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Phenanthroimidazole-anthracene-diphenylamine derivative luminescent material and its application in the preparation of organic electroluminescent devices
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A technology of phenanthroimidazole and luminescent materials, applied in luminescent materials, electric solid devices, organic chemistry, etc., can solve the problems of high device driving voltage, difficult growth of single crystal, and no practical application
Active Publication Date: 2018-02-27
JILIN UNIV
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However, due to the difficulty of growing single crystals and the high driving voltage of the device (400-2000V), the process they used has almost no practical use
Method used
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Embodiment 1
[0023] Embodiment 1: the synthesis of compound M1:
[0024]
[0025] 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. Stop the reaction, pour the reaction mixture into distilled water, stir and filter, the gray filter cake of the gained is washed with water, glacial acetic acid, ethanol successively, after drying, obtain the phenanthroimidazole intermediate 1 (4.57g, productive rate 85% ).
[0026] The phenanthroimidazole intermediate 1 (5.00 g, 11.1 mmol) was dissolved in 150 ml of tetrahydrofuransolvent previously dehydrated, placed in a low-temperature reactor to maintain -78 ° C, degassed three times and then protected by nitrogen. After the system was stabilized, n-butyllithium (2.4M, 5.3 mL) was added dropwise into the above reaction system using a syringe, and stirred for three ...
Embodiment 2
[0029] Embodiment 2: the synthesis of compound M2:
[0030]
[0031] According to the synthesis of compound M1, the steps are the same, and 4-methylaniline is used instead of aniline to obtain white powder compound M2 (1.11g, yield 76%), and the molecular ionmass determined by mass spectrometry is: 727.41 (calculated value: 727.30 ); Theoretical element content (%) C 54 h 37 N 3 : C, 89.10; H, 5.12; N, 5.77; Measured element content (%): C, 89.02; H, 5.33; N, 5.64. The above analysis results indicated that the obtained product was the expected product.
Embodiment 3
[0032] Embodiment 3: the synthesis of compound M3:
[0033]
[0034] According to the synthesis of compound 1, the steps are the same, and aniline is replaced with 4-tert-butylaniline to obtain white powder compound M3 (1.11g, yield 72%), and the molecular ionmass determined by mass spectrometry is: 769.52 (the calculated value is: 769.35); theoretical element content (%) C 57 h 43 N 3 : C, 88.91; H, 5.63; N, 5.46; Measured element content (%): C, 90.02; H, 5.60; N, 5.37. The above analysis results indicated that the obtained product was the expected product.
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Abstract
A class of phenanthroimidazole-anthracene-diphenylamine derivative luminescent material with the following structural formula and its application in the preparation of organic electroluminescent devices belongs to the technical field of organic electroluminescence. The outstanding feature of the present invention is that the phenanthreneimidazole group and the 9-dianiline anthracene group are connected together through a benzene ring. This type of molecule not only inherits the high fluorescencequantum efficiency of the anthracene group, but also inherits the The advantages of good thermal stability and high electron mobility of the imidazole group constitute a bipolar transport luminescent body with good carrier transport characteristics. The turn-on voltage of the electroluminescent device prepared by this kind of material is 2.4 ~2.5 volts, greatly improving the electroluminescent performance of the device. This type of luminescent material can be used to prepare organic electroluminescent devices, and the electroluminescent devices are used to prepare illumination sources or flat panel displays.
Description
technical field [0001] The invention belongs to the technical field of organic electroluminescence, and in particular relates to a class of phenanthroimidazole-anthracene-diphenylamine derivative luminescent material and its application in the preparation of organic electroluminescence 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, due to the difficulty of growing single crystals and the high driving voltage of the device (400-2000V), the process they used has almost no practical use. 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 light-emitting layer, and ind...
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