Organic small-molecule luminescent material and organic electroluminescent device

A technology of luminescent materials and small molecules, applied in luminescent materials, electrical solid devices, electrical components, etc., can solve the problems of limited organic small molecule optoelectronic materials, and achieve the effects of improving external quantum efficiency, single structure, and definite molecular weight

Active Publication Date: 2019-03-08
SHENZHEN CHINA STAR OPTOELECTRONICS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, organic small molecule optoelectronic materials with simple structure, good performance and meeting commercial needs are still very limited, and the development of new organic optoelectronic materials is still of great significance

Method used

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  • Organic small-molecule luminescent material and organic electroluminescent device
  • Organic small-molecule luminescent material and organic electroluminescent device
  • Organic small-molecule luminescent material and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] The synthetic method 1 of 2-bromo-N-phenylaniline, chemical reaction formula is as follows:

[0059]

[0060] In a 250mL three-necked flask, add aniline (0.2mol, 18.6g), o-bromoiodobenzene (0.2mol, 56.58g), palladium acetate (0.6mmol, 134.4mg), sodium tert-butoxide (0.4 mol) into the flask in turn, then add 150mL of toluene, pass N 2 20 minutes, then add tert-butylphosphine (1.2mmol, 1.2ml), continue to pass through N 2 20 minutes, heat to reflux and stir for 12 hours. The temperature was lowered to room temperature, sodium tert-butoxide was removed by suction filtration, the solvent was distilled off under pressure, and the solvent was separated and purified by silica gel chromatography to obtain a colorless oily liquid (27.8 g, yield 56%).

Embodiment 2

[0062] The synthetic method 2 of 2-bromo-N-phenylaniline, chemical reaction formula is as follows:

[0063]

[0064] In a 250mL three-necked flask, add aniline (0.2mol, 18.6g), o-bromoiodobenzene (0.2mol, 56.58g), palladium acetate (0.6mmol, 134.4mg), sodium tert-butoxide (0.4 mol) was added in the flask successively, o-bis(2-phenyl)bis(diphenylphosphine) (0.6mmol, 340mg), then added the toluene of 150mL, logical N 2 20 minutes, heat to reflux and stir for 12 hours. The temperature was lowered to room temperature, sodium tert-butoxide was removed by suction filtration, the solvent was distilled off under pressure, and the solvent was separated and purified by silica gel chromatography to obtain a colorless oily liquid (44.2 g, yield 89%).

[0065] After comparing the above Example 1 and Example 2, it can be found that by changing the catalyst ligand from t-butylphosphine to o-bis(2-phenyl)bis(diphenylphosphine), 2-bromo-N-benzene Aniline yield increased from 56% to 89%. ...

Embodiment 3

[0067] The preparation method 1 of (4-bromophenyl)-phenyl-carbamic acid tert-butyl ester, chemical reaction formula is as follows:

[0068]

[0069] In a 500 ml one-necked flask, di-tert-butyl dicarbonate (BOC) (0.2mol, 43.6g) was added to 400 ml of tetrahydrofuran at room temperature, and then p-N-(dibromophenyl)aniline (0.1mol , 24.8g), heated to reflux and stirred for 24 hours. The mixture was then poured into 1 L of water, and the product was extracted with dichloromethane. Dry the organic phase with anhydrous magnesium sulfate, remove the solvent after separation, and separate and purify with silica gel chromatography to obtain a colorless oily liquid (32.0 g, yield 92%).

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Abstract

The invention provides an organic small-molecule luminescent material and an organic electroluminescent device. The organic small-molecule luminescent material provided by the invention is obtained bycoupling a novel acridine donor unit 10H-spiro[acridine-9,2'-adamantane] with a receptor unit. The organic small-molecule luminescent material has a single structure and a determined molecular weight, is convenient for purification and high in multiple synthetic reproducibility, and has low sublimation temperature and high decomposition temperature and stable film morphology; since the non-aromatic rigid structure adamantine is used as a donor part structure, the organic small-molecule luminescent material has a high photoluminescent quantum yield in the film state; when the organic small-molecule luminescent material is applied to the organic electroluminescent device, the problem of low efficiency of the device caused by serious non-radiative attenuation due to configuration relaxationof an excited state molecule can be effectively solved.

Description

technical field [0001] The invention relates to the field of organic electroluminescence, in particular to an organic small molecule luminescent material and an organic electroluminescent device using the organic small molecule luminescent material. Background technique [0002] Organic electroluminescence (OLED) device is a self-luminous device, which has the advantages of low voltage, wide viewing angle, fast response speed, and good temperature adaptability. It is a new generation of display technology. At present, a few manufacturers have mass-produced OLED panels, and more companies have also entered the stage of R&D and mass production. [0003] The principle of an organic electroluminescent device is that, under the action of an electric field, holes and electrons are injected from the anode and cathode respectively, pass through the hole injection layer, the hole transport layer, the electron injection layer, and the electron transport layer respectively, and then re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/20C07D401/10C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D221/20C07D401/10C09K2211/1007C09K2211/1059H10K85/654H10K50/12
Inventor 吴元均矫士博史婷苏仕健李伟李彬彬
Owner SHENZHEN CHINA STAR OPTOELECTRONICS TECH CO LTD
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