Pyrrolopyrrole monoketotetrabenzene analogue polymer, preparation method and applications thereof

A technology of pyrrolopyrrole monoketone and pyrrolopyrrole monoketone, which is applied in the field of pyrrolopyrrole monoketopetracene analog polymers and their preparation, can solve the problems of complex reaction steps and low yield, and achieve good dissolution The performance, the synthesis method is simple, and the effect that is conducive to the transmission of electrons

Active Publication Date: 2020-02-28
SUN YAT SEN UNIV
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Problems solved by technology

At present, the modification of diketopyrrolopyrrole is mainly the modification of the alkyl group by the amide or the modification of different conjugated groups at the position of the double bond. There is no report on the modification of the alkyl chain on one side of the amide bond and the ring-closing modification on the other side, and the existing The technology has disadvantages such as low yield and complicated reaction steps.

Method used

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  • Pyrrolopyrrole monoketotetrabenzene analogue polymer, preparation method and applications thereof
  • Pyrrolopyrrole monoketotetrabenzene analogue polymer, preparation method and applications thereof
  • Pyrrolopyrrole monoketotetrabenzene analogue polymer, preparation method and applications thereof

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Embodiment 1

[0059] A method for preparing an aza-tetracene analog polymer of pyrrole monoketone, comprising the steps of:

[0060] (1) 3.00g 3,6-di(2-thienyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione (I) and 2.9g tert-butanol Potassium was added to a three-neck round bottom flask, degassed and then filled with nitrogen for three consecutive times, then added 50mL N,N-dimethylformamide (DMF), stirred, and then added 1-bromo-2-decyltetradecane C 24 h 49 Br 4.17g, reacted at room temperature for 4h. The obtained solution was rotary evaporated first, then purified by chromatography column, and compound II could be obtained by distillation under reduced pressure. The quality of the obtained compound was 1.57 g, and the yield was 32%; image 3 for compound II 1 H NMR spectrum, Figure 4 for compound II 13 C NMR, proton nuclear magnetic resonance spectrum can prove that the synthesized compound is structure II.

[0061] (2) Add 1.46g of compound (II), 1.52g of potassium carbonate and 0....

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Abstract

The invention discloses a pyrrolopyrrole monoketotetrabenzene analogue polymer, which is a conjugated polymer taking a pyrrolopyrrole monoketotetrabenzene analogue as a module. According to the invention, a novel pyrrolopyrrole monoketotetrabenzene analogue is synthesized through a simple method, and polymers with three types of structures are synthesized by a simple stile coupling polymerizationmethod; compared with other acene structures, the synthesized acene analogue polymer has high yield, has a larger conjugated structure compared with pyrrolopyrrole, and is beneficial to hole transport; and the pyrrolopyrrole monoketotetrabenzene analogue polymer has potential application prospects in the fields of organic field effect transistors (OFET) and organic solar cells (OPV).

Description

technical field [0001] The present invention relates to the technical field of organic semiconductor synthesis, and more specifically, to a pyrrolopyrrole monoketonaphthacene analogue polymer and its preparation method and application. Background technique [0002] Diketopyrrolopyrrole derivatives are a very important class of organic semiconductor materials due to their large planar structure, low LUMO energy level, and high air stability. At present, the modification of diketopyrrolopyrrole is mainly the modification of the alkyl group by the amide or the modification of different conjugated groups at the position of the double bond. There is no report on the modification of the alkyl chain on one side of the amide bond and the ring-closing modification on the other side, and the existing The technology has disadvantages such as low yield and complex reaction steps. Therefore, it is of great significance to use the existing diketopyrrolopyrrole as a raw material to modify...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/30H01L51/46
CPCC08G61/126C08G61/123C08G61/124C08G2261/124C08G2261/143C08G2261/146C08G2261/1412C08G2261/414C08G2261/514C08G2261/59C08G2261/18C08G2261/3223C08G2261/3241C08G2261/3243C08G2261/1424H10K85/113H10K85/151Y02E10/549
Inventor 岳晚王亚洲杨欣茹
Owner SUN YAT SEN UNIV
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