Thermal activation delayed fluorescence material and preparation method thereof, and organic electroluminescent device
A technology of thermally activated delayed and fluorescent materials, applied in luminescent materials, electric solid-state devices, chemical instruments and methods, etc. The effect of red-shifting the light band and improving the light yield of the device
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[0071] Another embodiment of the present invention provides a method for preparing a thermally activated delayed fluorescent material having formula (I-1), the method comprising the following steps S11-S13.
[0072] S11. Reacting 9,9-dimethyl-9h-thioxanthene with N-bromosuccinimide (NBS) in the dark to generate a compound of formula (a), the reaction formula is:
[0073]
[0074] In one embodiment, 9,9-dimethyl-9h-thioxanthene and N-bromosuccinimide (NBS) are fed in a molar ratio of 1:(2~2.5), protected from light The reaction produces a compound of formula (a).
[0075] Specifically, according to the molar ratio of 9,9-dimethyl-9h-thioxanthene to N-bromosuccinimide (NBS) is 1:(2~2.5), the 9,9-Dimethyl-9h-thioxanthene was mixed with NBS, and reacted at room temperature in the dark for 10-14 hours.
[0076] S12, the compound of formula (a) is oxidized to generate the compound of formula (b-1), and the reaction formula is:
[0077]
[0078] In one embodiment, the oxidan...
Embodiment 1
[0128] Embodiment 1 synthetic formula (M11) compound
[0129] 1) Synthesis of 9,9-dimethyl-9h-thioxanthene
[0130] Add 15mmol of sulfur-containing heterocyclic compound dibenzothiopyran into a 50mL two-necked flask, add a stirring magnet, and perform a vacuum-exchange operation for nitrogen. Repeat three times to make the reaction bottle in a nitrogen atmosphere, and add 30mL of tetrahydrofuran (THF) , stirred at room temperature to dissolve the dibenzothiopyran solid, then lowered the temperature to -78°C, added 32mmol n-butyllithium (n-BuLi), and carried out a constant temperature reaction at -78°C in a low-temperature reactor for 2h, and then gradually Add 32mmol methyl bromide dropwise, continue to stir for 1h, then return to room temperature and react for 24h. After the reaction is completed, use a silica gel chromatography column for separation and purification, use n-hexane / dichloromethane as the eluent, rotary evaporate, remove the solvent to collect the product 9,9-...
Embodiment 2
[0139] Embodiment 2 synthetic formula (M12) compound
[0140] Embodiment 2 is basically the same as Embodiment 1, the difference lies in step 4), specifically:
[0141] The reaction formula of synthetic formula (M12) compound is:
[0142]
[0143] Add 30mmol sodium hydride (NaH) into a 50mL two-necked bottle, add 30ml of anhydrous N,N-dimethylformamide (DMF), add a stirring magnet to stir and dissolve, and then add the amine electron of formula (c-2) 15 mmol of the donor was stirred for 30 min; then 7.5 mmol of the compound of formula (b) obtained in step 3) was dissolved in anhydrous DMF, and then added dropwise to the reaction liquid, and reacted at 100°C for 2 h. After the reaction is over, add water to the solution to end the reaction, then filter and dry to obtain a crude product. After the crude product was further purified with a silica gel chromatographic column, n-hexane / ethyl acetate was used as the eluent, the solvent was removed by rotary evaporation to collec...
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