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Compound with triphenylamine structure, and organic electroluminescent element

A technology of arylamine compound and triphenylamine, which is applied in the field of compounds with triphenylamine structure and organic electroluminescent devices, and can solve the problems that have never been heard of, and the material of the hole transport layer is not suitable, etc.

Inactive Publication Date: 2012-11-14
HODOGOYA CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this is for the material of the light-emitting layer, not for the material of the hole transport layer, so no examples of materials applied to the hole transport layer have been heard

Method used

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  • Compound with triphenylamine structure, and organic electroluminescent element
  • Compound with triphenylamine structure, and organic electroluminescent element
  • Compound with triphenylamine structure, and organic electroluminescent element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0222] 5 )-Amino]biphenyl (Compound 5) Synthesis>

[0223] Add 30.00g of aniline-2,3,4,5,6-d5 and 50ml of acetic acid to a nitrogen-substituted reaction vessel, heat to 70°C while stirring, then add 34.7ml of acetic anhydride dropwise, and further heat at 70°C Stirring was continued for 4 hours. After cooling to room temperature, the reaction solution was poured into ice water, and the precipitated crystals were separated by filtration to obtain 48.71 g of light brown crystals. On the other hand, the filtrate was transferred to a separatory funnel, and 1000 ml of toluene was added for extraction operation. The extract was concentrated and dried to obtain 4.05 g of brown crystals. These crystals were combined and dried under reduced pressure to obtain 41.33 g (yield 96.5%) of acetanilide-2,3,4,5,6-d 5 of brown crystals.

[0224] 35.00g of the resulting acetanilide-2,3,4,5,6-d 5 , 48.50 g of 4-bromobiphenyl, 1.32 g of copper powder, 43.14 g of potassium carbonate, 6.53 g of ...

Embodiment 2

[0230] 9 Synthesis of -4-yl)-phenylamino}biphenyl (compound 49)>

[0231] In the nitrogen replaced reaction vessel, add 16.08g of bromobenzene-d 5 , 13.79g (phenyl-d 5 ) boric acid, 20.46g of potassium carbonate, 74ml of water, 160ml of toluene, and 40ml of ethanol, while irradiating ultrasonic waves, nitrogen gas was introduced for 30 minutes. Add 2.28 g of tetrakis(triphenylphosphine)palladium, heat and stir under reflux for 7.5 hours. After allowing to cool to room temperature, a liquid separation operation was performed, and the organic layer was collected, dried with magnesium sulfate, and then concentrated to obtain 22.27 g of a black crude product. The crude product was purified by column chromatography (carrier: silica gel, eluent: n-hexane) to obtain 14.07 g (yield 86%) of white crystals of biphenyl-d10.

[0232] 14.07g of the resulting biphenyl-d 10 , 0.28g of iron(III) chloride, 2.2ml of bromine, and 70ml of chloroform were added to the reaction vessel replaced ...

Embodiment 3

[0238] 4 Synthesis of )-4-yl]amino}biphenyl (compound 18)>

[0239] In a reaction vessel replaced with nitrogen, add 20.0 g (biphenyl-4-yl)-(phenyl-d 5 ) amine and 400ml of DMF were dissolved, and then 4.7g of N-bromosuccinimide was added under ice cooling. While adding 9.4 g of N-bromosuccinimide in two portions, the reaction temperature was raised to room temperature. After stirring for 3 hours, the reaction solution was added dropwise to 2000 ml of water, and the precipitated solid was collected by filtration. 1000 ml of toluene was added to the obtained solid to dissolve it, and after drying with magnesium sulfate, a filtration operation was performed, and the filtrate was concentrated. Add 200ml of n-hexane to the obtained concentrate, carry out dispersion washing, dry under reduced pressure overnight, obtain 23.4g (yield 89.0%) (biphenyl-4-yl)-4-bromo(phenyl-2,3, 5,6-d 4 ) Red-black solid of amine.

[0240] 23.0 g of the resulting (biphenyl-4-yl)-4-bromo(phenyl-2,3,...

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Abstract

Provided is an organic compound which is useful as a material for a highly efficient and durable organic EL element. The organic compound has excellent hole injection / transport performance and electron-stopping power, and is stable in the form of thin film and resistant to heat. Also provided is a highly efficient and durable organic EL element using the compound. An arylamine compound with triphenylamine structure, as represented by general formula (1) or (2); and an organic electroluminescent element which includes one pair of electrodes and one or more organic layers disposed therebetween, characterized in that the compound is used in at least one of the organic layers as the constituent material.

Description

technical field [0001] The present invention relates to a compound suitable for an organic electroluminescence device (hereinafter simply referred to as an organic EL device) as a self-luminous device applicable to various display devices and the device, more particularly to a compound having a triphenylamine structure and the use of the device. Compound organic EL devices. Background technique [0002] Since the organic EL device is a self-luminous device, it is brighter than a liquid crystal device, has better visibility, and can realize a bright display, and research has been actively conducted on this basis. [0003] In 1987, C.W.Tang et al. of Eastman Kodak Company made organic EL devices using organic materials practical by developing a stacked structure device that shared various functions on various materials. They used the electron-transportable phosphor tris(8-quinolinolato)aluminum (hereinafter referred to as Alq 3 ) is laminated with an aromatic amine compound ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/54H01L51/50
CPCH01L51/5096C07D209/86C07C211/56C09K11/06C07C211/54H01L51/5048C07B2200/05C09K2211/1014H01L51/0059H01L51/5088C07C2103/18C07C2603/18H10K85/631H10K50/14H10K50/17H10K50/181H10K50/18
Inventor 横山纪昌长冈诚加濑幸喜小泽信吾草野重
Owner HODOGOYA CHEMICAL CO LTD
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