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1,3,5-triazine derivatives, preparation method thereof, and organic electroluminescent device using them as constituents

A technology of triazine derivatives and triazine rings, which is applied in the field of organic electroluminescent devices, and can solve problems such as not specifically shown and positions not limited

Active Publication Date: 2011-12-28
TOSOH CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In addition, although examples of using 1,3,5-triazine derivatives in organic electroluminescence devices have been disclosed (for example, refer to Patent Documents 5 and 6), benzene at positions 2, 4, and 6 of the triazine ring The position of the substituent on the base is not limited, and the 1,3,5-triazine derivative of the present invention characterized in having a quaternary aryl group containing a pyridyl group at the 2,4 position is not specifically shown
[0007] In addition, although examples of triazine derivatives having a quaternary aryl group containing a pyridyl group on the triazine ring for use in organic electroluminescence devices are disclosed (for example, refer to Patent Document 7), they are quaternary aryl groups The structure in which the end part of the triazine ring is bonded to the triazine ring is completely different from the 1,3,5-triazine derivative of the present invention
[0008] Furthermore, although examples of 1,3,5-triazine derivatives used in organic electroluminescence devices have been disclosed (for example, refer to Patent Document 8), they have 3,5-triazine derivatives at the 2-position of the triazine ring. Disubstituted phenyl triazine derivatives other than the 1,3,5-triazine derivatives of the present invention

Method used

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  • 1,3,5-triazine derivatives, preparation method thereof, and organic electroluminescent device using them as constituents
  • 1,3,5-triazine derivatives, preparation method thereof, and organic electroluminescent device using them as constituents
  • 1,3,5-triazine derivatives, preparation method thereof, and organic electroluminescent device using them as constituents

Examples

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Embodiment

[0109] The following examples and reference examples are given to illustrate the present invention in more detail, but the present invention is not limited by these examples.

[0110] Reference example-1

[0111]

[0112] Under argon, benzoyl chloride (4.93 g) and 5-chlorobiphenyl-3-carbonitrile (15.0 g) were added to a 300 mL three-necked reaction vessel equipped with a reflux tube, and chlorobenzene (100 mL) was added. The resulting solution was cooled to 0°C, and antimony pentachloride (10.5 g) was added dropwise. The mixture was stirred at room temperature for 20 minutes, and further refluxed at 100° C. for 2 hours. The resulting orange suspension was cooled to -20°C and 28% aqueous ammonia solution (50 mL) was added. After stirring the milky white suspension at room temperature overnight, it was slowly heated to 140° C. using an oil bath, and the organic solvent (65 mL) and water (33 mL) were distilled off. Chlorobenzene (100 mL) was added, heated and filtered at 13...

reference example -2

[0116]

[0117] Under argon, benzoyl chloride (1.23g) and 5-chloro-4'-methylbiphenyl-3-carbonitrile (4.00g) were added to a 200mL three-port reaction vessel equipped with a reflux tube, and chlorobenzene ( 40mL). The resulting solution was cooled to 0°C, and antimony pentachloride (2.63 g) was added dropwise. The mixture was stirred at room temperature for 20 minutes, and further refluxed at 100° C. for 2.5 hours. The resulting red solution was cooled to -20°C, and 28% aqueous ammonia solution (15 mL) was added. After stirring the milky white suspension at room temperature overnight, it was slowly heated to 140° C. using an oil bath, and the organic solvent (25 mL) and water (5 mL) were distilled off. Chlorobenzene (50 mL×2) was added, heated and filtered at 130°C. After cooling the filtrate naturally, methanol (100 mL) was added. The precipitated solid was collected by filtration, washed with methanol (30mL×2), and then dried to obtain 2,4-bis(3-chloro-4'-methylbipheny...

Embodiment -1

[0149]

[0150] Under argon flow, 4-(2-pyridyl)phenylboronic acid (2.25g), 2,4-bis(5-chlorobiphenyl-3-yl)-6-phenyl-1,3,5- Triazine (2.00g), cesium carbonate (3.68g), palladium acetate (33.9mg), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (143mg) in tetrahydrofuran (150mL ), and refluxed for 19 hours. After cooling the reaction mixture naturally, low-boiling point components were distilled off under reduced pressure, and methanol was added. The precipitated solid was collected by filtration and purified by silica gel column chromatography (developing solvent methanol:chloroform=1:100~1:75) to obtain the target product 6-phenyl-2,4-bis[4-(2-pyridyl) -1,1';3',1"-terphenyl-5'-yl]-1,3,5-triazine as white powder (yield 2.47 g, yield 85%).

[0151] 1 H-NMR (CDCl 3 ): δ7.26-7.30(m, 2H), 7.45(brt, J=7.3Hz, 2H), 7.53-7.64(m, 7H), 7.79-7.85(m, 8H), 7.93(d, J=8.4 Hz, 4H), 8.12(t, J=1.7Hz, 2H), 8.19(d, J=8.4Hz, 4H), 8.75(brd, J=5.0Hz, 2H), 8.84(brdd, J=7.5, 1.7 Hz, 2H), ...

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Abstract

A 1,3,5-triazine derivative represented by formula (1): wherein R 1 is hydrogen, C 1-4 alkyl group or substituted or unsubstituted phenyl group; n is an integer of 1-3, Ar is a substituted or unsubstituted aromatic hydrocarbon group, provided that Ar is different from two substituted quarterarylenyl groups bonded to the 1, 3 , 5-triazine ring; and V and Y are nitrogen or carbon, provided that a case where both of V and Y are carbon atoms is excluded. The organic electroluminescent device comprising the 1,3,5-triazine derivative as an electron transport material has a long lifetime.

Description

technical field [0001] The present invention relates to a 1,3,5-triazine derivative having a quaternary aryl group containing a pyridyl group, a method for preparing the same, and an electroluminescent device containing the same, which can be used as constituents of an organic electroluminescent device. [0002] The 1,3,5-triazine derivatives of the present invention can be used as constituents of organic electroluminescence devices due to their good charge transport properties. Therefore, the present invention further relates to an organic electroluminescent device having excellent drivability and durability using the 1,3,5-triazine derivative in at least one of the organic compound layers of the organic electroluminescent device. Background technique [0003] An organic electroluminescence device is a light-emitting layer containing a light-emitting material sandwiched between a hole-transport layer and an electron-transport layer, and an anode and a cathode are further in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C09K11/06H05B33/14H05B33/22
CPCC09K2211/1029C09K11/06C09K2211/1007C09K2211/1059H01L51/0067H05B33/10H01L51/5072C07D401/14H10K85/654H10K50/16C07D253/02
Inventor 相原秀典久松洋介田中刚宫下佑一新井信道内田直树饭田尚志
Owner TOSOH CORP
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