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
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  • 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

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  • 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. ...

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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

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D219/02C07D401/04C07D401/10C09K11/06H01L51/50
CPCC09K2211/1011H01L51/0072C09K2211/1029C09K2211/1092H01L51/0061H01L51/50C07D405/10C07D409/14C07D401/10C07D219/02C09K2211/1007C07D409/04C09K11/06C07D405/14H01L51/0073C09K2211/1088C07D401/04C07D405/04C07D495/04H10K85/622H10K85/626H10K85/615H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K85/636H10K50/00H10K50/11H10K50/15H10K50/17H10K50/18
Inventor 横山纪昌长冈诚神田大三桦泽直朗林秀一
Owner HODOGOYA CHEMICAL CO LTD
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