Dihydroanthracene derivative, preparation method and application thereof and luminescent device comprising dihydroanthracene derivative
A technology of dihydroanthracene and compound, applied in the field of organic electroluminescent materials, can solve the problem of large difference in luminous efficiency, achieve the effects of high thermal and chemical stability, avoid stacking quenching, and high current efficiency
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
preparation example Construction
[0088] The present invention also relates to a preparation method of 9,9,10,10-tetraaryl substituted dihydroanthracene derivatives, which comprises the following steps:
[0089] (a) anthraquinone is reacted with phenyl Grignard reagent, and the product obtained is reacted with acid halide to generate the intermediate product of formula (7) in the form of cis-trans isomerism mixture,
[0090]
[0091] where X 1 is selected from hydrogen or halogen, X' is selected from halogen;
[0092] (b) the intermediate product of formula (7) is reacted with the phenyllithium substituted by halogen to obtain the compound of formula (4)
[0093]
[0094] where X 1 、X 2 are each independently selected from hydrogen or halogen, provided that X 1 、X 2 not simultaneously hydrogen;
[0095] (c) reacting the compound of formula (4) with the diarylamine compound of formula (5) under the protection of an inert gas, if appropriate in the presence of a catalyst,
[0096]
[0097] or
...
Embodiment 1
[0146] Example 1 Synthesis of Compound P1
[0147]
[0148] in N 2 Under protection, 150ml of toluene, 8g of 9,9,10,10-tetrakis(p-bromophenyl)dihydroanthracene (10mmol), 8.46g of diphenylamine (50mmol) were successively added to a 250ml three-neck flask equipped with magnetic stirring. , under stirring, add 5.76g sodium tert-butoxide (60mmol), can not dissolve completely, then add 173mgPd (dba) 2 (bisdibenzylidene acetone palladium, 0.3mmol), the color becomes dark, then add 1.2g 10% Tri-tert-butylphosphine-n-hexane solution (0.6mmol), heat to reflux, the reaction solution turns green, after reflux for 8 hours, spot the plate, almost no raw materials, when the temperature drops below 45°C, add a mixed solution of 5ml concentrated hydrochloric acid and 100ml water , liquid separation, the aqueous phase was extracted with 100ml toluene, combined and spin-dried to obtain a crude product, which was recrystallized with dichloromethane / ethanol (volume ratio 1:1) system to obtain...
Embodiment 2
[0149] Synthesis of Example 2 Compound P2
[0150]
[0151] in N 2 Under protection, 150ml of toluene, 8g of 9,9,10,10-tetrakis(m-bromophenyl)dihydroanthracene (10mmol), 8.46g of diphenylamine (50mmol) were successively added to a 250ml three-neck flask equipped with magnetic stirring. , under stirring, add 5.76g sodium tert-butoxide (60mmol), can not dissolve completely, then add 173mgPd (dba) 2 (0.3mmol), the color becomes darker, then add 1.2g 10% tri-tert-butylphosphine n-hexane solution (0.6mmol), heated to reflux, the reaction solution turned green, and after reflux for 10 hours, the plate was spotted, and there was basically no raw material. When the temperature was lowered to below 45°C, a mixed solution of 5ml concentrated hydrochloric acid and 100ml water was added, separated, and 150ml was used for the aqueous phase. Extracted with toluene, combined and spin-dried to obtain a crude product, which was recrystallized with a dichloromethane / ethanol system (volume r...
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More