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Organic cavity transmission material by using dithiophene pyrrole as core and preparation method and application thereof

A hole transport material, phenopyrrole technology, applied in the field of solar cells, can solve the problems of low efficiency, complex synthesis, poor stability, etc., achieve excellent solubility, simple synthesis route, and improve efficiency

Inactive Publication Date: 2018-04-17
HUAIYIN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although some progress has been made, there are still many problems in the organic hole materials used in PSCs: such as complex synthesis, high cost, poor stability and low battery efficiency, etc.

Method used

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  • Organic cavity transmission material by using dithiophene pyrrole as core and preparation method and application thereof
  • Organic cavity transmission material by using dithiophene pyrrole as core and preparation method and application thereof
  • Organic cavity transmission material by using dithiophene pyrrole as core and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: the synthesis of organic hole transport material

[0024] The synthetic route is as follows

[0025]

[0026] The compound of formula (2) used in this example was synthesized according to literature Liou, G.-S.; , A.; IbrahimDar, M.; Gao, P.; Jankauskas, V.; Jacopin, G.; Kamarauskas, E.; Kazim, S.;Ahmad, S.; Grätzel, M.; . Soc. 2015, 137, 16172-16178 prepared; the compound of formula (1) and other reagents can be obtained commercially.

[0027] Synthesis of the compound of formula (3):

[0028] Under argon protection, 1.05 g of the compound of formula (1), 1.25 g of sodium tert-butoxide, 90 mg of tris(dibenzylideneacetone) dipalladium, 218 mg of 1,1' -Bis(diphenylphosphino)ferrocene, 1.35 g of compound of formula (2) and 15 mL of anhydrous toluene; the reaction system was heated to 110 °C for 8 h and cooled to room temperature, the solvent was distilled off under reduced pressure, and the crude product was passed through the column Analysis (eluent:...

Embodiment 2

[0034] Embodiment 2: the synthesis of organic hole transport material

[0035] Synthesis of the compound of formula (3):

[0036] Under argon protection, 1.05 g of the compound of formula (1), 1.25 g of sodium tert-butoxide, 90 mg of tris(dibenzylideneacetone) dipalladium, 183 mg of 2,2' - Bis-(diphenylphosphino)-1,1'-binaphthalene, 1.35 g of the compound of formula (2) and 15 mL of anhydrous toluene; the reaction system was heated to 110 °C for 8 h and cooled to room temperature, and the solvent was distilled off under reduced pressure , the crude product was purified by column chromatography (eluent: petroleum ether / dichloromethane = 20 / 1~10 / 1) to obtain 1.06 g of the compound of formula (3), a pale yellow solid, with a yield of 68%.

[0037] Synthesis of the compound of formula (4):

[0038] Under argon protection and -78 °C, add 0.8 g of the compound of formula (3) and 10 mL of anhydrous tetrahydrofuran into a 100 mL Schlenk round bottom reaction flask, and then add 1.58...

Embodiment 3

[0042] Embodiment 3: the synthesis of organic hole transport material

[0043] Synthesis of the compound of formula (3):

[0044] Under the protection of argon, 1.05 g of the compound of formula (1), 1.46 g of potassium tert-butoxide, 90 mg of tris(dibenzylideneacetone) dipalladium, 218 mg of 1,1' -Bis(diphenylphosphino)ferrocene, 1.35 g of compound of formula (2) and 15 mL of anhydrous toluene; the reaction system was heated to 110 °C for 8 h and cooled to room temperature, the solvent was distilled off under reduced pressure, and the crude product was passed through the column (eluent: petroleum ether / dichloromethane = 20 / 1~10 / 1) and purified to obtain 59 mg of the compound of formula (3) as a pale yellow solid with a yield of 4%.

[0045] Synthesis of the compound of formula (4):

[0046] Under the protection of argon and at -78 °C, add 0.8 g of the compound of formula (3) and 10 mL of anhydrous tetrahydrofuran into a 100 mL Schlenk round bottom reaction flask, and then a...

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Abstract

The invention discloses an organic cavity transmission material by using dithiophene pyrrole as a core and a preparation method and application thereof. The organic cavity transmission material by using the dithiophene pyrrole as the core has the advantages that the synthesis route is simple, the raw materials are easy to obtain, and the cost is low; the amorphous state is good, and the dissolvingproperty is excellent; proofed by testing results, when the organic cavity transmission material is applied into a perovskite solar battery, the short-circuiting photocurrent density of a battery device reaches 22.6mA cm<2>, the open-loop voltage is 1.01V, the filling factor is 0.71, the photoelectric conversion efficiency reaches 16.2%, and the practical meaning is realized for improving of theefficiency of the perovskite solar battery.

Description

technical field [0001] The invention relates to the technical field of solar cells, in particular to an organic hole transport material with dithienopyrrole as the core, a preparation method thereof and an application in perovskite solar cells. Background technique [0002] As a new generation of photovoltaic technology, perovskite solar cells (Perovskite Solar Cells, referred to as PSCs. Kojima A.; Teshima K.; Shirai Y.; et al. J. Am. Chem. Soc. 2009, 131, 6050-6051) With the advantages of easy adjustment of materials, high efficiency, simple preparation process, and low cost, it has become the most eye-catching new star in solar cells in recent years, and its development is extremely rapid. At present, the highest photoelectric conversion efficiency has exceeded 20% (Saliba, M.; Orlandi , S.; Matsui, T.; Aghazada, S.; et al. Nat. Energy 2016, 1, 15017−15023.). As an important part of PSCs, the hole transport layer is mainly used to collect and transport the holes injected...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/14H01L51/46
CPCC07D495/14H10K85/631H10K85/657Y02E10/549
Inventor 王志辉蔡鹏陈静陈丹豆晨光石慧高萍
Owner HUAIYIN INSTITUTE OF TECHNOLOGY
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