Derivative containing bispyrenyl imidazole, and preparation method and application thereof

A technology of pyreneimidazole and derivatives is applied in the field of derivatives containing pyreneimidazole and the preparation thereof, and can solve the problems of unachieved luminous efficiency and the like

Inactive Publication Date: 2017-08-04
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although the luminous efficiency and device life at this time have not reached the level of practical application, this brand-new device structure and low driving voltage have given people a new understanding of electroluminescence, and it has also paved the way for people to study electroluminescence later. Foundation

Method used

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  • Derivative containing bispyrenyl imidazole, and preparation method and application thereof
  • Derivative containing bispyrenyl imidazole, and preparation method and application thereof
  • Derivative containing bispyrenyl imidazole, and preparation method and application thereof

Examples

Experimental program
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Embodiment 1

[0079] The synthesis of embodiment 1 compound 1:

[0080] (1) Add elemental pyrene (4.02g) and sodium periodate (20g) into a 500mL round bottom flask, add 100mL distilled water and 100mL acetonitrile solution, add catalyst RuCl 3 , reacted at 30°C for 12 hours. After separation and purification, orange powdery 4,5-pyrene diquinone was obtained.

[0081] (2) Get 4,5-pyrene diquinone (2.32g), aniline (4.65g), 4-bromobenzaldehyde (5.46g) and ammonium acetate (3.85g) in a 250mL round bottom flask, under nitrogen protection, The Debus-Radziszewski reaction was performed at 120°C for 2 hours. Then distilled water was added to the reaction system, and the precipitated crude product was obtained by filtration, and 9-(4-bromo)-9-hydrogen-pyrenimidazole was obtained by separation as light yellow powder.

[0082] (3) Take 9-(4-bromo)-9-hydrogen-pyrene imidazole (4.73g), biboronic acid pinacol ester (3.81g) and newly prepared potassium carbonate solution (16mL, 2mol / L) Add to 250mL ro...

Embodiment 2

[0084] The synthesis of embodiment 2 compound 2

[0085] Step (1) was prepared according to the synthesis method of compound 1 step (1) in Example 1. Step (2) is prepared by using 4,5-pyrenediquinone, benzaldehyde and 4-bromoaniline as raw materials according to the synthesis method of compound 1 step (2) in Example 1. Step (3) is prepared by using 10-(4-bromo)-9-hydrogen-pyrenimidazole and biboronic acid pinacol ester as raw materials according to the synthesis method of compound 1 step (3) in Example 1. Step (4) is prepared according to the synthesis method of compound 1 step (4) in Example 1 using 10-(4-pinacol borate)-9-hydrogen-pyrene imidazole and 1,4-dibromobenzene as raw materials . Using MALDI-TOF to identify the compound, the molecular formula is C 64 h 38 N 4 , detected value [M+]=862.83, theoretical value 863.01.

Embodiment 3

[0086] The synthesis of embodiment 3 compound 3

[0087] Step (1) was prepared according to the synthesis method of compound 1 step (1) in Example 1. Step (2) is prepared by using 4,5-pyrenediquinone, 4-bromobenzaldehyde and aniline as raw materials according to the synthesis method of compound 1 step (2) in Example 1. Step (3) is prepared by using 9-(4-bromo)-9-hydrogen-pyrenimidazole and biboronic acid pinacol ester as raw materials according to the synthesis method of compound 1 step (3) in Example 1. Step (4) is prepared according to the synthesis method of compound 1 step (4) in Example 1 using 9-(4-pinacol borate)-9-hydrogen-pyrene imidazole and 1,4-dibromonaphthalene as raw materials . Using MALDI-TOF to identify the compound, the molecular formula is C 68 h 40 N 4 , detected value [M+]=913.24, theoretical value 913.07.

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Abstract

The invention relates to a derivative containing bispyrenyl imidazole, and a preparation method and an application thereof. The bridging mode of the C2 atom and the N1 atom in an imidazolyl group is changed o form the derivative containing bispyrenyl imidazole, the structure of the derivative containing bispyrenyl imidazole is represented by formula (A) or formula (B), the derivative containing bispyrenyl imidazole is a novel blue light material, and the imidazolyl group is introduced to adjust the energy level structure and the electron transport property of the above compound. The derivative containing bispyrenyl imidazole can be used for making organic electroluminescent device as an organic electroluminescent material, and the made devices have the characteristics of high brightness, high efficiency and low driving voltage.

Description

technical field [0001] The invention belongs to the field of organic photoelectric materials, in particular to a derivative containing pyrenimidazole and its preparation method and application. Background technique [0002] The research work of organic electroluminescence can be traced back to the 1960s. In 1963, Pope et al. used electrolyte solution as an electrode, applied a voltage of 400V on both sides of anthracene single crystal, and observed the electroluminescence phenomenon of anthracene single crystal. In 1969, Dresener et al. introduced solid electrodes into electroluminescent devices, which played a certain role in promoting the development of electroluminescence. In 1982, Vincett et al. used metal materials as electrodes (aluminum cathode and gold anode) and anthracene thin film as light-emitting layer to prepare electroluminescent devices, which greatly reduced the driving voltage to about 30V. [0003] Although the luminous efficiency and device life at this...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/02C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D235/02C09K2211/1011C09K2211/1007C09K2211/1044H10K85/622H10K85/615H10K85/6572H10K50/11
Inventor 路萍康亮亮
Owner JILIN UNIV
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