Bipolar-configuration pyrenyl blue-light emitting material containing benzimidazole unit, preparation method and application

A technology of benzimidazole and blue light materials, which is applied in the direction of luminescent materials, chemical instruments and methods, electrical components, etc., can solve the problems of weakening the carrier transport performance between molecules, reducing device performance, and increasing the distance between molecules. Good electron transport ability, high decomposition temperature and glass transition temperature, high thermal stability effect

Active Publication Date: 2017-06-30
CHINA UNIV OF MINING & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, when large substituent groups are introduced into the periphery of pyrene, the distance between molecules will be enlarged, and the carrier transport performance between molecules will be weakened, which will reduce the performance of the device to a certain extent.

Method used

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  • Bipolar-configuration pyrenyl blue-light emitting material containing benzimidazole unit, preparation method and application
  • Bipolar-configuration pyrenyl blue-light emitting material containing benzimidazole unit, preparation method and application
  • Bipolar-configuration pyrenyl blue-light emitting material containing benzimidazole unit, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1. Synthesis and property determination of compounds 3 and 4

[0037] 1. Synthetic route of compound 3 and 4

[0038] Synthesize compounds 3 and 4 according to the following reaction

[0039]

[0040] 1) Synthesis of 1,8-bis(4-tert-butylphenyl)pyrene (compound Py18)

[0041] Under the protection of nitrogen, 1,8-dibromopyrene (1.80g, 5mmol, 4-tert-butylphenylboronic acid (2.14g, 12mmol), tetrakis (triphenylphosphine) palladium Pd (PPh 3 ) 4 (0.12g, 0.1mmol) and 2M potassium carbonate solution (12mL) were dissolved in toluene (80mL) and refluxed for 24 hours. After the reaction, the mixture was poured into water, the organic layer was extracted with dichloromethane, and then with anhydrous MgSO 4 After drying, the solvent is removed by rotary evaporation. The crude product is loaded by dry method, and the mixture of n-hexane and dichloromethane is used as the eluent to pass through the silica gel column, and then the mixture of dichloromethane and ethanol (v:v=1:2) is r...

Embodiment 2

[0067] Example 2. Synthesis and property determination of compounds 9 and 10.

[0068] 1. Examples of synthetic routes of compounds 9 and 10:

[0069] Synthesize compounds 9 and 10 according to the following reaction

[0070]

[0071]

[0072] 1) Synthesis of 1-(4-phenyl)-1H-2-(3-bromophenyl)-benzimidazole (compound 3a)

[0073] A mixture of N-(4-phenyl)benzene-1,2-diamine (3.68g, 20mmol), 3-bromobenzaldehyde (3.70g, 20mmol) and sodium bisulfite (2.04g, 10mmol) was dissolved in DMF (80 mL) was stirred and refluxed in air for 1 h. After the reaction is finished, it is cooled to room temperature and the reaction liquid is poured into water to precipitate the product. After standing for a period of time, the product was filtered off with suction and washed with a small amount of methanol. Finally, the crude product is purified by silica gel column chromatography using a mixture of n-hexane and ethyl acetate (v:v=1:3) as an eluent to obtain a white powder solid product. Yield: 5.60 g,...

Embodiment 3

[0094] Example 3. Compounds 4 and 10 were selected to explore the electroluminescence properties of the materials, and organic electroluminescence devices were prepared by spin coating and thermal evaporation processes.

[0095] The structure of the organic electroluminescent device I is: ITO / PEDOT:PSS (40 nm) / NPB (30 nm) / 4or 10 (30 nm) / TPBI (20 nm) / LiF (1 nm) / Al (150 nm).

[0096] The structure of the organic electroluminescent device II is: ITO / PEDOT:PSS(40nm) / NPB(30nm) / 4or 10(30nm) / BCP(6nm) / LiF(1nm) / Al(150nm).

[0097] The substrate is made of glass sheet, the transparent conductive film is ITO film as the anode, the substrate is sequentially subjected to glass washing solution, deionized water cleaning, drying and ozone treatment, and then spin-coated a layer of 40nm thick polyethylene dioxythiophene-poly(benzene) Ethylene sulfonate) (PEDOT:PSS), and then dried in a drying oven at 120° for 30 minutes, and then placed in the vacuum chamber, when the vacuum reaches 4×10 –4 Pa unde...

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Abstract

The invention discloses a bipolar-configuration pyrenyl blue-light emitting material containing a benzimidazole unit, a preparation method and an application, and belongs to the field of organic electroluminescent materials and devices. The efficient pyrenyl blue-light emitting material is synthesized by introducing phenyl, alkyl phenyl or alkoxy phenyl groups to 1-position and 8-position of pyrene and introducing N-phenylbenzimidazole groups to 3-position and 6-position of pyrene. The pyrenyl blue-light emitting material has the advantages of simple and convenient synthesis, cheap raw materials and low cost; peripheral substituent groups can effectively inhibit intermolecular accumulation, and the solid-state luminous efficiency of the material can be as high as 85.43%. The heat stability of the material is high, and the material has higher decomposition temperature and glass-transition temperature; the material has excellent electron transport capacity, so that a device structure can be simplified. An electroluminescent device prepared from the pyrenyl blue-light emitting material as a luminescent layer as well as an electron transport layer has higher level in the aspects of luminance, efficiency, stability and the like, the electroluminescence spectrum of the material is in an area from sky blue to dark blue, and one excellent blue-light emitting material is provided for full-color display and lighting.

Description

Technical field [0001] The invention belongs to the field of organic electroluminescence materials, and specifically relates to a bipolar configuration pyrene-based blue light material containing benzimidazole units and a preparation method, and the application of the material in organic electroluminescence. Background technique [0002] The huge advantages of organic electroluminescent diodes (OLEDs) in flat panel displays and solid-state lighting have attracted the attention of scholars [Chem.Soc.Rev., 2011,40,3467-3482]. In order to promote the development of the field of organic electroluminescence, researchers are mainly devoted to designing and synthesizing excellent photoelectric functional materials and improving the preparation technology of devices. At present, many organic electroluminescent materials have been commercialized and are used in mobile phones and displays. For luminescent materials, high-efficiency red and green light have been continuously developed and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/18C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D235/18C09K2211/1044C09K2211/1007C09K2211/1011H10K85/622H10K85/6572H10K50/00
Inventor 倪中海张然张丽芳赵云
Owner CHINA UNIV OF MINING & TECH
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