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Arylamine derivative and use thereof

A derivative, arylamine technology, applied in the field of arylamine derivatives to achieve the effect of high charge transport

Active Publication Date: 2018-11-23
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, in recent years, not only the hole transport layer and the hole injection layer, but also the light emitting layer have been required to be produced by a wet method. The resistance to the solvent used in the composition has room for improvement with respect to the materials of the above-mentioned Patent Documents 1 to 4

Method used

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  • Arylamine derivative and use thereof
  • Arylamine derivative and use thereof
  • Arylamine derivative and use thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0180] As the organic solvent used in the preparation of the varnish for forming a hole injection layer, a highly soluble solvent capable of favorably dissolving the above-mentioned hole injection material and, if necessary, an electron-accepting dopant substance can be used. The high solubility solvent can be used individually by 1 type or in mixture of 2 or more types, and the usage-amount can be made into 5-100 mass % with respect to the whole solvent used for a varnish.

[0181] Examples of such highly soluble solvents include N-methylformamide, N,N-dimethylformamide, N,N-diethylformamide, N-methylacetamide, N,N- Dimethylacetamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolinone, etc.

[0182] It is preferable that both the charge-transporting substance and the electron-accepting dopant substance are completely dissolved in the above-mentioned organic solvent, or become a state of being uniformly dispersed. If it is considered that the space provided to the organic EL el...

Embodiment 1-1

[0220] [Example 1-1] Synthesis of Arylamine Derivatives 1

[0221] (1) The first process

[0222] [chemical 20]

[0223]

[0224] Put 5.77 g of 4-bromostyrene, 5.01 g of 4,4'-(hexafluoroisopropylidene) diphenylamine, and Pd(dba) into the flask 2After adding 0.174 g and 4.04 g of sodium tert-butoxide, the inside of the flask was replaced with nitrogen. Next, 75 mL of toluene and 2.0 mL (concentration: 67 g / L) of a toluene solution of di-tert-butyl(phenyl)phosphine prepared beforehand were added, and stirred at 80° C. for 1 hour. After the stirring was completed, the reaction mixture was cooled to room temperature, ethyl acetate and ion-exchanged water were mixed, and liquid separation was performed. The obtained organic layer was washed sequentially with ion-exchanged water and saturated brine, and dried over magnesium sulfate. It was filtered, and the solvent was distilled off under reduced pressure, then separated and purified by silica gel column chromatography (devel...

Embodiment 1-2

[0232] [Example 1-2] Synthesis of Arylamine Derivatives 2

[0233] [chem 22]

[0234]

[0235] Put 1.46g of the intermediate 1, 4-bromo-N,N-diphenylaniline 1.62g and Pd(dba) obtained in the first step above into the flask. 2 After adding 0.146 g and 0.676 g of sodium tert-butoxide, the inside of the flask was replaced with nitrogen. Next, 20 mL of toluene and 1.7 mL (concentration: 60 g / L) of a toluene solution of tri-tert-butylphosphine prepared in advance were added, and stirred at 80° C. for 2 hours. After the stirring was completed, the reaction mixture was cooled to room temperature, mixed with ion-exchanged water, and subjected to liquid separation treatment. The obtained organic layer was washed sequentially with ion-exchanged water and saturated brine, and dried over magnesium sulfate. This was filtered, and the solvent was distilled off under reduced pressure, followed by separation and purification by silica gel column chromatography (developing solvent: n-hexa...

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Abstract

This arylamine derivative represented by formula (1) exhibits good solubility to an organic solvent, and can be used to provide a thin film having solvent resistance, and also provides an organic EL element which exhibits good characteristics when the arylamine derivative is applied to a positive hole transport layer. (In the formula, each R independently represents a fluorine atom-containing alkyl group having 1-5 carbon atoms, each Ar1 independently represents an aryl group that has 6-20 carbon atoms, that is optionally substituted with Z1, and that has a crosslinking group, each Ar2 independently represents at least one aryl group selected from those represented by formulae (2)-(4), and Z1 represents a halogen atom, a nitro group, a cyano group, an amino group, or an alkyl group having1-20 carbon atoms optionally substituted with Z4.) (In the formula, Ar3 represents a hydrogen atom, or an alkyl group having 6-20 carbon atoms optionally substituted with Z2, and R1-R39 each independently represent a hydrogen atom, a halogen atom, etc.)

Description

technical field [0001] The present invention relates to arylamine derivatives and their use. Background technique [0002] In an organic electroluminescent (hereinafter referred to as organic EL) device, a charge-transporting thin film containing an organic compound is used as a light-emitting layer and a charge injection layer. In particular, the hole-injection layer is responsible for transferring charges between the anode and the hole-transporting layer or the light-emitting layer, and plays an important function in order to realize low-voltage drive and high-luminance of the organic EL element. [0003] The method of forming the hole injection layer is roughly divided into dry method represented by evaporation method and wet method represented by spin coating method. Comparing these methods, the wet method can efficiently manufacture a large area with high flatness. film. Therefore, a hole injection layer that can be formed by a wet method is desired at the present tim...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/54C07C209/10C07D209/88C09K11/06H01L51/50H05B33/10C07B61/00
CPCC07D209/88C07C211/56H10K85/111H10K85/636H10K85/631H10K85/6572H10K50/15C07C209/10C09K11/06H05B33/10C07B61/00H10K50/00H10K50/156H10K50/166C07C211/54
Inventor 大谷直树寺井诚弥
Owner NISSAN CHEM IND LTD
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