Thermally activated delayed fluorescent material based on 4‑fluorophenylacetonitrile and its preparation and application
A technology of delayed fluorescence and fluorophenylacetonitrile, which is applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., and can solve problems such as difficult to achieve blue light emission
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Embodiment 1
[0032]
[0033] Add 703mg of carbazole and 25mL of N,N-dimethylformamide (DMF) into a three-necked flask with a stirring bar, gradually add 5mL of DMF solution containing 150mg of NaH at room temperature, stir and react for 30min, then add 193mg of NaH Fluorophenylacetonitrile DMF solution 5mL, stirred for 3h.
[0034] After the reaction, pour the reaction mixture into 50 mL of ice water, filter the precipitate, use silica gel as the stationary phase, and use a mixed solution of petroleum ether and dichloromethane with a volume ratio of 1 to 3:1 as the eluent, and separate it by column chromatography to obtain Compound CyFbCz yellow solid 327mg, yield 42%.
[0035] figure 1 In the H NMR spectrum, the chemical shifts of 7.84-7.59ppm, 7.49-7.28ppm, 7.15-6.99ppm, and 6.65-6.57ppm are aromatic hydrogens on the carbazole ring. Since the product is a symmetrical structure, the carbazole ring has a total of There are four groups of hydrogens, and the number of hydrogens in each ...
Embodiment 2
[0043]
[0044] Add 824 mg of phenoxazine and 30 mL of DMF into a three-neck flask with a stirring bar, gradually add 5 mL of DMF solution containing 170 mg of NaH at room temperature, stir for 40 min, then add 5 mL of DMF solution containing 193 mg of pentafluorophenylacetonitrile, and stir for 4.5 h.
[0045] After the reaction, pour the reaction mixture into 40 mL of ice water, filter the precipitate, use silica gel as the stationary phase, and use a mixed solution of petroleum ether and dichloromethane with a volume ratio of 1 to 4:1 as the eluent, and separate it by column chromatography to obtain Compound CyFbPOZ yellow solid 313mg, yield 37%.
[0046] 1 H NMR (500 MHz, DMSO- d 6 ) δ (ppm): 7.33-7.29 (m, 8H), 6.98 (d, J = 7.2Hz, 4H), 6.95-6.91 (m, 4H), 6.75-6.70 (m, 8H), 6.75-6.71 (m, 8H).
[0047] The compound CyFbPOZ prepared in this example was doped in the mCP host material by vacuum evaporation to form a thin film, and the transient fluorescence decay curve...
Embodiment 3
[0050]
[0051] Add 856 mg of phenothiazine and 35 mL of DMF into a three-neck flask with a stirring bar, gradually add 7 mL of DMF solution containing 190 mg of NaH at room temperature, stir for 1 hour, then add 5 mL of DMF solution containing 193 mg of pentafluorophenylacetonitrile, and stir for 7 hours .
[0052] After the reaction, pour the reaction mixture into 60 mL of ice water, filter the precipitate, use silica gel as the stationary phase, and use a mixed solution of petroleum ether and methylene chloride with a volume ratio of 1 to 2:1 as the eluent. After separation by column chromatography, Obtained compound CyFbPTZ brown yellow solid 409mg, yield 45%.
[0053] 1 H NMR (500 MHz, DMSO- d 6 ) δ (ppm): 7.69-7.63 (m, 8H), 7.55-7.52 (m,4H), 7.50-7.46 (m, 4H), 7.41 (d, J = 7.2 Hz, 4H), 7.36-7.33 (m, 4H), 7.29-7.25 (m, 8H).
[0054] The compound CyFbPTZ prepared in this example is doped into the mCP host material to make a thin film, and the transient fluorescenc...
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