Naphthoquinone organic electroluminescent material, and preparation method and application thereof
A technology of luminescence and naphthoquinones, applied in the field of organic electroluminescent materials, to achieve the effects of reducing efficiency roll-off, improving exciton utilization rate and high fluorescence radiation efficiency, improving power efficiency and external quantum efficiency
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Embodiment 1
[0053] Example 1 Preparation of Compound 2
[0054]
[0055] In a 250ml three-neck flask, under a nitrogen atmosphere, add 0.011mol (3.47g) of 2,7 dibromonaphthoquinone, 0.01mol (2.58g) of compound M1, 0.03mol (2.88g) of sodium tert-butoxide, 10- 4mol (0.073g) Pd (dppf) Cl2, 180ml toluene, heated to reflux for 10 hours, sampled and spotted, the reaction was complete; naturally cooled, filtered, and the filtrate was rotary evaporated, and the filtrate was subjected to column chromatography to obtain 3.06 g of the target product with a purity of 99.3 %, yield 62%;
[0056] Take another 250mL three-necked flask, and add 0.006mol (2.96g) of intermediate A1, 0.0072mol (1.24g) of 1-naphthaleneboronic acid, 0.12mol (1.66g) of potassium carbonate, 6×10-5mol ( 0.072g) Pd (PPh3) 4, 100mL toluene, 60mL water, heat and reflux for 8h, take a sample and point the plate, and the reaction is complete; naturally cool, filter, separate the filtrate, wash the organic phase with water to neut...
Embodiment 2
[0059] Example 2 Preparation of Compound 9
[0060]
[0061] In a 250ml three-neck flask, under an atmosphere of nitrogen gas, add 0.011mol (3.47g) 2,7-dibromonaphthoquinone, 0.01mol (4.19g) compound M2, 0.3mol (4.15g) potassium carbonate, 10-4mol (0.0224g) palladium acetate, 10-4mol (0.0202g) tert-butylphosphine, 100mL toluene, 60mL water, heat and reflux for 10 hours, take a sample and spot the plate, and the reaction is complete; naturally cool, filter, separate the filtrate, and wash the organic phase To neutrality, the organic phase was collected by rotary evaporation, and the organic phase was subjected to column chromatography to obtain 3.66 g of the target product with a purity of 99.1% and a yield of 60%;
[0062] Take another 250mL three-necked flask, add 0.006mol (3.66g) of intermediate A2, 1.2×10-4Pd(dppf)Cl2, 150mL tetrahydrofuran under nitrogen atmosphere, heat to 50-55°C and keep warm, dropwise add 0.024mol (3.54g) Grignard reagent of bromopropane (it can be...
Embodiment 3
[0065] The preparation of embodiment 3 compound 11
[0066]
[0067] 250ml there-necked flask, under the atmosphere of feeding nitrogen, add 0.011mol (3.47g) 2,3-dibromonaphthoquinone, 0.01mol (4.39g) compound M4, 0.3mol (4.15g) potassium carbonate, 10-4mol (0.0224g) palladium acetate, 10-4mol (0.0202g) tert-butylphosphine, 100mL toluene, 60mL water, heat and reflux for 12 hours, take a sample point plate, and the reaction is complete; naturally cool, filter, separate the filtrate, and wash the organic phase To neutrality, the organic phase was collected by rotary evaporation, and the organic phase was subjected to column chromatography to obtain intermediate A4 with a purity of 99.2% and a yield of 51%;
[0068] Take another 250ml three-necked flask, and add 0.01mol (6.30g) of intermediate A, 0.012mol (1.46g) of phenylboronic acid, 0.3mol (4.15g) of potassium carbonate, 10-4mol (0.12g) of )Pd(PPh3) 4, 100mL toluene, 60mL water, heat and reflux for 8 hours, take a sample p...
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