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Benzotriazole small-organic-molecule photovoltaic material and preparation method and application thereof

A technology of benzotriazoles and photovoltaic materials, applied in photovoltaic power generation, organic chemistry, semiconductor/solid-state device manufacturing, etc., can solve the problem of low PCE of solar cell devices and lack of research on benzotriazole-based small organic molecules and other problems, to achieve the effect of improving charge transport, increasing the initial oxidation potential, and enhancing the ability to donate electrons

Inactive Publication Date: 2016-02-24
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, compared with polymer materials, the research on benzotriazole organic small molecule compounds is relatively scarce, and the PCE of corresponding solar cell devices is generally low.

Method used

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  • Benzotriazole small-organic-molecule photovoltaic material and preparation method and application thereof
  • Benzotriazole small-organic-molecule photovoltaic material and preparation method and application thereof
  • Benzotriazole small-organic-molecule photovoltaic material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] This example discloses the specific synthesis process of the organic small molecule donor material F1, including the following steps:

[0042] Under nitrogen protection, compound A (147mg, 0.2mmol), N,N-diphenyl-4-(4,4,5,5-tetramethyl-[2,1,3]Coxolane Boryl)aniline, ie D when Q represents a single bond (186mg, 0.5mmol), sodium carbonate (848mg, 8.0mmol) and tetrakis(triphenylphosphine)palladium (22mg, 0.02mmol) were dissolved in toluene (8mL) , a mixed solution of deionized water (4 mL) and ethanol (2 mL), and reflux at 110° C. for 24 hours. After the reaction solution was cooled to room temperature, it was poured into 20 mL of deionized water and separated, and extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate. The organic solvent was removed by rotary evaporation, and the crude product was purified by column chromatography using petroleum ether / dichloromethane (v:v, 5:1) as a developing solvent to obtain the target product as a...

Embodiment 2

[0049] This example discloses the specific synthesis process of the organic small molecule donor material F2, including the following steps:

[0050] Compound A (147mg, 0.2mmol), 4-(N,N-diphenylamino)styrene, that is, D (136mg, 0.5mmol) when Q represents C=C, sodium acetate (410mg, 5mmol), palladium acetate (4mg, 0.02mmol) and TBAB (26mg, 0.08mmol) were dissolved in 12mL of N,N-dimethylformamide solution and refluxed at 100°C for 36 hours. After the reaction solution was cooled to room temperature, it was poured into 50 mL of deionized water, extracted with dichloromethane, and the obtained organic phase was washed with a large amount of deionized water, and the organic phase was dried with anhydrous sodium sulfate. The organic solvent was removed by rotary evaporation, and the crude product was purified by column chromatography using petroleum ether / dichloromethane (v:v, 3:1) as a developing solvent to obtain the target product as an orange-red solid with a yield of 42%.

[...

Embodiment 3

[0057] This example discloses the specific synthesis process of the organic small molecule donor material F3, including the following steps:

[0058] Compound A (147mg, 0.2mmol), 4-(N,N-diphenylamino)phenylacetylene, that is, D (134mg, 0.5mmol) when Q represents C≡C, di(triphenylphosphine) dichloride Palladium (4mg, 0.005mmol) and cuprous iodide (2mg, 0.01mmol) were dissolved in a mixed solution of 20mL tetrahydrofuran and 15mL triethylamine, and refluxed at 70°C for 24 hours. The reaction solution cooled to room temperature was poured into 50 mL of deionized water, extracted with dichloromethane, and the combined organic phases were dried over anhydrous sodium sulfate. The organic solvent was removed by rotary evaporation, and the crude product was purified by column chromatography using petroleum ether / dichloromethane (v:v, 5:1) as a developing solvent to obtain the target product as an orange solid with a yield of 45%.

[0059] The reaction formula of above-mentioned prepa...

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Abstract

The invention discloses a benzotriazole small-organic-molecule photovoltaic material and a preparation method and application thereof and belongs to the field of photoelectric materials. The compound uses benzotriazole as a nucleus, uses triphenylamine as an end group and uses thiophene, a single bond, C = C or C=C as connecting keys respectively. After fluorine atoms having higher electronegativity are introduced to the benzotriazole, the initial oxidation potential of the material is improved. The triphenylamine is used as the end group, so that the electron donating capability of molecules is enhanced, the hole-transporting performance is improved, and the solubility of the compound is improved in coordination with an alkyl group on the benzotriazole. The C = C is introduced in the molecules, so that the absorption range of the compound is widened. The single bond or the C = C is introduced so that the HOMO energy level can be effectively reduced. The VOC of a device is improved through coordination of the single bond or the C = C introduced in the molecules and the monofluoro benzotriazole. The PCE of the synthetic material is above 1.70%, the highest PCE is up to 4.77%, and the benzotriazole small-organic-molecule photovoltaic material has the potential of serving as an efficient small-organic-molecule photovoltaic donor material.

Description

technical field [0001] The invention relates to a benzotriazole organic small molecule photovoltaic material, a preparation method thereof and a solar cell device using the benzotriazole organic small molecule as a donor material, belonging to the field of organic photoelectric materials. Background technique [0002] In recent years, solution-processed organic small molecule solar cell materials have gradually become a research hotspot due to their advantages such as easy modification of molecular structure, easy separation and purification, and low cost of device fabrication. At present, the photoelectric conversion efficiency (PCE) of solution-process organic small molecule solar cells reported in the literature has reached as high as 10.10%, which makes the research on small molecule photovoltaic materials have important theoretical and practical application value. However, compared with polymer solar cell devices, the overall efficiency of solar cell devices based on sm...

Claims

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Application Information

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IPC IPC(8): C07D409/14H01L51/46
CPCC07D409/14H10K85/6572H10K30/00Y02E10/549
Inventor 汲长艳殷伦祥李艳芹
Owner DALIAN UNIV OF TECH
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