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Synthesis of asymmetric non-fullerene receptor and printing preparation of solar battery with asymmetric non-fullerene receptor

A non-fullerene, asymmetric technology, applied in semiconductor/solid-state device manufacturing, circuits, photovoltaic power generation, etc., can solve the problems of cumbersome preparation process, insoluble in organic solvents, high cost, etc., and achieve simple and satisfactory preparation process Energy conversion efficiency and low cost effect

Active Publication Date: 2019-08-30
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Among the preparation materials of organic solar cells in the prior art, the solubility is poor and cannot be dissolved in most organic solvents; and the complementary performance of absorption spectrum is poor
And the prior art preparation process is loaded down with trivial details, and cost is high

Method used

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  • Synthesis of asymmetric non-fullerene receptor and printing preparation of solar battery with asymmetric non-fullerene receptor
  • Synthesis of asymmetric non-fullerene receptor and printing preparation of solar battery with asymmetric non-fullerene receptor
  • Synthesis of asymmetric non-fullerene receptor and printing preparation of solar battery with asymmetric non-fullerene receptor

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] An organic small molecule receptor whose chemical structure is RPC provided in the embodiment of the present invention, its synthesis route is as follows:

[0056]

[0057] Compound 1 can be synthesized according to the steps reported in the literature (European journal of organic chemistry, 2006, 2006(17): 4014-4020; Advanced materials, 2014, 26(30): 5137-5142).

[0058] Synthesis of Compound 2: Add Compound 1 (164mg, 0.43mmol), PDI-Br (381mg, 0.46mmol) into a 100mL two-necked flask, and inject 10mL of freshly distilled tetrahydrofuran and 5mL of saturated potassium carbonate into the reaction flask under the protection of argon. The aqueous solution was bubbled for 20 minutes, tetrakis(triphenylphosphine)palladium (25mg, 0.0094mmol) was added, and stirred at 70°C for 12 hours. After being cooled to room temperature, the reaction solution was poured into a one-necked bottle, and the tetrahydrofuran was spinned out under reduced pressure, extracted three times with d...

Embodiment 2

[0063] An organic small molecule receptor with a chemical structure of FRPC provided in the embodiment of the present invention has a synthetic route as follows:

[0064]

[0065] Synthesis of compound 3: In a 100mL two-necked flask, add compound 2 (300mg, 0.30mmol), iodine simple substance (38mg, 0.30mmol), and add 50mL toluene, irradiate the reaction flask with a 400W ultraviolet curing lamp, and raise the temperature to 115 The toluene was refluxed and stirred at ℃, and the end point of the reaction was monitored by TLC thin film chromatography. The reaction was terminated when compound 2 was completely reacted. After returning to room temperature, spin out the toluene under reduced pressure, and directly use column chromatography for purification. The developer is petroleum ether:dichloromethane (v:v=1:3) to obtain a red solid (244mg, 81%) .

[0066] 1 H NMR (400MHz, Chloroform-d) δ10.72 (d, J = 14.96Hz, 1H), 10.06 (s, 2H), 9.27–8.91 (m, 5H), 8.3–8.04 (m, 2H), 7.75 (...

Embodiment 3

[0070] The embodiment of the present invention provides an organic small molecule receptor whose chemical structure is IPC, and its synthesis route is as follows:

[0071]

[0072] Chemical formula is the synthesis of the small molecule acceptor of IPC: in 100mL two-necked flask, add compound 2 (60mg, 0.060mmol), 2-(3-ethyl-4-oxothiazolidine-2-ylidene) malononitrile ( 29mg, 0.18mmol), 10mL chloroform, and 1 drop of piperidine, the temperature was raised to 70°C under reflux and stirred, and the end of the reaction was monitored by TLC thin film chromatography. The reaction was terminated when all reactants 2 had reacted. After returning to room temperature, it was extracted several times with dichloromethane, dried over anhydrous sodium sulfate, filtered, and the crude product was purified by column using petroleum ether:dichloromethane (v:v=1:3) as developing solvent, and then The product was developed and purified on a TLC plate, and recrystallized with dichloromethane / m...

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Abstract

The invention belongs to the technical field of photovoltaic materials and discloses synthesis of a perylene diimide asymmetric micromolecule non-fullerene receptor and a method for printing and preparing an organic solar battery. The perylene diimide asymmetric micromolecule non-fullerene receptor is a broad-bond gap Al-D-A2 type asymmetric non-fullerene micromolecule receptor based on a bridgedunit carbazole core, and has a structural formula I as shown in the specification. The asymmetric micromolecule receptor material which is provided by the invention and is used for printing and preparing the organic solar battery has good solution processing performance and electron transmission performance, and in addition has good absorption complementation and energy matching after being combined with narrow-bond gap polymer donor materials such as PTB7-Th; the receptor can be applied to an open circuit voltage which is 0.95V at most, and energy conversion efficiency which is about 2.01-3.27%, and the broad-bond gap asymmetric non-fullerene micromolecule receptor provided by the invention has wide application prospects in the field of organic photovoltaic.

Description

technical field [0001] The invention belongs to the technical field of photovoltaic materials, and relates to a synthesis and preparation method of a perylene diimide asymmetric small-molecule non-fullerene acceptor, in particular to an A with a bridging unit carbazole as the core. 1 -D-A 2 Type asymmetric small molecule acceptor and its preparation method and application in organic solar cells. Background technique [0002] Solar energy is the largest energy source known to mankind at present. It has the characteristics of inexhaustible, inexhaustible, wide distribution, clean, and pollution-free. It is an ideal renewable energy source. As a device that can directly convert solar energy into electrical energy, solar cells have received extensive attention and research. Among them, organic solar cells, as an important part of solar energy in mobile applications, have become the focus of scientific research because of their light weight, flexibility, translucency, and roll-...

Claims

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Application Information

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IPC IPC(8): C07D471/06C07D471/16H01L51/42H01L51/46
CPCC07D471/06C07D471/16H10K85/656H10K85/6572H10K30/00Y02E10/549
Inventor 王行柱陈煜卓闫磊黄茁豪刘志鑫刘帅虎谢柳平
Owner XIANGTAN UNIV
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