Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Organometallic iridium complex and simple synthesis method and uses thereof

An iridium complex, organometallic technology, applied in indium organic compounds, platinum group organic compounds, organic chemistry, etc., can solve the problems of undisclosed coordination compound synthesis, undisclosed organometallic iridium complex synthesis methods, etc., Achieve the effect of improving synthesis yield, high quantum efficiency, and inhibiting the degree of attenuation

Inactive Publication Date: 2018-08-14
JEN CATHOLIC UNIV
View PDF9 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the aforementioned patent documents are synthetic methods specially designed for the field of liquid crystals. According to the simple synthesis method disclosed in the aforementioned patent documents, the substituents connected to the pyridine liquid crystal compound are limited to linear alkyl or alkoxy groups; It discloses that the method is used for the synthesis of organometallic coordination compounds, and does not disclose the synthesis method of organometallic iridium complexes suitable for organic light-emitting devices

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
  • Organometallic iridium complex and simple synthesis method and uses thereof
  • Organometallic iridium complex and simple synthesis method and uses thereof
  • Organometallic iridium complex and simple synthesis method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] First, in step (a1), 10 millimoles (mmol) of 4-tert-butylphenylbromide (4-tert-butylphenylbromide) is dissolved in 20 milliliters of THF to form a solution, and the solution is formed under nitrogen atmosphere (N 2 ), freshly dried magnesium particles (11 mmol) were added to the aforementioned solution, and after half an hour of reaction, the Grignard reagent (Grignard reagent) of 4-tert-butylphenylmagnesium bromide was obtained.

[0053] In step (a2), 10 mmol of phenyl chloroformate (phenyl chloroformate) and 10 mmol of 4-tert-butylpyridine (4-tert-butylpyridine) were reacted in 20 ml of anhydrous THF at -20°C for half an hour , to form nitrogen-containing heteroaromatic ring salts of 4-tert-butylpyridinium chloride.

[0054] In step (a3), the Grignard reagent of 4-tert-butylphenylmagnesium bromide is slowly added into 20 ml of THF solution containing the nitrogen-containing heteroaromatic ring salts by syringe injection, and slowly heated The reaction solution was st...

Embodiment 2

[0068] Coordination compound 2 is synthesized from steps (a1) to (a3) ​​and step (b) similar to the synthesis of coordination compound 1, the difference is that 6-tert-butylquinoline in step (a2) replaces 4-tert Butylpyridine; in step (b) use a mixture of n-hexane and ethyl acetate (volume ratio of 16:1) to purify the crude product, its yield is 65%, and the mixed solution of dichloromethane and hexane After purification by recrystallization, white crystals were obtained, namely coordination compound 2.

[0069] The chemical structure identification of the coordination compound 2 is carried out with a nuclear magnetic resonance spectrometer, and its characteristic peaks are as follows: 1 H-NMR (CDCl 3 ): δ8.17 (d, 1H, J = 8.7Hz, quinoline characteristic peak), 8.13 (d, 1H, J = 9.0Hz, quinoline characteristic peak), 8.10 (d, 2H, J = 8.4Hz, benzene ring characteristic peak), 7.84(d,1H,J=8.7Hz, quinoline characteristic peak), 7.83(dd,1H,J 1 =9.0Hz,J 2 =2.1Hz, characteristic p...

Embodiment 3

[0075] Coordination compound 3 is synthesized similarly to step (a1) to step (a3) ​​and step (b) of the synthesis of coordination compound 1, the difference is that the starting material of step (a1) is 4-bromo-4'- (tert-butyl)-1,1'-biphenyl substituted 4-tert-butylbromobenzene; in step (b) the crude The product, the yield of which was 70%, was purified by recrystallization from a mixed solution of dichloromethane and methanol to obtain white crystals, namely coordination compound 3.

[0076] The chemical structure identification of the coordination compound 3 is carried out with a nuclear magnetic resonance spectrometer, and its characteristic peaks are as follows: 1 H-NMR (CDCl 3 ): δ8.62 (d, 1H, J = 5.1Hz, characteristic peak of pyridine), 8.06 (d, 2H, J = 8.4Hz, characteristic peak of benzene ring), 7.76 (d, 1H, J = 1.2Hz, characteristic peak of pyridine peak), 7.72(d,2H, J=8.4Hz, characteristic peak of benzene ring), 7.63(d,2H, J=8.7Hz, characteristic peak of benzene ri...

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 provides an organometallic iridium complex and a simple synthesis method and uses thereof, the method comprising: step (a): subjecting a t-Bu-Ar1-MgX and a nitrogen-containing heterocyclic aromatic salt to a nucleophilic reaction to obtain an intermediate product, wherein Ar1 is an arylene group having 5 to 16 carbon atoms or a sulfur-containing heteroarylene group having 4 to 14 carbon atoms; X is a halogen atom; the nitrogen-containing heterocyclic aromatic salt is a salt that contains a t-Bu-Ar2 group, and Ar2 is a nitrogen-containing heteroarylene group having 5 to 14 carbonatoms; t-Bu is a tertiary butyl group; step (b): subjecting the intermediate product and an oxidizing agent to an aromatic cyclization reaction to obtain a coordination compound; and step (c): reacting the coordination compound with iridium acetylacetonate to obtain an organometallic iridium complex. The organometallic iridium complex has a structure represented as formula (I).

Description

technical field [0001] The present invention relates to a novel compound, especially an organometallic iridium complex, a simple method for synthesizing the organometallic iridium complex, and an organic light-emitting device comprising the organometallic iridium complex. Background technique [0002] Organic light-emitting diodes (organic light-emitting diodes, OLEDs) have become the focus of display development because of their advantages such as self-luminescence, wide viewing angle, high contrast ratio, and high response rate. The improvement and development of organometallic compounds as luminescent materials is a key factor in the application and development of OLEDs. Among them, the luminous efficiency of organometallic iridium complexes has been proven to be of great help to the application of OLEDs. [0003] The selection of the coordination compound (ligand) in the organometallic iridium complex will not only affect the energy gap of the organometallic iridium com...

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): C07F15/00C09K11/06H01L51/54
CPCC07F15/0033C09K11/06C09K2211/185C09K2211/1029H10K85/342H10K50/11H10K2101/10H10K50/00
Inventor 贾文隆陈永祈
Owner JEN CATHOLIC UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com