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1,12-iminobenzo[c]phenanthrene compound, intermediate, preparation method and application of compound

A technology of iminobenzene and compounds, which is applied in the compound field of the main material of the light-emitting layer of organic electroluminescent devices, and can solve the problems of short lifespan and low efficiency of light-emitting devices

Active Publication Date: 2014-02-12
KUNSHAN VISIONOX DISPLAY TECH +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The technical problem to be solved by the present invention is that the existing host material of the light-emitting layer cannot be adapted to the blue phosphorescent dye, which leads to low efficiency and short life of the organic electroluminescent device, thus providing a new blue phosphorescent light-emitting layer 1,12-iminobenzo[c]phenanthrene compounds as host materials

Method used

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  • 1,12-iminobenzo[c]phenanthrene compound, intermediate, preparation method and application of compound
  • 1,12-iminobenzo[c]phenanthrene compound, intermediate, preparation method and application of compound
  • 1,12-iminobenzo[c]phenanthrene compound, intermediate, preparation method and application of compound

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Embodiment 1 to Embodiment 3

[0119] Example 1 to Example 3 are preparation examples of the intermediate M5 of the present invention:

Embodiment 1

[0121] The intermediate represented by the preparation formula (M5) in this embodiment:

[0122]

[0123] The synthetic route is as follows:

[0124]

[0125] The preparation method is:

[0126] (1) Synthesis of M1

[0127]

[0128] In a 500ml three-necked flask, add 22.1g 1-bromo-2-methylnaphthalene, 50ml concentrated sulfuric acid, 100ml 1,2-dichloroethane, ice salt bath to control the temperature below 0℃, and slowly drip while stirring Add 9.3g 68% nitric acid, after the addition, keep 0~5℃ and stir for 2 hours, slowly pour into 300ml ice water, separate, wash the organic layer with water, wash with 5% sodium carbonate, wash with water, dry with magnesium sulfate, and concentrate to dry After separation by silica gel column chromatography, the volume ratio of ethyl acetate: petroleum ether = 1:2 was eluted, and the light yellow product M1 14.2g was obtained, MS (m / e): 267, melting range 102~103.5℃, yield 53.4 %.

[0129] (2) Synthesis of M2

[0130]

[0131] Add 14g M1, 300ml carb...

Embodiment 2

[0142] This embodiment prepares the intermediate represented by formula (M5), and the basic steps are the same as in embodiment 1, wherein:

[0143] In step (1), the stirring time is 1.5 hours, the volume ratio of ethyl acetate: petroleum ether = 1:1.6 elution, and the control temperature is -10°C to 0°C.

[0144] In step (2), the reflux time is 6 hours, and the volume ratio of ethyl acetate: petroleum ether = 1:4;

[0145] Step (3) In the step (3), the reaction was refluxed in an oil bath for 2 hours and then the temperature was lowered, and the solvent, sodium hydride, 2-bromo-3-nitrobenzaldehyde was added, and the temperature was slowly raised to 42°C for 1.5 hours, and then to 50°C for 2.5 hours. The reaction was then refluxed for 7 hours, the temperature was lowered, and anhydrous ethanol was slowly added to decompose excess sodium hydride and stirred, then the reaction solution was poured into water and stirred for 2.5 hours, extracted with dichloromethane, washed, dried, and s...

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Abstract

The invention discloses a 1,12-iminobenzo[c]phenanthrene compound, the compound has a structural formula represented by a formula (I), wherein Ar1, Ar2 and Ar3 are respectively and independently selected from C6-C50 aryl, substituted C6-C50 aryl or C1-C20 alkyl. The compound can be used as main body material of a fluorescence luminescent layer and a phosphorescence luminescent layer of an organic electroluminescence device, the brightness and luminescent efficiency of the organic electroluminescence device are improved, the driving voltage is reduced, and the service life of the organic electroluminescence device is prolonged.

Description

Technical field [0001] The present invention relates to an organic compound, in particular to a compound used for the host material of the light-emitting layer of an organic electroluminescence device; the present invention also relates to an intermediate of the compound and a preparation method thereof and its application in an organic electroluminescence device. Background technique [0002] Organic electroluminescence (hereinafter referred to as OLED) and the corresponding research began as early as the 1960s. In 1963, P. Pope et al. first discovered the electroluminescence phenomenon of organic single crystal anthracene, but due to the limitation of technical conditions, its driving voltage was as high as 400V, which failed to attract widespread attention. In 1987, C.W.Tang of Kodak Company in the United States used vapor deposition Alq 3 An amorphous film-type organic electroluminescent device was made, and the driving voltage was reduced to less than 20V, before OLED attrac...

Claims

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Application Information

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IPC IPC(8): C07D221/18C07D401/14C07D401/10C07D401/04H01L51/54H01L51/50
CPCC07D221/18C07D401/04C07D401/10C07D401/14C09K2211/1029H10K85/615H10K85/626H10K85/6572
Inventor 邱勇王占奇段炼
Owner KUNSHAN VISIONOX DISPLAY TECH
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