Organic luminescent material with thermally induced delayed fluorescence performance, preparation method and application thereof
A technology of thermally induced delayed fluorescence and luminescent materials, which is applied in the fields of luminescent materials, fluorescence/phosphorescence, and material analysis through optical means. High fluorescence quantum yield, good solubility effect
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Embodiment 1
[0060] (1) Synthesis of intermediate 2,6-dibromo-cyclofluorenone dithiophene, the synthetic route is as follows:
[0061]
[0062] Add 3,3-dibromo-2,2-bithiophene (2.55g, 7.87mmol) into a 200ml Zelanque bottle, pump it through three times, add 50ml of ether, put it into a low-temperature box that has been precooled to -78°C, and slowly add n-Butyllithium (8.04ml, 18.89 mmol), after 2 hours of reaction, 100ml of dimethylcarbamoyl chloride was added, stirred overnight to room temperature, quenched with ice water, extracted with ether, dried over anhydrous sodium sulfate, separated by silica gel column chromatography, Chloromethane / petroleum ether (v:v)=1:1 is used as eluent, the product is dark purple powder, yield: 68%, elemental analysis theoretical value C 9 h 4 OS 2 (%): C 56.23, H 2.10, O 8.32. Found values: C 56.28, H 2.08, O 8.28;
[0063] Add the dark purple powder cyclofluorenone dithiophene and N-bromosuccinimide obtained above with a molar ratio of 1:2 into an o...
Embodiment 2
[0074]
[0075] Select 2,6-dibromo-cyclofluorenone dithiophene (2.50g, 7.14mmol), carbazole (1.19g, 7.14mmol), cuprous iodide (0.10g, 0.53mmol), potassium carbonate (2.20g, 15.9 mmol), 18-crown-6 (0.14g, 0.54 mmol), 3ml o-dichlorobenzene, put into a 150ml round bottom flask, reflux at 190°C for 48 hours, quenched with 10ml saturated aqueous sodium chloride solution, extracted with dichloromethane, no Dry over sodium sulfate, separate by silica gel column chromatography, dichloromethane / petroleum ether (v:v) = 1:1 as eluent, yield: 68%, elemental analysis theoretical value C 21 h 10 BrNOS 2 (%): C 57.81, H 2.31, N 3.21. Found values: C 57.78, H 2.37, N 3.32.
Embodiment 3
[0077]
[0078] Putting 2,6-dibromo-cyclofluorenone dithiophene and carbazole into the reaction at a molar ratio of 1:2, a double-sided carbazole-substituted cyclofluorenone dithiophene can be synthesized with a yield of 86% and a theoretical value of C 33 h 18 N 2 OS 2 (%): C 75.84, H 3.47, N 5.36. Found values: C 75.78, H 3.52, N 5.43.
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