Thienopyridine derivative, method for producing same and organic semiconductor device using same

A technology of organic semiconductors and derivatives, applied in the fields of semiconductor devices, semiconductor/solid-state device manufacturing, electric solid-state devices, etc., can solve the problem that the characteristics may not be sufficient

Inactive Publication Date: 2013-01-16
HIROSHIMA UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the characteristics required for organic semiconductor devices such as carrier mobility are not necessarily sufficient, and it is desired to provide new organic semiconductor materials for the purpose of further improvement.

Method used

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  • Thienopyridine derivative, method for producing same and organic semiconductor device using same
  • Thienopyridine derivative, method for producing same and organic semiconductor device using same
  • Thienopyridine derivative, method for producing same and organic semiconductor device using same

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0106] (Synthesis Example 1) [Synthesis of 5-phenylsulfonylthieno[2,3-c]pyridine represented by formula (6a)]

[0107] In a three-necked flask with an inner volume of 300ml equipped with a thermometer, a magnetic stirrer and a dropping funnel, benzenesulfonylcarbonitrile (3.77g, 22.6mmol) and isobutyl chloroformate (3.08g, 22.6mmol) were xylene (100ml) and stirred under reflux. To this mixture was added dropwise a solution of 3-methylthiophene-2-carbaldehyde-N-phenylimine (3.03 g, 15 mmol) in xylene (50 ml) over 30 minutes. After completion of the dropwise addition, the reaction mixture was heated under reflux for 1 hour, and after standing to cool to room temperature, the solvent was distilled off to obtain a crude product. These were purified by silica gel column chromatography to obtain 2.79 g of 5-benzenesulfonylthieno[2,3-c]pyridine (10.1 mmol, yield 67%). The chemical reaction formula is shown below.

[0108]

[0109] The NMR data of 5-benzenesulfonylthieno[2,3-c]p...

Synthetic example 2

[0111] (Synthesis Example 2) [Synthesis of 2-bromo-5-benzenesulfonylthieno[2,3-c]pyridine represented by formula (3a)]

[0112] Add 5-benzenesulfonylthieno[2,3-c]pyridine (2.37g, 8.6mmol), N-bromosuccinimide ( 4.60 g, 25.8 mmol) and 30 ml of acetonitrile, heated and stirred at 70° C. for 6 hours. After the reaction liquid was left to cool to room temperature, the solvent was distilled off, and 100 ml of ethyl acetate and 100 ml of water were added to the obtained residue. The organic layer was separated from the water layer with a separatory funnel, and the water layer was extracted twice with 50 ml of ethyl acetate. It was mixed with the previously separated organic layer, and after washing twice with 100 ml of water, the organic layer was dried over anhydrous magnesium sulfate. The crude product obtained by distilling off the solvent with toluene and ethyl acetate was purified by recrystallization to obtain 2.49 g of 2-bromo-5-benzenesulfonylthieno[2,3-c]pyridine (7.0 mmol...

Synthetic example 3-1

[0116] (Synthesis Example 3-1) [Synthesis of 2-bromo-5-methoxythieno[2,3-c]pyridine represented by formula (3b)]

[0117] Add 2-bromo-5-benzenesulfonylthieno[2,3-c]pyridine (1.00g, 2.8mmol), 28 % methanol solution (1.62g, 8.4mmol) and 20ml of tetrahydrofuran, heated and stirred at 60°C for 6 hours. The reaction solution was left to cool to room temperature, and after adding 1 ml of acetic acid, the solvent was distilled off, and 50 ml of ethyl acetate and 50 ml of water were added to the obtained residue. The organic phase was separated from the aqueous phase with a separatory funnel, and the organic phase was dried over anhydrous magnesium sulfate. The crude product obtained by distilling off the solvent was purified by silica gel column chromatography to obtain 0.635 g of 2-bromo-5-methoxythieno[2,3-c]pyridine (2.6 mmol, yield: 93%). The chemical reaction formula is shown below.

[0118]

[0119] The NMR data of 2-bromo-5-methoxythieno[2,3-c]pyridine represented by the...

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Abstract

Disclosed is a novel thienopyridine derivative shown by general formula (1) that is useful as an organic semiconductor device and specifically as an organic thin film transistor. Also disclosed is a method for producing the same. [In the formula, R<1> is a hydrogen atom, optionally substituted alkyl group, optionally substituted alkenyl group, optionally substituted alkynyl group, optionally substituted alkoxy group, optionally substituted aryl group, optionally substituted heteroaromatic ring group, optionally substituted alkylthio group, optionally substituted arylthio group, optionally substituted ester group or a substituent shown by -SO2R<2> (wherein R<2> is an optionally substituted C1-20 hydrocarbon group), and W is at least one substituent selected from a group comprising optionally substituted aryl groups and optionally substituted heteroaromatic ring groups.]

Description

technical field [0001] The present invention relates to a novel compound having a thienopyridine skeleton, a preparation method thereof, and an organic semiconductor device using the compound. Background technique [0002] In recent years, nanoscale π-conjugated molecules have attracted attention as various functional materials such as conductive materials, photoelectric conversion materials, electroluminescent materials, nonlinear optical materials, and field-effect transistor materials, especially as organic semiconductor materials. Generally, in the case of an organic semiconductor material composed of a low-molecular compound, an organic semiconductor layer can be formed by vapor deposition at a relatively low temperature. In addition, regardless of a low-molecular compound or a high-molecular compound, the organic semiconductor layer can be formed by, for example, a solution method such as a printing method such as an inkjet method. Therefore, by producing an organic s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04H01L29/786H01L51/05H01L51/30
CPCC07B37/04H01L51/0071H01L51/0545C07D495/04H10K85/657H10K10/466H10K10/484
Inventor 大下净治播磨裕杉冈尚金平浩一
Owner HIROSHIMA UNIVERSITY
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