An organic light-emitting material containing an acceptor structural unit of a benzo[c][1,2,5]thiadiazole derivative and its application
A technology of thiadiazole derivatives and light-emitting materials, applied in light-emitting materials, organic chemistry, electrical components, etc., can solve problems such as high price and limited resources
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Embodiment 1
[0050] Embodiment 1: The synthetic route of luminescent material BTN-1 is as follows:
[0051]
[0052] Synthesis of Intermediate 1: Combine 3-methyl-1,2-phenylenediamine (30.53 g, 249.87 mmol, 1.0 equiv), triethylamine (138.92 mL, 999.47 mmol, 4.0 equiv) and dichloromethane (300 mL) A dry three-necked flask equipped with magnetic stirring was sequentially added and placed in an ice bath. The mixture was stirred for more than 1 hour, after which thionyl chloride (36.25 mL, 499.74 mmol, 2.0 equiv) and dichloromethane (100 mL) were slowly added dropwise, the mixture was stirred at this temperature for 1 hour, and the mixture was placed in an oil bath, Stir at 40°C for 20 hours and monitor the reaction by thin layer chromatography until the reaction is complete. The reaction was quenched and the resulting mixture was cooled to room temperature and quenched with water. The mixture was extracted three times with ethyl acetate. The combined organic phases were washed with wate...
Embodiment 2
[0060] Embodiment 2: The synthetic route of luminescent material BTN-2 is as follows:
[0061]
[0062] Synthesis of 2-Br: 3,6-di-tert-butylcarbazole (3.19 g, 11.41 mmol, 1.0 equiv), 1-bromo-4-iodobenzene (3.55 g, 12.55 mmol, 1.1 equiv), iodide Copper (217.2 mg, 1.14 mmol, 0.1 equiv), L-proline (262.6 mg, 2.28 mmol, 0.2 equiv) and potassium carbonate (2.63 g, 22.81 mmol, 2.0 equiv) were sequentially added to a dry three-necked flask equipped with magnetic stirring middle. The nitrogen was purged three times, then dimethyl sulfoxide (60 mL) was added under nitrogen protection, and the mixture was placed in an oil bath and heated to 100°C to react. After 36 hours, the reaction was monitored by thin layer chromatography until completion. The resulting mixture was cooled to room temperature and diluted with dichloromethane. The mixture was washed three times with brine and extracted three times with dichloromethane. The combined organic layers were dried over anhydrous sodi...
Embodiment 3
[0066] Embodiment 3: The synthetic route of luminescent material BTN-3 is as follows:
[0067]
[0068]Synthesis of 3-Br: 3,6-diphenylcarbazole (3.33 g, 10.42 mmol, 1.0 equiv), 1-bromo-4-iodobenzene (3.24 g, 11.46 mmol, 1.1 equiv), cuprous iodide (39.7 mg, 0.21 mmol, 0.02 equiv) and sodium tert-butoxide (2.00 g, 20.81 mmol, 2.0 equiv) were sequentially added to a dry three-necked flask equipped with magnetic stirring. The nitrogen was purged three times, then 1,2-trans-cyclohexanediamine (0.13 mL, 1.04 mmol, 0.1 equiv) and 1,4-dioxane (100 mL) were added under nitrogen protection, and the mixture was placed in an oil bath and stirring the reaction at 100 °C. The reaction was monitored by thin layer chromatography until completion and was stopped after 48 hours. The resulting mixture was cooled to room temperature and quenched by the addition of water. The mixture was extracted three times with dichloromethane. The combined organic layers were washed with water, dried ov...
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