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

Compound taking 10,10-diaryl substituted anthranone as mother nucleus and application of compound

A compound, 10-technology, applied in the application field of light-emitting layer materials in organic light-emitting diodes, can solve the problems of efficiency roll-off, low S1 state radiation transition rate, difficult exciton utilization rate and high fluorescence radiation efficiency, etc., to achieve Reduce efficiency roll-off, good industrialization prospects, improve the effect of high exciton utilization and high fluorescence radiation efficiency

Active Publication Date: 2017-08-18
JIANGSU SUNERA TECH CO LTD
View PDF2 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 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 High T through TADF process 1 →S 1 state exciton conversion rate, but at the same time lead to a low S1 state radiative transition rate, therefore, it is difficult to have both (or simultaneously achieve) high exciton utilization efficiency and high fluorescence radiation efficiency; (2) Even if doped devices have been used to alleviate the T excitation Subconcentration quenching effect, the efficiency of most TADF material devices has a serious 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
  • Compound taking 10,10-diaryl substituted anthranone as mother nucleus and application of compound
  • Compound taking 10,10-diaryl substituted anthranone as mother nucleus and application of compound
  • Compound taking 10,10-diaryl substituted anthranone as mother nucleus and application of compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] The synthesis of embodiment 1 raw material A

[0047]

[0048] In a 1L three-neck flask, add 19.8g phenol (0.21mol), 20.8g anthraquinone (0.10mol), 0.2g mercaptopropionic acid, 400mL dichloroethane, mix and stir, raise the temperature to 60-65°C and add dropwise 3.0g formazan Sulfonic acid, after the dropwise addition is completed, keep the reaction at 60-65°C for 4 hours; after the reaction, wash and separate the liquid with cooling water, and remove the solvent from the organic phase under reduced pressure to obtain the crude product, which is recrystallized with absolute ethanol and obtained by column chromatography White crystal-compound X, HPLC purity 99.5%, yield 46.58%;

[0049]Add 18.9g of compound X (0.05mol) and 100g of pyridine into a 500mL three-necked flask, drop the temperature to 0-5°C and add 33.8g of trifluoromethanesulfonic anhydride (0.12mol), and react at room temperature for 6 hours; liquid, the organic phase was decompressed to remove the solve...

Embodiment 2

[0052] The synthesis of embodiment 2 raw material B

[0053]

[0054] In a 250ml three-necked flask, under the protection of nitrogen, add 6.42g of raw material A (0.01mol), 10.16g of double borate pinacol ester (0.04mol), 4.90g of potassium acetate (0.05mol), 0.30g of pd2(dba)3 , 0.20g tri-tert-butylphosphine, 100ml toluene, reflux reaction for 20 hours; after the reaction, cooling, filtration, filtrate rotary evaporation, column chromatography to obtain raw material B, HPLC purity 99.8%, yield 88.26%;

[0055] High-resolution mass spectrometry ESI source, positive ion mode, molecular formula C38H40B2O5, theoretical value: 598.3062, test value: 598.3066.

[0056] Elemental analysis (C38H40B2O5): theoretical value C: 76.28, H: 6.74, O: 13.37, test value C: 76.26, H: 6.75, O: 13.40.

Embodiment 3

[0057] The synthesis of embodiment 3 compound 1

[0058] synthetic route:

[0059]

[0060] In a 250ml three-necked flask, under nitrogen protection, add 3.21g of raw material A (0.005mol), 2.20g of compound M01 (0.012mol), 1.44g of sodium tert-butoxide (0.015mol), 0.15g of pd2(dba)3, 0.10g Tri-tert-butylphosphine, 100ml of toluene, reflux reaction for 20 hours; after the reaction was completed, cooled, filtered, and the filtrate was rotary evaporated, and column chromatography gave compound 1 with a HPLC purity of 99.9% and a yield of 78.40%;

[0061] High-resolution mass spectrometry ESI source, positive ion mode, molecular formula C50H32N2O3, theoretical value: 708.2413, test value: 708.2411.

[0062] Elemental analysis (C50H32N2O3): theoretical value C: 84.73, H: 4.55, N: 3.95, O: 6.77, test value C: 84.71, H: 4.55, N: 3.98, O: 6.76.

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 compound taking 10,10-diaryl substituted anthranone as a mother nucleus and application of the compound to an organic electroluminescent device. The compound takes 10,10-diaryl substituted anthranone as the mother nucleus, and therefore has the characteristics that the probabilities of crystallization and clustering between molecules are low and the film-forming property is favorable. When the compound serves as a luminescent layer material of an OLED luminescent device, the manufactured OLED device has favorable photoelectric property.

Description

technical field [0001] The invention relates to the field of organic electroluminescence, in particular to a compound with 10,10-diaryl substituted anthrone as the core 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 electrode...

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
IPC IPC(8): C07D265/38C07D279/22C07D219/02C07D209/86C07D209/80C07D519/00C07D241/46C07D221/18C07D265/34C07D241/38C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D209/80C07D209/86C07D219/02C07D221/18C07D241/38C07D241/46C07D265/34C07D265/38C07D279/22C07D519/00C09K2211/1044C09K2211/1033C09K2211/1037C09K2211/1029C09K2211/1088C09K2211/1092H10K85/615H10K85/6572H10K85/657H10K50/00
Inventor 高自良张婷婷石宇张司南
Owner JIANGSU SUNERA TECH 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