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Cyclometalated iridium complex organic electrophosphorescent material, its preparation method and application

A technology of iridium complexes and phosphorescent materials, applied in luminescent materials, organic chemistry, chemical instruments and methods, etc., to achieve the effect of simple synthesis method and high quantum efficiency

Inactive Publication Date: 2012-06-27
SUZHOU INST OF NANO TECH & NANO BIONICS CHINESE ACEDEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the design and synthesis of cyclometalated iridium(III) phosphorescent complexes, the selection and optimization of ligand structures play a crucial role in the luminescent properties of the complexes, although many phosphorescent complexes of cyclometalated iridium have been designed Synthesized, but it is far from meeting the requirements of industrialization, so the development of a simple synthesis method, low cost, high yield, high performance (mainly including good color purity and high quantum yield) ring metal iridium (III) organic electrophosphorescence Materials are still very, very important

Method used

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  • Cyclometalated iridium complex organic electrophosphorescent material, its preparation method and application
  • Cyclometalated iridium complex organic electrophosphorescent material, its preparation method and application
  • Cyclometalated iridium complex organic electrophosphorescent material, its preparation method and application

Examples

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Effect test

Embodiment 1

[0027] Example 1 Weigh 428 mg [Ir(ppy) 2 Cl] 2 , 310 mg of avobenzone and 211 mg of anhydrous sodium carbonate were added to 50 mL of ethylene glycol monoethyl ether, under nitrogen protection, refluxed for 24 hours, then allowed to stand at room temperature, the solvent was spin-dried, and dichloro Methane:petroleum ether=2:1, separated and purified by column chromatography to obtain 500 mg of the target product. Yield: 77%. The product is characterized by NMR, and the results are as follows: 1 H NMR in CDCl 3 , 8.59 (dd, J=6,10 Hz, 2 H), 7.79 (m, 6 H), 7.63 (m, 2 H), 7.57 (m, 2 H), 7.31 (d, J=7.6 Hz, 2 H), 7.00(m, 2H), 6.84(m, 2H), 6.78(m, 2H), 6.72(m, 2H), 6.53(s, 1H), 6.36(t, J=7.6 Hz, 2H), 3.78(s, 3H), 1.27(s, 9H). MS (EI): m / z 810 (M + ). The spectral properties of the product are as follows figure 1 shown.

Embodiment 2

[0028] Example 2 Weigh 648 mg [Ir(bt) 2 Cl] 2 , 341 mg of avobenzone and 230 mg of anhydrous sodium carbonate were added to 50 mL of ethylene glycol nitrogen ethyl ether, under nitrogen protection, refluxed for 24 hours, allowed to stand at room temperature, the solvent was spin-dried, and dichloromethane : Petroleum ether=2:1 to carry out column chromatography separation and purification to obtain 800 mg target product. Yield: 87%. The product is characterized by NMR, and the results are as follows: 1 H NMR in CDCl 3 , 8.10(m, 2H), 7.90(m, 2H), 7.80(m, 6H), 7.31(m, 4H), 7.19(m, 2H), 6.90(m, 2H), 6.79( m, 2H), 6.68 (m, 2H), 6.52 (m, 2H), 6.41(s, 1H), 3.79(s, 3H), 1.28 (s, 9H). MS (EI): m / z 922 (M + ). The spectral property test result of this product is as follows figure 2 shown.

Embodiment 3

[0029] Example 3 Weigh 648 mg [Ir(btp) 2 Cl] 2, 341 mg of avobenzone and 230 mg of anhydrous sodium carbonate were added to 50 mL of ethylene glycol nitrogen ethyl ether, under nitrogen protection, refluxed for 24 hours, allowed to stand at room temperature, the solvent was spin-dried, and dichloromethane : Petroleum ether=2:1 to carry out column chromatography separation and purification to obtain 780 mg target product. Yield: 84%. MS (EI): m / z 922 (M + )

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Abstract

The invention discloses a cyclometalated iridium complex organic electrophosphorescent material, its preparation method and application. The cyclometalated iridium complex organic electrophosphorescent material has the following structural formula, wherein, LCN is C, N ligands that form cyclometalated coordination compounds with metal iridium, and is at least any one of 2-phenylpyridine (ppy) and its derivatives, 2-phenyl benzothiazole (bt) and its derivatives, 2-benzothiophene pyridine (btp) and its derivatives, 2-phenylquinoline (pq) and its derivatives, 2-phenylisoquinoline (piq) and its derivatives, 5-methyl-1-phenylisoquinoline (mpiq) and its derivatives, and 2-(3, 5-dimethyl phenyl) quinoline (dmq) and its derivatives. Synthesized with Avobenzone as an auxiliary ligand, the cyclometalated iridium complex organic electrophosphorescent material has high quantum efficiency, and can be applied in organic light-emitting devices (OLED) as a phosphorescence doped material, and has the advantages of simple preparation method and high yield.

Description

technical field [0001] The invention relates to an organic electroluminescent material, in particular to a class of organic electroluminescent materials of cyclometal iridium complexes with avobenzone as an auxiliary ligand, and a preparation process and application thereof. Background technique [0002] Organic electroluminescent devices (OLEDs) have the advantages of fast response speed, low driving voltage, good color saturation, wide viewing angle, and can be fabricated on flexible substrates, so they have become a research hotspot in the field of flat panel display. [0003] According to the different light-emitting properties of the light-emitting layer materials, organic electroluminescent devices can be divided into fluorescent doped devices and phosphorescent doped devices. According to the prohibition effect of quantum statistics, the theoretical maximum internal quantum efficiency of fluorescent small molecule doped devices is only 25%, while phosphorescent doped ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
Inventor 周宇扬李宛飞刘扬周明
Owner SUZHOU INST OF NANO TECH & NANO BIONICS CHINESE ACEDEMY OF SCI
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