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

Boron-containing five-membered heterocyclic compound and application thereof to organic light-emitting device

A technology of five-membered heterocycles and compounds, which is applied in the fields of compounds containing Group 3/13 elements of the periodic table, electrical solid devices, electrical components, etc. State radiation transition rate, efficiency roll-off, etc.

Inactive Publication Date: 2019-04-05
VALIANT CO LTD
View PDF3 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although theoretically TADF materials can achieve 100% exciton utilization, there are actually the following problems: (1) The T1 and S1 states of the designed molecules have strong CT characteristics, and the very small S1-T1 state energy gap, although it can A high T1→S1 state exciton conversion rate is achieved through the TADF process, but at the same time it leads to a low S1 state radiative transition rate. Therefore, it is difficult to achieve both (or simultaneously) high exciton utilization efficiency and high fluorescence radiation efficiency; (2) even Doped devices have been used to alleviate the T-exciton concentration quenching effect, and most devices made of TADF materials have a serious efficiency roll-off at high current densities

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
  • Boron-containing five-membered heterocyclic compound and application thereof to organic light-emitting device
  • Boron-containing five-membered heterocyclic compound and application thereof to organic light-emitting device
  • Boron-containing five-membered heterocyclic compound and application thereof to organic light-emitting device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] The synthesis of embodiment 1 compound 5

[0054] The synthetic steps of compound are as follows:

[0055]

[0056] In a 150ml four-neck flask, add 0.01mol of A1 and 50ml of tetrahydrofuran, protect it with nitrogen, cool to -78 degrees Celsius, and then slowly drop in 0.02mol of n-butyl lithium cyclohexane solution. After the drop is completed, stir for 3 hours. Raise the temperature to -10 degrees Celsius, drop in 0.01mol dimethyl tin dichloride tetrahydrofuran solution, after the dropwise addition, keep the temperature for reaction for 1 hour, then warm up to room temperature, remove the tetrahydrofuran by rotary evaporation, and then rinse twice with ethanol to obtain Pale yellow solid B1, purity 98.2%, yield 90%. HRMS(m / z): [M+H] + , the theoretical value is 417.14, and the measured value is 417.11.

[0057] Add 50ml of toluene and 0.01mol B1 to a 150ml three-necked flask, protect it with nitrogen, cool down to -78 degrees Celsius, and then slowly drop in a t...

Embodiment 2

[0060] The synthesis of embodiment 2 compound 10

[0061] The synthetic steps of compound are as follows:

[0062]

[0063] 150ml four-neck flask, add 0.01mol of A2 and 50ml of tetrahydrofuran, nitrogen protection, cool to -78 degrees Celsius, then slowly drop into 0.02mol of n-butyllithium cyclohexane solution, after the completion of the drop, stir the reaction for 3 hours, Raise the temperature to -10 degrees Celsius, drop in 0.01mol dimethyl tin dichloride tetrahydrofuran solution, after the dropwise addition, keep the temperature for reaction for 1 hour, then warm up to room temperature, remove the tetrahydrofuran by rotary evaporation, and then rinse twice with ethanol to obtain Pale yellow solid B2 with a purity of 98.4% and a yield of 89.5%. HRMS(m / z): [M+H] + , the theoretical value is 467.20, and the measured value is 467.15.

[0064] Add 50ml of toluene and 0.01mol B2 to a 150ml three-necked flask, protect it with nitrogen, cool down to -78 degrees Celsius, th...

Embodiment 3

[0067] The synthesis of embodiment 3 compound 20

[0068] The synthetic steps of compound are as follows:

[0069]

[0070] Add 0.01mol of A3 and 50ml of tetrahydrofuran into a 150ml four-necked flask, protect it with nitrogen, cool to -78 degrees Celsius, then slowly drop in 0.02mol of n-butyl lithium cyclohexane solution, and stir for 3 hours to react. Raise the temperature to -10 degrees Celsius, drop in 0.01mol dimethyl tin dichloride tetrahydrofuran solution, after the dropwise addition, keep the temperature for reaction for 1 hour, then warm up to room temperature, remove the tetrahydrofuran by rotary evaporation, and then rinse twice with ethanol to obtain Pale yellow solid B3 with a purity of 97.6% and a yield of 87.5%. HRMS(m / z): [M+H] + , the theoretical value is 391.06, and the measured value is 391.12.

[0071] Add 50ml of toluene and 0.01mol B3 into a 150ml three-necked flask, protect it with nitrogen, cool down to -78 degrees Celsius, and then slowly drop i...

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
thicknessaaaaaaaaaa
thicknessaaaaaaaaaa
Login to View More

Abstract

The invention discloses a boron-containing five-membered heterocyclic compound and an application thereof to an organic light-emitting device. The compound takes a benzo five-membered ring as a core,boron is positioned at the center five-membered ring, and the compound has the advantages that molecules are not easily crystallized or gathered, and the compound has a good film-forming property. When the compound is used as a luminous layer material of the organic light-emitting device, the current efficiency, the power efficiency and the external quantum efficiency of the device can be greatlyimproved, and the service life of the device is obviously prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a boron-containing five-membered heterocyclic compound and its application as a light-emitting layer material in an organic light-emitting diode. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. [0003] The OLED light-emitting device is like a sandwich structure, including electrode material film layers, and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. As a current device, when a voltage is applied to the electrodes at both ...

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): C07F5/02C09K11/06H01L51/54
CPCC09K11/06C07F5/02C09K2211/1096C09K2211/1088C09K2211/1033C09K2211/1029H10K85/636H10K85/657H10K85/6574H10K85/6572
Inventor 叶中华李崇张兆超张小庆
Owner VALIANT CO LTD
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