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Compounds and Organic Electroluminescent Devices

A technology for electroluminescent devices and compounds, applied in the field of preparing said compounds and organic electroluminescent devices, capable of solving problems such as poor performance data and high operating voltage

Active Publication Date: 2019-07-26
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 was dissolved in 500 mL of dry THF in a thoroughly heated flask. Solution with N 2 Saturate and add 15.0 g (170 mmol) of cerium(III) chloride. 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 NH 4 Cl quench (500 mL). The mixture was then partitioned between acetate and water, the organic phase was washed three times with water and passed through Na 2 SO 4 Dry and rotary evaporate. Add 60 mL of toluene to the rotary evaporated solution. The precipitate was heated to 50°C and then 27.2 mL of trifluoromethanesu...

example 2

[0323] 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] 30 g (94 mmol) of 2,2'-dibromobiphenyl was dissolved 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-butyl lithium in hexane (94 mmol) was slowly added dropwise (duration: about 1 hour). The precipitate was stirred at -70°C for 1 hour. Subsequently, 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, with NH 4 The Cl is quenched and then concentrated on a rotary evaporator. Carefully add 300 mL of acetic acid to the rotary evaporated solution, and then add 50 mL of fuming hydrochloric acid. ...

example 3

[0337] Synthetic compound biphenyl-4-yl-biphenyl-2-yl-(7,9-diphenyl-9-p-tolyl-9H-fluoren-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-phenylfluorene-9-one

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

[0342] The following brominated compounds were prepared similarly:

[0343]

[0344] 2-bromo-7,9...

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Abstract

The present invention relates to certain fluorenes, the use of these compounds in electronic devices, and electronic devices containing at least one of these compounds. Furthermore, the invention relates to a process for the preparation of the compounds as well as to a formulation and composition containing one or more of these 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 containing at least one of the compounds. In addition, the present invention also relates to a method for preparing the compound as well as compositions and preparations containing at least one of the compounds. Background technique [0002] The development of functional compounds for electroluminescent devices is currently a subject of intensive research. Here, the goal is particularly to develop compounds by which electroluminescent devices can obtain improved performance on one or more relevant points, such as power efficiency, lifetime or the color coordinates of the emitted light. [0003] According to the present invention, the concept "electroluminescent device" is understood as organic light emitting transistor (OLET), organic field quenching device (OFQD), organic light emitting electroche...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/16H01L51/50H05B33/14C09K11/06
CPCC09K11/06H05B33/14C09K2211/1011C09K2211/1014C07C2603/18C07C2603/94C07F7/081C07D209/86C07D219/02C07D307/91C07D333/76C07D405/12Y02E10/549H10K50/15C07C209/10C07C211/61C07C213/02C07C217/94H10K85/655H10K85/631H10K85/653H10K85/654C07F7/083
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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