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.

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

CN1803792AInactive Publication Date: 2006-07-19CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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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

Examples

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

Patent Timeline
19 Jul 2006
Publication
CN1803792A
IPC
C07D333/04; C07D495/04; C07D519/00; C07D513/04; H01L51/30
Inventors
耿延候; 田洪坤