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A conjugated polymer, fluoroquinoxaline technology, applied in photovoltaic power generation, electrical components, circuits, etc.
Inactive Publication Date: 2014-12-10
XIAN MODERN CHEM RES INST
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[0005] In view of the above-mentioned influence of fluorine atoms on material properties, the introduction of fluorine atoms into the electron-deficient unit of quinoxaline to prepare a new type of fluorine-containing D-A-D type donor polymer is expected to further reduce the HOMO energy and increase the open circuit voltage, thereby improving the photovoltaic performance of the device. performance, but so far there are no reports about the structure, preparation method and application of such materials in photovoltaic cells
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Embodiment 1
[0034] Example 1: Synthesis of acceptor unit 6-fluoro-5,8-bis(5-bromo-4-hexylthiophene)-2,3-bis(3-octyloxyphenyl)quinoxaline
[0035] The synthetic route is as follows:
[0036]
[0037] (1) Synthesis of 4-fluoro-3,6-dibromo-phenylenediamine (compound 1)
[0038] 5-Fluoro-4,7-dibromo-2,1,3-benzothiadiazole (5g, 16mmol) was dissolved in absolute ethanol (150ml), and NaBH was added in batches at 0°C 4 (11.1 g, 290 mol), then react at room temperature for 20 h. After the reaction was finished, concentrate to remove ethanol, add 160ml of water, extract with ethyl acetate, wash the organic phase with saturated brine, anhydrous MgSO 4 Dry and concentrate to obtain the crude product, which is purified by n-hexane / ethyl acetate (25:1, v / v) silica gel column to obtain 3.5 g of product (compound 1) with a yield of 78%.
[0039] (2) Synthesis of 1,2-bis(3-octyloxyphenyl)ethanedione (compound 2)
[0040] Add LiBr (5.25g, 60.4mmol) to a solution of cuprous bromide (4.33g, 30.2mmol) ...
Embodiment 2
[0049] Example 2: Synthesis of the donor unit 9-octyl-2,7-carbazole boronate
[0050] The synthetic route is as follows:
[0051]
[0052] (1) Synthesis of 9-octyl-2,7-dibromocarbazole (compound 6)
[0053] 2,7-dibromocarbazole (12.4g, 38.2mmol) and 300ml DMSO were added to a four-necked reaction flask with a thermometer and a dropping funnel, and N 2 , add tetrabutylammonium bromide (1.3g) successively under stirring at room temperature, 50% potassium tert-butoxide solution (prepared by 17.2g potassium tert-butoxide and 17.2ml water), then add bromooctane dropwise ( 7.4g, 38.3mmol), react at room temperature for 5h after addition. Add 200mL of water, filter, wash with water until neutral, dry, recrystallize from ethanol, and dry to obtain 13.5g of white needle-like solid (Compound 6), with a yield of 66.5%.
[0054] (2) Synthesis of 9-octyl-2,7-carbazole boronic acid (compound 7)
[0055] Add compound 6 (7.9g, 14.9mmol) and 150ml THF into a 250mL reaction flask, cool t...
Embodiment 3
[0060] Example 3: Polymer A
[0061]
[0062] The reaction was carried out under the protection of nitrogen, the acceptor unit compound 5 (209.4mg, 0.2mmol) obtained in Example 1, the donor unit compound 8 (106.2mg, 0.2mmol) obtained in Example 2, tetraethyl hydroxide Ammonium (20%, 1.5ml) and toluene (15ml) were added to a dry two-necked flask, ventilated for 0.5h, and the catalyst tris(dibenzylideneacetone)dipalladium (3.7mg) and the ligand tri-o-cresylphosphine were added (6.5mg), continue to ventilate for 0.5h, then start heating, after reflux reaction for 60h, add 2.2ul bromobenzene, add 2.4mg phenylboronic acid after 1h, continue to react for 12h, stop the reaction, cool the system to room temperature, and dissolve the reaction solution with methanol Settling and filtering to obtain a polymer, drying in a vacuum oven at 50°C for 12 hours, sequentially performing Soxhlet extraction with methanol, n-hexane, and chloroform, concentrating the chloroform extract, settling ...
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Abstract
The invention belongs to the field of organic polymer functional materials, and discloses a 9-octylcarbazole-fluoroquinoxaline derivative conjugated polymer of which the chemical general formula is disclosed as the following formula. The conjugated polymer is prepared by carrying out Sizuki coupling reaction by using 9-octyl-2,7-carbazole as an electron supply unit and fluoroquinoxaline as an electron-deficient unit. The conjugated polymer can be used for as a donor material for bulk heterojunction solar cells. Since the strong electron withdrawing group fluorine atom is introduced onto the electron-deficient unit quinoxaline, the polymer can effectively lower the HOMO energy level of the material, thereby enhancing the open-circuit voltage of the polymer photovoltaic cell. The circulating volt-ampere measurement proves that compared with the non-fluoroquinoxaline-9-octylcarbazole polymer, the HOMO energy level of the mono-fluoro-polymer is 0.02-0.1eV lower, and the HOMO energy level of the di-fluoro-polymer is 0.05-0.2eV lower. The fluoro material and PCBM can be blended and applied to the photoactive layer of the bulk heterojunction polymer solar cell, and the open-circuit voltage of the device is 0.6-1.0V.
Description
technical field [0001] The invention belongs to the field of functional polymer materials, and in particular relates to a conjugated polymer of 9-octylcarbazole and fluoroquinoxaline derivatives. Background technique [0002] Polymer solar cells have become a research hotspot at home and abroad in recent years due to their outstanding advantages such as simple preparation process, low cost, light weight and flexible devices. The current research focus on polymer solar cells is to develop efficient conjugated polymers to give Bulk and acceptor materials to improve their photoelectric energy conversion efficiency. For polymer materials acting as electron donors, the absorption spectrum of the material determines the short-circuit current of the device, the HOMO energy level of the material determines the open-circuit voltage of the device, and the structure and carrier mobility of the material determine the fill factor of the device. . In order to obtain a donor polymer mate...
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