Conjugated polymers of fluorine-containing phenanthrenequinoxaline and thiophene

A technology of conjugated polymer and substituted quinoxaline, applied in the field of functional polymers, can solve the problems of reduced degree of conjugation of polymer molecules, large optical energy gap that cannot effectively absorb sunlight, and hindering the improvement of photoelectric conversion efficiency of devices. , to reduce the optical energy gap and improve the photovoltaic performance.

Inactive Publication Date: 2017-10-03
XIAN MODERN CHEM RES INST
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Problems solved by technology

[0005] Although the above materials have achieved good photoelectric conversion results, due to the quinoxaline units contained in the molecular structure of this type of polymer, the 2 and 3 positions are all substituted by phenyl, and the resulting steric hindrance makes the two phenyl The ring and the main chain structure of the quinoxaline molecule form a certain twist, and cannot coexist in the same plane, resulting in a decrease in the degree of conjugation of the polymer molecule, a large optical energy gap that cannot effectively absorb sunlight, and more photons are generated for photoelectric conversion, which is manifested in the device The short-circuit current of the Zhongwei battery is too small, which has become an important bottleneck hindering the improvement of the photoelectric conversion efficiency of the device

Method used

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  • Conjugated polymers of fluorine-containing phenanthrenequinoxaline and thiophene
  • Conjugated polymers of fluorine-containing phenanthrenequinoxaline and thiophene
  • Conjugated polymers of fluorine-containing phenanthrenequinoxaline and thiophene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1: the synthesis of intermediate

[0038] (1) Preparation of 4-fluoro-3,6-dibromo-1,2-phenylenediamine (compound 1)

[0039] 5-Fluoro-4,7-dibromo-2,1,3-benzothiadiazole (5g, 0.016mol) was dissolved in 150ml of absolute ethanol, and NaBH4 (11.1g, 0.29mol) was added in portions at 0°C , and then reacted at room temperature for 20h. After the reaction, ethanol was removed by vacuum distillation, 160ml of water was added, extracted with ethyl acetate, the organic phase was washed with saturated brine, and finally dried with anhydrous MgSO4. Concentrate to remove the organic solvent, and the obtained crude product is chromatographed on a silica gel column with n-hexane / ethyl acetate (25:1 by volume) to obtain 3.5 g of 4-fluoro-3,6-dibromo-1,2-phenylenediamine , yield 78%.

[0040] (2) Preparation of 1,2-bis(3-octyloxyphenyl)ethanedione (compound 2)

[0041] Add LiBr (5.25g, 60.4mmol) to the THF solution (40ml) of CuBr (4.33g, 30.2mmol), stir and dissolve at ro...

Embodiment 2

[0047] Example 2: Polymer A

[0048]

[0049] The reaction was carried out under the protection of nitrogen, 11-fluoro-10,13-dibromo-2,7-dioctyloxybenzodiazepine (213.7mg, 0.3mmol) and 2,5-bis(trimethyltin) Thiophene (198.6mg, 0.3mmol) was dissolved in 10ml of toluene, nitrogen gas was passed for 0.5h, catalyst tris(dibenzylideneacetone)dipalladium (5.5mg) and ligand tri-o-cresylphosphine (9.8mg) were added, and continued After aeration for 0.5h, heating was started, and the reaction was refluxed for 24h. The system was naturally cooled at room temperature, added dropwise to methanol to settle, filtered, and the collected polymer was dried in a vacuum oven at 50°C for 12h. The obtained polymer was sequentially washed with methanol, n-hexane, Chloroform Soxhlet extraction, concentrated chloroform extract, again dropped into methanol for sedimentation, to obtain 175 mg of polymer A as a purple-black fibrous solid with a yield of 88%, a number average molecular weight of 192.3...

Embodiment 3

[0052] Example 3: Polymer B

[0053]

[0054] Same as in Example 2, changing the deficient unit to 11-fluoro-10,13-dibromo-3,6-dioctyloxybenzodiazepine, using exactly the same polymerization method to obtain polymer B with a yield of 76 %, the number average molecular weight is 153.67kDa, and the distribution coefficient is 2.75.

[0055] Electrochemical test: use CHI660D electrochemical workstation, use glassy carbon electrode as working electrode, platinum wire electrode as counter electrode, Ag / Ag+ electrode as reference electrode, Bu4N·PF6 as electrolyte, in acetonitrile solvent, through cyclic voltammetry The HOMO energy of the polymer B thin film was determined to be -5.58eV.

[0056] Photovoltaic performance research: Using the sandwich cell structure of ITO / PEDOT:PSS / polymer:PC71BM / LiF / Al, the polymer B and the acceptor material PC71BM are made into a photovoltaic cell according to a certain weight ratio, with an effective area of ​​0.16cm2, in Newport Thermal Ori...

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Abstract

The invention discloses a conjugated polymer of fluorine-containing phenanthroquinoxaline and thiophene, which simultaneously reduces the energy gap and HOMO energy level of the polymer, and meets the requirement of electron donor materials for photoactive layers of polymer photovoltaic cells. The general structural formula of the present invention is as follows: the polymer disclosed in the present invention has a deeper HOMO energy level than polymer D, which can be as deep as -5.67eV, and can be used in photovoltaic cells to obtain a high open circuit voltage of >0.89V.

Description

technical field [0001] The invention belongs to the field of functional polymers, in particular to a conjugated polymer of fluorine-containing phenanthroquinoxaline and thiophene. Background technique [0002] Polymer photovoltaic cells are photovoltaic devices that convert solar energy into electrical energy. Due to their low cost, simple manufacturing process, light weight and easy portability, they are favored by researchers. How to improve the photoelectric conversion efficiency of the battery so that it can be commercially produced is a key technical problem that needs to be solved urgently in this field. The active layer composed of donor and acceptor materials is the core part of the device. In view of the fact that the current acceptor material is mostly selected as fullerene derivatives (PCBM), the development of high-efficiency polymer donor materials is very important for improving the photoelectric conversion of batteries. Efficiency matters. [0003] As the ma...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12
Inventor 高潮武海梅边庆真赵宝锋王维平安忠维
Owner XIAN MODERN CHEM RES INST
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