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New diamine derivatives, preparation method thereof and organic electronic device using the same

A technology of diamine derivatives and compounds, applied in the field of new diamine derivatives, their preparation and organic electronic devices using the diamine derivatives, can solve the problems of organic material layer materials for organic light-emitting devices that have not been fully realized, To achieve the effect of excellent life and stability

Active Publication Date: 2009-04-08
LG CHEM LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the development of stable and efficient organic material layer materials for organic light-emitting devices has not been fully realized

Method used

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  • New diamine derivatives, preparation method thereof and organic electronic device using the same
  • New diamine derivatives, preparation method thereof and organic electronic device using the same
  • New diamine derivatives, preparation method thereof and organic electronic device using the same

Examples

Experimental program
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Effect test

Embodiment

[0171] Hereinafter, preferred embodiments of the present invention will be described for further understanding of the present invention. However, the following examples are presented for illustrative purposes only, and thus do not limit the scope of the present invention.

[0172] Compounds of general formula 1 according to the invention can be prepared in multistep chemical reactions. The preparation of this compound is described in the Examples below. It is clearly shown in the examples that a certain intermediate compound is prepared first, and then the compound of general formula 1 is prepared using the intermediate compound. Representative intermediate compounds are listed as compounds A to M below. In these compounds, "Br" may be substituted by any other active atom or functional group.

[0173]

[0174] [Compound A] [Compound B] [Compound C]

[0175]

[0176] [Compound D] [Compound E] [Compound F]

[0177]

[0178] [Compound G] [Compound H] [Compo...

preparation Embodiment 1

[0181] Preparation Example 1 : Preparation of Compound A

[0182] Dibromobenzene (20 g, 84.78 mmol) was dissolved in anhydrous tetrahydrofuran (THF, 200 mL) under nitrogen atmosphere at room temperature. The solution was cooled to -78°C. n-BuLi (34 mL, 2.5M in pentane) was slowly added to the solution at -78°C, and the temperature of the mixture was slowly raised to 0°C over about 1 hour. To the mixture was added trimethylgermanium bromide (18 ml, 101.74 mmol), and the temperature of the mixture was raised to room temperature over 1 hour. After confirming that the reaction was complete, the mixture was extracted from ethyl acetate, dried over magnesium sulfate, and distilled under reduced pressure to obtain Compound A (20 g, 90%). MS(M+)273

preparation Embodiment 2

[0183] Preparation Example 2 : Preparation of Compound B

[0184] Under nitrogen atmosphere, compound A (18g, 65.45mmol), aniline (6.6ml, 72mmol), pd(dba) 2 (0.125g, 0.13mmol), P(t-Bu) 3 (0.04 g, 0.2 mmol) and sodium tert-butoxide (1.80 g, 18.7 mmol) were added to toluene (200 mL), and the mixture was refluxed for about 3 hours. After the reaction was complete, the mixture was cooled to room temperature, and the reaction mixture was added to THF and H 2 in a mixed solution of O. The organic layer was separated, dried over magnesium sulfate and then concentrated. The residue was separated by column chromatography to obtain compound B (16 g, 85%). MS[M]=286

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Abstract

The present invention relates to a novel diamine derivative, a method for preparation thereof, and an organic electronic device using the same. The diamine derivative according to the present invention can serve as a hole injecting, hole transporting, electron injecting, electron transporting, or light emitting material in an organic electronic device including an organic light emitting device. Particularly, it can be used as a light emitting material as used alone, and also serve as a light emitting host, or a light emitting dopant, in particular, a blue light emitting dopant. The organic electronic device according to the present invention exhibits excellent characteristics in terms of efficiency, drive voltage, life time, and stability.

Description

technical field [0001] The present invention relates to a novel diamine derivative, a preparation method thereof and an organic electronic device using the diamine derivative. [0002] This application claims priority from Korean Patent Application No. 10-2006-0026468 filed on March 23, 2006, the entire contents of which are incorporated herein by reference in their entirety. Background technique [0003] Organic electronic devices refer to devices that require charge exchange between electrodes and organic materials using holes and electrons. According to their operating principles, organic electronic devices are mainly divided into the following two categories: An electronic device is constructed by allowing photons to flow into the device from an external light source, thereby forming excitons in organic material layers, whereupon the excitons are divided into electrons and space The formed electrons and holes are respectively transported to different electrodes and act ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/54
CPCC07C211/61C07C211/54Y10S428/917C07F7/0818C07F7/30C07F7/081C07C211/57C07C211/50C09K11/06
Inventor 张惠荣李载澈朴振均金公谦金芝垠朴胎润洪性佶全相映郑栋燮
Owner LG CHEM LTD
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