A class of heterocyclic bridged phenylethylene derivatives and their preparation methods and applications
A technology for bridging phenylethylene and derivatives, which is applied in the field of organic optoelectronic materials, can solve the problems of luminescence quenching, low solid-state luminescence quantum yield, and reduce the luminescence performance of devices, and achieves excellent device performance and good hole transport capability. , the effect of good AIE characteristics
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Embodiment 1
[0044] Example 1: Preparation of organic electroluminescent material (1) based on carbazole-substituted sulfur-bridged tetraphenylethylene, that is, preparation of heterocyclic bridged tetraphenylethylene derivatives:
[0045]
[0046] The synthetic route is as follows:
[0047]
[0048] (1) Dibromothioxanthene (9-(dibromomethylene)-9 hydrogen-thioxanthene) (0.18g, 0.5mmol), carbazole boronic acid (4-(9H-carbazol-9-yl ) phenylboronic acid) (0.57g, 2mmol), tetrakis (triphenylphosphine) palladium (0.116g, 0.1mmol) and potassium carbonate (0.69g, 5mmol) were dissolved in a mixed solvent of tetrahydrofuran (80mL) and water (20mL) , and degassed by nitrogen for half an hour, and then heated the reaction mixture to reflux for 24 hours; then at 80 ° C, the solvent volatiles were blown off with compressed air, the mixture was cooled to room temperature (22 ° C), and dichloromethane was added (100mL), the solid residue was filtered off and the extract was washed with dichloromet...
Embodiment 2
[0050] Example 2: Preparation of organic electroluminescent material (2) based on carbazole-substituted sulfone group-bridged tetraphenylethylene, that is, preparation of heterocyclic bridged tetraphenylethylene derivatives:
[0051]
[0052] The synthetic route is as follows:
[0053]
[0054] (1) Dibromosulfoxanthene (9-(dibromomethylene)-9 hydrogen-thioxanthene-10,10-dioxide) (0.20g, 0.5mmol), carbazole boronic acid (0.57g, 2mmol), tetrakis(triphenylphosphine)palladium (0.116g, 0.1mmol) and potassium carbonate (0.69g, 5mmol) were dissolved in a mixed solvent of tetrahydrofuran (80mL) and water (20mL), and degassed by nitrogen hour, and then the reaction mixture was heated to reflux for 24 hours; then at 80°C, the solvent volatiles were blown off with compressed air; after the mixture was cooled to room temperature (22°C), dichloromethane (100mL) was added, and the solid residue was filtered off The extract was washed with dichloromethane (3×100mL), the filtrate was w...
Embodiment 3
[0056] Example 3: Preparation of organic electroluminescent material (3) based on diphenylamine-substituted sulfur-bridged tetraphenylethylene, that is, preparation of heterocyclic bridged tetraphenylethylene derivatives:
[0057]
[0058] The synthetic route is as follows:
[0059]
[0060] (1) Dibromothioxanthene (9-(dibromomethylene)-9 hydrogen-thioxanthene) (0.18g, 0.5mmol), diphenylamine boronic acid (4-dianilinophenylboronic acid) (0.58g , 2mmol), tetrakis(triphenylphosphine)palladium (0.116g, 0.1mmol) and potassium carbonate (0.69g, 5mmol) were dissolved in a mixed solvent of tetrahydrofuran (80mL) and water (20mL), and degassed by nitrogen After half an hour, the reaction mixture was heated to reflux for 24 hours; then at 80° C., the solvent volatiles were blown off with compressed air; after the mixture was cooled to room temperature (22° C.), dichloromethane was added to dissolve the crude product (100 mL), The solid residue (filter residue) was filtered off a...
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