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Pure heterogeneous fullerene bis-addition derivative and preparation method thereof

A fullerene and double-addition technology, which is applied in the field of fullerene double-addition derivatives and its preparation, can solve the problems of increasing trap state density, lack of regioselectivity, and reduced fullerene electron mobility. Achieve high Voc sum, good solubility and high energy conversion efficiency

Inactive Publication Date: 2016-09-28
合肥市激子能源技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

On the other hand, studies have also shown that due to the lack of regioselectivity in the double addition reaction, the obtained fullerene materials are a mixture of multiple isomers, and the trap states are increased due to the energy level difference between the isomers. Density, leading to a decrease in the electron mobility of fullerenes, which in turn affects the improvement of the short-circuit current and fill factor of the device

Method used

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  • Pure heterogeneous fullerene bis-addition derivative and preparation method thereof
  • Pure heterogeneous fullerene bis-addition derivative and preparation method thereof
  • Pure heterogeneous fullerene bis-addition derivative and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0065] Embodiment 1: Preparation of carbon sixty-two anthracene addition products

[0066] Mix 13.9mmol of C60 and 27.8mmol of anthracene solid powder in an agate mortar, then transfer to a 25mL round-bottom single-mouth bottle, equip the single-mouth bottle with a glass vacuum valve, vacuum the system for 5 minutes, and then evacuate it Put it in a muffle furnace and react at 240°C for 2 hours. After cooling, take out the round bottom bottle and open the vacuum valve to balance the air pressure inside and outside the bottle. Dig out the reacted solid with a spoon and wash it twice with carbon disulfide (200mL) to obtain C6 The decabisanthracene addition product, which contains unreacted C60 and C60bisanthracene addition product at a ratio of about 1:1, 12.6g, can be directly used as a raw material for the next step reaction.

[0067] 1 H NMR (CDCl 3 / CS 2 , 400MHz, δ / ppm): 7.81-7.83 (m, 8H, Ar), 7.49-7.51 (m, 8H, Ar), 6.07 (s, 4H, bridgehead CH).

Embodiment 2

[0068] Embodiment 2: the Bingel single addition product of preparation carbon sixty-two anthracene addition products

[0069] The synthesis process is as follows:

[0070]

[0071] 12.6 g of the C60 bis-anthracene addition product prepared in Example 1 were dispersed in carbon disulfide (1200 mL), and 56 mmol of di-tert-butyl bromomalonate and 56 mmol of DBU were added successively, and reacted at room temperature for 16 hours. After the end, the solid was filtered off, and the filtrate was directly washed with a gradient on a silica gel column. The developer was first selected carbon disulfide, and passed through the next brown color band. The developing agent is carbon disulfide: dichloromethane=3:1 (v / v), and the next brown-green color band passes through, and the Bingel mono-addition product (3.0 g) is obtained after the solvent is spin-dried. The molecular ion peak of product mass spectrum is 1291.2843, and (M+H + )match; 1 H NMR (CDCl 3 / CS 2 ,400MHz,δ / ppm):7.74-...

Embodiment 3

[0072] Embodiment 3: prepare the Bingel double addition product of carbon sixty-two anthracene addition product

[0073] The synthesis process is as follows:

[0074]

[0075] 2.3 mmol of the Bingel mono-addition product prepared in Example 2 were dispersed in o-dichlorobenzene (300 mL), and 6.9 mmol of di-tert-butyl bromomalonate and 6.9 mmol of potassium tert-butoxide were added successively, at room temperature Reacted for 15 minutes, quenched with water, and the organic phase was directly washed with a gradient of silica gel column. The developing agent was first selected carbon disulfide, followed by o-dichlorobenzene, and then the developing agent was selected carbon disulfide: dichloromethane=2:1 (v / v), The first brown color band is the unreacted raw material, and the second red color band is the Bingel double addition product, and 1.5 g is obtained after spin-drying the solvent. The molecular ion peak of product mass spectrum is 1505.4021, and (M+H + )match; 1 H ...

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Abstract

The invention discloses a pure heterogeneous fullerene bis-addition derivative and a preparation method thereof. The pure heterogeneous fullerene bis-addition derivative is of the structure shown in the formula (I), wherein A1 and A2 are selected from any one of groups shown in the description, and R1 and R2 independently represent a hydrogen atom, a halogen atom, alkenyl, alkynyl, alkyl of C1-C10, alkoxy of C1-C10, aryl, carbonyl or an ester group. The derivative has high LUMO energy level and high electronic mobility, and the energy conversion efficiency larger than 8% can be obtained when the pure heterogeneous fullerene bis-addition derivative is applied to a polymer solar cell.

Description

1. Technical field [0001] The invention relates to a fullerene double-addition derivative and a preparation method thereof, in particular to a pure isomeric fullerene double-addition derivative and a preparation method thereof, which can be used in organic solar cells. 2. Background technology [0002] In recent years, the frequent smog phenomenon in many places reflects the intensification of the contradiction between my country's energy demand and environmental protection. "Optimizing the energy structure and vigorously developing renewable energy" is an effective way to solve this contradiction. Solar energy is a clean, safe and renewable energy with great potential. Solar cells that use the photovoltaic effect to directly convert solar energy into electrical energy have always been the focus of the scientific community. The development of solar cells has gone through three generations in the past half a century, from the first generation of crystalline silicon cells, to ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C2/42C07C13/72C07C67/343C07C67/333C07C69/753C07C2/86C07C4/22C07C67/32H01L51/48H01L51/46
CPCC07C2/42C07C2/868C07C4/22C07C13/72C07C67/32C07C67/333C07C67/343C07C69/753C07B2200/11H10K71/12H10K85/215Y02E10/549Y02P20/10
Inventor 丁俊
Owner 合肥市激子能源技术有限公司
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