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Phenanthrene/thiophene hybridized high-mobility organic semiconductor and application thereof

An organic semiconductor, high-mobility technology, applied in semiconductor devices, semiconductor/solid-state device manufacturing, organic chemistry, etc.

Inactive Publication Date: 2006-07-19
CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to overcome the shortcomings of the above-mentioned materials, the inventor has provided a series of oligomers with phenanthrene as the structural unit, and successfully applied them to organic thin film transistor devices (Chinese patent application number: 200510016895.9), but it still needs Further improve the field-induced mobility of the material, thereby improving the performance indicators of OTFTs devices

Method used

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  • Phenanthrene/thiophene hybridized high-mobility organic semiconductor and application thereof
  • Phenanthrene/thiophene hybridized high-mobility organic semiconductor and application thereof
  • Phenanthrene/thiophene hybridized high-mobility organic semiconductor and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1: the synthesis of 2-(2-phenanthrenyl)thiophene

[0044] Under the protection of argon, the 250ml round bottom flask connected to the double-row tube was baked three times with a gas lamp, and 7.69g (25.3mmol) of 2-iodophenanthrene, 8.58g (23.0mmol) of 2-(tributyltin base ) Thiophene, 500mg-1g of Pd (PPh 3 ) 4 , 80-150ml of DMF, the reaction mixture was stirred at 70-90°C for 5-10 hours, cooled to room temperature, poured into 500ml of water, extracted three times with 100ml of dichloromethane, combined organic phases, and separated with 100ml of saturated saline Wash three times, dry over anhydrous magnesium sulfate, remove the solvent by rotary evaporation, and separate and purify the obtained crude product by column chromatography, using petroleum ether as eluent to obtain 2-(2-phenanthrenyl)thiophene with a yield of 85%.

Embodiment 2

[0045] Embodiment 2: the synthesis of 2-bromo-5-(2-phenanthrenyl)thiophene

[0046] Under the protection of argon and avoiding light, add 4.79g (18.4mmol) of 2-(2-phenanthrenyl)thiophene to a 250ml three-necked flask, add 100-200ml of DMF that has been dried with calcium hydride, and place in an ice bath Within 0.5-1 hour, add 3.44g (19.3mmol) bromosuccinimide to the three-necked flask in portions, stir and react at this temperature for 1-2 hours, remove the ice bath, and continue stirring at room temperature for 2-2 hours. After 4 hours, add 500ml of water to end the reaction, continuously use 200ml of ether, wash three times with 100ml of saturated sodium thiosulfate solution respectively, dry the organic phase with anhydrous magnesium sulfate, and remove the solvent by rotary evaporation. The mixed solution of ether and dichloromethane was recrystallized to obtain 2-bromo-5-(2-phenanthrenyl)thiophene with a yield of 80%.

Embodiment 3

[0047] Example 3: Synthesis of 5,5'-bis(2-phenanthrenyl)-2,2'-dithiophene

[0048] Under the protection of argon, the 250ml round-bottomed flask connected to the double-row tube was baked three times with a gas lamp, and 4.79g (15.7mmol) of 2-iodophenanthrene, 5.32g (7.15mmol) of 5,5'-bis (Tributyltin base)-2,2'-dithiophene, 110-420mg of Pd(PPh 3 ) 4 , 60-200ml DMF, the reaction mixture was stirred at 70-100°C for 12-48 hours, cooled to room temperature, filtered to collect the precipitate, washed continuously with water, ethanol, dichloromethane, acetone, vacuum-dried, and the crude product was subjected to two Purified by sublimation in vacuum to obtain 5,5'-bis(2-phenanthrenyl)-2,2'-dithiophene with a yield of 50%.

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Abstract

The related phenanthrene / thiophene hybridized organic semiconductor with high mobility and general structural formula as the right has high thermal and environmental stability, can be purified by vacuum sublimation, dissolves very little in organic solvent, and can be used as transport layer in organic TFT.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronic materials, and relates to a phenanthrene / thiophene hybrid high-mobility organic semiconductor and its application in organic thin film transistors. technical background [0002] In recent years, organic thin-film transistors (OTFTs) using organic semiconductor materials as transport layers have attracted extensive attention. This device has potential applications in flat panel display driving circuits and low-cost memory components (such as identification cards, commodity price tags, etc.). Compared with traditional amorphous silicon (α-Si:H) devices, it has the advantages of low cost, large area coverage, and integration with flexible substrates. The Philips company of the Netherlands has completed the research and development of the world's first active-matrix liquid crystal display based on OTFTs (Nature, 2001, 414, 599.), and the organic semiconductor layer is polythiophene vin...

Claims

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Application Information

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IPC IPC(8): C07D333/04C07D495/04C07D519/00C07D513/04H01L51/30
Inventor 耿延候田洪坤史建武
Owner CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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