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Organic electroluminescence element and its manufacturing method

An electroluminescence element and luminescence technology, which is applied in the direction of electroluminescence light sources, electrical components, organic semiconductor devices, etc., can solve problems such as degradation and cumbersome manufacturing process of light-emitting elements

Active Publication Date: 2017-07-18
NIPPON HOSO KYOKAI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, an organic electroluminescent element in which all the layers between the cathode and anode are formed of organic compounds tends to be easily degraded by oxygen and water, and tight sealing is essential to prevent their intrusion.
This becomes the reason why the manufacturing process of the organic electroluminescence element becomes cumbersome

Method used

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  • Organic electroluminescence element and its manufacturing method
  • Organic electroluminescence element and its manufacturing method
  • Organic electroluminescence element and its manufacturing method

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0651] (Synthesis of 2,7-bis(3-dibenzoborol-4-pyridylphenyl)-9,9'-spirobifluorene)

[0652] Add 2-(dibenzoborolylphenyl)-5-bromopyridine (2.6g, 6.5mmol), 2,7-bis(4,4,5, 5-Tetramethyl-1,3,2-dioxaborolanyl)-9,9'-spirobifluorene (1.5g, 2.7mmol), Pd(PtBu 3 ) 2 (170 mg, 0.32 mmol), and THF (65 mL) was added to the flask under a nitrogen atmosphere, followed by stirring.

[0653] A 2M tripotassium phosphate aqueous solution (11 mL, 22 mmol) was added thereto, and heated and stirred at 70° C. under reflux. After 12 hours, it was cooled to room temperature, the reaction solution was transferred to a separatory funnel, water was added, and ethyl acetate was used for extraction. The organic layer was washed with 3N hydrochloric acid, water, and saturated brine, and then dried with magnesium sulfate. The filtrate after filtration was concentrated, and the obtained solid was washed with methanol, thereby obtaining 2,7-bis(3-dibenzoborole-4-pyridylphenyl) in a yield of 47%. )-9,9'-spi...

Synthetic example 2

[0663] Under an argon atmosphere, ethyldiisopropylamine (39 mg, 0.30 mmol) was added to a dichloromethane solution (0.3 ml) containing 5-bromo-2-(4-bromophenyl) pyridine (94 mg, 0.30 mmol) , added boron tribromide (1.0M, 0.9ml, 0.9mmol) at 0°C, and stirred at room temperature for 9 hours. After cooling the reaction solution to 0° C., saturated potassium carbonate aqueous solution was added, and extraction was performed with chloroform. The organic layer was washed with brine, dried over magnesium sulfate and filtered. After concentrating the filtrate with a rotary evaporator, the resulting white solid was filtered out and washed with hexane to obtain a boron-containing compound 2 (40 mg, 0.082 mmol) represented by the following formula (50) in a yield of 28%. .

[0664] [chem 48]

[0665]

[0666] Its physical property values ​​are as follows.

[0667] 1 H-NMR (CDCl 3 ):7.57-7.59(m,2H),7.80(dd,J=8.4,0.6Hz,1H),7.99(s,1H),8.27(dd,J=8.4,2.1Hz,1H),9.01(d, J=1.5Hz,1H);

Synthetic example 3

[0669] Under a nitrogen atmosphere, the diethyl ether solution (1M, 61.2ml, 70.4mmol) of pentafluorophenylmagnesium bromide was cooled to 0°C, and a diethyl ether solution of zinc chloride (1M, 17ml, 17mmol). After completion of the dropwise addition, the mixture was stirred at room temperature for 1 hour. A toluene solution (80 ml) containing 5-bromo-2-(4-bromo-2-dibromoborylphenyl)pyridine (3.8 g, 8 mmol) represented by the above formula (26) was added thereto, at 80 ℃ heating and stirring for 15 hours. After cooling to room temperature, the reaction solution was added to ice water, and extracted with chloroform. The organic layer was washed with saturated brine, dried over sodium sulfate, and filtered. After concentrating the filtrate with a rotary evaporator, it was purified by silica gel chromatography (hexane:dichloromethane=1:1), thereby obtaining a boron-containing compound represented by the following formula (51) in a yield of 58%. 3 (2.2 g, 4.61 mmol).

[0670]...

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Abstract

The present invention (1) provides an organic-inorganic hybrid type organic electroluminescent element, even when a low-molecular compound layer is used as a layer constituting the organic electroluminescent element, crystallization of the low-molecular compound is suppressed, and light is emitted. excellent properties; (2) providing an organic-inorganic hybrid organic electroluminescent element having better luminous characteristics than existing organic-inorganic hybrid organic electroluminescent elements; and (3) providing an organic electroluminescent element, It is easy to manufacture, and is excellent in luminous efficiency and lifetime. The present invention relates to an organic electroluminescent element having a structure in which two or more layers are stacked, wherein the organic electroluminescent element is formed between a first electrode and a second electrode. There is a metal oxide layer between them, and a buffer layer made of an organic compound is placed on the metal oxide layer.

Description

technical field [0001] The invention relates to an organic electroluminescence element and a manufacturing method thereof. More specifically, the present invention relates to an organic electroluminescent element that can be used as a display device such as a display unit of an electronic device, a lighting device, and the like, and a method for manufacturing the same. Background technique [0002] Organic electroluminescence elements (organic EL elements) are expected as new light-emitting elements that can be applied to display devices and lighting. [0003] Organic electroluminescent elements are characterized by being thin, soft, and flexible, and when used as display devices, they have the ability to achieve high-brightness and high-resolution displays compared with liquid crystal display devices or plasma display devices that are currently mainstream. , Compared with liquid crystal display devices, it has excellent characteristics such as a wider viewing angle, so it ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): H01L51/50C09K11/06H05B33/10C07F5/02G09F9/30H01L27/32
CPCH10K85/151H10K85/322H10K50/16H10K2102/00H10K71/00
Inventor 深川弘彦清水贵央森井克行有元洋一
Owner NIPPON HOSO KYOKAI
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