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A class of polymer materials and applications based on ester group side chain substituted quinoxaline derivatives
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A polymer material, quinoxaline technology, applied in the field of polymer solar cells, can solve the problem of few types, achieve strong electron-withdrawing ability, reduce HOMO energy level, and strong charge transfer effect
Active Publication Date: 2022-06-17
CHANGZHOU UNIV
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[0005] Aiming at the problem that there are few types of high-performance polymer donor materials at present, a new type of polymer photovoltaic donor material containing ester thiophene and ester benzene side chain substituted quinoxaline derivatives was invented
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Embodiment 1
[0045] Acceptor unit bis(2-butyloctyl)5,5'-(5,8-bis(5-bromothiophen-2-yl)-6,7-difluoroquinoxaline-2,3-diyl ) bis(thiophene-2-carboxylate) (DFQxTA) and bis(2-butyloctyl)4,4'-(5,8-bis(5-bromothiophen-2-yl)-6,7- Synthesis of difluoroquinoxaline-2,3-diyl)dibenzoate (DFQxBA). The synthetic routes of DFQxTA and DFQxBA are as follows:
[0046]
[0047] 1.1. Synthesis of 5-bromothiophene-2-carboxylic acid 2-ethylhexyl ester (SM1)
[0048] In a 250mL there-necked flask, add 5-bromo-2-carboxythiophene (8.28g, 40mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (8.43g, 44mmol) successively ), 4-dimethylaminopyridine (1.46g, 12mmol), 2-butyl-1-n-octanol (8.18g, 44mmol) and anhydrous 120mL of dichloromethane, react under nitrogen protection and room temperature conditions 48h. The reaction was stopped, the reaction solution was poured into 120 mL of water, extracted three times with dichloromethane (3×25 mL), dried over anhydrousmagnesiumsulfate, filtered, and the...
[0070] In a 10mL single-neck flask, add (DFQxTA) (159.75mg, 0.15mmol), 4,8-bis(5-(ethylhexylthio)thienyl)benzo[1,2-b:4,5- b'] Dithienyl) bis(trimethyltin) (BDTTSn) (159.7mg, 0.15mmol), tetrakis(triphenylphosphine)palladium (6mg), HPLC toluene 6mL, evacuated oxygen by liquid nitrogen freezing, each Thaw after the first freeze extraction, repeat three times, put the reaction into a 110°C constant temperature pot, and observe the reaction change at all times. After the reaction stopped, the reaction solution was diluted with chlorobenzene, settled in methanol, suction filtered, and the crude product was washed with Soxhlet extraction (methanol-acetone-n-hexane-dichloromethane-trichloromethane), and after concentrating the collected solution of chloroform , purified by flash column chromatography, concentrated, precipitated with methanol, suction filtered, and dried in vacuo to obtain a black solid product (195.7 mg, yield 8...
Embodiment 3
[0071] Example 3 Synthesis of polymer PBDTTS-DFQxBA
[0072]
[0073] The synthesis and purification steps of polymer PBDTTS-DFQxBA are the same as those of polymer PBDTTS-DFQxTA. A black solid product was finally obtained (188.1 mg, 80.3% yield).
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Abstract
The invention belongs to the field of organic photovoltaic solar cells, and specifically relates to a class of polymer materials based on ester side chain substitution of quinoxaline derivatives and their applications. This kind of quinoxaline derivatives substituted with ester group side chains has a simple synthetic route, high yield and good stability; the introduction of ester group side chains can effectively increase the solubility of materials, reduce the energy level of the highest occupied molecular orbital, and broaden the absorption , Ensure that the active layer has a good phase separation, and at the same time achieve the effect of increasing the open circuit voltage, short circuit current and fill factor of the polymersolar cell. The polymer material is used as the electron donor, Y6 is used as the electronacceptor, and it is applied to the solution-processed polymer solar cell, and its energy conversion efficiency reaches 15.80%. The present invention confirms that the ester group side chainquinoxaline derivative polymer can effectively improve the photovoltaic performance of polymer solar cells, and realizes the use of side chain ester group substituted quinoxaline derivative polymer materials in polymer solar cells efficient energy conversion.
Description
technical field [0001] The invention belongs to the field of polymer solar cells (PSCs), in particular to a class of polymer materials and applications based on ester side chain substituted quinoxaline derivatives. Grafting ester thiophene or ester benzene side chain on the conjugated side chain of quinoxaline, and polymerizing it as acceptor unit with benzodithiophene derivatives to obtain D-A type conjugated polymer materials; and using such materials Preparation of photoactive layers with non-fullerenesmall moleculeacceptor materials for the study of polymer solar cell devices. Background technique [0002] Since the Industrial Revolution, the use of fossil energy has made great progress in human society, but it has also brought about problems such as environmental pollution and energy crisis. As an "inexhaustible and inexhaustible" clean energy, solar energy has become an important choice for new energy sources. Organic solar cells (OSCs) have unique advantages such ...
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