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

Crosslinkable arylamine compounds and conjugated oligomers of polymers based thereon

A technology of oligomers and polymers, which is applied in the field of electroluminescent devices, can solve the problems of limited charge transport capacity and lack of conjugated polymer skeleton, and achieve the effects of reducing ionization potential, improving charge transport performance, and improving conductivity

Active Publication Date: 2012-11-28
SUMITOMO CHEM CO LTD
View PDF13 Cites 9 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above references, within the scope of the disclosed cross-linked polymers, lack a conjugated polymer backbone and have only limited charge transport capabilities

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
  • Crosslinkable arylamine compounds and conjugated oligomers of polymers based thereon
  • Crosslinkable arylamine compounds and conjugated oligomers of polymers based thereon
  • Crosslinkable arylamine compounds and conjugated oligomers of polymers based thereon

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0163] A) Synthesis of Diphenylbenzocyclobutaneamine (1)

[0164] Into a 500 ml three necked round bottom flask equipped with a mechanical stirrer, nitrogen inlet and reflux condenser (with nitrogen outlet), palladium(II) acetate (196 mg, 1.20 mmol) and tris(ortho-tolyl)phosphine ( 731mg, 2.40mmol) was added to 100ml of toluene. Under nitrogen, the mixture was stirred at room temperature until the palladium catalyst dissolved and the solution turned yellow. Diphenylamine (20.0 g, 118 mmol), bromobenzocyclobutane (23.8 g, 130 mmol) and 400 ml of toluene were added, followed by sodium tert-butoxide (22.8 g, 237 mmol). The reaction mixture turned black by the addition of sodium tert-butoxide. The reaction mixture was heated to reflux under nitrogen for 22 hours. The reaction was quenched by adding 30 ml of 1M aqueous HCl. with 2M Na 2 CO 3 (100 ml) to wash the toluene layer, and then pass the toluene solution over basic alumina. Evaporation of toluene gave a yellow oil. T...

Embodiment 2

[0168] A) Synthesis of fluorene / triarylamine containing BCB(P1) polymer

[0169] Into a 1-liter three-neck round bottom flask equipped with a reflux condenser and an overhead stirrer, the following monomers were added: F8BE (3.863 g, 7.283 mmol), TFB (3.177 g, 6.919 mmol) and compound 2 (156.3 mg , 0.364mmol). Add 0.74M quaternary ammonium chloride catalyst (Aliquat TM 336, obtained from Sigma-Aldrich Corporation, 3.1 ml) in toluene, followed by 50 ml of toluene. Add PdCl 2 (PPh 3 ) 2 After the catalyst (4.9 mg), the mixture was stirred in an oil bath (105° C.) until all monomers had dissolved (ca. 15 minutes). Aqueous sodium carbonate (2.0M, 14ml) was added and the reaction mixture was stirred in an oil bath (105°C) for 16.5 hours. Then, phenylboronic acid (0.5 g) was added, and the reaction mixture was stirred for 7 hours. The aqueous layer was removed, and the organic layer was washed with 50 ml of water. The organic layer was returned to the reaction flask, and 0.7...

Embodiment 3

[0171] Scheme 2 shows the synthesis of a phenylenediamine monomer containing a crosslinkable benzocyclobutane group, and the polymerization was used to prepare a fluorene / amine containing 5 mole % of a crosslinkable moiety that would give conjugated crosslinks copolymer.

[0172]

[0173] route 2

[0174] A) Synthesis of N, N'-diphenyl-N, N'-dibenzocyclobutane-1,4-phenylenediamine (3)

[0175] Into a 500 ml three necked round bottom flask equipped with mechanical stirrer, nitrogen inlet and reflux condenser (with nitrogen outlet), palladium(II) acetate (173 mg, 0.80 mmol) and tris(ortho-tolyl)phosphine (486 mg , 1.60mmol) was added to 50ml of toluene. Under nitrogen, the mixture was stirred at room temperature until the palladium catalyst dissolved and the solution turned yellow. Add N,N'-diphenyl-1,4-phenylenediamine (10.0 g, 38.4 mmol), bromobenzocyclobutane (15.5 g, 76.8 mmol) and 200 ml of toluene, followed by sodium tert-butoxide (7.37 g, 76.8 mmol). The reaction ...

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
molecular weightaaaaaaaaaa
thicknessaaaaaaaaaa
thicknessaaaaaaaaaa
Login to View More

Abstract

Crosslinkable arylamine compounds; oligomers and polymers prepared from such crosslinkable arylamine compounds; films and coatings; and multilayer electronic devices comprising such films are disclosed.

Description

[0001] The application date is October 25, 2004, the international application number is PCT / US2004 / 035221, the title of the invention is "crosslinkable arylamine compounds and conjugated oligomers or polymers based on them" and A divisional application of the application with national application number 200480033957.0. technical field [0002] The present invention relates to novel crosslinkable arylamine compounds and a process for their preparation. The present invention also relates to oligomers and polymers of such compounds, including crosslinked derivatives thereof, and films and coatings prepared from such compounds, oligomers or polymers, and to films and coatings comprising one or more layers of such compounds. Electronic devices of polymer films, especially electroluminescent devices. Background technique [0003] US Patents 6,605,373, 6,362,310, 6,255,449, 6,255,447, 6,169,163, 5,962,631 and related patents disclose certain crosslinkable substituted fluorene com...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/02C08G73/06C07C211/60C07C209/74H01L51/54
CPCH01L51/0035C07D241/46C08G73/02C07D209/86H01L51/0039C07D265/38C07C211/61C07D279/18H01L51/0043C07C2102/06C07C211/60C07C2103/18Y02E10/549H01L51/5048C07C2602/06C07C2603/18H10K85/111H10K85/115H10K85/151H10K50/14C07F5/02C09K11/06C08G73/00C07C211/00
Inventor S·盖纳M·因巴斯卡格J·J·奥布赖恩D·M·威尔士
Owner SUMITOMO CHEM CO LTD
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