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New triphenylene derivative and organic electroluminescent element using said derivative [9, 10]

A derivative, benzo technology, applied in the field of organic electroluminescent devices, can solve the problems of unsatisfactory heat resistance and luminous efficiency, unsatisfactory current efficiency, and the problem of amorphousness, and achieve excellent Effects of hole transportability, improvement of luminous efficiency and power efficiency, and long service life

Inactive Publication Date: 2014-06-25
HODOGOYA CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] However, devices using these compounds to form a hole injection layer or a hole transport layer have still unsatisfactory improved heat resistance and luminous efficiency
In addition, their driving voltage is not low enough and their current efficiency is not satisfactory, and their amorphousness remains problematic

Method used

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  • New triphenylene derivative and organic electroluminescent element using said derivative [9, 10]
  • New triphenylene derivative and organic electroluminescent element using said derivative [9, 10]
  • New triphenylene derivative and organic electroluminescent element using said derivative [9, 10]

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0210] Synthesis of bis(biphenyl-4-yl)-{4-(benzo[9,10]phenanthrene-2-yl)phenyl}amine (synthesis of compound 66):

[0211]

[0212] Bis(biphenyl-4-yl)-(4-bromophenyl)amine 3.85g,

[0213] 4,4,5,5-tetramethyl-2-(benzo[9,10]phenanthrene-2-yl)-[1,3,2]dioxaborane 2.83g,

[0214] Toluene 59ml,

[0215] ethanol 15ml, and

[0216] 2M potassium carbonate aqueous solution 6ml,

[0217] It was added to a reaction vessel under a nitrogen atmosphere, and nitrogen gas was flowed for 30 minutes while being irradiated with ultrasonic waves.

[0218] Next, 0.19 g of tetrakis(triphenylphosphine)palladium was added thereto, and the mixture was heated and stirred at 72° C. for 4.5 hours. After leaving to cool to room temperature, 50 ml of methanol was added thereto, and the precipitated crude product was extracted by filtration.

[0219] The crude product was dissolved in 300 ml of toluene, purified by adsorption using 7.5 g of silica gel, concentrated under reduced pressure, and then cry...

Embodiment 2

[0231] Synthesis of (9,9-dimethyl-9H-fluoren-2-yl)-phenyl-{4-(benzo[9,10]phenanthrene-2-yl)phenyl}amine (synthesis of compound 15) :

[0232]

[0233] 3.89g of 4-bromophenyl(9,9-dimethyl-9H-fluoren-2-yl)-aniline,

[0234] 4,4,5,5-tetramethyl-2-(benzo[9,10]phenanthrene-2-yl)-[1,3,2]dioxaborolane 3.08g,

[0235] Toluene 59ml,

[0236] ethanol 15ml, and

[0237] 6.5ml of 2M potassium carbonate aqueous solution,

[0238] It was added to a reaction vessel under a nitrogen atmosphere, and nitrogen gas was flowed for 30 minutes while being irradiated with ultrasonic waves.

[0239] Next, 0.21 g of tetrakis(triphenylphosphine)palladium was added thereto, and the mixture was heated and stirred at 72° C. for 5.5 hours. After leaving to cool to room temperature, 50 ml of water and 30 ml of toluene were added thereto, and the organic layer was extracted by a liquid separation operation. The organic layer was dried over anhydrous magnesium sulfate, after which, it was concentrated...

Embodiment 3

[0256] Synthesis of (biphenyl-4-yl)-(9,9-dimethyl-9H-fluoren-2-yl)-{4-(benzo[9,10]phenanthrene-2-yl)phenyl}amine (Synthesis of Compound 67):

[0257]

[0258] (Biphenyl-4-yl)-(9,9-dimethyl-9H-fluoren-2-yl)amine 17.9g,

[0259] 2-(4-Bromophenyl)benzo[9,10]phenanthrene 19.0g,

[0260] Sodium tert-butoxide 5.72g, and

[0261] Toluene 200ml,

[0262] It was added to a reaction vessel under a nitrogen atmosphere, and nitrogen gas was flowed for 30 minutes while being irradiated with ultrasonic waves.

[0263] then,

[0264] Palladium acetate 0.22g and

[0265] Tri-tert-butylphosphine solution in toluene (50%w / v) 1.9ml,

[0266] Thereto was added, and the mixture was heated and stirred at 80 for 1.5 hours. After leaving to cool to room temperature, 100 ml of water and 100 ml of toluene were added thereto, and the organic layer was extracted by a liquid separation operation. The organic layer was dried over anhydrous magnesium sulfate, after which, it was concentrated unde...

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Abstract

This triphenylene derivative [9, 10] is represented by general formula (1) below. In the formula, Ar1 and Ar2 are aromatic bases. This compound has a structure in which an aromatic tertiary amine has been introduced into a triphenylene ring. This structure gives the structure the following characteristics: (A) excellent hole injection properties; (B) high hole mobility; (C) outstanding electron stopping power; (D) stable thin film status; and (E) excellent heat resistance. The derivative is effective as a hole transport substance used in organic EL elements.

Description

technical field [0001] The present invention relates to novel compounds (benzo[9,10]phenanthrene derivatives) suitable for organic electroluminescent devices that are self-luminous devices that can be advantageously used in various display devices, and to organic electroluminescent devices containing the above-mentioned compounds. layers of organic electroluminescent devices. Background technique [0002] Organic electroluminescence devices (hereinafter, generally referred to as organic EL devices) are self-luminous devices featuring higher luminance and higher legibility than liquid crystal devices capable of achieving sharp displays, and thus, have been intensively studied. [0003] In 1987, C.W.Tang et al. of Eastman Kodak Co. developed a device of a laminated structure including various materials to share various functions, and put an organic EL device using an organic material into practical use. The above-mentioned organic EL device is constituted by laminating layers...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/54C07C211/61C09K11/06H01L51/50H10K99/00
CPCH01L51/006H01L51/5048C07D277/60H01L51/5088C07D333/76C07D265/38C07C211/54C07C211/61C09K11/06H01L51/0052H01L51/0074H01L51/0054H01L51/0059C07C2103/42C07C2103/18C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1033C09K2211/1037C09K2211/1088C09K2211/1092C09B57/008C07C2603/18C07C2603/42H10K85/615H10K85/622H10K85/655H10K85/631H10K85/636H10K85/626H10K85/633H10K85/6576H10K50/15H10K50/181H10K50/17H10K50/00H10K50/11H10K50/18
Inventor 横山纪昌桦泽直朗大熊宽史林秀一高桥英治
Owner HODOGOYA CHEMICAL CO LTD
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