Compounded quindoline derivative and application of compounded quindoline derivative in organic electroluminescence field

A technology of quinolines and derivatives, which is applied in the application field of organic electroluminescent devices, can solve the problems of reducing device life, easy crystallization or agglomeration, and reducing device efficiency, and achieves reduced quenching and high triplet state , the effect of wide energy gap

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

AI Technical Summary

Problems solved by technology

Materials with low Tg temperature have poor thermal stability and are easy to crystallize or agglomerate, which will greatly reduce the life of the device and seriously reduce the efficiency of the device

Method used

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  • Compounded quindoline derivative and application of compounded quindoline derivative in organic electroluminescence field
  • Compounded quindoline derivative and application of compounded quindoline derivative in organic electroluminescence field
  • Compounded quindoline derivative and application of compounded quindoline derivative in organic electroluminescence field

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] This embodiment is to prepare intermediate formula S1:

[0035] Reference (Angew.Chem.Int.Ed.Engl., 1987,26,460.) method to synthesize the 4,9-dichloroquinoline intermediate of S1.

[0036]

[0037] Its synthetic route is as follows:

[0038]

Embodiment 2

[0041] The synthesis of compound M1, the synthetic route is as follows:

[0042]

[0043] Under the protection of Ar gas, add 4.04g of diphenylamine (molecular weight 169, 0.024mol) and 40ml of anhydrous THF into a 100ml reaction flask, cool to 0°C, and slowly add 11ml of n-BuLi (2.4M, 0.026mol). Stirred at room temperature for 30min, the color turned yellow. At 0°C, take the solution for 30 minutes, slowly add S13.0g (molecular weight 299.15, 0.01mol) into 50ml THF solution, stir at 35°C for 4 hours, stir at 50°C for 8 hours, cool, and the mixture is poured into water Li, extracted with 50ml of dichloromethane, the organic phase was dried with anhydrous MgSO4, the organic phase was evaporated to dryness, and the obtained solid was separated by column chromatography to obtain 4.0 g of a yellow solid with a molecular weight of 565 and a yield of 70%.

[0044]Product MS (m / e): 565, elemental analysis (C 40 h 28 N 4 ): theoretical value C: 85.08%, H: 5.00%, N: 9.92%; measu...

Embodiment 3

[0046] The synthesis of compound M2, the synthetic route is as follows:

[0047]

[0048] Under the protection of Ar gas, add 5.11g NaH (content 55%, 0.117mol) in 90ml DMF, dropwise add a solution of carbazole 16.7g (molecular weight 167, 0.1mol) dissolved in anhydrous DMF90ml, take 20 minutes, stir for 1 hour , then dissolve S113.46g (molecular weight 299.15, 0.045mol) (molecular weight 299.15, 0.045mol) in 90ml of DMF solution, add it in 20min, stir for 3 hours, pour into 500ml of water, filter the precipitate, vacuum dry, the product with silica gel After column purification, 20.2 g of the target molecule (0.036 mol) was obtained with a molecular weight of 561 and a yield of 75%.

[0049] Product MS (m / e): 561, elemental analysis (C 40 h 24 N 4 ): theoretical value C: 85.69%, H: 4.31%, N: 9.99%; measured value C: 85.60%, H: 4.34%, N: 10.05%.

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Abstract

The invention relates to a compounded quindoline derivative as shown in the formula (1), wherein Ar1 and Ar2 are respectively independently selected from C6-C40 substituted or unsubstituted aromatic groups, or can be connected to form C3-C40 substituted or unsubstituted fused aromatic groups. The invention also relates to an application of the compound in organic electroluminescence devices, especially to an application of the compound used as a luminescence host material of OLED devices.

Description

technical field [0001] The invention relates to an organic compound, in particular to a new class of quinoline-containing derivatives and its application in organic electroluminescent devices. Background technique [0002] In 1998, Professor Ma Yuguang of Jilin University prepared an electrophosphorescent device by doping poly-N-vinylcarbazole (PVK) with an osmium complex [Os(CN)2(PPh3)2bpy] (Synthetic Metals, 1998, 94: 245-248). In the same year, Thomson and Forrest cooperated to dope the phosphorescent material platinum octaethylporphyrin (PtOEP) in 8-hydroxyquinoline aluminum (Alq3) as the light-emitting layer of the electroluminescent device, so that the internal quantum efficiency and external quantum efficiency were improved respectively. to 23%, 4% (Nature, 1998, 395: 151-154; Appl. Phys. Lett., 1999, 75: 4-6). Since then, organic light-emitting devices based on phosphorescent metal complexes have developed rapidly. Different from traditional small organic molecule...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C09K11/06H01L51/54
CPCC09K11/06C07D471/04C09K2211/1029H10K85/6572
Inventor 汤金明范洪涛李艳蕊
Owner GUAN ETERNAL MATERIAL TECH
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