Organic el element, amine compound having benzoazole ring structure, and method in which said amine compound is used in capping layer of organic el element

A technology of benzoxazole ring and capping layer, applied in organic chemistry, organic semiconductor devices, electrical components, etc., can solve the problems of reduced light extraction efficiency, reduced alignment accuracy, deformation of metal masks, etc., and achieves the highest extraction efficiency. The effect of optimization, improved extraction efficiency, and excellent light resistance

Active Publication Date: 2020-08-21
HODOGOYA CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] So far, it has been proposed to use a high-precision metal mask for the formation of the capping layer. If it is used under high temperature conditions, there is the following problem: deformation due to heat occurs in the metal mask, and thus the accuracy of the alignment is reduced. reduce
Therefore, ZnSe has a melting point as high as 1100°C or higher (for example, refer to Non-Patent Document 3), and if it is a high-precision metal mask, it cannot be vapor-deposited at the correct position, which may also affect the light-emitting element itself.
Furthermore, even if the sputtering method is used to form a film, it will affect the light-emitting element, so the capping layer made of inorganic materials is not suitable for use.
[0009] In addition, as a capping layer for adjusting the refractive index, tris(8-hydroxyquinoline)aluminum (hereinafter abbreviated as Alq 3 ) (for example, referring to non-patent literature 2), known Alq 3 It is an organic EL material generally used as a green light-emitting material or an electron transport material. It has weak absorption near 450nm used in a cyan light-emitting material. Therefore, in the case of a cyan light-emitting element, there is also a decrease in color purity and light extraction. The problem of reduced efficiency
[0010] In addition, in the case of an element produced with a conventional capping layer, sunlight with a wavelength of 400nm to 410nm passes through and affects the material inside the element, resulting in a reduction in color purity and light extraction efficiency.

Method used

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  • Organic el element, amine compound having benzoazole ring structure, and method in which said amine compound is used in capping layer of organic el element
  • Organic el element, amine compound having benzoazole ring structure, and method in which said amine compound is used in capping layer of organic el element
  • Organic el element, amine compound having benzoazole ring structure, and method in which said amine compound is used in capping layer of organic el element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0136]

[0137] Add 2-(4-bromophenyl)-2H-benzotriazole: 3.7g, bis-(biphenyl-4-yl)-{4-(4,4,5, 5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl}-amine: 9.4g, toluene: 80mL, ethanol: 20mL, then, add pre-made potassium carbonate: 5.6 g dissolved in H 2 O: an aqueous solution in 20 mL, nitrogen gas was passed through while irradiating ultrasonic waves for 30 minutes. Tetrakis(triphenylphosphine)palladium: 0.8 g was added, and the mixture was stirred under heating and reflux for 4 hours. After natural cooling, add H 2 O, the organic layer was extracted by liquid separation, and concentrated under reduced pressure to obtain a crude product. Purify the obtained crude product by column chromatography (carrier: silica gel, eluent: toluene / n-hexane) to obtain {4'-(benzotriazol-2-yl)biphenyl-4-yl}-bis- Yellow powder of (biphenyl-4-yl)-amine (compound 17): 6.4 g (85% yield).

[0138] [chemical 20]

[0139]

[0140] The structure of the obtained yellow powder was identified using N...

Embodiment 2

[0144]

[0145] Add 2-(4-bromophenyl)-2H-benzotriazole: 9.0 g, bis-(biphenyl-4-yl)-amine: 9.6 g, sodium tert-butoxide: 4.3 g, Toluene: 150 ml, while irradiating ultrasonic waves for 30 minutes, blow nitrogen gas. Palladium(II) acetate: 0.1 g and a 50% (w / v) toluene solution of tri-(tert-butyl)phosphine: 0.24 ml were added, and the mixture was stirred under reflux for 2 hours. After natural cooling, add toluene, carry out dispersion washing, filter the insoluble matter, add silica gel and activated clay to the filtrate, and carry out adsorption and purification. The adsorbent was removed by filtration and the filtrate was concentrated to give crude product. The crude product is purified by crystallization in a mixed solvent of toluene / acetone, and the precipitated solid is obtained to obtain {4-(benzotriazol-2-yl)phenyl}-bis(biphenyl-4-yl)-amine (compound 6) Yellow powder: 11.6 g (75.3% yield).

[0146] [chem 21]

[0147]

[0148] The structure of the obtained yellow p...

Embodiment 3

[0152]

[0153] Add 2-(4-bromophenyl)-2H-benzotriazole: 8.3g, (biphenyl-4-yl)-(9,9-dimethyl-9H-fluoren-2-yl) into the reaction vessel )-amine: 10.0 g, sodium tert-butoxide: 4.0 g, toluene: 150 ml, nitrogen gas was blown while irradiating ultrasonic waves for 30 minutes. Palladium(II) acetate: 0.1 g and a 50% (w / v) toluene solution of tri-(tert-butyl)phosphine: 0.22 ml were added, and the mixture was stirred under reflux for 2 hours. After natural cooling, add toluene, carry out dispersion washing, filter the insoluble matter, add silica gel and activated clay to the filtrate, and carry out adsorption and purification. The adsorbent was removed by filtration and the filtrate was concentrated to give crude product. The crude product was purified by crystallization with acetone, and the precipitated solid was obtained to obtain {4-(benzotriazol-2-yl)phenyl}-(biphenyl-4-yl)-9,9-dimethyl- Yellow powder of 9H-fluoren-2-yl)-amine (compound 7): 12.3 g (80.4% yield).

[0154] [che...

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Abstract

An organic EL element having at least a positive electrode, a hole transport layer, a light-emitting layer, an electron transport layer, a negative electrode, and a capping layer in the stated order,wherein the capping layer contains an amine compound having a benzoazole ring structure represented by general formula (A-1).

Description

technical field [0001] The present invention relates to compounds and devices suitable for use in organic electroluminescence devices (hereinafter simply referred to as organic EL devices) as self-luminous devices suitable for various display devices. Specifically, it relates to compounds having a benzoxazole ring structure, An organic EL device using the compound and a method of using the compound in the organic EL device. 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 perform a clear display. Active research has therefore been conducted. [0003] In 1987, C.W.Tang and others from Eastman Kodak Company developed a laminated structural element in which various functions are distributed to each material, thus making organic EL elements using organic materials practical elements. They layered a phosphor capable of transporting electrons and an organic subst...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H05B33/02C07D249/20C07D403/10H01L51/50
CPCC07D249/20C07D401/10C07D413/10C07D417/10C07D403/04C07D403/12C07D403/10C07D403/14C07D405/14C07D409/14H10K50/858H10K50/844H10K2102/3026H05B33/02H10K85/636H10K85/654H10K50/00H10K85/631H10K50/15H10K50/16H10K50/171
Inventor 加濑幸喜山本刚史望月俊二林秀一
Owner HODOGOYA CHEMICAL CO LTD
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