d-a type small molecule compound and its preparation method and application

A small molecular compound, D-A technology, applied in the field of solar cells, achieves the effect of strong transfer ability, stable positive ions, and enhanced electron donating ability

Active Publication Date: 2018-06-08
NANCHANG HANGKONG UNIVERSITY
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Problems solved by technology

So far, the photovoltaic performance of small-molecule solar cells has been greatly improved, especially the photoelectric conversion efficiency of the device has been greatly improved, but the matching problem between the absorption spectrum of small-molecule materials and the solar spectrum is still a constraint for organic small-molecule materials. Key factor for improved efficiency of molecular solar cells

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  • d-a type small molecule compound and its preparation method and application
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preparation example Construction

[0028] The present invention also provides a preparation method for the D-A type small molecule compound described in the above technical scheme, comprising the following steps:

[0029] Under a protective gas atmosphere, the compound having the structure shown in formula IV, the electron-withdrawing monomer and the catalyst are reacted in an organic solvent system to obtain the D-A small molecule compound with the structure shown in formula I, formula II or formula III;

[0030]

[0031] The electron-withdrawing monomer is malononitrile, 2-ethylhexyl cyanoacetate or 3-ethylrhodanine.

[0032] In the present invention, the compound having the structure shown in formula IV, the electron-withdrawing monomer and the catalyst are reacted in an organic solvent system under a protective gas atmosphere to obtain the D-A type small molecule compound described in the above technical scheme. In the present invention, when the electron-withdrawing monomer is malononitrile, the prepare...

Embodiment 1

[0096] Under argon protection, 0.2 g (0.277 mmol) of a compound represented by the formula IV, 5 mL of CH 2 Cl 2 and 54mg of malononitrile (0.831mmol); 15mg of L-alanine was dissolved in 4.5mL of absolute ethanol, and the resulting L-alanine solution was added dropwise to the flask, and the reaction was stirred at 40°C overnight;

[0097] Add 30mL of water to the resulting reaction solution and add 50mLCH 2 Cl 2 For extraction, the obtained organic layer was washed three times with 0.36 g / mL brine successively, filtered, and the solvent was distilled off under reduced pressure at a vacuum degree of 0.1 MPa and a distillation temperature of 35° C. to obtain a crude product;

[0098] The crude product that obtains is carried out column chromatography purification, and column chromatography adopts silica gel column, and the eluent of column chromatography is the CH that volume ratio is 2:1 2 Cl 2 and n-hexane to obtain 0.098 g of dark red solid.

[0099] The yield of the pr...

Embodiment 2

[0104] Under argon protection, 0.2 g (0.277 mmol) of a compound having a structure shown in Formula IV, 28 mL of CH 2 Cl 2 , 1.35mL (6.73mmol) 2-ethylhexyl cyanoacetate and catalytic amount of triethylamine, the resulting mixed solution was stirred and reacted at room temperature for 12h;

[0105] The obtained reaction solution was distilled off under reduced pressure to remove the solvent under the conditions of a vacuum degree of 0.1 MPa and a distillation temperature of 35° C. to obtain a crude product;

[0106] The obtained crude product is purified by column chromatography, the column chromatography adopts a silica gel column, and the eluent of the column chromatography is CH with a volume ratio of 2:1. 2 Cl 2 and n-hexane to obtain 0.15 g of dark red solid.

[0107] The yield rate of the product calculated by the present invention is 50%.

[0108] The present invention carries out proton nuclear magnetic resonance spectrum measurement with the deep red solid that obt...

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Abstract

The present invention provides D-A type small molecule compound having the structure shown in formula I, formula II or formula III, with phenothiazine as electron-donating group, with malononitrile, 2-ethylhexyl cyanoacetate or 2‑ethylrhodanine as an electron-withdrawing group. In the present invention, there is a phenomenon of internal charge transfer in the small molecules of the D-A structure, which helps to improve the absorption performance of the material; the electron-withdrawing group can adjust the energy level of the small molecule combination of the material to obtain good performance Narrow-band photovoltaic materials. Moreover, phenothiazine itself has moderate steric deformability and the introduction of side chain alkyl makes it have a non-planar geometric configuration. The N and S atoms on the phenothiazine unit help to enhance the electron donation of the main chain of the molecule. ability. Experimental results show that the solar cell device including the D-A type small molecule compound layer provided by the present invention has a relatively high photoelectric energy conversion efficiency of about 2.8%.

Description

technical field [0001] The invention relates to the technical field of solar cells, in particular to a D-A type small molecule compound and its preparation method and application. Background technique [0002] Organic solar cells are another new type of non-fossil energy application after inorganic solar cells, which is very in line with the development requirements of clean and pollution-free renewable energy. Organic solar cells are thinner, more flexible, and cheaper, and come in a wider variety of colors, shapes, and transparency. There are two types of organic solar cell materials: small molecules and polymers. Currently, the blend system of polymer donors and fullerene acceptors is the most efficient. However, the molecular structure, molecular weight, and purity of polymers are uncertain, which will cause differences in the properties of different batches of materials, which may lead to batch instability in industrial production in the future. Compared with polymer ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/14H01L51/46
CPCC07D417/14H10K85/657Y02E10/549
Inventor 秦元成李曼曼刘书强罗旭彪李明俊
Owner NANCHANG HANGKONG UNIVERSITY
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