JP5391386B2 - Bisphenazacillin compound, method for producing bisphenazacillin compound, organic thin film transistor using bisphenazacillin compound - Google Patents

Description

  The present invention relates to a 5,10-dihydro-5H-phenazacillin (hereinafter simply referred to as “phenazacillin”) compound. The present invention relates to an organic thin film transistor using a bisphenazacillin compound.

  Conventionally, phenazacillin compounds are known as compounds that prevent oxidation (see, for example, Non-Patent Document 1). It is also known as a heat resistant additive for lubricants in jet engines (see Non-Patent Document 2, for example). Furthermore, it is also known that a low molecular weight compound of phenazacillin is suitably used as a hole transport material for a light emitting device (see, for example, Patent Documents 1 and 2). In addition, aromatic amine type polymers such as polyaniline are known to exhibit high electric activity.

On the other hand, it is known that a polymer of phenazacillin is suitably used as a hole transport material of a light emitting device (see, for example, Patent Documents 3, 4, and 5). Furthermore, it is also known as an additive that gives a resin a fluorescent function (for example, see Patent Document 6).
Issled. Obl. Fiz. Khim. Kauch. Rezin, 2, 14 (1973) Ann. N. Y. Acad. Sci. , 125, 242 (1965) JP-A-8-302339 Japanese Patent Laid-Open No. 10-218884 JP 2000-313739 A JP 2001-316457 A JP 2002-69161 A JP 2004-250536 A

  However, when the phenazacillin polymer described above is used as a constituent material of an electronic device such as a light emitting device, sufficient solubility in a general organic solvent may not be obtained. was there. In addition, since the polymer compound has a molecular weight distribution, it is difficult to provide a homogeneous material. Furthermore, when the phenazacillin monomer such as the conventional phenazacillin is used, sufficient characteristics may not be obtained as compared with the case of the polymer.

  The present invention has been made to solve the above-mentioned problems, and maintains the characteristics of a polymer of phenazacillin, and has a low molecular weight distribution. Bisphenazacillin compound, method for producing bisphenazacillin compound, bisphenazacillin It aims at providing the organic thin-film transistor using a compound.

（式中、Ｒ_１〜Ｒ_８はそれぞれ独立に置換されていてもよいアルキル基、置換されていてもよいアリール基、置換されていてもよいアルコキシ基、置換されていてもよいアリーロキシ基または水素原子を示す。） In order to achieve the above object, the bisphenazacillin compound of the invention according to claim 1 is a bisphenazacillin compound represented by the following general formula (1).

(Wherein R _{1 to} R ₈ are each independently an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkoxy group, an optionally substituted aryloxy group or hydrogen; Indicates an atom.)

（式中、Ｒ_１〜Ｒ_８はそれぞれ独立に置換されていてもよいアルキル基、置換されていてもよいアリール基、置換されていてもよいアルコキシ基、置換されていてもよいアリーロキシ基または水素原子を示し、Ａｒは二価のアリール基を示す。） The bisphenazacillin compound of the invention according to claim 2 is a bisphenazacillin compound represented by the following general formula (2).

(Wherein R _{1 to} R ₈ are each independently an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkoxy group, an optionally substituted aryloxy group or hydrogen; Represents an atom, and Ar represents a divalent aryl group.)

  Moreover, the manufacturing method of the bisphenazacillin compound of the invention which concerns on Claim 3 makes the said General formula (1) by coupling-reacting a 5,10- dihydro-5H-phenazacillin compound using a nickel complex. The bisphenazacillin compound according to claim 1 is produced.

  The method for producing a bisphenazacillin compound of the invention according to claim 4 is characterized in that the halogenated monophenazacillin compound is reacted with a distanyl compound or a diboryl compound in the presence of a palladium-based catalyst. The bisphenazacillin compound according to claim 2 represented by the formula (2) is produced.

  Moreover, the organic thin-film transistor of the invention which concerns on Claim 5 uses the bisphenazacillin compound of Claim 1 or 2, It is characterized by the above-mentioned.

  As a result of intensive studies to solve the above problems, the present inventors have found that the bisphenazacillin compound represented by the general formula (1) satisfies the above conditions. That is, the compound of the first invention is bis (5,10-dihydro-5H-phenazacillin) represented by the above general formula (1).

  The compound of the second invention is a compound in which two 5,10-dihydro-5H-phenazacillin compounds are bonded to an aromatic compound as represented by the general formula (2).

（式中、Ｒ_１〜Ｒ_４はそれぞれ独立に、置換されていてもよいアルキル基、アリール基、アルコキシ基、アリーロキシ基または水素原子を示し、Ｘはハロゲン原子を示す。） Moreover, the compound of 1st invention can be manufactured by performing the dehalogenation coupling reaction for the monophenazacillin compound represented by following General formula (3) using a nickel complex.

(In the formula, R _{1 to} R ₄ each independently represents an optionally substituted alkyl group, aryl group, alkoxy group, aryloxy group or hydrogen atom, and X represents a halogen atom.)

  The compound of the second invention can be produced by reacting the monophenazacillin compound represented by the general formula (3) with a distanyl compound or diboryl compound in the presence of a palladium-based catalyst. .

  The bisphenazacillin compound of the present invention is easily crystallized in halogenated hydrocarbons such as dichloromethane, dichloroethane, and chloroform, organic acids such as trifluoroacetic acid, and ordinary organic solvents such as toluene and THF (tetrahydrofuran). It can be easily formed into a thin film by using a normal coating method such as a spin coating method, a dip coating method, a roll coating method as well as a vacuum deposition method. It can be used as a constituent material.

  Hereinafter, an embodiment of the present invention will be specifically described using a plurality of examples, but the present invention is not limited to these examples.

First, in the general formulas (1) to (3), examples of the alkyl group represented by R _{1 to} R ₈ include methyl, ethyl, n- or iso-propyl, n-, iso- or tert-butyl, n Examples thereof include linear, branched and cyclic alkyl groups having 1 to 20, preferably 1 to 10, carbon atoms such as-, iso- or neo-pentyl, n-hexyl, cyclohexyl, n-heptyl and n-octyl. Alkoxy groups include methoxy, ethoxy, n- or iso-propoxy, n-, iso- or tert-butoxy, n-, iso- or neo-pentoxy, n-hexoxy, cyclohexoxy, n-heptoxy, n-octoxy Linear, branched and cyclic alkoxy groups having 1 to 20, preferably 1 to 10 carbon atoms. Examples of the aryl group include aryl groups having 6 to 20 carbon atoms, preferably 6 to 14 carbon atoms such as a phenyl group, o-, m-, p-tolyl group, 1- and 2-naphthyl group, and anthryl group. Examples of the aryloxy group include aryloxy groups having 6 to 20 carbon atoms, preferably 6 to 14 carbon atoms such as a phenoxy group, o-, m-, p-triloxy group, 1- and 2-naphthoxy group, and anthoxy group.

Furthermore, as the substituent of “optionally substituted” in R _{1 to} R _8, any substituent that does not participate in the coupling reaction described below may be used. For example, the above-described alkyl group, aryl group, alkoxy group, aryloxy Groups.

  In the general formula (2), examples of the divalent aryl group represented by Ar include o-, p-phenylene, thiophene-2,5-diyl, thiophene-2,3-diyl, pyridine-2, 5-diyl, pyridine-2,3-diyl, pyridine-4,5-diyl, naphthalene-1,4-diyl, naphthalene-2,6-diyl, naphthalene-1,2-diyl, naphthalene-1,7- Diyl, anthracene-9,10-diyl, anthracene-1,4-diyl, anthracene-2,6-diyl, anthracene-1,7-diyl, biphenylene-4,4′-diyl, fluorene-2,7-diyl And compounds in which the aromatic ring of these aromatic compounds is substituted are also included.

  Examples of the compound in which Ar is substituted on the aromatic ring of the aryl group include alkoxybenzene-1,4-diyl, alkylbenzene-1,4-diyl, arylbenzene-1,4-diyl, aryloxybenzene-1,4. -Diyl, 2,5-, 2,3-, 2,6-dialkoxybenzene-1,4-diyl, 2,3,5-trialkoxybenzene-1,4-diyl, 2,3,5,6 Tetraalkoxybenzene-1,4-diyl, 2,5-, 2,3-, 2,6-dialkylbenzene-1,4-diyl, 2,3,5-trialkylbenzene-1,4-diyl, 2 , 3,5,6-tetraalkylbenzene-1,4-diyl, 2,5-, 2,3-, 2,6-diarylbenzene-1,4-diyl, 2,3,5-triarylbenzene-1 , 4-Diyl, 2, , 5,6-tetraarylbenzene-1,4-diyl, 2,5-, 2,3-, 2,6-diallyloxybenzene-1,4-diyl, 2,3,5-triallyloxybenzene -1,4-diyl, 2,3,5,6-tetraaryloxybenzene-1,4-diyl, alkoxythiophene-2,5-diyl, alkylthiophene-2,5-diyl, arylthiophene-2,5 -Diyl, aryloxythiophene-2,5-diyl, dialkoxythiophene-2,5-diyl, dialkylthiophene-2,5-diyl, diarylthiophene-2,5-diyl, diaryloxythiophene-2,5- Diyl, 9,9-dialkoxyfluorene-2,7-diyl, 9,9-diarylfluorene-2,7-diyl, 9,9-diallyloxyfluore 2,7-diyl, and the like.

Furthermore, as a substituent which R < ₁ > -R < ₈ > of the said General formula (1) and (2) has what is not concerned in the coupling reaction mentioned later, for example, an above-described alkoxy group, an alkyl group, aryl Group and aryloxy group.

  The compound represented by the general formula (1) is obtained by dissolving the monohalogenated monophenazacillin compound of the general formula (3) in a solvent and using 1 to 20 equivalents of a nickel complex with respect to this monomer. It can be produced by carrying out a ring reaction. The reaction in this case is represented by the formula (a).

（式中、Ｒ_１〜Ｒ_８はそれぞれ独立に、置換されていてもよいアルキル基、アリール基、アルコキシ基、アリーロキシ基または水素原子を示し、Ｘはハロゲン原子を示す。）

(Wherein R _{1 to} R ₈ each independently represents an optionally substituted alkyl group, aryl group, alkoxy group, aryloxy group or hydrogen atom, and X represents a halogen atom.)

Examples of the nickel complex include tetracarbonylnickel (0), dicarbonylbis (triphenylphosphine) nickel (0), bis (1,5-cyclooctadiene) nickel (0), tetrakis (triphenylphosphine) nickel (0 ), (Η ₂ -ethylene) bis (triphenylphosphine) nickel (0), tetrakis (t-butyl isocyanate) nickel (0), [(1,2,5,6,8,10-η) -trans , Trans, trans-1,5,9-cyclododecatriene] nickel (0), and the like. The nickel complex is used in a proportion of 0.1 to 20 equivalents, preferably 1 to 5 equivalents, per equivalent of the compound (3).

  Further, 0.1 to 10 equivalents of a ligand such as 2,2′-bipyridyl or triphenylphosphine may be added to the nickel complex as a supporting ligand. For example, bis (1,5-cyclooctadiene) nickel (0) is added with 1 equivalent of 2,2′-bipyridyl, and bis (1,5-cyclooctadiene) nickel (0) is triphenyl. For example, 2 equivalents of phosphine are added.

  The compound represented by the general formula (2) can be produced by reacting a monohalogenated monophenazacillin compound with a distanyl compound or a diboryl compound in the presence of a palladium-based catalyst. This reaction is represented by the following reaction formula (b).

反応式（ｂ）において、Ｒ_１〜Ｒ_８及びＡｒは、いずれも前記一般式（１）および（２）で説明したと同意義である。また、Ｘは、ハロゲン原子を示し、Ｙ_１、Ｙ_２は、それぞれ独立に、ボリル基又はスタニル基を示す。

In the reaction formula (b), R _{1 to} R ₈ and Ar are all the same as explained in the general formulas (1) and (2). X represents a halogen atom, and Y ₁ and Y ₂ each independently represent a boryl group or a stannyl group.

  In these production methods, first, a halogenated monophenazacillin compound and a distanyl compound or diboryl compound are dissolved in a suitable organic solvent. Then, by adding 0.001 to 20 equivalents of a palladium-based catalyst to 1 equivalent of the monomer in the solution, the coupling reaction proceeds to facilitate the bisphenazacillin compound represented by the general formula (2). Can get to.

In Y ₁ -Ar—Y ₂ in the reaction formula (b), the stannyl groups represented by Y ₁ and Y ₂ are trimethylstannyl group, triethylstannyl group, tributylstannyl group, dimethylbutylstannyl. Groups. Examples of the boryl group represented by Y ₁ and Y ₂ include a dihydroxyboryl group, a dimethoxyboryl group, a diethoxyboryl group, a methoxyethoxyboryl group, and a 2,1,3-dioxaboryl group.

Here, a palladium-based catalyst is used for the coupling reaction. As the palladium-based catalyst, conventionally known palladium compounds and palladium complexes containing metallic palladium are used. Specifically, tetrakis (triphenylphosphine) palladium, palladium acetate, tetrakis (trimethylphosphine) palladium, tris (triethylphosphine) palladium, bis (tricyclohexylphosphine) palladium, tetrakis (triethylphosphito) palladium, tetrakis (triphenyl) Arsine) palladium, carbonyltris (triphenylphosphine) palladium, (η ² -ethylene) bis (triphenylphosphine) palladium, (η ² -maleic anhydride) [1,2-bis (diphenylphosphino) ethane] palladium, Bis (cycloocta-1,5-diene) palladium, tris (dibenzylideneacetone) dipalladium, bis (dibenzylideneacetone) palladium, chloro (methyl) (1,5-si Looctadiene) palladium, diethylbis (triphenylphosphito) palladium, diethylbis (trimethylphosphito) palladium, diethylbis (tri-i-propylphosphito) palladium, dimethyl [1,2-bis (dimethylphosphino) ethane] palladium, dimethyl [1,3-bis (dimethylphosphino) propane] palladium, dimethyl [1,2-bis (dimethylamino) ethane] palladium, dimethylbis (4-ethyl-1-phospha-2,6,7-trioxabicyclo [2.2.2] octane) palladium, bis (t-butylisocyanide) dimethylpalladium, bis (1,1,3,3-tetramethylbutylisocyanide) dimethylpalladium, diphenylbis (methyldiphenylphosphinite) palladium, Dibenzylbis (trimethylphosphine) palladium, diethynylbis (triethylphosphine) palladium, dineopentyl (2,2'-bipyridyl) palladium, bromo (methyl) bis (triethylphosphine) palladium, benzoyl (chloro) bis (trimethylphosphine) palladium, cyclopentadi Enyl (phenyl) (triethylphosphine) palladium, η-allyl (pentamethylcyclopentadienyl) palladium, π-allyl (1,5-cyclooctadiene) palladium tetrafluoroborate, bis (π-allyl) palladium, bis Examples thereof include supported palladium metals such as (acetylacetonato) palladium, dichloroethylenediamine palladium, palladium chloride, and palladium carbon. These palladium-based catalysts are used in a proportion of 0.001 to 20 equivalents, preferably 0.01 to 0.1 equivalents, per equivalent of the raw material monophenazacillin compound.

  Moreover, in Formula (b), you may make it react by adding additives, such as 0.1-10 equivalent lithium chloride and copper bromide, with respect to a palladium catalyst. Further, in the coupling reaction, the reaction can be carried out by adding a base. As the base, various bases usually used in the coupling reaction can be used. For example, potassium carbonate, potassium hydroxide, sodium carbonate, sodium hydroxide, sodium bicarbonate, sodium ethoxide, sodium acetate, lithium carbonate, lithium hydroxide, lithium oxide, potassium acetate, magnesium oxide, calcium oxide, Barium hydroxide, trilithium phosphate, trisodium phosphate, tripotassium phosphate, cesium fluoride, aluminum oxide, trimethylamine, triethylamine, N, N, N ′, N′-tetramethylethylenediamine, diisopropylamine, diisopropylethylamine, Examples thereof include N-methylpiperidine, 2,2,6,6-tetramethyl-N-methylpiperidine, pyridine, 4-dimethylaminopyridine, and N-methylmorpholine. The amount of the base used is 1 to 100 equivalents, preferably 1 to 20 equivalents, with respect to 1 equivalent of the monophenazacillin compound shown in the reaction formula (b). These bases may be used as an aqueous solution.

  In the halogenated phenazacillin compounds shown in the reaction formulas (a) and (b), examples of the halogen atom represented by X include a chlorine atom, a bromine atom, and an iodine atom. Ease of synthesis and stability of the compound In particular, a bromine atom is preferable.

  For the coupling reaction in the reaction formulas (a) and (b), various solvents usually used in this type of reaction can be used. Examples thereof include N, N-dimethylformamide (DMF), toluene, benzene, tetrahydrofuran (THF) and the like.

  In addition, the coupling reaction in the reaction formula (a) and the reaction formula (b) can be performed at various temperatures from the melting point of the solvent to the boiling point of the solvent, and about 0 ° C. to 100 ° C. is particularly desirable. After completion of the reaction, the product can be easily purified by a reprecipitation method, a chromatogram or the like.

  The bisphenazacillin compound of the present invention obtained by the above method can be used as various optical functional materials and electronic materials such as semiconductors by forming a film such as vapor deposition. In addition, these compounds have mechanical properties such as high strength and excellent heat resistance, and also have various electrical and optical properties, so that they can be used for electronic materials such as organic thin film transistor elements. Moreover, it can also be used as a hole transport layer of an organic thin film light emitting device or an organic photoreceptor.

まず、四塩化炭素１００ｍＬとクロロホルム１００ｍＬの混合溶媒に、５．０ｇ（２７．３ｍｍｏｌ）の４−メチルジフェニルアミンを溶かしたフラスコを氷浴にいれ、さらにＮ−ブロモこはく酸イミドを１５．１ｇ（８４．６ｍｍｏｌ）加えて２日撹拌した。水を加えて抽出したのち、メタノールで洗浄することにより１０．５ｇ（２４．４ｍｍｏｌ）４−メチル−２’，４’，４−トリブロモジフェニルアミンを粉末として得た。 Example 1
Bis (5,8,10,10 tetramethylphenazacillin-2-yl) represented by the following formula (general formula 1, R ₁ = R ₂ = R ₃ = R ₄ = R ₅ = R ₆ = R ₇ = R ₈ = methyl group)

First, a flask in which 5.0 g (27.3 mmol) of 4-methyldiphenylamine was dissolved in a mixed solvent of 100 mL of carbon tetrachloride and 100 mL of chloroform was placed in an ice bath, and 15.1 g (84% of N-bromosuccinimide was added). 6 mmol) and stirred for 2 days. After adding water and extracting, 10.5 g (24.4 mmol) of 4-methyl-2 ′, 4 ′, 4-tribromodiphenylamine was obtained as a powder by washing with methanol.

  Next, 40 mL of THF was added to a Schlenk tube under a nitrogen atmosphere containing 3.93 g of sodium hydride, and then 3.03 g of 4-methyl-2 ′, 4 ′, 4-tribromodiphenylamine was added to add 50 mL. Stir for 1 hour at ° C. Further, 3.23 g of methyl iodide was added and stirred at 50 ° C. for 24 hours. The reaction was stopped and extracted by adding water, and then the product was washed with methanol to obtain 2.37 g of 4, N-dimethyl-2 ', 4', 4-tribromodiphenylamine as a powder.

  Furthermore, after suspending 4.51 g of 4, N-dimethyl-2 ′, 4 ′, 4-tribromodiphenylamine in 30 mL of ether in an ice bath, 14.3 mL of n-butyllithium in hexane solution (1 .6M) was added. Further, 1.48 g of dimethyldichlorosilane was added, and after the precipitate was formed, the ice bath was removed and the mixture was stirred for 12 hours. The reaction solution was poured into ice water, extracted with ether, and then recrystallized with methanol to obtain 1.80 g of 2-bromo-5,8,10,10-tetramethyl-5,10-dihydrophenazacillin as colorless crystals. As isolated.

  Subsequently, 1 mL of 1,5-cyclooctadiene was added to 490 mg (1.8 mmol) of bis (cyclooctadiene) nickel (0) under a nitrogen atmosphere, and then 10 mL of toluene was added and suspended. Further, 280 mg (1.8 mmol) of 2,2'-bipyridyl was added and stirred. Further, 840 mg (2.5 mmol) of 2-bromo-5,8,10,10 tetramethylphenazacillin was added, and the mixture was heated to 60 ° C. and stirred for 48 hours. 2M hydrochloric acid was added to the reaction solution, and the mixture was further extracted with chloroform. Then, the organic layer was reprecipitated with methanol to obtain 410 mg (0.8 mmol) of bis (5,8,10,10 tetramethylphenazacillin-2-yl). ) Was isolated.

The NMR data of the compound is as follows.
¹ H-NMR spectrum (CDCl ₃ ): δ 6.9 to 7.7 (m, 12H), 3.55 (s, 6H), 2.34 (s, 6H), 0.45 (s, 12H) ppm
¹³ C-NMR spectrum (CDCl ₃ ): δ 149.88, 148.69, 133.58, 132.71, 131.30, 130.66, 129.23, 128.32, 123.34, 122.98, 115.06, 114.86, 38.10, 20.44, -1.99 ppm

  The absorption maximum wavelength of the chloroform solution of this compound was 336 nm, and the fluorescence maximum wavelength was 385 nm.

Example 2
2,5-bis (5,8,10,10-tetramethylphenazacillin-2-yl) thiophene represented by the following formula (general formula 2, R ₁ = R ₂ = R ₃ = R ₄ = R ₅ = R ₆ = _R 7 = _{R 8} = methyl, Ar = thiophen-2,5-diyl) synthesis of

The NMR data of the compound is as follows.
¹ H-NMR spectrum (CDCl ₃ ): δ 6.9 to 7.7 (m, 14H), 3.54 (s, 6H), 2.34 (s, 6H), 0.47 (s, 12H) ppm
¹³ C-NMR spectrum (CDCl ₃ ): δ 150.24, 148.49, 142.71, 133.62, 130.75, 130.35, 129.52, 127.27, 126.40, 123.42, 122.90, 122.59, 115.08, 114.98, 38.19, 20.45, -1.97 ppm

  The absorption maximum wavelength of the chloroform solution of this compound was 379 nm, and the fluorescence maximum wavelength was 442 nm.

窒素雰囲気下で２−ブロモ−５，８，１０，１０−テトラメチル−５，１０−ジヒドロフェナザシリン２９６ｍｇと９，９−ジオクチルフルオレン−２，７−ジボロン酸（反応式ａ参照、Ａｒ＝９，９−ジオクチルフルオレン−２，７−ジイル，Ｙ_１＝Ｙ_２＝ジヒドロキシボリル基）２００ｍｇをトルエン１０ｍＬに加えて懸濁させた。次に、炭酸カルシウム１．０７ｇを５ｍＬの水に溶かしたものを加えてかくはんした。更にテトラキストリフェニルホスフインパラジウム（０）２５ｍｇを加えた後、９０℃に昇温して４８時間かくはんした。生成した反応液をエーテルで抽出し、メタノールに析出させることにより、２，７−ビス（５，８，１０，１０−テトラメチルフェナザシリン−２−イル）−９，９−ジオクチルフルオレンを２２５ｍｇ（０．２５ｍｍｏｌ）を単離した。 Example 3
2,7-bis (5,8,10,10-tetramethylphenazacillin-2-yl) -9,9-dioctylfluorene represented by the following formula (general formula 2, R ₁ = R ₂ = R ₃ = R ₄ = the synthesis of _{R 5 = R 6 = R 7} = R 8 = methyl, Ar = 9,9-dialkyl-2,7-diyl)

Under a nitrogen atmosphere, 296 mg of 2-bromo-5,8,10,10-tetramethyl-5,10-dihydrophenazacillin and 9,9-dioctylfluorene-2,7-diboronic acid (see reaction formula a, Ar = 200 mg of 9,9-dioctylfluorene-2,7-diyl, Y ₁ = Y ₂ = dihydroxyboryl group) was added to 10 mL of toluene and suspended. Next, 1.07 g of calcium carbonate dissolved in 5 mL of water was added and stirred. Further, 25 mg of tetrakistriphenylphosphine palladium (0) was added, and the mixture was heated to 90 ° C. and stirred for 48 hours. The resulting reaction solution was extracted with ether and precipitated in methanol, whereby 225 mg of 2,7-bis (5,8,10,10-tetramethylphenazacillin-2-yl) -9,9-dioctylfluorene was obtained. (0.25 mmol) was isolated.

The NMR data of the compound is as follows.
¹ H-NMR spectrum (CDCl ₃ ): δ 6.9 to 7.8 (m, 18H), 3.58 (s, 6H), 2.35 (s, 6H), 2.02 (t, 4H), 0.8-1.4 (m, 30H) 0.49 (s, 12H) ppm

Example 4
Production of Organic Thin Film Transistor (Part 1) Using Bisphenazacillin Compound FIG. 1 is a schematic cross-sectional view of an organic thin film transistor 10. A glass plate having a thickness of 0.7 mm was used as the substrate 6, and this glass plate was subjected to ultrasonic cleaning using ultrapure water and an organic solvent, and then aluminum was vacuum-deposited as the gate electrode 5 by 50 nm. Next, after ozone cleaning, a polyimide precursor film was formed on the gate electrode 5 by spin coating, and baked at 200 ° C. to form a gate insulating layer 4 having a thickness of 270 nm. On the polyimide, the bisphenazacillin compound 3 described in Example 1 was deposited to a thickness of 50 nm by vacuum deposition. Further thereon, gold was formed into a film by 50 nm vacuum vapor deposition, and an organic thin film transistor 10 was produced as the source electrode 1 and the drain electrode 2.

Gate length 175μm using the compound described in Example 1, the mobility of the elements of the gate width 506μm is ^{1.73 × 10- 4 [cm 2 /} Vs], on-off ratio of ¹⁰ 4. ⁰³ , p-type transistor characteristics with a threshold voltage of −25.9 V were exhibited.

Example 5
Preparation of Organic Thin Film Transistor (Part 2) Using Bisphenazacillin Compound Using a compound described in Example 2 under the same conditions as in Example 4, a device having a gate length of 181 mm and a gate width of 511 mm has a mobility ^{1.98 × 10- 5 [cm 2 /} Vs], on-off ratio of ¹⁰ 3. ³⁶ , p-type transistor characteristics with a threshold voltage of −12.3 V were shown.

  As described above, since the bisphenazacillin compound has high solubility in an organic solvent, film formation is possible not only by a method such as vapor deposition but also by using a normal coating method such as a spin coating method or a dip coating method. Is possible. The obtained thin film can be used as various optical functional materials and electronic materials such as semiconductors. In addition, these compounds have mechanical properties such as high strength and excellent heat resistance, as well as various electrical and optical properties, so that they are used in organic thin-film light-emitting devices and organic photoreceptor hole transport layers. Can be used as It can also be used as a constituent material of electronic materials such as organic thin film transistor elements.

1 is a schematic cross-sectional view of an organic thin film transistor 10. FIG.

Explanation of symbols

DESCRIPTION OF SYMBOLS 1 Source electrode 2 Drain electrode 3 Bisphenazacillin compound 4 Gate insulating layer 5 Gate electrode 6 Substrate 10 Organic thin-film transistor

Claims (5)

Bisphenazacillin compounds represented by the following general formula (1).

_(Wherein, R 1 to R ₈ is an alkyl group.) R ₁ ~ R ₈ The bisphenazacillin compound according to claim 1, wherein is a methyl group. Bisphenazacillin compounds represented by the following general formula (2).

(Wherein R _{1 to} R ₈ represent an alkyl group, and Ar represents a thiophene-2,5-diyl group or a 9,9-dialkylfluorene-2,7-diyl group ) R ₁ ~ R ₈ The bisphenazacillin compound according to claim 3, wherein is a methyl group. The organic thin-film transistor using the bisphenazacillin compound in any one of Claims 1 thru | or 4 .

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