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Material for organic light-emitting device, and organic light-emitting device using same

a technology of light-emitting devices and materials, which is applied in thermoelectric devices, organic chemistry, triarylamine dyes, etc., can solve the problems of difficult preparation of organic light-emitting devices having high efficiency and a long service life, and requiring high electric currents, so as to improve the service life characteristic of the device, reduce the driving voltage of the device, and improve the effect of light efficiency

Inactive Publication Date: 2014-08-21
LG CHEM LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This compound can be used to make materials for an organic light emitting device. When using this compound, the device's driving voltage is reduced, its light efficiency is improved, and its service life is increased because of the compound's thermal stability.

Problems solved by technology

NPB, which has currently been used as the hole transporting layer material, has a glass transition temperature of 100° C. or lower, and thus it is difficult to apply to an organic light emitting device requiring a high electric current.
A LUMO energy level of PEDOT:PSS, which is currently used as a hole transporting material in an organic light emitting device prepared by a solution coating method, is lower than that of an organic material used as a light emitting layer material, and thus it is difficult to prepare an organic light emitting device having high efficiency and a long service life.

Method used

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  • Material for organic light-emitting device, and organic light-emitting device using same
  • Material for organic light-emitting device, and organic light-emitting device using same
  • Material for organic light-emitting device, and organic light-emitting device using same

Examples

Experimental program
Comparison scheme
Effect test

synthetic example 1

Preparation of Compound Represented by Formula 1-1

[0110]

(1) Preparation of Formula 1A

[0111]2-bromodibenzofuran (30 g, 121 mmol), 4-chlorophenyl boric acid (20.9 g, 134 mmol) and potassium carbonate (K2CO3) (39.4 g, 285 mmol) were dissolved in tetrahydrofuran (THF) (300 ml) and H2O (100 ml) and the solution was heated at 50° C. Tetrakis(triphenylphosphine) palladium (Pd(PPh3)4) (2.8 g, 2.42 mmol) was added thereto and then the mixture was refluxed for 12 hours. The mixture was cooled to normal temperature, and then the water layer was removed. Magnesium sulfate (MgSO4) was put into the organic layer and then the mixture was filtered. The mixture was concentrated, and then was purified by column chromatography to obtain the compound of Formula 1A (25 g, yield 74%).

[0112]MS: [M+H]+=278

(2) Preparation of Formula 1-1

[0113]The compound of Formula 1A (10 g, 36 mmol), bisbiphenyl amine (11.6 g, 36 mmol), NaOtBu (4.2 g, 44.1 mmol) and xylene (100 ml) were mixed, and then the mixture was heat...

synthetic example 2

Preparation of Compound Represented by Formula 1-2

[0115]

(1) Preparation of Formula 1B

[0116]A compound of Formula 1B (30 g, yield 70%) was obtained in the same manner as in the preparation of the compound 1A in Synthetic Example 1, except that a compound 4-chlorobiphenyl boronic acid (32 g, 134 mmol) was used instead of the compound 4-chlorophenyl boronic acid.

[0117]MS: [M+H]+=354

(2) Preparation of Formula 1-2

[0118]The compound of Formula 1B (10 g, 28.2 mmol), bisbiphenyl amine (9.1 g, 28.2 mmol), NaOtBu (3.4 g, 35.1 mmol) and xylene (100 ml) were mixed and then the mixture was heated at 100° C. Bis[(tri-tertiary-butyl)phosphine]palladium (Pd(p-t-Bu3)2) (138 mg, 0.27 mmol) was added thereto, and then the mixture was refluxed for 48 hours. The mixture was cooled to normal temperature, and then was purified by column chromatography. The mixture was dried to obtain the compound of Formula 1-2 (15 g, yield 83%).

[0119]MS: [M+H]+=639

synthetic example 3

Preparation of Compound Represented by Formula 1-3

[0120]

(1) Preparation of Formula 1C

[0121]The compound 1A (30 g, 102 mmol) was introduced into a flask including 1 L of dichloromethane to dissolve the compound 1A, then a solution in which bromine (5.30 ml, 108 mmol) was diluted with 400 ml of dichloromethane was slowly added dropwise to the flask, and the mixture was stirred for 12 hours. After the reaction was completed, the reactant solution contained in the flask was washed with a sodium hydrogen carbonate saturated aqueous solution, then the organic layer was separated from the flask, dried over anhydrous magnesium sulfate and then filtered. The filtrate was concentrated and then recrystallized with dichloromethane and ethanol to obtain a white solid compound (15 g, 39%).

[0122]The compound along with phenyl boronic acid (5.63 g, 46.2 mmol) and potassium carbonate (K2CO3) (19.1 g, 138 mmol) was dissolved in tetrahydrofuran (THF) (400 ml) and water (150 ml) and the solution was he...

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PUM

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Abstract

The present invention provides an organic light emitting device including a compound and an organic material layer composed of one more layers including a first electrode, a second electrode and a light emitting layer disposed between the first electrode and the second electrode, in which one or more layers of the organic material layer include the compound of Formula 1 or a compound in which a heat curable or photo curable functional group is introduced into the above-described compound.

Description

TECHNICAL FIELD[0001]The present invention relates to a novel dibenzofuran-based compound that may significantly improve the service life, efficiency, electrochemical stability and thermal stability of an organic light emitting device, and an organic light emitting device containing the dibenzofuran-based compound in an organic compound layer.[0002]This application claims priority from Korean Patent Application No. 10-2011-0091943, filed on Sep. 9, 2011 at the KIPO, the disclosure of which is incorporated herein by reference in its entirety.BACKGROUND ART[0003]An organic light emission phenomenon is an example of converting electric current into visible rays through an internal process of a specific organic molecule. The principle of the organic light emission phenomenon is based on the following mechanism. When an organic material layer is disposed between an anode and a cathode, electrons and holes are injected from the cathode and the anode, respectively, into the organic materia...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): H01L51/00H01L51/50
CPCH01L51/0052H01L51/0061H01L51/50H01L51/006H01L51/0073H10K85/636H10K85/655H10K85/6576H10K50/11H10K50/17C07D307/91C09B57/00C09B57/008C09K11/06H10K85/6574H10K50/156H10K50/15H10K50/16H10K85/615H10K85/631H10K50/00H10K85/633
Inventor HUH, JUNGOHJANG, JUNGIHONG, SUNG KILPARK, TAE YOONCHUN, MINSEUNGCHO, SEONGMI
Owner LG CHEM LTD
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