A kind of trisubstituted indole heterocyclic compound and organic optoelectronic device containing it
A technology for heterocyclic compounds and optoelectronic devices, applied in the field of tri-substituted indoloheterocyclic compounds and organic optoelectronic devices, can solve the problems of complex supporting equipment, complex structure of OLED devices, and great influence on the yield of devices, so as to improve luminescence. Efficiency, improved thermal stability, good hole injection and transport capabilities
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[0048] Preparation of representative intermediate material S4
[0049]
[0050] Preparation of OM-1:
[0051] (1) 6-chloro-dibenzofuran-4-boronic acid (5g) and 2,6-dibromonitro (5.6g) were completely dissolved in 150ml tetrahydrofuran in a 250ml round bottom flask under a nitrogen atmosphere, and then After adding 80 ml of 2M aqueous sodium carbonate solution, tetrakis-(triphenylphosphine)palladium (0.3 g) was added, and the mixture was heated and stirred for 8 hours. After cooling to room temperature, the aqueous layer was removed. Add 100 ml of dichloromethane, and wash twice with 30 ml of saturated brine. The dichloromethane layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo. Then petroleum ether: ethyl acetate (20:1~2:1) was used as eluent to purify and separate on a silica gel column to obtain O-S2 (yield 63%);
[0052]
[0053] (2) O-S2 (4g) and triethyl phosphite (10g) were completely dissolved in o-dichlorobenzene (120ml) in a 250ml r...
Embodiment 1
[0061] Synthesis of compound O-1:
[0062]
[0063] Under a nitrogen atmosphere, in a 250ml round bottom flask, OM-1 (4.5g) and 3-phenylphenylboronic acid (5g) were completely dissolved in 120ml of tetrahydrofuran, then 60ml of 2M aqueous sodium carbonate was added, and then tetrakis-(tri Phenylphosphine)palladium (0.3g), and the mixture was heated and stirred for 12 hours. After cooling to room temperature, the aqueous layer was removed. Add 100 ml of dichloromethane, and wash twice with 30 ml of saturated brine. The dichloromethane layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo. Then use petroleum ether:dichloromethane (20:1~2:1) as eluent to carry out purification and separation on a silica gel column to obtain O-1 (yield 89%); MS (ESI): 638.2 (M+H )
Embodiment 2
[0065] Synthesis of Compound O-34
[0066]
[0067] The 3-phenyl phenyl boronic acid in the embodiment 1 is replaced with the phenyl boronic acid of OM-1 equimolar ratio, other conditions are unchanged, can obtain the monosubstituted intermediate P-OM-1 (yield 82%), MS (ESI): 444.1 (M+H).
[0068] After P-OM-1 (5.2 g) and diphenylamine (3.2 g) were completely dissolved in xylene (80 ml) in a 100 ml round bottom flask under a nitrogen atmosphere, sodium tert-butoxide (4 g) was added thereto, di (Tri-tert-butylphosphine)palladium (0.1g), xphos (0.03g) The mixture was heated to reflux for 5-10 hours. After cooling down to room temperature, the salt was removed by filtration, and after the solvent was concentrated in vacuum, petroleum ether:dichloromethane (20:1~2:1) was used as eluent to purify and separate on a silica gel column to obtain O-34 (yield 86%); MS (ESI): 577.2 (M+H)
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