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Thiophene/selenophene acene fused perylene bisimide derivative and application thereof in organic solar cells

A technology of perylene imide and derivatives, applied in the field of organic optoelectronic functional materials and device preparation

Active Publication Date: 2016-08-31
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, like solar cells based on fullerene acceptors, the open circuit voltage of most peryleneimide dimer acceptor solar cell devices is between 0.7 and 0.85 eV, which limits the solar energy based on peryleneimide acceptors. Further improvements in battery efficiency

Method used

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  • Thiophene/selenophene acene fused perylene bisimide derivative and application thereof in organic solar cells
  • Thiophene/selenophene acene fused perylene bisimide derivative and application thereof in organic solar cells
  • Thiophene/selenophene acene fused perylene bisimide derivative and application thereof in organic solar cells

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: the preparation of compound 1

[0035]

[0036] (1) Synthesis of compound M2.

[0037] Dissolve 2.0 g M1 in 100 mL CHCl 3 , add 7.0g K 2 CO 3 , add dropwise 10mL Br 2 , Stir at 50°C for 12h. Cool to room temperature, add saturated N 2 SO 3 solution to remove excess bromine, followed by saturated NHCO 3 aqueous solution, the organic phase was washed with water and spin-dried. Column chromatography was performed with dichloromethane:petroleum ether=3:2 (v / v) as the eluent to obtain a red solid with a yield of 68%. Mass spectrum: 1031.7. Elemental analysis: theoretical value C: 74.61%, H: 8.71%, N: 2.72% experimental value C: 74.49%, H: 8.86%, N: 2.88%.

[0038] (2) Synthesis of compound M3.

[0039] 5.0g copper powder is placed in the 500ml beaker, add 100mL acetone, add 3g I 2 , stirred at room temperature for 30 minutes. Suction filtration, pour the obtained solid into a beaker, add 100 mL of acetone:concentrated hydrochloric acid=1:1 (v / v)...

Embodiment 2

[0046] Embodiment 2: the preparation of compound 2

[0047] Compound 2 was prepared using the same method as compound 1, except that the raw material M1 was replaced by a perylene imide with 11 carbon alkyl chains as the substituent on the N, and the corresponding raw material 1-pentyl-1-hexylamine was obtained from Purchased from Beijing Lin En Company. Mass spectrum: 1556.1. Elemental analysis: theoretical value C: 77.19%, H: 6.87%, N: 3.60% experimental value C: 77.28%, H: 6.68%, N: 3.65%.

Embodiment 3

[0048] Embodiment 3: the preparation of compound 3

[0049] Compound 3 was prepared by the same method as compound 1, except that the raw material M1 was replaced by peryleneimide whose substituent on N was the corresponding alkyl chain. Mass spectrum: 2230.5. Elemental analysis: theoretical value C: 79.66%, H: 9.22%, N: 2.51% experimental value C: 79.68%, H: 9.24%, N: 2.52%.

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Abstract

The invention discloses a compound with thiophene / selenophene acene fused perylene bisimide as a skeleton. A synthesis method is simple and easy to operate, and is suitable for wide application. The thiophene / selenophene acene fused perylene bisimide derivative can be used as a receptor material for preparing organic solar cell devices, has high efficiency and high open circuit voltage, and can be widely applied in the field of organic solar cells.

Description

technical field [0001] The invention relates to a thiophene / selenophenacene fused perylene imide derivative and its application in organic solar cell materials, belonging to the technical field of organic photoelectric functional materials and device preparation. Background technique [0002] Bulk heterojunction solar cells have the characteristics of low cost, small weight, flexibility and processability, and have received extensive attention and research. A bulk heterojunction solar cell includes a donor material and an acceptor material. Among them, fullerene derivatives (PCBM) are in the current solar acceptor materials due to their good electron affinity, high electron mobility, non-directional charge transport characteristics and nanoscale network structure. Dominance (Acc. Chem. Res. 2015, 48, 2803-2812; J. Mater. Chem. A 2015, 3, 20516-20526). However, fullerene acceptors also have some disadvantages, such as narrow absorption range in the visible light region, poo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00H01L51/46
CPCC07D519/00H10K85/657H10K30/20Y02E10/549
Inventor 杨楚罗张晨
Owner WUHAN UNIV
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