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

A thermally activated delayed fluorescent emission material and its application

A technology of thermal activation delay and fluorescence emission, applied in luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problem of poor luminescence performance of acceptor units

Active Publication Date: 2021-03-16
XI AN JIAOTONG UNIV
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among these materials, the conjugated system of the receptor unit constructed is relatively small, and the luminescence performance of the receptor unit itself is poor, so there are great challenges in realizing high-efficiency red light and near-infrared light.

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
  • A thermally activated delayed fluorescent emission material and its application
  • A thermally activated delayed fluorescent emission material and its application
  • A thermally activated delayed fluorescent emission material and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment (I

[0066] Implementation example (I), the synthesis of I-1 and I-2

[0067]

[0068] The chemical synthesis of intermediate M1 refers to the literature report published by the inventor (J. Mater. Chem. C., 2019, 7, 9690).

[0069] Chemical synthesis of M2:

[0070] In a three-necked flask, add 0.888 g (3 mmol) of intermediate M1, 0.682 g (3.9 mmol, 1.3 eq) of NBS, and then add 25 ml of dichloromethane and 25 ml of DMF, and react at 45 ° C after nitrogen replacement. After the reaction was monitored by TCL, the dichloromethane was distilled off, then methanol was added to disperse, the solid was obtained by filtration, and the solid was recrystallized with dichloromethane to obtain 0.9 g of pure product. M2: 1H-NMR (300MHz CDCl3): δ (ppm) 8.67-8.74 (m, 2H,), 8.10-8.17 (m, 3H), 7.72-7.76 (m, 1H), 7.61-7.67 (m, 4H) ,7.49(s,1H). M2 NMR data such as figure 1 shown.

[0071] Chemical synthesis of I-2:

[0072] In a dry three-necked flask, replace the air with nitrogen, add 0.7...

Embodiment (2

[0075] The synthetic scheme of implementation example (2) compound 1-20

[0076]

[0077] In a dry three-necked flask, add intermediate M3 (0.562g), 3,6-dimethylcarbazole (0.858g), cesium carbonate (1.63g), DMF (30ml), replace the air with nitrogen, and heat to reflux React for 14 hours. After the TCL detection reaction is completed, cool down, add 100ml of water to the reaction system, and filter to obtain a solid. The obtained solid was separated and purified by column chromatography using a mixed solvent of dichloromethane and petroleum ether as an eluent to obtain 0.3 g of I-20 product. M3 NMR data such as Figure 4 shown.

[0078] I-20: 1H-NMR (300MHz CDCl3): δ (ppm) 7.942-7.959 (m, 3H,), 7.875 (s, 2H), 7.568-7.586 (m, 2H), 7.435-7.453 (m, 1H) ,7.358-7.395(m,2H),7.178-7.218(m,3H),7.047-7.066(m,4H),6.885-6.905(m,2H),6.500-6.525(t,1H),2.527-2.534( d, 12H). The NMR data of I-20 is as follows Figure 5 shown.

Embodiment (3

[0079] Implementation example (3), the synthesis of I-33

[0080]

[0081] Synthesis of Intermediate M4

[0082] In a dry three-necked flask, replace the air with nitrogen, add 0.7g of 2,3-dichloroquinoxaline, 1.0g of 4-ethynyltriphenylamine, and 0.123g of Pd(PPh 3 ) 2 Cl 2 , 0.033g CuI, triethylamine 9mmol, acetonitrile 10ml. After nitrogen replacement, react at 60° C. for 8 hours, then add 30 ml of trifluoroacetic acid to the reaction system, and react for 4 hours. After the TCL detection reaction was completed, 100 ml of water was added to the reaction system, and the solid was obtained by filtration. The obtained solid was separated and purified by column chromatography using a mixed solvent of dichloromethane and petroleum ether as an eluent to obtain 1.0 g of M4 product.

[0083] M4: 1H-NMR (300MHz CDCl3): δ (ppm) 8.188-8.208 (d, J = 8Hz, 1H,), 8.115-8.133 (d, J = 7.2Hz, 3H), 7.874-7.896 (d, J = 7.2Hz, 2H), 7.739-7.766(m, 2H), 7.348-7.386(m, 4H), 7.138-7.223(m, ...

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 discloses a thermally activated delayed fluorescent emission material and its application. The acceptor unit is constructed as a multi-component aromatic condensed heterocyclic ring with high luminous efficiency through molecular design. A plurality of N or N, O or N introduced in the fused ring system, S heteroatoms can adjust the electron-deficient weak interaction of the acceptor unit, such as the characteristics and the singlet-triplet energy level difference in the molecular system, which is conducive to the reverse intersystem jump conversion, and can also regulate the intermolecular C-H...π The interaction, hydrogen bonding and local dipole-dipole interaction make the material molecules produce a stacking structure that is conducive to the efficient luminescence of the aggregated state, and realize the high-efficiency luminescence of the aggregated state.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to a heat-activated delayed fluorescent emission material and its application. Background technique [0002] OLED (Organic light-emitting diode), the Chinese name organic light-emitting diode, is the most promising new information display technology and lighting technology after liquid crystal display. After more than 20 years of development, OLED has been applied in the fields of small information display such as mobile phone and camera display, but there are still key obstacles such as service life, device luminous efficiency, and product cost in the field of large-size information display and lighting applications. , failed to be fully commercialized. Material research plays a core and fundamental role in promoting the research process of OLEDs. After more than 20 years of development, OLEDs luminescent materials have experienced three ge...

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 Patents(China)
IPC IPC(8): C07D491/048C07D491/22C09K11/06H01L51/50H01L51/54
CPCC07D491/048C07D491/22C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1062C09K2211/1059H10K85/6576H10K85/6574H10K85/657H10K85/6572H10K50/11
Inventor 王栋东李毅祥汪新叶
Owner XI AN JIAOTONG 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