Dibenzosilol Polymers, Their Preparation and Uses

a technology of dibenzosilol and polymer, applied in the field of dibenzosilol, can solve the problems of less electrochemical stability prone to degradation, and shorter life of materials containing these lower electron affinities

Inactive Publication Date: 2007-10-25
CAMBRIDGE DISPLAY TECH LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0060] The present inventors have found that polymers comprising dibenzosilole r

Problems solved by technology

A difficulty encountered with blue electroluminescent polymers to date is that their lifetime (i.e. the time taken for brightness to halve from a given starting brightness at fixed current) tends to be shorter than that of corresponding red or green materials.
It is therefore possible that materials comprising these lower electron affinities are less electrochemically stable and so more prone to degradation.
A blue electroluminescent material having a higher electron affinity than polyfluorenes or a material capable of injecting electrons into blue electroluminescent polymers is therefore desirable, however increasing the electron affinity of a wide bandgap material will tend to result in a smaller bandgap thus making the mat

Method used

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  • Dibenzosilol Polymers, Their Preparation and Uses
  • Dibenzosilol Polymers, Their Preparation and Uses
  • Dibenzosilol Polymers, Their Preparation and Uses

Examples

Experimental program
Comparison scheme
Effect test

polymer example 1

[0130] A homopolymer according to the first aspect of the invention was prepared by Suzuki polymerisation of Monomer 1 and Monomer 2 followed by end-capping with bromobenzene and phenylboronic acid according to the following scheme to afford dibenzosilole polymer PS6:

[0131] To a dried Schlenk tube was added 2,7-dibromo-9,9-dihexyl-9H-9-dibenzosilole (84 mg, 0.17 mmol, 1.0 equiv.), 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-9H,9-dihexyldibenzosilole (100 mg, 0.17 mmol, 1.0 equiv.), palladium(II) acetate (1.0 mg, 45 μmol, 2.7%) and tricyclohexylphosphine (5 mg, 178 μmol, 10.7%) under nitrogen atmosphere. Dry toluene (2.5 cm3) was added and the mixture was stirred at 90° C. for 5 min. 20% w / w Tetraethylammonium hydroxide aqueous solution (1.0 cm3) was then added. The mixture was stirred for a further 2 h. To the mixture was then added phenylboronic acid (20.3 mg, 17 mmol, 1.0 equiv.), and after stirring for 1 h, bromobenzene (26.1 mg, 17 mmol, 1.0 equiv.) was added. After ...

polymer example 2

[0132] A copolymer according to the invention was prepared by Suzuki polymerisation as disclosed in WO 00 / 53656 with a diboronic acid of di(n-hexyl)fluorene followed by end-capping with bromobenzene and phenyl boronic acid to afford Polymer PS6F6 as shown below:

Poly(9,9-dihexyl-2,7-fluorenyl-alt-9,9-dihexyl-2,7-silafluorenyl)

[0133]

[0134] To a dried Schlenk tube was added 9,9-dihexyl-2,7-dibromo-9H-9-dibenzosilole (84 mg, 0.17 mmol, 1.0 equiv.), 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-9,9-dihexylfluorene (97 mg, 0.17 mmol, 1.0 equiv.), palladium(II) acetate (1.0 mg, 45 μmol, 2.7%) and tricyclohexylphosphine (5 mg, 178 μmol, 10.7%) under nitrogen atmosphere. Dry toluene (2.5 cm3) was added and the mixture was strred at 90° C. for 5 min. 20% w / w Tetraethylammonium hydroxide aqueous solution (1.0 cm3) was then added. After 1 hour, the mixture became very viscous and additional dry toluene (1.0 cm3) was added. The mixture was stirred for a further 1 h. To the mixture was...

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Abstract

A polymer containing an optionally substituted repeat unit of formula (I) wherein each R is the same or different and represents H or an electron withdrawing group, and each R1 is the same or different and represents a substituent.

Description

FIELD OF THE INVENTION [0001] The invention relates to polymers for electronic and optical applications and the synthesis thereof. BACKGROUND OF THE INVENTION [0002] Organic semiconductors are attracting increasing attention across a wide range of applications due to their advantageous electronic properties and their processability. One class of opto-electrical devices is that using an organic material for light emission (an organic light-emissive device or “OLED”) or for light absorption for the purpose of power generation or light detection (a photovoltaic device). The basic structure of these devices is a semiconducting organic layer, sandwiched between a cathode for injecting or accepting negative charge carriers (electrons) and an anode for injecting or accepting positive charge carriers (holes) into or from the organic layer. For example, an OLED is typically fabricated on a glass or plastic substrate coated with a transparent first electrode such as indium-tin-oxide (“ITO”). ...

Claims

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Application Information

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IPC IPC(8): C08G61/12C07F7/18C07F7/08
CPCC07F7/0818H01L51/0094C08G61/123C07F7/081C07F7/0803C09K11/06C08G61/12C08G77/00C07F7/00C07F7/08H10K85/40H10K50/11H10K50/12H10K85/111H10K85/115H10K85/151H10K2101/30H10K2101/40C07F7/0816C08G2261/12C08G2261/124C08G2261/126C08G2261/148C08G2261/228C08G2261/3142C08G2261/3244C08G2261/3326C08G2261/524C08G2261/95C09K2211/1416C09K2211/1425C09K2211/1441
Inventor TOWNS, CARL R.MAK, CHRISCHAN, KHAI LEOKHOLMES, ANDREW BRUCE
Owner CAMBRIDGE DISPLAY TECH LTD
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