Bipolar red phosphorescent compound, preparation method thereof and organic electroluminescent device
A compound, bipolar technology, applied in the field of organic semiconductor materials, can solve the problems of lack of host materials, high driving voltage, low glass transition temperature, etc. Effect
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[0031] The preparation method of the above-mentioned bipolar red light phosphorescent compound comprises the following steps:
[0032] S1. In an oxygen-free environment (by nitrogen, argon, or a mixture of nitrogen and argon), the structural formula is The compound A (that is, 9-(4-((4-iodophenyl)diphenylsilyl)phenyl)-9H-carbazole) is dissolved in the organic solvent, and then added to the organic solvent with the structural formula: compound B (i.e. thiophenol), then add inorganic base and catalyst to the organic solvent, react at 70-120°C for 3-12 hours, stop the reaction and cool to room temperature, the structural formula is Compound C (that is, 9-(4-(diphenyl(4-(phenylthio)phenyl)silyl)phenyl)-9H-carbazole); wherein, the molar ratio of compound A to compound B is 1:1~1:1.2; the reaction formula is as follows:
[0033]
[0034] S2. Dissolve compound C in dichloromethane at 0°C to obtain a mixed solution, and then drop the mixed solution into m-chlorobenzoic acid (m...
Embodiment 1
[0057] The bipolar red phosphorescent compound of this example is: 9-(4-(diphenyl-(4-(phenylsulfonyl)phenyl)silyl)phenyl)-9H-carbazole, the structural formula is as follows :
[0058]
[0059] The preparation process of this compound is as follows:
[0060] The first step, the preparation of compound C
[0061]
[0062] Under nitrogen protection, 9-(4-((4-iodophenyl)diphenylsilyl)phenyl)-9H-carbazole (50.2g, 80mmol) was dissolved in 200mL N,N-dimethylformamide (DMF) solution, then add thiophenol (8.8g, 80mmol), potassium carbonate (22.1g, 160mmol), cuprous iodide (1.52g, 8mmol). The mixture was stirred and reacted at 120°C for 3 hours. The reaction was stopped and cooled to room temperature, filtered, and the solid was washed three times with distilled water. The crude product was separated by silica gel column chromatography using n-hexane as the eluent to obtain Compound C as an off-white solid. The yield was 91%.
[0063] The second step, the preparation of 9-(4-...
Embodiment 2
[0068] The bipolar red phosphorescent compound of this example is: 9-(4-(diphenyl-(4-(phenylsulfonyl)phenyl)silyl)phenyl)-9H-carbazole, the structural formula is as follows :
[0069]
[0070] The preparation process of this compound is as follows:
[0071] The first step, the preparation of compound C
[0072]
[0073] Under argon protection, 9-(4-((4-iodophenyl)diphenylsilyl)phenyl)-9H-carbazole (50.2g, 80mmol) was dissolved in 200mL toluene (Tol) solution, Then thiophenol (9.68g, 88mmol), cesium carbonate (57.2g, 176mmol), copper powder (0.768g, 12mmol) were added. The mixture was stirred and reacted at 110°C for 6 hours. The reaction was stopped and cooled to room temperature, filtered, and the solid was washed three times with distilled water. The crude product was separated by silica gel column chromatography using n-hexane as the eluent to obtain Compound C as an off-white solid. The yield was 93%.
[0074] The second step, the preparation of 9-(4-(diphenyl-(...
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