Star-shaped phenanthroxaline derivatives, preparation method and application, and electroluminescent device
An electroluminescent device, phenanthroxaline-based technology, applied in the field of luminescent materials, can solve problems such as slow electron transfer rate, low device efficiency, and insufficient solubility, and achieve the effects of low cost, high thermal stability, and high quantum efficiency
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Embodiment 1
[0045] When n=1, the star-shaped phenanthroxaline derivatives are 3,6,10,13-tetrakis(9,9-dihexylfluorenyl)phenanthroxaline (abbreviated as TFPhZN), the molecular Structural formula such as Image 6 shown.
[0046] Its preparation method comprises the following steps:
[0047] a. Mix 3,6-dibromo-o-phenylenediamine (2.64g, 10.0mmol), 3,6-dibromo-9,10-phenanthrenequinone (3.64g, 10.0mmol) and sodium hydroxide (1.0g, 25.0 mmol) was dissolved in absolute ethanol (50.0ml), heated to 100°C and refluxed for 4 hours, a yellow solid slowly precipitated, after the reaction was complete, cooled to room temperature, and directly filtered, the obtained yellow solid 3, 6, 10, 13-Tetrabromophenanthroxaline (5.62g) was dried and used directly in the next reaction, yield: 95%. MS(APCI): theoretical value C 20 h 8 Br 4 N 2 :591.7, experimental value, 593.2(M+1) + .
[0048] b. Dissolve the solid 3,6,10,13-tetrabromophenanthroxaline (2.96g, 5.0mmol) and 9,9-dihexyl-2-fluoreneboronic acid...
Embodiment 2
[0050] When n=2, the star-shaped phenanthroxaline derivative is 3,6,10,13-tetrakis(bis(9,9-dihexylfluorenyl))phenanthroxaline (abbreviated as TDFPhZN) , whose molecular structure is as Figure 7 shown.
[0051] Its preparation method comprises the following steps:
[0052] a. Mix 3,6-dibromo-o-phenylenediamine (2.64g, 10.0mmol), 3,6-dibromo-9,10-phenanthrenequinone (3.64g, 10.0mmol) and sodium hydroxide (1.0g, 25.0 mmol) was dissolved in absolute ethanol (50.0ml), heated to 100°C and refluxed for 4 hours, a yellow solid slowly precipitated, after the reaction was complete, cooled to room temperature, and directly filtered, the obtained yellow solid 3, 6, 10, 13-Tetrabromophenanthroxaline (5.62g) was dried and used directly in the next reaction, yield: 95%. MS(APCI): theoretical value C 20 h 8 Br 4 N 2 :591.7, experimental value, 593.2(M+1) + .
[0053] b. Combine the solid 3,6,10,13-tetrabromophenanthroxaline (2.96g, 5.0mmol) and bis(9,9-dihexyl-2-fluorenyl)boronic ac...
Embodiment 3
[0055] When n=3, the star-shaped phenanthroxaline derivative is 3,6,10,13-tetrakis(tri(9,9-dihexylfluorenyl))phenanthroxaline (abbreviated as TTFPhZN) , whose molecular structure is as Figure 8 shown.
[0056] Its preparation method comprises the following steps:
[0057] a. Mix 3,6-dibromo-o-phenylenediamine (2.64g, 10.0mmol), 3,6-dibromo-9,10-phenanthrenequinone (3.64g, 10.0mmol) and sodium hydroxide (1.0g, 25.0 mmol) was dissolved in absolute ethanol (50.0ml), heated to 100°C and refluxed for 4 hours, a yellow solid slowly precipitated, after the reaction was complete, cooled to room temperature, and directly filtered, the obtained yellow solid 3, 6, 10, 13-Tetrabromophenanthroxaline (5.62g) was dried and used directly in the next reaction, yield: 95%. MS(APCI): theoretical value C 20 h 8 Br 4 N 2 :591.7, experimental value, 593.2(M+1) + .
[0058] b. Combine the solid 3,6,10,13-tetrabromophenanthroxaline (2.96g, 5.0mmol) and tris(9,9-dihexyl-2-fluorenyl)boronic a...
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