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Asymmetric organic small molecular photovoltaic material based on benzothiadiazole unit, preparation method and application thereof

A technology of benzothiadiazole and photovoltaic materials, applied in photovoltaic power generation, organic chemistry, electrical components, etc., can solve the problems of low photovoltaic devices, little research on asymmetric organic small molecule photovoltaic materials, lack of systematic research, etc., to achieve Effect of improving planarity and reducing HOMO energy level

Active Publication Date: 2018-01-26
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This shows that there are still few studies involving benzothiadiazole-based asymmetric organic small molecule photovoltaic materials
At the same time, there is a lack of systematic research on the adjustment of the energy levels of such structures by π-conjugated linkages with different electron-withdrawing properties. The PCE and V of the corresponding photovoltaic devices oc also generally lower

Method used

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  • Asymmetric organic small molecular photovoltaic material based on benzothiadiazole unit, preparation method and application thereof
  • Asymmetric organic small molecular photovoltaic material based on benzothiadiazole unit, preparation method and application thereof
  • Asymmetric organic small molecular photovoltaic material based on benzothiadiazole unit, preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0052] This example discloses the synthesis process of organic small molecule donor material Q1, the synthesis steps are as follows:

[0053] Under nitrogen protection, compound A (0.25mmol, 0.178g), compound D1 (0.30mmol, 0.134g), tetrakis (triphenylphosphine) palladium (0.025mmol, 29mg) and potassium carbonate (10mmol, 1.380 g) were placed Into a 50 mL three-necked flask, 10 mL of toluene, 5 mL of ethanol and 5 mL of water were sequentially added, and heated at reflux at 110° C. for 48 h. The reaction solution was cooled to room temperature, poured into 20 mL of water and extracted with dichloromethane (3×30 mL), the organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. Chloromethane was used as a developing solvent for column chromatography to obtain 0.143 g of a red solid with a yield of 60.0%.

[0054] The reaction formula of above-mentioned preparation compound Q1 is as follows:

[0055]

[0056] see ...

Embodiment 2

[0060] This embodiment discloses the synthesis process of organic small molecule donor material Q2, and the synthesis steps are as follows:

[0061] Under the protection of nitrogen, compound A (0.25mmol, 0.178g), compound D2 (0.30mmol, 0.142g), tetrakis (triphenylphosphine) palladium (0.025mmol, 29mg) and potassium carbonate (10mmol, 1.380 g) were placed Into a 50 mL three-necked flask, 10 mL of toluene, 5 mL of ethanol and 5 mL of water were sequentially added, and heated at reflux at 110° C. for 48 h. The reaction solution was cooled to room temperature, poured into 20 mL of water and extracted with dichloromethane (3×30 mL), the organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. Chloromethane was used as a developing solvent for column chromatography to obtain 0.159 g of a red solid with a yield of 65.0%.

[0062] The reaction formula of above-mentioned preparation compound Q2 is as follows:

[0063] ...

Embodiment 3

[0068] This example discloses the synthesis process of the organic small molecule donor material Q3, the synthesis steps are as follows:

[0069] Under nitrogen protection, compound A (0.25mmol, 0.178g), compound D3 (0.30mmol, 0.150g), tetrakis (triphenylphosphine) palladium (0.025mmol, 29mg) and potassium carbonate (10mmol, 1.380 g) were placed Into a 50 mL three-necked flask, 10 mL of toluene, 5 mL of ethanol and 5 mL of water were sequentially added, and heated at reflux at 110° C. for 48 h. The reaction solution was cooled to room temperature, poured into 20 mL of water and extracted with dichloromethane (3×30 mL), the organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. Chloromethane was used as a developing solvent for column chromatography to obtain 0.153 g of a red solid with a yield of 61.0%.

[0070] The reaction formula of above-mentioned preparation compound Q3 is as follows:

[0071]

[0072] s...

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Abstract

Belonging to the field of photoelectric materials, the invention discloses a benzothiadiazole asymmetric organic small molecular photovoltaic material, a preparation method and application thereof. The D-Pi-A-A' type asymmetric molecule involved in the invention adopts benzothiadiazole as unit A, takes triphenylamine as unit D, employs phenyl, styryl, 2-cyano-styryl and phenylacetylene as Pi connecting bond respectively, and uses biscyanovinyl as the A' end group. In addition, different bridged bonds and the A' end group synergistically strengthen the ICT effect and reduce the HOMO energy level of the molecule. The 2-cyano-styryl connecting bond broadens the molecular absorption range. The introduction of phenyl or 2-cyano-styryl can reduce the HOMO energy level of the molecule, and Voc can exceed 1.0V. The PCE of the synthetic material is up to 2.43%. The compound has a clear structure, good solubility and film-forming properties, and has the potential of serving as an efficient asymmetric organic small molecular donor photovoltaic material.

Description

technical field [0001] The invention relates to a benzothiadiazole asymmetric organic small molecule photovoltaic material, a preparation method thereof and a solar cell device using the benzothiadiazole organic small molecule as a donor material, belonging to the field of organic photoelectric materials. Background technique [0002] Compared with polymers, organic small molecules have the advantages of easy structure modification, simple purification and preparation, and low cost of photovoltaic device fabrication, and have become the main research content of organic photovoltaics. So far, the photoelectric conversion efficiency (PCE) of solution-processed symmetric organic small molecule donor materials has reached 11.3%, which is very close to the PCE of current polymer donor materials, which shows that the research on organic small molecule donor materials has theoretical and practical significance. practical application value. Compared with polymer donor materials, th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/14H01L51/42H01L51/46
CPCY02E10/549
Inventor 谢宝殷伦祥李艳芹
Owner DALIAN UNIV OF TECH
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