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A kind of benzotriazole organic small molecule photovoltaic material and its preparation method and application

A technology of benzotriazoles and photovoltaic materials, which is applied in photovoltaic power generation, organic chemistry, semiconductor/solid-state device manufacturing, etc. and other problems, to achieve the effect of increasing the initial oxidation potential, improving charge transport, and reducing the forbidden band width.

Inactive Publication Date: 2018-01-30
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • A kind of benzotriazole organic small molecule photovoltaic material and its preparation method and application
  • A kind of benzotriazole organic small molecule photovoltaic material and its preparation method and application
  • A kind of benzotriazole organic small molecule photovoltaic material and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

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

[0042] Under nitrogen protection, compound A (147 mg, 0.2 mmol), N,N-diphenyl-4-(4,4,5,5-tetramethyl-[2,1,3]C oxolane Boronyl)aniline, i.e. D when Q represents a single bond (186mg, 0.5mmol), sodium carbonate (848mg, 8.0mmol) and tetrakis(triphenylphosphorus)palladium (22mg, 0.02mmol) were dissolved in toluene (8mL) , a mixed solution of deionized water (4 mL) and ethanol (2 mL), and refluxed at 110° C. for 24 hours. After the reaction solution was cooled to room temperature, it was poured into 20 mL of deionized water, 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 pr...

Embodiment 2

[0049] This embodiment 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, i.e. D (136mg, 0.5mmol) when Q represents C=C, sodium acetate (410mg, 5mmol), palladium acetate (4 mg, 0.02 mmol) and TBAB (26 mg, 0.08 mmol) were dissolved in 12 mL of a solution of N,N-dimethylformamide 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 ...

Embodiment 3

[0057] This embodiment 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, i.e. D (134mg, 0.5mmol) when Q represents C≡C, bis(triphenylphosphorus) dichloride Palladium (4 mg, 0.005 mmol) and cuprous iodide (2 mg, 0.01 mmol) were dissolved in a mixed solution of 20 mL of tetrahydrofuran and 15 mL of 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-...

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Abstract

The invention discloses a benzotriazole organic small molecular photovoltaic material, a preparation method and application thereof, and belongs to the field of photoelectric materials. The compound of the present invention uses benzotriazole as the core, triphenylamine as the terminal group, and respectively uses thiophene, a single bond, C=C or C≡C as the connecting bond. The introduction of highly electronegative fluorine atoms into benzotriazole increased the initial oxidation potential of the material. Using triphenylamine as the terminal group not only enhances the electron-donating ability of the molecule and improves the hole transport performance, but also synergizes with the alkyl group on the benzotriazole to increase the solubility of the compound. The introduction of C=C into the molecule broadens the absorption range of the compound; the introduction of a single bond or C≡C can effectively reduce the HOMO energy level. The single bond or C≡C introduced in the molecule synergistically increases the VOC of the device with monofluorobenzotriazole. The PCE of the synthetic material of the invention is all higher than 1.70%, up to 4.77%, and has the potential of being a high-efficiency organic small 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 optoelectronic materials. Background technique [0002] In recent years, solution process organic small molecule solar cell materials have gradually become a research hotspot due to their advantages of easy modification of molecular structure, easy separation and purification, and low cost of device fabrication. At present, the photoelectric conversion efficiency (PCE) in the field 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 bas...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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