Luminescent compounds and electroluminescent device using the same
A compound and luminescent technology, applied in the direction of electroluminescent light sources, electrical components, luminescent materials, etc., can solve problems such as limitations
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Synthetic example 1
[0064] [Synthesis Example 1] Synthesis of Compound (301)
[0065]
[0066] Dimethyl sulfoxide (150 mL), 2-bromofluorene (15.0 g, 61 mmol), potassium iodide (KI) (1.0 g, 6 mmol) and potassium hydroxide (15.5 g, 0.3 mol) were mixed, Thereto was added iodomethane (8.7 mL, 139 mmol) at -10°C. After stirring at 30°C for 12 hours, the reaction mixture was poured into distilled water (200 mL), and extracted with dichloromethane (300 mL).
[0067] Magnesium sulfate (MgSO 4 ) was dried, and compound (101) (16 g, 58 mmol) was obtained after distillation under reduced pressure.
[0068] Compound (101) (16 g, 58 mmol), phenylboronic acid (10.6 g, 87 mmol), PdCl 2 (PPh 3 ) 2 (4.1 g, 5.8 mmol), 2M aqueous sodium carbonate solution (150 ml), toluene (300 ml) and ethanol (100 ml), and the mixture was stirred at 100° C. for 12 hours. The reaction mixture was extracted with dichloromethane (200 mL), and the organic layer was washed with distilled water (150 mL), dried over magnesium su...
Synthetic example 2
[0079] [Synthesis Example 2] Synthesis of Compound (302)
[0080]
[0081] 9-Bromoanthracene (20 g, 77 mmol) was dissolved in THF (200 mL), and n-BuLi (2.5M in hexane) (40 mL, 100 mmol) was slowly added thereto at -78°C.
[0082] After stirring for 30 minutes, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (31.7 ml, 155 Millimoles). After slowly raising the temperature, the resulting mixture was stirred at ambient temperature for 24 hours. The organic layer was extracted with dichloromethane (290 ml), washed with distilled water (400 ml), dried over magnesium sulfate, and distilled under reduced pressure. The obtained solid was washed with methanol (50 mL) and hexane (30 mL) to obtain compound (203) (13 g, 42 mmol, 55%).
[0083] Compound (203) (13 g, 42 mmol), 2-bromotoluene (11 g, 64 mmol), tetrakis(triphenylphosphine) palladium (Pd(PPh 3 ) 4 ) (4.9 g, 4 mmol), 1.0 M aqueous potassium carbonate solution (210 mL), Aliquat 336 (4.2 g, 8.5 mmol) and toluene (300 m...
Synthetic example 3
[0088] [Synthesis Example 3] Synthesis of Compound (303)
[0089]
[0090] 9-Bromoanthracene (10 g, 38 mmol), m-tolylboronic acid (5.8 g, 42 mmol), tetrakis(triphenylphosphine) palladium (Pd(PPh 3 ) 4 ) (4.5 g, 3.8 mmol), 2.0 M aqueous sodium carbonate (190 mL), toluene (200 mL) and ethanol (100 mL). After stirring under reflux for 12 hours, the reaction mixture was treated in the same manner as for compound (201) to obtain compound (206) (10 g, 37 mmol).
[0091] Compound (206) (10 g, 37 mmol) and N-bromosuccinimide (NBS) (7.2 g, 40 mmol) were dissolved in dichloromethane (200 mL), and the solution was stirred at ambient temperature for 12 h . Dichloromethane was distilled under reduced pressure to obtain an oil, which was recrystallized from methanol (30 mL) and dried under reduced pressure to obtain Compound (207) (8.2 g, 23 mmol) as a yellow powder.
[0092] Compound (207) (5 g, 14,4 mmol), compound (104) (2.5 g, 4.8 mmol), tetrakis(triphenylphosphine) palladium (Pd...
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