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Fluorine-containing phenanthrene quinoxaline and thiophene conjugated polymer

A technology of conjugated polymers and substituted quinoxalines, which is applied in the field of functional polymers, can solve problems such as large optical energy gaps that cannot effectively absorb sunlight, reduced conjugation of polymer molecules, and obstacles to the improvement of photoelectric conversion efficiency of devices. , to achieve the effect of improving photovoltaic performance and reducing optical energy gap

Inactive Publication Date: 2015-11-18
XIAN MODERN CHEM RES INST
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  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Fluorine-containing phenanthrene quinoxaline and thiophene conjugated polymer
  • Fluorine-containing phenanthrene quinoxaline and thiophene conjugated polymer
  • Fluorine-containing phenanthrene quinoxaline and thiophene conjugated polymer

Examples

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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, drop into methanol again for sedimentation, to obtain 175 mg of polymer A, which is a purple-black fibrous solid with a yield of 88%, a number average molecular weight of 1...

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 ThermalOriel...

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Abstract

The invention discloses a fluorine-containing phenanthrene quinoxaline and thiophene conjugated polymer, the energy gap and the HOMO energy level of the polymer are reduced simultaneously, and needs of polymer photovoltaic cell photoactivity layer electron donor materials is met. The conjugated polymer has the structural general formula shown in the description. The polymer disclosed by the invention has deeper HOMO energy level than a polymer D and can be as deep as -5.67 eV, and high open circuit voltage of more than 0.89 V can be obtained when the polymer is applied in photovoltaic cells.

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 Applications(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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