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Organic light emitting element, display device, image information processing device, lighting device, image forming device, exposure device, and organic photoelectric conversion element

a light-emitting element and organic technology, applied in the field of organic light-emitting elements, can solve the problems of easy oxidation, low stability of compounds in the air, unstable compounds, etc., and achieve the effect of high stability against oxidation

Inactive Publication Date: 2017-01-12
CANON KK
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patent describes an organic light emitting element that has a high stability against oxidation in the air and is not easily transformed in the air. The element contains an organic compound that has a specific formula and a pair of electrodes. The organic compound is derived from an aromatic hydrocarbon group or a heteroaromatic ring group and has specific characteristics such as carbon atoms, hydrogen atoms, halogens, cyano groups, and more. The patent also mentions that the element can have a benzene ring with specific substituents, such as halogens, cyano groups, and so on. The patent also highlights that the element can have sulfur or oxygen atoms as well. The technical effect of this patent is to provide an organic light emitting element that has a stable structure and is resistant to damage by oxidation.

Problems solved by technology

However, all those compounds are unstable, that is, for example, 1-A is easily oxidized in the air, and the structure of 1-B is easily transformed at room temperature.
Although the organic compounds disclosed in Non-Patent Literatures 1 and 2 have a high electron injection property, the reactivity thereof with moisture is high, and hence, those compounds have a low stability in the air.

Method used

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  • Organic light emitting element, display device, image information processing device, lighting device, image forming device, exposure device, and organic photoelectric conversion element
  • Organic light emitting element, display device, image information processing device, lighting device, image forming device, exposure device, and organic photoelectric conversion element
  • Organic light emitting element, display device, image information processing device, lighting device, image forming device, exposure device, and organic photoelectric conversion element

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of Example Compound A1

[0187]

(1) Synthesis of Compound D3

[0188]The following reagent and solvents were charged into a 50-ml eggplant flask.

D1: 3.00 g (16.9 mmol)

DMSO: 10 ml

[0189]20 N NaOH aqueous solution: 0.8 ml

[0190]Next, the reaction solution was cooled to 0° C. while being stirred in a nitrogen atmosphere. Subsequently, 1.0 ml (16.9 mmol) of carbon disulfide was slowly dripped and was then stirred at 0° C. for 30 minutes. Next, stirring was performed at room temperature for 1 hour. The solution was again cooled to 0° C., and 1.7 ml (16.9 mmol) of D2 was slowly dripped and was then stirred at 0° C. for 30 minutes. Subsequently, stirring was performed at room temperature for 1 hour. After the reaction was completed, water was added to the reaction solution and then stirred, and filtration thereof was performed using a membrane filter, so that a residue was obtained. After the residue thus obtained was dissolved in 20 ml of ethanol, 0.85 ml of a conc. hydrochloric acid was...

example compound a1

(3) Synthesis of Example Compound A1

[0193]The following reagent and solvent were charged into a 50-ml eggplant flask in a nitrogen flow atmosphere.

D4: 470 mg (1.30 mmol)

Dehydrated DMF: 10 ml

[0194]After this solution was deaerated using nitrogen, 187 mg (3.90 mmol) of sodium hydride (oil dispersion at 50% to 60%) was charged thereto, and stirring was then performed for 2 minutes. Subsequently, 145 mg (1.30 mmol) of potassium tert-butoxide was added, and stirring was performed at room temperature for 6 hours. After the reaction was completed, while stirring was performed, 30 ml of water which was deaerated using nitrogen was slowly added to precipitate a target product, and the solvent was then removed using a syringe. Next, after the operation of adding 20 ml of water deaerated using nitrogen and removing the solvent using a syringe was again performed twice, 10 ml of hexane deaerated using nitrogen was added, and dispersion washing was performed by an ultrasonic washing machine. Sub...

example 2

Synthesis of Example Compound A5

[0198]In Example 1(1), except that the compound D5 shown below was used instead of the compound D1, the example compound A5 was obtained by a method similar to that of Example 1.

[0199]The identification result of the compound thus obtained is shown below.

[MALDI-TOF-MS]

[0200]Measured value: m / z=602.88, calculated value: C38H54N2S2=602.98 [CV measurement]

First Oxidation Potential: −1.05 V

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Abstract

The present disclosure provides an organic light emitting element which has a pair of electrodes and an organic compound layer disposed therebetween and in which the organic compound layer contains an organic compound represented by the following general formula [1],wherein in the formula [1], Ar1 and Ar2 each independently represent an aromatic hydrocarbon group or a heteroaromatic ring group, R1 to R4 are each independently selected from a hydrogen atom or a substituent, R1 and R2 and R3 and R4 each may form a benzene ring, wherein the benzene ring may have at least one substituent.

Description

BACKGROUND[0001]Field of the Disclosure[0002]The present disclosure relates to an organic light emitting element, a display device, an image information processing device, a lighting device, an image forming device, an exposure device, and an organic photoelectric conversion element.[0003]Description of the Related Art[0004]An organic light emitting element is an electronic element having an anode, a cathode, and an organic compound layer disposed between the two electrodes. In the organic light emitting element, since positive holes (holes) and electrons injected from the respective electrodes are recombined in the organic compound layer, excitons are generated, and light is emitted when the excitons are returned to the ground state. Recent development of organic light emitting elements has been remarkably carried out, and a thin and lightweight light emitting device having a low drive voltage, various light emission wavelengths, and a high responsivity can be realized.[0005]Howeve...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): H01L51/00C07D263/32H04N5/225C07D263/56H04N5/378C07D277/22C07D277/64H10K99/00
CPCH01L51/0069H01L27/307C07D263/32H01L51/0071C07D277/64C07D263/56H04N5/378H04N5/2253H01L51/5206H01L51/5221H01L51/5092H01L51/504H01L27/3262H01L27/1225H01L51/529H01L27/3234H01L51/441H01L51/4253C07D277/22H10K85/656H10K85/657H10K50/171H10K59/65H10K39/32H10K59/1213
Inventor MIYASHITA, HIROKAZUKAMATANI, JUN
Owner CANON KK