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Organic compound, organic light-emitting device, and image display device

A technology of organic light-emitting devices and organic compounds, applied in the fields of organic semiconductor devices, organic chemistry, chemical instruments and methods, etc., can solve the problems of unsatisfactory development and achieve good sublimation and high luminous efficiency

Inactive Publication Date: 2013-09-18
CANON KK
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the development of such materials has not been satisfactory

Method used

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  • Organic compound, organic light-emitting device, and image display device
  • Organic compound, organic light-emitting device, and image display device
  • Organic compound, organic light-emitting device, and image display device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0109] The synthesis of exemplary compound XX-1

[0110]

[0111] (1) Synthesis of compound X3

[0112] The following reactants and solvent were placed in the reactor.

[0113] Compound X1: 4.0 g (13 mmol)

[0114] Compound X2: 2.8g (13mmol)

[0115] Ethanol: 65ml

[0116] Next, the reaction solution was heated to 60° C., and then 10 ml of a 6M aqueous sodium hydroxide solution was added dropwise to the solution. After the addition was complete, the reaction solution was heated to 80°C and stirred at this temperature (80°C) for 2 hours. Next, the reaction solution was cooled to generate a precipitate, which was then filtered off. Next, the obtained precipitate was sequentially washed with water and ethanol, and then dried by heating at 80° C. under reduced pressure to prepare 6 g of Compound X3 as a dark green solid (yield: 89%).

[0117] (2) Synthesis of compound X5

[0118] The following reactants and solvent were placed in the reactor.

[0119] Compound X3: 5.0 g...

Embodiment 2

[0137] The synthesis of exemplary compound XX-2

[0138]

[0139] (1) Synthesis of Compound X8

[0140] The following reactants and solvent were placed in the reactor.

[0141] Compound X7: 10g (55mmol)

[0142] Compound X2: 12g (55mmol)

[0143] Ethanol: 200ml

[0144] Next, the reaction solution was heated to 60° C., and then 20 ml of a 6M aqueous sodium hydroxide solution was added dropwise to the solution. After the addition was complete, the reaction solution was heated to 80°C and stirred at this temperature (80°C) for 2 hours. Next, the reaction solution was cooled to generate a precipitate, which was then filtered off. Next, the obtained precipitate was sequentially washed with water and ethanol, and then dried by heating at 80° C. under reduced pressure to prepare 18 g of Compound X8 as a dark green solid (yield: 92%).

[0145] (2) Synthesis of compound X9

[0146] The following reactants and solvent were placed in the reactor.

[0147] Compound X8: 10g (28...

Embodiment 3

[0165] The synthesis of exemplary compound XX-5

[0166] Exemplary compound XX-5 was prepared by synthesis according to the same method as in Example 2, except that in Example 2(1), Compound X11 shown below was used instead of Compound X2.

[0167]

[0168] As a result of measuring the purity of the obtained compound by HPLC, it was confirmed that the purity was 99.5% or more.

[0169] In addition, the toluene solution of the exemplary compound XX-5 (1×10 -5 mol / L) emission spectrum. In this embodiment, the excitation wavelength is 500 nm. As a result, an emission spectrum having a peak intensity at 550 nm was obtained.

[0170] Furthermore, the compound was identified by measuring the molecular weight using JMS-T100TD (DART-TOF-MASS) manufactured by JEOL, Ltd.

[0171] DART-TOF-MASS: M+H=805.3

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Abstract

The present invention provides an organic compound having a basic skeleton which has an emission wavelength in a yellow region, a high luminous efficiency, and good sublimability. An organic compound is shown in claim 1.

Description

technical field [0001] The present invention relates to an organic compound and an organic light emitting device and an image display device using the organic compound. Background technique [0002] Organic light emitting devices (organic EL devices) are electronic components each including a pair of electrodes and an organic compound layer disposed between the electrodes. Electrons and holes are injected from the electrode pair to generate excitons of the light-emitting organic compound in the organic compound layer, so that the organic light-emitting device emits light when the excitons return to the ground state. [0003] The recent development of organic light-emitting devices is remarkable, and its characteristics include low driving voltage, various emission wavelengths, high-speed response, and the ability to reduce the thickness and weight of the light-emitting device. [0004] In addition, light-emitting organic compounds have been actively developed so far. This ...

Claims

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Application Information

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IPC IPC(8): C07C13/62C09K11/06H01L51/50
CPCC07C13/62C07C211/61C09K11/06C09K2211/1011H05B33/14C07C2603/54H10K85/624H10K85/633H10K85/6572H10K50/11H10K2101/90H10K59/1213H10K85/626H10K85/654H10K85/6576
Inventor 桥本雅司镰谷淳堀内贵行宫下广和山田直树齐藤章人
Owner CANON KK
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