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Compounds and organic electroluminescent devices

A technology for electroluminescent devices and compounds, which can be used in electroluminescent light sources, electro-solid devices, preparation of amino compounds, etc., and can solve problems such as high working voltage and poor performance data.

Active Publication Date: 2015-04-01
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In practice, higher layer thicknesses for the hole transport layer are often desired, however this often results in higher operating voltages and poorer performance data

Method used

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  • Compounds and organic electroluminescent devices
  • Compounds and organic electroluminescent devices
  • Compounds and organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0307] Synthesis of compound biphenyl-2-yl-biphenyl-4-yl-(9-methyl-9-p-tolyl-9H-fluoren-2-yl)-amine (1-1) and compound (1-2) to (1-11)

[0308]

[0309] Among them, Toluene is toluene, and Buchwald-Hartwig coupling is Buchwald-Hartwig coupling.

[0310] 2-Bromo-9-methyl-9-p-tolyl-9H-fluorene

[0311] 40 g (154 mmol) of 2-bromo-9H-fluorene were dissolved in 500 mL of dry THF in a thoroughly heated flask. solution in N 2 Saturated and 15.0 g (170 mmol) of cerium(III) chloride were added. The clear solution was cooled to -10°C and then 121 mL (170 mmol) of 1.4M methylmagnesium bromide solution was added. The reaction mixture was slowly warmed to room temperature, and then washed with NH 4 Quenched with Cl (500 mL). The mixture was then partitioned between acetate and water, the organic phase was washed three times with water, and the 2 SO 4 Dry and rotovap. To the rotovaped solution was added 60 mL of toluene. The precipitate was heated to 50°C and then 27.2 mL of tr...

example 2

[0323] The synthetic compound biphenyl-4-yl-(9,9-dimethyl-9H-fluoren-2-yl)-(9-methyl-9-phenyl-9H-fluoren-4-yl)-amine (2 -1) and compounds (2-2) to (2-8)

[0324]

[0325] Among them, Aminierung means amination

[0326] 4-Bromo-9-methyl-9-phenyl-9H-fluorene

[0327] Dissolve 30 g (94 mmol) of 2,2'-dibromobiphenyl in 200 mL of dry THF in a thoroughly heated flask. The reaction mixture was cooled to -78°C. At this temperature 37.7 mL of a 2.5M solution of n-butyllithium in hexane (94 mmol) were slowly added dropwise (duration: about 1 hour). The precipitate was stirred at -70°C for 1 hour. Then 11.1 mL of acetophenone (94 mmol) was dissolved in 100 ml of THF and added dropwise at -70°C. After the addition was complete, the reaction mixture was slowly warmed to room temperature and washed with NH 4 Cl quenched and then concentrated on a rotary evaporator. To the rotovaped solution was carefully added 300 mL of acetic acid and then 50 mL of fuming hydrochloric acid. The ...

example 3

[0337] Synthetic compound biphenyl-4-yl-biphenyl-2-yl-(7,9-diphenyl-9-p-tolyl-9H-fluorene-2-yl)-amine (3-1) and compound (3 -2) to (3-4)

[0338]

[0339] Among them, Aminierung means amination, Kupplung means coupling, and Toluen means toluene.

[0340] 2-Bromo-7-phenylfluoren-9-one

[0341]21.6 g (178 mmol) of phenylboronic acid, 60 g (178 mmol) of 2,7-dibromo-fluorene were suspended in 800 mL of dimethoxyethane and 265 mL (533 mmol) of 2M sodium carbonate solution. 6.154 g (5 mmol) of tetrakis(triphenylphosphine) were added to the suspension, and the reaction mixture was heated to reflux for 18 hours. After the reaction mixture had cooled, the organic phase was separated, filtered on silica gel, washed 3 times with 100 mL of water and then concentrated to dryness. 38.6 g (85%) of 2-bromo-7-phenylfluoren-9-one were obtained after filtration of the crude product on silica gel through toluene.

[0342] The following brominated compounds were prepared analogously thereto...

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Abstract

The present invention concerns particular fluorenes, the use of the compound in an electronic device, and an electronic device containing at least one of these compounds. The present invention further concerns a method for producing the compound and a formulation and composition containing one or more of the compounds.

Description

technical field [0001] The present invention relates to a novel organic compound, the use of a compound in an organic electroluminescent device and an organic electroluminescent device comprising at least one of said compounds. Furthermore, the invention relates to a process for the preparation of said compounds as well as to compositions and formulations containing at least one of said compounds. Background technique [0002] The development of functional compounds for electroluminescent devices is currently the subject of intensive research. The aim here is in particular to develop compounds by which improved properties of the electroluminescent device can be achieved with respect to one or more relevant points, such as power efficiency, lifetime or the color coordinate of the emitted light. [0003] According to the invention, the term "electroluminescent device" is understood as organic light-emitting transistors (OLETs), organic field-quenched devices (OFQDs), organic ...

Claims

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Application Information

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IPC IPC(8): C09K11/06H05B33/14H01L51/50
CPCC09K11/06H05B33/14C09K2211/1011C09K2211/1014C07C2603/18C07C2603/94C07F7/081C07D209/86C07D219/02C07D307/91C07D333/76C07D405/12Y02E10/549H10K50/15C07C209/10C07C211/61C07C213/02C07C217/94H10K50/181H10K85/633H10K85/636H10K85/6574H10K85/6576H10K85/6572H10K85/40H10K85/655H10K85/631H10K85/653H10K85/654C07F7/083
Inventor 特雷莎·穆希卡-费尔瑙德埃尔维拉·蒙特内格罗埃米尔·侯赛因·帕勒姆阿尔内·比辛弗兰克·福格斯
Owner MERCK PATENT GMBH
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