Aromatic amine derivatives, preparation method thereof, application and organic electroluminescent device
An aryl, unsubstituted technology, applied in the field of aromatic amine derivatives, can solve the problems of poor thermal stability of materials, easy crystallization or agglomeration, shortened device life, etc., and achieves Tg increase, glass transition temperature increase, and turn-on voltage decrease. Effect
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Embodiment 1
[0189] Embodiment 1: the preparation of formula (I) compound
[0190] 1. Preparation of compound I-1
[0191]
[0192] Under nitrogen protection, add 5.14g (0.01mol) 2,10-dibromo-6-trimethylphenyl-6H-6-borabenzo[cd]pyrene of formula II-1 in a 250ml three-neck round bottom flask, formula 3.72g (0.022mol) diphenylamine of III-1, Pd(dba) 2 (0.12g, 1.0mol%), 0.4ml (1.0mol%) 10% by weight of P(t-Bu) 3 cyclohexane solution and NaO(t-Bu) (1.92g, 0.02mol), and then 80ml of anhydrous-treated toluene was added to obtain a reaction solution. The above reaction solution was refluxed in an oil bath at 110°C for 5 hours under magnetic stirring, cooled, and then the reaction solution was washed with an appropriate amount of water for 2-3 times before liquid separation, and the obtained organic phase was washed with anhydrous MgSO 4 Drying, followed by rotary evaporation to remove the organic solvent gave the crude product. The crude product was separated by silica gel (200-300 mesh, Q...
Embodiment 2
[0242] Embodiment 2: the preparation of formula (II) compound
[0243] Preparation of compound II-1 (2,10-dibromo-6-trimethylphenyl-6H-6-borabenzo[cd]pyrene)
[0244]
[0245] Preparation of Compound X-1: Under nitrogen protection, add 47.2g (0.2mol) o-dibromobenzene XI-1 and 200mL anhydrous ether to a 500mL three-neck round-bottomed flask, cool to -78°C, and slowly drop under magnetic stirring Add 80mL n-BuLi (0.2mol, 2.5mol L -1 in n-hexane). After maintaining the temperature for 1 h, the temperature was naturally raised to room temperature and the reaction was continued with stirring for 2 h. Then after cooling to -78°C again, add 50 mL of MesityB (OMe) dissolved with 19.2 g (0.1 mol) of compound XII-1 2 ether solution, stirred for 1h. Slowly rise to room temperature, continue the reaction overnight, add an appropriate amount of water for hydrolysis, extract 2-3 times with ethyl acetate, and combine the organic phases. Anhydrous MgSO 4 After drying, the organic sol...
Embodiment 3
[0252] Embodiment 3: the preparation of formula (III) compound
[0253] 1. Preparation of compound III-2
[0254]
[0255] Under nitrogen protection, add 10.65g (0.05mol) 4-tert-butyl bromobenzene, 8.94g (0.06mol) 4-tert-butylaniline, 0.14g (0.5mol%) Pd(dba) in a 500ml three-neck round bottom flask 2 , 0.5ml (0.5mol%) 10% by weight P (t-Bu) 3 cyclohexane solution and 4.80g (0.05mol) NaO (t-Bu), then add 260ml of toluene through anhydrous treatment, obtain reaction solution . The above reaction solution was refluxed in an oil bath at 110°C for 3 hours under magnetic stirring, cooled, and then the reaction solution was washed with an appropriate amount of water for 2-3 times before liquid separation, and the obtained organic phase was washed with anhydrous MgSO 4 Drying, followed by rotary evaporation to remove the organic solvent gave the crude product. The crude product was recrystallized through a petroleum ether-ethanol system to obtain 11.3 g of white crystals, with a...
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