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Organic electroluminescent element

An electroluminescence element and an electroluminescence technology, which are applied in the directions of electroluminescence light sources, electrical components, electric light sources, etc., and can solve the problems of undisclosed compounds and the like

Active Publication Date: 2012-10-24
NIPPON STEEL CHEM &MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0021] However, the above-mentioned compound is a compound in which an aromatic heterocycle is directly substituted on the nitrogen of the indolocarbazole skeleton, and a compound in which an aromatic hydrocarbon is used as a linking group is not disclosed.

Method used

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Examples

Experimental program
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Effect test

Embodiment

[0118] Hereinafter, the present invention will be described in more detail using examples. Of course, the present invention is not limited to these examples, and can be implemented in various forms as long as the gist thereof is not exceeded.

[0119] The indolocarbazole compound used in the present invention was synthesized according to the scheme shown below. In addition, the compound number corresponds to the number attached to the above-mentioned chemical formula.

Synthetic example 1

[0121] Synthesis of Compound 3-1

[0122]

[0123] Under a nitrogen atmosphere, 10.0 g (0.039 moles) of 5,12-dihydroindolo[3,2-a]carbazole (IC-1), 39.8 g (0.20 moles) of iodobenzene, and 6.2 g (0.098 moles) of copper were added. mol), 8.1 g (0.059 mol) of potassium carbonate, and 200 ml of tetraethylene glycol dimethyl ether were stirred. Then, it heated to 190 degreeC, and stirred for 24 hours. After cooling the reaction solution to room temperature, copper and inorganic substances were collected by filtration. 200 ml of water was added to the filtrate, stirred, and the precipitated crystals were collected by filtration. After drying this under reduced pressure, it was purified by column chromatography to obtain 9.7 g (0.029 mol, yield: 75%) of Intermediate A as a white powder.

[0124] Under a nitrogen atmosphere, 25.0 g (0.075 moles) of intermediate A, 25.6 g (0.066 moles) of 4-(3-bromophenyl)-2,6-diphenylpyridine, and 25.5 g (0.13 moles) of copper iodide were added ...

Synthetic example 2

[0127] Synthesis of Compound 3-13

[0128]

[0129] Under a nitrogen atmosphere, add IC-19.9g (0.039 mol), 4-(3-bromophenyl)-2,6-diphenylpyridine 14.6g (0.038 mol), copper iodide 13.5g (0.071 mol), 16.6 g (0.12 mol) of potassium carbonate and 350 ml of 1,3-dimethyl-2-imidazolidinone were stirred at 185° C. for 30 hours. After cooling the reaction solution to room temperature, inorganic substances were collected by filtration. The obtained filtrate was added to 4000 ml of water, stirred, and the precipitated crystal was collected by filtration. After drying under reduced pressure, it was purified by column chromatography to obtain 20.5 g (0.036 mol, yield: 94%) of Intermediate B as a white powder.

[0130] Under a nitrogen atmosphere, 19.1 g (0.034 mol) of intermediate B, 12.9 g (0.034 mol) of 4-(3-bromophenyl)-2,6-diphenylpyridine, and 12.2 g (0.064 mol) of copper iodide were added , 15.8 g (0.12 mol) of potassium carbonate, and 300 ml of 1,3-dimethyl-2-imidazolidinone w...

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Abstract

Disclosed is an organic electroluminescent element (organic EL element) that has improved light-emitting efficiency of the element, sufficiently secures driving stability, and has a simple configuration. In this organic EL element, an anode, an organic layer containing a phosphorescent light-emitting layer, and a cathode are layered on a substrate, and an indolocarbazole compouond represented by general formula 1 is contained within at least one organic layer selected from a light-emitting layer, an electron transport layer, and a hole-blocking layer. When the indolocarbazole compound is contained in the light-emitting layer, which containins a phosphorescent light-emitting dopant and a host material, the indolocarbazole compound is contained as the host material. The compound represented by the belowmentioned formula (2) exists as an indolocarbazole compound. A1 and A2 represent an aromatic hydrocarbon group; B1 and B2 represent an aromatic heterocycle group; R1 through R3 represent hydrogen, an alkyl group, a cycloalkyl group, an aromatic hydrocarbon group, or an aromatic heterocycle group; m represents an integer from 1 to 3; and n represents an integer from 0 to 3.

Description

technical field [0001] The present invention relates to an organic electroluminescent device containing an indolocarbazole compound, and more specifically, to a thin-film device that emits light by applying an electric field to a light-emitting layer formed of an organic compound. Background technique [0002] In general, an organic electroluminescence element (hereinafter referred to as an organic EL element) has a light emitting layer and a pair of counter electrodes sandwiching the layer as its simplest structure. That is, in an organic EL element, when an electric field is applied between two electrodes, electrons are injected from the cathode and holes are injected from the anode, and these recombine in the light-emitting layer to emit light. [0003] In recent years, the development of organic EL elements using organic thin films has continued. In particular, in order to improve the luminous efficiency and improve the efficiency of injecting carriers from the electrod...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01L51/50C09K11/06C07D487/04H10K99/00
CPCC07D471/14H05B33/14C07D487/14H01L51/0074H01L51/5096C09K2211/1044H01L51/0085C07D519/00H01L51/5048H01L51/0072C07D487/04H01L51/0067H01L51/5012C09K11/06H10K85/654H10K85/6576H10K85/6572H10K85/342H10K50/14H10K50/18H10K50/11H10K2101/10
Inventor 甲斐孝弘古森正树山本敏浩松本惠
Owner NIPPON STEEL CHEM &MATERIAL CO LTD
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