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Triarylated amine compound and preparation method thereof, and application to preparation of solar cell

A compound, triarylamine technology, applied in the field of solar cell materials, can solve the problems of high electron recombination rate, low light harvesting ability, aggregation, etc., and achieve low ionization potential, high hole mobility, strong fluorescence performance and photostability Effect

Active Publication Date: 2017-06-13
浙江工业大学上虞研究院有限公司
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  • Abstract
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  • Claims
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Problems solved by technology

[0004] However, the currently developed non-metallic organic dyes also face challenges such as easy aggregation on the semiconductor surface, high electron recombination rate, and low light-harvesting ability.

Method used

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  • Triarylated amine compound and preparation method thereof, and application to preparation of solar cell
  • Triarylated amine compound and preparation method thereof, and application to preparation of solar cell
  • Triarylated amine compound and preparation method thereof, and application to preparation of solar cell

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The synthesis of embodiment 1 compound formula HJ-4

[0032] 1. The synthesis of compound formula IVa

[0033] The compound formula VII (1.13g, 2.0mmol), Pd (PPh 3 ) 4 (0.23g, 0.2mmol), compound formula IX (0.45g, 3.0mmol), potassium carbonate aqueous solution (5mL, 2mol / L) were dissolved in tetrahydrofuran (30mL), N 2 React under protection for about 10 hours. The reaction solution was extracted three times with dichloromethane, the organic layer was washed with water, dried over anhydrous sodium sulfate, the solvent was spin-dried, and the column was separated (V CH2Cl2 :V PE =1:1) to obtain 0.35 g of yellow solid with a yield of 30%. m.p.:210-212℃; 1 H NMR (500MHz, CDCl 3 )δ10.06(s,1H,C H O), 8.04(d, J=8.0Hz, 2H), 7.95(d, J=8.0Hz, 2H), 7.76(d, J=8.3Hz, 2H), 7.68(d, J=8.5Hz, 2H) ,7.61-7.55(m,5H),7.45-7.43(m,2H),7.34(t,J=7.5Hz,2H),7.25-7.21(m,6H),7.14-7.11(m,2H); HREIMS m / z 591.1570[M+H] + , cacld C 38 h 26 N 2 OS 2 for:590.1487.

[0034] 2. Synthesis o...

Embodiment 2

[0036] The synthesis of embodiment 2 compound formula HJ-5

[0037] 1. Synthesis of compound formula IVb

[0038] The compound formula VII (1.13g, 2.0mmol), Pd (PPh 3 ) 4 (0.23g, 0.2mmol), compound formula VIII (0.47g, 3.0mmol), potassium carbonate aqueous solution (5mL, 2mol / L) was dissolved in tetrahydrofuran (30mL), N 2 React under protection for about 10 hours. The reaction solution was extracted three times with dichloromethane, the organic layer was washed with water, dried over anhydrous sodium sulfate, the solvent was spin-dried, and the column was separated (V CH2Cl2 :V PE =1:1) to obtain 0.25 g of orange solid with a yield of 21%. m.p.:117-119℃; 1 H NMR (500MHz, CDCl 3 )δ9.88(s,1H,C HO), 8.04(d, J=8.3Hz, 2H), 7.74(d, J=3.9Hz, 1H), 7.68(d, J=8.3Hz, 2H), 7.63-7.55(m, 5H), 7.44( d,J=6.5Hz,2H)7.34(dd,J=8.7,6.2Hz,3H),7.22(t,J=7.7Hz,4H),7.16-7.12(m,4H).HREIMS m / z 597.1110[ M+H] + , cacld C 36 h 24 N 2 OS 3 for:596.1051.

[0039] 2. Synthesis of compound for...

Embodiment 3

[0041] The synthesis of embodiment 3 compound formula HJ-6

[0042] 1. The synthesis of compound formula IVc

[0043] The compound formula VII (1.13g, 2.0mmol), Pd (PPh 3 ) 4 (0.23g, 0.2mmol), compound formula X (0.42g, 3.0mmol), potassium carbonate aqueous solution (5mL, 2mol / L) was dissolved in tetrahydrofuran (30mL), N 2 React under protection for about 10 hours. The reaction solution was extracted three times with dichloromethane, the organic layer was washed with water, dried over anhydrous sodium sulfate, the solvent was spin-dried, and the column was separated (V CH2Cl2 :V PE =1:1) to obtain 0.46 g of orange solid with a yield of 40%. m.p.:117-119℃; 1 H NMR (500MHz, CDCl 3 )δ9.62(s,1H,C H O), 8.04(d, J=8.4Hz, 2H), 7.71(d, J=8.8Hz, 2H), 7.68(d, J=8.4Hz, 2H), 7.62-7.58(m, 3H), 7.45- 7.43(m,2H),7.35(d,J=8.3Hz,2H),7.33(d,J=3.6Hz,2H),7.23-7.20(m,4H),7.17-7.14(m,3H),7.12 (dd, J=5.0, 3.7Hz, 1H); HREIMS m / z 581.1340[M+H] + , cacldC 36 h 24 N 2 o 2 S 2 for:580.12...

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Abstract

The invention provides a triarylated amine compound and a preparation method thereof, and application to preparation of a solar cell, which are used to solve the problem in the prior art of low photoelectric conversion efficiency of a dye-sensitized solar cell. According to the invention, six triarylated amine dye sensitizers are obtained by synthesizing triarylated amine which serves as a donor, a thiazole-containing conjugate aromatic ring which serves as a bridged bond, and cyanoacetic acid which serves as a receptor. The dye-sensitized solar cell obtained by assembling the compounds which serve as the dye sensitizers has higher photoelectric conversion efficiency, and a new applicable substance is added to screening of the dye sensitizers.

Description

technical field [0001] The invention relates to the technical field of solar cell materials, in particular to triarylamine compounds, their preparation methods, and their application in the preparation of solar cells. Background technique [0002] In order to slow down climate change and solve the world's energy crisis, it is a global demand to find a suitable energy source to replace fossil fuels. Solar energy is an inexhaustible and non-polluting energy source, which is usually converted into electrical energy for use, so the development of solar cells has received considerable attention. In the past decade, dye-sensitized solar cells (DSSCs) have been considered as a better alternative to traditional expensive and inefficient silicon-based solar cells due to their ease of fabrication, high efficiency, and low cost. [0003] Dye sensitizer is the main factor affecting the photoelectric conversion efficiency of DSSC. The research on dye sensitizers at home and abroad is m...

Claims

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Application Information

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IPC IPC(8): C07D417/04C07D417/14H01L51/42H01L51/46
CPCC07D417/04C07D417/14H10K85/653H10K85/656H10K85/655H10K85/631H10K30/00Y02E10/549
Inventor 韩亮许萌何吉高建荣
Owner 浙江工业大学上虞研究院有限公司
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