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2,6,6,8-tetra-substituted-6H-benzo[cd]pyrene compounds and organic light emitting device containing same

A technology of pyrene compound and organic light-emitting layer, which is applied in the compound field of organic electroluminescent devices to achieve the effects of good electron transport ability, excellent thermal and chemical stability

Active Publication Date: 2015-05-27
GUAN ETERNAL MATERIAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 compounds and organic light emitting device containing same
  • 2,6,6,8-tetra-substituted-6H-benzo[cd]pyrene compounds and organic light emitting device containing same
  • 2,6,6,8-tetra-substituted-6H-benzo[cd]pyrene compounds and organic light emitting device containing same

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preparation example Construction

[0062] Synthesis Examples 1-4 are the preparation methods of the intermediates of the present invention. By using these intermediates and selecting appropriate synthetic raw materials as required, the functional group conversion can be carried out by known methods to obtain the compounds of the present invention with different substituents. Described intermediate is the structure shown in formula (M1)~(M4):

[0063]

Synthetic example 1

[0064] Synthesis Example 1: Synthesis of Intermediate (M1)

[0065]

[0066] The preparation method is:

[0067] (1) Synthesis of 1-(2-bromophenyl)-2-methylnaphthalene

[0068]

[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 complete the addition. Then reflux for 30 minutes, cool down to room temperature, and pour out the supernatant for later use.

[0070] In another 500 ml three-necked flask, under the protection of nitrogen, add 13.8 g of o-dibromobenzene, 20 ml of dry toluene, 0.32 g of 1,3-bisdiphenylphosphinopropane nickel chloride, and add dropwise the prepared 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 s...

Synthetic example 2

[0083] Synthesis Example 2: Synthesis of Intermediate (M2)

[0084]

[0085] (1) Synthesis of 3,9-di-bromo-1,7,7-trimethyl-7-hydrogen-benzo[d,e]anthracene

[0086]

[0087] 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%.

[0088] (2) Synthesis of 3,9-dibromo-1-formyl-7,7-trimethyl-7-hydrogen-benzo[d,e]anthracene

[0089]

[0090] 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...

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Abstract

The invention relates to a kind of 2,6,6,8-tetra-substituted-6H-benzo[cd]pyrene compounds shown by formula (1) in the specification, wherein R1 and R2 are selected from C6-C50 aryl, substituted C6-C50 aryl or C1-C20 alkyl; or R1 and R2 are bonded through other groups to form a cyclic compound, Ar1 and Ar2 are separately selected from C5-C30 electron-deficient nitrogen-containing heterocyclic aromatic hydrocarbon, substituted nitrogen heterocyclic aromatic hydrocarbon or thick nitrogen-containing heterocyclic aromatic hydrocarbon or C6-C30 aromatic hydrocarbon or polycyclic aromatic hydrocarbon with the nitrogen-containing heterocyclic aromatic hydrocarbon substituent. The invention also provides an application of the compounds in an organic light emitting device (OLED) and particularly application of the compounds as an electron transport material and a fluorescent or red phosphorescence host material in the OLED device.

Description

technical field [0001] The invention relates to an organic compound, in particular to a compound used 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 materials, electron blocking materials, luminescent host materials and luminescent guest (dye), etc. In order to prepare light-emitting devi...

Claims

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Application Information

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IPC IPC(8): C07D213/127C07D213/06C07D235/18C07D277/66C07D271/107C07D401/10C07D239/26C07D403/14C07D251/24C07D241/12C07D215/04H01L51/50H01L51/54
CPCC07D213/06C07D213/127C07D215/06C07D235/18C07D239/26C07D241/12C07D251/24C07D271/107C07D277/66C07D401/10C07D403/14C07C2603/97C07C2603/54H10K85/6565H10K85/654H10K85/6572H10K85/657H10K50/11
Inventor 范洪涛张向慧李艳蕊任雪艳
Owner GUAN ETERNAL MATERIAL TECH
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