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Polymer based on (E)-1, 2-di (2-thiophene) ethylene and benzothiadiazole as well as preparation method and application thereof

A technology for benzothiadiazole and polymers, which is applied in the field of polymers based on -1,2-diylethylene and benzothiadiazole and its preparation, can solve the problems of complex synthetic routes and raw materials, and achieve strong Promote and apply the value, enhance the conjugated structure, and improve the effect of stability

Pending Publication Date: 2020-05-05
杭州奥得科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The electrical properties and stability of existing organic polymer materials ne

Method used

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  • Polymer based on (E)-1, 2-di (2-thiophene) ethylene and benzothiadiazole as well as preparation method and application thereof
  • Polymer based on (E)-1, 2-di (2-thiophene) ethylene and benzothiadiazole as well as preparation method and application thereof
  • Polymer based on (E)-1, 2-di (2-thiophene) ethylene and benzothiadiazole as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0037] Example 1 Synthesis of polymer P1

[0038] A polymer based on (E)-1,2-bis(2-thiophene)ethylene and benzothiadiazole, specifically polymer P6 having the following general formula,

[0039]

[0040] The specific preparation process is as follows:

[0041] (1) Preparation C 12 H 25 -BTV-BO 2 C 6 H 12 : Under anhydrous and oxygen-free conditions, at a temperature of 0℃, add 3-bromothiophene (200mmol), dry THF (200ml) and LDA (240mmol) to the flask, react for 1h, then add dry DMF (240mmol) , React for 0.5h, after the reaction is over, cool to room temperature, overnight, after post-treatment, a brown liquid is obtained, which is the intermediate product 4-bromothiophene-2-carbaldehyde, and the yield is 45%.

[0042] Drop TiCl into the flask containing dry THF (20ml) 4 (20mmol), stir for 15min, then add Zn powder (35mmol), react at 65℃ for 1h, slowly add the intermediate product 4-bromothiophene-2-carboxaldehyde (12mmol) dropwise, and stir overnight. After post-treatment, a yellow po...

Example Embodiment

[0056] Example 2. Synthesis of polymer P2

[0057] A polymer based on (E)-1,2-bis(2-thiophene)ethylene and benzothiadiazole, specifically polymer P2 having the following general formula,

[0058]

[0059] The specific preparation process is as follows:

[0060] (1) Preparation C 8 H 17 -BTV-Sn(C 4 H 9 ) 3 : Under anhydrous and oxygen-free conditions, at a temperature of 0℃, add 3-bromothiophene (400mmol), dry THF (400ml), and LDA (480mmol) to the flask, react for 1h, then add dry DMF (480mmol) ), react for 0.5h, after the reaction is over, cool to room temperature, overnight, after post-treatment, a brown liquid is obtained, which is the intermediate product 4-bromothiophene-2-carbaldehyde, and the yield is 40%.

[0061] Drop TiCl into a flask containing dry THF (50ml) 4 (39.26mmol), stir for 15min, then add Zn powder (65.43mmol), react at 65℃ for 1h, slowly add the intermediate product 4-bromothiophene-2-carboxaldehyde (26.17mmol) dropwise, stir overnight, after post-treatment, a yel...

Example Embodiment

[0076] Example 3. Synthesis of polymer P3

[0077] A polymer based on (E)-1,2-bis(2-thiophene)ethylene and benzothiadiazole, specifically polymer P3 having the following general formula,

[0078]

[0079] The specific preparation process is as follows:

[0080] (1) Preparation C 10 H 21 -BTV-BO 2 C 6 H 12 : Under anhydrous and oxygen-free conditions, at a temperature of 0°C, add 3-bromothiophene (400mmol), dry THF (400ml) and LDA (480mmol) to the flask, react for 1h, then add dry DMF (480mmol) , React for 0.5h, after the reaction is over, cool to room temperature, overnight, after post-treatment, a brown liquid is obtained, which is the intermediate product 4-bromothiophene-2-carbaldehyde, and the yield is 40%.

[0081] Drop TiCl into the flask with dry THF (50ml) 4 (39.26mmol), stir for 15min, then add Zn powder (65.43mmol), react at 65℃ for 1h, slowly add the intermediate product 4-bromothiophene-2-carboxaldehyde (26.17mmol) dropwise, stir overnight, after post-treatment, a yellow c...

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Abstract

The invention relates to the technical field of organic synthesis, in particular to a polymer based on (E)-1, 2-bis (2-thiophene) ethylene and benzothiadiazole as well as a preparation method and application of the polyme. R in the polymer is alkyl, the number of carbon atoms is 6-14, X is tin salt or borate, and Y is H, F or Cl. The polymer has excellent sunlight capturing capability and hole transport capability as an active layer material. Because of the thermal stability, solution processability and light absorption of the polymer, the polymer has a good application prospect in the photoelectric fields of solar cell devices, organic electroluminescent devices, organic field effect transistors and the like.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a polymer based on (E)-1,2-bis(2-thiophene)ethylene and benzothiadiazole, a preparation method and application thereof. Background technique [0002] Conductive polymers have attracted the attention of scientists due to their low density, easy processing, and wide range of synthesis. Due to the conjugation of the structure of this kind of material, it can receive light to generate electricity and transport charges, so it can be applied in many electronic or optoelectronic devices, such as: solar cell devices, organic electroluminescent devices and organic field effect transistors. [0003] The structure of materials fundamentally determines the properties of materials. Therefore, the structural innovation and synthesis of materials has always been a hot spot in the field of organic electronics. The carrier mobility and solubility of polymers determine its development a...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/30H01L51/46H01L51/54
CPCC08G61/126C08G61/123C08G2261/124C08G2261/1412C08G2261/146C08G2261/18C08G2261/3223C08G2261/3246C08G2261/414C08G2261/91C08G2261/92C08G2261/95H10K85/113H10K85/151Y02E10/549Y02P70/50
Inventor 刘江涛高立群乔冠伟高建华马望京
Owner 杭州奥得科技有限公司
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