Truxene-based star-shaped symmetric organic electroluminescence material and preparation method thereof
A technology of electroluminescence and tri-indene, which is applied in the fields of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of inconvenient preparation and mass production, cumbersome synthesis paths, complex structures, etc., to prevent fluorescence quenching, The synthesis process is simple and the effect of reducing molecular stacking
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Embodiment 1
[0044] What is synthesized in this example is an organic electroluminescent material with three polyindene as the main structure, and its molecular formula is C 138 h 132 , whose structural formula is (I–a):
[0045]
[0046] Its synthetic method comprises the following steps:
[0047] Step 1 (see synthesis route 1):
[0048] ①Mix 10g (66.6mmol) of 3-phenylpropionic acid and 100g of polyphosphoric acid (PPA) into a 250mL three-necked flask, gradually raise the temperature to 60-70°C under a nitrogen atmosphere and maintain this temperature for about 45min, then raise the temperature to 160°C ℃, continue to react for 3h, cool to room temperature, pour the reaction solution into 500mL cold water, a brown solid is produced, filter with Buchner funnel, and recrystallize the filter cake with toluene to obtain 2.75g of a light yellow solid with a yield of 36.3%. According to characterization analysis, the product is tripolyindene. 1 H NMR (400MHz, CDCl 3 ):δ[ppm]7.95(d,J=7.2...
Embodiment 2
[0054] What is synthesized in this example is an organic electroluminescent material with three polyindene as the main structure, and its molecular formula is C 150 h 138 S 3 , whose structural formula is (I–b):
[0055]
[0056] Step 1 (see synthesis route 1):
[0057] The synthetic steps involved are exactly the same as Example 1;
[0058] Step 2 (see synthesis route 2):
[0059] ① Weigh 0.64g (0.59mmol) B, 0.27g (2.11mmol) 2-thiophene boronic acid, 100mg Pd(PPh 3 ) 4 Add it to a 100mL SCHLENK tube, pump out the air and introduce nitrogen, and add N 2 Treated THF 25mL, 2M sodium carbonate solution 5mL, gradually warm up to 110°C, and react at this temperature for 24h, cool to room temperature, extract the reaction solution with dichloromethane, collect the organic phase and dry it with anhydrous magnesium sulfate, After concentration, the crude product was purified by thin-layer chromatography, and the mobile phase was petroleum ether. Finally, 0.36 g of a yellow s...
Embodiment 3
[0064] What is synthesized in this example is an organic electroluminescent material with three polyindene as the main structure, and its molecular formula is C 180 h 165 N 3 , whose structural formula is (I–c):
[0065]
[0066] Its synthesis method is the same as in Example 2, the only difference being that the boronic acid used in step 2 is 9-ethyl-9H-carbazol-3-ylboronic acid, and the aryl bridging unit M in the target product has the following structure:
[0067] NMR analysis data: 1 H NMR (400MHz, CDCl 3 ):δ[ppm]8.51-8.48(m,6H),8.30(s,3H),7.98(d,J=8.0Hz,3H),7.90(d,J=7.6Hz,12H),7.82-7.80( m,9H),7.61(d,J=8.8Hz,3H),7.53(d,J=8.4Hz,3H),7.42-7.38(m,12H),7.18-7.10(m,12H),6.86(d ,J=7.6Hz,6H),6.75(d,J=7.6Hz,3H),4.43-4.41(m,6H),3.11-3.06(m,6H),2.28-2.21(m,6H),1.48( t,J=7.2Hz,9H),1.01-0.92(m,36H),0.66-0.63(m,30H); 13 C NMR (100MHz, CDCl 3 ):δ[ppm]154.38,149.42,149.16,148.94,144.78,141.90,141.84,141.58,140.30,139.88,139.84,138.99,138.19,132.78,132.24,127.88,127.70,127.59,...
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