Novel styryl compound and organic electroluminescence device
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synthesis example 1
[0047] Compound (1) was synthesized in accordance with the following route of reactions:
[0048] Into a 200 ml three-necked flask equipped with a condenser, 2.8 g (10 mmole) of 4,4′-diaminostilbene dihydrochloride, 10.3 g (44 mmole) of 4-bromobiphenyl, 0.14 g (1.5% by mole) of tris(dibenzylideneacetone)-dipalladium, 0.06 g (3% by mole) of tri-t-butylphosphine, 4.2 g (44 mmole) of sodium t-butoxide and 100 ml of dry toluene were placed under argon and the resultant mixture was stirred under heating at 100° C. for one night. After the reaction was completed, precipitated crystals were separated by filtration and washed with 100 ml of methanol and 4.9 g of a yellow powder was obtained. The obtained product was identified to be compound (1) by the measurements in accordance with NMR, IR and FD-MS (the field desorption mass spectroscopy) (the yield: 60%). The NMR chart of compound (1) is shown in FIG. 1.
synthesis example 2
[0049] Compound (2) was synthesized in accordance with the following route of reactions:
[0050] Synthesis of Intermediate A
[0051] Into a flask containing a solvent, 150 g (0.6 mole) of 4-bromobenzyl bromide and 299 g (1.8 mole) of ethyl phosphite were placed and the resultant mixture was stirred under the condition of refluxing for 18 hours. After the reaction was completed, the solvent was removed from the reaction mixture by distillation under a reduced pressure. From the residue of the distillation, ethyl phosphite was removed by distillation under a further reduced pressure (bp. 75° C. / 2 torr) and 185 g (the yield: 100%) of the object substance was obtained as the residue of the distillation.
[0052] Synthesis of Intermediate B
[0053] Into a solution containing 185 g (0.6 mole) of intermediate A, 134 g (0.72 mole) of 4-bromobenzaldehyde and 1850 ml of dimethylsulfoxide, 81 g (0.72 mole) of potassium t-butoxide was added in small portions over 30 minutes and the resultant mixtur...
synthesis example 3
Compound (3)
[0058] Compound (3) was synthesized in accordance with the following route of reactions:
[0059] Into a 200 ml three-necked flask equipped with a condenser, 3.6 g (10 mmole) of intermediate C, 5.6 g (22 mmole) of 9-bromophenanthrene, 0.14 g (1.5% by mole) of tris(dibenzylideneacetone)dipalladium, 0.06 g (3% by mole) of tri-t-butylphosphine, 4.2 g (44 mmole) of sodium t-butoxide and 100 ml of dry toluene were placed under argon and the resultant mixture was stirred under heating at 100° C. for one night. After the reaction was completed, precipitated crystals were separated by filtration and washed with 100 ml of methanol and 5.7 g of a yellow powder was obtained. The obtained product was identified to be compound (3) by the measurements in accordance with NMR, IR and FD-MS (the yield: 80%). The NMR chart of compound (3) is shown in FIG. 3.
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