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Hole transport material based on silole fused heterocycle and preparation method and application of hole transport material

A hole transport material, fused heterocycle technology, applied in the field of hole materials, can solve the problems of high synthesis and preparation cost, poor stability of perovskite solar cells, limited wide-scale application, etc., to improve efficiency, enhance interfacial interaction, The effect of improving performance

Active Publication Date: 2021-05-11
HUAIYIN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the cost of synthesis and preparation of Spiro-OMeTAD molecules is high, and the stability of perovskite solar cells prepared from them is poor, which limits their commercialization and wide-ranging applications.

Method used

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  • Hole transport material based on silole fused heterocycle and preparation method and application of hole transport material
  • Hole transport material based on silole fused heterocycle and preparation method and application of hole transport material
  • Hole transport material based on silole fused heterocycle and preparation method and application of hole transport material

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] This embodiment provides a hole-transporting material based on a silole condensed heterocycle, the chemical formula of which is shown in formula (6):

[0030]

[0031] The preparation method of above-mentioned hole material (formula (6) compound) is as follows:

[0032] The compound of formula (1) used in this embodiment is according to literature Q.Yu, W.Fu, J.Wan, X.Wu, M.Shi, H.Chen.ACS Appl.Mater.Interfaces 6(2014)5798-5809. Prepared; the compound of formula (5) according to literature Y.-K.Peng, K.-M.Lee, C.-C.Ting, M.-W.Hsu, C.Y.Liu.J.Mater.Chem.A, 2019 ,7,24765-24770. Prepared; other reagents can be obtained through commercial means.

[0033] S1: make the compound of formula (1) and the compound of formula (2) undergo cyclization coupling reaction to generate the compound of formula (3);

[0034]

[0035] Specifically, this step is as follows: under the protection of argon, at a low temperature of -78°C, add 981 mg of the compound of formula (1) dissolved...

Embodiment 2

[0047] This embodiment is roughly the same as Embodiment 1, the main difference is:

[0048] S1: Synthesis of the compound of formula (3);

[0049] Under the protection of argon, under the condition of low temperature -78°C, add 981 mg of the compound of formula (1) dissolved in 30 mL of anhydrous tetrahydrofuran into a 100 mL eggplant-shaped reaction flask, and after 5 minutes of low temperature reaction, slowly add 1.56 mL of n-butyllithium ( 2.4mol / L), add 529mg of the compound of formula (2) after 1 hour of warm reaction, turn off the refrigeration, slowly return to room temperature; react for 8 hours. Water and ethyl acetate were added for extraction, the organic phase was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 522 mg of the compound of formula (3). It is a yellow-green viscous liquid with a yield of 46%.

[0050] S2: Synthesis of the compound of formula (4);

[0051] Into a 100mL single-necked round-b...

Embodiment 3

[0055] This embodiment is roughly the same as Embodiment 1, the main difference is:

[0056] S1: Synthesis of the compound of formula (3);

[0057] Under the protection of argon, under the condition of low temperature -78°C, add 981 mg of the compound of formula (1) dissolved in 30 mL of anhydrous tetrahydrofuran into a 100 mL eggplant-shaped reaction flask, and after 5 minutes of low temperature reaction, slowly add 1.56 mL of n-butyllithium ( 2.4mol / L), add 794mg of the compound of formula (2) after warm reaction for 1h, turn off the refrigeration, slowly return to room temperature; react for 12h. Water and ethyl acetate were added for extraction, the organic phase was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 749 mg of the compound of formula (3). It is a yellow-green viscous liquid with a yield of 66%.

[0058] S2: Synthesis of the compound of formula (4);

[0059] In a 100mL single-necked round-bottom fla...

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Abstract

The invention relates to the technical field of hole materials, and discloses a hole transport material based on silole fused heterocycle. The hole material uses silole fused heterocycle as a central core, and thiophene-triphenylamine as a peripheral modification group, the chemical structural formula is multi-S structural characteristics of hole molecules, the interface interaction between a hole transport layer and a perovskite layer is improved, the electron-hole separation and transmission efficiency is enhanced, and the hole extraction efficiency is improved. The silicon-containing fused pentacyclic ring hole transport material is applied to a perovskite solar cell, the photoelectric conversion efficiency of a device of the hole transport material can reach 19.41%, efficient device stability performance is shown, and the hole transport material has high commercial application value.

Description

technical field [0001] The invention relates to the technical field of hole materials, in particular to a hole transport material based on a silole condensed heterocycle, a preparation method and application thereof. Background technique [0002] As a new generation of photovoltaic technology, perovskite solar cells (Perovskite Solar Cells, referred to as PSCs) have the advantages of simple preparation process, easy modulation of materials, and low cost. The latest certified efficiency has reached 25.2% (National Renewable Energy Laboratory, NREL, 2019). As an important part of PSCs, the hole transport layer plays the important role of collecting the photogenerated holes of the perovskite absorbing layer and transporting them to the counter electrode. to a vital impact. At present, the most widely used and efficient hole transport material in perovskite solar cells is 2,2',7,7'-tetrakis[N,N-bis(4-methoxyphenyl )amino]-9,9'-spirobifluorene (Spiro-OMeTAD). However, the cos...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/10H01L51/42H01L51/46
CPCC07F7/0816H10K85/40H10K30/00Y02E10/549
Inventor 王志辉邹于杰陈瑾张淦任炎炎郑菲陈静茆平胡涛
Owner HUAIYIN INSTITUTE OF TECHNOLOGY
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