Star-type fluorescent molecule and preparation method and application thereof
A technology of fluorescent molecules and carbazoles, applied in the field of star-shaped fluorescent molecules and their preparation, can solve the problems of low utilization rate of materials, expensive equipment and high prices of OLED products, etc., and can enhance the fluorescence of materials and improve the photoelectric efficiency. , the effect of improving fluorescence quantum yield and carrier transport capacity
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[0052] 1. Preparation of monomer
[0053] Preparation of 1-nitropyrene:
[0054] Under an argon atmosphere, pyrene (12.0 g, 50 mmol) and 100 mL of dichloromethane solvent were added to the reaction flask, and a mixture of 25 mL of acetic acid and 25 mL of fuming nitric acid was added dropwise at a temperature of 0° C., and reacted for 24 hours. After stopping the reaction, add sodium hydroxide aqueous solution to pH greater than 7, wash with water to neutrality, extract with dichloromethane, separate the organic phase, concentrate, purify by silica gel column chromatography, the mixed solvent of sherwood oil / dichloromethane ( 5 / 1, v / v) as the eluent to obtain a pale yellow solid. 1 H NMR, 13 CNMR, MS and elemental analysis results show that the obtained compound is the target product, and the chemical reaction equation of the preparation process is as follows:
[0055]
[0056] Preparation of 1H-phenanthrenol [1,10,9,8-cdefg]carbazole:
[0057] Under an argon atmosphere...
Embodiment 1
[0075] Example 1: Preparation of star-shaped fluorescent molecule H1
[0076] Under argon atmosphere, in a 100mL three-necked flask, add tris(7-bromo-9,9-dioctyl-9H-fluorenyl-2-yl)amine (1.70g, 1.2mol), 2-(4, 4,5,5-tetramethyl-1,3,2-dioxaborolane-diyl)-9,9-dioctylfluorene (2.48g, 4.8mmol), aqueous solution of potassium carbonate (2mol / L , 1.32g / 4.8mL deionized water, 9.6mmol), tetrabutylammonium bromide (19mg, 0.06mmol), tetrakistriphenylphosphine palladium (69mg, 0.06mmol) and 50mL toluene. Heat and stir to 85°C, react for 12h. After stopping the reaction, the solvent was concentrated, and the crude product was purified by column chromatography, using a mixed solvent of petroleum ether and dichloromethane (3 / 1, v / v) as the eluent to obtain a beige solid. 1 H NMR, 13 CNMR, MS and elemental analysis results show that the obtained compound is the target product H1, and the chemical reaction equation of the preparation process is as follows:
[0077]
[0078] The thermogra...
Embodiment 2
[0080] Example 2: Preparation of star-shaped fluorescent molecule H2
[0081] The chemical reaction equation of the preparation process is as follows:
[0082]
[0083] (1) 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-diyl)-9,9,9',9'-tetraoctyl-2, Synthesis of 2'-bisfluorene
[0084] Under an argon atmosphere, 2-bromo-9,9-dioctylfluorene (2.34 g, 5.0 mmol), 2,7-bis(4,4,5,5-tetramethyl- 1,3,2-dioxaborinane-diyl)-9,9-dioctylfluorene (4.82g, 7.5mmol), and tetrabutylammonium bromide (0.16g, 0.50mmol), and added rapidly Catalyst tetrakistriphenylphosphine palladium (0.58g, 0.50mmol) and 50wt% K 2 CO 3 Aqueous solution (6.9g / 7.0mL deionized water, 50mmol), react overnight at 80°C. After the reaction was completed, the organic phase was separated and concentrated. The crude product was purified by column chromatography, using petroleum ether / dichloromethane (5 / 1) (volume ratio) as eluent. Finally, 5.57 g of white solid was obtained, the yield was 65%. 1 H NMR, 13 CNMR, MS a...
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