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Naphthacene derivative and organic electroluminescent device using the same

A derivative, tetracene technology, applied in the field of organic electroluminescent elements, can solve the problems of no practical efficiency, and achieve the effect of prolonging life, long life and excellent color purity

Inactive Publication Date: 2009-03-25
IDEMITSU KOSAN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] Patent Document 11 discloses a device formed by using naphthacene derivatives and indenoperylene derivatives in the light-emitting layer, and using naphthacene derivatives in the electron transport layer, but there is no practical efficiency.

Method used

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  • Naphthacene derivative and organic electroluminescent device using the same
  • Naphthacene derivative and organic electroluminescent device using the same
  • Naphthacene derivative and organic electroluminescent device using the same

Examples

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Embodiment

[0231] Hereinafter, the present invention will be further specifically described by way of examples, but the present invention is not limited to these examples.

Synthetic example 1

[0233] Synthesis of Compounds A-1 and A-2

[0234]

[0235] (1) Synthesis of Intermediate (A-1a)

[0236] 5.5 g of 2,4,6-triphenyliodobenzene was dissolved in 40 ml of toluene, 13 ml of diethyl ether was added, the mixture was cooled to -55°C, and 8 ml of a 1.6 M n-butyllithium / n-hexane solution was added, followed by stirring for 1 hour. To this, 2.6 g of 5,12-butanone was added as a powder, and the reaction was allowed to proceed for 3 hours while gradually raising the temperature to 0°C. The reaction was stopped by adding 20 ml of methanol, and the resulting solid was filtered off and washed with methanol. This was purified by silica gel column chromatography to obtain 5.7 g (yield 99%) of a pale yellow powder of the target intermediate (A-1a).

[0237] (2) Synthesis of Intermediate (A-1b)

[0238] 2.8 g of the intermediate (A-1a) was dissolved in 30 ml of tetrahydrofuran, and 15 ml of a 1M phenylmagnesium bromide / tetrahydrofuran solution was added dropwise over 10 mi...

Synthetic example 2

[0246] Synthesis of Compound A-3

[0247]

[0248] (1) Synthesis of Intermediate (A-3b)

[0249] 7.4 g of 2,4-diphenyliodobenzene was dissolved in 45 ml of toluene, 15 ml of diethyl ether was added, the mixture was cooled to -55°C, and 13 ml of a 1.6 M n-butyllithium / n-hexane solution was added, followed by stirring for 1 hour. To this, 1.9 g of 5,11-butanone was added in the form of powder, and the reaction was carried out for 3 hours while gradually raising the temperature to 0°C. 20 ml of methanol was added to stop the reaction, and the resulting solid was filtered off and washed with methanol. After washing with toluene under heating under reflux, vacuum drying was performed to obtain 3.3 g (yield: 60%) of a pale yellow powder of the target intermediate (A-3b).

[0250] (2) Synthesis of compound A-3

[0251] Under light shielding, 80 ml of tetrahydrofuran was added to 3.3 g of the intermediate (A-3b), and the mixture was heated to about 40° C. to dissolve. A solutio...

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Abstract

A material for an organic EL device conatining a novel naphthacene derivative; a luminescent material containing a novel naphthacene derivative; and an organic electroluminescent device including one or more organic layers interposed between a cathode and an anode, and at least one layer of the organic layers containing a naphthacene derivative represented by the following formula (1) or (2).

Description

technical field [0001] The present invention relates to a novel naphthacene derivative, a material for an organic electroluminescence (EL) device using the derivative, and an organic electroluminescence device containing the same. Background technique [0002] The organic EL element is a spontaneous light-emitting element whose principle is that when an electric field is applied, a fluorescent substance emits light by the recombination energy of holes injected from the anode and electrons injected from the cathode. [0003] Since C.W.Tang et al. (Non-Patent Document 1) of Esteman Co., Ltd. reported a low-voltage driven organic EL element of a laminate type element, there has been a research on organic EL elements using organic materials as structural materials. The research on components is in the ascendant. [0004] Tang et al. adopted a laminated structure in which tris(8-quinolinolato)aluminum (Alq) was used for the light-emitting layer and a triphenyldiamine derivative ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C15/38H01L51/50C09K11/06
CPCC09K2211/1011C07C15/38H05B33/14C09K11/06H01L51/0071H01L51/0054C07C2103/44H01L51/0072C07D235/08C07C2603/44H10K85/622H10K85/657H10K85/6572H10K85/615
Inventor 荒金崇士池田洁山本弘志佐土贵康细川地潮
Owner IDEMITSU KOSAN CO LTD
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