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Organic electroluminescence element

An electroluminescent element and luminescent technology, applied in electrical components, organic semiconductor devices, organic chemistry, etc., can solve problems that cannot be said to be sufficient, and achieve the effects of long life, high luminous efficiency, and low driving voltage

Active Publication Date: 2018-08-31
NIPPON STEEL CHEM &MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0022] However, none of them can be said to be sufficient, and further improvements are expected.

Method used

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  • Organic electroluminescence element
  • Organic electroluminescence element
  • Organic electroluminescence element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0111] Hereinafter, although an Example demonstrates this invention in more detail, this invention is not limited to these Examples.

[0112] Compounds used in Examples are shown below. It should be noted that compounds 1-17, 1-24, 1-36, 2-4, 2-12, 2-15, 2-20 and 2-37 are the above-mentioned compounds.

[0113]

Synthetic example 1

[0115]

[0116] Under a nitrogen atmosphere, 0.95 g of NaH and 10 ml of DMF were added and stirred at room temperature. Then, 7.13 g of the intermediate (A) dissolved in 100 ml of DMF was added and stirred at room temperature for 30 minutes. Furthermore, 6.58 g of 2,6-difluorobenzonitrile was added, and it stirred at room temperature for 6 hours. 500 ml of water was added to the reaction solution, the mixture was stirred at room temperature for 1 hour, and the precipitated solid was filtered off. The obtained solid was purified by silica gel column chromatography to obtain 7.81 g of an intermediate (B) (yield 80%).

[0117] Under a nitrogen atmosphere, 1.00 g of NaH and 10 ml of DMF were added and stirred at room temperature. Then, 3.47 g of carbazole dissolved in 100 ml of DMF was added and stirred at room temperature for 30 minutes. Furthermore, 7.81 g of 2 intermediates (B) were added, and it stirred at room temperature for 1 hour. 200 ml of water was added to the re...

Synthetic example 2

[0120]

[0121] Under a nitrogen atmosphere, 3.44 g of NaH and 10 ml of DMF were added and stirred at room temperature. Then, 11.90 g of carbazole dissolved in 50 ml of DMF was added and stirred at room temperature for 30 minutes. Furthermore, 19.81 g of 2,6-difluorobenzonitrile was added, and it stirred at room temperature for 3 hours. 200 ml of water was added to the reaction solution, the mixture was stirred at room temperature for 1 hour, and the precipitated solid was filtered off. The obtained solid was purified by silica gel column chromatography and recrystallization to obtain 12.76 g of an intermediate (C) (yield 62%).

[0122] Under a nitrogen atmosphere, 4.30 g of NaH and 10 ml of DMF were added and stirred at room temperature. Then, 12.59 g of the intermediate (D) dissolved in 50 ml of DMF was added and stirred at room temperature for 30 minutes. Further, 12.76 g of the intermediate (C) dissolved in 50 ml of DMF was added, and the mixture was stirred at room ...

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Abstract

Provided is a heat-activated delayed-fluorescence organic electroluminescence element that has a low drive voltage, high luminous efficiency, and long life. An organic electroluminescence element thatincludes a luminescent layer between a positive electrode and a negative electrode that face. The organic electroluminescence element contains, in at least one luminescent layer, a heat-activated delayed-fluorescence material or a heat-activated delayed-fluorescence material and a host material. The heat-activated delayed-fluorescence material is represented by general formula (1), wherein A is an electron-withdrawing group such as a CN group and D1 and D2 are electron-donating groups that have an indole-ring structure.

Description

technical field [0001] The present invention relates to an organic electroluminescent element (referred to as an organic EL element). Background technique [0002] By applying a voltage to the organic EL element, holes are injected from the anode into the light emitting layer, and electrons are injected from the cathode into the light emitting layer. Then, in the light-emitting layer, the injected holes and electrons recombine to generate excitons. At this time, singlet excitons and triplet excitons are generated at a ratio of 1:3 according to the statistical law of electron spin. For a fluorescent organic EL device that utilizes light emission from singlet excitons, it can be said that an internal quantum efficiency of 25% is the limit. On the other hand, it is known that the internal quantum efficiency can be increased to 100% when singlet excitons efficiently perform intersystem crossing in a phosphorescent organic EL device utilizing emission by triplet excitons. [0...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01L51/50C07D487/04C07D519/00C09K11/06
CPCC07D487/04C07D519/00C09K11/06H10K85/6572H10K50/11H10K2101/90H10K2101/20C09K2211/1029H10K50/00C09K2211/1018
Inventor 多田匡志吉村和明川田敦志野口胜秀相良雄太小川淳也
Owner NIPPON STEEL CHEM &MATERIAL CO LTD
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