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Two-dimensional difuronaphthalene compound and difuronaphthalene conjugated organic micro-molecular compound, and preparation methods and applications thereof
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A technology of small molecular compounds and difuran, applied in chemical instruments and methods, organic chemistry, tin organic compounds, etc., to achieve the effects of structure determination, absorption spectrum bandwidth, and improvement of solubility
Inactive Publication Date: 2017-07-11
CENT SOUTH UNIV
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[0003] So far, no naphthodifuran-based conjugated organic small molecules have been used in the field of solar cells
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Embodiment 1
[0048] Synthetic Method of Small Organic Molecule NDFP-CNCOO
[0049] a) 4,9-dibromonaphthyl[1,2-b:5,6-b']difuran (0.62g, 1.69mmol), tributyl (4-((2-ethylhexyl)oxy Base) phenyl) tin (2.51g, 5.07mmol) was dissolved in dry toluene 20mL, and bistriphenylphosphine palladium dichloride (0.24g, 0.34mmol) was added to the reaction system under the protection of argon, and the temperature was raised to 100 °C for 24 hours. The reaction was stopped, cooled to room temperature, the mixture was poured into water, and extracted with dichloromethane. After spin-drying the solvent with a rotary evaporator, use petroleumether:dichloromethane (4:1 volume ratio) to pass through a silica gel column, spin-dry the solvent, and then vacuum-dry to obtain a white solid 1 (0.62g, yield: 61.3%), and synthesize compound 1 The representation of is as follows:
[0059] Using NDFP-CNCOO as the donor material, fullerene PC 71 BM is used as the acceptor material, combined with annealing process to prepare solar cell devices, the device structure is: ITO / PEDOT:PSS / NDFP-CNCOO:PC 71 BM / PDINO / Al. The test conversion efficiency data of organic small molecule solar cell devices are shown in Table 1, and the J-V curve is shown in figure 1 . Based on the preliminary test of this device, the photoelectric conversion efficiency is 3.13%. After thermal annealing at 110°C, the short-circuit current, open-circuit voltage, and fill factor are all improved, and the conversion efficiency reaches 4.6%.
[0060] Table 1 Photovoltaic performance of organic solar cells prepared with NDFP-CNCOO as donor material
[0061]
[0062] Optical Analysis of Small Molecules:
[0063] The absorption spectrum measured by the UV-visible absorption spectrometer is as follows:...
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Abstract
The invention discloses a two-dimensional difuronaphthalene compound and a difuronaphthalene conjugated organic micro-molecular compound, and preparation methods and applications thereof. The difuronaphthalene conjugated organic micro-molecular compound comprises a large rigid planar conjugated system, also comprises furan, thiophene, a cyano group, an ester group and other polar groups, has the advantages of good solubility, easiness in processing, broad spectral absorption and good stability, and can be used as a donor material to produce organic photovoltaic devices with good photovoltaic performances, and the photoelectric conversion efficiency of the single-layer devices reaches 4.6%. The preparation method of the difuronaphthalene conjugated micro-molecular compound has the advantages of simplicity, easily controlled conditions, easiness in purification and separation, and facilitation of enlarged production and application.
Description
technical field [0001] The invention relates to an organic small molecule photovoltaic material, in particular to a two-dimensional naphthodifuran monomer and an A-π-D-π-A type conjugated organic compound with naphthodifuran as a donor unit. Small molecules, and their preparation methods and applications belong to the technical field of organic small molecule solar cells. Background technique [0002] Designing and synthesizing ideal small molecule donor materials is one of the most effective methods to improve the photovoltaic performance of small molecule solar cells. As an electron donor unit, benzodifuran (BDF) has been widely used in small organic molecules and donor-acceptorpolymer organic solar cells. In 2015, Huo et al. reported a polymer with benzodifuran as the electron donor unit, and its photoelectric conversion efficiency reached 9.43%, which is the highest efficiency of benzodifuran-based photovoltaic materials. Compared with benzodifuran, naphthodifuran (ND...
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