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Dicarbazole derivative and organic electroluminescent element

A derivative, dicarbazole technology, applied in the field of novel dicarbazole derivatives, can solve the problems of insufficient current efficiency, insufficient current efficiency, low voltage driveability, etc., and achieve high luminous efficiency and power efficiency, and good hole injection. properties, wide bandgap effect

Inactive Publication Date: 2016-03-30
HODOGOYA CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] Devices using these compounds as hole-injection layers or hole-transport layers exhibit improvements in heat resistance and luminous efficiency, however, which are still insufficient
In addition, has low voltage drive and current efficiency is not sufficient, and amorphousness still involves problems

Method used

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  • Dicarbazole derivative and organic electroluminescent element
  • Dicarbazole derivative and organic electroluminescent element
  • Dicarbazole derivative and organic electroluminescent element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0186] Synthesis of 5,7-dihydro-5,7-bis(9,9-dimethylfluoren-2-yl)-furo[2,3-a:5,4-a']dicarbazole

[0187] (Synthesis of compound 4)

[0188]

[0189] In a nitrogen-substituted reaction vessel,

[0190] With N,N,N',N'-tetramethylethylenediamine 10.4g, and

[0191] THF40ml

[0192] It was placed and cooled, and a hexane solution (1.6 mol / L) of n-butyllithium was added dropwise thereto while keeping the temperature of the solution at 0° C. or lower.

[0193] Further, the solution was stirred at 0°C for 30 minutes and at room temperature for another 30 minutes.

[0194] After that, 25 ml of THF and 5.0 g of dioxyfluorene were added thereto, and the mixture was heated and stirred at 60° C. for 2 hours. In the next step, 1,2-diiodoethane was added thereto while cooling to below -60°C, and thereafter, the mixture was stirred overnight at room temperature. After adding water and dichloromethane, the organic layer was extracted by a liquid separation operat...

Embodiment 2

[0217] Synthesis of 5,7-dihydro-5,7-bis{4-(oxyfluoren-4-yl)phenyl}-furo[2,3-a:5,4-a']dicarbazole

[0218] (Synthesis of compound 5)

[0219]

[0220] To the nitrogen-purged reaction vessel, add:

[0221]

[0222] And the mixture was bubbled with nitrogen for 1 hour.

[0223] Afterwards, in the reaction vessel,

[0224] Add three (dibenzylidene acetone) dipalladium (O) 0.6g and

[0225] 0.8 g of a toluene solution containing 50% (w / v) of tri-tert-butylphosphine.

[0226] Then, the mixture was heated and stirred at 95°C for 18 hours. The mixture was cooled to room temperature, water was added thereto, extraction was performed using toluene, and an organic layer was extracted. The organic layer was dehydrated using anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a crude product.

[0227] The crude product was purified by column chromatography (carrier: silica gel, eluent: toluene / n-hexane) to obtain 5,7-dihydro...

Embodiment 3

[0236] Synthesis of 5,7-dihydro-5,7-bis(biphenyl-4-yl)-furo[2,3-a:5,4-a']dicarbazole

[0237] (Synthesis of compound 6)

[0238]

[0239] To the nitrogen-purged reaction vessel, add:

[0240]

[0241] The mixture was bubbled with nitrogen for 1 hour.

[0242] Afterwards, in the reaction vessel,

[0243] Add tris(dibenzylideneacetone) dipalladium (0) 0.8g, and

[0244] 1.0 g of a toluene solution containing 50% (w / v) of tri-tert-butylphosphine.

[0245] Then, the mixture was heated and stirred at 95°C for 29 hours. The mixture was cooled to room temperature, water was added thereto, extraction was performed using toluene, and an organic layer was extracted. The organic layer was dehydrated using anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a crude product.

[0246] The crude product is purified by column chromatography (carrier: silica gel, eluent: toluene / n-hexane) to obtain 5,7-dihydro-5,7-bis(biphenyl-4...

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Abstract

This dicarbazole derivative is represented by general formula (1). In the formula, X represents an oxygen atom or a sulfur atom; each of Ar1 and Ar2 represents an aromatic hydrocarbon group or an aromatic heterocyclic group; and each of R1-R12 represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an alkyl group having 1-6 carbon atoms, a cycloalkyl group having 5-10 carbon atoms, an alkenyl group having 2-6 carbon atoms, an alkyloxy group having 1-6 carbon atoms, a cycloalkyloxy group having 5-10 carbon atoms, an aromatic hydrocarbon group, an aromatic heterocyclic group, an aryloxy group, or a disubstituted amino group that has an aromatic hydrocarbon group or an aromatic heterocyclic group as a substituent bonded to a nitrogen atom.

Description

technical field [0001] The present invention relates to a novel dicarbazole derivative, more particularly, a novel dicarbazole derivative suitable for use in organic electroluminescent devices, which are spontaneous light emitting devices and can be well used in various A display device. Background technique [0002] An organic electroluminescent device (hereinafter generally referred to as an organic EL device) is a spontaneous light emitting device that is characterized by higher luminance and higher legibility than a liquid crystal device capable of realizing a vivid image, and thus has been Research vigorously. [0003] In 1987, C.W.Tang et al. of EastmanKodak Co. have developed a stacked structure device including various materials taking on respective roles, and have put into practical use an organic EL device using an organic material. The above organic EL device is constituted by laminating layers of phosphors capable of transporting electrons and layers of aromati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/147C09K11/06H01L51/50
CPCC07D491/147C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1088C09K2211/1092C09B57/00C09B57/007H10K85/631H10K85/657H10K85/6572H10K85/6574H10K50/11H10K50/15H10K50/18H10K85/626H10K85/636H10K50/17
Inventor 横山纪昌神田大三林秀一
Owner HODOGOYA CHEMICAL CO LTD
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