Organic electroluminescent element

An electroluminescent element and luminescent technology, applied in the direction of electrical components, organic chemistry, luminescent materials, etc., can solve problems such as unexpectable luminous efficiency, insufficient electron barrier property, and reduced component characteristics, and achieve excellent electron blocking ability , Excellent electron blocking ability, and the effect of low driving voltage

Pending Publication Date: 2022-06-03
HODOGOYA CHEMICAL CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

NPD has good hole transport ability, but its glass transition temperature (Tg), which is an indicator of heat resistance, is as low as 96°C, and crystallization occurs under high temperature conditions, resulting in degradation of device characteristics (see, for example, Non-Patent Document 4).
[0011] In addition, in the aromatic amine derivatives described in the above-mentioned patent documents, it is known that the hole mobility is 10 -3 cm 2 Compounds with excellent mobility above / Vs (for example, refer to Patent Document 1 and Patent Document 2), but due to insufficient electron barrier properties, part of the electrons pass through the light-emitting layer, and improvement in luminous efficiency cannot be expected. Higher efficiency requires materials with higher electron barrier properties, more stable films, and high heat resistance
In addition, there are reports of highly durable aromatic amine derivatives (for example, refer to Patent Document 3), and they are used as charge transport materials for electrophotographic photoreceptors, but there are no examples of their use as organic EL devices.
[0012] As compounds having improved properties such as heat resistance and hole injection properties, arylamine compounds having a substituted carbazole structure have been proposed (for example, refer to Patent Document 4 and Patent Document 5), and the use of these compounds in the hole injection layer or For elements of the hole transport layer, although improvements in heat resistance and luminous efficiency have been achieved, it is still not sufficient, and further low driving voltage and further high luminous efficiency are sought.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0125]

[0126] In the reaction vessel was added (4-naphthalen-2-yl-phenyl)-[1,1';2',1"]terphenyl-4'-yl-amine: 15.0 g, 9-(4-bromo- Phenyl)-phenanthrene: 12.3g, sodium tert-butoxide: 4.8g, toluene: 240mL, pass nitrogen gas while irradiating ultrasonic waves for 30 minutes. Then, add palladium acetate (II): 0.1g, tri(tert-butyl) Phosphine: 0.3g, refluxed and stirred for 4 hours. After natural cooling, the filtrate obtained by filtration was concentrated under reduced pressure to obtain a crude product. The crude product obtained was purified by recrystallization utilizing a toluene solvent to obtain (4-naphthalene- White powder of 2-yl-phenyl)-(4-phenanthren-9-yl-phenyl)-[1,1';2',1"]terphenyl-4'-yl-amine (1-2) Body: 18.7 g (80% yield).

[0127] [hua 5]

[0128]

[0129] The structure of the obtained white powder was identified using NMR.

[0130] use 1 H-NMR (CDCl 3 ) detected the following 37 hydrogen signals.

[0131] δ(ppm)=8.81(1H), 8.76(1H), 8.11(1H), 8.09(1H), 7...

Embodiment 2

[0133]

[0134] In the reaction vessel was added (4-phenanthren-9-yl-phenyl)-[1,1';2',1"]terphenyl-4'-yl-amine: 15.0 g, 1-(4-bromo- Phenyl)-naphthalene: 9.4g, sodium tert-butoxide: 4.3g, toluene: 210mL, while irradiating ultrasonic wave for 30 minutes and passing nitrogen gas. Then, add palladium acetate (II): 0.1g, tri(tert-butyl) Phosphine: 0.1 g, refluxed and stirred overnight. After natural cooling, the filtrate obtained by filtration was concentrated under reduced pressure to obtain a crude product. The obtained crude product was subjected to column chromatography (carrier: silica gel, eluent: dichloromethane). / n-heptane) was purified to obtain (4-naphthalen-1-yl-phenyl)-(4-phenanthren-9-yl-phenyl)-[1,1';2',1"]triple White powder of phenyl-4'-yl-amine (1-3): 15.9 g (yield 76%).

[0135] [hua 6]

[0136]

[0137] The structure of the obtained white powder was identified using NMR.

[0138] use 1 H-NMR (CDCl 3 ) detected the following 37 hydrogen signals.

[013...

Embodiment 3

[0141]

[0142] Add biphenyl-4-yl-(6-bromo-[1,1';4',1"]terphenyl-3-yl)-(4-phenanthren-9-yl-phenyl)- Amine: 10.0 g, phenylboronic acid: 2.5 g, potassium carbonate: 3.6 g, toluene: 80 mL, ethanol: 30 mL, H 2O: 30 mL, and nitrogen gas was introduced while irradiating ultrasonic waves for 30 minutes. Then, tetrakis(triphenylphosphine)palladium(0):0.3 g was added, and the mixture was stirred under reflux overnight. After being left to cool, the organic layer was subjected to liquid separation extraction by a liquid separation operation, and concentrated under reduced pressure to obtain a crude product. The obtained crude product was purified by crystallization using a dichloromethane / acetone mixed solvent to obtain biphenyl-4-yl-(4-phenanthren-9-yl-phenyl)-[1,1';2', White powder of 1"; 4", 1"'] tetraphenyl-4'-yl-amine (1-4): 5.4 g (yield 54%).

[0143] [hua 7]

[0144]

[0145] The structure of the obtained white powder was identified using NMR.

[0146] use 1 H-NMR (CDC...

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Abstract

The purpose of the present invention is to provide, as a material for organic EL elements having high efficiency and high durability, a material for organic EL elements having excellent hole injection / transport performance, electron blocking ability, stability in a thin film state, and durability. This material is combined with various materials for organic EL elements having excellent hole and electron injection / transport performance, electron blocking ability, stability in a thin film state, and durability so that the characteristics of each material can be effectively exhibited, thereby providing an organic EL element having high efficiency, low driving voltage, and long life. The arylamine compound having a specific structure according to the present invention has excellent hole injection / transport capabilities, stability of a thin film, and durability, and thus can efficiently transport holes injected from the anode side by selecting the arylamine compound having a specific structure as a material for a hole transport layer. In addition, various organic EL elements in which electron transport materials having a specific structure or the like are combined exhibit good element characteristics.

Description

technical field [0001] The present invention relates to an organic electroluminescence element as a self-luminous element suitable for various display devices, and more specifically, to an organic electroluminescence element (hereinafter simply referred to as an organic EL element) using a specific arylamine compound. Background technique [0002] Since an organic EL element is a self-luminous element, it is brighter than a liquid crystal element, it is excellent in visibility, and it can perform a clear display, and therefore active research has been carried out. [0003] In 1987, C.W. Tang and others of Eastman Kodak Company developed a layered structure element in which various functions were shared among materials, thereby making an organic EL element using an organic material a practical element. They layered a phosphor capable of transporting electrons and an organic substance capable of transporting holes, injected the charges of both into the phosphor layer to emit l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01L51/50H01L51/54C07C211/54C07C209/10C07F5/02C09K11/06C07B59/00
CPCC07C211/54C07C209/10C07F5/02C09K11/06C07B59/002C09K2211/1011C09K2211/1014C09K2211/1055C07B2200/05H10K85/626H10K85/615H10K85/631H10K85/657H10K50/15H10K85/658H10K50/156H10K85/633H10K85/322H10K50/12C07C2603/26C07C211/58C07F5/027C09K2211/1007C09K2211/1018
Inventor 骏河和行加濑幸喜山本刚史林秀一车淳旭朱性壎梁炳善金志丸
Owner HODOGOYA CHEMICAL CO LTD
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