Unlock instant, AI-driven research and patent intelligence for your innovation.

Tetradentate metal palladium complex containing 4-aryl-3,5-disubstituted pyrazole, as well as preparation method and application thereof

A complex and double substitution technology is applied in the field of blue phosphorescent tetradentate ring metal palladium complex luminescent materials, which can solve the problems of poor stability of blue light devices, poor mechanical processing performance, and scarcity of blue light emitting materials.

Inactive Publication Date: 2018-08-21
ZHEJIANG UNIV OF TECH +1
View PDF3 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Despite remarkable advances in the research of chemical and electro-optic materials, such as red-green phosphorescent organometallic materials that have been commercialized and applied to OLEDs, lighting devices, and phosphorescent materials in advanced displays, currently available materials still have many shortcomings. , including poor machinability, inefficient emission or absorption, and less than ideal stability
[0004] In addition, good blue light-emitting materials are very rare, and a huge challenge is the poor stability of blue light devices, and the choice of host materials has an important impact on the stability and efficiency of the device

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Tetradentate metal palladium complex containing 4-aryl-3,5-disubstituted pyrazole, as well as preparation method and application thereof
  • Tetradentate metal palladium complex containing 4-aryl-3,5-disubstituted pyrazole, as well as preparation method and application thereof
  • Tetradentate metal palladium complex containing 4-aryl-3,5-disubstituted pyrazole, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0172] Example 1: Compound Pd1 can be synthesized according to the following route:

[0173]

[0174] Synthesis of Intermediate Compound 1: Add 3,5-dimethyl-4-bromopyrazole (5250mg, 30.00mmol, 1.00 equivalent) and cuprous iodide into a dry three-necked flask with reflux condenser and magnetic rotor. (572mg, 3.00mmol, 0.10 equivalents), L-proline (690mg, 6.00mmol, 0.20 equivalents), potassium carbonate (8280mg, 60.00mmol, 2.00 equivalents) Purge nitrogen three times, then add m-iodoanisole (10500mg , 45.00mmol, 1.50 equivalent) and redistilled dimethyl sulfoxide (10mL). The reaction mixture was stirred at 120°C for 2 days, and TLC thin layer chromatography monitored until the reaction of the raw material 4-bromopyrazole was completed. Water (100 mL) was added to quench the reaction, filtered, and the insoluble matter was washed with 50 mL of ethyl acetate. The organic phase in the mother liquor was separated, dried over anhydrous sodium sulfate, filtered, and the solvent was dist...

Embodiment 2

[0184] Example 2: Compound Pd2 can be synthesized according to the following route:

[0185]

[0186] Synthesis of intermediate 3-OMe: Add 4-bromo-1-(3-methoxybenzene)-3,5-dimethyl-1hydro-pyrazole 1() to a dry three-necked flask with a magnetic rotor. 4.50g, 16.01mmol, 1.00 equivalent), 2,4,6-trimethylphenylboronic acid (5.25g, 32.02mmol, 2.00 equivalent), Pd 2 (dba) 3 (0.29g, 0.32mmol, 0.02 equivalents), tripotassium phosphate (10.20g, 48.03mol, 3.00 equivalents), S-Phos (0.53g, 0.60mmol, 0.08 equivalents). Nitrogen was pumped three times, and then toluene (100mL) was added. Subsequently, nitrogen was bubbled for 20 minutes, and the reaction mixture was stirred at 110°C for 3 days. Cool, add water (100 mL), extract with ethyl acetate (50 mL×3), combine the organic phases, dry with anhydrous sodium sulfate, filter, and distill the solvent under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography with eluent (petroleum ether...

Embodiment 3

[0194] Example 3: Compound Pd869 can be synthesized according to the following route:

[0195]

[0196] Synthesis of ligand L869: Add 1-(3-hydroxyphenyl)-3,5-dimethyl-4-(2,6-dimethylphenyl)- to a dry sealed tube with a magnetic rotor. Pyrazole 2-OH (877.1mg, 3.00mmol, 1.0eq), 2-bromo-9-(2-(4-tert-butylpyridyl))carbazole Br-Cab-Py-tBu (1.37g, 3.60mmol , 1.2eq, for synthesis method see: The Journal of Organic Chemistry, 2017, 82, 1024-1033), cuprous iodide (57.1mg, 0.30mmol, 0.1eq), ligand 2-picolinic acid (73.9mg, 0.60mmol, 0.2eq), potassium phosphate (1.34g, 6.30mmol, 2.1eq). Purge the nitrogen three times, then add the solvent dimethyl sulfoxide (8 mL). Then the reaction mixture was stirred at 120°C for 3 days, cooled to room temperature, diluted with a large amount of ethyl acetate, filtered, and washed with ethyl acetate. The obtained filtrate was washed twice with water, the aqueous phase was extracted twice, the organic phases were combined, and dried over anhydrous sodiu...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to the field of blue light phosphorescence tetradentate metal palladium complex luminescent materials, and discloses a blue light phosphorescence tetradentate metal palladium complex based on 4-aryl-3,5-disubstituted pyrazole, as well as a preparation method and the application thereof. The complex can be a delayed fluorescent and / or phosphorescent emitter, and has the characteristics of high thermal decomposition temperature, high luminous intensity, deep blue light emission, narrow emission spectrum and the like, so that the complex has a great application prospect in the field of blue light, especially deep blue light phosphorescent materials.

Description

Technical field [0001] The invention relates to the field of blue phosphorescent tetradentate ring metal palladium complex luminescent materials, in particular to a blue phosphorescent tetradentate ring metal palladium complex based on 4-aryl-3,5-disubstituted pyrazole. Background technique [0002] Compounds capable of absorbing and / or emitting light are ideally suitable for use in a variety of optical and electroluminescent devices, including, for example, light absorbing devices such as solar sensors and photosensitive devices, organic light emitting diodes (OLED), light emitting devices A device, or a device capable of both light absorption and light emission, and as a marker for biological applications. Much research has been devoted to the discovery and optimization of organic and organometallic materials for use in optical and electroluminescent devices. Generally, research in this field aims to achieve many goals, including improvements in absorption and emission efficie...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54H01L51/50H10K99/00
CPCC09K11/06C07F15/006C09K2211/185H10K85/341H10K50/00H10K50/11H10K2101/10C09K2211/1029C09K2211/1044
Inventor 李贵杰佘远斌赵向东陈少海
Owner ZHEJIANG UNIV OF TECH
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com