Tetradentate cyclometalated platinum complex containing 6-substituted carbazole and preparation method and application thereof
A technology of complexes and metal platinum, which is applied in the direction of platinum group organic compounds, platinum organic compounds, and compounds containing elements of group 8/9/10/18 of the periodic table, etc., which can solve low-efficiency emission or absorption, blue light emission Rare materials, poor machining performance and other problems, to achieve the effect of enhancing coordination ability, improving stability and improving thermal stability
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Embodiment 1
[0171] Embodiment 1: the synthesis of compound Pt29:
[0172]
[0173] Add 4-bromo-3,5-dimethylpyrazole (3.5714g, 20mmol, 98%, 1.0eq), phenylboronic acid (2.9552g, 24mmol, 99%, 1.2 equiv), palladium acetate (0.1123 g, 0.5 mmol, 0.025 equiv), ligand S-Phos (0.5027 g, 1.2 mmol, 98%, 0.06 equiv), 1,4-dioxane (60 mL) and potassium carbonate (8.2920g, 60mmol, 3.0eq) in water (20mL). Nitrogen was sparged for 15 minutes, then the reaction vial was placed in a 115°C oil bath. After stirring for 15 hours, the reaction was complete as monitored by TLC. Cool to room temperature and extract with dichloromethane (20 mL×3). All organic phases were combined and dried over anhydrous sodium sulfate. Filtration and concentration, the resulting crude product was separated and purified by flash silica gel column chromatography (eluent: petroleum ether / ethyl acetate = 3 / 1~1 / 2) to obtain 3,5-dimethyl-4-phenyl -1H-imidazole, white solid 3.0773g, yield 89%. 1 H NMR (500MHz, DMSO-d 6 ): δ2.1...
Embodiment 2
[0187] Embodiment 2: the synthesis of compound Pt393:
[0188]
[0189] Add 6-methyl-2-methoxycarbazole (0.3085g, 1.46mmol, 1.0eq), CuCl (0.0044g, 0.044mmol, 99%, 0.03eq) in sequence to a dry three-necked flask with a magnetic rotor and t-BuOLi (0.2367 g, 2.91 mmol, 99%, 2.0 equiv). The nitrogen was replaced three times, and then 2-bromo-4-tert-butylpyridine (0.3737g, 1.75mmol, 1.2eq), 1-methylimidazole (7.0μL, 0.087mmol, 99%, 0.06eq) were added under nitrogen protection and toluene (6 mL). The reaction vial was then placed in a 130°C oil bath. After stirring for 24 hours, the reaction was complete as monitored by TLC. Cool to room temperature, concentrate, and separate and purify the obtained crude product by flash silica gel column chromatography (eluent: petroleum ether / ethyl acetate=15 / 1~10 / 1) to obtain B-OMe-2, light yellow oil 0.4017g, yield 80%, directly put into the next reaction.
[0190] Under nitrogen protection, B-OMe-2 (0.3814 g, 1.1 mmol, 1.0 equiv), AcOH...
Embodiment 3
[0196] Embodiment 3: the synthesis of compound Pt116:
[0197]
[0198] Add 3,5-dimethyl-4-phenyl-1H-imidazole (2.0680 g, 12 mmol, 1.0 equivalents), 1,3-dibromo-5-tert-butyl to a dry three-necked flask with a magnetic rotor in sequence Benzene (7.1513g, 24mmol, 98%, 2.0eq), cuprous iodide (0.2971g, 1.56mmol, 0.13eq), potassium phosphate (5.0945g, 24mmol, 2.0eq) and trans-N,N'- Dimethyl-1,2-cyclohexanediamine (0.4528 g, 3.12 mmol, 98%, 0.26 equiv). The nitrogen was purged three times, followed by the addition of dimethyl sulfoxide (18 mL) under nitrogen protection. The reaction vial was then placed in a 120°C oil bath. After stirring for 5 days, it was cooled to room temperature, filtered through celite, and the insoluble matter was fully washed with ethyl acetate (30 mL×3). The resulting filtrate was washed with brine (20 mL×2), and the aqueous phases were combined and extracted with ethyl acetate (10 mL×2). All organic phases were combined and dried over anhydrous sodi...
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