Blue-light conjugated polymer based on naphtho-8-S,S-dioxide dibenzothiophene units as well as preparation method and application of blue-light conjugated polymer
A technology of dioxydibenzothiophene and conjugated polymer is applied in the field of blue light conjugated polymer and its preparation to achieve the effects of improving device efficiency, reducing conjugation and high fluorescence quantum yield
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Embodiment 1
[0055] Methyl 1-Bromodinaphthoate
[0056] Under an argon atmosphere, 1-bromo-2-naphthoic acid (10g, 39.83mmol) was added to a two-neck flask, then 100mL of methanol was added, and then concentrated sulfuric acid (39.06mg, 398.29umol) was added dropwise, heated to 110°C, Reaction 18h. 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 white solid crude product was obtained, which was purified by silica gel column chromatography (petroleum ether / dichloromethane=3 / 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 with a yield of 85%. . 1 H NMR, 13 CNMR, MS and elemental analysis results show that the obtained compound is the target product, and the chemical reaction equation is as follows:
[0057]
Embodiment 2
[0059] Preparation of 2-bromothiofluorene
[0060] Under an argon atmosphere, add thiofluorene (20g, 108.54mmol) into a 250ml two-necked bottle, then add 100ml of chloroform to dissolve completely, add 0.5g (275mg, 1.09) of iodine, and dropwise Add liquid bromine (18.16g, 138.80mmol), the reaction solution was stirred under ice bath for 2 hours, then stirred at room temperature for 2 hours, added saturated sodium bisulfite to quench the liquid bromine, the reaction mixture was poured into water, washed with acetic acid Extracted with ethyl ester, the organic layer was washed completely with brine, and dried over anhydrous magnesium sulfate. After the solution was concentrated, a crude white solid was obtained, which was then recrystallized from chloroform with a yield of 85%. 1 H NMR, 13 CNMR, MS and elemental analysis results show that the obtained compound is the target product, and the chemical reaction equation is as follows:
[0061]
Embodiment 3
[0063] 2-diborate thiofluorene
[0064] Under an argon atmosphere, 2-bromothiofluorene (10 g, 29.24 mmol) was dissolved in 180 mL of refined tetrahydrofuran (THF), and 1.6 mol L of -1 18mL of n-butyllithium, reacted for 2 hours, then quickly added 25mL of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane, at -78℃ The reaction was continued for 1 hour, and the temperature was slowly 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 and GC-MASS tests show that it is the target product, and the che...
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