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A kind of conjugated polymer containing benzo[c]cinnoline and its synthesis method and application

A conjugated polymer, synthesis method technology, applied in the direction of compounds containing periodic table group 3/13 elements, tin organic compounds, compounds of periodic table group 4/14 elements, etc.

Active Publication Date: 2020-05-05
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, the application of benzo[c]cinnoline in OPVs has not been seen

Method used

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  • A kind of conjugated polymer containing benzo[c]cinnoline and its synthesis method and application
  • A kind of conjugated polymer containing benzo[c]cinnoline and its synthesis method and application
  • A kind of conjugated polymer containing benzo[c]cinnoline and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Synthesis of Conjugated Polymer (P1) Based on Benzo[c]cinnoline

[0059]

[0060] The preparation method of intermediate 1 (1,4-dibromo-2-fluoro-5-nitrobenzene) is carried out according to the above equation, and its specific operation is: add (5.0g, 19.70 mmol) 1,4-dibromo-2-fluorobenzene, a magnetic stirrer, 30 mL of dichloromethane (DCM), 8 mL of trifluoroacetic acid (TFA), and 16 mL of trifluoroacetic anhydride (TFAA), and stirred for 30 min under an ice bath. Ammonium nitrate (2.0 g, 25.0 mmol) was added as a solid powder in portions. After the addition was complete, the reaction was continued at room temperature for 24 h. The solution is poured into 100mL distilled water, then extracted with dichloromethane, the organic phases are combined, and the organic phase is dried with anhydrous magnesium sulfate. After filtering, the filtrate is spun to dryness to obtain the crude product. eluent) was subjected to column chromatography to obtain a white solid powder w...

Embodiment 2

[0067] Synthesis of Conjugated Polymer (P2) Based on Benzo[c]cinnoline

[0068]

[0069] Intermediate 3-C 8 C 10 The preparation method is carried out according to the above equation, and its specific operation is: sequentially add intermediate compound 2 (2g, 4.57mmol), 2-(tributyltin base)-4-(2-octyl Decyl)thiophene (6.86g, 10.5mmol), Pd(PPh 3 ) 4 (0.21g, 0.18mmol) and 100mL freshly distilled toluene, then in N 2 Under protection, the temperature was raised to 110°C for 30h. The reaction system was cooled to room temperature, then washed with CH 2 Cl 2 Extraction, the organic phase is washed with water and then dried with anhydrous magnesium sulfate, filtered, and the filtrate is spin-dried to obtain a crude product, and the crude product is subjected to column chromatography with petroleum ether / dichloromethane as an eluent to obtain a yellow solid that is Intermediate 3-C 8 C 10 , yield 80.1%. 1 H NMR (400MHz, CDCl 3 ,δ / ppm):8.55-8.53(d,J=6.89Hz,2H),7.43(s,2H...

Embodiment 3

[0074] Synthesis of Conjugated Polymer (P3) Based on Benzo[c]cinnoline

[0075]

[0076] The preparation method of the conjugated polymer P3 is carried out according to the above equation, and its specific operation is: take the monomer M1-C 8 C 10 and M2-D3 each 0.2mmol, it was dissolved in toluene (6mL), added tetrakis (triphenylphosphine) palladium (4.62mg0.004mmol) under the condition of nitrogen protection, then polymerized at the reflux temperature of toluene for 24h and stopped. The polymer solution was cooled to room temperature, and slowly precipitated into methanol (50 mL), and the precipitated solid polymer was sequentially extracted with methanol, n-hexane, acetone, dichloromethane, and chloroform in a Soxhlet extractor. Finally, the chloroform extract was added dropwise to methanol, filtered, and the obtained solid was vacuum-dried for one day to obtain a reddish-brown solid powder, which was polymer P3, with a yield of 69%, GPC: M n = 24.8 kDa, M w / M n = ...

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Abstract

The invention discloses a conjugated polymer containing benzo[c]cinnoline, its synthesis method and application. The structural formula of the conjugated polymer based on benzo[c]cinnoline mentioned in the present invention. The most common organic solar cell (OPVs) device (device structure is: ITO / PEDOT:PSS / Polymer:PC) prepared by the conjugated polymer based on benzo[c]cinnoline of the present invention 71 BM / LiF / Al), with its high open circuit voltage, wide and strong spectral response range, ideal fill factor, high short-circuit current density, and high energy conversion efficiency of 7.92%, fully demonstrated the potential and potential of this type of polymer in OPVs. Good application prospects.

Description

technical field [0001] The invention relates to the field of organic photovoltaic cell (OPVs) materials and structures, in particular to a conjugated polymer and its preparation method and application. Background technique [0002] With the rapid development of society, energy issues have become an increasingly important topic, especially clean energy represented by solar energy, wind energy, water energy, etc. is the focus of people's exploration and research. Organic photovoltaic cells (OPVs) are devices that convert solar energy into electricity using organic / polymer semiconductor materials as the photoactive layer. Compared with other types of solar cells, OPVs have the advantages of low cost, light weight, simple manufacturing process, large-scale printing and flexibility, and have shown great commercial application prospects. At present, the PCE of organic solar cells has exceeded 10%, but its photoelectric conversion efficiency is still far from the requirements of c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12C07D409/14C07F5/02C07F7/22H01L51/46
CPCC07D409/14C07F5/02C07F7/2208C08G61/126C08G2261/414C08G2261/411C08G2261/3223C08G2261/3241C08G2261/124H10K85/151Y02P20/10
Inventor 赵斌曾昭魁黄美华
Owner XIANGTAN UNIV
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