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Benzoyl spirocyclic aromatic hydrocarbon sterically hindered luminescent material and preparation method thereof

A technology of benzoyl spiro aromatic hydrocarbons and luminescent materials, applied in luminescent materials, chemical instruments and methods, and condensation preparation of carbonyl compounds, etc., can solve the problems that materials cannot be fully considered, and achieve large steric hindrance effect and good thermal stability sex, mild effect

Active Publication Date: 2019-02-01
XINYANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In order to speed up the commercialization of OLEDs, the combination of TADF and phosphorescent OLEDs is expected to solve the problem that the current TADF or phosphorescent guest materials cannot be fully considered.

Method used

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  • Benzoyl spirocyclic aromatic hydrocarbon sterically hindered luminescent material and preparation method thereof
  • Benzoyl spirocyclic aromatic hydrocarbon sterically hindered luminescent material and preparation method thereof
  • Benzoyl spirocyclic aromatic hydrocarbon sterically hindered luminescent material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Example 1: 2'-[benzoyl]-spiro-9,9'-xanthene fluorene

[0056] Dissolve spiro-9,9'-xanthene fluorene (3.310g, 10.0mmol), anhydrous aluminum trichloride (1.602g, 12.0mmol) in dichloromethane solution, and benzoyl chloride (1.6800g, 12.0mmol) was added dropwise to the reaction flask, and reacted at room temperature for 12 hours. After completion of the reaction, wash with saturated sodium carbonate solution, extract with dichloromethane, dry the organic phase with anhydrous sodium sulfate, concentrate the organic phase, and obtain the target product with a mixed solvent column chromatography of ethyl acetate and sherwood oil, (yield: 78 %), LC-MS (EI) m / z437.1555 [M + ].

Embodiment 2

[0057] Example 2: 2,2'-bis[benzoyl]-spiro-9,9'-xanthene fluorene

[0058] Dissolve spiro-9,9'-xanthene fluorene (3.310g, 10.0mmol), anhydrous aluminum trichloride (3.2040g, 24.0mmol) in dichloromethane solution, and benzoyl chloride (3.3600g, 24.0mmol) was added dropwise to the reaction flask, and reacted at room temperature for 12 hours. Wash with saturated sodium carbonate solution after completion of the reaction, extract with dichloromethane, dry the organic phase with anhydrous sodium sulfate, concentrate the organic phase, obtain the target product with a mixed solvent column chromatography of ethyl acetate and sherwood oil, (yield: 71 %).

Embodiment 3

[0059] Example 3: 2'-[p-fluorobenzoyl]-spiro-9,9'-xanthene fluorene

[0060] Dissolve spiro-9,9'-xanthene fluorene (3.310g, 10.0mmol), anhydrous aluminum trichloride (1.602g, 12.0mmol) in dichloromethane solution, and p-fluorobenzoyl chloride (1.9027 g, 12.0mmol) was added dropwise to the reaction flask, and reacted at room temperature for 12 hours. After completion of the reaction, wash with saturated sodium carbonate solution, extract with dichloromethane, dry the organic phase with anhydrous sodium sulfate, concentrate the organic phase, and obtain the target product with a mixed solvent column chromatography of ethyl acetate and sherwood oil, (yield: 78 %).

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Abstract

The invention relates to a benzoyl spirocyclic aromatic hydrocarbon sterically hindered luminescent material. A preparation method is characterized in that spirocyclic aromatic hydrocarbon is connected with a benzoyl group, and the structure and position of the substituents on the spirocyclic aromatic hydrocarbon or the benzoyl group are used to control the structure of a material and regulate theproperties of the material. A structure is shown as a general formula I in the specification, R1 is a heterocyclic aromatic hydrocarbon functional group containing H atoms, F, Br atoms or nitrogen, R2 is the spirocyclic aromatic hydrocarbon having a steric hindrance effect, and n is a natural number between 1 and 8. The materials have the following characteristics of (1) rigid planar structure; (2) large Pi-conjugated system and high luminous efficiency; (3) high thermal decomposition temperature and stable amorphous form; (4) three-dimensional large volume steric hindrance effect; (5) simpleand easy synthesis method, and cheap raw materials.

Description

technical field [0001] The invention specifically relates to a benzoyl spiro aromatic hydrocarbon steric hindrance type luminescent material and a preparation method thereof, as well as steps and raw materials used in the preparation process of these materials. Background technique [0002] Since 1987, Deng Qingyun et al first reported the organic light-emitting diodes (organic light-emitting devices, OLEDs) with a sandwich structure using 8-hydroxyquinoline aluminum as the light-emitting material. OLEDs are favored by many scientists because of their light weight, wide source of materials, low energy consumption, wide viewing angle, fast response, high contrast, large-area flexible display and many other advantages. Since then, there has been a rapid upsurge in researching OLEDs worldwide. However, the maximum internal quantum efficiency of traditional OLEDs is only 25% because they can only use singlet excitons to emit light, so it is difficult to match the efficiency of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/792C07C49/813C07C45/46C07D311/96C07D335/04C07D405/10C09K11/06
CPCC07C49/792C07C49/813C07D311/96C07D335/04C07D405/10C09K11/06C09K2211/1011C09K2211/1029C09K2211/1088C09K2211/1092C07C2603/94
Inventor 赵祥华李莉吴佳星邹国栋张佳佳
Owner XINYANG NORMAL UNIVERSITY
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