Pterylene pyridazine octadentate double platinum complex phosphorescent material and preparation method and application thereof
A technology of platinum complexes and phosphorescent materials, applied in luminescent materials, platinum-based organic compounds, platinum-based organic compounds, etc., to achieve the effects of reducing self-quenching, easy purification, and increasing steric hindrance
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Embodiment 1
[0043] Example 1. Preparation of intermediate 9,10-dihydro-9,10-diethylanthracene-11,12-acid anhydride dda
[0044] Anthracene (7.5 g, 42 mmol) and dimethyl butynedioate (DMAD, 7.5 mL, 61 mmol) were put into a reaction flask, reacted at 170 °C for 45 min, and then heated to 180 °C for another 5 min. After the completion of the reaction, the mixture was cooled and recrystallized with methanol to obtain 12.2 g of 9,10-dihydro-9,10-diethylanthracene-11,12-dicarboxylate ddcme as a white solid with a yield of 90%. The above product ddcme was dissolved in sodium hydroxide (4.0 g, 100 mmol), methanol (50 mL, 1237 mmol) and water (15 mL, 833 mmol), refluxed for 1 hour, cooled and placed at -20°C overnight. There are crystals, add water to dissolve, adjust the pH to below 5 with 1 mol / L dilute hydrochloric acid solution, there is precipitation, suction filtration and drying to obtain 10g of white solid 9,10-dihydro-9,10-diethylanthracene- 11,12-Dicarboxylic acid ddca in 89% yield. Th...
Embodiment 2
[0046] Example 2. Preparation of pterene-modified intermediate hydrazide ddah and dichloropyridazine compound ddcp
[0047] Weigh 9,10-dihydro-9,10-diethylanthracene-11,12-acid anhydride dda (6.5 g, 23 mmol) into a reaction flask, pour (20 mL, 350 mmol) glacial acetic acid, and stir to reflux. After the solid was dissolved, hydrazine hydrate (3.5 g, 70 mmol) was added dropwise, and the reaction was carried out at 125° C. for 3 h. Cooling, suction filtration, washing the product with ethanol, and drying to obtain 6 g of pterene-modified intermediate hydrazide ddah with a yield of 90%. Put ddah (6.0g, 21mmol) into the reaction flask, evacuated, and replaced with nitrogen for at least three times, add 1,2-dichloroethane (20mL, 249mmol), add phosphorus oxychloride (16mL, 172mmol), The reaction was carried out at 125°C for 8h. Dry 1,2-dichloroethane and phosphorus oxychloride in vacuum, pour the product into ice water, adjust the pH to neutrality with sodium hydroxide solution, s...
Embodiment 3
[0049] Example 3. Preparation of phenylpyridazine dcp modified by ligand pterene
[0050] Pterylene-modified dichloropyridazine ddcp (1.71 g, 5 mmol), phenylboronic acid (0.49 g, 4 mmol), potassium carbonate (1.38 g, 10 mmol), PdCl 2 (dppf) (73 mg, 0.1 mmol) was put into the reaction flask, evacuated, and replaced with nitrogen for at least three times; 6 ml of tetrahydrofuran solution and 4 ml of water after deoxygenation with nitrogen gas were added, and the reaction was carried out at 80° C. for 24 h. After the reaction, it was extracted with dichloromethane, dried by adding anhydrous sodium sulfate, filtered with suction, and subjected to column chromatography with V PE :V EA =5:1 developing solvent chromatographic separation to obtain 1.06 g of white solid with a yield of 72%. 1 H NMR (400MHz, CDCl 3 )δ7.76–7.54(m,7H),7.44(d,J=6.4Hz,2H),7.13(p,J=7.3Hz,4H),5.95(s,1H),5.83(s,1H).
[0051]
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