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A fluorene-containing phenanthroimidazole derivative, crystal, preparation method and application thereof
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A technology of phenanthroimidazoles and phenanthroimidazoles, which is applied in the field of organic electroluminescent devices, can solve the problems of low luminous intensity, poor thermal stability, and short fluorescence lifetime, and achieve high luminous intensity, good thermal stability, and fluorescent long life effect
Active Publication Date: 2020-05-05
GUANGDONG UNIV OF TECH
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[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
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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 phenanthroimidazole derivative, crystal and its preparation method and application. The structural formula of the fluorene-containing phenanthroimidazole derivative is shown in formula (I): The invention provides a fluorene-containing phenanthroimidazole derivative, and the crystal prepared by the fluorene-containing phenanthroimidazole derivative has the advantages of high luminous intensity, long fluorescence lifetime, good thermal stability and high fluorescence quantum yield . The fluorene-containing phenanthroimidazole derivative crystal has significant economic value in the preparation of light-emitting materials, light-emitting devices, or smart materials in an off / on manner. At the same time, the invention realizes the controllable preparation of fluorene-containing phenanthroimidazole derivative crystals.
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...
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