will be described below.

[0050] The compound according to the organic semiconductor material of the present invention has an aromatic condensed polycycle in which three or more rings are condensed as a partial structure. Here, examples of the aromatic condensed polycycle in which three or more rings are condensed include an aromatic hydrocarbon ring and an aromatic heterocycle.

[0051] << Aromatic hydrocarbon ring condensed with 3 or more rings >>

Specific examples of aromatic hydrocarbon rings condensed with three or more rings include naphthacene ring, anthracene ring, tetracene ring, pentacene ring, hexacene ring, phenanthrene ring, pyrene ring, benzopyrene ring, benzoazulene ring, and taricene ring. , Benzochrysene ring, acenaphthene ring, acenaphthylene ring, triphenylene ring, coronene ring, benzocoronene ring, hexabenzocoronene ring, fluorene ring, benzofluorene ring, fluoranthene ring, perylene ring, naphthoperylene ring, pentabenzoperylene ring, benzoperylene Ring, pentaphen ring, picene ring, pyranthrene ring, coronene ring, naphtho coronene ring, ovalene ring, anthraanthrene ring and the like.

[0052] These rings may have a substituent represented by R in the general formula (1) described later.

[0053] << Aromatic heterocycle in which three or more rings are condensed >>

The aromatic heterocycle condensed with 3 or more rings is preferably an aromatic heterofused ring containing a hetero atom selected from N, O and S as an element constituting the condensed ring. Include atalidine ring, benzoquinoline ring, force rubazole ring, phenazine ring, phenanthridine ring, phenanthorin ring, canoleporin ring, cyclazine ring, kindlin ring, thebesin ring, cundrin ring, triphenodithiazine ring , Triphenodioxazine ring, phenanthrazine ring, acrindrin ring, anthrazine ring, perimidine ring, diazacarbazole ring (representing any one of the carbon atoms constituting the carboline ring replaced by a nitrogen atom), Phosphorus ring, dibenzofuran ring, dibenzothiophene ring, naphthofuran ring, naphthothiophene ring, Zojifuran ring, benzodioxanyl Chio Fen ring, Nafutojifuran A ring, a naphthodithiophene ring, an anthrafuran ring, an anthradifuran ring, an anthrathiophene ring, an anthradici phen ring, a thianthrene ring, a phenoxathiin ring, a di phantomylene ring (naftthiophene ring) and the like.

[0054] These rings may have a substituent represented by R in formula (1) described later.

[0055] In addition, these condensed aromatic rings are more condensed than peri condensed rings (condensed rings having atoms shared as the vertices of the three aromatic rings among the elements constituting the condensed aromatic rings). It is preferable that the ring is a condensed ring in which an aromatic ring shared by the vertices of the three aromatic rings is linearly extended. It is preferable that the acene series (condensed ring in which the aromatic rings are condensed in a straight line) is preferable to the condensed ring of the condensed ring).

[0056] Furthermore, the aromatic condensed polycycle according to the present invention is preferably those in which 3 to 8 rings are condensed, and more preferably those in which 4 to 7 rings are condensed.

[0057] In the substituent represented by the general formula (1), the substituent represented by R includes an alkyl group (for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert butyl group, a 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, Aryl group, 1 probe group, 2 butur group, 1, 3 butagel group, 2-pentyl group, isoprobel group, etc.), alkyl group (eg, ethur group, propargyl group, etc.) ), Aromatic hydrocarbon group (also referred to as aromatic carbocyclic group, aryl group, etc., for example, phenyl group, p-phenyl group, mesityl group, tolyl group, xylyl group, naphthyl group, anthryl group) , Azulenyl group, Furthyl group, fluorenyl group, phenanthryl group, indur group, pyrenyl group, bifuryl-biryl group, etc., aromatic heterocyclic group (for example, furyl group, chenyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, birazinyl group, triazinyl group) Group, imidazolyl group, pyrazolyl group, thiazolyl group, quinazolyl group, carbazolyl group, carbolinyl group, diazacarbazolyl group (one of the carbon atoms constituting the carboline ring of the carbolyl group is a nitrogen atom) ), Phthaladyl group, etc.), heterocyclic group (eg, pyrrolidyl group, imidazolidyl group, morpholyl group, oxazolidyl group, etc.), alkoxy group (eg, methoxy group, ethoxy group, propylene group). Ruoxy, pentyloxy, hexyloxy, octyloxy, dodecyloxy, etc.), cycloalkoxy (eg, cyclopentyloxy, cyclohexyloxy, etc.), aryloxy groups (eg, phenoxy, naphthyloxy, 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 A group (for example, phenylthio group, naphthylthio group, etc.), an alkoxy carbo group (for example, a methyloxy carbo yl group, an eth oxy carboxy group, a butyl oxy carbo ol group, an oct oxy carboxy group, Dodecyloxycarbonyl group, etc.) Aryloxy group (for example, phenyl group, naphthyl group, etc.), sulfamo group (for example, aminosulfol group, methylaminosulfol group, dimethylaminosulfol group) -Butyl group, butylaminosulfol group, hexylaminosulfol group, cyclohexylaminosulfol group, octylaminosulfol group, dodecylaminosulfol group, phenolaminosulfol group, Naphthylaminosulfol group, 2-pyridylaminosulfol group, etc.), acyl group (for example, acetyl group, ethylcarbol group, propylcarbol group, pentylcarbol group, cyclohexylcarbol group, octylcarporo group) -L group, 2-ethylhexylcarbol group, dodecylcarpol group, furolcarbol group, naphthylcarbonyl group, pyridylcarboro group -Yl group, etc.), acyloxy group (eg, acetyloxy group, ethylcarbonyloxy group, butylcarbonyloxy group, octylcarbonyloxy group, dodecylcarbonyloxy group, phenylcarbonyloxy group, etc.), Amido groups (e.g., methylcarboamino groups, ethylcarboamino groups, dimethylcarboamino groups, propylcarboamino groups, pentylcarboamino groups, cyclohexylcarbolamino groups, 2-ethylhexylcarbolamamino groups Group, octyl carbolumino group, dodecyl carbolumino group, full carbolumino group, naphthyl carboxy amino group, etc.), strong rubamoyl group (for example, aminocarbonyl group, methylaminocarbole group, dimethyl group) Aminocarbol group, propylaminocarbol group, pentylaminocarbole group , Cyclohexyl § amino carbo - group, O-lipped Rua amino carbo - group, hexyl § to 2 Echiru amino carbo - group, dodecyl § amino carbo - group, Hue - Ruaminokarubo - Le 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-pyridylaminoureido group, etc.), sulfier group (eg, methylsulfuryl group, ethylsulfyl group, butylsulfuryl group, cyclohexylsulfuryl group, 2-ethylhexylsulfuric group) Group, dodecylsulfuryl group, phenylsulfyl group, naphthylsulfuryl group, 2-pyridylsulfuryl group, etc.), alkylsulfol group (for example, methylsulfol group, ethylsulfol group, butylsulfol group) -Group, cyclohexylsulfol group, 2-ethylhexylsulfur Hole group, dodecyl sulfol group, etc.), aryl sulfol group or heteroaryl sulfol group (eg, phenol sulfol group, naphthylsulfonyl group, 2-pyridylsulfonyl group, etc.), Amino group (for example, amino group, ethylamino group, dimethylamino group, butylamino group, cyclopentylamino group, 2-ethylhexylamino group, dodecylamino group, linrino group, naphthylamino group, 2-pyridylamino group, etc.), halogen Atoms (eg, fluorine, chlorine, bromine, etc.), fluorocarbon radicals (eg, fluoromethyl, trifluoromethyl, pentafluoroethyl, pentafluorophenyl, etc.), cyano Group, nitro group, hydroxy group, mercapto group, — Si (R) group (where R represents a substituent, and the aromatic hydrocarbon ring or aromatic heterocyclic ring

Three

And -Ge (R) (wherein R represents a substituent, and the aromatic

Three

An aromatic hydrocarbon ring or an aromatic heterocyclic ring which may have a substituent) or a phosphono group.

[0058] These substituents may be further substituted, or a plurality of these substituents may be bonded to each other to form a ring. When the aromatic condensed polycycle according to the present invention has a plurality of substituents represented by the general formula (1), the substituents represented by R of the substituents may be the same or different. May be.

[0059] The aromatic condensed polycycle in which three or more rings are condensed as a partial structure has three substituents represented by the general formula (1). The above-mentioned compounds form a film with higher crystallinity, and as a result, not only can the mobility of the coating film be increased, but also a thin film that is difficult to permeate deterioration factors such as oxygen and moisture, resulting in durability (acid匕 stability and It is estimated that the stability over time) was improved.

[0060] Among the compounds having three or more substituents represented by the general formula (1) according to the present invention, those preferably used are the general formula (2), the general formula (3), etc. It is a compound having the partial structure represented.

[0061] << Compound containing at least one or at least two partial structures represented by the general formula (2) >>

In general formula (2), the substituents represented by R and R are the same as those in general formula (1).

1 2

It is synonymous with the substituent represented by these.

[0062] << Compound Containing Partial Structure Represented by Formula (3) >>

In the general formula (3), the substituents represented by R to R are the same as those in the general formula (1).

3 6

It is synonymous with the substituent represented by these.

[0063] Further, preferred embodiments of the compound according to the present invention are as follows (a), (b), (c) or (d):

(a) R in the general formula (1), R and R in the general formula (2), R to R force in the general formula (3)

1 2 3 6

A kill group, a cycloalkyl group, an alkyl group, an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, Si () or Ge () (where represents a substituent).

3 3

If represented

(b) R in the general formula (1), R and R in the general formula (2), R to R force in the general formula (3)

1 2 3 6

Aromatic hydrocarbon group, aromatic heterocyclic group, Si () or Ge O ^) (where R 'is

3 3

Represents a substituent. )

(c) R and R in the general formula (2) and R to R 1S in the general formula (3) are each represented by the same substituent.

1 2 3 6

If

(d) R, R in the general formula (2), R to R force in the general formula (3), each having a substituent, or

1 2 3 6

In the case where it is represented by an aromatic hydrocarbon ring group or an aromatic heterocyclic group in which two or more rings are condensed, and the like.

More preferably, the embodiment of the compound according to the present invention is represented by the following (e), (f), (g), (h) or (i).

(E) R in the general formula (1), R and R in the general formula (2), R to R force in the general formula (3) When represented by a hydrido ring group,

(f) when the aromatic hydrocarbon ring group is a substituted phenyl group,

(g) When the substituted position of the substituted phenyl group is 2,6-substituted or 2,4,6-substituted

(h) when the substituent in the 2,6-substituted or 2,4,6-substituted is selected from an alkyl group, an alkoxy group or a phenyl group,

(i) In the general formula (3), when (e), (f), (g) or (h) is satisfied and nl = 1, n2 = 1, and η3 = 1.

[0066] The substituted position of the substituted fur group may be 3,4-substituted or 3,4,5-substituted, and the substituent is preferably an alkyl group, an alkoxy group or a phenyl group.

[0067] From the above, the organic semiconductor material of the present invention containing a compound having three or more substituents represented by the general formula (1) has high durability (oxidation stability and stability over time). In addition, it has become possible to provide materials with high carrier mobility.

[0068] Specific examples of the compound relating to the organic semiconductor material of the present invention are shown below, but the present invention is not limited thereto.

[0069] [Chemical 4]

β

scoo [9 ^] [00]

S6.S0 / .00Zdf / X3d LY οεοεζ motion OAV a007

[0073] [Chemical 8]

Imperial 0s [π ^] [so-called]

S6.S0 / .00Zdf / X3d zz οεοε OAV

[0077] [Chemical 12]

[0078] [Chemical 13]

[0080] [Chemical 15]

[9ΐ ^] [1800]

S6.S0 / .00Zdf / X3d 93 οεοεζ motion OAV

[0082] The compound according to the organic semiconductor material of the present invention can be synthesized by referring to a conventionally known synthesis method. Here, a synthesis example of the exemplified compound 1 given as a specific example above is an example. As shown.

[0083] << Synthesis of Exemplified Compound 1 >>

The outline of the synthesis scheme of Exemplary Compound 1 is shown below.

[0084] [Chemical 17]

Illustrative compound 1

[0085] Commercially available 5, 7, 12, 14-pentacentetron, J. Org. Chem., Vol. 34,

Intermediate 1 was synthesized with reference to No. 6, 1969, and then Compound Example 1 was synthesized using the intermediate 1 with reference to Chem. Zentrabl., 112, 1941, pages 889.

[0086] << Organic Semiconductor Film >>

The organic semiconductor film according to the present invention will be described.

[0087] The organic semiconductor material of the present invention can be mixed with an appropriate organic solvent (described later) and used as a solution or a dispersion.

[0088] When an organic semiconductor film is produced using a solution containing the organic semiconductor material of the present invention, any organic solvent may be used, and two or more organic solvents may be mixed and used. However, it is preferable that the composition preferably contains at least one non-halogen solvent, and more preferably comprises only a non-halogen solvent.

[0089] << Solution or dispersion at room temperature >>

The organic semiconductor film of the present invention is preferably produced through a step of forming a film using a solution or dispersion at room temperature prepared by mixing the organic semiconductor material of the present invention with the organic solvent shown below. Here, a solution or dispersion at room temperature is preferably a dispersion in which a solution or dispersion is formed when an organic semiconductor material and an organic solvent are mixed under conditions of 10 ° C to 80 ° C. The liquid represents a state in which the organic semiconductor material is dispersed in the form of particles, but includes a state in which the organic semiconductor material is partially dissolved in the dispersion.

[0090] Further, as one embodiment of the dispersion, for example, it dissolves under a temperature condition of 80 ° C to form a solution, but when returned to room temperature (usually showing a temperature of around 25 ° C), the organic semiconductor material The particles, aggregates, precipitates and the like are dispersed in an organic solvent.

[0091] (Organic solvent)

The organic solvent used for the preparation of the above solution or dispersion may be a single solvent or a mixed solvent without particular limitation, but preferably a non-halogen solvent is used. Non-halogen solvents used in the present invention include aliphatic solvents such as hexane and octane, alicyclic solvents such as cyclohexane, aromatic solvents such as benzene, toluene and xylene, tetrahydrofuran and dioxane. Ether solvents such as ethylene glycol jetyl ether, anisole, benzeno retinore ethere, ethino refenore enore, diphene nore ethenore, methino tert-butyl ether, etc., ester solvents such as methyl acetate, ethyl acetate, ethilce mouth solve , Alcohol solvents such as methanol, ethanol and isopropanol, ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, 2-hexanone, 2-heptanone and 3-heptanone, other dimethylformamide, dimethylsulfoxide Sid, Jetylform Amides, 1,3 dioxolane and the like.

[0092] The organic solvent used in combination is not particularly limited, but preferable ones are methanol, ethanol, isopropanol, acetone, methyl ethyl ketone, methyl isobutyl ketone, pyrrolidone, N-methylpyrrolidone, dimethyl. Formamide, dimethylacetamide, methyl acetate, ethyl acetate, butyl acetate, methyl lactate, ethyl lactate, butyrate And methyl j8-methoxypropionate, 13 ethyl ethoxypropionate, propylene glycol monomethyl ether acetate, toluene, xylene, hexane, limonene, cyclohexane and the like. These organic solvents can be used in combination of two or more.

[0093] As the ester solvent, oxyisobutyric acid alkyl ester may be used. As oxyisobutyric acid ester, methyl α-methoxyisobutyrate, ethyl a-methoxyisobutyrate, methyl a-ethoxyisobutyrate, a-ethoxyisobutyric acid A-alkoxyisobutyric acid alkyl esters such as ethyl; j8-alkoxyisobutyric acid alkyl esters such as methyl β-methoxyisobutyrate, ethyl β-methoxyisobutyrate, methyl j8-ethoxyisobutyrate, j8-ethoxyisobutyrate; and methyl α-hydroxyisobutyrate; such as α- hydroxy I Seo acid Echiru _alpha - it includes hydroxyisobutyric esters, Tokunihi methoxyisobutyrate methyl butyrate, beta-methoxyisobutyrate methyl butyrate, beta-Etokishiiso methyl butyrate addition Wahi primary hydroxy methyl isobutyrate It can be used.

[0094] << Organic semiconductor device, organic thin film transistor (also called organic TFT) >>

The organic semiconductor device and organic thin film transistor (also referred to as organic TFT in the present application) of the present invention will be described.

[0095] The organic semiconductor material of the present invention provides an organic semiconductor device and an organic TFT that drive well when used in a semiconductor layer such as an organic semiconductor film, an organic semiconductor device, and an organic thin film transistor (organic TFT). can do.

[0096] An organic TFT (organic thin film transistor) has a source electrode and a drain electrode connected by an organic semiconductor channel as a semiconductor layer on a support, and a top having a gate electrode on the gate electrode via a gate insulating layer. A gate type and a bottom gate type having a gate electrode on a support and a source electrode and a drain electrode connected by an organic semiconductor channel through a gate insulating layer are roughly classified.

[0097] In order to install the organic semiconductor material of the present invention in the semiconductor layer of the organic TFT, it can be installed on the substrate by vacuum deposition, but it is dissolved in an appropriate solvent and an additive is added as necessary. It is preferable to place the prepared solution on the substrate by cast coating, spin coating, printing, inkjet method, abrasion method, etc. In this case, the solvent for dissolving the organic semiconductor compound according to the present invention is not particularly limited as long as the organic semiconductor compound can be dissolved to prepare a solution with an appropriate concentration. Specifically, chain ether solvents such as jetyl ether and diisopropyl ether, cyclic ether solvents such as tetrahydrofuran and dioxane, ketone solvents such as acetone and methylethyl ketone, halogenated solvents such as chloroform and 1,2-dichloroethane. Alkyl solvents, aromatic solvents such as toluene, o-dichlorobenzene, nitrobenzene, and m-talesol, N-methylpyrrolidone, and carbon dioxide disulfide can be mentioned. Of these solvents, a solvent containing a non-halogen solvent is preferable, and a non-halogen solvent is preferable.

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, and 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, Ma Nesium 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, a known conductive polymer whose conductivity has been improved by doping or the like, for example, conductive polyarlin, conductive polypyrrole, conductive polythiophene, a complex of polyethylene dioxythiophene and polystyrene sulfonic acid is preferably used. It is done. Among them, those having a low electrical resistance on the contact surface with the semiconductor layer are preferable.

[0100] 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, aluminum, copper, or the like Resist by thermal transfer, ink jet, etc. on metal foil There is a method of etching using a metal. Alternatively, the conductive polymer solution or dispersion, or the conductive fine particle dispersion may be directly patterned by ink jetting, or may be formed from the 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, lithographic printing, or screen printing can also be used.

[0101] As the 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, magnesium barium fluoride, bismuth titanate, strontium bismuth titanate, strontium bismuth tantanoate, bismuth tantalate niobate, and yttrium trioxide. Among them, acid silicate, acid aluminum, acid tantalum, and acid titanium are preferred. Inorganic nitrides such as silicon nitride and aluminum nitride can also be suitably used.

[0102] Examples of the film formation method 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 coating methods, printing and ink jet patterning methods, etc. Can be used depending on the material.

[0103] 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.

[0104] The method of forming an insulating film by plasma film formation under atmospheric pressure is a process in which a thin film is formed on a substrate by discharging at atmospheric pressure or a pressure near atmospheric pressure to excite reactive gas in plasma. The method is disclosed in JP-A-11-61406, JP-A-11-133205, JP-A-2000-121804, JP-A-2000-147209, JP-A-2000-185362. (Hereinafter also referred to as atmospheric pressure plasma method). As a result, a highly functional thin film can be formed with high productivity.

[0105] Further, as the organic compound film, polyimides, polyamides, polyesters, polyacrylates, photo-radical polymerization-type, photo-powered thione polymerization-type photocurable resins, or copolymers containing acrylonitrile components, polybules. Phenolic alcohol, polybutyl alcohol, novolac resin, cyano ethyl pullulan and the like can also 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 stacked and used together. The thickness of these insulating films is generally 50ηπ! ˜3 m, preferably 100 nm to l μm.

[0106] The support is made of glass or a flexible resin sheet, and 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). Thus, by using a plastic film, it is possible to reduce the weight as compared with the case of using a glass substrate, to improve portability, and to improve resistance to impact.

Hereinafter, an organic thin film transistor (organic TFT) using an organic thin film formed using the organic semiconductor compound according to the present invention will be described.

FIG. 1 is a diagram showing a configuration example of an organic TFT according to 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, and an organic semiconductor layer 1 which is the organic thin film transistor material of the present invention is formed between both electrodes. An insulating layer 5 is formed thereon, and a gate electrode 4 is further formed thereon to form a field effect 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) shows that the organic semiconductor 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. [0109] In FIG. 4 (d), the gate electrode 4 is formed on the support 6 with a metal foil or the like, and then the insulating layer 5 is formed thereon. The organic semiconductor layer 1 formed by the organic thin film transistor material of the present invention is formed between the electrodes. Other configurations such as those shown in (e) and (f) of FIG.

[0111] The organic TFT sheet 10 has a large number of organic TFTs 11 arranged in a matrix. 7 is a gate bus line of each TF T11, and 8 is a source bus line of each TFT11. An output element 12 is connected to the source electrode of each TFT 11, and this output element 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 an input electrode of the photosensor. In the example shown in the figure, an equivalent circuit including a liquid crystal force resistor and a capacitor force is shown as an output element. 13 is a storage capacitor, 14 is a vertical drive circuit, and 15 is a horizontal drive circuit.

[0112] In addition, the organic TFT using the organic semiconductor material of the present invention can be applied to the technology introduced in, for example, SID2005, sessio n49-1, 2, 3, and an a-Si transistor of the present invention can be applied. Good characteristics can be obtained by replacing it with an organic semiconductor transistor.

[0113] Hereinafter, an organic electroluminescent element (organic EL element) including the organic TFT of the present invention will be described as an example of technology application.

[0114] 《Organic EL device (Organic electoluminescence device)》

The organic semiconductor device or the organic thin film transistor of the present invention can be provided in an organic electroluminescence element (also referred to as an organic EL element). The organic EL element is, for example, an organic EL layer (organic layer) between an anode and a cathode. Force, which includes a state in which the organic compound layer is sandwiched (also referred to as a sandwiched state). These configurations include a conventionally known layer configuration, a material of an organic EL layer, and the like. I can do it. For example, reference can be made to the literature of Nature, 395, 151-154.

[0115] In emitting light from an organic EL element (for example, applied to a display device, a lighting device, etc.), the organic semiconductor device of the present invention is obtained from the viewpoint of obtaining high light emission luminance and a long light emission lifetime. Alternatively, it is preferable to have the organic thin film transistor of the present invention. [0116] 《Display device》

The organic EL element may be used as a kind of lamp such as an illumination or exposure light source, a projection device that projects images, or a display device that directly recognizes still images and moving images (displays) ) May be used. When used as a display device for video playback, either the simple matrix (passive matrix) method or the active matrix method may be used. Alternatively, it is possible to produce a full-color display device by using two or more organic EL elements of the present invention having different emission colors.

[0117] An example of a display device comprising the organic EL element power of the present invention will be described with reference to the drawings.

FIG. 3 is a schematic diagram showing an example of a display device configured with organic EL element power.

[0119] Fig. 11 is a schematic diagram of a display such as a mobile phone that displays image information by light emission of an organic EL element. The display 21 also has a display unit A having a plurality of pixels, a control unit B that performs image scanning of the display unit A based on image information, and the like.

[0120] The control unit B is electrically connected to the display unit A, and sends a scanning signal and an image data signal to each of a plurality of pixels based on image information from the outside. Sequentially emit light according to the image data signal, scan the image, and display the image information on the display unit A.

FIG. 4 is a schematic diagram of the display unit A.

[0122] The display portion A includes a wiring portion including a plurality of scanning lines 25 and data lines 26, a plurality of pixels 23, and the like on a substrate.

[0123] The main members of the display unit A will be described below.

In the figure, the light power emitted from the pixel 23 is taken out in the direction of the white arrow (downward). The scanning lines 25 and the plurality of data lines 26 in the wiring portion are each made of a conductive material, and the scanning lines 25 and the data lines 26 are orthogonal to each other in a grid pattern and are connected to the pixels 23 at the orthogonal positions (details). Is not shown).

[0125] When a scanning signal is applied from the scanning line 25, the pixel 23 receives an image data signal from the data line 26. And emits light according to the received image data. Full color display is possible by appropriately arranging pixels in the red region, the green region, and the blue region on the same substrate.

Next, the light emission process of the pixel will be described.

FIG. 5 is a schematic diagram of a pixel.

The pixel includes an organic EL element 100, a switching transistor 110, a driving transistor 120, a capacitor 130, and the like. Full-color display can be performed by using red, green, and blue light emitting organic EL elements as the organic EL elements 100 for a plurality of pixels and arranging them on the same substrate.

In FIG. 5, an image data signal is applied from the control unit B to the drain of the switching transistor 110 via the data line 60. When a scanning signal is applied from the control unit B to the gate of the switching transistor 110 via the scanning line 50, the switching transistor 110 is turned on, and the image data signal applied to the drain is driven by the capacitor 130. It is transmitted to the gate of transistor 120.

By transmitting the image data signal, the capacitor 130 is charged according to the potential of the image data signal, and the drive of the drive transistor 120 is turned on. The drive transistor 120 has a drain connected to the power supply line 7, a source connected to the electrode of the organic EL element 100, and the power supply line 70 to the organic EL element 100 according to the potential of the image data signal applied to the gate. Current is supplied.

When the scanning signal is moved to the next scanning line 50 by the sequential scanning of the control unit B, the driving of the switching transistor 11 is turned off. However, even if the driving of the switching transistor 110 is turned off, the capacitor 130 maintains the potential of the charged image data signal, so that the driving of the driving transistor 12 is kept on and the next scanning signal is applied. The organic EL device 10 continues to emit light until it is released. When a scanning signal is next applied by sequential scanning, the driving transistor 120 is driven according to the potential of the next image data signal synchronized with the scanning signal, and the organic EL element 100 emits light.

That is, the organic EL element 100 emits light by providing a switching transistor 110 and a drive transistor 120 as active elements for the organic EL element 100 of each of a plurality of pixels. Accordingly, each of the organic EL elements 100 provided in the plurality of pixels 23 as shown in FIG. 4 emits light. Such a light emitting method is called an active matrix method.

Here, the light emission of the organic EL element 100 may be light emission of a plurality of gradations by a multi-value image data signal having a plurality of gradation potentials, or a predetermined light emission by a binary image data signal. The amount can be on or off.

[0134] Further, the potential of the capacitor 130 may be maintained until the next scanning signal is applied, or may be discharged immediately before the next scanning signal is applied.

In the present invention, not only the active matrix method described above, but also a passive matrix light emission drive in which an organic EL element emits light according to a data signal only when a scanning signal is scanned.

Example

[0136] Hereinafter, the present invention will be described by way of examples, but the present invention is not limited thereto. Here, the structural formulas of comparative organic semiconductor materials (both organic semiconductor compounds!) Used in the examples are shown below.

[0137] [Chemical formula 18] Comparative compound (1) Comparative compound (2)

Comparative compound (3) Comparative compound (4)

[0138] Example 1

<< Production of Organic Thin Film Transistor 1 >>

A 2000 A 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, and then surface treatment with octadecyltrichlorosilane was performed.

[0139] On a Si wafer subjected to such a surface treatment, Comparative Compound 1 (Pentacene, manufactured by Aldrich, used after sublimation purification of a commercially available reagent) was bubbled with nitrogen in a nitrogen atmosphere for 30 minutes. It is dissolved at a concentration of 0.5% by mass in toluene, spin-coated in a nitrogen atmosphere (rotation speed 2500 rpm, 15 seconds), and naturally dried to form a cast film, and then 50 ° in a nitrogen atmosphere. C, heat-treated for 30 minutes.

[0140] Further, gold was deposited on the surface of the film using a mask to form a source electrode and a drain electrode. An organic thin film transistor 1 having a source electrode and a drain electrode having a width of 100 m, a thickness of 200 nm, a channel width W = 3 mm, and a channel length L = 20 μm was produced.

[0141] << Production of Organic Thin Film Transistor 2 >>

Comparative compound 2 (2, 3, 9, 10-tetrahexylpentacene) was synthesized by the method described in Organic Letters, vol. 2 (2000), p85.

[0142] Organic thin film transistor 2 was produced in the same manner as in the production of organic thin film transistor 1, except that comparative compound 1 was changed to comparative compound 2.

[0143] << Production of Organic Thin Film Transistor 3 >>

Comparative Compound 3 was synthesized by the method described in J. Am. Chem. Soc., Vol. 127 (2005), ρ4986, supporting information.

[0144] Organic thin film transistor 3 was produced in the same manner as in the production of organic thin film transistor 1, except that comparative compound 1 was changed to comparative compound 3.

[0145] << Production of Organic Thin Film Transistor 4 >>

In the preparation of the organic thin film transistor 1, Comparative I匕合product 4 Comparative I匕合product 1 was changed to (rubrene, Aldrich, and was used sublimation purification commercially available reagent) in a similar manner, an organic thin film transistor ⁴ Produced.

[0146] << Production of Organic Thin Film Transistors 5-19 >> Organic thin film transistors 5 to 19 were produced in the same manner as in the production of the organic thin film transistor 2, except that the organic semiconductor material of the present invention described in Table 1 was used instead of the comparative compound 1.

[0147] <Evaluation of carrier mobility and ONZOFF value>

For the obtained organic thin film transistors 1 to 19, the carrier mobility and the ONZOFF value of each element were measured immediately after the element was created. In the present invention, the carrier mobility is obtained from the saturation region of the IV characteristics, and further, the ONZOFF ratio is obtained from the ratio of the drain current value when the drain bias is set to 50 V and the gate bias is set to 50 V and OV.

[0148] In addition, the same evaluation was performed, and each element was placed in an environmental room at 40 ° C and 90% RH for 48 hours, and then carrier mobility and ONZOFF ratio were measured again. The results obtained are shown in Table 1.

[0149] [Table 1]

From Table 1, organic thin film transistors ₅ to ₁₉ fabricated using the organic semiconductor material of the present invention showed excellent characteristics in both carrier mobility and ONZOFF ratio immediately after fabrication, and the mobility was 10 after the durability test. — ² or more, ON / OFF ratio is 10 ⁵ or more, and there is little deterioration over time.

Claims

Claims [1] In an organic semiconductor material containing a compound having, as a partial structure, an aromatic condensed polycycle in which three or more rings are condensed, the aromatic condensed polycycle is represented by the following general formula (1) An organic semiconductor material characterized by having three or more substituents.

[Chemical formula 1] General formula Π)

—≡ ~ *

[Wherein, R represents a hydrogen atom, a halogen atom or a substituent, and a plurality of R may be the same or different. * Represents a bonding site with the aromatic condensed polycycle. ]

[2] The organic semiconductor material according to claim 1, wherein the aromatic condensed polycycle includes at least one partial structure represented by the following general formula (2).

[Chemical formula 2] General formula (2)

[Wherein, R and R each represents a hydrogen atom, a halogen atom or a substituent. However, R

1 2

May be the same or different, and the Rs may be the same or different.

1 2

]

[3] The organic semiconductor material according to claim 2, wherein the aromatic condensed polycycle includes two or more partial structures represented by the general formula (2)! /

[4] A request comprising a compound having a partial structure represented by the following general formula (3): 4. The organic semiconductor material according to any one of items 1 to 3 of the required range.

[Chemical formula 3] General formula (3)

3 6

It represents the integer above, 2≤nl + n2 + n3≤5. ]

[5] R in the general formula (1), R and R in the general formula (2), R to R force in the general formula (3), each alkyl group

1 2 3 6

, A cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon ring group, an aromatic complex ring group, Si () or Ge () (R ′ represents a substituent). Special

3 3

The organic semiconductor material according to any one of claims 1 to 4, wherein:

[6] R in the general formula (1), R and R in the general formula (2), R to R 1S in the general formula (3)

1 2 3 6

Hydrogenated ring group, aromatic heterocyclic group, Si () or Ge () (R 'represents a substituent.

3 3

The The organic semiconductor material according to claim 5, wherein

[7] R and R in the general formula (2) and R to R forces in the general formula (3) are the same substituents.

1 2 3 6

The organic semiconductor material according to any one of claims 2 to 6, wherein the organic semiconductor material is characterized in that

[8] R in the general formula (1), R and R in the general formula (2), R to R 1S aromatic hydrocarbon in the general formula (3)

1 2 3 6

The organic semiconductor material according to claim 6 or 7, wherein the organic semiconductor material represents an alicyclic group.

[9] The organic semiconductor material according to claim 8, wherein the aromatic hydrocarbon ring group is a substituted phenyl group.

[10] The organic semiconductor material according to claim 9, wherein the substituted position of the substituted phenyl group is 2, 6 substitution or 2, 4, 6 substitution.

[11] The organic according to claim 10, wherein the substituent in the 2,6-substituted or 2,4,6-substituted is also an alkyl group, an alkoxy group or a phenyl group Semiconductor material.

[12] The organic semiconductor according to any one of [8] to [11], wherein in the general formula (3), nl = l, n2 = l, n3 = 1 material.

[13] R and R in the general formula (2), and R to R in the general formula (3) are each an aromatic in which two or more rings are condensed.

1 2 3 6

The organic semiconductor material according to any one of claims 2 to 7, which is a hydrocarbon ring group or an aromatic heterocyclic group.

[14] An organic semiconductor film comprising the organic semiconductor material according to any one of claims 1 to 13.

[15] The organic semiconductor material according to any one of claims 1 to 13 is dissolved or dispersed in an organic solvent, and the resulting solution or dispersion is applied and dried. An organic semiconductor film characterized by being made.

[16] An organic semiconductor device using the organic semiconductor material according to any one of claims 1 to 13.

[17] An organic thin film transistor, wherein the organic semiconductor material according to any one of claims 1 to 13 is used for a semiconductor layer.