Fluorinated monomers, oligomers and polymers for use in organic electronic devices

Highlights

In organic electronic devices, such as electroluminescence devices, field effect transistors and organic solar cells, the key component is the organic semiconducting material. To obtain the desired properties and performance of this material, the chemical structures must be carefully made, controlled and optimized.

Fluorinated conjugated polymers have advantages as semiconducting materials, including the ability to increase the open circuit voltage of photovoltaic devices, improve resistance against degradation and enhance charge carrier mobility. However, the number of fluorinated monomers with strong electron withdrawing ability is limited. Also, current methods for introducing fluorine atoms on to an organic molecule are complex, involving multi-step synthesis and stringent reaction conditions that may not be compatible with many organic groups having electron withdrawing properties.

The technology offered includes a less complex method for introducing two fluorine atoms on the aromatic ring of organic semiconducting materials to yield fluorinated compounds, oligomers and polymers. The resulting difluoro-derivatives of organic semiconducting material can function to enable more finely-tuned band gaps and energy levels, higher carrier mobility, higher open circuit voltage, greater resistance to oxidative degradation and improve the stability of polymers in organic electronic devices.

Technology transfer

This technology is available for licensing, or for further development through a collaborative research agreement with NRC. The business opportunity may be referred to by its NRC ID: 12199.

Market applications

Technology presented in this innovation is of particular interest for making stable di-fluorinated conjugated polymers in the manufacturing of range of optoelectronic devices, including solar cells and OLEDs.

How it works

The commercial use of organic electronic devices has been increasing in recent years in the form of electroluminescence devices, field effect transistors and organic solar cells, etc. In all these devices, the key component is the organic semiconducting material. The chemical structures of these organic materials must be carefully controlled and optimized for energy performance, stability, solid state packing, solubility, and carrier mobility and other properties.

Fluorinated conjugated polymers show several advantages compared with their non-fluorinated counterparts as organic semiconducting materials with respect to above properties. However, the number of fluorinated monomers with the strong electron withdrawing ability required is quite limited due in large part to the incompatibility between fluorination protocols and their impact on organic electron withdrawing groups.

There are only a very limited number of methods known to successfully introduce fluorine atoms on to an organic molecule. The two most commonly used methods are tedious and involve complex, multi-step synthesis, including very stringent reaction conditions which may not be compatible with many organic groups.

Addressing the need for new fluorinated organic semiconducting materials having improved electronic properties for use in organic electronic devices, the technology offered provides a method for introducing two fluorine atoms onto the aromatic ring of suitable precursor monomers to produce fluorinated monomer compounds, oligomers and polymer.

The difluoro-derivatives of organic semiconducting materials produced by the method have improved electronic properties, including more finely-tuned band gaps and energy levels, higher carrier mobility, higher open circuit voltage, greater resistance to oxidative degradation and better stability. The resulting polymers can be used as active layers in organic electronic devices, for example, optical sensors and solar cells.

Benefits

Fluorinated monomers, oligomers and polymers included in the invention have better properties desired for many organic electronic device applications. These include more finely-tuned band gaps and energy levels, higher carrier mobility, higher open circuit voltage, and greater resistance to oxidative degradation.

Patents

NRC file 12199: http://www.google.com/patents/WO2011060526A1?cl=en

Patent is pending in Canada, the US and Europe.

Contact

Michael Davison, Client Relationship Leader
Telephone:  613-998-9414
EmailMichael.Davison@nrc-cnrc.gc.ca