Aromatic amine compound containing 9,9'-spirobifluorene and dibenzothiophene and organic electroluminescent device thereof
A technology of dibenzothiophene and spirobifluorene, which is applied in the field of organic photoelectric materials, can solve the problems of low color purity, low efficiency, and short life of organic electrical components, and achieve good hole transport ability, stability, and excellent performance , Improve the effect of luminous efficiency
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[0059] Example 1: Preparation of Bromide B
[0060]
[0061]
[0062] Preparation of Bromide B-1:
[0063]
[0064] a) Under nitrogen atmosphere, dissolve methyl 2-iodo-3-bromobenzoate (10.0 g, 30 mmol), phenylboronic acid (3.66 g, 30 mmol) and tetrakis(triphenylphosphine)palladium (1.7 g, 1.46 mmol) In 100 ml of tetrahydrofuran, stirred for 30 minutes, then added dropwise 50 ml of potassium carbonate aqueous solution (1.63 g, 11.18 mmol) within 20 minutes, refluxed overnight, washed with water, extracted with dichloromethane, and evaporated the organic solvent; b) The obtained solid (8.5 g, 255.0 mmol) and sodium hydroxide (1.2 g, 30 mmol) were dissolved in 100 ml of ethanol, refluxed for 6 hours, cooled to room temperature, neutralized with 2M hydrochloric acid, filtered, and the obtained solid was recrystallized in ethanol; c) the obtained The crystals (10 g, 30 mmol) were dissolved in 300 ml of methanesulfonic acid, stirred at 30°C for 24 hours, poured into ice w...
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[0070] Example 2: Preparation of aromatic amine compound A
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[0072]
[0073] Preparation of compound A-1:
[0074]
[0075] Bromobenzene (4.71g, 30mmol), cuprous iodide (0.06g, 0.3mmol) and 45ml liquid ammonia were added to the flask, reacted at 100°C for 18 hours, filtered, and the liquid was extracted, washed, dried, and the organic solvent was removed , and finally obtain compound A-1.
[0076] Compounds A-2 to A-36 can be prepared by the above methods.
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[0077] Example 3: Preparation of Intermediate M
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[0079]
[0080]
[0081] Preparation of intermediate M-1: Under argon atmosphere, bromide B-1 (5.93 g, 15 mmol), aromatic amine compound A-1 (1.40 g, 15 mmol), sodium tert-butoxide (2.88 g, 30 mmol) were added to To 150 ml of dehydrated toluene, palladium acetate (0.07 g, 0.3 mmol) and tri-tert-butylphosphine (0.06 g, 0.3 mmol) were added with stirring, and the mixture was reacted at 80° C. for 8 hours. After cooling, it was filtered through a celite / silica funnel, the organic solvent was removed from the filtrate by distillation under reduced pressure, the obtained residue was recrystallized from toluene, and the obtained solid was collected by filtration and dried to obtain Intermediate M-1.
[0082] Intermediates M-2 to M-124 can all be prepared by the methods described above.
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