Pyrene and imidazole derivative and preparation method and application thereof

A technology of pyrenimidazole and its derivatives, which is applied in the field of pyrenimidazole derivatives and its preparation, and can solve problems such as unreachable luminous efficiency

Inactive Publication Date: 2017-09-05
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 dr

Method used

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  • Pyrene and imidazole derivative and preparation method and application thereof
  • Pyrene and imidazole derivative and preparation method and application thereof
  • Pyrene and imidazole derivative and preparation method and application thereof

Examples

Experimental program
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Embodiment 1

[0082] The synthesis of embodiment 1 compound 1:

[0083] (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 The reaction was carried out at 40° C. for 24 hours. After separation and purification, orange powdery 4,5-pyrene diquinone was obtained.

[0084] (2) Take 4,5-pyrenediquinone (2.32g, 10mmol), aniline (4.65g, 50mmol), 4-bromobenzaldehyde (5.46g, 30mmol) and ammonium acetate (3.85g, 50mmol) in a 250mL round bottom In the flask, react at 120° C. for 3 hours under nitrogen protection. Then distilled water was added to the reaction system, and the precipitated crude product was obtained by filtration, which was separated by column chromatography to obtain 9-(4-bromo)-9-hydro-pyreneimidazole.

[0085] (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...

Embodiment 2

[0087] The synthesis of embodiment 2 compound 2

[0088] 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 by using 10-(4-pinacol borate)-9-hydro-pyrenezimidazole and bromobenzene as raw materials according to the synthesis method of compound 1 step (4) in Example 1. Using MALDI-TOF to identify the compound, the molecular formula is C 35 h 22 N 2 , detected value [M+]=470.19, theoretical value 470.56.

Embodiment 3

[0089] The synthesis of embodiment 3 compound 3

[0090] 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 4-bromoaniline as raw materials according to the synthesis method of compound 1 step (2) in Example 1. Step (3) is prepared by using 9,10-(4-bromo)-9-hydro-pyrene imidazole and biboronic acid pinacol ester as raw materials according to the synthetic method of compound 1 step (3) in Example 1. Step (4) is prepared by using 9,10-(4-pinacol borate)-9-hydro-pyrenimidazole and bromobenzene as raw materials according to the synthesis method of compound 1 step (4) in Example 1. Using MALDI-TOF to identify the compound, the molecular formula is C 41 h 26 N 2 , detected value [M+]=546.83, theoretical value 546.66.

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Abstract

The invention relates to a pyrene and imidazole derivative and a preparation method and application thereof. The bridging mode of C2 atom and N1 atom of an imidazole group is changed to form the pyrene and imidazole derivative with the structural formula as shown in (A), the pyrene and imidazole derivative is a novel blue-light emitting material, and owing to introduction of the imidazole group, the level structure and the electron transmission performance of the pyrene and imidazole derivative can be regulated. The pyrene and imidazole derivative can serve as an organic electroluminescent material to prepare an organic electroluminescent device, and the prepared device has the characteristics of high efficiency, low driving voltage and the like.

Description

technical field [0001] The invention belongs to the field of organic photoelectric materials, and in particular relates to a pyrenimidazole derivative and a preparation method and application thereof. 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 ...

Claims

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Application Information

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IPC IPC(8): C07D235/02C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D235/02C09K2211/1044H10K85/622H10K85/615H10K85/6572H10K50/11
Inventor 路萍康亮亮
Owner JILIN UNIV
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