Bipolar body organic electroluminescent material and application thereof
An electroluminescent material, bipolar technology, applied in luminescent materials, organic chemistry, circuits, etc., can solve the problems of unbalanced OLED turn-on voltage and life, high turn-on voltage, disadvantage, etc., to improve external quantum efficiency, Effects of high stability, high glass transition temperature and thermal decomposition temperature
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Embodiment 1
[0079] Embodiment 1: Preparation of intermediate 1,8-diazadibenzothiophene sulfone
[0080]
[0081] Preparation of intermediate 1,8-diazadibenzothiophene sulfone: Add 1,8-diazadibenzothiophene (18.6 g, 0.1 mol) and AcOH (300 mL) into a 2 L three-necked flask. At room temperature, a mass fraction of 30% H was added dropwise 2 o 2 (1200mL), the dropwise addition was completed within 1 hour. Under nitrogen protection, stir at reflux for 18h. Room temperature 25°C, suction filtration under reduced pressure to obtain a white powdery solid, rinse the filter cake with water until neutral. Add 200 mL of diethyl ether to the obtained white solid, stir at room temperature for 1 h, and filter with suction to obtain 18.7 g of white powdery solid product, yield: 86%.
[0082] Mass spectrum MS (m / e), molecular formula C 10 h 6 N 2 o 2 S, theoretical value 218.0, test value 219.0.
[0083] Elemental analysis (C 10 h 6 N 2 o 2 S), theoretical value C: 55.04%, H: 2.77%, O: 14....
Embodiment 2
[0084] Embodiment 2: the preparation of intermediate M1
[0085]
[0086] 1) Preparation of Intermediate M1-A
[0087] In a 250mL three-necked flask, 1,8-diazadibenzothiophene sulfone (4.36g, 0.02mol), 2,7-dibromo-9H-xanthene (11.6g, 0.034mol), dioxane ring (100 mL). Nitrogen strictly replaces the air in the reaction system, and maintains the nitrogen environment of the system. At room temperature of 25°C, KN(SiMe 3 ) 2 Toluene solution (0.5M, 120mL, 0.06mol), the dropwise addition was completed within 50min. The bath temperature was set at 100°C, the reaction was kept for 12 hours, and the temperature was lowered to room temperature 25°C. Pour 100 mL of saturated NH into the reaction system 4 Cl aqueous solution was used to quench the reaction system. Extract twice with 100 mL of ethyl acetate, combine the organic phases, wash the organic phase with 100 mL*2 water until the organic phase is neutral, dry the organic phase with anhydrous sodium sulfate, filter under re...
Embodiment 3
[0098] Embodiment 3: the preparation of intermediate M2
[0099]
[0100] Using a method similar to Example 2, using equimolar equivalents of 2,7-dibromo-9H-thioxanthene instead of 2,7-dibromo-9H-oxanthene, and other conditions unchanged, intermediate M2 was obtained , off-white solid 3.7g, yield 35%.
[0101] Mass spectrum MS (m / e), molecular formula C 35 h 20 N 4 S, theoretical value 528.1, test value 529.1.
[0102] Elemental analysis (C 35 h 20 N 4 S), theoretical value C: 79.52%, H: 3.81%, N: 10.60%, S: 6.07%; measured value C: 79.54%, H: 3.80%, N: 10.63%, S: 6.03%.
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