Tri -bodied Fullene derivatives and their preparation methods and applications

A fullerene derivative, fullerene technology, applied in the preparation of organic compounds, the preparation of carboxylic acid nitriles, chemical instruments and methods, etc., can solve the problem of curbing the development of organic polymer heterojunction solar cells and limiting fullerenes The commercial application of derivatives, and the lack of research on new fullerene derivative acceptor materials, etc., can enhance the self-assembly performance, improve the photoelectric conversion efficiency, and improve the LUMO energy level.

Active Publication Date: 2017-08-01
苏州尚柔新能源有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the nearly two decades of development, many different kinds of conjugated polymer donor materials have been synthesized, but there is little research on new fullerene derivative acceptor materials. Fullerene with excellent photovoltaic performance Derivatives are much less
These greatly limit the commercial application of fullerene derivatives and curb the development of organic polymer heterojunction solar cells

Method used

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  • Tri -bodied Fullene derivatives and their preparation methods and applications
  • Tri -bodied Fullene derivatives and their preparation methods and applications
  • Tri -bodied Fullene derivatives and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] A method for preparing a triplet fullerene derivative with cooperative assembly performance, specifically comprising the following steps:

[0070] (1) Phosphorus tribromide (0.40 g, 1.48 mmol) in CH 2 Cl 2 (2 mL) solution was added to 3,4,5-trioctyloxybenzyl alcohol (0.34 g, 0.70 mmol) in CH under ice-cooling 2 Cl 2 (4 mL) reaction in the solution, stirred at room temperature for 3h to obtain 3,4,5-trioctyloxybenzyl bromide;

[0071] (2) In acetonitrile (10 mL) solution, 3,4,5-trioctyloxybenzyl bromide (0.24 g, 0.43 mmol) and trimethylsilyl cyanide (90 µL) were dissolved in tetrabutylammonium fluoride (700 µL) was activated at room temperature for 2.5h to obtain 3,4,5-trioctyloxycyanide;

[0072](3) Under argon protection, a solution of sodium methoxide (0.03 g, 0.63 mmol) in ethanol (2 ml) was added dropwise to 3,4,5-trioctyloxycyanide (0.11 g, 0.21 mmol) under reflux conditions React with p-hydroxybenzaldehyde (0.03 g, 0.21 mmol) in ethanol (4 mL) for 12 hours to...

Embodiment 2

[0085] According to the preparation steps of Example 1, the carbon chain length of the alkoxy group of the substituted benzyl alcohol compound can be changed to 4-20, and can be replaced by other flexible functional groups at the same time, which can be used to replace the phenolic hydroxyl group in p-hydroxybenzaldehyde. Para-position introduces electron-withdrawing groups such as nitro, cyano, etc., using C 70 、C 84 etc instead of C 60 ; Triad fullerene derivatives with various structures can be obtained.

[0086] For example, replace 3,4,5-trioctyloxybenzyl alcohol with 3,4,5-tris(2-(2-(2-methoxyethoxy)ethoxy)ethoxybenzyl alcohol, and p-Hydroxybenzaldehyde is replaced by 3-nitro4-hydroxybenzaldehyde; the reaction results in a three-body fullerene derivative, referred to as PCBB-NO 2 -CN-6C-EG, the structural formula is:

[0087]

[0088] Include the following steps:

[0089] (1) Phosphorus tribromide (0.38 g, 1.48 mmol) in CH 2 Cl 2 (2 mL) solution was added to 3,...

Embodiment 3

[0096] An active layer material for an organic polymer solar cell, comprising the above-mentioned three-body fullerene derivative and a donor material. Taking PCBB-CN-C8 as the acceptor material and P3HT as the donor material:

[0097] (1) Use ethanol, acetone, and isopropanol to ultrasonically dry the glass sheet, spin-coat a PEDOT:PSS layer at a speed of 3000 rpm as the anode modification layer (electron blocking layer), and then heat and dry at 150°C for 10 minutes. remove moisture;

[0098] (2) Use o-dichlorobenzene (ODCB) as a good solvent to prepare a mixed solution of P3HT / PCBB-CN-C8 (w / w 1 / 1.25), stir it, and then spin-coat it on the anode modification at a speed of 1000rpm layer; unannealed film was obtained;

[0099] (3) Take one piece of P3HT / PCBB-CN-C8 in the glove box and anneal at 100°C for 10 minutes. The resulting unannealed and annealed films can be used to test the transmission electron microscope, selected area electron diffraction pattern (see Figure 7...

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Abstract

The invention discloses a three-body fullerene derivative and its preparation method and application, which include a benzene-substituted methylene fullerene hydrophobic group, a benzene with an electron-withdrawing group connected through a flexible spacer group Vinyl cyanide, and a flexible functional group trisubstituted by benzene ring; does not form large-scale aggregation, and has excellent thermal stability. The active layer prepared by the fullerene derivatives of the present invention can not only form a long-range ordered fiber structure for the donor, but also effectively crystallize the acceptor, and finally obtain an ideal microstructure with nanoscale phase separation and double continuous transport channels; triplet The fullerene itself introduces an electron-withdrawing group, which improves the LUMO energy level and is beneficial to the improvement of the open circuit voltage of the device; the combination of the two advantages greatly improves the photoelectric conversion efficiency of the solar cell and simplifies the preparation of the device. At the same time, thermally stable active layer and device performance can be obtained, eliminating the risk of easy oxidation and degradation of the device in post-processing.

Description

technical field [0001] The invention belongs to the field of photovoltaic materials, and in particular relates to a triplet fullerene derivative with cooperative assembly performance, a preparation method thereof, and an application in solar cells. Background technique [0002] With the progress of society and the development of industry, people's demand for energy continues to increase, resulting in people's excessive exploitation and use of energy. Therefore, it is urgent to find a clean and renewable new energy source, and solar energy can satisfy people's needs. Therefore, how to effectively develop and utilize solar energy has become a hot spot of scientific research. Compared with inorganic solar cells, organic solar cells (OSCs) have many advantages: it requires a wide range of raw materials and low production costs; the preparation process is simple and can be realized by solution spin coating, inkjet printing and other cheap methods; at the same time It can form a ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/38C07C253/30H01L51/46
CPCY02E10/549
Inventor 李耀文赵越李永舫
Owner 苏州尚柔新能源有限公司
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