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Iridium complex compound, organic electroluminescence element, and use therefor

A technology of iridium complexes and compositions, applied in electroluminescence light sources, electrical components, electric light sources, etc., can solve the problems of low luminous efficiency and low luminous quantum yield, and achieve high luminous quantum yield and high efficiency Effect

Inactive Publication Date: 2012-08-22
SAMSUNG ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these pigments have the following problems: low luminous quantum yield, and low luminous efficiency of organic EL elements manufactured using these pigments

Method used

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  • Iridium complex compound, organic electroluminescence element, and use therefor
  • Iridium complex compound, organic electroluminescence element, and use therefor
  • Iridium complex compound, organic electroluminescence element, and use therefor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0158] (Synthesis of iridium complex (1-a))

[0159] 【Chemical 16】

[0160]

[0161] Description will be made with reference to the above flowchart.

[0162]

[0163] In a 50ml two-necked flask with a Dimrot condenser and a three-way cock, 1.97g of 2-aminobenzophenone and 1.38g of 4-fluoroacetophenone were dissolved in a mixed solvent of 20ml of acetic acid and 1ml of sulfuric acid, Stir at reflux for 4 hours. Then, 20 ml of ethyl acetate was added and allowed to stand overnight to crystallize quinoline sulfate crystals, so it was filtered and washed with ethyl acetate. The filter residue was added to 50ml of methanol and basically dissolved. 10 ml of 1N-NaOH and 10 ml of water were added thereto. White crystals precipitated, so they were filtered and washed with water to obtain compound (a). The yield (yield) was 1.22 g (41%).

[0164]

[0165] In a 50ml two-necked flask with a Dimrot condenser and a three-way cock, add 2-(4'-fluorophenyl)-4-tert-butyl synthesize...

Embodiment 2

[0169] (Synthesis of iridium complex (1-b))

[0170] Replace 2-aminobenzophenone with 2-amino-4,5-difluorobenzophenone, replace 4-fluoroacetophenone with 4-acetophenone, and use the iridium complex (1-a ) is synthesized in the same way to obtain iridium complex (1-b).

Embodiment 3

[0172] (Synthesis of iridium complex (1-c))

[0173]

[0174] 【Chemical 17】

[0175]

[0176] Dissolve 1.64g of 1-chloroisoquinoline, 1.68g of 4-fluorophenylboronic acid, 2.8g of potassium carbonate, and 0.3g of tetrakis(triphenylphosphine)palladium(0) in 1,2-dimethoxyethane In a mixed solvent of 20 ml and 10 ml of water, the mixture was stirred and refluxed for 3 hours under a nitrogen atmosphere to react. After the reaction, cool to room temperature, add 20 ml of toluene, and remove the water layer. Compound (c) was obtained by purification using silica gel column chromatography. Yield 2.14g.

[0177]

[0178] Compound (a) was replaced with compound (c), and synthesized by the same method as iridium complex (1-a), to obtain iridium complex (1-c).

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Abstract

Provided is a red phosphorescent light-emitting compound, with a high emission quantum yield, used in the manufacture of organic EL elements. Said red phosphorescent light-emitting compound is an iridium complex compound represented by formula (1), in which L1 is either formula (2) or (3).

Description

technical field [0001] The invention relates to an iridium complex, an organic electroluminescent element and uses thereof. Background technique [0002] Since phosphorescent compounds have high luminous efficiency, they have been actively researched and developed in recent years as light-emitting materials in organic electroluminescent devices (in this specification, also referred to as organic EL devices). [0003] The organic EL element using the phosphorescent compound is expected to be widely used in various applications, and it is disclosed in Japanese Patent Application Publication No. 2003-526876 (Patent Document 1) that by using an organic iridium complex as the phosphorescent compound, a large To improve the luminous efficiency of organic EL elements. As the iridium complex, tris(2-(2-pyridyl)phenyl)iridium and its derivatives are illustrated, and it is described that by changing the substituent of the ligand of the aromatic structure to an alkyl or aryl group, th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/50H10K99/00
CPCC07F15/0033C09K11/06C09K2211/1007C09K2211/1029C09K2211/185H05B33/14H10K85/342H10K50/11H10K2101/10
Inventor 寺岛崇田口勇田嶋胜高桥良明
Owner SAMSUNG ELECTRONICS CO LTD
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