Application of o-hydroxyphenylazole derivatives as organic blue light materials

A technology of organic molecular materials and blue light, applied in luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of luminescent color purity, quantum efficiency and low stability, and achieve high fluorescence quantum efficiency and good thermal stability , good effect of color purity

Inactive Publication Date: 2020-09-11
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, small-molecule blue-light materials mainly include aromatic hydrocarbons, aromatic amines, organic borons, and organosilicons. Disadvantages such as low luminous color purity, quantum efficiency and stability [see: (a) Chen, C.T., Chiang, C.L, Lin, Y, C.Org.Lett., 2003, 5, 1261. (b) Noda, T. , Shirota, Y.J.Am Chem.Soc.1998,120,9714. (c) Chen,H.Y.,Lam,W.Y,Luo,J.D,Appl.Phys.Lett.,2002,81,574.]

Method used

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  • Application of o-hydroxyphenylazole derivatives as organic blue light materials
  • Application of o-hydroxyphenylazole derivatives as organic blue light materials
  • Application of o-hydroxyphenylazole derivatives as organic blue light materials

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Synthesis of 2-(5-(4'-(diphenylamino)-[1,1'-diphenyl]-4-)oxazol-2-yl)-6-methylphenol

[0030]Under nitrogen protection, o-methylphenoxyacetamide (0.2mmol, 33.2mg), 4'-(5-oxazolyl)-N,N-diphenyl-[1,1'-diphenyl] -4-amine (0.3mmol, 116.4mg), dichloro(pentamethylcyclopentadienyl) rhodium (III) dimer (5.0mol%, 6.4mg), silver hexafluoroantimonate (20mol%, 13.6mg), pivalic acid (0.4mmol, 41.0mg), cesium pivalate (0.16mmol, 38mg), silver carbonate (0.08mmol, 22mg) were added to a reaction tube equipped with a magnetic stirrer, and added under nitrogen N,N-Dimethylformamide (1.0 mL) was stirred at room temperature for 5 minutes, and then reacted at 140° C. for 24 hours. After the reaction was completed, the reaction tube was cooled to room temperature, ethyl acetate was added to dilute the reaction system, filtered through diatomaceous earth, and washed with ethyl acetate, the filtrates were combined, the solvent was removed under reduced pressure, and the residue was...

Embodiment 2

[0031] Example 2: Synthesis of 2-(5-(4'-(diphenylamino)-[1,1'-diphenyl]-4-)oxazol-2-yl)-4-methylphenol

[0032] Under nitrogen protection, p-methylphenoxyacetamide (0.2mmol, 33.2mg), 4'-(5-oxazolyl)-N,N-diphenyl-[1,1'-diphenyl] -4-amine (0.3mmol, 116.4mg), dichloro(pentamethylcyclopentadienyl) rhodium (III) dimer (5.0mol%, 6.4mg), silver hexafluoroantimonate (20mol%, 13.6mg), pivalic acid (0.4mmol, 41.0mg), cesium pivalate (0.16mmol, 38mg), silver carbonate (0.08mmol, 22mg) were added to a reaction tube equipped with a magnetic stirrer, and added under nitrogen N,N-Dimethylformamide (1.0 mL) was stirred at room temperature for 5 minutes, and then reacted at 140° C. for 24 hours. After the reaction was completed, the reaction tube was cooled to room temperature, ethyl acetate was added to dilute the reaction system, filtered through diatomaceous earth, and washed with ethyl acetate, the filtrates were combined, the solvent was removed under reduced pressure, and the residue wa...

Embodiment 3

[0033] Example 3: 2-(5-(4'-(diphenylamino)-[1,1'-diphenyl]-4-)oxazol-2-yl)-6-trifluoromethylphenol Synthesis

[0034] Under nitrogen protection, p-trifluoromethylphenoxyacetamide (0.2mmol, 43.8mg), 4'-(5-oxazolyl)-N,N-diphenyl-[1,1'-diphenyl Base]-4-amine (0.3mmol, 116.4mg), dichloro(pentamethylcyclopentadienyl) rhodium (III) dimer (5.0mol%, 6.4mg), silver hexafluoroantimonate (20mol %, 13.6mg), pivalic acid (0.4mmol, 41.0mg), cesium pivalate (0.16mmol, 38mg), silver carbonate (0.08mmol, 22mg) were added to the reaction tube equipped with a magnetic stirrer, under nitrogen N,N-dimethylformamide (1.0 mL) was added under low temperature, stirred at room temperature for 5 minutes, and then reacted at 140° C. for 24 hours. After the reaction was completed, the reaction tube was cooled to room temperature, ethyl acetate was added to dilute the reaction system, filtered through diatomaceous earth, and washed with ethyl acetate, the filtrates were combined, the solvent was removed ...

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Abstract

The invention belongs to a blue organic molecular material with high quantum efficiency and a preparation method thereof. The blue organic molecular material is an o-hydroxyphenylazole derivative compound, only shows single enolic emission in a solution and a solid film, and has good blue light emission properties. The blue-light organic molecular material with high quantum efficiency has good heat stability, and has a synthetic route of a direct oxidative cross-coupling reaction; thus, compared with a traditional preparation technology of a condensation reaction, the synthetic route shortens lengthy organic synthetic steps, improves the total yield of a synthetic reaction, reduces cost, avoids a great amount of wastes from generation, is simple, convenient and rapid, and can efficiently and rapidly obtain a blue light molecular library. The blue o-hydroxyphenylazole compound with high quantum efficiency has a fluorescence emission peak located at a wavelength of 420 to 434 nm in a toluene solution, an illuminant color coordinate of CIE[0.15, (0.05-0.07)], and a quantum yield up to 84 to 88%.

Description

technical field [0001] The invention relates to the molecular structure of a class of o-hydroxyphenylazole derivatives and its application as an organic blue light material. Background technique [0002] As an emerging display technology, organic electroluminescence technology has the advantages of high brightness, low driving voltage, high luminous efficiency, simple structure, and large viewing angle, and has a very broad application prospect. Among the red, green and blue primary color materials currently used to prepare full-color organic light-emitting diodes, red light materials and green light materials have basically met the requirements of industrialization, while blue light materials are far behind in terms of fluorescence efficiency, color purity, lifespan, and brightness. There is still a long way to go for industrial application, which has become a technical problem in this industry. [See: (a) Zhu, X.-H.; Peng, J.; Cao, Y.; Roncali, J. Chem. Soc. Rev., 2011, 40...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D263/32C09K11/06
CPCC07D263/32C09K11/06C09K2211/1033
Inventor 游劲松李必进兰静波吴迪高戈
Owner SICHUAN UNIV
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