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Compound bicyclopentane [cd,1m] perylene-1,2,7,8-tetrone as well as preparation method and application thereof

A dicyclopentane and compound technology, applied in the field of photovoltaic cell acceptor materials, can solve the problems of shortening the diffusion distance of excitons, increasing the contact area between electron donor TBP and electron acceptor, and increasing the short-circuit current of photovoltaic cells, so as to shorten the diffusion distance, increase the contact area, and improve the effect of short-circuit current

Active Publication Date: 2015-09-02
常熟紫金知识产权服务有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Accordingly, increasing the contact area between the electron donor TBP and the electron acceptor and shortening the diffusion distance of the excitons can lead to an increase in the short-circuit current of the photovoltaic cell.

Method used

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  • Compound bicyclopentane [cd,1m] perylene-1,2,7,8-tetrone as well as preparation method and application thereof
  • Compound bicyclopentane [cd,1m] perylene-1,2,7,8-tetrone as well as preparation method and application thereof
  • Compound bicyclopentane [cd,1m] perylene-1,2,7,8-tetrone as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Diacenaphthylquinone sulfide (0.79 g, 2 mmol) and copper sulfate (0.32 g, 2 mmol) were added to DMSO (250 mL), heated to 160 °C, and stirred for 6 hours. After filtering and cooling the mother liquor, a dark red precipitate was precipitated. After filtering, a dark red powder of dicyclopenta[cd,lm]perylene-1,2,7,8-tetraketone (0.53 g, 73.4 %) was obtained.

[0016] MS (FD+): 361.1

[0017] UV-vis: λmax = 498 nm.

[0018] 1 H NMR (DMSO-d6): δ = 8.00 - 7.50 (m, 8H)

Embodiment 2

[0020] Add bisacenaphthylquinone sulfide (0.79 g, 2 mmol) and copper sulfate (0.96 g, 6 mmol) into DMSO (250 mL), heat to 160°C, and stir for 6 hours. After filtering and cooling the mother liquor, a dark red precipitate was precipitated. After filtration, a dark red powder of dicyclopenta[cd,lm]perylene-1,2,7,8-tetraketone (0.61 g, 84.5 %) was obtained.

Embodiment 3

[0022] Add bisacenaphthylquinone sulfide (0.79 g, 2 mmol) and copper sulfate (0.64 g, 4 mmol) into DMSO (250 mL), heat to 160 °C, and stir for 6 hours. Filtrate, cool the mother liquor, precipitate a dark red precipitate, and filter to obtain a dark red powder dicyclopenta[cd,lm]perylene-1,2,7,8-tetraketone (0.60 g, 83.1 %).

[0023] It can be seen from Examples 1-3 that with the increase of the molar ratio of bisacenaphthyl quinone sulfide and copper salt, the reaction yield gradually becomes higher, but when the molar ratio is 1:2-1:3, the reaction yield changes not big. Therefore, the preferred molar ratio of diacenaphthyl quinone sulfide to copper salt is 1:2.

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Abstract

The invention discloses a compound bicyclopentane [cd,1m] perylene-1,2,7,8-tetrone and a preparation method thereof. The compound is prepared from di-acenaphthequinone thioether and a copper salt through a heating reaction. The compound bicyclopentane [cd,1m] perylene-1,2,7,8-tetrone disclosed by the invention serves as an electron acceptor material, and the compound is used for manufacturing photovoltaic cells together with tetrabenzyl porphrine (TBP) which functions as an electron donor material, so as to improve the short-circuit current, the fill factor and the photoelectric conversion rate of the photovoltaic cells.

Description

technical field [0001] The invention relates to a photovoltaic cell acceptor material, in particular to a compound dicyclopenta[cd,lm]perylene-1,2,7,8-tetraketone and its preparation method and application. Background technique [0002] The development of organic photovoltaic cells requires high-performance electron donor (Donor) and electron acceptor (Acceptor) materials. The current electron acceptor materials mainly focus on C60 derivatives and C70 derivatives. Among them, the most widely used receptor compound is the C60 derivative PCBM ([6,6]-phenyl C61-butyric acid methyl ester) designed and synthesized by the Wudl research group at the University of California, Santa Barbara, and Professor Li Yongfang from the Institute of Chemistry, Chinese Academy of Sciences, etc. Design and synthesis of ICBA (Indene-C60 or C70 bisadduct) electron acceptor material. The LUMO energy level of these electron acceptor materials is too low, resulting in a low open circuit voltage ...

Claims

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Application Information

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IPC IPC(8): C07C49/665C07C45/68H01L51/46
CPCC07C45/68C07C49/665H10K85/624Y02E10/549Y02P70/50
Inventor 张超智袁阳蒋威
Owner 常熟紫金知识产权服务有限公司
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