1,2,4-Triazole acceptor-based thermally activated delayed fluorescence material

A technology of thermally activated delay and fluorescent materials, which is applied in the field of organic photoelectric functional materials, can solve the problems of insufficient electron-absorbing ability of acceptor materials, and the emission spectrum is not in the deep blue region, so as to improve the RISC transition probability, improve luminous efficiency, and increase The effect of steric hindrance effect

Inactive Publication Date: 2017-07-11
TAIYUAN UNIV OF TECH
View PDF4 Cites 7 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The main problem of the TADF materials based on triazole groups reported in the literature is that the emission spectrum is not in the deep blue region, which is mainly due to the insufficient electron-withdrawing ability of the acceptor material.

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
  • 1,2,4-Triazole acceptor-based thermally activated delayed fluorescence material
  • 1,2,4-Triazole acceptor-based thermally activated delayed fluorescence material
  • 1,2,4-Triazole acceptor-based thermally activated delayed fluorescence material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Take 5.21g (50mmol) of 2-cyanopyridine, 2.50g (50mmol) of hydrazine hydrate, and 25mL of ethanol, and add them to a 250mL two-neck round-bottomed flask in turn, and react at a low temperature of 0°C for 8h to produce a viscous light yellow paste, at room temperature The excess ethanol was removed under vacuum, the solid was washed with a small amount of ether, filtered, and dried under vacuum at room temperature for 3 hours to obtain white crystals of (2-pyridine)aminohydrazone.

[0048] Weigh 4.08g (30mmol) of (2-pyridine)aminohydrazone into a 250mL two-neck round bottom flask, and then add Na in turn 2 CO 3 3.15g (30mmol), 7.00g (30mmol) of 4-bromobenzoyl chloride, 30mL of tetrahydrofuran, react at room temperature for 6h, and filter. The filtrate was refluxed in 30ml of ethylene glycol for 30min, dehydrated and closed, filtered, dried in vacuum for 8h, and recrystallized with ethanol to obtain 2-(3-(4-bromophenyl)-1H-1,2,4-tri Azazol-5-yl)pyridine is white needle-like c...

Embodiment 2

[0064] The 2-(1-phenyl-3-(4-bromophenyl)-1H-1,2,4-triazol-5-yl)pyridine (1.88g, 5mmol) prepared in Example 1 and phenoxa The oxazine (1.28g, 7mmol) was added to a 100mL two-necked round bottom flask filled with nitrogen, and then tris(dibenzylideneacetone)dipalladium (270mg, 0.3mmol), tri-tert-butylphosphine tetrafluoroborate (340mg, 0.3mmol), sodium tert-butoxide (960mg, 10mmol) and 50mL toluene, heated to reflux temperature for 24h under nitrogen atmosphere. The reaction solution was cooled to room temperature, 50 mL of water was added, and extraction was performed with 200 mL of dichloromethane. The extract was dried over anhydrous magnesium sulfate and purified by petroleum ether / dichloromethane (2:1) column chromatography to obtain 10-(4-( 1-Phenyl-5-(pyridin-2-yl)-1H-1,2,4-triazol-3-yl)phenyl)-10H-phenoxazine (TAZ-PXZ) white solid, yield 59%.

[0065] The structural formula of the prepared TAZ-PXZ is as follows.

[0066]

[0067] 1 H NMR (600 MHz, CDCl 3 , δ): 8.56-8.51 (m...

Embodiment 3

[0073] Take 2-(1-phenyl-3-(4-bromophenyl)-1H-1,2,4-triazol-5-yl)pyridine (1.88g, 5mmol) prepared in Example 1 and 9, 9-Dimethylacridine (1.67g, 8mmol) was added to a 100mL two-necked round bottom flask filled with nitrogen, then tris(dibenzylideneacetone)dipalladium (270mg, 0.3mmol), tri-tert-butyl tetrafluoroborate Phosphine (340 mg, 0.3 mmol), sodium tert-butoxide (960 mg, 10 mmol) and 50 mL of toluene were heated to reflux temperature for 24 hours under a nitrogen atmosphere. The reaction solution was cooled to room temperature, 50 mL of water was added, and extraction was performed with 200 mL of dichloromethane. The extract was dried over anhydrous magnesium sulfate and purified by petroleum ether / dichloromethane (3:1) column chromatography to obtain 9,9-dimethyl Base-10-(4-(1-phenyl-5-(pyridin-2-yl)-1H-1,2,4-triazol-3-yl)phenyl)-9,10-dihydroacridine Pyridine (TAZ-DMAC) is a white solid with a yield of 61%.

[0074] The structural formula of the prepared TAZ-DMAC is as fol...

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

PropertyMeasurementUnit
thicknessaaaaaaaaaa
current efficiencyaaaaaaaaaa
energy conversion efficiencyaaaaaaaaaa
Login to view more

Abstract

The invention discloses a 1,2,4-riazole acceptor-based thermally activated delayed fluorescence material with the structure represented by general formula (I) and capable of realizing dark blue lights. The material is formed through connecting the para-position of 3-substituted phenyl group of a 1,2,4-triazole derivative used as an acceptor unit with an N-containing donor unit. The thermally activated delayed fluorescence material has small singlet-triplet energy level difference, can meet requirements of the thermally activated delayed fluorescence material, allows a dark blue fluorescence material to be obtained, and improves the luminous efficiency of TADF type OLED devices.

Description

Technical field [0001] The invention belongs to the technical field of organic photoelectric functional materials, and relates to a thermally activated delayed fluorescent material, in particular to a thermally activated delayed fluorescent material that uses triazole as an acceptor and can realize blue light. Background technique [0002] Organic-light emitting devices (OLED: Organic-light emitting devices) have received extensive attention due to their high efficiency and fast response speed. Among them, compared with fluorescent light-emitting materials, phosphorescent light-emitting materials can achieve 100% internal quantum efficiency, and the efficiency of the prepared devices is generally higher. However, phosphorescent materials are generally heavy metal complexes, which greatly increases the manufacturing cost of OLED devices. [0003] The third generation of luminescent materials-Thermally Activated Delayed Fluorescence (TADF: Thermally Activated Delayed Fluorescence), ...

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): C07D417/14C07D413/14C07D401/14C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D401/14C07D413/14C07D417/14C09K2211/1044C09K2211/1037C09K2211/1033C09K2211/1007C09K2211/1029C09K2211/1059H10K85/654H10K85/657H10K85/6572H10K50/00
Inventor 许慧侠王芳王科翔孙鹏李洁苗艳勤王华许并社
Owner TAIYUAN UNIV OF TECH
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