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Benzo terthiophene compound as well as preparation method and usage thereof

A compound, trifluoromethyl technology, applied in the field of benzotrithiophene compounds and their preparation, can solve the problems of difficult purification of conjugated polymers, poor device repeatability, etc.

Active Publication Date: 2013-09-11
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, organic solar cells mostly use conjugated polymers. However, conjugated polymers are difficult to purify and have poor device repeatability. Compared with conjugated polymers, organic small molecule materials have a more definite molecular structure, are easy to modify and purify, and have good reproducibility. etc. Therefore, it has become one of the research hotspots in the field of organic solar cells in recent years.

Method used

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  • Benzo terthiophene compound as well as preparation method and usage thereof
  • Benzo terthiophene compound as well as preparation method and usage thereof
  • Benzo terthiophene compound as well as preparation method and usage thereof

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preparation example Construction

[0086] Preparation method of benzotrithiophene compound

[0087] The benzotrithiophene compounds of the present invention can be prepared by conventional synthesis methods known to those skilled in the art. In a class of preferred embodiments of the present invention, the preparation method of the compound comprises the step of performing Stille coupling reaction on the compound of formula IV and the compound of formula V in the presence of a catalyst, thereby forming the compound of formula I.

[0088]

[0089] In the formula, the definition of X is the same as above; R 7 Is methyl, n-butyl or tert-butyl; L is I or Br.

[0090] The catalyst can be a conventional catalyst used in the coupling reaction, preferably a palladium catalyst or a combination of a palladium catalyst and a ligand.

[0091] Palladium catalysts include but are not limited to: PdM 2 , Pd(MeCN) 2 Cl 2 , Pd(PhCN) 2 Cl 2 , Pd(dppf)Cl 2 , Pd(dppe)Cl 2 , Pd(dppb)Cl 2 , Pd(dppp)Cl 2 , Pd(dppm)Cl 2...

Embodiment 5

[0251] Embodiment 5: UV-visible absorption spectrum test

[0252] The ultraviolet-visible absorption spectrum test of compound BTT-hTBT and BTT-hTBTT in chlorobenzene solution:

[0253] The ultraviolet-visible absorption spectrum of above-mentioned compound is carried out on the ultraviolet-visible spectrophotometer, wherein the used solvent of solution absorption spectrum is chlorobenzene, and concentration is 10 -5 mol / L; Take 2mL of the solution of each compound and add it to a quartz cuvette, put it into a mapada UV-3300 UV-Visible spectrophotometer, after calibrating the baseline and blank, test the absorption of the solution in the range of 200-1000nm spectrum. The test results show (such as figure 1 shown), the compound solution described in this application has good absorption in the visible light region, which meets the basic light absorption requirements of organic solar cell donor materials. At the same time, the increase of the branched chain conjugated system m...

Embodiment 6

[0256] Embodiment 6: Cyclic voltammetry test

[0257] Cyclic voltammetry tests on compounds BTT-hTBT, BTT-hTBTT, BTT-ehDPP and BTT-DTCNOeh:

[0258] The energy level of the highest occupied orbital (HOMO) and the lowest unoccupied orbital (LUMO) of the molecule can be calculated by measuring the redox potential of the molecule by cyclic voltammetry. In this embodiment, electrochemical workstations are used to test electrochemical properties. The electrolytic cell is a three-electrode system (a glassy carbon electrode is a working electrode, a glass wire electrode is an auxiliary electrode, and a silver / silver chloride electrode is a reference electrode). Ferrocene was used as internal standard, dried dichloromethane or acetonitrile was used as solvent, 0.1mol / L tetrabutylammonium hexafluorophosphate was used as supporting electrolyte, and the scanning speed was 50mV / S. Under the protection of argon, scan to obtain the cyclic voltammetry curve (such as image 3 shown), the HO...

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Abstract

The invention relates to benzo terthiophene compound as well as a preparation method and usage thereof. The structure of the benzo terthiophene compound is expressed by a formula I, and in the formula, the definition of X is described in the description. The benzo terthiophene compound provided by the invention has a large phi conjugated and soluble mother nucleus structure unit and a conjugated electron donor and / or receptor side chain with a push-pull structure and is a low-energy gap micro-molecular compound, and the benzo terthiophene compound has an extensive application prospect in solar cell devices.

Description

technical field [0001] The invention belongs to the technical field of solar cell materials, and in particular relates to a benzotrithiophene compound and a preparation method and application thereof. Background technique [0002] Organic solar cells are a new type of solar cells, which have the advantages of diverse chemical structures, roll-to-roll large-area production, flexibility, lightness, and relatively low cost. One of them has important development and application prospects. [0003] At present, organic solar cells mostly use conjugated polymers. However, conjugated polymers are difficult to purify and have poor device repeatability. Compared with conjugated polymers, organic small molecule materials have a more definite molecular structure, are easy to modify and purify, and have good reproducibility. Therefore, it has become one of the research hotspots in the field of organic solar cells in recent years. [0004] How to make the donor and acceptor (PCBM) form ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/16C07D519/00H01L51/46
CPCY02E10/549
Inventor 张文俊方俊锋闵超张曲吴玉雷刘菁李晓冬
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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