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Pyrene-based organic material, preparation method, and application thereof

An organic material and pyrene-based technology, applied in the field of organic semiconductor materials, can solve problems such as device temperature rise, emission spectrum red shift, and lower luminous efficiency, and achieve high solubility, simple synthesis method, and cheap raw materials.

Active Publication Date: 2017-10-27
NANJING CEC PANDA LCD TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Pyrene has blue light emission, high fluorescence quantum efficiency, excellent fluorescence properties and good thermal stability, but pyrene is easy to form aggregation or excimer compounds, resulting in a red shift of the emission spectrum, and at the same time reduces the luminous efficiency. The reduction of luminous efficiency makes A large amount of energy is converted into heat energy, which increases the temperature of the device and ultimately reduces the lifetime. Therefore, inhibiting the aggregation of pyrene is an international research hotspot in the field of organic electroluminescence.

Method used

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  • Pyrene-based organic material, preparation method, and application thereof
  • Pyrene-based organic material, preparation method, and application thereof
  • Pyrene-based organic material, preparation method, and application thereof

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no. 1 example

[0083] The first embodiment: the name of the pyrene-based organic material is: 1.6-bis(9,9-diphenylfluorenyl)pyrene, the chemical name is: BDPhFPy, and its chemical formula structure is as follows:

[0084]

[0085] The preparation method of diphenylfluoreneboronic acid pinacol ester is as follows:

[0086] Among them, the chemical structure of 2-bromo-9,9-diphenylfluorene is as follows:

[0087]

[0088] The chemical structure of pinacol diboronate is as follows:

[0089]

[0090] The chemical structure of 1,1'-bis(diphenylphosphino)ferrocene (DPPF) is as follows:

[0091]

[0092] The chemical structure of 1,4-dioxane is as follows:

[0093]

[0094] Accurately weighed 2-bromo-9,9-diphenylfluorene (3.9mmol), biboronic acid pinacol ester (5.9mmol), palladium acetate (Pd(OAC) 2 , 0.15mmol), potassium acetate (KOAc, 9.4mmol) and 1,1'-bis(diphenylphosphino)ferrocene (DPPF) (0.3mmol) were placed in a clean and dry two-necked flask (250ml ), vacuuming and nitrog...

no. 2 example

[0111] Second embodiment: the name of the pyrene-based organic material is: 1.6-bispirobisfluorene pyrene, the chemical name is: DSBFPy, and its chemical formula structure is as follows:

[0112]

[0113] The preparation method of spirobifluorene boronic acid pinacol ester is as follows:

[0114] Accurately weighed 2-bromo-spirobifluorene (3.9mmol), biboronic acid pinacol ester (5.9mmol), palladium acetate (Pd(OAC) 2 , 0.15mmol), potassium acetate (KOAC, 9.4mmol) and 1,1'-bis(diphenylphosphino)ferrocene (DPPF) (0.3mmol) were placed in a clean and dry two-necked flask (250ml ), vacuuming and nitrogen filling were repeated three times. Deoxygenate 1,4-dioxane for about 1 hour in advance, and draw about 40ml into the reaction bottle with a syringe. During the whole reaction process, avoid light, pass condensed water, and reflux at 90°C for 12h. After the reaction was completed, an appropriate amount of water was added to the reaction solution, the liquid was extracted and s...

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Abstract

The invention relates to a pyrene organic material, a preparing method and an application of the pyrene organic material. The material which is built with the preparing method and is of a dumbbell-similar structure serves as an organic semiconductor to be applied to an organic electronic device. The general molecular formula of the material is shown in the specification. The material has the advantages that raw materials are low in price, and the synthesis method is simple and convenient; the dumbbell-shaped structure is adopted; high thermal stability and glass transition temperature are achieved; the material has good flexibility and high solubility; good photoelectric activity is achieved. The pyrene-based organic dumbbell-shaped material can be applied to the organic electronic fields such as organic luminescence display, organic optical storing, organic field effect transistors and organic lasers of thin-film devices. An electroluminescence device prepared from the material obtains the satisfactory results in the luminance aspect, the luminous efficiency aspect, the voltage-proof stability aspect and the like.

Description

technical field [0001] The invention belongs to the technical field of organic semiconductor materials, and specifically relates to a pyrene-based organic dumbbell-shaped material and a preparation method thereof, and an organic electroluminescent device made of the material, and relates to the application of the material in organic electroluminescent devices, photovoltaic cells , organic electrical storage, organic nonlinear optics, chemical and biological sensing, and organic lasers. technical background [0002] Since 1987, the Tang Research Group of Kodak Company of the United States [Tang, C.W.; Van Slyke, S.A.Appl.Phys. Lett. R.N.; Mackay, K.; Friend, R.H.; Burn, P.L.; Holmes, A.B.Nature 1990,347,539.] published organic and polymer fluorescent materials to make thin-film organic electroluminescent devices (Organic Light-emitting Diodes) Since Polymeric Light-emitting Diodes (Polymeric Light-emitting Diodes), organic flat-panel displays have become another generation o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C13/72C07C1/32C09K11/06H01L51/54H01L51/50
Inventor 许卫锋解令海黄维欧昌金
Owner NANJING CEC PANDA LCD TECH
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