Quinoxalin derivative and organic LED (Light-Emitting Diode) containing same
A derivative, quinoxaline technology, applied in the field of quinoxaline derivatives, can solve problems such as poor thermal stability, poor carrier mobility, and low current density
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Embodiment 1
[0027] Compound C2 Synthesis
[0028]
[0029] Put benzothiadiazole (compound 1, 13.6g, 100mmol) into a 1,000mL round-bottom bottle, add 48% HBr aqueous solution (300mL), heat to reflux, and then slowly drop Bromine (15.4mL , 300mmol), react overnight. After the reaction was quenched with aqueous sodium thiosulfate solution, the solid was filtered and washed with acetone to obtain a pale earth-colored solid product (compound 2, 25.3 g, yield 86%).
[0030] Compound 2 (2.94g, 10mmol) was put into a 250mL round bottom bottle, ethanol (150mL) and THF (50mL) were added, and after stirring for 10 minutes, sodium borohydride (1.51g, 10mmol) was added and heated to reflux. After reacting overnight, the solid was filtered off with filter paper, and the filtrate was pumped dry, followed by extraction with diethyl ether and saturated brine. After collecting the organic layer, remove water with anhydrous magnesium sulfate, and concentrate under reduced pressure to obtain a white sol...
Embodiment 2
[0036] Synthesis of compound C3
[0037]
[0038] Put 2-bromo-fluorene (2-bromo-fluorene) (compound 7, 25g, 2mmol) into a 500mL conical flask, add pyridine (pyridine, 300mL), triton B (benzyltrimethylammonium hydroxide, benzyltrimethyl ammonium hydroxide, 5mL), followed by high-pressure oxygen. After reacting for 6 hours, acetic acid (200 mL) was added to quench the reaction, and a golden yellow solid (compound 8, 21.7 g, 80%) was obtained after filtration.
[0039] Take magnesium flakes (1.215g, 50mmol), put them into a 500mL double-neck bottle, connect the condenser tube and the feeding tube, roast in a vacuum to remove water, add a small grain of iodine, and add 50mL of dehydrated THF to the feeding tube and 4-bromotoluene (6.15mL, 100mmol), slowly drop into the reaction flask. After dropping, heat to reflux. After the magnesium flakes completely disappear, dissolve compound 8 (6.4g, 25.0mmol) in 150mL THF, add it to the feeding tube, and slowly drop it into the reaction...
Embodiment 3
[0045] Synthesis of compound C4
[0046]
[0047] Take compound 12 (4.4g, 20mmol) and put it into a 250mL double-neck flask, add N-methyl-pyrrolidinone (N-methyl-pyrrolidinone, NMP) (50mL) and compound 11 (2.1mL, 20mmol) respectively, and heat to 100 ℃. After 1 hour, it was cooled to room temperature, basified to pH 8-9 with aqueous ammonia, filtered and washed with water several times to obtain a white solid (compound 13, 4.1 g, 72%).
[0048] Compound 13 (3.3 g, 11.4 mmol) was put into a 250 mL double-necked flask, anhydrous tetrahydrofuran (100 mL) was added, and the temperature was lowered to -78°C. Inject n-butyllithium reagent (1.6M, 10.7mL, 17.1mmol) at -78°C and react for 0.5 hours, then add 2-isopropoxy-4,4,5,5-tetra Methyl-1,3,2-dioxaborolane (2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 3.5 mL, 17.1 mmol). Slowly return the reaction to room temperature. After reacting at room temperature for 12 hours, extract with ethyl acetate and saturated saline so...
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