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Pyrrolodione-thiophene quinone compound, and preparation method and application thereof

A technology of diketopyrrole and quinone compounds, which is applied in the field of organic semiconductor materials, and achieves the effects of simple synthesis method, low cost and improved order

Active Publication Date: 2013-04-17
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the study of optimizing molecular properties by changing the structure of the oligothiophene core has not been reported

Method used

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  • Pyrrolodione-thiophene quinone compound, and preparation method and application thereof
  • Pyrrolodione-thiophene quinone compound, and preparation method and application thereof
  • Pyrrolodione-thiophene quinone compound, and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1: compound (a) shown in synthetic formula I and preparation n-type organic field effect transistor

[0038]

[0039] 1) compound (a) shown in synthetic formula I:

[0040] Under nitrogen protection conditions, sodium hydride (0.111g, 4.63mmol) was suspended in ethylene glycol dimethyl ether (10mL), the temperature was lowered to 0°C, and malononitrile (0.092g, 1.39mmol) was slowly added In the system, after the addition, stir at this temperature for 10 minutes, remove the ice bath, warm up to room temperature, and stir for 30 minutes. Add successively to the system the α-bromosubstituted diketopyrrole-thiophene oligomer precursor (0.393g, 0.58mmol) and tetrakis(triphenylphosphine) palladium (0 ) (0.067g, 0.058mmol), heated to reflux (temperature is 100°C). With the increase of reflux time, a dark purple precipitate was precipitated in the system after 1 hour, indicating the formation of a dianion intermediate. After 4.5 hours, cool down to room tempera...

Embodiment 2

[0050] Embodiment 2: compound (b) shown in synthetic formula I and preparation n-type organic field effect transistor

[0051]

[0052] 1) Compound (b) shown in synthetic formula I:

[0053] Under nitrogen protection conditions, sodium hydride (0.111g, 4.63mmol) was suspended in ethylene glycol dimethyl ether (10mL), the temperature was lowered to 0°C, and malononitrile (0.092g, 1.39mmol) was slowly added In the system, after the addition, stir at this temperature for 10 minutes, remove the ice bath, warm up to room temperature, and stir for 30 minutes. Add successively to the system the α-bromo-substituted pyrrole diketop-thiophene oligomer precursor (0.522g, 0.58mmol) and tetrakis(triphenylphosphine) palladium (0 ) (0.067g, 0.058mmol), heated to reflux (temperature is 100°C). With the increase of reflux time, a dark purple precipitate was precipitated in the system after 1 hour, indicating the formation of a dianion intermediate. After 4.5 hours, cool down to room temp...

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Abstract

The invention discloses a pyrrolodione-thiophene quinone compound, and a preparation method and an application thereof. The pyrrolodione-thiophene quinone compound is as shown in a formula I. The preparation method comprises the following steps: mixing and performing a nucleophilic substitution reaction for sodium hydride, alpha-bromine-substituted pyrrolodione-thiophene oligomer as shown in a formula II and malononitrile sodium salt under a catalysis effect of tetra(triphenylphosphine) palladium (0) (Pd(PPh3)4) to generate di-anion intermediates, and adding saturated bromine water into the reaction system for an oxidation reaction, thereby obtaining the compound as shown in the formula I after the reaction completes. The compound is excellent in field-effect performance, and has an electron mobility of over 0.1cm<2>V<-1>s<-1>, wherein in an embodiment 1, for a material (a), an electron mobility of a field effect device of a semiconductor layer prepared by a vacuum vaporization method can reach to 0.3 cm<2>V<-1>s<-1>, and in an embodiment 2, for a material (b), an electron mobility of a field effect device with a semiconductor layer prepared by a spin coating method can reach to 0.35 cm<2>V<-1>s<-1>. A current on / off ratio of the compound is up to 10 <5>. The compound has stable performances in the air and has important application values.

Description

technical field [0001] The invention relates to an organic semiconductor material of a field effect transistor, in particular to a diketopyrrole-thiophenequinone compound and a preparation method and application thereof. Background technique [0002] Since the organic field effect transistor (OFET) first appeared in 1986 (Tsumura, A.; Koezuka, H.; Ando, ​​T. Appl. Phys. Lett. 1986, 49, 1210), due to its application in large-area sensors, electronic radio frequency The potential application value of labels, electronic paper, and large-screen displays has attracted widespread attention. Compared with inorganic transistors, organic field effect transistors have the characteristics of low cost, light weight, and good flexibility. In recent years, organic field effect transistors have made great progress and become one of the most important organic electronic devices. (Zaumseil, J., Sirringhaus, H., Chem. Rev. 2007, 107, 1296-1323; Murphy, A.R., Frechet, J.M.J., Chem. Rev. 2007...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04H01L51/30H10K99/00
CPCC07D487/04C09B23/005C09B23/0058C09B57/004H10K85/611H10K85/621H10K85/655H10K10/484H10K85/6572H10K85/657H10K10/462
Inventor 乔雅丽张敬徐伟朱道本
Owner INST OF CHEM CHINESE ACAD OF SCI
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