Tetravalent metal platinum complex containing tetradentate ligand, preparation method, application and device
A tetravalent metal, tetradentate ligand technology, applied in electric solid devices, semiconductor devices, platinum-based organic compounds, etc., can solve the problem of tetravalent cyclic metal platinum (IV) metal complex phosphorescent materials. The research report is rare and the stability is poor. and other problems to achieve the effect of improved stability, high stability and high material stability
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Embodiment 1
[0219] The tetravalent ring metal platinum (IV) complex Pt37 containing a tetradentate ligand provided by the present invention can be synthesized as follows:
[0220]
[0221] Synthesis of intermediate 2-OMe: Add 4-bromo-1-(3-methoxybenzene)-1-hydrogen-pyrazole 1 (1200 mg, 4.74 mmol, 1.00 eq. ), 2,4,6-trimethylphenylboronic acid (1166mg, 7.11mmol, 1.50 equivalents), Pd 2 (dba) 3 (82mg, 0.09mmol, 0.02eq), tripotassium phosphate (3018mg, 14.22mmol, 3.00eq), S-Phos (156mg, 0.38mmol, 0.08eq). The nitrogen was purged three times, then, toluene (20 mL) was added. Then nitrogen was bubbled for 20 minutes, and the reaction mixture was stirred at 110° C. for 3 days. After cooling, the solvent was distilled off under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography, eluent (petroleum ether / ethyl acetate=20:1-10:1), to obtain 2-OMe, 1354 mg of yellow solid, yield 97%.
[0222] 1 H NMR (500MHz, DMSO-d 6 ):δ2.13(s,6H),2....
Embodiment 2
[0231] The tetravalent ring metal platinum (IV) complex Pt47 containing a tetradentate ligand provided by the present invention can be synthesized as follows:
[0232]
[0233] Synthesis of intermediate compound 3: Add 3,5-dimethyl-4-bromopyrazole (5250mg, 30.00mmol, 1.00 equivalents), cuprous iodide to a dry three-necked flask with a reflux condenser and a magnetic rotor in sequence (572mg, 3.00mmol, 0.10equivalent), L-proline (690mg, 6.00mmol, 0.20equivalent), potassium carbonate (8280mg, 60.00mmol, 2.00equivalent), nitrogen was replaced three times, and then m-iodoanisole (10500mg , 45.00mmol, 1.50eq) and redistilled dimethylsulfoxide (10mL). The reaction mixture was stirred at 120° C. for 2 days, and monitored by TLC until the reaction of the raw material 4-bromopyrazole was completed. Add water (100mL) to quench the reaction, filter, 50mL of ethyl acetate fully wash the insoluble matter, separate the organic phase in the mother liquor, dry over anhydrous sodium sulfat...
Embodiment 3
[0245] The tetravalent ring metal platinum (IV) complex Pt52 containing a tetradentate ligand provided by the present invention can be synthesized as follows:
[0246]
[0247] Synthesis of intermediate 5-OMe: Add 4-bromo-1-(3-methoxybenzene)-3,5-dimethyl-1 hydrogen-pyrazole 3 ( 4.50g, 16.01mmol, 1.00eq), 2,4,6-trimethylphenylboronic acid (5.25g, 32.02mmol, 2.00eq), Pd 2 (dba) 3(0.29g, 0.32mmol, 0.02eq), tripotassium phosphate (10.20g, 48.03mol, 3.00eq), S-Phos (0.53g, 0.60mmol, 0.08eq) were purged of nitrogen three times, then toluene (100mL) was added. Then nitrogen was bubbled for 20 minutes, and the reaction mixture was stirred at 110° C. for 3 days. Cool, add water (100 mL), extract with ethyl acetate (50 mL×3), combine organic phases, dry over anhydrous sodium sulfate, filter, and distill off the solvent under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography with eluent (petroleum ether / ethyl acetate=20:1-1...
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