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Organic electroluminescent element

An electroluminescent element and luminescent technology, applied in the direction of electrical components, electric solid-state devices, circuits, etc., can solve problems that cannot be said to be sufficient, and achieve low driving voltage, improved injection and transmission efficiency, and improved hole transport efficiency. Effect

Active Publication Date: 2018-09-28
HODOGOYA CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, for elements using these compounds for the hole injection layer or the hole transport layer, although improvements in low driving voltage, heat resistance, and luminous efficiency have been achieved, they are still not sufficient. Higher driving voltage and higher luminous efficiency

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0387] Hereinafter, although an Example demonstrates embodiment of this invention concretely, this invention is not limited to the following Example.

Synthetic example 1

[0388]

[0389] Synthesis of 4-bis(biphenyl-4-yl)amino-4'-{(biphenyl-4-yl)-phenylamino}-2-phenyl-biphenyl:

[0390] In a nitrogen-purged reaction vessel add

[0391]

[0392]

[0393] , heated, and stirred overnight at 100°C to obtain a reaction solution. The reaction liquid was cooled, and the organic layer was extracted by a liquid separation operation. The extracted organic layer was concentrated to obtain a crude product. The crude product was purified by column chromatography (carrier: silica gel, eluent: dichloromethane / heptane). As a result, 5.30 g of white powder of compound 1-1 was obtained (yield 37%).

[0394] For the obtained white powder, the structure was identified using NMR. use 1 H-NMR (CDCl 3 ) detected the following 44 hydrogen signals.

[0395] δ(ppm)=7.65-7.60(5H)

[0396] 7.59-7.53(5H)

[0397] 7.52-7.40(9H)

[0398] 7.39-7.21(15H)

[0399] 7.20-7.10(5H)

[0400] 7.09-6.91(5H)

[0401] [chemical 14]

[0402]

Synthetic example 2

[0403]

[0404] 4-{(biphenyl-4-yl)-(4-naphthalen-1-yl-phenyl)amino}-4'-{(biphenyl-4-yl)-phenylamino}-2-phenyl- Synthesis of biphenyl:

[0405] In Synthesis Example 1, (biphenyl-4-yl)-(6-bromobiphenyl-3-yl) was used instead of bis(biphenyl-4-yl)-(6-bromobiphenyl-3-yl)amine )-(4-naphthalen-1-yl-phenyl)amine, reacted under the same conditions. As a result, 9.70 g of an off-white powder of Compound 1-3 was obtained (69% yield).

[0406] For the obtained off-white powder, use NMR to identify the structure. use 1 H-NMR (CDCl 3 ) detected the following 46 hydrogen signals.

[0407] δ(ppm)=8.07(1H)

[0408] 7.93(1H)

[0409] 7.87(1H)

[0410] 7.67-7.54(7H)

[0411] 7.54-7.11(31H)

[0412] 7.69-6.92(5H)

[0413] [chemical 15]

[0414]

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Abstract

The present invention provides an organic EL element having, in the indicated sequence, at least an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transportlayer, and a cathode, the organic EL element being characterized in that the hole injection layer contains an arylamine compound represented by general formula (1) and an electron acceptor. The organic EL element according to the present invention provides a higher light emission efficiency and a better durability than heretofore while retaining the same low drive voltage as heretofore.

Description

technical field [0001] The present invention relates to an organic electroluminescent element as a self-luminous element suitable for various display devices, and in particular, to an organic electroluminescent element using a specific arylamine compound doped with an electron acceptor (hereinafter sometimes referred to as called organic EL elements). Background technique [0002] Since the organic EL element is a self-luminous element, it is bright and has excellent visibility compared with a liquid crystal element, and can perform a clear display. Therefore, active research is conducted. [0003] In 1987, C.W.Tang of Eastman Kodak Co., Ltd. developed a layered structure element in which various functions are distributed to each material, making the organic EL element using organic materials a practical element. An organic EL element is formed by laminating a phosphor capable of transporting electrons and an organic substance capable of transporting holes. As a result, t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01L51/50
CPCH10K85/631H10K85/636H10K85/626H10K85/633H10K50/17H10K50/11H10K85/615H10K85/654H10K85/6572H10K50/125H10K50/15H10K50/16H10K50/18H10K50/171H10K50/81H10K50/82H10K2101/10
Inventor 横山纪昌林秀一桦泽直朗山本刚史
Owner HODOGOYA CHEMICAL CO LTD
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