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Thieno (2, 3-f) benzofuran compound, polymers thereof and application of polymers

A technology of benzofuran and 3-f, which is applied in the field of organic optoelectronic material synthesis, can solve problems such as few reports, achieve great commercial prospects, good thermal stability, and improve solubility

Inactive Publication Date: 2014-07-23
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Benzo[1,2-b; 3,4-b]difuran (BDF) is an important electron-donor unit, but its application as a donor unit in organic electronics after polymerization with other fused heterocyclic acceptor units There are not many reports in the field

Method used

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  • Thieno (2, 3-f) benzofuran compound, polymers thereof and application of polymers
  • Thieno (2, 3-f) benzofuran compound, polymers thereof and application of polymers
  • Thieno (2, 3-f) benzofuran compound, polymers thereof and application of polymers

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] a) Thionyl chloride (65.3mL, 0.9mol) was added dropwise into a 500ml dry round-bottomed flask of furan-3-carboxylic acid (25.1g, 0.224mol), stirred and refluxed for 4 hours, then cooled to room temperature Finally, the solvent was spin-dried to obtain compound 1 as a colorless oil, which was used in the next step without further purification.

[0052] b) Compound 1 (29.24g, 224mmol) was added dropwise to a solution of diethylamine (92.6mL) in dichloromethane (100mL) at 0°C, and then the reaction mixture was warmed to room temperature and stirred for 1 hour. After cooling to room temperature, the mixture was poured into ice water, extracted with dichloromethane, the organic phase was washed twice with water, dried over anhydrous magnesium sulfate, and the solvent was spin-dried, and the crude product was passed through a silica gel column (eluted with ethyl acetate / petroleum ether (2:1 , V / V) is the eluent) to obtain compound 2 (7.5 g, 85%) as an orange-red oil. 1 H NMR...

Embodiment 2

[0058] The synthesis method of thieno[2,3-f]benzofuran compound is as in Example 1.

[0059] Polymer (PTBFDTBTz) was prepared by Stille reaction: under nitrogen protection, M1 (0.134g, 0.151mmol) and N-octyl-4,7-dithienyl-benzotriazole dibromide (0.0838g, 0.151g) Add to 10mL of anhydrous toluene and 2ml of DMF, then add Pd(PPh 3 ) 4 (10mg), stirred and reacted at 110°C for 24 hours, cooled to room temperature, poured into 100mL methanol for precipitation, filtered, extracted with methanol, n-hexane, and chloroform sequentially in a Soxhlet extractor, recovered the chloroform solution, and spin-dried Add a small amount of chloroform to dissolve the excess solvent, pour it into a centrifuge tube, add methanol to make it chromatographically, pour off the upper clear night after high-speed centrifugation, and repeat several times to obtain the target polymer PTBFDTBTz (91mg, 62%). m n = 2.8 kDa; M w = 21.88 kDa; PDI = 7.8. Anal. Calcd for (C 58 h 69 N 3 OS 5 )n (%): C, 70...

Embodiment 3

[0061] The synthesis method of thieno[2,3-f]benzofuran polymer is as in Example 1.

[0062] Polymer (PTBFDTBO) was prepared by Stille reaction: under nitrogen protection, M1 (0.1359g, 0.153mmol) and 5,6-dioctyloxy-4,7-dithienyl-benzoxadiazole dibromide (0.1068 g, 0.153mmol) was added to 10mL of anhydrous toluene and 2 ml of DMF, and then Pd (PPh 3 ) 4 (10mg), stirred and reacted at 110°C for 24 hours, cooled to room temperature, poured into 100mL methanol for precipitation, filtered, extracted with methanol, n-hexane, and chloroform sequentially in a Soxhlet extractor, recovered the chloroform solution, and spin-dried Add a small amount of chloroform to dissolve the excess solvent and pour it into a centrifuge tube, add methanol to make it chromatographically come out, pour off the upper layer after high-speed centrifugation, and repeat several times to obtain the target polymer PTBFDTBO (89mg, yield 52%) . m n = 524.1 kDa; M w = 1011.5 kDa; PDI = 1.9. Anal. Calcd for (C...

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Abstract

The invention discloses a thieno (2, 3-f) benzofuran compound, polymers thereof and an application of the polymers. A series of polymers with thieno (2, 3-f) benzofuran compound unit structures are synthesized from the thieno (2, 3-f) benzofuran compound, benzothiadiazole, benzotriazole, benzoxadiazole and other monomers through a Stille coupling polymerization method. The polymers have good thermal stability and electrochemical performance and can be mixed with commonly used fullerene and organic acceptor substances to prepare polymer solar cells with high photoelectric conversion rate, the photoelectric conversion efficiency of single-layer polymer solar cell devices can be as high as 6.4%, and the polymer materials have huge commercial prospects in application of the solar cells.

Description

technical field [0001] The invention relates to a thieno[2,3-f]benzofuran compound and its polymer and the application of the polymer, and belongs to the field of organic photoelectric material synthesis. Background technique [0002] In recent years, conjugated polymers containing benzo[1,2-b; 3,4-b]dithiophene (BDT) groups as donors have shown excellent photovoltaic performance. Yang Yang, Wu Hongbin, Hou Jianhui and others synthesized a series of conjugated polymers based on BDT. These polymers have very good photoelectric properties. The highest power conversion efficiency (PCE) of the reported tandem device solar cell is 10.6%, but based on The stability of BDT material is slightly lacking, and there are many layers of stacked devices, and the process is relatively complicated. [(1) Z.He, C.Zhong, S.Su, M.Xu, H.Wu, Y.Cao, Nature Photonics2012, 6, 591; (2) L.Dou, J.You, J.Yang, C. -C. Chen, Y. He, S. Murase, T. Moriarty, K. Emery, G. Li, Y. Yang, Nature Photonics 2012,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04C08G61/12H01L51/46
CPCC07D495/04C08G61/123C08G61/125C08G61/126C08G2261/3246C08G2261/3245C08G2261/3242C08G2261/3241C08G2261/3243C08G2261/91H10K85/113Y02E10/549Y02P70/50
Inventor 邹应萍樊令郭秀萍崔锐利蒋历辉江文辉
Owner CENT SOUTH UNIV
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