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An electroluminescent element and organic technology, applied in electrical elements, luminescent materials, electro-solid devices, etc., can solve the problems of insufficient degree, low driving voltage luminous efficiency, etc.
Inactive Publication Date: 2019-09-10
HODOGOYA CHEMICAL CO LTD
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For elements using these compounds in the hole injection layer or hole transport layer, although heat resistance, luminous efficiency, etc. have been improved, the level is still not sufficient, and further lowering of the driving voltage and further improvement of the driving voltage are required. high luminous efficiency
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[0346] Hereinafter, an embodiment of the present invention will be specifically described by way of examples, but the present invention is not limited to the following examples.
Synthetic example 1
[0347]
[0348] Synthesis of bis(biphenyl-4-yl)-(6-phenylbiphenyl-3-yl)amine:
[0353] Furthermore, an aqueous solution obtained by dissolving 5.9 g of potassium carbonate in 36 mL of water beforehand was added to obtain a mixed liquid. Nitrogen gas was blown while irradiating the mixture with ultrasonic waves for 30 minutes.
[0354] Next, 0.74 g of tetrakis(triphenylphosphine)palladium was added, heated, and stirred at 72° C. for 18 hours. After cooling to room temperature, the organic layer was obtained by liquid separation. After washing with water and washing with saturated saline in this order, it was dried using anhydrous magnesium sulfate, and concentrated. A crude product is thus obtained. Next, purification using column chromatography was performed. As a result, 8.4 g of a white powder of c...
Synthetic example 2
[0361]
[0362] Synthesis of bis(biphenyl-4-yl)-{6-(naphthyl-1-yl)biphenyl-3-yl}amine:
[0363] In Synthesis Example 1, 1-naphthylboronic acid was used instead of phenylboronic acid, and the reaction was carried out under the same conditions. As a result, 9.2 g of white powder of compound 1-3 was obtained (61% yield).
[0364] [chem 21]
[0365]
[0366] For the obtained white powder, its NMR was used to identify the structure. use 1 H-NMR (CDCl 3 ) detected the following 33 hydrogen signals.
[0367] δ(ppm)=7.84-7.87(3H)
[0368] 7.67-7.83(6H)
[0369] 7.26-7.64(18H)
[0370] 7.02-7.04(6H)
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Abstract
The purpose of the present invention is to provide an organic EL element which (1) has high luminous efficiency and high power efficiency, (2) has a low light emission start voltage, (3) has a low practical driving voltage, and (4) particularly has a long service life. According to the present invention, an organic electroluminescent (EL) element is provided, which is provided with at least a positive electrode, a hole injection layer, a first hole transport layer, a second hole transport layer, a light-emitting layer, an electron transport layer and a negative electrode in this order and is characterized in that the second hole transport layer contains an arylamine compound represented by general formula (1) and the electron transport layer contains a pyrimidine derivative represented bygeneral formula (2). In general formula (2), A represents a monovalent group represented by structural formula (3).
Description
technical field [0001] The present invention relates to an organic electroluminescent device, and more specifically, to an organic electroluminescent device (hereinafter simply referred to as an organic EL device) using a specific arylamine compound and a specific pyrimidine derivative. Background technique [0002] Since the organic EL element is a self-luminous element, it is brighter than a liquid crystal element, has excellent visibility, and can perform a clear display. Therefore, active research has been conducted on organic EL elements. [0003] In 1987, C.W.Tang et al. of Eastman Kodak successfully developed a practical organic EL device by creating a laminated structure in which various functions for light emission are distributed to each material. This organic EL element is constituted by laminating a phosphor capable of transporting electrons and an organic material capable of transporting holes, injecting positive charges and negative charges into the layer of t...
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