Pyrene derivatives as well as preparation method and application
A technology of pyrene derivatives and compounds, which is applied in the field of electroluminescent materials, can solve the problems of increased large-scale preparation cost, poor device stability, complicated preparation process, etc., and achieves the effects of high work efficiency, good stability and high color purity.
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Embodiment 1
[0117] (1) Synthesis of intermediate 1
[0118] Starting material 1 (1.10 g), starting material 2 (1.44 g), anhydrous sodium carbonate (2.12 g) and tetrakis(triphenylphosphine)palladium (0.1 g) were placed in a flask. Then, 30 ml of toluene, 10 ml of ethanol and 10 ml of distilled water were added. Under the protection of nitrogen, the reaction was refluxed at 100° C. for 24 hours. After the reaction was completed, the reaction solution was evaporated to dryness under reduced pressure, and the residual solid was purified by column chromatography using petroleum ether as the eluent to obtain 0.88 g of a white powdery solid, namely Intermediate 1, with a yield of 43%.
[0119] The NMR results of intermediate 1 are as follows:
[0120] 1 H NMR (500MHz, CDCl 3 )δ (ppm): 8.51 (1H, d, J = 9.2), 8.36-8.33 (2H, m), 8.29-8.25 (2H, m), 8.16 (1H, d, J = 7.8), 8.05-8.02 ( 2H,m),7.98(1H,s),7.87(2H,s),7.78(4H,d,J=7.5),7.52(4H,t,J=7.5),7.43(2H,t,J=7.4 ).
[0121] The reaction equation...
Embodiment 2
[0141] (1) Synthesis of Intermediate 1
[0142] Same as Intermediate 1 of Example 1.
[0143] (2) Synthesis of Intermediate 4
[0144] Starting material 1 (1.15 g), starting material 4 (1.12 g), anhydrous sodium carbonate (2.12 g) and tetrakis(triphenylphosphine)palladium (0.1 g) were placed in a flask. Then, 30 ml of toluene, 10 ml of ethanol and 10 ml of distilled water were added. Under the protection of nitrogen, the reaction was refluxed at 80° C. for 24 hours. After the reaction was completed, the reaction solution was evaporated to dryness under reduced pressure, and the residual solid was purified by column chromatography. The eluent was a mixed solution of petroleum ether and dichloromethane (10:1 by volume) to obtain a white powdery solid. That is intermediate 4 with a yield of 86%.
[0145] The nuclear magnetic assay result of intermediate 4 is as follows:
[0146] 1 H NMR (500MHz, CDCl 3 )δ(ppm):7.83(1H,s),7.72-7.69(5H,m),7.63(2H,s),7.48-7.44(5H,m),7.40-7.35...
Embodiment 3
[0160] The photophysical property test of embodiment 3 material
[0161] The photophysical properties of samples C1 and C2 were tested, and the test results of sample C1 were as follows: image 3 shown. The luminescence peak of sample C1 in dichloromethane solution is at 400nm, and there is a shoulder peak at 418nm, and the luminescence peak in solid film state is at 425nm; The luminescence quantum efficiency in dichloromethane solution is 62% (by 9 , 10-diphenylanthracene as reference). The test results of sample C2 are as follows Figure 4 Shown, the luminescence peak in dichloromethane solution is positioned at 395nm, and there is a shoulder peak at 410nm place, and the luminescence peak in the solid film state is positioned at 413nm; The luminous quantum efficiency in dichloromethane solution is 68% (with 9,10-diphenylanthracene as reference).
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