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Cross-shaped small organic molecule hole transport material and preparation method

A hole-transporting material and cross-shaped technology, which is applied in the field of solar cell materials, can solve the problems of low photoelectric conversion efficiency of all-inorganic perovskites, and achieve improved photoelectric conversion efficiency and current density, good photoelectric conversion efficiency, and high device efficiency. Effect of open circuit voltage and short circuit current

Inactive Publication Date: 2019-06-21
NANCHANG HANGKONG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Aiming at the problem of low photoelectric conversion efficiency of all-inorganic perovskite in the prior art, the purpose of the present invention is to provide a oligothiophene derivative organic small molecule with a cross structure, good hydrophobicity and organic solubility Hole transport material, used in perovskite solar cells, has matching energy levels, can absorb red light, and can greatly improve the current density and photoelectric conversion efficiency of perovskite solar cells

Method used

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  • Cross-shaped small organic molecule hole transport material and preparation method
  • Cross-shaped small organic molecule hole transport material and preparation method
  • Cross-shaped small organic molecule hole transport material and preparation method

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Embodiment 1

[0021] A kind of organic small molecule hole-transporting material whose chemical structural formula is a cross type oligothiophene derivative class I, and its synthetic route is as follows:

[0022]

[0023] Synthesis of intermediate 2 (5-hexyl-2,2'-bithiophene):

[0024] Under the protection of argon, dissolve bithiophene (16.6g, 100mmol) in 150mL of anhydrous tetrahydrofuran, cool to -78°C, slowly add n-butyllithium (2.5M, 44mL) dropwise, and stir at -78°C for 0.5 After 1 hour, stir at room temperature for 1 hour, cool to -78°C again, add n-bromohexane (18.15 g, 110 mmol), and stir overnight. The reaction was terminated by adding ice water, extracted with ether, and the organic phases were combined. Washed three times with saturated sodium bicarbonate solution, then washed three times with saturated sodium chloride solution, dried with anhydrous sodium sulfate, spin-dried the solvent with a rotary evaporator, and distilled under reduced pressure to obtain a colorless li...

Embodiment 2

[0040] A chemical structural formula is an oligothiophene organic small molecule hole transport material of formula II, and its synthesis route is as follows:

[0041]

[0042] Synthesis of intermediate 2 (5-octyl-2,2'-bithiophene):

[0043] Under the protection of argon, dissolve bithiophene (5g, 30.1mmol) in 150mL of anhydrous tetrahydrofuran, cool to -78°C, slowly add n-butyl lithium (2.5M, 13.2mL) dropwise, and stir at -78°C After 0.5 hours, stir at room temperature for 1 hour, cool to -78°C again, add n-octane bromide (6.39 g, 33.1 mmol), and stir overnight. The reaction was terminated by adding ice water, extracted with ether, and the organic phases were combined. Washed three times with saturated sodium bicarbonate solution, then washed three times with saturated sodium chloride solution, dried with anhydrous sodium sulfate, spin-dried the solvent with a rotary evaporator, and distilled under reduced pressure to obtain a colorless liquid with a yield of 65%.

[004...

Embodiment 3

[0059] The perovskite solar cells were prepared by applying cross-shaped oligothiophene derivatives organic small molecule hole transport materials. Perovskite solar cells consist of a transparent base, an electron transport layer, a hole transport layer, and a counter electrode. A light-harvesting layer and a hole-transporting layer are sequentially distributed between the transparent substrate and the carbon counter electrode. The transparent base layer is conductive glass FTO; the electron transport layer is composed of dense titanium dioxide and mesoporous titanium dioxide layers; the light harvesting layer is a perovskite layer (CsPbBr 3 ); the electrodes are Ag, Au or carbon electrodes. The hole transport layer contains the cross-shaped oligothiophene derivative organic small molecule hole transport material of the present invention.

[0060] Under atmospheric conditions, rinse the etched FTO thoroughly with detergent, acetone, isopropanol, ethanol, and deionized water...

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Abstract

The invention provides a cross-shaped small organic molecule hole transport material and a preparation method. The preparation method comprises the following steps: uniformly mixing 5-hexyl-5'-trimethyl-2,2'-bithiophene or 5-octyl-5'-trimethyl-2,2'-bithiophene with 3,3',5,5'-tetrabromo-2,2'-bithiophene in methylbenzene at a molar ratio of 1:(4-6); performing a reaction at the temperature of 90-120DEG C for 18-25h, cooling to room temperature and adding silica gel powder for spin drying; separating and purifying a coarse product after spin drying with dichloromethane and n-hexane at a ratio of1:(5-20) as an eluting agent to obtain the cross-shaped small organic molecule hole transport material which is shown in the structural formula I as shown in the specification or the structural formula II as shown in the specification. Due to the 'x' rotary cross-shaped structure of the hole transport material, the excessive crystallization can be effectively inhibited, so that a thiophene derivative have good solubility and excellent hole transport performance under the condition that no excessive alkyl substituted units are introduced; the current density and the photoelectric conversion efficiency of a device can be greatly improved after the cross-shaped small organic molecule hole transport material is applied in an all-inorganic perovskite solar cell.

Description

technical field [0001] The invention relates to a cross-shaped oligothiophene derivative organic small molecule hole transport material and a preparation method thereof, specifically belonging to the technical field of solar cell materials. Background technique [0002] Since Professor Tsutomu Miyasaka of Toin University of Yokohama first reported perovskite solar cells in 2009, through the improvement of materials and the optimization of device structure, the research of perovskite solar cells has made a major breakthrough, which is currently the closest to commercialization. Third generation solar cells. In the perovskite solar cell structure, the hole transport material is very important and is one of the key factors affecting the performance of the cell. The most classic hole transport material is Spiro-OMeTAD. The spiro-ring central unit and bulky diphenylamine substituting unit endow Spiro-OMeTAD with a unique cross structure, which weakens the intermolecular packing ...

Claims

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Application Information

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IPC IPC(8): C07D333/08H01L51/46
CPCY02E10/549Y02P70/50
Inventor 张余宝任福梦宫动飞陈志鸿
Owner NANCHANG HANGKONG UNIVERSITY
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