Electroluminescent compounds comprising fluorene group and organic electroluminescent device using the same
A compound, electroluminescence technology, applied in electroluminescence light sources, organic semiconductor devices, electric solid devices, etc., can solve problems such as difficulty, pure blue does not meet the requirements, etc.
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Synthetic example 1
[0048] [Synthesis Example 1] Preparation of DIF-1 (compound 120)
[0049]
[0050] Preparation of compound (112)
[0051] Compound (111), 1,4-dibromo-p-xylene (200g, 0.76mol) and phenylboronic acid (204g, 1.67mol), Pd(OAc) 2 (0.34g, 1.52mmol), potassium carbonate (524g, 3.79mol) and n-Bu 4 NBr (490 g, 1.51 mol) was suspended in 1.9 L of distilled water, and the suspension was stirred at 70° C. for 24 hours. After the reaction was completed, 2 L of distilled water was added to the reaction mixture, and the resulting solid was filtered off under reduced pressure to obtain compound (112) (196 g, 0.76 mol) as a gray solid.
[0052] Preparation of compound (113)
[0053] Compound (112) (196 g, 0.76 mol) was dissolved in pyridine (1.23 L, 15.17 mol) and H 2 In O (2L), in the reaction solution, slowly add KMnO in 10 batches 4 (420 g, 2.66 mol) and the resulting mixture was heated at reflux for 48 hours.
[0054] Distilled water (5 L, 50° C.) was added, and the solid by-p...
Synthetic example 2
[0073] [Synthesis Example 2] Preparation of DSF-1 (compound 125)
[0074]
[0075] Preparation of Compounds (121) and (122)
[0076] Diethyl ether (5 mL) was added to 2-bromobiphenyl (6.27 g, 26.9 mmol) and magnesium powder (0.68 g, 28.2 mmol), and the mixture was heated to reflux for 3 hours with stirring. Diethyl ether solvent (5 mL) was added to 2,7-bromofluorenone (10 g, 29.6 mmol), and after stirring, the mixture was slowly added to the reaction mixture. After stirring at 25°C for 24 hours, saturated aqueous ammonium chloride solution (50 mL) was placed in an ice bath. After stirring for 1 hour, it was filtered, washed with 100 mL of distilled water, and filtered under reduced pressure to obtain crude compound (121), which was added to glacial acetic acid (40 mL) and heated to reflux for 2 hours. A 30% hydrochloric acid solution (40 mL) was slowly added to the reaction solution to form a solid, which was then filtered under reduced pressure, washed with 100 mL of...
Synthetic example 3
[0085] [Synthesis Example 3] Preparation of DPF-1 (compound 130)
[0086]
[0087] Preparation of Compounds (126) and (127)
[0088] Diethyl ether (50 mL) was added to magnesium (4.9 g, 0.20 mol), and a solution of bromobenzene (31.4 g, 0.20 mmol) dissolved in 150 mL of diethyl ether was slowly added dropwise thereto. After heating the reaction mixture under reflux for 3 hours, a solution of 2,7-dibromofluorene (33.8 g, 0.10 mol) dissolved in 40 mL diethyl ether was slowly added dropwise to the reaction mixture, and then heated to reflux for 12 hours.
[0089] After completing the reaction, the resulting precipitate was filtered under reduced pressure to obtain compound (126) (41.5 g, 0.10 mmol). Compound (126) was dissolved in 145 mL of benzene, and trifluoromethanesulfonic acid (45 mL) was slowly added dropwise thereto while slowly raising the temperature. After the mixture was stirred at 100°C for 30 minutes, the reaction solution was added to ice water to generate...
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