Boron-containing organic compound and application thereof in organic electroluminescent device
A technology of organic compounds and boron compounds, applied in the field of semiconductors, can solve problems such as efficiency roll-off, low S1 state radiation transition rate, difficult exciton utilization rate and high fluorescence radiation efficiency
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[0074] Example 1: Synthesis of Intermediate G:
[0075] Take the synthesis of intermediate G1 as an example:
[0076]
[0077] In a 250mL three-necked flask, add 0.012mol of raw material A-1, 0.012mol of raw material B-1, and 0.01mol of raw material C-1 under a nitrogen atmosphere, and dissolve with a mixed solvent (90ml of toluene, 45ml of ethanol), and then add 0.03 mol Na 2 CO 3 Aqueous solution (2M), stirring with nitrogen for 1 hour, then adding 0.0001mol Pd(PPh 3 ) 4 , Heating and refluxing for 15 hours, sampling point plate, the reaction is complete. Naturally cooling, filtering, rotating the filtrate and passing through a silica gel column to obtain intermediate G-1 with a purity of 95.9% and a yield of 87.3%. Elemental analysis structure (molecular formula C 56 H 37 B 2 ClN 2 ): Theoretical value C, 84.61; H, 4.69; B, 2.72; Cl, 4.46; N, 3.52; Test value C, 84.61; H, 4.70; B, 2.71; Cl, 4.47; N, 3.51. ESI-MS(m / z)(M+): The theoretical value is 794.28, and the measured v...
Example Embodiment
[0082] Example 2: Synthesis of compound H2:
[0083]
[0084] (1) Weigh 0.04 mol of raw material D-1 and 0.025 mol of raw material E-1, and lower the temperature to -78°C; under an inert atmosphere, add 0.02 mol BCl 3 , Heated to 100°C and refluxed for 48 hours, the reaction was complete, and passed through a silica gel column to obtain Intermediate J-1; the HPLC purity was 98.6%, and the yield was 87.2%.
[0085] Elemental analysis structure (molecular formula C 20 H 26 BBr): Theoretical value C, 67.26; H, 7.34; B, 3.03; Br, 22.37; Test value C, 67.25; H, 7.34; B, 3.03; Br, 22.38. ESI-MS(m / z)(M + ): The theoretical value is 356.13, and the measured value is 356.23.
[0086] (2) In a 250mL three-necked flask, add 0.01mol of intermediate J-1 and 0.015mol of raw material F-1 in a nitrogen atmosphere, dissolve it with a mixed solvent (90ml of toluene, 45ml of ethanol), and then add 0.03mol of Na 2 CO 3 Aqueous solution (2M), stirring with nitrogen for 1 hour, then adding 0.0001mol Pd(PP...
Example Embodiment
[0089] Example 3: Synthesis of Compound H11:
[0090]
[0091] Take 0.1 mol of Intermediate G-1, add 0.12 mol of tert-butyl lithium, 120 ml of tert-butyl benzene, and keep it at 60°C for 2 hours, then cool to room temperature and add 0.12 mol BBr dropwise 3 After fully reacting for half an hour, water was added to precipitate a solid, which was washed sequentially with n-hexane and recrystallized with ethanol to obtain compound H11. The HPLC purity is 97.3%, and the yield is 82.1%.
[0092] Elemental analysis structure (molecular formula C 56 H 35 B 3 N 2 ): Theoretical value C, 87.54; H, 4.59; B, 4.22; N, 3.65; Test value C, 87.54; H, 4.58; B, 4.22; N, 3.66. ESI-MS(m / z)(M + ): The theoretical value is 768.31, and the measured value is 768.28.
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