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

A pyrene-based compound, four-substitution technology, applied in the field of new organic compounds, to achieve the effect of low driving voltage and high luminous efficiency

Active Publication Date: 2015-05-20
BEIJING ETERNAL MATERIAL TECH
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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 light-emitting properties of existing functionalized organic materials, and the industry urgently needs to develop new host materials for the light-emitting layer, light-emitting dyes, hole-transport materials, and hole-injection 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

[0096] This synthetic example prepares the intermediate shown in formula (M1), and synthetic route is as follows:

[0097]

[0098] The preparation method is:

[0099] (1) Synthesis of compound (M1-a)

[0100] 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.

[0101] 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...

Synthetic example 2

[0111] This synthesis example prepares the intermediate shown in formula (M2), and synthetic route is as follows:

[0112]

[0113] (1) compound 3 shown in formula (M2-a), the synthesis of 9-bis-bromo-1,7,7-trimethyl-7-hydrogen-benzo[d, e]anthracene

[0114] In a 100 ml three-necked flask, add 1.29 g of compound 1,7,7-trimethyl-7-hydrogen-benzo[d,e]anthracene shown in formula (M1-b), 20 ml of dichloromethane, control 0 Add dropwise 1.92g of liquid bromine in 5ml of dichloromethane solution at ~5°C, slowly rise to 25°C and react for 2 hours, pour into 50ml of water, separate, separate by silica gel column chromatography, elute with petroleum ether, elute The solution was concentrated to obtain 1.9 g of a yellowish solid, MS (m / e): 416, and the yield was 91.3%.

[0115] (2) Synthesis of compound 3,9-dibromo-1-formyl-7,7-trimethyl-7-hydrogen-benzo[d,e]anthracene shown in formula (M2-b)

[0116] 500ml three-necked flask, add 6.33g 3,9-dibromo-1,7,7-trimethyl-7-hydrogen-benzo[...

Synthetic example 3

[0120] This synthesis example prepares the intermediate shown in formula (M3), and synthetic route is as follows:

[0121]

[0122] The preparation method is the same as M1, except that acetone is replaced by cyclopentanone during the addition reaction after 1-(2-bromophenyl)-2-methylnaphthalene is made into a lithium salt, and 6.1g of the product is obtained, MS (m / s) :372.

[0123] Similarly, different ketones can be selected as raw materials to obtain different R 1 , R 2 Group intermediates, and then obtain different types of compounds of the present invention.

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Abstract

The invention relates to a 2,6,6,8-tetra-substituted-6H-benzo[cd]pyrene compound as shown in the formula (I), wherein R1 and R2 are selected from C6-C50 aryls, substituted C6-C50 aryls and C1-C20 alkyls or form a ring compound through being connected through other groups; A1 and A2 are respectively and independently selected from diarylamino as shown in the general formula (2'), or A2 is hydrogen, and A1 is selected from diarylamino as shown in the general formula (2); and Ar3 and Ar4 are independently selected from benzene rings with 6-50 carbon atoms, substituted benzene rings or other thick aromatic rings such as naphthalene and anthracene. The invention also discloses application of the compound to an organic electroluminescence device and particularly discloses application of the compound as a fluorescent material, a hole-transport material and a hole-injection material in an OLED (organic light emitting diode) device.

Description

technical field [0001] The invention relates to a novel organic compound and its application in the technical fields of organic electroluminescence display and lighting. 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 materials, electron blocking materials, luminescent host materials and luminescent guest (dye), etc. In order to ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/61C07C209/10C09K11/06H01L51/54C09B3/82
Inventor 范洪涛李艳蕊张向慧任雪艳
Owner BEIJING ETERNAL MATERIAL TECH
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