Aggregation-induced luminescent materials of tristyryl-substituted phenanthroimidazole derivatives and their application in the preparation of organic electroluminescent devices

A technology of aggregation-induced luminescence and tristyryl-based, which is applied in luminescent materials, electric solid-state devices, semiconductor devices, etc., and can solve the problems of high device driving voltage, no practical use, and difficulty in growing single crystals.

Active Publication Date: 2018-07-06
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, because single crystals are difficult to grow and the device driving voltage is high (400-2000V), the process they use has almost no practical use

Method used

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  • Aggregation-induced luminescent materials of tristyryl-substituted phenanthroimidazole derivatives and their application in the preparation of organic electroluminescent devices
  • Aggregation-induced luminescent materials of tristyryl-substituted phenanthroimidazole derivatives and their application in the preparation of organic electroluminescent devices
  • Aggregation-induced luminescent materials of tristyryl-substituted phenanthroimidazole derivatives and their application in the preparation of organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: the synthesis of compound 1:

[0028]

[0029] Add phenanthrenequinone (12mmol), p-bromobenzaldehyde (12mmol), aniline (32mmol), ammonium acetate (62.5mmol), acetic acid (50mL) into the there-necked flask, N 2 Under protection, it was heated to reflux in an oil bath at 123°C for 12h. The reaction was stopped, the reaction mixture was poured into distilled water, stirred and filtered, the gray filter cake obtained was washed with water, glacial acetic acid and ethanol successively, and after drying, the phenanthroimidazole intermediate (4.57g, yield 85%) obtained by para-bromine substituted . The para-bromo-substituted phenanthroimidazole obtained above (0.90g, 2mmol), 2-(4-(2,2-distyryl)phenyl-4,4,5,5-tetramethyl-1, 3,2-dioxaborolane (0.84g, 2.2mmol), potassium carbonate (1.66g, 12mmol), tetrakis (triphenylphosphine) palladium (23.1mg, 0.02mmol) mixed with 20ml of toluene and 6ml of water were added In a round bottom flask. After degassing three time...

Embodiment 2

[0030] Embodiment 2: the synthesis of compound 2:

[0031]

[0032] According to the synthesis of compound 1, the steps are the same, and p-methylaniline is used instead of aniline to obtain white powder compound 2 (1.05g, yield 82%). The molecular ion mass determined by mass spectrometry is: 638.18 (calculated value: 638.27) ; Theoretical element content (%) C 48 h 34 N 2 : C, 90.25; H, 5.36; N, 4.39; Measured element content (%): C, 90.10; H, 5.33; N, 4.56. The above analysis results indicated that the obtained product was the expected product.

Embodiment 3

[0033] Embodiment 3: the synthesis of compound 3:

[0034]

[0035] According to the synthesis of compound 1, the steps are the same, and aniline is replaced by p-tert-butylaniline to obtain white powder compound 3 (1.06g, yield 78%), and the molecular ion mass determined by mass spectrometry is: 680.55 (calculated value: 680.32 ); Theoretical element content (%) C 51 h 40 N 2 : C, 89.96; H, 5.92; N, 4.11; Measured element content (%): C, 90.02; H, 5.80; N, 4.17. The above analysis results indicated that the obtained product was the expected product.

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Abstract

The invention relates to an aggregation-induced luminescence material of tristyryl-substituted phenanthroimidazole derivatives and its application in the preparation of organic electroluminescent devices, belonging to the technical field of organic electroluminescence. The structural formula of the luminescent material is as follows. Its outstanding feature is that the phenanthroimidazole group and the triphenylethylene group are connected together through a benzene ring. This type of molecule not only inherits the good thermal stability of phenanthroimidazole, but also has a high It has the advantages of electron mobility and high fluorescence quantum efficiency, and also inherits the property of triphenylethylene group aggregation-induced luminescence, which overcomes the problem of fluorescence quenching caused by aggregation. At the same time, the molecule has a large twisted structure, which can ensure that the compound has a high fluorescence quantum efficiency in the solid state. The electroluminescent device prepared by using this type of material as the light-emitting layer has excellent performance. The electroluminescent device is used for Prepare an illumination source or a flat panel display.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence, and in particular relates to a kind of aggregation-induced luminescent material of tristyryl-substituted phenanthroimidazole derivatives and its application in preparing organic electroluminescent devices. Background technique [0002] Pope et al first reported the phenomenon of organic electroluminescence in the early 1960s. They observed the blue light emitted by anthracene when a high voltage of 400 volts was applied to both sides of anthracene single crystal. However, because single crystals are difficult to grow and the driving voltage of the device is very high (400-2000V), the technology they use has almost no practical application. Until 1987, C.W.Tang et al. of Kodak Corporation of the United States used ultra-thin film technology to use aromatic amines with better hole transport effects as the hole transport layer, aluminum complexes of 8-hydroxyquinoline as the ligh...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/02C09K11/06H01L51/54
CPCC09K11/06C07D235/02C09K2211/1044H10K85/6572
Inventor 王悦叶开其
Owner JILIN UNIV
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