Derivative containing phenanthroimidazole structure and organic light-emitting device thereof
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An organic light-emitting device, phenanthroimidazole technology, applied in the field of derivatives containing phenanthroimidazole structure and its organic light-emitting device, can solve the problems of low luminous efficiency, short device life, and OLED performance degradation
Inactive Publication Date: 2018-04-17
CHANGCHUN HYPERIONS TECH CO LTD
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[0004] At present, the hole mobility of hole transport materials used in OLED devices is generally much greater than the electron mobility of electron transport materials, which will directly lead to a significant decline in OLED performance, such as short device life and low luminous efficiency. Therefore, the design It has strong practical significance to develop electron transport materials with excellent performance
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Embodiment 1
[0051] Embodiment 1: the synthesis of compound 1
[0052]
[0053] (1) In a four-neck flask equipped with a thermometer, a stirrer, a water separator and a condenser, add compound a (47mmol, 14.30g), compound phenanthrene 9,10 diamine (45mmol, 9.37g), ethylene glycol Diethyl ether (250ml) and pyridine (0.2g), stirred and heated to 140°C, kept the temperature for 3 hours, stirred and cooled the reaction solution to 40°C, filtered, washed the filter cake with ethanol, washed with water, and dried to obtain compound 1-1 .
[0054] (2) in N 2 Under protection, compound 1-1 (0.05mol, 23.84g) and 200ml of dry THF treated with Na / benzophenone were added to a 500ml three-neck flask, the reaction system was cooled to -40°C, and freshly prepared formazan was slowly added dropwise. Grignard reagent THF solution (prepared by methyl bromide (0.25mol, 23.73g) and magnesium (0.3mol, 7.2g)), after the dropwise addition was completed, the reaction system was slowly raised to room temperat...
Embodiment 2
[0058] Embodiment 2: the synthesis of compound 2
[0059] According to the synthetic method of compound 1, compound 2 (12.44 g, 75%) was obtained.
[0060]
[0061] Mass Spectrum m / z: 552.18 (calculated: 552.17). Theoretical element content (%)C 39 h 24 N 2 S: C, 84.75; H; 4.38; N, 5.07; S, 5.80 Measured element content (%): C, 84.76; H, 4.37; N, 5.07; S, 5.80. The above results confirmed that the obtained product was the target product.
Embodiment 3
[0062] Embodiment 3: the synthesis of compound 5
[0063] According to the synthetic method of compound 1, compound 5 (13.56 g, 75%) was obtained.
[0064]
[0065] Mass Spectrum m / z: 602.19 (calculated: 602.18). Theoretical element content (%)C 43 h 26 N 2 S: C, 85.69; H, 4.35; N, 4.65; S, 5.32 Measured element content (%): C, 85.69; H, 4.34; N, 4.66; S, 5.32. The above results confirmed that the obtained product was the target product.
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Abstract
The invention provides a derivative containing a phenanthroimidazole structure and an organic light-emitting device thereof, and belongs to the technical field of organic photoelectric materials. Thederivative containing the phenanthroimidazole structure provided by the invention has the structure shown in formula (I), the phenanthroimidazole derivative belongs to a typical electron-deficient system and has a good electron-accepting capability, the derivative is also a polycyclic aromatic hydrocarbon system with a common plane in the spatial structure and has a suitable HOMO and LUMO energy level, and therefore the derivative has a good electron transfer capability and is an excellent electron transport material; and the molecular weight of the derivative is between 500 and 900, so that the glassy state conversion temperature is higher, and therefore the heat stability is good, and meanwhile, the vacuum evaporation film-forming property is good. The organic light-emitting device prepared from the derivative has the advantages of being high in efficiency, long in service life and superior to an existing common OLED (organic light emitting diode) device.
Description
technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a derivative containing a phenanthroimidazole structure and an organic light-emitting device thereof. Background technique [0002] The history of electroluminescent organic molecules can be traced back to the early 1960s. However, an important breakthrough in the research of organic light-emitting diodes (OLEDs) was that in 1987 Deng Qingyun and Steve Van Slyke of Kodak Company invented the vacuum evaporation method and in 1990 a research team at the University of Cambridge solved the common problem. Dissolution problems of conjugated polymers. Due to the characteristics of energy saving, fast response, stable color, strong environmental adaptability, no radiation, light weight and thin thickness, organic electroluminescent devices have a wide range of application markets. [0003] OLED optoelectronic functional materials applied to OLED devices can be ...
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