Nitrogen-containing heterocyclic organic compounds and their applications
An organic compound and cyclic technology, applied in the field of electroluminescent materials, can solve the problems of device performance and lifespan that need to be improved, and achieve the effects of improving luminous efficiency and lifespan, low roll-off and low manufacturing cost
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Embodiment 1
[0194]
[0195] Synthesis of Intermediate 1-3: Dissolve 1-1 (20.0 g) and 1-2 (43.8 g) in dry DMF, add cesium carbonate (38.46 g), and react at 140° C. for 8 h. After cooling, most of the solvent was distilled off under reduced pressure, the residual reaction solution was washed with water and extracted, the organic phase was evaporated to remove the solvent, and then recrystallized to obtain Intermediate 1-3.
[0196] Synthesis of compound 1: Intermediate 1-3 (10.0 g), Pd (PCy 3 ) 2 Cl 2 (CAS 78655-99-9, 1.2 g), isovaleric acid (1.1 g), and cesium carbonate (10.0 g) were added to 100 ml of dry DMAC, and stirred at 170° C. for 6 h under nitrogen atmosphere. After cooling, most of the solvent was distilled off under reduced pressure, extracted and washed with water for separation, the organic phase was evaporated to remove the solvent, and then recrystallized to obtain compound 1. MS (ASAP): 602.
Embodiment 2
[0198]
[0199] Synthesis of Intermediate 2-3: Intermediates 2-1 (20.0 g), 2-2 (16.6 g), DMAP (3.17 g) were dissolved in dry DMSO and cesium carbonate (33.0 g) was added under nitrogen Heated to 100 ℃ under the atmosphere for 8h. After cooling, most of the solvent was distilled off under reduced pressure. The residual reactant was washed with water and extracted, the organic phase was evaporated to remove the solvent, and then recrystallized to obtain Intermediate 2-3.
[0200] The synthesis of material 2 was referred to the synthesis of material 1 of Example 1, except that 1-3 was replaced by 2-3. MS (ASAP): 588.
Embodiment 3
[0202]
[0203] Synthesis of intermediate 3-2: 3-1 (15.0 g), pinacol biboronate (9.3 g), Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene] palladium dichloride, 1.2g), potassium acetate (4.9g) were added to 1,4-dioxane, under nitrogen atmosphere for 100 ℃ reaction 8h. After cooling, most of the solvent was distilled off under reduced pressure. After the residual reaction solution was washed and extracted with water, the organic phase was rotary evaporated to remove the solvent, and then recrystallized to obtain Intermediate 3-2.
[0204] Synthesis of intermediate 3-4: 3-2 (10.0 g), 3-3 (5.2 g), Pd (PPh 3 ) 4 (Tetrakis(triphenylphosphine)palladium, 0.8 g) and potassium carbonate (4.2 g) were added to 1,4-dioxane, and an appropriate amount of water was added. The reaction was carried out at 100°C for 8h under nitrogen atmosphere. After cooling, most of the solvent was distilled off under reduced pressure. After the residual reaction solution was washed and extracted wi...
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