Organic semiconductor material, preparation method of organic semiconductor material and electroluminescent device
An electroluminescent device, organic semiconductor technology, applied in semiconductor devices, semiconductor/solid-state device manufacturing, electric solid-state devices, etc., can solve problems such as lack, achieve high triplet energy level, improve luminous efficiency, and the synthesis method is simple and easy row effect
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Embodiment 1
[0025] Preparation process of 2,7-bis(phenylsulfoxy)-9,9-bis(2-(9-phenylcarbazole))fluorene
[0026] 1. Compound D: The structural formula of 2,7-dibromo-9,9-bis(2-(9-phenylcarbazole))fluorene is The synthesis is as follows:
[0027]
[0028] Compound A: 2,7-dibromofluorenone (5.4g, 16mmol) was mixed with compound B: 9-phenylcarbazole (13.4g, 55mmlo), and heated to 120°C under nitrogen atmosphere. After the mixture was completely dissolved, drop Add 1 mL of catalyst trifluoromethanesulfonic acid and keep heating overnight. After the reaction, dichloromethane was added to dissolve the unreacted raw materials and other impurities, and the white solid compound D was obtained by filtration: 2,7-dibromo-9,9-bis(2-(9-phenylcarbazole))fluorene, producing The rate is 82%.
[0029] Experimental test data: mass spectrum: m / z 806.0 (M + +1); elemental analysis (%) C 49 h 30 Br 2 N 2 : theoretical value C 72.97, H 3.75, N 3.47; found value: C 72.95, H 3.60, N 3.54.
[0030] 2...
Embodiment 2
[0035] Example 2: Preparation process of 2,7-bis(phenylsulfoxy)-9,9-bis(2-(9-phenylcarbazole))fluorene 1. Compound D: 2,7-dibromo-9 , Refer to Example 1 for the preparation of 9-bis(2-(9-phenylcarbazole))fluorene.
[0036] 2. The structural formula of 2,7-bis(phenylsulfoxy)-9,9-bis(2-(9-phenylcarbazole))fluorene is The synthesis is as follows:
[0037]
[0038] Compound D: 2,7-dibromo-9,9-bis(2-(9-phenylcarbazole))fluorene (7.3 g, 9 mmol) was dissolved in sodium carbonate (2.12 g, 20.0 mmol) in toluene (150 mL ) solution, then add compound C: thiophenol (2.3g, 20.7mmol) and mix in a three-neck flask, stir and react at 110°C for 10 hours, stop the reaction and cool to room temperature, extract with dichloromethane, and remove the solvent by rotary evaporation , to obtain a crude product, then dissolve the crude product with acetic acid (100 mL), add 30% by mass hydrogen peroxide (50 mL), and stir at 85°C for 16 hours. Wash the crude product with saturated brine and disti...
Embodiment 3
[0039] Example 3: Preparation process of 2,7-bis(phenylsulfoxy)-9,9-bis(2-(9-phenylcarbazole))fluorene
[0040] 1. Compound D: Refer to Example 1 for the preparation of 2,7-dibromo-9,9-bis(2-(9-phenylcarbazole))fluorene.
[0041]2. The structural formula of 2,7-bis(phenylsulfoxy)-9,9-bis(2-(9-phenylcarbazole))fluorene is The synthesis is as follows:
[0042]
[0043] Compound D: 2,7-dibromo-9,9-bis(2-(9-phenylcarbazole))fluorene (7.3 g, 9 mmol) was dissolved in sodium bicarbonate (1.68 g, 20.0 mmol) in tetrahydrofuran ( 150mL) solution, then add compound C: thiophenol (2.4g, 21.6mmol) and mix in a three-necked flask, stir and react at 110°C for 10 hours, stop the reaction and cool to room temperature, extract with dichloromethane, and remove by rotary evaporation solvent to obtain the crude product, then dissolve the crude product with acetic acid (100 mL), add 30% by mass hydrogen peroxide (50 mL), and stir at 90°C for 12 hours. Wash the crude product with saturated br...
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