Semiperfluoroalkyl Polyfluorenes for Orthogonal Processing in Fluorous Solvents

Lee, Jin‐Kyun; Fong, Hon Hang; Zakhidov, Alex; McCluskey, Georgia E.; Taylor, Priscilla G.; Santiago-Berríos, Mitk’El B.; Abruña, Héctor D.; Holmes, Andrew B.; Malliaras, George G.; Ober, Christopher K.

doi:10.1021/ma902179s

Cited by 39 publications

(41 citation statements)

References 27 publications

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“…Another approach based on conventional lithographic patterning takes advantage of the orthogonality between highly fluorinated LEPs and standard photoresists. [15,16,17] However, the choice of materials for these traditional lithography approaches is limited, thus restricting the flexibility and performance of available OLED architectures.…”

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confidence: 99%

Photo‐patterning of Highly Efficient State‐of‐the‐Art Phosphorescent OLEDs Using Orthogonal Hydrofluoroethers

Krotkus

Ventsch

Kasemann

et al. 2014

Advanced Optical Materials

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Together with "back plane" electronic components and highly efficient "front plane" light-emitting devices, the successful implementation of pixel patterning is a key requirement for the success of organic light-emitting diode (OLED) displays. Prerequisites for patterning techniques include cost-efficiency, scalability to large area substrates (≥Gen 8), registration between multiple layers, and compatibility with state-of-the-art OLED technology. At present, state-of-the-art OLEDs are predominantly based on multilayered thin films of thermally evaporated small molecules and frequently contain phosphorescent emitters. This approach enables internal quantum efficiencies reaching unity [1] and operational lifetimes suitable for commercial display applications. [2,3,4,5,6] A common technique to fabricate multicolor pixelated OLED devices is shadow mask patterning. However, there are severe limitations

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confidence: 99%

Photo‐patterning of Highly Efficient State‐of‐the‐Art Phosphorescent OLEDs Using Orthogonal Hydrofluoroethers

Krotkus

Ventsch

Kasemann

et al. 2014

Advanced Optical Materials

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“…This feature would allow for orthogonal processing of optoelectronic devices with multi-layered configurations, in which successive layer deposition is required, while keeping the underlying polymer layers intact. [10] Herein, we report the synthesis of a highly fluorinated conjugated polymer, poly-(2,3-bis(perfluorohexyl)thieno[3,4-b]pyrazine) (PPFHTP, Figure 1 a), on the first fluorinated version of poly(thieno-[3,4-b]pyrazine)s (pC n TPs), [11,12] which are low-bandgap polymers. [13] The fluorinated polymer exhibited selective solubility in perfluorinated solvents, high air-and thermal stability, high EA, electrochemical n-doping behavior, and a low bandgap.…”

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confidence: 99%

An Air‐Stable Low‐Bandgap n‐Type Organic Polymer Semiconductor Exhibiting Selective Solubility in Perfluorinated Solvents

Takeda¹,

Andrew²,

Lobez³

et al. 2012

Angewandte Chemie

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Ein n‐dotierter polymerer Halbleiter, Poly(2,3‐bis(perfluorohexyl)thieno[3,4‐b]pyrazin), wurde durch Pd‐katalysierte Polykondensation in einem mehrphasigen Lösungsmittelsystem synthetisiert. Dies ist das erste Beispiel für einen n‐dotieren polymeren Halbleiter, der ausschließlich in fluorierten Lösungsmitteln löslich ist. Der Halbleiter wurde zur Fertigung organischer Feldeffekttransistoren genutzt (siehe Bild).

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“…In general, the spectral stability of the devices was rather poor for all materials under continuous operation. This instability was attributed to the electron-withdrawing nature of the semiperfluorinated side chains, which, according to Lee et al, [14] were able to form charge-carrier traps in the device. The resulting accumulation of trapped charges might induce an electrochemical degradation of the polymer; thus explaining the poor spectral stability.…”

Section: Device Characteristicsmentioning

confidence: 99%

“…Recently, the first PF with semifluorinated side chains (fPF), soluble in fluorinated solvents, was synthesized and tested in polymer light-emitting diodes (PLEDs) by Ober et al [14] AlAbstract: A series of novel polyfluorenes, soluble exclusively in perfluorinated solvents, were prepared. The new materials were studied with regard to orthogonal processing of organic electronic materials.…”

Section: Introductionmentioning

confidence: 99%

Controlling Polymer Solubility: Polyfluorenes with Branched Semiperfluorinated Side Chains for Polymer Light‐Emitting Diodes

Певзнер

Auer

Trattnig

et al. 2014

Israel Journal of Chemistry

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A series of novel polyfluorenes, soluble exclusively in perfluorinated solvents, were prepared. The new materials were studied with regard to orthogonal processing of organic electronic materials. The desired solubility was achieved by introducing semifluorinated side chains to the fluorene monomers. Since the use of long perfluoroalkyl chains (RF) is restricted due to public health concerns, a synthetic route for polyfluorenes with short RF chains branched by aromatic units has been developed. The photophysical behavior of the resulting polymers was investigated in solution and thin films by UV/Vis absorption and photoluminescence spectroscopy. The photoluminescence quantum yields were found to be in the range of those of alkylated polyfluorenes. The electroluminescent properties were studied in single‐layer polymer light‐emitting diodes, with the new polymers as active materials, which exhibited similar characteristics to previously published single‐layer devices with polyfluorenes containing long RF. The wetting properties of different polyfluorene films containing fluorinated, polar, polyethylene glycol, or nonpolar alkyl groups were investigated by contact angle measurements.

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Semiperfluoroalkyl Polyfluorenes for Orthogonal Processing in Fluorous Solvents

Cited by 39 publications

References 27 publications

Photo‐patterning of Highly Efficient State‐of‐the‐Art Phosphorescent OLEDs Using Orthogonal Hydrofluoroethers

Photo‐patterning of Highly Efficient State‐of‐the‐Art Phosphorescent OLEDs Using Orthogonal Hydrofluoroethers

An Air‐Stable Low‐Bandgap n‐Type Organic Polymer Semiconductor Exhibiting Selective Solubility in Perfluorinated Solvents

Controlling Polymer Solubility: Polyfluorenes with Branched Semiperfluorinated Side Chains for Polymer Light‐Emitting Diodes

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