Organic solar cell acceptor material and preparation method thereof

A technology for solar cells and organic solar energy, applied in the field of solar cells, can solve the problems of low carrier mobility and low conversion efficiency of organic semiconductor cells, and achieve the effects of strong light absorption intensity, easy purification, and broad spectrum absorption

Inactive Publication Date: 2021-03-09
黄培钧
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, compared with polycrystalline silicon and monocrystalline silicon cells, the conversion efficiency of organic semiconductor cells is still low, and there are problems such as low carrier mobility, which have not yet been marketed on a large scale.

Method used

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  • Organic solar cell acceptor material and preparation method thereof
  • Organic solar cell acceptor material and preparation method thereof
  • Organic solar cell acceptor material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] This example is used to illustrate the preparation method of the intermediate 5 for the synthesis of organic solar acceptor cell materials. The synthetic steps of intermediate 5 are as follows:

[0037] The process from 9-(4-bromophenyl)-3,6-dibromocarbazole and biboronic acid pinacol ester to the synthesis of intermediate 5 is as follows:

[0038] step one:

[0039]

[0040] Get 12.00g of 9-(4-bromophenyl)-3,6-dibromocarbazole (25mmol) and 22.20g of biboronic acid pinacol ester (87.5mmol) and join in the reactor, add 0.96g of [ 1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (2.6mmol), 8.59g of methyl acetate and 75mL of dimethyl sulfoxide (DMSO), reacted at 80°C for 24h, the reaction After cooling, 375 mL of water was added to dilute the reaction solution, and extracted with dichloromethane. After being spin-dried, 13.20 g of intermediate 1 was obtained by column chromatography with a yield of 85%. The structural formula was confirmed by NMR. 1 H NMR ...

Embodiment 2

[0053] Embodiment 2: Synthesis of organic solar cell acceptor material CzTPFCN

[0054] When the terminal group is selected from A1, the reaction scheme is:

[0055]

[0056] Take 4.6g of intermediate 5 (5mmol) prepared in Example 1 and add it to the reactor, add 1.1g of malononitrile (16mmol) and 50mL of chloroform, stir and react at room temperature for 0.5h, then slowly add 1.6g of triethylamine The reaction was continued for 20 min. After the reaction was completed, it was quenched by adding ice water, extracted with dichloromethane, and then separated by column chromatography to obtain 4.6 g of CzTPFCN as a yellow solid with a yield of 86%. Spectrum see figure 1 and figure 2 : 1 H NMR (400MHz, CDCl 3 )δ9.17-9.13(m,3H),8.57-8.56(m,3H),8.37-8.35(m,3H),8.29-8.28(m,2H),7.99(s,3H),7.89-7.81( m,6H),7.66-7.62(m,5H),7.30-7.28(m,3H). 13 C NMR (100MHz, CDCl 3 )δ161.2, 161.2, 161.2, 151.5, 151.5, 151.5, 142.5, 142.3, 141.1, 141.1, 141.1, 134.9, 134.9, 133.5, 133.5, 124.1,...

Embodiment 3

[0058] Embodiment 3: the synthesis of organic solar cell acceptor material CzTPFTC

[0059] When the terminal group is selected from A4, the reaction scheme is as follows:

[0060]

[0061] Get the intermediate 5 (5mmol) prepared by 4.6g embodiment 1 and join in the reactor, add 3.2g of 1,3-diethyl-2-thiobarbituric acid (16mmol) and 50mL chloroform, at room temperature After stirring and reacting for 0.5h, slowly add 1.6g triethylamine to continue the reaction for 20min. After the reaction, add ice water to quench, and extract with dichloromethane, then carry out column chromatography to obtain 6.2g CzTPFCN of yellow solid. The yield is 84%. 1 H NMR (400MHz, CDCl 3 )δ9.16(d,J=1.4Hz,2H),9.09(d,J=1.4Hz,1H),8.34–8.24(m,5H),7.94–7.77(m,9H),7.64(dd,J =7.5,1.5Hz,2H),7.56(s,3H),7.40–7.30(m,6H),5.26(q,J=6.3Hz,6H),4.16(q,J=6.3Hz,6H),1.17 (t,J=6.3Hz,18H). 13 C NMR (100MHz, CDCl 3 )δ175.9,161.2,126.2,158.0,150.3,148.5,144.6,137.0,136.5,134.9,133.8,133.5,132.9,131.8,129.0,128.6,1...

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Abstract

The invention discloses an organic solar cell acceptor material and a preparation method thereof, and the method comprises the following steps: step 1, reacting 9-(4-bromophenyl)-3,6-dibromocarbazolewith bis(pinacolato)diboron to generate an intermediate 1; step 2, carrying out Suzuki coupling on the intermediate 1 and 5-bromothieno[2,3-B] pyridine to generate an intermediate 2; step 3, reactingthe intermediate 2 with N-bromo-succinimide (NBS) to generate an intermediate 3, and further reacting the intermediate 3 with bis(pinacolato)diboron to generate an intermediate 4; step 4, performing Suzuki coupling on the intermediate 4 and substituted 5-bromo-2-furan formaldehyde to generate an intermediate 5; and step 5, carrying out a Knoevenagel condensation reaction on the intermediate 5 anda terminal group to generate a final product. The material not only can be used as an electron acceptor in an organic solar cell, but also can be used as an additive material for regulating and controlling a donor/acceptor interface of a ternary blending organic solar cell.

Description

technical field [0001] The invention belongs to the field of solar cells, and in particular relates to an organic solar cell acceptor material and a preparation method thereof. Background technique [0002] Traditional energy sources such as coal, oil, natural gas and other mineral energy are decreasing day by day, but the pollution of human's living environment and natural environment is becoming more and more serious. The demand for mineral energy is increasing day by day, while the earth's reserves are decreasing. In this context, a series of clean energy such as solar energy and wind energy, as an inexhaustible green new energy, has attracted more and more attention of scientists. How to replace traditional mineral energy with solar energy to protect the environment has become a research hotspot and the focus of industrial development in various countries. In the past few decades, due to the rapid development of inorganic semiconductor materials such as monocrystalline...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00H01L51/42H01L51/46
CPCC07D519/00H10K85/653H10K85/626H10K85/654H10K85/6576H10K85/657H10K30/20H10K85/6572Y02E10/549
Inventor 不公告发明人
Owner 黄培钧
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