Boron-containing organic compound as OLED doping material and organic light-emitting device
A technology of organic compounds and doping materials, applied in the field of semiconductors, can solve problems such as narrowing the luminescence peak shape, and achieve the effects of improving the life of the device, improving the efficiency of the device, and inhibiting the decomposition of evaporation.
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Embodiment 1
[0068] Example 1 Synthesis of Compound 1
[0069]
[0070] (1) Add 0.01 mol of raw material I-1, 0.022 mol n-bromide, then add 100 ml of dimethylformamide, heat it to 60 ° C, stir reflow for 12 hours, and use TLC observed the reaction until the reaction was complete. Naturally, it was cooled to room temperature, and 100 ml of 1 mol / lnaOH solution was stirred, and then dried, and then dried to give intermediate I-1.
[0071] (2) Under three bottles, under a nitrogen gas protection, 0.01 mol intermediate I-1, 0.022 mol raw material II-2, 150 ml toluene is mixed, then add 5 × 10 -5 MOL PD 2 (DBA) 3 , 5 × 10 -5 MOL P (T-bu) 3 Heat until 110 ° C, refluxed for 24 hours, and the reaction was observed using TLC until the reaction was complete. Naturally, it was cooled to room temperature, filtered, filtrate, vapor-free distillate, azogenic silica gel column, to obtain intermediate II-1.
[0072] (3) Under a nitrogen atmosphere, 0.001 mol intermediate II-1 was added to the three flasks...
Embodiment 2-4
[0074] The synthesis method of the compound in Example 2-4 was similar to that of Example 1, which distinguishes the use of the raw materials, and the structural formula of the raw material, intermediate, and product, the test results are also shown in the table below. Listed.
[0075] Table 1-1
[0076]
[0077]
[0078] Intermediate I-5 synthesis
[0079]
[0080] (1) Add 0.01 mol raw material A-1, 0.012mol raw material A-2, 0.02mol, potassium carbonate, 5 × 10 -5 MOL PD (PPH 3 ) 4 Then, 250 mL of toluene and 50 mL of ethanol were added, and stirred back for 4 hours, and the reaction was observed using TLC until the reaction was complete. Naturally, it was cooled to room temperature, filtered, and the filtrate was evaporated to no distortion. The resulting substance was purified by silica gel columns (petroleum ether as eluent) to obtain intermediate A-1;
[0081] (2) Under nitrogen protection, 0.02 mol intermediate A-1 was added to the three flasks, dissolved with 100 ml ...
Embodiment 13
[0088] Example 13 Synthesis of Compound 2
[0089]
[0090] (1) In an argon atmosphere, 0.15 mol of raw materials II-2 was added to the double neck round bottom flask equipped with the reflux condenser. 0.4 mol of cesium carbonate and 300 ml DMF were added to give a suspension, the suspension at room temperature for 30 minutes. Subsequently, 0.7 mol raw material I-13 was poured once, and the reaction mixture was stirred at 150 ° C for 12 hours. The mixture was diluted with water, and crude crude product was recrystallized with hot ethanol, and the intermediate II-13 was obtained.
[0091] (2) Nitrogen atmosphere, 0.001 mol intermediate II-13 was added to three flasks, then 10 ml of 1,2,4-trichlorobenzene was added to dissolve it, and 0.003 mol Bi was added. 3 And 0.002mol pH 3 B and then the post-heating to 200 ° C for 12 hours. After the end of the reaction, it was lowered to room temperature, and then 100 ml of pH = 7 was added to the reaction mixture, then the aqueous layer w...
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