Organic electroluminescent device

An electroluminescent element and electroluminescent technology, applied in electrical elements, luminescent materials, organic chemistry, etc., can solve problems such as insufficient, low driving voltage luminous efficiency, and reduced element characteristics.

CN113396200APending Publication Date: 2021-09-14HODOGOYA CHEMICAL CO LTD
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Publication Date
2021-09-14

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Abstract

The object of the invention is to provide a material for a highly efficient and highly durable organic EL device, the material having excellent hole injection / transport capability, electron-blocking ability, thin film stability, and durability, and to further provide an organic EL device having high efficiency, low driving voltage, and long service life by combining the material and various organic EL device materials having excellent hole injection / transport capability, electron-blocking ability, thin film stability, and durability, such that the properties of each material can be effectively exhibited. The arylamine compound having a specific structure according to the invention has excellent hole injection / transport capability, thin film stability, and durability, and can thus be selected as a material for a hole transport layer that efficiently transports holes injected from the positive electrode side. Moreover, various organic EL devices obtained by combining materials such as the electron transport material having a specific structure exhibit good device characteristics.
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Description

technical field

[0001] The present invention relates to an organic electroluminescent element as a self-luminescent element suitable for various display devices, and in detail, relates to an organic electroluminescent element (hereinafter, simply referred to as an organic EL element) using a specific arylamine compound. . Background technique

[0002] Since the organic EL element is a self-luminous element, it is brighter than a liquid crystal element, has excellent visibility, and can realize a clear display, so it has been actively studied.

[0003] In 1987, C.W.Tang of Eastman Kodak Company developed a laminated structural element in which each material shared various functions, thus making the organic EL element using organic materials a practical element. They laminated a phosphor capable of transporting electrons and an organic substance capable of transporting holes, injected the charges of the two into the phosphor layer to make it emit light, and obtained 1000 cd / m...

Examples

Embodiment 1

[0227]

[0228] 22.4 g of 4-(naphthalen-1-yl)aniline, 19.8 g of 3-bromobiphenyl, 12.2 g of sodium tert-butoxide, and 230 mL of toluene were added to a nitrogen-substituted reaction vessel, and nitrogen gas was blown in while irradiating ultrasonic waves for 30 minutes. 0.8 g of tris(dibenzylideneacetone)dipalladium and 0.5 g of 2,2'-bis(diphenylphosphine)-1,1'-binaphthyl were added, heated, and stirred at 110°C for 16 hours. After removing insoluble matter by filtration, the filtrate was concentrated. The residue was purified by column chromatography to obtain 25.4 g (yield 75.6%) of 4-(naphthalen-1-yl)phenyl-biphenyl-3-amine as a light yellow viscous substance.

[0229] 23.9 g of 4-(naphthalen-1-yl)phenyl-biphenyl-3-amine and 240 mL of dimethylformamide were added to the nitrogen-substituted reaction vessel, and cooled in an ice bath. 11.6 g of N-bromosuccinimide was added in portions over 30 minutes, followed by stirring at 5° C. for 4 hours. Water was added, extracted w...

Embodiment 2

[0238]

[0239] Add (1,1':2',1"-terphenyl-4'-yl)amine 17.2g, 2-(4-bromophenyl)naphthalene 18.0g, tert-butoxy Sodium 9.2g, toluene 270mL, while irradiating ultrasonic waves for 30 minutes, pass nitrogen gas. Add tris(dibenzylideneacetone) dipalladium 1.2g, 2,2'-bis(diphenylphosphine)-1,1'-bis 0.8 g of naphthalene was heated and stirred at 110° C. for 16 hours. After removing the insolubles by filtration, the filtrate was heated, and at 80° C., adsorption purification using activated clay and silica gel was carried out, and heating and filtration was carried out. The filtrate was concentrated and passed through toluene-heptyl The residue was purified by recrystallization in alkanes to obtain {4-(naphthalene-2-yl)phenyl}-(1,1':2',1"-terphenyl-5'-yl)amine as a yellow-white powder Body 24.3g (yield 85.4%).

[0240] Add 24.3 g of {4-(naphthalene-2-yl)phenyl}-(1,1':2',1"-terphenyl-5'-yl)amine, 9-bromo 15.4g of phenanthrene, 10.4g of sodium tert-butoxide, 240mL of toluene, while i...

Embodiment 3

[0247]

[0248] The {4"-(naphthalene-1-yl)-1,1':2',1"-terphenyl-5'-yl}-{4-(naphthalene-1-yl)phenyl group of Example 1 } amine to {4"-(naphthalen-1-yl)-1,1':2',1"-terphenyl-5'-yl}-{4-(naphthalen-2-yl)phenyl} Amines, the same procedure was performed to give {4-(naphthalene-2-yl)phenyl}-(phenanthrene-9-yl)-{4"-(naphthalene-1-yl)-1,1':2', 4.9 g of white powder of 1"-terphenyl-5'-yl}amine (compound 1-17) (yield 40%).

[0249] The structure of the obtained white powder was identified using NMR.

[0250] use 1 H-NMR (CDCl 3 ) detected the following 39 hydrogen signals.

[0251] δ(ppm)=8.76-8.86(2H), 8.24-8.28(1H), 8.06(1H), 7.85-7.95(8H), 7.36-7.78(19H), 7.19-7.31(8H).

[0252] [chem 21]

[0253]