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Compound, organic thin-film light-emitting element, display device, and lighting device

A technology of light-emitting element and organic thin film, which is applied in the field of lighting devices to achieve the effect of excellent luminous efficiency and durable life

Pending Publication Date: 2022-07-12
TORAY IND INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still a lot of technical problems in the existing organic thin film light-emitting devices
Among them, the coexistence of high-efficiency light emission and long life of organic thin-film light-emitting devices has become a major issue.

Method used

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  • Compound, organic thin-film light-emitting element, display device, and lighting device
  • Compound, organic thin-film light-emitting element, display device, and lighting device
  • Compound, organic thin-film light-emitting element, display device, and lighting device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0140] Hereinafter, the present invention will be described with reference to Examples, but the present invention is not limited to these Examples.

Synthetic example 1

[0141] Synthesis Example 1: Synthesis of Compound 1

[0142] [Chemical 18]

[0143]

[0144] 2.7 g of 4'-(4-bromophenyl)-2,2':6'2"-terpyridine, 1.6 g of 4-(1-pyrene)phenylboronic acid, dichlorobis(triphenylphosphine palladium) The mixed solution of dichloride 50mg, 1.5M sodium carbonate aqueous solution 6ml and dimethoxyethane 70ml was heated and stirred for 5 hours under nitrogen flow and reflux. After cooling to room temperature, water was added and filtered, and methanol was used to clean, The obtained solid was purified by silica gel column chromatography, the solvent was evaporated and the solvent was removed, and the obtained solid was vacuum dried to obtain 2.3 g of Compound 1.

[0145] For the resulting compound 1, use an oil diffusion pump at 1 x 10 -3 It was used in an Example after carrying out sublimation refinement|purification at about 340 degreeC under the pressure of Pa. The high performance liquid chromatography (HPLC) purity (area % at measurement wavel...

Synthetic example 2

[0149] Synthesis Example 2: Synthesis of Compound 2

[0150] [Chemical 19]

[0151]

[0152] 4'-(4-bromophenyl)-2,2':6'2"-terpyridine 4.0 g, 3-chlorophenylboronic acid 1.7 g, dichlorobis(triphenylphosphine palladium) dichloride 72 mg The mixed solution of 10ml of 1.5M sodium carbonate aqueous solution and 70ml of dimethoxyethane was heated and stirred for 3 hours under nitrogen flow and reflux. After cooling to room temperature, water was added and filtered, washed with methanol, and vacuum-dried , 4.0 g of Intermediate A were obtained.

[0153] Next, a mixed solution of 2.9 g of intermediate A, 1.8 g of 1-pyrene boronic acid, 50 mg of dichlorobis(triphenylphosphine palladium) dichloride, 6 ml of a 1.5M aqueous solution of tripotassium phosphate and 40 ml of 1,4-dioxane was prepared. The mixture was heated and stirred under reflux for 7 hours under nitrogen flow. After cooling to room temperature, water was added, followed by filtration, washing with methanol, and vacuum...

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PUM

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Abstract

An organic thin-film light-emitting element having excellent luminous efficiency and durability life can be provided by the compound represented by general formula (1). (In general formula (1), any one of X1 to X3 is a nitrogen atom, and the other is a methine group. And L1 is a substituted or unsubstituted biphenylene group, a terphenyl group, a naphthylene group, a tetraphenylene group, a dimethyl fluorenylidene group, a diphenyl fluorenylidene group or a spirobifluorenylidene group. Wherein when these groups are substituted, substituent groups are alkyl groups or alkoxy groups. A is phenanthryl, pyrenyl, dimethyl fluorenyl, diphenyl fluorenyl or spirobifluorenyl. )

Description

technical field [0001] The present invention relates to a compound having a specific structure, an organic thin-film light-emitting element, a display device, and a lighting device using the compound. Background technique [0002] In recent years, organic thin-film light-emitting elements have been steadily put into practical use as displays for televisions and smartphones. However, there are still many technical problems in existing organic thin-film light-emitting devices. Among them, the coexistence of obtaining high-efficiency light emission and prolonging the life of the organic thin-film light-emitting element has become a major problem. [0003] As compounds for solving these problems, fluoranthene derivatives having a fluoranthene skeleton and an aromatic heterocyclic group containing electron-accepting nitrogen have been developed (for example, refer to Patent Document 1), and fluoranthene derivatives having a pyrene skeleton and an aryl or heterocyclic group have ...

Claims

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Application Information

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IPC IPC(8): C07D213/22H01L27/32H05B33/12H01L51/50
CPCH05B33/12C07D213/22H10K50/19H10K50/16H10K50/171C07D401/14H10K85/615H10K85/622H10K85/654
Inventor 徳田贵士长尾和真
Owner TORAY IND INC
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