Aromatic Amine Derivative and Organic Electroluminescent Device Using Same
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synthesis example 1
Synthesis of Intermediate 1
[0206]20.0 g of 4-bromobiphenyl (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.) 8.64 g of sodium t-butoxide (manufactured by Wako Pure Chemical Industries, Ltd.), and 84 mg of palladium acetate (manufactured by Wake Pure Chemical Industries, Ltd.) were loaded into a 200-mL three-necked flask. Further, a stirring rod was placed in the flask, and rubber caps were set on both side ports of the flask. A reflux condenser was inserted into the central port of the flasks and a three-way cock and a balloon in which an argon gas was sealed were set above the condenser. The inside of the system was replaced with the argon gas in the balloon three times by using a vacuum pump.
[0207]Next 120 mL of dehydrated toluene (manufactured by HIROSHIMA WAKO CO., LTD.), 4.08 mL of benzylamine (manufactured by TOKYO CHEMICAL INDUSTRY CO. LTD.) and 338 μL of tri-t-butylphosphine (manufactured by SIGMA-ALDRICH, 2.22-mol / L toluene solution) were added to the flask by using a syr...
synthesis example 2
Synthesis of Intermediate 2
[0214]In a stream of argon, 10 g of di-4-biphenylylamine, 9.7 g of 4,4-dibromobiphenyl (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.), 3 g sodium t-butoxide manufactured by HIROSHIMA WAKO CO., LTD.), 0.5 g of bis(triphenylphosphine)palladium(II) chloride (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.), and 500 mL of xylene were loaded, and the whole was subjected to a reaction at 130° C. for 24 hours.
[0215]After the resultant had been cooled, 1,000 mL of water were added to the resultant, and the mixture was subjected to Celite filtration. The filtrate was extracted with toluene and dried with anhydrous magnesium sulfate. The dried product was condensed under reduced pressure, and the resultant crude product was subjected to column purification. The purified product was recrystallized with toluene. The crystal was taken by filtration, and was then dried, whereby 4.6 g of 4′-bromo-N,N-dibiphenylyl-4-amino-1,1′-biphenyl (Intermediate 2) shown below ...
synthesis example 3
Synthesis of Intermediate 3
[0216]In a stream of argon, 6.8 g of N-phenyl-1-naphthylamine (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD), 9.7 g of 4,4′-dibromobiphenyl (manufactured by TOKYO CHEMICAL INDUSTRY CO. LTD.), 3 g of t-butoxy sodium (manufactured by HIROSHIMA WAKO CO. LTD.), 0.5 g of bis(triphenylphosphine)palladium(II) chloride (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.), and 500 mL of xylene were loaded, and the whole was subjected to a reaction at 130° C. for 24 hours.
[0217]After the resultant had been cooled, 1,000 mL of water were added to the resultant, and the mixture was subjected to Celite filtration. The filtrate was extracted with toluene and dried with anhydrous magnesium sulfate. The dried product was condensed under reduced pressure, and the resultant crude product was subjected to column purification. The purified product was recrystallized with toluene. The crystal was taken by filtration, and was then dried, whereby 4.1 g of 4′-bromo-N-phenyl-N-...
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