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Fluorene-containing phenanthrene imidazole derivative and crystal as well as preparation method and application thereof

A technology of phenanthroimidazoles and phenanthroimidazoles, which is applied in the field of organic electroluminescent devices, can solve the problems of short fluorescence lifetime, low luminous intensity, poor thermal stability, etc., and achieve high luminous intensity, high fluorescence quantum yield, good thermal stability

Active Publication Date: 2019-02-12
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to overcome the defects of low luminous intensity, short fluorescence lifetime and poor thermal stability of the luminescent material described in the above prior art, the present invention provides a phenanthroimidazole derivative containing fluorene

Method used

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  • Fluorene-containing phenanthrene imidazole derivative and crystal as well as preparation method and application thereof
  • Fluorene-containing phenanthrene imidazole derivative and crystal as well as preparation method and application thereof
  • Fluorene-containing phenanthrene imidazole derivative and crystal as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] A fluorene-containing phenanthroimidazole derivative prepared by the following method:

[0049] (1) Preparation of 4-(9H-fluoren-2-yl)benzaldehyde:

[0050] 2.73 g of 2-bromofluorene, 3.34 g of p-formylphenylboronic acid, 0.5 g of tetrakis(triphenylphosphine) palladium, 4.62 g of potassium carbonate, 80 mL of tetrahydrofuran and 20 mL of H 2 O, was added to a 250 mL round bottom flask, the temperature was 70 °C, under the protection of nitrogen, the reaction was heated and stirred under reflux for 12 h. Cool to room temperature and extract with dichloromethane to give a brown solid after desolvation. Using dichloromethane and n-hexane as eluents, 2.52 g of white 4-(9H-fluoren-2-yl)benzaldehyde was obtained by column chromatography with a yield of 84%.

[0051] (2) Preparation of phenanthroimidazole derivatives containing fluorene:

[0052] Add 0.6 g of 4-(9H-fluoren-2-yl)benzaldehyde, 0.32 g of 9,10-phenanthrenequinone, 0.54 g of aniline, 0.39 g of ammonium acetate a...

Embodiment 2

[0056] The difference between this example and Example 1 is that the catalyst in step (1) of this example is 1, 1-bis(diphenylphosphino)ferrocenepalladium dichloride, and the solvent is a mixed solvent of DMF and water .

[0057] Other conditions and operation steps are identical with embodiment 1.

[0058] The yield of 4-(9H-fluoren-2-yl)benzaldehyde obtained in this example was 64%.

Embodiment 3

[0060] The difference between this example and Example 1 is that, in the preparation of the fluorene-containing phenanthroimidazole derivative crystal of this example, the crystal was heated to 300°C.

[0061] Other conditions and operation steps are identical with embodiment 1.

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Abstract

The invention discloses a fluorene-containing phenanthrene imidazole derivative and a crystal as well as a preparation method and application thereof. A structural formula of the fluorene-containing phenanthrene imidazole derivative is shown as a formula (I) (the formula (I) is shown in the description). By means of the fluorene-containing phenanthrene imidazole derivative disclosed by the invention, the crystal prepared from the fluorene-containing phenanthrene imidazole derivative has the advantages of high light intensity, long fluorescence life, good heat stability and high fluorescence quantum yield. The fluorene-containing phenanthrene imidazole derivative crystal has obvious economical value in the application aspects of preparing luminescent materials, luminescent devices, off / on type intelligent materials or the like. Meanwhile, the invention achieves controllable preparation of the fluorene-containing phenanthrene imidazole derivative crystal.

Description

technical field [0001] The invention relates to the field of organic electroluminescent devices, and more specifically, to a fluorene-containing phenanthroimidazole derivative, a crystal, a preparation method and application thereof. Background technique [0002] With the rise of high-tech technologies such as large-screen smartphones, tablet computers, and wearable devices, Organic Light-Emitting Diodes (OLEDs) have the advantages of self-illumination, wide viewing angle, low power consumption, fast response time, and thin thickness. , can realize the advantages of flexibility, etc., it is regarded as a new generation of display products with great development prospects in the diversified flat panel display market, and is known as "dream display". Organic electroluminescent devices (OLEDS) have shown strong competitiveness in applications due to their unique advantages, but as one of the three primary colors (blue, green, red), blue light devices are still inferior to the o...

Claims

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Application Information

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IPC IPC(8): C07D235/02C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D235/02C09K2211/1007C09K2211/1011C09K2211/1044H10K85/615H10K85/6572H10K50/11
Inventor 陈国威霍延平詹迎迎籍少敏潘成强杨庆旦孙建伟
Owner GUANGDONG UNIV OF TECH
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