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Crosslinkable substituted fluorene compounds and conjugated oligomers or polymers based thereon

A compound and substituent technology, applied in the field of electroluminescent devices, can solve the problems of limited charge transport ability and lack of conjugated polymer skeleton, and achieve the effects of reducing ionization potential, improving charge transport performance, and improving conductivity

Active Publication Date: 2006-12-20
SUMITOMO CHEM CO LTD
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  • 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

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  • Crosslinkable substituted fluorene compounds and conjugated oligomers or polymers based thereon
  • Crosslinkable substituted fluorene compounds and conjugated oligomers or polymers based thereon
  • Crosslinkable substituted fluorene compounds and conjugated oligomers or polymers based thereon

Examples

Experimental program
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Embodiment 1

[0128] Cross-linked polymers of the following 6 monomer units were prepared using typical Suzuki coupling reaction conditions. The various monomer unit amounts used are reported in Table 1. The resulting polymer compositions are reported in Table 2.

[0129] monomer

[0130]

[0131] monomer synthesis

[0132] 1) C6BE (2,7-bis(1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene)

[0133] A 500 mL three-neck round bottom flask equipped with an overhead stirrer, addition funnel, and condenser connected to a nitrogen line was charged with 2,7-dibromo-9,9-dioctylfluorene (21.9 g, 40 mmol) and THF (200 mL). The mixture was stirred and cooled to about -77°C in an acetone dry ice bath. With nitrogen sparging, n-butyllithium (2.5 M in hexane, 33.6 mL, 84 mmol) was added dropwise over about 10 minutes. A yellow solution formed which gradually turned cloudy. The mixture was stirred for an additional 90 minutes at -77°C. Tris-isopropyl borate (22.6 g, 120 mmol) was then added dropwis...

Embodiment 2

[0155] The reaction scheme below discloses the preparation of triarylamine dibromide compounds containing crosslinkable benzocyclobutane functional groups, and their combination with 9,9-bis(vinylbenzyl)-2,7-fluorenyl Use in the polymerization of diboride and bis(p-bromophenyl)(p-isobutylphenyl)amine to prepare crosslinkable copolymers according to the invention.

[0156]

[0157] In this scheme, "o-tolyl" means "o-tolyl", "toluene" means "toluene", and "surfactant" means "surfactant".

[0158] A) the synthesis of diphenylbenzocyclobutaneamine

[0159] 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 mmo...

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Abstract

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

Description

[0001] cross-reference statement [0002] This application claims priority to US Provisional Application No. 60 / 520,597, filed November 17, 2003. technical field [0003] The present invention relates to novel crosslinkable fluorene compounds and a process for their preparation. The present invention also relates to oligomers and polymers of such compounds, said compounds including crosslinked derivatives thereof, and films and coatings prepared from such compounds, oligomers or polymers, the preparation of such films and Methods of coating, and electronic devices, especially electroluminescent devices, comprising one or more layers of such polymer films. Background technique [0004] 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 compounds, and oligomers and polymers derived therefrom. Macromolecular Rapid Communication 21, 583-589 (2000) describes the synthesis of arylam...

Claims

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Application Information

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IPC IPC(8): C08G61/02C09K11/06C07C25/22C07F5/02C07C25/24C07C211/60C08G61/10C08G61/12C08G73/02C08G73/08C08G73/22H01L51/00H01L51/30H01L51/50H05B33/14
CPCC07C25/22C08L65/00C08G73/22Y10S428/917C08G2261/1414C09K2211/1416C09K11/06C07C25/24H01L2251/308C07C211/60H01L51/5048H01L51/0035C08G61/123C08G61/10H01L51/0059C07F5/025H01L51/006C08G61/12H01L51/0039C08G61/02H05B33/14H01L51/0052C08G73/08C08G61/126H01L51/0043C08G73/02C07C2102/06C07C2103/18C07C2602/06C07C2603/18Y10T428/31504H10K85/115H10K85/111H10K85/151H10K85/615H10K85/631H10K85/633H10K50/14H10K2102/103C07F5/02C09K2211/1408
Inventor M·因巴斯卡格余旺林
Owner SUMITOMO CHEM CO LTD
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