Organic molecules for use in organic optoelectronic devices
An organic molecule, organic technology, applied in the field of organic molecules used in organic optoelectronic devices, can solve problems such as disadvantages
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Embodiment 1
[0153] Synthesis (Stage 1):
[0154]
[0155] 3-Bromo-4-fluorobenzonitrile (125 mmol), phenylboronic acid (188 mmol), palladium acetate (2.5 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxy-1, 1'-biphenyl (SPhos; 5 mmol) and tribasic potassium phosphate (250 mmol) were suspended in 200 ml of toluene under nitrogen. After adding 10 ml of degassed water, the reaction mixture was blanketed with nitrogen for 20 min. After stirring at 110°C for 18 hours and cooling to room temperature, the reaction solution was filtered and the solid was washed with ethyl acetate. Filtrate with MgSO 4 dry. After removal of the solvent, the crude product was recrystallized from n-hexane. 3-Phenyl-4-fluorobenzonitrile (15.9 g, 80.6 mmol, 64%) was obtained as a white solid.
[0156] 1 H NMR (500MHz, chloroform-d) δ 7.77 (dd, J=7.1, 2.2Hz, 1H) 7.64 (ddd, J=8.5, 4.5, 2.2Hz, 1H), 7.54–7.42 (m, 5H) 7.27 ( dd, J=9.9, 8.5 Hz, 1H).
[0157] Stage 2:
[0158]
[0159] 3-Phenyl-4-fluorobenzonitril...
Embodiment 2
[0165]
[0166] 9,10-Dihydro-9,9-dimethylacridine (10 mmol), 4-bromo-3-methylbenzonitrile (15 mmol) and palladium acetate (0.5 mmol) were suspended in 50 ml of toluene under nitrogen. After nitrogen was passed through the reaction mixture for 30 min, tri-tert-butylphosphine (0.75 mmol) and sodium tert-butoxide (15 mmol) were added, and the mixture was refluxed with stirring for 2.5 hours. After stirring for 16 hours at room temperature, 50 ml of water were added and the mixture was extracted twice with 50 ml of ethyl acetate. The combined organic phases were washed with saturated NaCl solution and washed with MgSO 4 dry. After removal of the solvent, the residue was recrystallized from ethanol. The product 2 was obtained (4.9 mmol, 49%).
[0167] 1 H NMR (500MHz, chloroform-d) δ 7.81 (d, J=1.9Hz, 1H), 7.75 (dd, J=8.1, 1.9Hz, 1H), 7.53-7.46 (m, 2H) 7.38 (d, J) = 8.0 Hz, 1H), 7.04-6.91 (m, 4H), 6.07-5.97 (m, 2H), 2.14 (s, 3H), 1.74 (s, 3H) 1.68 (s, 3H).
[0168] The abs...
Embodiment 3
[0170]
[0171] 3-Phenyl-4-fluorobenzonitrile (10 mmol), 2,3:5,6-dibenzo-1,4-oxazine (10 mmol) and tripotassium phosphate (20 mmol) were suspended under nitrogen in DMSO ( 20ml) and stirred at 125°C (14h). The reaction mixture was then introduced into 400 ml of saturated sodium chloride solution and extracted with dichloromethane (3 x 150 ml). The combined organic phases were washed with saturated sodium chloride solution (2 x 150 ml) and dried over magnesium sulfate, then the solvent was removed. The crude product was finally purified by recrystallization from toluene. Product 3 was obtained as a yellow solid.
[0172] 1 H NMR (500MHz, chloroform-d) δ 7.91 (d, J=1.9Hz, 1H), 7.85 (dd, J=8.1, 2.0Hz, 1H), 7.57 (d, J=8.1Hz, 1H), 7.35 -7.29(m,5H),6.65-6.59(m,4H),6.59-6.54(m,2H),5.90-5.83(m,2H).
[0173] exist Image 6 Film emission of 3 can be seen in (10% in PMMA). The emission maximum is at 494 nm. The photoluminescence quantum yield (PLQY) was 65%.
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