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Novel compound having condensed ring, and organic electronic device using same

A compound, fused ring technology, applied in the field of organic electronic devices, can solve the problem of not developing stable and effective organic light-emitting diodes, and achieve the effect of excellent efficiency and performance

Active Publication Date: 2012-10-03
LG CHEM LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, stable and effective organic material layer materials for OLEDs have not yet been developed

Method used

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  • Novel compound having condensed ring, and organic electronic device using same
  • Novel compound having condensed ring, and organic electronic device using same
  • Novel compound having condensed ring, and organic electronic device using same

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0093] : Preparation of raw materials represented by chemical formula a

[0094] Carbazole (carbazole, 1.672g, 10mmol), 1-bromo-2-iodobenzene (1-bromo-2-iodobenzene, 1.5mL, 12mmol), potassium carbonate (K 2 CO 3 , 2.7646 g, 20 mmol), cuprous iodide (CuI, 95 mg, 0.5 mmol) and 25 mL xylene were refluxed under nitrogen atmosphere. After cooling to room temperature, the resultant was extracted with ethyl acetate and washed with anhydrous magnesium sulfate (MgSO 4 ) to remove water and remove solvent under reduced pressure. The compound was passed through a silica gel column using hexane solvent, after which the solvent was removed under reduced pressure and dried in vacuo to give the desired above compound as a white solid (800 mg, 25% yield).

[0095] MS: [M+H]+=323.

preparation Embodiment 2

[0096] : Preparation of raw materials represented by chemical formula b

[0097] After the raw material represented by chemical formula a (6.96g, 21.6mmol) was dissolved in 300ml of purified THF and cooled to -78°C, n-BuLi (2.5Min hexane, 8.64ml, 21.6mmol) was slowly added dropwise thereto. After stirring at this temperature for 30 minutes, 2,7-dibromo-9-fluorenone (2,7-dibromo-9-fluorenone, 6.08 g, 18.0 mmol) was added thereto. After stirring at this temperature for 40 minutes, the temperature was raised to normal temperature and stirring was continued for 3 hours. Ammonium chloride (NH 4 Cl) aqueous solution to complete the reaction, extracted with ether. Anhydrous magnesium sulfate (MgSO 4 ) after removing the water in the organic material layer, the organic solvent is removed. The resulting solid was dispersed in ethanol, filtered and vacuum dried after stirring for a full day to afford 10.12 g (96.7% yield) of intermediate material. After the obtained solid was dispe...

preparation Embodiment 3

[0099] : Preparation of raw materials represented by chemical formula c

[0100] Diphenylamine (1.692g, 10mmol), 1-bromo-2-iodobenzene (1-bromo-2-iodobenzene, 1.5mL, 12mmol), potassium carbonate (K 2 CO 3 , 2.7646 g, 20 mmol), cuprous iodide (CuI, 95 mg, 0.5 mmol) and 25 mL xylene were refluxed under nitrogen atmosphere. After cooling to room temperature, the product was extracted with ethyl acetate and washed with anhydrous magnesium sulfate (MgSO 4 ) to remove water and remove solvent under reduced pressure. The compound was passed through a silica gel column by using hexane solvent, after which the solvent was removed under reduced pressure and dried in vacuo to give the desired compound c above as a white solid (2.27 g, 70% yield).

[0101] MS: [M+H]+=324.

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Abstract

The present invention relates to a novel compound having a condensed ring, and an organic electronic device using the same. Since the compound according to the present invention can be used as an organic layer material of an organic electronic device, and particularly is effective for the injection, transport or extraction of holes, an organic electronic device with excellent efficiency and performance can be provided.

Description

technical field [0001] The present invention relates to a novel compound and an organic electronic device using the same. This application claims priority from Korean Patent Application No. 10-2009-0109940 filed in KIPO on November 13, 2009, the entire disclosure of which is incorporated herein by reference. Background technique [0002] An organic electronic device refers to a device that requires charge exchange between electrodes and organic materials using holes and / or electrons. Organic electronic devices can be mainly divided into the following two types according to their working principles. First of all, there is an electronic device that forms an exciton (exiton) in an organic layer by photons flowing into the device from an external light source, the exciton is separated into electrons and holes, and the electrons and holes are respectively transferred to other electrodes and used as a power source (voltage source). Secondly, there is an electronic device in whi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06H01L51/54
CPCH05B33/22C09K2211/1029H01L51/0061C09K11/06H01L51/0072H01L51/006H01L51/5048H01L51/5088Y02E10/549H10K85/636H10K85/633H10K85/6572H10K50/14H10K50/17
Inventor 金公谦李载澈金芝垠南玄张俊起全炳宣
Owner LG CHEM LTD
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