Bipolar polymer luminescent material based on diarylamine group as well as preparation method and application thereof
A diarylamine-based, luminescent material technology, applied in luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., to achieve the effects of improving device efficiency, enriching optical and electrical properties, and high fluorescence quantum yield
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Embodiment 1
[0060] Preparation of 2-bromofluorene
[0061]In a 250mL three-necked flask, add fluorene (16.6g, 0.1mol), iron powder (88mg, 1.57mmol), and 100mL of chloroform; cool in an ice-water bath, add bromine (17.6g, 0.1mol) / chloroform mixed solution dropwise 35mL, the temperature in the bottle does not exceed 5°C when adding dropwise. Reacted for 16 hours, filtered and recrystallized from chloroform to obtain 19.3 g of white solid with a yield of 84%. 1 H NMR, 13 CNMR, MS and elemental analysis results show that the obtained compound is the target product, and its chemical reaction equation is as follows:
[0062]
Embodiment 2
[0064] Preparation of 2-bromo-9,9-dioctylfluorene
[0065] Add 2-bromofluorene (7.4g, 0.03mol), benzyltriethylammonium chloride (0.07g, 0.3mmol), dimethyl sulfoxide 90mL, 45mL sodium hydroxide aqueous solution (50wt%) in the three-necked flask, Stir at room temperature to form a suspension; add 1-bromo-n-octane (12.5 g, 65 mmol) dropwise, and continue stirring for 3 hours, then extract with ether; wash the ether phase with saturated aqueous sodium chloride and dry over anhydrous magnesium sulfate. The solvent was evaporated, and the product was purified by column chromatography using petroleum ether as the eluent to obtain a white solid. 1 H NMR, 13 CNMR, MS and elemental analysis results show that the obtained compound is the target product, and its chemical reaction equation is as follows:
[0066]
Embodiment 3
[0068] Preparation of 2-boronate-9,9-dioctylfluorene
[0069] Under an argon atmosphere, 2-bromo-9,9-dioctylfluorene (5 g, 10.65 mmol) was dissolved in 180 mL of refined tetrahydrofuran (THF), and 1.6 mol.L was gradually added dropwise at -78 ° C -1 28mL of n-butyllithium, reacted for 2 hours, then added 25mL of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane, at -78°C The reaction was continued for 1 hour, and the temperature was raised to room temperature for 24 hours. The reaction mixture was poured into water, extracted with ethyl acetate, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. After the solution was concentrated, a light yellow viscous crude product was obtained, which was purified by silica gel column chromatography (petroleum ether / ethyl acetate=20 / 1, v / v was selected as the eluent), and the product was placed in the refrigerator for a long time to obtain a white solid, the product rate of 70%. 1 H NMR, 13 CNMR, MS...
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