A kind of organic small molecule containing thiazole and its preparation method and application

A small molecule, thiazole-containing technology, applied in the molecular field, can solve problems such as small molecule photovoltaic materials that are rarely used

Active Publication Date: 2021-05-14
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, many high-performance polymer systems based on thiazole units have been widely used (B. Guo, X. Guo, W. Li, X. Meng, W. Ma, M. Zhang, and Y. Li, J. Mater .Chem.A, 2016,4,13251; B.Guo,W.B.Li,X.Guo,X.Y.Meng,W.Ma,M.J.Zhang,and Y.F.Li,Adv.Mater.,2017,29,1702291.) , but it is rarely used in small molecule photovoltaic materials

Method used

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  • A kind of organic small molecule containing thiazole and its preparation method and application
  • A kind of organic small molecule containing thiazole and its preparation method and application
  • A kind of organic small molecule containing thiazole and its preparation method and application

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preparation example Construction

[0066] For the preparation method of the above structure, please refer to Image 6 , Image 6 It is a synthetic route of a thiazole-containing organic small molecule described in the present invention. Such as Image 6 shown, including the following steps:

[0067]

[0068] (1) Dissolve compound 1 in a mixed solvent of chloroform and glacial acetic acid, slowly add N-bromosuccinimide in an ice-water bath and avoid light, remove the ice-water bath after half an hour, and carry out stirring reaction at room temperature for 10 hours for separation and purification Compound 2 was obtained afterward;

[0069] (2) Phosphorus oxychloride and N,N-dimethylformamide were stirred and reacted for 1 to 2 hours in an ice-water bath and an inert gas atmosphere, and then the ice-water bath was removed, and the compound 2 was dissolved in chloroform and used The syringe was added to the product after the reaction of phosphorus oxychloride and N,N-dimethylformamide, stirred and refluxed at...

Embodiment 1

[0090] see Figure 7 , Figure 7 It is a BTTzR synthesis route of a thiazole-containing organic small molecule described in the present invention. Such as Figure 7 As shown, this implementation case shows the synthetic route of thiazole-containing organic small molecules according to the following steps:

[0091]

[0092] Note: R 1 stands for 2-ethylhexyl, R 2 Indicates n-hexyl.

[0093] The detailed synthetic steps of its each step product are as follows:

[0094] Step 1) Synthetic compound 2,2-(5-bromo-4-(2-ethylhexyl)thiophen-2-yl)-5-(4-(2-ethylhexyl)thiophen-2-yl)thiazole[ 5,4-d]oxthiazole;

[0095] With compound 1, i.e. 2,5-bis(4-(2-ethylhexyl)thiophen-2-yl)thiazo[5,4-d]thiazole as raw material, placed in a 100ml single-necked round bottom flask, Chloroform (25ml) and glacial acetic acid (25ml) were then added. N-bromosuccinimide (0.71 g, 4.01 mmol) was slowly added to the one-necked flask under the condition of an ice-water bath protected from light. After ...

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Abstract

The invention discloses a thiazole-containing organic small molecule and its preparation method and application, using a high-performance benzodithiophene unit (BDT) as an electron-donating nucleus, thiazole as a bridging unit, and changing the design of the terminal electron-drawing unit Synthesized a series of brand-new A-D-A conjugated molecules with good solubility and good thermal stability with thiazole as the bridging unit. Carrier mobility and the strong electron-pulling ability of the terminal electron-pulling unit, so this kind of molecule has strong visible light absorption ability, high charge transport performance and suitable electron energy level, suitable as electron donor or electron acceptor material Applied to the preparation of organic solar cells.

Description

technical field [0001] The invention relates to the field of molecular technology, in particular to a thiazole-containing organic small molecule and a preparation method thereof, and the use of the thiazole-containing organic small molecule as an active layer electron donor or electron acceptor material in an organic solar cell (OPV) application. Background technique [0002] As a promising green energy technology, solution-processed organic solar cells have made great progress due to some unique advantages such as low cost, light weight, and the ability to prepare large-area devices. The energy conversion efficiency PCE of organic solar cells based on conjugated polymers or small organic molecules as donors and fullerene derivatives as acceptors has exceeded 10% (J.Wan, X.Xu, G. Zhang, Y. .Li, K.Feng and Q.Peng, Energy Environ.Sci., 2017, 10, 1739; B. Kan, M.Li, Q.Zhang, F.Liu, X.Wan, Y.Wang, W.Ni , G.Long, X.Yang and H.Feng, J.Am.Chem.Soc., 2015, 137, 3886; D.Deng, Y.Zha...

Claims

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Application Information

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Patent Type & AuthorityPatents(China)
IPC IPC(8): C07D519/00H01L51/46
CPCC07D519/00H10K85/649H10K85/655H10K85/657H10K30/00Y02E10/549
Inventor张茂杰叶陈男国霞
OwnerSUZHOU UNIV