High-performance polymer semiconducting heterostructure devices by nitrene-mediated photocrosslinking of alkyl side chains (2024)

1. Baldo, M. A. et al. Highly efficient phosphorescent emission from organic electroluminescent devices. Nature 395, 151–154 (1998).

   Article CAS Google Scholar

2. Walzer, K., Maennig, B., Pfeiffer, M. & Leo, K. Highly efficient organic devicesbased on electrically doped transport layers. Chem. Rev. 107, 1233–1271 (2007).

   Article CAS Google Scholar

3. Groenendaal, L. B., Jonas, F., Freitag, D., Pielartzik, H. & Reynolds, J. R. Poly(3,4-ethylenedioxythiophene) and its derivatives: Past, present, and future. Adv. Mater. 12, 481–494 (2000).

   Article CAS Google Scholar

4. Greenham, N. C., Moratti, S. C., Bradley, D. D. C., Friend, R. H. & Holmes, A. B. Efficient light-emitting diodes based on polymers with high electron-affinities. Nature 365, 628–630 (1993).

   Article CAS Google Scholar

5. Halls, J. J. M. et al. Efficient photodiodes from interpenetrating polymer networks. Nature 376, 498–500 (1995).

   Article CAS Google Scholar

6. Ho, P. K. H. et al. Molecular-scale interface engineering for polymer light-emitting diodes. Nature 404, 481–484 (2000).

   Article CAS Google Scholar

7. Müller, C. D. et al. Multi-colour organic light-emitting displays by solution processing. Nature 421, 829–833 (2003).

   Article Google Scholar

8. Solomeshch, O. et al. Wide band gap cross-linkable semiconductor polymer LED. Synth. Met. 157, 841–845 (2007).

   Article CAS Google Scholar

9. Charas, A. et al. Photoacid cross-linkable polyfluorenes for optoelectronics applications. Synth. Met. 158, 643–653 (2008).

   Article CAS Google Scholar

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   6.2: Spring-Mass Problems (with Damping)Thermal Conductivity - Unit Converting Table2.6: Forced Oscillations and Resonance17.1: First Order Differential Equations

10. Cheng, Y. J. et al. Thermally cross-linkable hole-transporting materials on conducting polymer: Synthesis, characterization and applications for polymer light-emitting devices. Chem. Mater. 20, 413–422 (2008).

    Article CAS Google Scholar

11. Klärner, G. et al. Cross-linkable polymers based on dialkylfluorenes. Chem.Mater. 11, 1800–1805 (1999).

    Google Scholar

12. Keana, J. F. W. & Cai, S. X. New reagents for photoaffinity labeling: Synthesis and photolysis of functionalized perfluorophenyl azides. J. Org. Chem. 55, 3640–3647 (1990).

    Article CAS Google Scholar

13. Cai, S. X., Keana, J. F. W., Nabity, J. C. & Wybourne, M. N. Conducting polymers as deep-UV and electron beam resists: Direct production of micrometre scale conducting structures from poly(3-octylthiophene). J.Mol.Electron. 7, 63–68 (1991).

    CAS Google Scholar

14. Cai, S. X., Glenn, D. J., Kanskar, M., Wybourne, M. N. & Keana, J. F. W. Development of highly efficient deep-UV and electron beam mediated cross-linkers: Synthesis and photolysis of bis(perfluorophenyl) azides. Chem.Mater. 6, 1822–1829 (1994).

    CAS Google Scholar

15. Liu, L., Engelhard, M. H. & Yan, M. Surface and interface control on photochemically initiated immobilisation. J. Am. Chem. Soc. 128, 14067–14072 (2006).

    Article CAS Google Scholar

16. Schnapp, K. A., Poe, R., Leyva, E., Soundararajan, N. & Platz, M. S. Exploratory photochemistry of fluorinated aryl azides: Implications for the design of photoaffinity labeling reagents. Bioconjugate Chem. 4, 172–177 (1993).

    Article CAS Google Scholar

17. Khong, S. H. et al. General photo-patterning and post-deposition modification of polyelectrolyte thin films via efficient ionic bis(fluorinated phenyl azide) photo-crosslinkers. Adv. Funct. Mater. 17, 2490–2499 (2007).

    Article CAS Google Scholar

18. Png, R. Q. et al. Electromigration of the conducting polymer in organic semiconductor devices and its stabilization by crosslinking. Appl. Phys. Lett. 91, 013511 (2007).

    Article Google Scholar

19. Poe, R., Schnapp, K. A., Young, M. J. T., Grayzar, J. & Platz, M. S. Chemistry and kinetics of singlet (pentafluorophenyl)nitrene. J. Am. Chem. Soc. 114, 5054–5067 (1992).

    Article CAS Google Scholar

20. Marcinek, A. et al. Unusually long lifetimes of the singlet nitrenes derived from 4-azido-2,3,5,6-tetrafluorobenzamides. J. Phys. Chem. 98, 412–419 (1994).

    See Also

    Fahrenheit to Celsius conversion: °F to °C calculator

    Article CAS Google Scholar

21. Bräse, S., Gil, C., Knepper, K. & Zimmermann, V. Organic azides: an exploding diversity of a unique class of compounds. Angew. Chem. Int. Ed. 44, 5188–5240 (2005).

    Article Google Scholar

22. Collings, J. C. et al. Arene-perfluoroarene interactions in crystal engineering. Part 3: Single-crystal structures of 1:1 complexes of octafluoronaphthalene with fused-ring polyaromatic hydrocarbons. New J. Chem. 25, 1410–1417 (2001).

    Article CAS Google Scholar

23. Stepto, R. F. T. (ed.) in Polymer Networks: Principles of Their Formation, Structure and Properties (Blackie Academic & Professional, 1998).

24. Morteani, A. C. et al. Barrier-free electron–hole capture in polymer blend heterojunction light-emitting diodes. Adv. Mater. 15, 1708–1712 (2003).

    Article CAS Google Scholar

25. Huang, Y. S. et al. Electronic structures of interfacial states formed at polymeric semiconductor heterojunctions. Nature Mater. 7, 483–489 (2008).

    Article CAS Google Scholar

26. Colthup, N. B., Daly, L. H. & Wiberley, S. E. Introduction to Infrared and Raman Spectroscopy (Academic, 1990).

    Google Scholar

27. Pope, M. & Swenberg, C. E. Electronic Processes in Organic Crystals and Polymers (Oxford Univ. Press, 1999).

    Google Scholar

28. Tanase, C., Meijer, E. J., Blom, P. W. M. & De Leeuw, D. M. Unification of the hole transport in polymeric field-effect transistors and light-emitting diodes. Phys. Rev. Lett. 91, 216601-1-4 (2003).

    Article Google Scholar

29. Craciun, N. I., Brondijk, J. J. & Blom, P. W. M. Diffusion-enhanced hole transport in thin polymer light-emitting diodes. Phys. Rev. B 77,035206-1-5 (2008).

    Article Google Scholar

30. Kim, J. S., Ho, P. K. H., Greenham, N. C. & Friend, R. H. Electroluminescence emission pattern of organic light-emitting diodes: Implications for device efficiency calculations. J. Appl. Phys. 88, 1073–1081 (2000).

    Article CAS Google Scholar

31. Blom, P. W. M., Mihailetchi, V. D., Koster, L. J. A. & Markov, D. E. Device physics of polymer: Fullerene bulk heterojunction solar cells. Adv. Mater. 19, 1551–1566 (2007).

    Article CAS Google Scholar

32. Dennler, G., Scharber, M. C. & Brabec, C. J. Polymer: Fullerene bulk-heterojunction solar cells. Adv. Mater. 2009, 1323–1338 (2009).

    Article Google Scholar

33. Arias, A. C. et al. Photovoltaic performance and morphology of polyfluorene blends: A combined microscopic and photovoltaic investigation. Macromolecules 34, 6005–6013 (2001).

    Article CAS Google Scholar

34. Blom, P. W. M., Mihailetchi, V. D., Koster, L. J. A. & Markov, D. E. Device physics of polymer: Fullerene bulk heterojuction solar cells. Adv. Mater. 19, 1551–1566 (2007).

    Article CAS Google Scholar

35. McCulloch, I. et al. Liquid-crystalline semiconducting polymers with high charge-carrier mobility. Nature Mater. 5, 328–333 (2006).

    Article CAS Google Scholar

36. Spreitzer, H. et al. Soluble phenyl-substituted PPVs—new materials for highly efficient polymer LEDs. Adv. Mater. 10, 1340–1343 (1998).

    Article CAS Google Scholar

37. Becker, H. et al. Soluble PPVs with enhanced performance—a mechanistic approach. Adv. Mater. 12, 42–48 (2000).

    Article CAS Google Scholar

38. Morteani, A. C., Ho, P. K. H., Friend, R. H. & Silva, C. Electric field-induced transition from heterojunction to bulk charge recombination in bilayer polymer light-emitting diodes. Appl. Phys. Lett. 86, 163501 (2005).

    Article Google Scholar

39. Kim, J. S., Friend, R. H., Grizzi, I. & Burroughes, J. H. Spin-cast thin semiconducting polymer interlayer for improving device efficiency of polymer light-emitting diodes. Appl. Phys. Lett. 87, 023506-1-3 (2005).

    Google Scholar

40. Ho, P. K. H., Granström, M., Friend, R. H. & Greenham, N. C. Ultrathin self-assembled layers at the ITO interface to control charge injection and electroluminescence efficiency in polymer light-emitting diodes. Adv. Mater. 10, 769–774 (1998).

    Article CAS Google Scholar

41. Zhou, M. et al. The role of delta-doped interfaces for Ohmic contacts to organic semiconductors. Phys. Rev. Lett. 103, 036601-1-4 (2009).

    Google Scholar

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