2,6,6,8-tetra-substituted-6h-benzo[cd]pyrene compound and organic electroluminescence device containing same

A pyrene compound and tetra-substituted technology, which is applied in the field of organic compounds to achieve the effects of reducing driving voltage, low power consumption and low voltage

Active Publication Date: 2015-05-20
BEIJING ETERNAL MATERIAL TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, there is still much room for improvement in the luminescence performance of existing organic electroluminescent materials, and the industry urgently needs to develop new organic electroluminescent materials

Method used

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  • 2,6,6,8-tetra-substituted-6h-benzo[cd]pyrene compound and organic electroluminescence device containing same
  • 2,6,6,8-tetra-substituted-6h-benzo[cd]pyrene compound and organic electroluminescence device containing same
  • 2,6,6,8-tetra-substituted-6h-benzo[cd]pyrene compound and organic electroluminescence device containing same

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0066] Synthesis Example 1: Synthesis of Intermediate M1

[0067]

[0068] (1) Synthesis of compound (M1-a)

[0069] In a 250 ml three-necked flask, add 1.12 g of magnesium chips, 5 ml of dry tetrahydrofuran, add a little dibromoethane to initiate the reaction, then add dropwise a solution of 9 g of 1-bromo-2-methylnaphthalene in 15 ml of tetrahydrofuran under reflux, and add Complete and then reflux for 30 minutes, down to room temperature, pour out the supernatant for later use.

[0070] In another 500ml three-necked flask, under nitrogen protection, add 13.8g of o-dibromobenzene, 20ml of dry toluene, 0.32g of 1,3-bisdiphenylphosphinopropane nickel chloride, and add dropwise at a controlled temperature of 30°C to prepare The Grignard reagent was added at 30°C and then stirred for 5 hours to stop the reaction, added ammonium chloride solution for hydrolysis, and the organic layer was washed with water and then separated by silica gel column chromatography. The volume rati...

Synthetic example 2

[0079] Synthesis Example 2: Synthesis of Intermediate M2

[0080]

[0081] (1) Synthesis of compound (M2-a)

[0082] In a 100ml three-necked flask, add 1.29g 1,7,7-trimethyl-7-hydrogen-benzo[d,e]anthracene, 20ml dichloromethane, and add 1.92g liquid bromine dropwise at 0-5°C After adding 5 ml of dichloromethane solution, slowly rise to 25 ° C for 2 hours, pour into 50 ml of water, separate liquid, separate by silica gel column chromatography, elute with petroleum ether, and concentrate the eluent to obtain 1.9 g of light yellow solid, MS (m / e): 416, yield 91.3%.

[0083] (2) Synthesis of compound (M2-b)

[0084]500ml three-necked flask, add 6.33g 3,9-dibromo-1,7,7-trimethyl-7-hydrogen-benzo[d,e]anthracene, 300ml carbon tetrachloride, 5.58g N-bromo Substitute succinimide, 0.1g benzoyl peroxide, heat to reflux for 6 hours, filter while hot, concentrate the mother liquor to dryness, add 230ml glacial acetic acid, 10.05g anhydrous potassium acetate, reflux for 3 hours, cool ...

Synthetic example 3

[0087] Synthesis Example 3: Synthesis of Intermediate M3

[0088] The synthetic route is the same as the preparation of M1, just change the acetone in the step (2) into benzophenone, obtain product 2-bromo-6,6-diphenyl-6H-benzo[cd]pyrene 2.03g, MS ( m / e): 470.

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Abstract

The invention discloses a 2,6,6,8-tetra-substituted-6H-benzo[cd]pyrene compound. The compound has the structural general formula as shown in the formula (I), wherein A1 and A2 are respectively and independently selected from C6-C50 aromatic alkyls and substituted C6-C50 aromatic alkyls; and X is selected from C6-C50 aromatic alkyls, substituted C6-C50 aromatic alkyls and C1-C20 alkyls or forms a ring compound after being connected through other groups. The compound can be used as a main material of a fluorescent layer or a phosphorescent layer of an organic electroluminescence device; and by using the compound, the brightness and light-emitting efficiency of the organic electroluminescence device can be increased, the driving voltage of the organic electroluminescence device can be reduced, and the service life of the organic electroluminescence device can be prolonged.

Description

technical field [0001] The invention relates to an organic compound, which can be used as a host material for a light-emitting layer of an organic electroluminescent device; the invention also relates to the application of the compound in an organic electroluminescent device. Background technique [0002] At present, with the continuous advancement of OLED technology in the two major fields of lighting and display, people are paying more attention to the research on its core materials. An organic electroluminescent device with high efficiency and long life is usually the result of an optimized combination of device structure and various organic materials. As a result, this provides great opportunities and challenges for chemists to design and develop functionalized materials with various structures. Common functional organic materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materia...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C13/72C07C13/62C07C1/32C09K11/06H01L51/54
Inventor 范洪涛李艳蕊张向慧任雪艳
Owner BEIJING ETERNAL MATERIAL TECH
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