Doped organic semiconductive matrix material
A matrix material, semi-conductive technology, applied in the field of doped organic semi-conductive matrix materials, can solve problems such as aggravation
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Synthetic example 1
[0071] Synthesis Example 1, Synthesis of Compound-1
[0072]
[0073] Bis(biphenyl-4-yl)amine 10.0g (31.1mmol), 4,4'-diiodobiphenyl 5.28g (30.0mmol), anhydrous potassium carbonate 5.39g (39.0mmol), copper powder 0.083g (1.3 mmol), a mixture of dodecylbenzene 12 ml and xylene 24 ml was stirred and heated. After the xylene was evaporated, the mixture was reacted at 210-215°C for 4 hours. Further, 0.083 g (1.3 mmol) of copper powder was added to the mixture, and additional reaction was performed for 4.5 hours. After cooling to 90°C, toluene was added to the reaction mixture, and the reaction mixture was cooled to room temperature. The reaction mixture was filtered and washed with water, methanol and toluene. The residue was extracted with hot toluene and the toluene solution was concentrated to dryness in vacuo. The obtained crude product was purified by recrystallization. 7.38 g (yield: 71.7%) of N,N,N',N'-tetrakis(biphenyl-4-yl)-4,4'-diaminobiphenyl were obtained. Th...
Synthetic example 2
[0074] Synthesis example 2, the synthesis of compound-2
[0075]
[0076] Mix 20.3g (0.15mol) of acetanilide, 73.1g (0.18mol) of 4,4'-diiodobiphenyl, 22.1g (0.16mol) of anhydrous potassium carbonate, 2.16g (0.034mol) of copper powder and nitrobenzene 35ml. The reaction mixture was stirred at 190-205°C for 10 hours. The reaction mixture was extracted with 200 ml of toluene. Insoluble material was removed by filtration. The filtrate was concentrated to dryness. The resulting crude product was purified by column chromatography on silica gel and a 6 / 1 mixture of toluene and ethyl acetate as the eluent. 40.2 g (yield: 64.8%) of N-(4'-iodo-4-biphenyl)acetanilide were obtained. The melting point of the product is 135.0-136.0°C.
[0077] Subsequently, 13.2 g (0.032 mol) of N-(4'-iodo-4-biphenyl) acetanilide, 6.60 g (0.039 mol) of diphenylamine, 5.53 g (0.040 mol) of anhydrous potassium carbonate, and 0.45 g of copper powder were mixed (0.007mol) and nitrobenzene 10ml. The...
Synthetic example 3
[0082] Synthesis example 3, the synthesis of compound-3
[0083]
[0084] 20.30 g (63.16 mmol) of bis(biphenyl-4-yl)amine, 15.0 g (26.31 mmol) of 9,9-bis(4-iodophenyl)fluorene, 10.91 g (78.92 mmol) of anhydrous potassium carbonate, A mixture of 0.17 g (2.63 mmol) of copper powder and 30 ml of dodecylbenzene was stirred and heated at 200° C. for 13 hours in a nitrogen atmosphere.
[0085] The reaction mixture was analyzed by HPLC, and the intermediate monoiodide was confirmed to be 1% or less, and the reaction was assumed to be complete.
[0086] Toluene 100ml was added to the reaction mixture and filtered. The residue was washed with methanol and water.
[0087] The residue was added in 2000ml of chlorobenzene and heated to 120°C. After cooling to 60°C, the mixture was filtered and the filtrate was concentrated to dryness. The obtained crude product was purified by recrystallization from chlorobenzene 3 times.
[0088] The purified product 4',4"-bis[bis(4-biphenyl)am...
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