Cyclic azine compound having nitrogen-containing fused aromatic group, method for producing same, and organic electroluminescent element using same as constituent component

一种环状吖嗪、化合物的技术，应用在高效率有机电致发光元件领域，能够解决没有记载化合物实施例等问题，达到驱动性及发光性优异、良好电荷注入及传输特性、寿命长的效果

Active Publication Date: 2014-09-10
TOSOH CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] 1,3,5-triazine derivatives are described in Patent Document 2, and compounds containing a 1,3,5-triazine ring and a nitrogen-containing aromatic group are also included in the derivatives, but details of the compounds are not described. Example

Method used

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  • Cyclic azine compound having nitrogen-containing fused aromatic group, method for producing same, and organic electroluminescent element using same as constituent component
  • Cyclic azine compound having nitrogen-containing fused aromatic group, method for producing same, and organic electroluminescent element using same as constituent component
  • Cyclic azine compound having nitrogen-containing fused aromatic group, method for producing same, and organic electroluminescent element using same as constituent component

Examples

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Embodiment

[0166] Hereinafter, examples and test examples are given to describe the present invention in more detail, but the present invention is not limited to these examples.

[0167] Reference example-1

[0168]

[0169] 3,5-Dibromobenzoyl chloride (5.97 g) and benzonitrile (4.12 g) were dissolved in chloroform (50 mL), and after cooling to 0° C., antimony pentachloride (5.98 g) was added dropwise. After the mixture was stirred at room temperature for 10 minutes, it was refluxed for 22 hours. After cooling the reaction mixture to room temperature, chloroform was distilled off under reduced pressure to obtain a yellow solid.

[0170] When the obtained yellow solid was added to 28% aqueous ammonia solution (300 mL) cooled to 0° C., a white solid was formed. After stirring at room temperature for 1 hour and filtering, the obtained white solid was washed with water and methanol. The resulting white solid was purified by silica gel column chromatography to obtain a white solid of 2-...

reference example -2

[0174]

[0175] Under argon flow, take 3,5-dibromobenzoyl chloride (29.8g) and p-toluonitrile (23.4g) in a 500mL three-port reaction vessel equipped with a reflux tube and a mechanical stirrer, add chlorobenzene (200mL) and dissolve . The obtained solution was cooled to 0° C., and antimony pentachloride (29.9 g) was added dropwise. The mixture was refluxed at room temperature for 1 hour, and further refluxed at 100°C for 2 hours. The resulting dark red suspension was cooled to -20°C and 28% aqueous ammonia solution (135 mL) was added. After stirring this milky white suspension at room temperature for 30 minutes, it heated slowly to 140 degreeC using an oil bath, and distilled off a solvent. Chlorobenzene (100 mL) was added, heated at 130° C., and filtered to remove insoluble matter. After cooling the filtrate naturally, methanol (100 mL) was added. The precipitated solid was filtered off, washed with methanol (30 mL×2) and dried to obtain the target product 2-(3,5-dibro...

Embodiment -1

[0207]

[0208] 2-Chloro-1,10-phenanthroline (4.26g), 2-[3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxo Borolan-2-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (4.67g), lithium chloride (1.06g) and tetrakis(triphenylphosphine)palladium ( 767mg) was suspended in a mixed solvent of toluene (200mL) and ethanol (50mL), 2.0M aqueous sodium carbonate solution (33.2mL) was added, and stirred at 100°C for 94 hours. After natural cooling, the low-boiling components were distilled off under reduced pressure, and the residue was purified by alumina column chromatography (developing solvent: hexane: chloroform = 1:2 to 0:1), and then recovered from a mixed solvent of dichloromethane and methanol. Crystallization, thus obtaining the target 2-[3,5-bis(1,10-phenanthrolin-2-yl)phenyl]-4,6-diphenyl-1,3,5-triazine white powder (yield 4.76g, yield 86%).

[0209] 1 H-NMR (CDCl 3 ): δ7.64-7.66 (m, 6H), 7.69 (dd, J = 4.3, 8.0Hz, 2H), 7.85 (d, J = 8.8Hz, 2H), 7.91 (d, J = 8.8Hz, 2H) , 8.31(dd, J=1.7, 8.0H...

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Abstract

A cyclic azine compound of formula (1): wherein, Y is C-H or a nitrogen atom, Ar 1 is a C 6-18 aromatic hydrocarbon group, which may be substituted with an C 1-4 alkyl group or a phenyl group, Ar 2 is a hydrogen atom, or a C 6-18 aromatic hydrocarbon group, which may be substituted with a phenyl group or a pyridyl group, or is a nitrogen-containing condensed ring C 9-15 aromatic group, Ar 3 is a nitrogen-containing condensed ring C 9-15 aromatic group, X is a phenylene group, and n is an integer in the range of 0-3. The cyclic azine compound is useful as a constituent of an organic electroluminescent device.

Description

technical field [0001] The invention relates to a cyclic azine compound with a nitrogen-containing condensed ring aromatic group and a production method thereof. [0002] The cyclic azine compound of the present invention has good charge transport properties and can form a stable thin film, so it is useful as a component of a fluorescent or phosphorescent organic electroluminescent device. The present invention also relates to a high-efficiency organic electroluminescent device having excellent drivability and luminescence, in which the cyclic azine compound is used in at least one of the organic compound layers of the organic electroluminescent device. Background technique [0003] An organic electroluminescent element has a structure in which a light-emitting layer containing a light-emitting material is sandwiched between a hole-transport layer and an electron-transport layer, and an anode and a cathode are installed on both sides of the sandwich structure. Organic elect...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/10C07D401/14C07D471/04C07D519/00C09K11/06H01L51/50C07B61/00
CPCC07D401/14H01L51/0069C07D519/00H01L51/0067C07D471/04C07D401/10H01L51/5072H10K85/656H10K85/654H10K50/16C07D251/24H10K85/6572H10K85/615
Inventor 相原秀典冈佑儿野村桂甫田中刚内田直树
Owner TOSOH CORP
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