Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Derivatives of 2-diarylaminofluorene and organic electronic compounds containing them

An organic and radical technology, applied in the field of organic compounds, can solve problems such as poor performance data and high operating voltage

Active Publication Date: 2015-04-01
MERCK PATENT GMBH
View PDF84 Cites 7 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In practice, hole transport layers are usually required to have larger layer thicknesses, but this often results in higher operating voltages and poorer performance data

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Derivatives of 2-diarylaminofluorene and organic electronic compounds containing them
  • Derivatives of 2-diarylaminofluorene and organic electronic compounds containing them
  • Derivatives of 2-diarylaminofluorene and organic electronic compounds containing them

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0241] Compound biphenyl-2-ylbiphenyl-4-yl-(9,9-dimethyl-9H-fluoren-2-yl)amine (1-1) and compounds (1-2) to (1-5) Synthesis

[0242]

[0243] 23.5 g of biphenyl-2-ylbiphenyl-4-ylamine (73 mmol) and 20.0 g of 2-bromofluorene (73 mmol) were dissolved in 500 ml of toluene: the solution was degassed and washed with N 2 saturation. Then 2.52 g (2.93 mmol) of tri-tert-butylphosphine and 0.33 g (1.46 mmol) of palladium(II) acetate were added. Subsequently 10.8 g of sodium tert-butoxide (110 mmol) were added. The reaction mixture was heated at boiling under a protective atmosphere for 6 hours. The mixture was then partitioned between toluene and water, and the organic phase was washed three times with water, washed with Na 2 SO 4 Dry and evaporate in a rotary evaporator. After filtration of the crude product with toluene through silica gel, the residue that remains is recrystallized from heptane / toluene and finally sublimed in high vacuum. The purity is 99.9%. Yield 32.0 g ...

Embodiment 2

[0248] Compound biphenyl-2-ylbiphenyl-4-yl-(9,9-diphenyl-9H-fluoren-3-yl)amine (2-1) and compounds (2-2) to (2-10) Synthesis

[0249]

[0250] 2-Bromo-9,9-diphenyl-9H-fluorene (2-1)

[0251] 30 g (103 mmol) of methyl 4'-bromobiphenyl-2-carboxylate were dissolved in 500 ml of dry THF in a flask which had been dried by heating. The clear solution was cooled to -10°C and then 102 ml (307 mmol) of freshly prepared 3 M 2-phenylmagnesium bromide solution were added. The reaction mixture was slowly warmed to room temperature and then treated with NH 4 Cl (500ml) quenched. The mixture was then partitioned between ethyl acetate and water, and the organic phase was washed three times with water, washed with Na 2 SO 4 Dry and evaporate in a rotary evaporator. 400 ml of acetic acid were carefully added to the residue. Then 80 ml of fuming hydrochloric acid were added. The batch was heated to 75°C and held at this temperature for 5 hours. During this time a white solid precipit...

Embodiment 3

[0261] Compound biphenyl-4-ylbiphenyl-2-yl-(9,9-dimethyl-7-phenyl-9H-fluoren-2-yl)amine (3-1) and compound (3-2) to Synthesis of (3-8)

[0262]

[0263] 9,9-Dimethyl-7-phenyl-9H-fluorene

[0264] Suspend 8.9 g (73 mmol) of phenylboronic acid and 20 g (73 mmol) of 2-bromo-9,9'-dimethyl-9H-fluorene in 330 ml of dimethoxyethane and 110 ml of 2 M Na 2 CO 3 in solution. To this suspension was added 2.54 g (2.0 mmol) tetrakis(triphenylphosphine)palladium. The reaction mixture was heated at reflux for 16 hours. After cooling, the reaction mixture was diluted with ethyl acetate and the organic phase was separated off, washed three times with 100 ml of water and then evaporated to dryness. The crude product was filtered through silica gel using heptane / ethyl acetate (20:1 ) to yield 18.8 g (95%) of 9,9-dimethyl-7-phenyl-9H-fluorene.

[0265] The following fluorenes were prepared analogously.

[0266]

[0267] 2-Bromo-9,9-dimethyl-7-phenyl-9H-fluorene

[0268] Dissolve 29....

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
Thicknessaaaaaaaaaa
Thicknessaaaaaaaaaa
Login to View More

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 novel organic compounds, to the use of said compounds in electroluminescent devices, and to electroluminescent devices comprising at least one of said compounds. The invention also relates to processes for the preparation of said compounds and to compositions and formulations comprising at least one of said compounds. Background technique [0002] The development of functional compounds for use in electronic devices is the subject of intense current research. The object here is in particular to develop compounds with which improvements in the properties of electroluminescent devices can be achieved at one or more relevant points, such as power efficiency, lifetime or color coordinates of the emitted light . [0003] According to the present invention, the term electroluminescent device is considered to mean, inter alia, organic light-emitting transistors (OLETs), organic field-quenched devices (OFQDs), organic light-e...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): H05B33/20H01L27/32C09K11/06
CPCC09K11/06H05B33/20C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1088C09K2211/1433C09K2211/185Y02E10/549C07C2603/18C07D307/91H10K85/615H10K85/631H10K50/15H10K50/11H10K50/17C07C211/61H10K85/633H10K85/115H10K85/636H10K50/18H10K85/626H10K85/6574
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com