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Main material based on phenanthrene and imidazole derivative and electroluminescent device

An electroluminescent device, phenanthroimidazole technology, applied in the field of electroluminescent devices, can solve problems such as stagnation, no practical use of the process, and difficult growth of single crystals

Active Publication Date: 2014-06-18
JILIN YUANHE ELECTRONICS MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the development of organic electroluminescence has been stagnant due to the difficulty in growing single crystals, high driving voltage, and almost no practical use of the technology used.

Method used

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  • Main material based on phenanthrene and imidazole derivative and electroluminescent device
  • Main material based on phenanthrene and imidazole derivative and electroluminescent device
  • Main material based on phenanthrene and imidazole derivative and electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1: the synthesis of compound 1:

[0023] Add phenanthrenequinone (830mg, 4mmol), m-phthalaldehyde (528mg, 4mmol), aniline (1.48g, 16mmol), ammonium acetate (1.6g, 20mmol), and acetic acid (40ml) into a three-necked flask, under N2 protection, in The oil bath was heated to reflux at 123°C for 12h. Stop the reaction, pour the reaction mixture into distilled water, stir and filter, the obtained gray filter cake is washed with water, glacial acetic acid, and ethanol in sequence, and after drying, the monoaldehyde product is obtained. The intermediate (339mg, 1mmol), 1,10-phenanthrene Add roline-5,6-dione (208mg, 1mmol), ammonium acetate (308mg, 4mmol), aniline (465mg, 5mmol), and acetic acid (20ml) into a three-necked flask, heat and reflux in an oil bath at 123°C for 12 hours, stop The reaction was poured into water, and the filter cake was washed with water and ethanol, and vacuum sublimated to obtain a yellow product (312 mg, yield 47%). The molecular ion ma...

Embodiment 2

[0024] Embodiment 2: the synthesis of compound 2:

[0025] Add phenanthrenequinone (4.16g, 20mmol), p-bromobenzaldehyde (4.07g, 22mmol), ammonium acetate (6.16g, 80mmol), aniline (9.3g, 100mmol) and 160ml of glacial acetic acid into a 250ml two-necked bottle. N 2 Under protection, the mixture was heated and refluxed for 12 hours, the reaction was stopped, suction filtered, and the filter cake was washed with water and methanol in sequence to obtain the meta-bromo-substituted phenanthroimidazole intermediate (6.81g, yield 76%), and the product was directly dried to make Next reaction. The meta-bromo-substituted phenanthroimidazole (0.90 g, 2 mmol) obtained above was dissolved in 30 ml of freshly distilled THF mixture, and cooled to -78°C with a liquid nitrogen / acetone bath. The deoxygenation operation was repeated several times by evacuating nitrogen, and then adding n-butyllithium (0.88ml, 2.5M n-hexane solution) dropwise. The solution was kept at -78°C and stirred for thre...

Embodiment 3

[0026] Embodiment 3: the synthesis of compound 3:

[0027] Cool the above-mentioned 30ml freshly distilled THF solution with meta-bromine-substituted phenanthroimidazole (2.04g, 4.5mmol) to -78°C with a liquid nitrogen / acetone bath, vacuumize and ventilate nitrogen repeatedly to remove oxygen and then drop by drop Add n-butyllithium (2.5M n-hexane solution, 2ml), stir at this temperature for 3 hours, then add phenyl phosphorus dichloride (0.27g, 1.5mmol) dropwise, then slowly return to room temperature and continue stirring 12 hours. Add 30 ml of methanol to the reaction and extract with dichloromethane, combine the organic phases with anhydrous MgSO 4 Dry and spin the solvent to purify by column chromatography (silica gel, dichloromethane / ethyl acetate volume ratio=20 / 1). The resulting crude product was dissolved in 10ml of dichloromethane, added aqueous hydrogen peroxide solution (30%, 0.4ml, 3mmol), and stirred at room temperature for 12 hours. The reaction was stopped, ...

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Abstract

The invention relates to a main material based on a phenanthrene and imidazole derivative and an electroluminescent device, belonging to the technical field of organic electroluminescence. The structural general formula of the main material disclosed by the invention is represented by the FORMULA described in the specification, wherein the R substituent group and the phenanthrene and imidazole group are in the meta-position or para-position; R can be a 1,10-phenanthroline derivative, a triphenylphosphine oxide derivative or a triphenyl borane derivative; R1-R4 are H, alkyl containing 1-4 C atoms, halogenated alkyl, aromatic ring and the like; a luminescent layer of the electroluminescent device is commonly prepared from the main material based on the phenanthrene and imidazole derivative and a phosphorescence doped material. The electroluminescent device emits green light, yellow light, red light and the like. The electroluminescent device can be used in the application fields, such as panel display and illumination light sources.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence, and specifically relates to a class of host materials based on phenanthroimidazole derivatives and an electroluminescence device in which a light-emitting layer is jointly prepared by these host materials and phosphorescence doping materials. Background technique [0002] The phenomenon of organic electroluminescence was first reported in the early 1960s. Pope et al. observed the blue light emitted by anthracene when a high voltage of 400 volts was applied to both sides of anthracene single crystal (see M.Pope, H.Kallmann and P Magnante, J. Chem. Phys., 1963, 38, 2042). However, due to the difficulty in growing single crystals, the high driving voltage, and almost no practical use of the technology used, the development of organic electroluminescence has been stagnant. [0003] Until 1987, C.W.Tang et al. of Kokak Company in the United States used ultra-thin film technology t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D471/14C07F9/6506C07F5/02H01L51/54
Inventor 王悦
Owner JILIN YUANHE ELECTRONICS MATERIALS CO LTD
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