Platinum (II) tetradentate ONNO complex luminescent material, preparation method and application thereof in organic light emitting diode (OLED)

A technology of luminescent materials and complexes, which can be used in luminescent materials, platinum-based organic compounds, platinum-based organic compounds, etc., and can solve problems such as reducing self-quenching constants

Active Publication Date: 2020-06-23
GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS
View PDF8 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 2010, Che added a tert-butyl group to the red Schiff base ONNO platinum (II) complex (Chem.Asian.J., 2014,9,2984), but the tight intermolecular structure can still be observed in the X-diffraction crystal structure Stacked π-π interactions
In 2014, Che used the same method to introduce a large sterically hindered bicyclic group into the red Schiff base ONNO platinum (II) complex (Chem.Eur.J., 2010,16,233; CN105273712B), which can effectively reduce its self-quenching constant , but the maximum doping concentration in its research is only 7%

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
  • Platinum (II) tetradentate ONNO complex luminescent material, preparation method and application thereof in organic light emitting diode (OLED)
  • Platinum (II) tetradentate ONNO complex luminescent material, preparation method and application thereof in organic light emitting diode (OLED)
  • Platinum (II) tetradentate ONNO complex luminescent material, preparation method and application thereof in organic light emitting diode (OLED)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1-synthetic intermediate 3101

[0037]

[0038] Fill raw material 4101 (0.1mol), tert-butyl nitrite (0.1mol) in the round bottom flask, cuprous bromide (0.12mol), acetonitrile (200ml), the reaction mixture is warming up to 90 ℃ under stirring 4 Hour. After the reaction mixture was cooled to room temperature, water was added, followed by extraction with dichloromethane. After the solvent was removed by evaporation, a solid product was obtained and slurried with methanol at -20°C. Suction filtration and drying yielded a beige solid with a yield of 60%.

Embodiment 2

[0039] Embodiment 2-synthetic intermediate 3201

[0040]

[0041] Put intermediate 3201 (60mmol) and dry tetrahydrofuran (100mL) into a three-neck flask, stir at -78°C for 0.5 hours under a nitrogen atmosphere, then slowly add 1.2 equivalents of n-butyllithium solution (2M) dropwise, and continue stirring while maintaining the temperature After 0.5 hour, N-methoxy-N-methylacetamide (60 mmol) was added dropwise, then the temperature was kept and the mixture was stirred for 1 hour, then slowly raised to room temperature and stirred overnight. Quenched by adding saturated ammonium chloride solution, extracted with ethyl acetate, collected the organic phase solution, the crude product was separated by silica gel column chromatography, and then the solid was recrystallized with n-hexane, suction filtered and dried to obtain a light pink solid with a yield of 55% .

Embodiment 3

[0042] Embodiment 3-synthetic intermediate 3301

[0043]

[0044] Intermediate 3201 (30 mmol) and raw material 4201 (33 mmol) were charged into a round bottom flask, 100 mL of methanol was added and stirred to dissolve, and aqueous potassium hydroxide solution (10 mL, 50 mmol) was slowly added dropwise to the mixture. After the dropwise addition was completed, the reaction mixture was heated to 50° C. under a nitrogen atmosphere and stirred for 10 hours. After the reaction mixture was cooled to room temperature, 4M HCl solution was added to adjust the pH of the mixture to neutral, the filtered solid was dissolved in an organic solvent, and the insoluble matter was removed by filtration. After removing the solvent, the solid product obtained was slurried with methanol at -20°C. Suction filtration and drying gave a yellow solid with a yield of 80%.

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 a platinum (II) tetradentate ONNO complex luminescent material, a preparation method and application thereof in an organic light emitting diode (OLED). The platinum (II) tetradentate dipyridyl diphenol ONNO complex luminescent material with a chemical structure shown in the formula I can be used for manufacturing an organic light emitting diode capable of emitting pure redlight. A phenol group at the left tail end of the luminescent material is connected with benzofuran; therefore, compared with the emission spectrum of a dipyridyl diphenol ONNO-Pt (II) complex without a benzofuran group, the emission spectrum of the luminescent material is subjected to red shift; a B group is introduced to a phenol group ring at the right tail end, thus the aggregation resistanceof the platinum (II) complex is effectively improved, the self-quenching rate constant is relatively low, the dark red light emission color purity and good luminous efficiency can be kept within a certain doping concentration range, and the luminescent material is more suitable for an industrial preparation system.

Description

technical field [0001] The present invention relates to a class of structurally optimized organometallic materials and their applications in organic light emitting diodes (OLEDs) and polymer light emitting diodes (PLEDs). Organometallic materials show better emission quantum efficiency as well as better color purity. Using these materials, high-efficiency monochrome OLEDs can be fabricated by a variety of techniques, including vacuum deposition, spin coating, or printing. Background technique [0002] OLED is an organic light-emitting diode (Organic Light-Emitting Diode) or an organic light-emitting device (Organic Light-Emitting). OLED is an independent light-emitting device without backlight, and has the characteristics of fast response, low driving voltage, high luminous efficiency, high resolution, and wide viewing angle. It has become a new generation of display and lighting technology, especially in mobile phones, computers, TVs, Bendable and foldable electronics hol...

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): C07D405/14C09K11/06H01L51/50H01L51/54
CPCC07D405/14C09K11/06C09K2211/185H10K85/346H10K50/11C07F15/0093H10K2101/10C07F15/0086
Inventor 彭嘉欢李慧杨戴雷蔡丽菲
Owner GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap