Organic molecular materials based on dibenzo five-membered aromatic heterocyclic rings and their synthesis methods and applications as hole transport layers
A technology of organic molecular materials and hole transport layers, applied in organic chemistry, electrical components, electrical solid devices, etc., can solve the problems of high purification cost and many synthesis steps of spirobifluorenyl structure, and achieve the effect of low cost
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Embodiment 1
[0031] Example 1, N 2 ,N 2 ,N 8 ,N 8 -Synthesis of tetrakis(4-(methylthio)phenyl)diphenyl[b,d]thiophene-2,8-diamine (DBT-MTP)
[0032] Add 50ml of toluene to the two-necked flask, take bis(4-(methylthio)phenyl)amine (formula V, 1.723g, 6.6mmol, 2.2 equivalents), 2,8-dibromobisphenyl[b,d] Thiophene (formula III, 1.026 g, 3 mmol), tris(dibenzylideneacetone) dipalladium (54.9 mg, 0.02 equivalents), tri-tert-butylphosphine tetrafluoroborate (26.1 mg, 0.03 equivalents) and sodium tert-butoxide ( 0.864g, 3 equivalents) was added into the flask, and stirred and reacted in an oil bath for 12h. After the solution was cooled, deionized water and dichloromethane were added for extraction three times, the organic phases were combined, and the organic phase was washed twice with saturated aqueous sodium chloride solution. Add anhydrous magnesium sulfate to dry, spin to dry the solvent, and then use neutral alumina chromatography column to purify, and the eluent is 1:18 (v / v) ethyl ace...
Embodiment 2
[0037] Example 2. The photovoltaic properties of the reverse perovskite solar cell based on DBT-MTP as the hole transport layer. The DBT-MTP hole transport layer is prepared based on CH 3 NH 3 PB 3 Perovskite solar cell devices.
[0038] The reverse device structure is ITO / DBT-MTP / CH 3 NH 3 PB 3 / C 60 / BCP / Ag( image 3 ).
[0039] The preparation method of the reverse device is as follows: ITO glass was ultrasonically washed with detergent, ethanol, and acetone for 15 minutes, dried with dry air, and treated with UVO for 20 minutes. The DBT-MTP hole transport material was then spin-coated at 5000 rpm (40 s), and the hole transport material was dissolved in 1 ml of chlorobenzene. Then annealed at 100°C for 5 min in a glove box. Spin-coat PbI at 3500rpm 2 , after 20s drop CH 3 NH 3 I, anneal at 90°C for 8 minutes after the operation. On the perovskite layer, 20nm C was evaporated successively by evaporation method. 60 And 8nm BCP. Finally at 2.0×10 -6 A layer of ...
Embodiment 3
[0041] Example 3, N 2 ,N 2 ,N 8 ,N 8 -Synthesis of tetrakis(4-(methylthio)phenyl)diphenyl[b,d]furan-2,8-diamine (DBF-MTP)
[0042] Add 50ml of toluene in the two-necked flask, get bis(4-(methylthio)phenyl)amine (formula V, 1.723g, 2.2 equivalents), 2,8-dibromobisphenyl[b,d]furan (formula IV, 0.978g, 3mmol), tris(dibenzylideneacetone)dipalladium (54.9mg, 0.02 equivalent), tri-tert-butylphosphine tetrafluoroborate (26.1mg, 0.03 equivalent) and sodium tert-butoxide (0.864g, 3 equivalents) was added to the flask, stirred and reacted in an oil bath for 12h. After the solution was cooled, deionized water and dichloromethane were added for extraction three times, the organic phases were combined, and the organic phase was washed twice with saturated aqueous sodium chloride solution. Add anhydrous magnesium sulfate to dry, and use neutral alumina chromatography column to purify, eluent is 1:20 (v / v) ethyl acetate / petroleum ether. The obtained product was dissolved in acetone and...
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