Organic-inorganic hybrid photoelectric conversion element
A technology for organic photoelectric conversion and photoelectric conversion elements, which can be used in electrical components, organic semiconductor devices, photovoltaic power generation, etc., and can solve problems such as cost and productivity.
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[0097] Hereinafter, examples are shown in order to describe the present invention in more detail, but the present invention is not limited to these examples.
[0098] In the following examples, as the molecular weight of the polymer, the number average molecular weight in terms of polystyrene was determined using GPC (PL-GPC2000) manufactured by GPC Laboratories. The polymer was dissolved in o-dichlorobenzene in such a way that the concentration of the polymer reached about 1% by weight. As the mobile phase of GPC, o-dichlorobenzene was used and flowed at a flow rate of 1 mL / min at a measurement temperature of 140°C. As for the column, three pieces of PLGEL 10 μm MIXED-B (manufactured by PL Laboratories) were connected in series.
Synthetic example 1
[0100] (Synthesis of Polymer 1)
[0101]
[0102] In a 2L four-necked flask after the internal gas was replaced with argon, the above-mentioned compound A (7.928g, 16.72mmol), the above-mentioned compound B (13.00g, 17.60mmol), methyl trioctyl ammonium chloride (trade name : aliquat336, manufactured by Aldrich, CH 3 N[(CH 2 ) 7 CH 3 ] 3 Cl, density is 0.884g / ml, 25°C, trademark of Henkel Corporation) (4.979g) and toluene 405ml, argon gas is bubbled in the system for 30 minutes while stirring. Dichlorobis(triphenylphosphine)palladium(II) (0.02 g) was added, the temperature was raised to 105° C., and 42.2 ml of 2 mol / L sodium carbonate aqueous solution was added dropwise while stirring. After completion of the dropwise addition, the mixture was reacted for 5 hours, phenylboronic acid (2.6 g) and 1.8 ml of toluene were added, followed by stirring at 105° C. for 16 hours. 700 ml of toluene and 200 ml of a 7.5% sodium diethyldithiocarbamate trihydrate aqueous solution were...
Synthetic example 2
[0106] (Synthesis of Polymer 2)
[0107]
[0108] In a 200 ml separable flask, add methyl trioctyl ammonium chloride (trade name: aliquat336 (registered trademark), manufactured by Aldrich, CH 3 N[(CH 2 ) 7 CH 3 ] 3 Cl, density 0.884g / ml, 25°C) 0.65g, compound (C) 1.5779g and compound (E) 1.1454g, the gas in the flask was replaced with nitrogen. 35 ml of toluene bubbled with argon gas was added to the flask, and after stirring and dissolving, further bubbling with argon gas was performed for 40 minutes. After raising the temperature of the bath in the heating flask to 85°C, 1.6 mg of palladium acetate and 6.7 mg of tri-o-methoxyphenylphosphine were added to the reaction liquid, and then, the temperature of the bath was raised to 105°C for 6 minutes. 9.5 ml of a 17.5% by weight aqueous solution of sodium carbonate was added dropwise. After the dropwise addition, the reaction liquid was cooled to room temperature after stirring for 1.7 hours while maintaining the temper...
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