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9,10-bis(2,4-dimethoxybiphenyl)anthracene, cyclic trimeric compound thereof, and preparation method and application of trimeric compound

A technology of dimethoxybiphenyl and macrocyclic compounds, which is applied in the field of organic electroluminescent materials to achieve the effects of improving luminous efficiency, reducing interaction and improving luminous performance

Inactive Publication Date: 2019-07-23
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, much less progress has been made in producing high-efficiency blue OLEDs than green / red OLEDs due to the difficulty in developing materials with high efficiency, color purity, efficient transport and long operating time for blue light.

Method used

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  • 9,10-bis(2,4-dimethoxybiphenyl)anthracene, cyclic trimeric compound thereof, and preparation method and application of trimeric compound
  • 9,10-bis(2,4-dimethoxybiphenyl)anthracene, cyclic trimeric compound thereof, and preparation method and application of trimeric compound
  • 9,10-bis(2,4-dimethoxybiphenyl)anthracene, cyclic trimeric compound thereof, and preparation method and application of trimeric compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Synthesis steps of 9,10-bis(2,4-dimethoxybiphenyl)anthracene:

[0023] 9,10-dibromoanthracene and 2,4-dimethoxybiphenylboronic acid were added to the round bottom flask at a molar ratio of 1:1.5, and then anhydrous sodium carbonate and 7% mol of the catalyst [1,1' -bis(diphenylphosphino)ferrocene]palladium dichloride, using 1,4-dioxane and water in a volume ratio of 4:1 as a solvent, heated to reflux at 110°C in an oil bath for 12 hours, and reacted After the end, the solvent was evaporated, extracted with water and dichloromethane, the organic layer was dried over anhydrous sodium sulfate, and the mixture was separated through a silica gel column to obtain a white-green solid 9,10-bis(2,4-dimethoxybiphenyl)anthracene , the yield was 72%. 1 H NMR (500MHz, CDCl3): 3.91(s, 6H), 3.93(s, 6H), 6.66(s, 2H), 6.6(d, J=2.48Hz, 2H), 7.36-7.38(m, 4H), 7.45-7.47(d, J=8.63Hz, 2H), 7.50-7.52(d, J=8.25Hz, 4H), 7.76-7.77(d, J=8.20Hz, 4H), 7.85-7.87(m, 4H) .

Embodiment 2

[0024] Example 2: Synthesis steps of a cyclotrimer with 9,10-bis(2,4-dimethoxybiphenyl)anthracene as a monomer:

[0025] 9,10-bis(2,4-dimethoxybiphenyl)anthracene and paraformaldehyde in a molar ratio of 1:3, using dichloromethane as solvent, dissolved in a 50ml round bottom flask. After dissolving, add catalyst boron trifluoride diethyl ether, react for 1 hour, and point plate for observation. After the reaction was completed, it was quenched with a saturated sodium bicarbonate solution, washed with a saturated sodium chloride solution, and the organic layer was dried over anhydrous sodium sulfate. The obtained mixture was separated with a silica gel column to obtain the product cyclotrimerization with a yield of 37%. 1 H NMR (500MHz, CDCl 3 ):3.95(s,18H,),3.96(s,18H),4.04(s,6H),6.68(s,6H),7.23(s,6H),7.27-7.29(m,12H),7.44-7.45 (d, J=8.02Hz, 12H), 7.71-7.72(d, J=8.20Hz, 12H), 7.79-7.81(m, 12H)

[0026] The 9,10-bis(2,4-dimethoxybiphenyl)anthracene monomer and cyclotrimer sy...

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Abstract

The invention relates to 9,10-bis(2,4-dimethoxybiphenyl)anthracene, a cyclic trimeric compound thereof, and a preparation method and application of the trimeric compound. The 9,10-bis(2,4-dimethoxybiphenyl)anthracene in a blue-light emitting material molecule synthesized by the invention is linked by methylene to form a cyclic trimeric blue-light emitting material molecule. A 9,10-bis(2,4-dimethoxybiphenyl)anthracene monomer introduces four methoxy groups into a molecular skeleton, so that the steric hindrance of the material molecule on the anthracene skeleton of a plane structure is increased, aggregation between molecular chromophores can be prevented more effectively, and interaction between molecules is reduced. In addition, a macrocycle has a unique twisted structure and three-dimensional characteristics, so that the fluorescence quenching effect at relatively high dosage concentration is reduced to a relatively great extent, and the luminous efficiency of materials is significantly increased, thereby significantly improving the luminescence properties of the materials.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to 9,10-bis(2,4-dimethoxybiphenyl)anthracene, its ring trimer compound, its preparation method and application. Background technique [0002] Organic light-emitting diodes (OLEDs) have attracted extensive attention due to their applications in full-color flat panel displays (FPDs), solid-state lighting sources, and backlights for liquid crystal displays. Organic light-emitting diode (OLED)-based displays and solid-state lighting technology are promising alternatives to solid-state lighting technology combined with conventional inorganic light-emitting diode (LED)-based displays because they can be brighter, more adaptive, and last longer longer life and more energy efficient. For full-color display and white lighting, three main colors are necessary: ​​red, green and blue. However, much less progress has been made in producing high-efficien...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/205C07C43/20C07C41/30C09K11/06
CPCC07C41/30C07C43/20C07C43/2055C09K11/06C09K2211/1007C09K2211/1011C07C2603/92
Inventor 贾学顺乔孟雅李春举崔雷
Owner SHANGHAI UNIV
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