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Conjugated polymer of polyacenaphthylene and quinoxaline, as well as preparation method and application of conjugated polymer

A technology of conjugated polymers and quinoxaline, which is applied in semiconductor/solid-state device manufacturing, photovoltaic power generation, electrical components, etc., can solve the problems of unsatisfactory photovoltaic performance and low open circuit voltage of devices, so as to improve photovoltaic performance, Effects of increasing molecular weight and improving morphology

Inactive Publication Date: 2012-08-01
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Since 2009, Zhenan Bao's research group at Stanford University has reported a series of naphthylthiophene pyrazine polymers based on large plate structures and applied them to organic solar cells. Unfortunately, the photovoltaic properties of these materials are not Unsatisfactory, mainly due to the low open circuit voltage of the device (Voc=0.515~0.725 V) [H. A. Becerril, R. Mondal, Z. Bao, et al. J. Mater. Chem. 2009, 19, 591.; N. M. Mondal, H. Becerril, J. E. Norton, et al. Chem. Mater. 2009, 21, 3618.; Rajib Mondal, H.A.B., Eric Verploegen, Zhenan Bao, et al. al. J. Mater. Chem. 2010, 20, 5823]

Method used

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  • Conjugated polymer of polyacenaphthylene and quinoxaline, as well as preparation method and application of conjugated polymer
  • Conjugated polymer of polyacenaphthylene and quinoxaline, as well as preparation method and application of conjugated polymer
  • Conjugated polymer of polyacenaphthylene and quinoxaline, as well as preparation method and application of conjugated polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The preparation of embodiment 1 polymer PBDT-DTAQx

[0031] (1) Preparation of 5,8-bis(2-bromo-3-substituted thienyl)-5-acenaphthoquinoxaline monomer

[0032]

[0033] Referring to the synthesis method disclosed in Angewandte Chemie International Edition 2009, 48, 1664-1668, benzothiadiazole was prepared by reacting o-phenylenediamine with thionyl chloride as a starting material, and 4,7- Dibromobenzothiadiazole, then reduced by sodium borohydride to give 3,6-dibromo-o-phenylenediamine. Condensation of 3,6-dibromo-o-phenylenediamine and acenaphthoquinone to obtain 5,8-dibromoacenaphthoquinoxaline, and finally through Suzuki Coupling and bromination to obtain polymerized monomer 5,8-bis(2-bromo -3-dodecyl-5-thienyl)-acenaphthoquinoxaline.

[0034] The following takes the preparation of 5,8-bis(2-bromo-3-dodecyl-5-thienyl)-acenaphthoquinoxaline as an example to describe in detail, and the synthesis steps are as follows:

[0035] (1) Preparation of benzothiadiaz...

Embodiment 2

[0059] The preparation of embodiment 2 polymer PT-DTAQx

[0060]

[0061] 5,8-bis(2-bromo-3-dodecyl 5-thienyl)-acenaphthoquinoxaline (725 mg, 0.79 mmol), 2,5-bis(tributyltin)-thiophene (526 mg , 0.79 mmol), tetrakistriphenylphosphine palladium (45 mg) was added to the reaction flask, replaced with high-purity argon three times, and then injected with anhydrous and oxygen-free toluene, under the protection of argon, heated and refluxed for 72 h, the reaction After completion, the obtained polymer was settled in methanol, filtered with suction, and the collected polymer was subjected to Soxhlet extraction with acetone and n-hexane in turn for 24 h, and vacuum-dried at 40 °C for 24 h to obtain 0.42 g of a black solid, with a yield of 62%. . 1 H NMR (400 MHz, CDCl 3 , ppm) : 8.46 (br, 2H), 8.11 (br, 4H), 7.86~7.66 (br, 4H), 7.57~7.52 (br, 2H), 2.87~2.73 (br, 4H), 1.56~1.25 (br , 40H), 0.87 (br, 6H).

Embodiment 3

[0062] The preparation of embodiment 3 polymer PC-DTAQx

[0063]

[0064] Under argon protection, 5,8-bis(2-bromo-3-dodecyl 5-thienyl)-acenaphthoquinoxaline (343 mg, 0.38 mmol), N-(2-ethylhexyl )-3,6-carbazole dipinacol ester (200 mg, 0.38mmol), Pd(PPh 3 ) 4 (22 mg), 10 mL of toluene and 10 ml of 2 M potassium carbonate solution were added to a two-neck flask, heated to 90-95 °C under dark conditions, and stirred for 72 h. After the reaction, it was naturally cooled to room temperature, extracted with chloroform, washed with saturated brine, and dried overnight with anhydrous magnesium sulfate. Filter off the desiccant, spin off the solvent, settle with a large amount of methanol, and filter with suction. The collected polymer is subjected to Soxhlet extraction with acetone and n-hexane in turn for 24 h, and vacuum-dried at 40 °C for 24 h to obtain 0.22 g of a black solid. Yield 52%. 1 H NMR (400 MHz, CDCl 3, ppm): 8.36~8.33 (br,2H), 8.07~8.05 (br,4H), 7.96~7.70 (br,8...

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Abstract

The invention relates to novel conjugated polymer of polyacenaphthylene and quinoxaline, a preparation method of the conjugated polymer, as well as an application of the conjugated polymer in polymer solar cells. The conjugated polymer of polyacenaphthylene and quinoxaline, provided by the invention, has the structure formula as follows: Ar takes electron-rich aromatic ring as a structure unit; R1 is a linear chain or branch chain alkyl with the hydrogen atom number or carbon atom number of 1 to 20; and R2 is a linear chain or branch chain alkoxy with the hydrogen atom number or carbon atom number of 1 to 20.

Description

technical field [0001] The invention relates to an acenaphthoquinoxaline polymer and a preparation method, as well as the application of the conjugated polymer in polymer solar cells. Background technique [0002] In recent years, polymer solar cells have become a research hotspot in the field of clean and renewable energy research due to their cheapness, flexibility, and large area. Through the unremitting efforts of scientific researchers, in just ten years, along with the continuous development of new materials, its photoelectric conversion efficiency has increased from 10 -2 -10 -3 % increased to 9.2%[Service, R. F. Science 2011, 332, 293.], but to meet the practical needs, it is still necessary to further improve the photoelectric conversion efficiency, and the search for new conjugated polymer materials is the most important means to achieve this goal one. [0003] The conversion efficiency of solar cells is determined by the open circuit voltage of the device (V O...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/46
CPCY02E10/549
Inventor 黄艳邹勇张占元卢志云蒋青
Owner SICHUAN UNIV
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