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Triad fullerene derivative and preparation method and application thereof

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

Active Publication Date: 2015-09-16
SUZHOU UNIV
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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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  • Triad fullerene derivative and preparation method and application thereof
  • Triad fullerene derivative and preparation method and application thereof
  • Triad fullerene derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] A method for preparing a triplet fullerene derivative with cooperative assembly performance, specifically comprising the following steps:

[0069] (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;

[0070] (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;

[0071] (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 hour...

Embodiment 2

[0084] 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.

[0085] 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:

[0086]

[0087] Include the following steps:

[0088] (1) Phosphorus tribromide (0.38 g, 1.48 mmol) in CH 2 Cl 2 (2 mL) solution was added to ...

Embodiment 3

[0095] 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:

[0096] (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;

[0097] (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;

[0098] (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 triad fullerene derivative and a preparation method and application thereof. The triad fullerene derivative comprises a benzene-substituted methylene fullerene hydrophobic group, a phenylethylene nitrile bonded by a flexible spacer group and having an electrondrawing group and a flexible functional group with a benzene ring trisubstituted. The triad fullerene derivative does not form large-scale aggregation and moreover has excellent heat stability. With adoption of an active layer made from the fullerene derivative, a donator can form a long-course ordered fiber structure, an acceptor can also crystalize effectively, and thus an ideal microstructure having nano-scale phase separation and bicontinuous transportation channels can be obtained finally; due to introduction of the electrondrawing group to the triad fullerene derivative, the LUMO energy level is improved, which is beneficial to improvement of open-circuit voltage of a device; due to integration of the two advantages, the photoelectric converting rate of a solar cell can be improved to a great extent and the preparation process of a device is simplified; moreover, heat-stable active layer and device properties can be achieved and the risk that the device is prone to oxidation and decomposition in post-treatment can be eliminated.

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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IPC IPC(8): C07C255/38C07C253/30H01L51/46
CPCY02E10/549
Inventor 李耀文赵越李永舫
Owner SUZHOU UNIV
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