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Star-shaped triphenylamine derivative, and preparation method and applications thereof

A technology of triphenylamine and its derivatives, which is applied in the field of organic optoelectronic materials, can solve the problems that molecules are not easy to pile up in an orderly manner, and the photoelectric conversion efficiency is not as good as that of molecules with symmetrical structures, and the difference is far away, so as to facilitate transmission and separation, and improve photoelectric conversion. Efficiency, the effect of increasing absorbance

Inactive Publication Date: 2017-06-20
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Experimental results show that when molecules with asymmetric structures are used as donor materials, although the absorbance increases, the photoelectric conversion efficiency is far lower than that of molecules with symmetrical structures.
The reason is that asymmetric molecular donor materials are not easy to carry out orderly accumulation of molecules during film formation, which limits the transport of carriers and greatly reduces the photoelectric conversion efficiency of the device.
And for triphenylamine derivatives with symmetrical structure such as T-A 1 3 (Wei Li, Qingdao Li, Chunhui Duan, Shengjian Liu, Lei Ying, Fei Huang, YongCao. Design and synthesis of star-burst triphenylamine-basedπ-conjugated molecules. Dyes and Pigments 2015, 113:1-7) and other electron donor materials , with the fullerene derivative PC 71 The photoelectric conversion efficiency of the bulk heterojunction organic photovoltaic device prepared with BM acceptor materials is only 0.6%, and it can reach 1.39% after further optimization, which is the same as the highest efficiency of the current organic small molecule photovoltaic cells (>12% ) is far from

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  • Star-shaped triphenylamine derivative, and preparation method and applications thereof
  • Star-shaped triphenylamine derivative, and preparation method and applications thereof
  • Star-shaped triphenylamine derivative, and preparation method and applications thereof

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Experimental program
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Effect test

Embodiment 1

[0027] Step 1: Add 13.93mmol of 3,4-ethylenedioxythiophene and 80ml of tetrahydrofuran into the reaction vessel under a nitrogen atmosphere, cool down to -78°C, then slowly add 15.32mmol of n-butyllithium dropwise, and react for 20 minutes Return to room temperature naturally, continue stirring for 1 h, then lower the temperature to -78°C, then slowly add 15.32 mmol of tributyltin chloride dropwise, return to room temperature naturally, and stir overnight. After the reaction was completed, it was quenched with 30 ml of ice water, extracted with dichloromethane, washed twice with saturated sodium chloride solution and distilled water, dried by adding anhydrous sodium sulfate, and concentrated by suspension evaporation. The obtained crude product was purified by silica gel column chromatography, gradient elution, and the solvent was removed to obtain an intermediate product 1: 2-(tributyltin)-3,4-ethylenedioxythiophene.

[0028] MS: m / z=432.15

[0029] 1 H NMR (300 MHz, DMSO) ...

Embodiment 2

[0044] Step 1: Add 27.86mmol of 3,4-ethylenedioxythiophene and 90ml of tetrahydrofuran into the reaction vessel under a nitrogen atmosphere, cool down to -78°C, then slowly add 30.65mmol of n-butyllithium dropwise, and react for 40 minutes Return to room temperature naturally, continue stirring for 2 h, then lower the temperature to -78°C, then slowly add 30.65 mmol of tributyltin chloride dropwise, return to room temperature naturally, and stir overnight. After the reaction was completed, it was quenched with 35 ml of ice water, extracted with dichloromethane, washed twice with saturated sodium chloride solution and distilled water, dried by adding anhydrous sodium sulfate, and concentrated by suspension evaporation. The obtained crude product was purified by silica gel column chromatography, gradient elution, and the solvent was removed to obtain an intermediate product 1: 2-(tributyltin)-3,4-ethylenedioxythiophene.

[0045] MS: m / z=432.08

[0046] 1 H NMR (300 MHz, DMSO) ...

Embodiment 3

[0061] Step 1: Add 41.79mmol of 3,4-ethylenedioxythiophene and 100ml of tetrahydrofuran into the reaction vessel under a nitrogen atmosphere, cool down to -78°C, and then slowly add 45.969mmol of n-butyllithium dropwise. After 1 hour of reaction, the Return to room temperature, continue stirring for 3 h, then lower the temperature to -78°C, then slowly add 45.97 mmol of tributyltin chloride dropwise, return to room temperature naturally, and stir overnight. After the reaction was completed, it was quenched with 40 ml of ice water, extracted with dichloromethane, washed three times with saturated sodium chloride solution and distilled water, dried with anhydrous sodium sulfate, and concentrated by suspension evaporation. The obtained crude product was purified by silica gel column chromatography, gradient elution, and the solvent was removed to obtain an intermediate product 1: 2-(tributyltin)-3,4-ethylenedioxythiophene.

[0062] MS: m / z=432.11

[0063] 1 H NMR (300 MHz, DMSO...

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Abstract

The invention discloses a star-shaped triphenylamine derivative, and a preparation method and applications thereof. According to the preparation method, 3,4-ethoxylene dioxy thiophene is reacted with n-butyllithium and tributyl tin chloride successively so as to obtain an intermediate 1; under the catalytic action of palladium, the intermediate 1 is reacted with tris(4-bromophenyl)amine so as to obtain an intermediate 2; under the action of phosphorus oxychloride, the intermediate 2 is reacted with N,N-dimethylformamide so as to obtain an intermediate 3; and at last, the intermediate 3 is reacted with malononitrile in the presence of triethylamine so as to obtain a finished product N,N,N-tri[4-(5-dicyanovinyl-3,4-ethenyldioxy-2-thienyl) phenyl]amine. The star-shaped triphenylamine derivative is possible to be used as a high efficiency organic photovoltaic cell electron donor material because of the unique molecular structure and large conjugated system.

Description

technical field [0001] The invention relates to a triphenylamine derivative, in particular to a star-shaped triphenylamine derivative applied to an organic photovoltaic cell donor material and a preparation method and application thereof, belonging to the technical field of organic photoelectric materials. Background technique [0002] Due to the advantages of low density, low price and easy structure modification of organic molecules, organic optoelectronic materials have been widely used in the fields of organic light-emitting diodes, organic transistors, organic photovoltaic cells and organic memories in recent years. Among them, after years of unremitting efforts by scientific researchers, the photoelectric conversion efficiency of organic photovoltaic cells has been rapidly improved, but it is still not comparable to that of inorganic photovoltaic cells. Therefore, how to prepare high-efficiency organic photoelectric materials, optimize the structure of battery devices,...

Claims

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Application Information

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IPC IPC(8): C07D495/04H01L51/42H01L51/46
CPCC07D495/04H10K85/631H10K85/657H10K30/20Y02E10/549Y02P70/50
Inventor 刘平陈冠桦蔡建烟
Owner SOUTH CHINA UNIV OF TECH
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