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A kind of organic compound based on bicarbazole and perylene diimide and its preparation method and application

An organic compound, perylene diimide technology, applied in the field of organic compound synthesis, can solve the problems of limiting the effective separation of exciton diffusion charges, affecting the performance of solar cells, reducing charge mobility, etc. The effect of friendly and convenient industrialized mass production

Inactive Publication Date: 2020-05-05
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, the inventors found that PDI materials still have certain limitations as acceptors: PDI has a large π-conjugated plane, exhibits a strong self-aggregation tendency, and is easy to form a crystal structure in the solid state; at the same time, coplanar intermolecular The strong π-π interaction easily leads to the formation of exciton associations, and excitons are easily captured by it, thus limiting the diffusion of excitons and the effective separation of charges
However, the destruction of the planarity of PDI molecules will reduce the charge mobility, thereby affecting the performance of solar cells.

Method used

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  • A kind of organic compound based on bicarbazole and perylene diimide and its preparation method and application
  • A kind of organic compound based on bicarbazole and perylene diimide and its preparation method and application
  • A kind of organic compound based on bicarbazole and perylene diimide and its preparation method and application

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preparation example Construction

[0043] In yet another specific embodiment of the present invention, a method for preparing the above-mentioned organic compound is provided, and the method includes the step of preparing the organic compound through a Suzuki coupling reaction with biscarbazole borate and bromoperylene diimide. The classic Suzuki coupling reaction is adopted, with mild reaction conditions, simple steps, convenient handling and less pollution.

[0044] The synthetic route is as follows:

[0045]

[0046] Wherein, R is any hydrocarbon group not more than 18 carbon atoms.

[0047] In yet another specific embodiment of the present invention, said R is any hydrocarbon group with no more than 8 carbon atoms.

[0048] In yet another specific embodiment of the present invention, said R is C 5 h 11 or C 6 h 13. The organic compound prepared by the invention effectively changes the energy levels of the perylene diimide LOMO and HOMO, thereby exhibiting more excellent photoelectric properties.

...

Embodiment 1

[0059]

[0060] Under the protection of nitrogen, 150 mg of biscarbazole borate, 800 mg of bromoperylene diimide, 7.16 g of potassium carbonate, 26 mL of water, and 52 mL of toluene were added to the reaction flask, and the mixture was bubbled with nitrogen for 10 minutes. During this process, Add 1 mL of methyltrioctylammonium chloride. Weigh 123.3 mg of tetrakis(triphenylphosphine) palladium and add it into the reaction flask, and continue bubbling for 10 minutes. Turn on the oil bath and heat to 120° C., and the reaction ends after 48 hours. The obtained crude product is separated and purified by thin-layer chromatography to obtain 0.43 g of a reddish-brown product with a yield of 72%.

Embodiment 2

[0062]

[0063] Under the protection of nitrogen, 150mg of biscarbazole borate, 744mg of brominated perylene diimide, 7.16g of potassium carbonate, 26mL of water, and 52mL of toluene were added to the reaction flask, and the mixture was bubbled with nitrogen for 10 minutes. During this process, Add 1 mL of methyltrioctylammonium chloride. Weigh 123.3 mg of tetrakis(triphenylphosphine) palladium and add it into the reaction flask, and continue bubbling for 10 minutes. Turn on the oil bath and heat to 120° C., and the reaction ends after 48 hours. The obtained crude product is separated and purified by thin-layer chromatography to obtain 0.38 g of a reddish-brown product with a yield of 68%.

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Abstract

The invention provides an organic compound based on bicarbazole and perylene diimide, and a preparation method and an application thereof. It is found that two sp<3> hybridized nitrogen atoms in the middle of bicarbazole are connected by a single bond to make a certain angle formed between two the carbazoles with planar configurations, then the bicarbazole is connected with the perylene diimide tosignificantly improve the film formation stacking status of the perylene diimide and significantly change the LUMO and HOMO energy level distribution of the perylene diimide in order to meet the needs of organic solar energy conversion, so the compound has good practical application values.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and specifically relates to an organic compound based on bidicarbazole and perylene diimide, a preparation method and application thereof. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] Perylene diimide (PDI) and its derivatives are planar conjugated fused-ring molecules with excellent physical and chemical properties. The raw materials of PDI molecules are easy to obtain, and the chemical synthesis is simple and easy to modify, which has attracted much attention. Its absorption spectrum generally appears in the visible range from 400 to 600 nm, and its molar extinction coe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D519/00H01L51/42H01L51/46
CPCY02E10/549
Inventor 李刚王心宇李丹丹王帅花徐文波郝品唐波
Owner SHANDONG NORMAL UNIV