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

Compound having acridan ring structure and organic electroluminescent element

A technology of dihydroacridine and compounds, applied in the field of organic electroluminescent devices, can solve the problems of insufficient current efficiency, problems of amorphousness, and low driving voltage, etc.

Inactive Publication Date: 2014-12-10
HODOGOYA CHEMICAL CO LTD
View PDF9 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] However, for devices using these compounds in the hole injection layer or hole transport layer, although the heat resistance, luminous efficiency, etc. are improved, it is not enough; Can't say enough, there is also a problem with the non-crystalline

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 having acridan ring structure and organic electroluminescent element
  • Compound having acridan ring structure and organic electroluminescent element
  • Compound having acridan ring structure and organic electroluminescent element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0121]

[0122] Under nitrogen atmosphere, add 7-bromo-10-(9,9-dimethyl-9H-fluoren-2-yl)-2,9,9-trimethyl-9,10-dihydro to the reaction vessel Acridine 5.27g, 9-phenyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolin-2-yl)-9H-carbazole 4.70g, Toluene 79ml, ethanol 20ml, 2M potassium carbonate aqueous solution 8ml, nitrogen gas was passed for 30 minutes while irradiating ultrasonic waves. 0.24 g of tetrakis(triphenylphosphine)palladium was added, heated, and stirred at 67° C. for 5 hours. After naturally cooling to room temperature, 50 ml of toluene was added, and the organic layer was collected by liquid separation. The organic layer was washed with 50 ml of water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (carrier: silica gel, eluent: hexane / toluene). Next, after repeating crystallization in a mixed solvent of toluene and diisopropyl ether and crystallization ...

Embodiment 2

[0126]

[0127] Under nitrogen atmosphere, add 2-bromo-10-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9,10-dihydroacridine to the reaction vessel 7.00g, 4,4,5,5-tetramethyl-2-(triphenylene-2-yl)-[1,3,2]dioxaborane 5.16g, tetrakis(triphenylphosphine)palladium 0.34 g, 4.03 g of potassium carbonate, 40 ml of toluene, 10 ml of ethanol, and 15 ml of water were heated and stirred under reflux for 3 hours. Naturally cooled to room temperature, water and toluene were added, and the organic layer was collected by liquid separation. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (carrier: silica gel, eluent: toluene / hexane=1 / 1) to obtain 10-(9,9-dimethyl-9H-fluoren-2-yl)- 5.40 g of white powder of 9,9-dimethyl-2-(triphenylene-2-yl)-9,10-dihydroacridine (compound 71) (yield 59%).

[0128] For the obtained white powder, structure identification was...

Embodiment 3

[0131] Synthesis of

[0132] Under a nitrogen atmosphere, 11.0 g of 1-bromo-4-(dibenzofuran-2-yl)benzene, 4,4,5,5-tetramethyl-2-(10-phenyl- 2,9,9-trimethyl-9,10-dihydroacridin-7-yl)-[1,3,2]dioxaborane 17.3g, tetrakis(triphenylphosphine)palladium 0.78g, 7.05 g of potassium carbonate, 110 ml of toluene, 18 ml of ethanol, and 25 ml of water were heated and stirred under reflux for 6.5 hours. Naturally cooled to room temperature, water and toluene were added, and the organic layer was collected by liquid separation. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (carrier: silica gel, eluent: toluene / heptane=1 / 4) to obtain 2-[(dibenzofuran-2-yl)benzene-4-yl)- 13.2 g of white powder of 7,9,9-trimethyl-10-phenyl-9,10-acridine (compound 80) (yield 71%).

[0133] For the obtained white powder, structure identification was carried out using NMR. ...

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
glass transition temperatureaaaaaaaaaa
glass transition temperatureaaaaaaaaaa
Login to View More

Abstract

[Problem] To provide an organic compound that, as a material for a high-efficiency, high-durability organic electroluminescent element, has superior hole injection / transport performance, has electron stopping ability, and has the characteristics of high stability in a thin-film state and superior heat resistance, and furthermore to provide a high-efficiency, high-durability organic electroluminescent element using the compound. [Solution] The compound has an acridan ring structure represented by a general formula (compound 1), and the organic electroluminescent element, which has a pair of electrodes and at least one organic layer sandwiched therebetween, is characterized by the compound being used as a constituent material of the at least one organic layer.

Description

technical field [0001] The present invention relates to a compound suitable for an organic electroluminescent device, which is a self-luminous device suitable for various display devices, and to the device, in particular, to a compound having a 9,10-dihydroacridine ring Structured compounds and organic electroluminescent devices using the compounds. Background technique [0002] Organic electroluminescence devices are self-luminous devices, so they are brighter than liquid crystal devices, have excellent visibility, and can perform clear display, so active research has been conducted on them. [0003] In 1987, C.W.Tang et al. of Eastman Kodak Company put organic electroluminescent devices using organic materials into practical use by developing a stacked structure device in which various functions are allocated to each material. They used the phosphor capable of transporting electrons, tris(8-hydroxyquinoline)aluminum (hereinafter referred to as Alq 3 ) and an aromatic ami...

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): C07D219/02C07D401/04C07D401/10C09K11/06H01L51/50H10K99/00
CPCC09K2211/1011H01L51/0072C09K2211/1029C09K2211/1092H01L51/0061H01L51/50C07D405/10C07D409/14C07D401/10C07D219/02C09K2211/1007C07D409/04C09K11/06C07D405/14H01L51/0073C09K2211/1088C07D401/04C07D405/04C07D495/04H10K85/622H10K85/626H10K85/615H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K50/17H10K50/181H10K85/636H10K50/00H10K50/11H10K50/15H10K50/18
Inventor 横山纪昌长冈诚神田大三桦泽直朗林秀一
Owner HODOGOYA CHEMICAL 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