Organic electroluminescent device comprising triazine derivatives

An electroluminescent device, organic technology, applied in the direction of electric solid-state devices, organic chemistry, luminescent materials, etc., can solve the problems of not being able to vapor phase deposition, not being disclosed, etc.

Inactive Publication Date: 2011-05-25
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

QUR 3 Since then it has often been used as an electron transport material, but it has many disadvantages: since it partially decomposes at the sublimation temperature, it cannot be vapor-deposited without leaving a residue, which is a major problem, especially in terms of production equipment especially For production equipment
However, the application does not disclose that these materials are also suitable as electron transport materials for fluorescent electroluminescent devices

Method used

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  • Organic electroluminescent device comprising triazine derivatives
  • Organic electroluminescent device comprising triazine derivatives
  • Organic electroluminescent device comprising triazine derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0152] Example 1: Synthesis of 2-(4,6-bis[3,1'; 5,1"]terphenyl-1-yl)-1,3,5-triazin-2-yl)-spiro-9, 9'-bifluorene

[0153]

[0154] a) Synthesis of 2-chloro-(4,6-bis[3,1′; 5,1″]terphenyl-1-yl)-1,3,5-triazine

[0155] 82.6 ml of a 2.0 molar solution of n-butyllithium in hexane was slowly added dropwise to 50.30 g (163 mmol) of 1-bromo-[3,1′;5,1″]terphenyl cooled to -78°C -1-yl in a solution of 400ml of anhydrous tetrahydrofuran, and the mixture was stirred for 15 minutes.The reaction solution was slowly added dropwise to 10.00g (45mmol) of cyanuric chloride cooled to -78°C in 400ml of anhydrous tetrahydrofuran in solution, and the cooling was removed. When RT had been reached, the precipitated product was filtered off. The yield was 21.08 g (37 mmol), corresponding to 67.9% of theory.

[0156] b) Synthesis of 2-(4,6-bis[3,1′; 5,1″]terphenyl-1-yl)-1,3,5-triazin-2-yl)spiro-9,9′- Bifluorene

[0157] 17.46g (48mmol) of spiro-9,9'-difluorene-2-boronic acid, 21.06g (37mmol) of 2...

Embodiment 2

[0158] Example 2: Synthesis of 2-(4,6-bis(3-([3,1′; 5,1″]terphenyl-1-yl)phen-1-yl)-1,3,5-triazine -2-yl)spiro-9,9'-bifluorene

[0159]

[0160] a) Synthesis of 1-bromo-3-([3,1′; 5,1″]terphenyl-1-yl)phenyl

[0161] Suspend 40.0 g (146 mmol) of 3-boroncarbonyl-[3,1′;5,1″] terphenyl, 18.8 g (146 mmol) of 1-iodo-3-bromobenzene and 109.3 g (730 mmol) of potassium carbonate In 1350ml toluene and 1150ml water.Add 844mg (0.73mmol) tetrakis (triphenylphosphine) palladium (0) in this suspension, and this reaction mixture is heated under reflux 16h.After cooling, the organic phase is separated , washed three times with 200 ml of water, dried over sodium sulfate and then evaporated to dryness. The residue was washed with ethanol, recrystallized from ethyl acetate and finally dried under reduced pressure. The yield was 47.6 g (123 mmol), corresponding to theoretical 84.5%.

[0162] b) Synthesis of 2-chloro-4,6-bis(3-([3,1′;5,1″]terphenyl-1-yl)phen-1-yl)-1,3,5-triazine

[0163] The s...

Embodiment 3

[0166] Example 3: Synthesis of 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-2′,7′-bis([3,1′; 5,1″]- Terphenyl-1-yl)spiro-9,9'-bifluorene

[0167]

[0168] a) Synthesis of 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-2',7'-dibromospiro-9,9'-difluorene

[0169] 47.90g (89mmol) of 2-chlorocarbonyl-2',7'-dibromospiro-9,9'-difluorene, 11.90g (89mmol) of aluminum trichloride and 1.9ml (27mmol) of thionyl Dichloride was suspended in 260ml of dichlorobenzene in a flask. Then 19.3 ml (187 mmol) of benzonitrile were slowly added. The reaction mixture was stirred at 100 °C for 1 h. 9.55 g (179 mmol) of ammonium chloride were added and the batch was stirred at 100° C. for 16 h. After cooling to RT, the reaction solution was added to 3.5 L of methanol, and the mixture was stirred for 45 min. The precipitated solid was filtered off and recrystallized from toluene. Yield 18.8 g (26.7 mmol), corresponding to 2 g.8% of theory.

[0170] b) Synthesis of 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-2′,7′-bis([3,1...

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Abstract

The present invention relates to organic electroluminescent devices which comprise triazine derivatives as the electron transport material.

Description

technical field [0001] The present invention relates to organic electroluminescent devices comprising triazine derivatives as electron transport materials. Background technique [0002] The structure of organic electroluminescent devices (OLEDs) in which organic semiconductors are used as functional materials is described, for example, in US 4539507, US 5151629, EP 0676461 and WO 98 / 27136. However, further improvements are still required. Therefore, there is still a need for improvement, especially in terms of lifetime, efficiency and operating voltage of organic electroluminescent devices. Furthermore, the compounds must have high thermal stability and a high glass transition temperature and must be able to sublimate without decomposition. [0003] Improvements in properties are still desired, especially in the case of electron-transport materials, since in addition the properties of electron-transport materials have an important influence on the aforementioned properties...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01L51/50
CPCH01L51/002H01L51/0054H01L51/5052H01L51/0067H01L51/0056H01L51/0055H01L51/0058H10K71/30H10K85/623H10K85/622H10K85/624H10K85/626H10K85/654H10K50/165H10K85/30H10K85/615H10K50/16
Inventor 克里斯托夫·普夫卢姆西莫内·洛伊约阿希姆·凯泽埃米尔·侯赛因·帕勒姆弗兰克·福格斯乔纳斯·瓦伦丁·克罗巴阿尔内·比辛
Owner MERCK PATENT GMBH
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