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Tetradentate platinum (II) complex material based on oxazole, thiazole or imidazole and its application

A complex, thiazole technology, applied in the field of phosphorescent doping materials, can solve the problems of poor stability and performance to be improved, and achieve the effects of low efficiency roll-off, low quenching constant, and high fluorescence quantum efficiency

Inactive Publication Date: 2019-07-05
GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, O^N^N^O tetradentate platinum (II) complexes are mainly Schiff bases, which are relatively common, but relatively poor in stability; O^N^C^O and O^ N^C^N tetradentate platinum(II) complexes are relatively stable, but the performance needs to be improved

Method used

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  • Tetradentate platinum (II) complex material based on oxazole, thiazole or imidazole and its application
  • Tetradentate platinum (II) complex material based on oxazole, thiazole or imidazole and its application
  • Tetradentate platinum (II) complex material based on oxazole, thiazole or imidazole and its application

Examples

Experimental program
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Embodiment 1

[0065]

[0066] Synthesis of Compound 1: Dissolve 5.45g (50mmol) of o-aminophenol in 125mL of toluene, add 9.25g (1.0eq., 50mmol) of m-bromobenzaldehyde, stir at room temperature for 1hr, then heat to 110°C for 12hr under reflux. After the reaction stopped, cool to room temperature, remove the solvent by rotary evaporation, then add an appropriate amount of water and ethyl acetate for extraction, collect the organic phase, dry it with anhydrous magnesium sulfate, add an appropriate amount of silica gel, remove the solvent by rotary evaporation, and use n-hexane / ethyl acetate system Through column chromatography, 9.32 g of white solid was obtained, with a yield of 68% and a purity of 99.0%.

[0067] The synthesis of compound 2: get 5.48g (20.0mmol) compound 1, biboronic acid pinacol ester 6.35g (1.25eq., 25.0mmol), potassium carbonate 2.59g (1.25eq., 25.0mmol) and Pd (dppf) Cl 2 292mg (0.02eq., 0.4 mmol), was added to a three-necked flask, vacuumed and replaced with nitroge...

Embodiment 2

[0073]

[0074] Synthesis of Compound 5: Dissolve 5.45g (50mmol) of o-aminothiophene in 125mL of toluene, add 9.25g (1.0eq., 50mmol) of m-bromobenzaldehyde, stir at room temperature for 1hr, then heat to 110°C for 12hr under reflux. After the reaction stopped, cool to room temperature, remove the solvent by rotary evaporation, then add an appropriate amount of water and ethyl acetate for extraction, collect the organic phase, dry it with anhydrous magnesium sulfate, add an appropriate amount of silica gel, remove the solvent by rotary evaporation, and use n-hexane / ethyl acetate system Column chromatography yielded 13.05 g of white solid with a yield of 90% and a purity of 99.0%.

[0075] The synthesis of compound 6: get 5.80g (20.0mmol) compound 5, biboronic acid pinacol ester 6.35g (1.25eq., 25.0mmol), potassium carbonate 2.59g (1.25eq., 25.0mmol) and Pd (dppf) Cl 2 292mg (0.02eq., 0.4 mmol), was added to a three-necked flask, evacuated and replaced with nitrogen several ...

Embodiment 3

[0080]

[0081] Synthesis of compound 9: get 5.41g (50mmol) o-aminophenol and dissolve in 150mL acetonitrile, add 9.25g (1.0eq., 50mmol) m-bromobenzaldehyde, stir at room temperature for 1hr, then add 36% hydrochloric acid 16.5mL and 30 % hydrogen peroxide 41.1mL, stirred at room temperature for 12hr. After the reaction stopped, add saturated sodium carbonate solution to adjust the pH to neutral, then add an appropriate amount of water and ethyl acetate to extract, collect the organic phase, dry it over anhydrous magnesium sulfate, add an appropriate amount of silica gel, and remove the solvent by rotary evaporation. The ester system was subjected to column chromatography to obtain 11.74 g of a white solid with a yield of 86% and a purity of 99.0%.

[0082] Synthesis of Compound 10: Take 5.46g (20.0mmol) of Compound 9, dissolve it in 60mL N,N-dimethylformamide, then add 4.80g (6.0eq., 120.0 mmol), after stirring the reaction for 2hr, 3.29 g (24.0 mmol) of n-bromobutane was...

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Abstract

The present invention relates to a tetradentate platinum (II) complex material based on oxazole, thiazole or imidazole and its application. The complex has the O-N-C-N configuration, the structure isas shown in formula (1), wherein A1-A4 is a substituted or unsubstituted five-membered ring, a six-membered ring and a fused ring structure; X is oxygen, sulfur or substituted nitrogen (-NR0), R0 is one or more R-substituted or unsubstituted C1-C8 alkyl, C5-C20 aryl or heteroaryl, R is halogen, C1-C4 alkyl, diphenylamino, carbazolyl, fluorenyl. The complex can be used as a phosphorescent dopant inthe field of OLED. Organometallic complexes with high fluorescence quantum efficiency, good thermal stability and low quenching constant can be used to fabricate yellow-green OLED devices with high luminescence efficiency and low roll-off.

Description

technical field [0001] The invention relates to a novel tetradentate platinum (II) complex metal-organic material based on oxazole, thiazole and imidazole, which is mainly used in OLED light-emitting devices as a phosphorescent doping material in the light-emitting layer. Background technique [0002] Organic Light-Emitting Diode (OLED), also known as organic electro-laser display and organic light-emitting semiconductor, was discovered in the laboratory in 1979 by Ching W. Tang, a Chinese-American professor. OLED display technology has the advantages of self-illumination, wide viewing angle, almost infinitely high contrast ratio, low power consumption, and extremely high response speed. Especially, OLED has potential flexible and foldable characteristics, so it has been widely concerned and researched, but OLED There are shortcomings such as short service life, poor color purity, and easy aging, which hinder the large-scale application of OLED technology. Therefore, design...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54H10K99/00
CPCC07F15/0086C09K11/06C09K2211/185H10K85/346H10K50/12H10K50/11H10K50/00C07F15/00C09K11/02
Inventor 康健戴雷蔡丽菲
Owner GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS
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