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Compounds for use in Opto-Electrical Devices

Inactive Publication Date: 2010-01-21
SUMITOMO CHEM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0035]It has been found that by providing a solubilising substituent on a small molecule triazine compound, the compound can be readily solution processed. As such, the compositions comprising small molecule triazine compounds of the present invention can be deposited to form a film by, for example, ink-jet printing or spin-coating rather than thermal vapour deposition.
[0049]It has been found that solution processable triazine materials are excellent hosts for phosphorescent emissive materials as their deep LUMO provide enhanced electron-injection / transport and their wide triplet band-gap reduces quenching. The advantageous features described in relation to the first aspect of the invention are also applicable to the second aspect of the invention.

Problems solved by technology

A problem with known host-phosphor systems is that the host may quench emission from the phosphor.
However, the present applicant proposes that this nitrogen linkage is not completely stable which can reduce the lifetime of these compositions.
Furthermore, none of the above-identified small molecule compounds are soluble enough to be readily solution processed and instead these compounds are more suited to vacuum thermal deposition.
As with phosphorescent systems, a problem with known host-fluorescent emitter systems is that the host may quench emission from the fluorescent emitter.
Another factor affecting the performance of opto-electonic devices is morphology of the films which make up the device.

Method used

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  • Compounds for use in Opto-Electrical Devices
  • Compounds for use in Opto-Electrical Devices
  • Compounds for use in Opto-Electrical Devices

Examples

Experimental program
Comparison scheme
Effect test

examples

2,4,6-tris(4′-bromophenyl)-1,3,5-triazine(1)

[0110]A 1 L three-necked round bottomed flask was fitted with a magnetic stirrer, a reflux condenser with N2 inlet bubbler, and a 500 ml pressure-equalising dropping funnel. The flask was charged with trifluoromethane sulfonic acid (60 g, 35 ml) that was stirred at room temperature. In a separate flask 4-bromobenzonitrile (36.4 g, 0.20 mol) was dissolved in anhydrous CHCl3 (500 ml) and the solution transferred into the dropping funnel under N2 via cannula. The benzonitrile solution was added dropwise and then the reaction mixture was heated to reflux at 90-95° C. for 20-24 hours. The reaction mixture was allowed to cool before cautiously adding to stirred dilute aqueous ammonia solution (250 ml, 3%) cooled in an ice-bath. The product precipitated as an off-white solid and was collected by filtration and washed with H2O and Et2O. The product was recrystallised from refluxing toluene to give pure product (100% by HPLC). Yield 24.0 g, 66%.

2,4...

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Abstract

A composition for use in fabricating opto-electrical devices comprising a solution processable triazine host material and a phosphorescent moiety.

Description

FIELD OF INVENTION[0001]This invention relates to compositions comprising triazine host compounds for use in fabricating phosphorescent opto-electrical devices, and methods of fabricating opto-electrical devices using these compositions.BACKGROUND OF INVENTION[0002]One class of opto-electrical devices is that using an organic material for light emission or detection. The basic structure of these devices is a light emissive organic layer, for instance a film of a poly(p-phenylenevinylene) (“PPV”) or polyfluorene, sandwiched between a cathode for injecting negative charge carriers (electrons) and an anode for injecting positive charge carriers (holes) into the organic layer. The electrons and holes combine in the organic layer generating photons. In WO 90 / 13148 the organic light-emissive material is a polymer. In U.S. Pat. No. 4,539,507 the organic light-emissive material is of the class known as small molecule materials, such as (8-hydroxyquinoline)aluminium (“Alq3”). In a practical ...

Claims

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Application Information

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IPC IPC(8): H01J1/62C07D251/24C08G73/06C09K11/00B05D5/12
CPCC09K11/06C09K2211/1059C09K2211/185H01L51/0043H01L51/5024H05B33/14H01L51/0007H01L51/0067H01L51/5004H01L51/5016C09K11/025H10K85/151H10K50/11H10K2101/10H10K71/15H10K85/225H10K85/654H10K50/12H10K85/111H10K85/342H10K71/12H10K2101/40C07F15/0033
Inventor MALE, NIGELPILLWO, JONATHAN
Owner SUMITOMO CHEM CO LTD
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