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Organic electroluminescent element

An electroluminescent element, organic technology, applied in electrical elements, organic semiconductor devices, organic chemistry, etc., can solve the problems of insufficient sealing of triplet excitons, shortened component life, and reduced luminous efficiency.

Active Publication Date: 2020-06-26
HODOGOYA CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] However, these monoamine compounds have higher hole mobility than carbazole derivatives, but have a problem of low T1
Therefore, the confinement of triplet excitons becomes insufficient, and there is concern about a reduction in luminous efficiency due to exciton deactivation and a shortened lifetime of the device.

Method used

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  • Organic electroluminescent element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0258]

[0259] After adding 50.7 g of 1,3,5-triphenylbenzene and chloroform to the nitrogen-substituted reaction container, 29.1 g of bromine was added, and it stirred at room temperature for 16 hours. After adding saturated aqueous sodium sulfite solution and stirring, liquid separation was performed to obtain an organic layer. The organic layer was dehydrated over magnesium sulfate, and concentrated under reduced pressure to obtain a crude product. Hexane was added to the crude product, and dispersion washing was performed to obtain 55.0 g of white powder of 2-bromo-1,3,5-triphenylbenzene (yield: 86%).

[0260] The obtained 2-bromo-1,3,5-triphenylbenzene 5.0g, 4-{N,N-bis(biphenyl-4-yl)amino}phenylboronic acid 6.9g, tripotassium phosphate 8.3g, 90 ml of 1,4-dioxane and 10 ml of water were added to the nitrogen-substituted reaction vessel, and nitrogen gas was passed through for 30 minutes. 0.087 g of palladium (II) acetate and 0.25 g of tricyclohexylphosphine were added,...

Embodiment 2

[0267]

[0268] 38.0 g of N-(4-bromophenyl)-4-biphenylamine, 25.5 g of 4-biphenylboronic acid, 32.4 g of potassium carbonate, 3000 ml of toluene, 76 ml of ethanol, and 113 ml of water were added to the nitrogen-substituted reaction vessel. Nitrogen was bubbled through for 30 minutes. 2.7 g of tetrakis(triphenylphosphine)palladium was added, heated, and stirred at 73° C. for 5 hours. 100 ml of water was added, and the precipitated solid was obtained by filtration. Add o-dichlorobenzene, heat and dissolve the obtained solid, add silica gel, stir, and perform hot filtration. The filtrate was concentrated under reduced pressure and the precipitated solid was obtained by filtration to give N-(biphenyl-4-yl)-N-(1,1':4',1"-terphenyl-4-yl)amine 20.1 g of yellow powder (yield 43%).

[0269] The obtained N-(biphenyl-4-yl)-N-(1,1':4',1"-terphenyl-4-yl)amine 20.0g, iodobenzene 15.4g, copper powder 0.3g, carbonic acid Add 13.9 g of potassium, 1.2 g of 3,5-di-tert-butyl salicylic acid...

Embodiment 3

[0279]

[0280]Add N-(biphenyl-4-yl)-N-(4-bromophenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)amine to a nitrogen-displaced reaction vessel 71.9g, 360ml of tetrahydrofuran, cooled to -78°C. 100 ml of a hexane solution (1.6 M) of n-butyllithium was slowly added dropwise, and stirred at the same temperature for 1 hour. Next, 19 ml of trimethyl borate was slowly added dropwise, followed by stirring at the same temperature for 1 hour. After raising the temperature to room temperature, the mixture was further stirred for 1 hour, and then, 1N aqueous hydrochloric acid solution was added thereto, followed by stirring for 1 hour. After performing a liquid separation operation to obtain an organic layer, the organic layer was dehydrated with anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain a crude product. Purify the obtained crude product by crystallization using a mixed solution of ethyl acetate / n-hexane to obtain 4-{N-(biphenyl-4-yl)-N-(9,9-dimethyl-9...

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Abstract

The present invention aims to provide an organic compound which functions as a material for a highly efficient and highly durable organic EL element, exhibits the excellent hole injection and hole transport performance, has electronic stopping power, and exhibits the excellent properties of being highly stable as a thin film and having high light emission efficiency; and the organic EL element which uses the compound and exhibits high durability and high efficiency. The organic EL element is characterized by being provided with a first hole transport layer, a second hole transport layer, a green light-emitting layer, and an electron transport layer which are positioned between a positive electrode and a negative electrode orderly from the positive electrode side, and comprising an arylamine compound represented by general formula (1) and contained in one or more layers among the layered films positioned between the electron transport layer and the first hole transport layer or the second transport layer. (In the formula, Ar1, Ar2, Ar3 and Ar4 may be identical to or different from one another, and represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted orunsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group. L1 represents a substituted or unsubstituted aromatic hydrocarbon divalent group, a substituted or unsubstituted aromatic heterocyclic divalent group, or a substituted or unsubstituted condensed polycyclic aromatic divalent group. R1, R2 and R3 represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a C1-6 straight-chain or branched alkyl group which may have a substituent group, a C5-10 cycloalkyl group which may have a substituent group, a C2-6 straight-chain or branched alkenyl group which may have a substituent group, a C1-6 straight-chain or branched alkyloxy group which may have a substituent group, a C5-10 cycloalkyloxy group which may have a substituent group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group. n is an integer of 1-3, inclusive.)

Description

technical field [0001] The present invention relates to a compound suitable for an organic electroluminescence element (hereinafter simply referred to as an organic EL element) as a self-luminous element suitable for various display devices and the element. Specifically, it relates to an organic electroluminescent element using an arylamine compound. EL elements. 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, so active research has 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 will be able to transport electrons phosphor, tris (8-hydroxyquinoline) aluminum (hereinafter referred to as Alq 3 ) and an aromatic amine com...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01L51/50C07D209/88C07D307/91C09K11/06C07C211/54C07C211/61C07F15/00
CPCC07C211/54C07C211/61C07D209/88C07D307/91C07F15/00C09K11/06C09K2211/185C07D253/04C07D213/16C07D239/26C07D213/06C07D401/14C07D405/14C07D403/04C07D403/14C07D401/04C07D405/04C07D401/10C07D413/10C07D413/14C07D413/04C07D263/56C07D471/04C07D209/86H10K85/631H10K85/636H10K85/633H10K85/6572H10K85/6574H10K85/342H10K50/11H10K2101/10H10K50/156H10K50/17H10K2101/90H10K85/00H10K85/657H10K50/16C07C2603/18C07C211/57C07F15/0033C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1018C09K2211/1029H10K85/615H10K85/626
Inventor 望月俊二大熊宽史山本刚史骏河和行
Owner HODOGOYA CHEMICAL CO LTD
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