A kind of 1,3-azaphosphorole compound and its synthesis method
A technology of heterocyclopentadiene and compound, applied in 1 field, can solve problems such as unreported research, and achieve the effects of high external quantum efficiency, high yield and high current efficiency
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Embodiment 1
[0016] The synthetic method of embodiment 1 compound I-c to I-e, the steps are as follows:
[0017] a) Synthesis of compound I-c
[0018]
[0019] Take 3.4mmol of the raw material of the compound of formula A1 in a 100mL schlenk bottle, vacuumize and change nitrogen three times, add 30mL of anhydrous tetrahydrofuran, then cool the system down to -78°C, add n-BuLi 3.4mmol dropwise, and react the system at -78°C 0.5h. Then 3.4 mmol of 9,10-dibromophenanthrene was added, and the reaction returned to room temperature by itself, and reacted for 0.5 h. After the reaction was completed, it was extracted with ethyl acetate and water, and the organic phases were combined. After distillation under reduced pressure, the compound A2 was obtained by column chromatography using petroleum ether: dichloromethane = 15:1 as the eluent.
[0020] A2 yield: 68%, yellow solid, while recovering 14% of 9,10-dibromophenanthrene, 1 H NMR (300MHz, CDCl 3 )δ=5.85-5.86 (m, 2H), 6.59-6.60 (m, 2H), 7...
Embodiment 2
[0032] The synthetic method of embodiment 2 compound II-a to II-e, the steps are as follows:
[0033]
[0034] Take 2 mmol of the raw materials of series compound I in a Schlenk bottle, vacuumize and change nitrogen three times, add 20 mL of anhydrous tetrahydrofuran, add 4 mmol of N,N,N',N'-tetramethylethylenediamine, and then control the temperature of the system to 0 ℃, n-BuLi4mmol was added dropwise, and the system was reacted at 0℃ for 1h. After the reaction was completed, 2 mmol of phenylphosphorous dichloride was added, and the reaction was carried out at 0° C. for 10 minutes, and then the system was returned to room temperature for reaction. After the reaction is finished, 30% by mass hydrogen peroxide solution or sulfur powder is added to the system for reaction. After extraction, the organic phases were combined, distilled under reduced pressure, and separated by column chromatography to obtain a series of target compounds II.
[0035] II-aO yield: 42%, yellow s...
Embodiment 3
[0044] The synthetic method of embodiment 3 compound II-fO, the steps are as follows:
[0045]
[0046] Take 2.2 mmol of magnesium powder in a Schlenk bottle, vacuumize and change nitrogen three times, add 10 mL of anhydrous tetrahydrofuran, add a grain of iodine, and then raise the temperature of the system to 60°C. After 20 minutes, 2 mmol of the compound of formula A4 was added until the reaction was complete (system 1).
[0047] Take another Schlenk bottle, vacuumize and change nitrogen three times, add 10 mL of anhydrous tetrahydrofuran, add 2 mmol of phosphorus trichloride, and then cool the system down to -78°C (system 2). The materials in system 1 were added dropwise into system 2 with a syringe. After 30 minutes, aryl phosphorus dichloride A5 containing a carbazole group was reacted, and the system was returned to room temperature (system 3).
[0048] Take 1 mmol of compound I-d raw material in another Schlenk bottle, vacuum three times for nitrogen, add 10 mL of ...
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