Skip to main content
Log in

Photoreactive Polynorbornene Bearing 4-(Diphenylamino)benzoate Groups: Synthesis and Application in Electroluminescent Devices

  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Summary.

A new fluorescent and photoreactive polymer, poly-(endo,exo-bis(4-(4-(diphenylamino)benzoyloxy)benzyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate), was prepared by ring opening metathesis polymerization. This polymer combines the photoreactivity of aryl esters with the fluorescence properties of derivatives of 4-(diphenylamino)benzoic acid. The polymer exhibits blue photo- and electroluminescence and can be used as active layer in organic light emitting devices (OLED). Upon irradiation with UV light (254 nm) the aromatic ester groups undergo decarboxylation, which is accompanied by the loss of photoluminescence. Photolithographic patterning of the polymer surface was used to obtain structured fluorescent surfaces and patterned OLEDs.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • C Preininger U Sauer W Kern J Dayteg (2004) Anal Chem 76 6130 Occurrence Handle10.1021/ac0499468 Occurrence Handle1:CAS:528:DC%2BD2cXnsV2it70%3D

    Article  CAS  Google Scholar 

  • G Kranzelbinder E Toussaere J Zyss T Kavc G Langer W Kern (2003) Appl Phys Lett 82 2203 Occurrence Handle10.1063/1.1559952 Occurrence Handle1:CAS:528:DC%2BD3sXis1OlsL0%3D

    Article  CAS  Google Scholar 

  • T Kavc G Langer W Kern G Kranzelbinder E Toussaere GA Turnbull IDW Samuel KF Iskra T Neger A Pogantsch (2004) Chem Mater 14 4178 Occurrence Handle10.1021/cm021148f

    Article  Google Scholar 

  • T Kavc G Langer P Polt K Reichmann W Kern (2002) Macromol Chem Phys 203 1099 Occurrence Handle10.1002/1521-3935(20020501)203:8<1099::AID-MACP1099>3.0.CO;2-M Occurrence Handle1:CAS:528:DC%2BD38XltVygtb0%3D

    Article  CAS  Google Scholar 

  • G Langer T Kavc W Kern G Kranzelbinder E Toussaere (2001) Macromol Chem Phys 202 3459 Occurrence Handle10.1002/1521-3935(20011201)202:18<3459::AID-MACP3459>3.0.CO;2-Y Occurrence Handle1:CAS:528:DC%2BD38XoslynsQ%3D%3D

    Article  CAS  Google Scholar 

  • MR Weinberger G Langer A Pogantsch A Haase E Zojer W Kern (2004) Adv Mater 16 30 Occurrence Handle10.1002/adma.200305681

    Article  Google Scholar 

  • W Schofberger N Zaami KA Mahler G Langer G Jakopic A Pogantsch W Kern F Stelzer (2003) Macromol Chem Phys 204 779 Occurrence Handle10.1002/macp.200390063 Occurrence Handle1:CAS:528:DC%2BD3sXjslOks7g%3D

    Article  CAS  Google Scholar 

  • T Höfler T Grießer X Gstrein G Trimmel G Jakopic W Kern (2007) Polymer 48 1930 Occurrence Handle10.1016/j.polymer.2007.01.041

    Article  Google Scholar 

  • Anderson JC, Reese CB (1960) Proc Chem Soc 217

  • D Bellus P Hrdlovic (1967) Chem Rev 67 599 Occurrence Handle10.1021/cr60250a001 Occurrence Handle1:CAS:528:DyaF1cXmvVSqtw%3D%3D

    Article  CAS  Google Scholar 

  • CE Kalmus DM Hercules (1974) J Am Chem Soc 96 449 Occurrence Handle10.1021/ja00809a021 Occurrence Handle1:CAS:528:DyaE2cXotFOitw%3D%3D

    Article  CAS  Google Scholar 

  • MA Miranda F Galindo (2004) Photo-Fries Reaction and Related Processes WM Horspool (Eds) CRC Handbook of Organic Photochemistry and Photobiology EditionNumber2 CRC Press Boca Raton

    Google Scholar 

  • J Kopezky (1992) Photochemistry, a visual approach, chapter 10 VCH New York

    Google Scholar 

  • RA Finnegan D Knutson (1968) Tetrahedron Lett 9 3429 Occurrence Handle10.1016/S0040-4039(00)89510-6

    Article  Google Scholar 

  • G Weiqiang DJ Abdallah RG Weiss (2001) J Photochem Photobiol A: Chem 139 79 Occurrence Handle10.1016/S1010-6030(00)00411-1

    Article  Google Scholar 

  • Z Chen Z Zhang T Zhao F Bai Y Zhang Z Wang (2001) Spectrochim Acta A 57 419 Occurrence Handle10.1016/S1386-1425(00)00350-4 Occurrence Handle1:STN:280:DC%2BD3M3gvFSrtg%3D%3D

    Article  CAS  Google Scholar 

  • a) Bellmann E, Shaheen SE, Thayumanavan S, Barlow S, Grubbs RH, Marder SR, Kippelen B, Peyghambarian (1998) Chem Mater 10: 1668; b) Nomura M, Fukukawa K, Shibasaki Y, Ueda M (2002) Synth Met 132: 9; c) Stampor W, Mroz W (2007) Chem Phys 331: 261

  • M Behl R Zentel DJ Broer (2004) Macromol Rapid Commun 25 1765 Occurrence Handle10.1002/marc.200400321 Occurrence Handle1:CAS:528:DC%2BD2cXpvV2hu7s%3D

    Article  CAS  Google Scholar 

  • C Slugovc (2004) Macrom Rapid Commun 25 1283 Occurrence Handle10.1002/marc.200400150 Occurrence Handle1:CAS:528:DC%2BD2cXmsFersro%3D

    Article  CAS  Google Scholar 

  • JA Love JP Morgan TM Trnka RH Grubbs (2002) Angew Chem Int Edit 41 4035 Occurrence Handle10.1002/1521-3773(20021104)41:21<4035::AID-ANIE4035>3.0.CO;2-I Occurrence Handle1:CAS:528:DC%2BD38XptVyhtLc%3D

    Article  CAS  Google Scholar 

  • Spectral database of organic compounds, National Institute of Advanced Industrial Science and Technology (2007) SDBS No 7164 (http://www.aist.go.jp/RIODB/SDBS/cgi-bin/cre_index.cgi)

  • MS Sanford JA Love RH Grubbs (2001) Organometallics 20 5314 Occurrence Handle10.1021/om010599r Occurrence Handle1:CAS:528:DC%2BD3MXnvFyrt7o%3D

    Article  CAS  Google Scholar 

  • HE Gottlieb V Kotylar A Nudelman (1997) J Org Chem 62 7512 Occurrence Handle10.1021/jo971176v Occurrence Handle1:CAS:528:DyaK2sXmvVClsbo%3D

    Article  CAS  Google Scholar 

  • Hattori T, Satoh T, Miyano S (1996) Synthesis 514

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Gregor Trimmel.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Griesser, T., Rath, T., Stecher, H. et al. Photoreactive Polynorbornene Bearing 4-(Diphenylamino)benzoate Groups: Synthesis and Application in Electroluminescent Devices. Monatsh. Chem. 138, 269–276 (2007). https://doi.org/10.1007/s00706-007-0613-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-007-0613-6

Navigation