Boron-containing heterocyclic compound and application thereof in organic photoelectric device
A technology of compound and boron heterocycle, applied in the field of boron-containing heterocycle compound and its application in organic optoelectronic devices, to achieve high thermal stability, low voltage, and improve the effect of luminescence stability
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[0111] Example 1:
[0112]
[0113] Add 25g of compound 3-1, 25g of 2,4-dibromo-1-fluoro-benzene, 300ml of dimethyl sulfoxide (DMSO) into a 500ml three-necked flask, blow nitrogen, stir to completely dissolve the raw materials, add K 2 CO 3 16.5g, the solution is yellow. Turn on heating to 110°C and react for 8 hours and then sample for monitoring. After the raw materials have reacted completely, the temperature is lowered to room temperature for post-processing.
[0114] The reaction solution was added to 3 times the volume of water, stirred to precipitate the product, filtered, the filter cake was dissolved in toluene, and washed with water to neutrality. Anhydrous Na 2 SO 4 After drying for 2 hours, the desiccant was removed by filtration, the filter cake was rinsed with a small amount of toluene, the filtrate was combined, concentrated, and purified by column to obtain the target compound 3-2 as a yellow solid 36.1 g, with a yield of 76.2%.
[0115] 1 H NMR (400MHz, CDC13) δ 7....
Example Embodiment
[0116] Example 2:
[0117]
[0118] Add 36g of compound 3-2, 300ml of tetrahydrofuran (THF) in a 1L three-necked flask, replace the air in the reaction flask with nitrogen, cool to -78℃, and slowly add n-butyllithium (n-BuLi)( 2.0M in THF) 75ml, keep the reaction at this temperature for 2h, add 9.6g of phenylboronic acid, keep this temperature and continue the reaction for 6h, then naturally warm to room temperature, TLC monitors the raw material reaction is complete, add 1M ammonium chloride solution to adjust the pH to medium After stirring for 10 minutes, let it stand for liquid separation. Anhydrous Na for organic phase 2 SO 4 After drying for 2 hours and filtering, the filtrate was concentrated and passed through a silica gel column to obtain 20.1 g of compound 3-3 as a white solid with a yield of 65.3%.
[0119] 1 H NMR (400MHz, CDC13) δ7.42 (t, J=7.6, 1H), 7.35 (t, J=7.6, 2H), 7.31 (d, J=7.6, 2H), 7.22-7.24 (m, 4H) , 7.18 (d, J=7.6, 2H);
Example Embodiment
[0120] Example 3:
[0121]
[0122] Add 20g of compound 3-3, 200ml of glacial acetic acid (AcOH), 13g of 30% hydrogen peroxide to a 500ml three-necked flask, stir the reaction at room temperature for 2h, TLC monitors until the raw material has reacted completely, add 1M sodium bicarbonate solution to adjust the pH to neutral. After stirring for 10 min, let it stand for liquid separation. The aqueous phase was extracted with dichloromethane, and the organic phases were combined with anhydrous Na 2 SO 4 After drying for 2 hours and filtering, the filtrate was concentrated and passed through a silica gel column to obtain 20.1 g of compound 3-4 as a white solid with a yield of 93.5%.
[0123] 1 H NMR (400MHz, CDC13) δ 7.82 (d, J=8.0, 2H), 7.66-7.73 (m, 4H), 7.42 (t, J=7.6, 1H), 7.35 (t, J=7.6, 2H) , 7.31(d, J=7.6, 2H);
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