Organic compound based on triazine and quinoxaline and application thereof to OLED (organic light emitting diode) device
A technology of electroluminescent devices and organic compounds, which is applied to organic compounds based on triazine and quinoxaline, and the application field of organic electroluminescent devices, which can solve the problems affecting the angular distribution of OLED radiation spectrum and complex manufacturing process, etc. Achieve the effect of avoiding free rotation, high density and high Tg temperature
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Embodiment 1
[0050] Embodiment 1: the synthesis of intermediate I
[0051]
[0052] Under nitrogen atmosphere, weigh The bromide was dissolved in tetrahydrofuran (THF), and then bis(pinacolyl)diboron, (1,1'-bis(diphenylphosphino)ferrocene)dichloropalladium(II) and potassium acetate were added, The mixture is stirred, and the mixed solution of the above reactants is heated to reflux at a reaction temperature of 70-90° C. for 5-10 hours; after the reaction is completed, water is added to cool, and the mixture is filtered and dried in a vacuum oven. The obtained residue was separated and purified by silica gel column to obtain pinacol borate;
[0053]
[0054] Under a nitrogen atmosphere, weigh raw material A and dissolve it in N,N-dimethylformamide (DMF), and then and palladium acetate, stir the mixture, then add aqueous potassium phosphate solution, heat the mixed solution of the above reactants to reflux at a reaction temperature of 120-150°C for 5-15 hours; after the reaction ...
Embodiment 2
[0071] Embodiment 2: intermediate Synthesis
[0072] When R 2 or R 3 When expressed as a structure of general formula (2),
[0073]
[0074] (1) Under a nitrogen atmosphere, weigh 2,3-dibromoquinoxaline and dissolve it in tetrahydrofuran, and then Ar 4 -B(OH) 2 And tetrakis (triphenylphosphine) palladium is added, the mixture is stirred, and then saturated potassium carbonate aqueous solution is added, and the mixed solution of the above reactants is heated and refluxed at a reaction temperature of 70-90°C for 10-20 hours; after the reaction is completed, cool and mix The liquid was extracted with dichloromethane, the extract was dried with anhydrous sodium sulfate, and concentrated under reduced pressure, and the concentrated solid was purified by silica gel column to obtain compound intermediate M;
[0075]
[0076] (2) Under a nitrogen atmosphere, weigh the intermediate M and dissolve it in N,N-dimethylformamide (DMF), then add bis(pinacolyl)diboron, (1,1'-bis(dip...
Embodiment 3
[0100] Embodiment 3: the synthesis of compound 1:
[0101]
[0102] In a 250mL three-necked flask, blow nitrogen gas, add 0.01mol of intermediate A1, 150ml of DMF, 0.03mol of intermediate B1, 0.0002mol of palladium acetate, stir, and then add 0.02mol of K 3 PO 4 The aqueous solution was heated to 150°C, refluxed for 24 hours, sampled and plated, and the reaction was complete. Cool naturally, extract with 200ml of dichloromethane, separate layers, dry the extract with anhydrous sodium sulfate, filter, rotate the filtrate, and purify through a silica gel column to obtain the target product with a HPLC purity of 99.2% and a yield of 64.3%.
[0103] Elemental analysis structure (molecular formula C 59 h 37 N 9 ): theoretical value C, 81.27; H, 4.28; N, 14.46; test value: C, 81.24; H, 4.26; N, 14.45. ESI-MS(m / z)(M + ): The theoretical value is 871.32, and the measured value is 872.01.
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