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Organic blue light micromolecule based on phenanthroimidazole and application of organic blue light micromolecule in preparation of non-doped organic electroluminescent device

The technology of an electroluminescent device and phenanthroimidazole is applied in the application field of preparing non-doped organic electroluminescent devices, which can solve the problems of low color purity, roll-off, and low device efficiency, and achieve simple and high-efficiency preparation methods. Fluorescence quantum yield, the effect of realizing saturated blue light emission

Pending Publication Date: 2022-07-22
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The invention aims to solve the problems of low color purity, low device efficiency and serious roll-off of organic blue light small molecule materials in OLEDs in the field of non-doped devices

Method used

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  • Organic blue light micromolecule based on phenanthroimidazole and application of organic blue light micromolecule in preparation of non-doped organic electroluminescent device
  • Organic blue light micromolecule based on phenanthroimidazole and application of organic blue light micromolecule in preparation of non-doped organic electroluminescent device
  • Organic blue light micromolecule based on phenanthroimidazole and application of organic blue light micromolecule in preparation of non-doped organic electroluminescent device

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: the preparation of compound P1 of this embodiment, the steps are as follows:

[0032]

[0033]Synthesis of M1: M1 was synthesized by one-pot method. In a 100 mL round-bottomed flask, phenanthrenequinone (2.08 g, 10.00 mmol), aniline (3.73 g, 40.00 mmol), 3,5-dibromobenzaldehyde (2.64 g, 10.00 mmol) and ammonium acetate (3.85 g, 50 mmol) were dissolved in 50 mL of glacial acetic acid solution, and heated to reflux at 120° C. for 2 hours. After the reaction, the reaction was quenched with water, and the solid was obtained by suction filtration, washed with water, glacial acetic acid and ethanol successively to obtain a crude product, which was separated and purified by column chromatography (petroleum ether: dichloromethane volume ratio=2:1) ​​to obtain a white solid ( 4.23 g, yield: 80%). Mass MALDI-TOF (m / z) [M + ]: The measured value is 528.77, the theoretical value is 528.25.

[0034]

[0035] Synthesis of M2: M1 (5.28 g, 10.00 mmol), pinacol di...

Embodiment 2

[0038] Embodiment 2: the preparation of this embodiment compound P2, its steps are as follows:

[0039]

[0040] Synthesis of M3: M3 was synthesized by one-pot method. In a 100 mL round bottom flask, phenanthrenequinone (2.08 g, 10.00 mmol), aniline (3.73 g, 40.00 mmol), 4-bromobenzaldehyde (1.85 g, 10.00 mmol) and Ammonium acetate (3.85 g, 50 mmol) was dissolved in 50 mL of glacial acetic acid solution, and heated under reflux at 120° C. for 2 hours. After the reaction, the reaction was quenched with water, and the solid was obtained by suction filtration, washed with water, glacial acetic acid and ethanol successively to obtain a crude product, which was separated and purified by column chromatography (petroleum ether: dichloromethane volume ratio=2:1) ​​to obtain a white solid ( 3.59 g, yield: 80%). Mass MALDI-TOF (m / z) [M + ]: The measured value is 449.55, the theoretical value is 449.35.

[0041]

[0042] Synthesis of M4: M3 (4.49 g, 10.00 mmol), pinacol diborona...

Embodiment 3

[0045] Embodiment 3: the preparation of this embodiment compound P3, its steps are as follows:

[0046]

[0047] The present embodiment is basically the same as embodiment 2, and its difference is: in this example, 5'-bromo-terphenyl needs to be replaced with 4-bromo-5'-phenyl-1,1' of equivalent amount: 3',1"-terphenyl as a white powdery solid (1.35 g, yield: 80%). Mass spectrum: MALDI-TOF (m / z) [M + ]: The measured value is 674.27, the theoretical value is 674.85; elemental analysis: C 51 H 34 N 2 Theorized C 90.77, H 5.08, N 4.15; Measured C 90.73, H 5.09, N 4.17.

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Abstract

The invention discloses organic blue light micromolecules based on phenanthroimidazole and application of the organic blue light micromolecules in preparation of non-doped organic electroluminescent devices, and belongs to the technical field of organic photoelectric materials. The phenanthroimidazole with a rigid structure is connected with a neutral group or a weak acceptor group in a reasonable manner, so that the excited state of the molecule has a weak charge transfer state characteristic, and the color purity of blue light emission is improved. Meanwhile, substituent groups introduced to phenanthroimidazole have certain steric hindrance to inhibit interaction between molecules, and the mutual quenching process between molecules can be relieved to a certain extent. The phenanthroimidazole derivative has a bipolar transmission property and excellent thermal stability and chemical stability. A non-doped electroluminescent device prepared from the derivative has the advantages of low opening, low roll-off, high efficiency, high color purity and the like, and further development of organic electroluminescence is promoted.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronic materials, in particular to a phenanthroimidazole-based organic blue light small molecule and its application in preparing non-doped organic electroluminescence devices. Background technique [0002] Since the invention of Organic Light Emitting Diode (OLED) by Dr. Deng Qingyun of Kodak Company in 1987, the research upsurge of OLED materials and devices has been set off around the world. OLED has developed rapidly due to its advantages of flexibility, bendability, wide viewing angle, and energy saving, and corresponding commercial products have been applied in the field of display and lighting. Blue light material is one of the essential three primary colors in full-color display. In addition, due to the wide band gap of blue light itself, it can be used as the host to excite other colors through energy transfer, which not only enables the component manufacturing process of full-col...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/02C09K11/06H01L51/54H01L51/50
CPCC07D235/02C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1044H10K85/624H10K85/615H10K85/6572H10K50/11
Inventor 路萍杜春亚刘辉程壮
Owner JILIN UNIV
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