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Photophosphorescence material contain iridium complex of phenylquinoline and acidamide group and preparation thereof

A technology of phenylquinoline and iridium complexes, which is applied in the field of organic electroluminescent materials, can solve the problems of complex synthesis methods, high cost, and difficult industrial production, and achieve strong phosphorescence performance, low cost, and easy synthesis.

Inactive Publication Date: 2008-10-08
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These ligands generally have problems such as complex synthesis methods, high cost and difficulty in industrial production.

Method used

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  • Photophosphorescence material contain iridium complex of phenylquinoline and acidamide group and preparation thereof
  • Photophosphorescence material contain iridium complex of phenylquinoline and acidamide group and preparation thereof
  • Photophosphorescence material contain iridium complex of phenylquinoline and acidamide group and preparation thereof

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preparation example Construction

[0021] The preparation method of the metal iridium complex of the present invention: first obtain an amide by reacting an amine derivative with an acid chloride, and then react with a chlorine bridge dimerization complex (pq) of a 2-phenylquinoline (pq) ligand 2 Ir(μ-Cl) 2 Ir(pq) 2 The ligand exchange reaction is carried out under certain conditions to obtain the target product.

[0022] (1) Synthesis of amides:

[0023]

[0024] When R 1 = Me,R 2 =Ph, the synthetic method of acetanilide is: after aniline and acetic anhydride are refluxed in acetic acid with a molar ratio of 1:2 for 4 hours, the solution obtained by the reaction is poured into ice water, the precipitated solid is suction filtered, and then the obtained The solid can be recrystallized in ethanol to obtain acetanilide.

[0025] When R 1 = Ph, R 2 When =Ph, that is, the synthesis of benzanilide: first take benzoic acid as raw material, add excess SOCl under no solvent 2 The reaction generates benzoyl c...

Embodiment 1

[0032] Example 1: Synthesis of iridium complexes whose ligands are acetanilide and phenylquinoline. Its structural formula is as follows:

[0033]

[0034] (1) Preparation of Acetanilide:

[0035] Add 9.3g (0.1mol) of aniline and 20mL (0.05mol) of acetic acid into a 250mL round bottom flask, then dropwise add 5.1g (0.05mol) of acetic anhydride under stirring, heat to reflux, and stop reflux after 4 hours. The reaction solution was poured into ice water, and a large amount of white solid was precipitated. The white solid obtained was filtered with suction, and the white solid was collected and dissolved in about 90 mL of ethanol for recrystallization. 10.9 g (81.0% yield) of white flaky crystals were obtained, m.p=114°C.

[0036] (2) Chlorine bridge dimeric iridium complex (pq) 2 Ir(μ-Cl) 2 Ir(pq) 2 Synthesis:

[0037] Take 0.352g (0.05mmol) iridium trichloride hydrate, 0.625g (0.12mmol) 2-phenylquinoline in a 100mL three-necked flask, add 15mL2-ethoxyethanol and 5mL w...

Embodiment 2

[0040] Embodiment 2: ligand is the synthesis of the metal iridium complex of benzanilide and phenylquinoline, and its structural formula is as follows:

[0041]

[0042] (1) Preparation of benzanilide

[0043] Add 12.4g (0.1mol) of benzoic acid to a 250mL single-necked flask, add 25mL (1.05mol) of thionyl chloride, heat to reflux, and absorb the generated tail gas with aqueous sodium hydroxide solution. After reacting for 1 hour, the benzoic acid was completely dissolved, and the heating was stopped, and excess thionyl chloride in the reaction solution was taken out until the constant weight of the flask. Then, 20 mL of diethyl ether was added twice and pumped again to constant weight to obtain 24.2 mL of benzoyl chloride. Then use the obtained benzoyl chloride to drop in 9.3g (0.1mol) of aniline, wash the precipitated solid with water after the dropwise addition, and use ethanol recrystallization to obtain benzoyl anilide, and obtain 35.5g of white needle-like crystals (y...

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Abstract

Disclosed is iridium complex electrophosphorescent material which contains phenylquinoline and amide group and the preparation method, which belong to the organic electroluminescent material technical field. The invention discloses a class of electrophosphorescent material which contains the iridium complex composed of phenylquinoline and amide which are two types of bidentate ligands; the preparation method of the iridium complex electrophosphorescent material includes that: firstly, amide is obtained through the reaction of amine derivatives and acyl chloride; and then the amide and chloro-bridge dimerization complex (pq)2Ir(u-Cl)2Ir(pq)2 are processed with ligand exchange reaction under the existence of sodium alkoxide; and then the obtained powder product is processed with vacuum drying; the iridium complex electrophosphorescent material which contains phenylquinoline and amide group is obtained through column chromatography after night. The ligands which contain phenylquinoline and amide structure adopted by the iridium complex electrophosphorescent material has the advantages of easy synthesis, low cost, high production rate and easy modification; the synthesized iridium complex has strong phosphorescent emission performance in the solution with room temperature; the electrophosphorescent material in the invention can be used as the functional materials in the organic electroluminescent devices.

Description

technical field [0001] The invention relates to an iridium complex electroluminescent material containing phenylquinoline and amide groups and its preparation, belonging to the technical field of organic electroluminescent materials. The invention mainly relates to an organometallic complex luminescent material formed of iridium, amide and phenylquinoline and its preparation. Background technique [0002] Organic light-emitting diodes (OLEDs) and the flat-panel displays constructed by them are generally considered to have high luminous brightness and luminous efficiency, low driving voltage, fast response speed, wide operating temperature range, convenient molding and processing, and are convenient for large-scale and large-area production, etc. With many advantages, it has become a new type of material with great development potential and market development value. People such as Tang of Kodak company invented the metal-organic complex 8-hydroxyquinoline aluminum (Alq 3 ),...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06H05B33/14
Inventor 丁玉强董晓庆李程于欢符浩
Owner JIANGNAN UNIV
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