Skip to main content
Log in

The Fluorescence and Electroluminescence Properties of the Carbazole–Phenylazomethine Double Layer-Type Dendrimer

  • Published:
Journal of Inorganic and Organometallic Polymers and Materials Aims and scope Submit manuscript

Abstract

The fluorescence properties of double layer-type dendrimers with carbazole as the outer layer and phenylazomethine as the inner layer of the dendron with a zinc porphyrin core were studied. Based on the fluorescence quantum yield (solution), the effect of the bulky dendron to inhibit the interaction of the chromophores was confirmed. Additionally, the efficient light-harvesting property of the double layer-type dendron was revealed by the fluorescence measurement at several excitation wavelengths. These dendrimers were used as an emitting-layer in an OLED device. The electroluminescence of the core porphyrin was observed and it was shown that the double layer-type dendrimer with a luminescent core has the potential to be a hole-transporting/emitting material.

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.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. C.W. Tang, S.A. Van Slyke, Appl. Phys. Lett. 51, 913 (1987)

    Article  CAS  Google Scholar 

  2. A.P. Kulkarni, C.J. Tonzola, A. Babel, S.A. Jenekhe, Chem. Mater. 16, 4556 (2004)

    Article  CAS  Google Scholar 

  3. Y. Shirota, H. Kageyama, Chem. Rev. 107, 953 (2007)

    Article  CAS  Google Scholar 

  4. J. Kido, K. Hongawa, K. Okuyama, K. Nagai, Appl. Phys. Lett. 63, 2627 (1993)

    Article  CAS  Google Scholar 

  5. J. Kido, M. Kimura, K. Nagai, Science 267, 1332 (1995)

    Article  CAS  Google Scholar 

  6. B. Geffroy, P. le Roy, C. Prat, Polym. Int. 55, 572 (2006)

    Article  CAS  Google Scholar 

  7. O. Nuyken, S. Jungermann, V. Wiederhirn, E. Bacher, K. Meerholz, Monatsh. Chem. 137, 811 (2006)

    Article  CAS  Google Scholar 

  8. K.Y. Hwang, M.H. Lee, H. Jang, Y. Sung, J.S. Lee, S.H. Kim, Y. Do, Dalton Trans. 14, 1818 (2008)

    Article  Google Scholar 

  9. M. Ichikawa, S. Fujimoto, Y. Miyazaki, T. Koyama, N. Yokoyama, T. Miki, Y. Taniguchi, Org. Electron. 9, 77 (2008)

    CAS  Google Scholar 

  10. V.I. Adamovich, S.R. Cordero, P.I. Djurovich, A. Tamayo, M.E. Thompson, B.W. D’Andrade, S.R. Forrest, Org. Electron. 4, 77 (2003)

    Article  CAS  Google Scholar 

  11. Y. Hamada, T. Sano, M. Fujita, T. Fujii, Y. Nishio, K. Shibata, Chem. Lett. 22, 905 (1993)

    Article  Google Scholar 

  12. J. Kido, Y. Iizumi, Chem. Lett. 26, 963 (1997)

    Article  Google Scholar 

  13. N. Nakmura, S. Wakabayashi, K. Miyairi, T. Fujii, Chem. Lett. 23, 1741 (1994)

    Article  Google Scholar 

  14. C. Hosokawa, H. Higashi, H. Nakamura, T. Kusumoto, Appl. Phys. Lett. 67, 3853 (1995)

    Article  CAS  Google Scholar 

  15. K.R.J. Thomas, J.T. Lin, Y.T. Tao, C.W. Ko, Adv. Mater. 12, 1949 (2000)

    Article  CAS  Google Scholar 

  16. J.H. Burroughes, D.D.C. Bradley, A.R. Brown, R.N. Marks, K. MacKay, R.H. Friend, P.L. Burn, A.B. Holmes, Nature 347, 539 (1990)

    Article  CAS  Google Scholar 

  17. N.C. Greenham, S.C. Moratti, D.D.C. Bradley, R.H. Friend, A.B. Holmes, Nature 365, 628 (1993)

    Article  CAS  Google Scholar 

  18. N. Tessler, G.J. Denton, R.H. Friend, Nature 382, 695 (1996)

    Article  CAS  Google Scholar 

  19. S. Welter, K. Brunner, J.W. Hofstraat, L. De Cola, Nature 421, 54 (2003)

    Article  CAS  Google Scholar 

  20. D.A. Tomalia, Prog. Polym. Sci. 30, 294 (2005)

    Article  CAS  Google Scholar 

  21. A.W. Bosman, H.M. Janssen, E.W. Meijer, Chem. Rev. 99, 1665 (1999)

    Article  CAS  Google Scholar 

  22. M. Fischer, F. Vögtle, Angew. Chem., Int. Ed. 38, 884 (1999)

    Article  Google Scholar 

  23. D.A. Tomalia, A.M. Naylor, W.A. Goddard III, Angew. Chem., Int. Ed. Engl 29, 138 (1990)

    Article  Google Scholar 

  24. S.C. Lo, P.L. Burn, Chem. Rev. 107, 1097 (2007)

    Article  CAS  Google Scholar 

  25. M. Thelakkat, Macromol. Mater. Eng. 287, 442 (2002)

    Article  CAS  Google Scholar 

  26. J. Bettenhausen, P. Strohriegl, Adv. Mater. 8, 507 (1996)

    Article  CAS  Google Scholar 

  27. N. Tamoto, C. Adachi, K. Nagai, Chem. Mater. 9, 1077 (1997)

    Article  CAS  Google Scholar 

  28. J. Bettenhausen, P. Strohriegl, W. Brutting, H. Tokuhisa, T. Tsutsui, J. Appl. Phys. 82, 4957 (1997)

    Article  CAS  Google Scholar 

  29. J. Bettenhausen, M. Greczmiel, M. Jandke, P. Strohriegl, Synth. Met. 91, 223 (1997)

    Article  CAS  Google Scholar 

  30. M. Thelakkat, H.W. Schmidt, Adv. Mater. 10, 219 (1998)

    Article  CAS  Google Scholar 

  31. M. Halim, J.N.G. Pillow, I.D.W. Samuel, P.L. Burn, Adv. Mater. 11, 371 (1999)

    Article  CAS  Google Scholar 

  32. Y. Sakamoto, T. Suzuki, A. Miura, H. Fujikawa, S. Tokito, Y. Taga, J. Am. Chem. Soc. 122, 1832 (2000)

    Article  CAS  Google Scholar 

  33. J.M. Lupton, L.R. Hemingway, I.D.W. Samuel, P.L. Burn, J. Mater. Chem. 10, 867 (2000)

    Article  CAS  Google Scholar 

  34. H.C. Yeh, R.H. Lee, L.H. Chan, T.Y.J. Lin, C.T. Chen, E. Balasubramaniam, Y.T. Tao, Chem. Mater. 13, 2788 (2001)

    Article  CAS  Google Scholar 

  35. J.M. Lupton, I.D.W. Samuel, R. Beavington, P.L. Burn, H. Bässler, Adv. Mater. 13, 258 (2001)

    Article  CAS  Google Scholar 

  36. D. Ma, J.M. Lupton, I.D.W. Samuel, S.C. Lo, P.L. Burn, Appl. Phys. Lett. 81, 2285 (2002)

    Article  CAS  Google Scholar 

  37. T.W. Kwon, M.M. Alam, S.A. Jenekhe, Chem. Mater. 16, 4657 (2004)

    Article  CAS  Google Scholar 

  38. X.Y. Cao, X.H. Liu, X.H. Zhou, Y. Zhang, Y. Jiang, Y. Cao, Y.X. Cui, J. Pei, J. Org. Chem. 69, 6050 (2004)

    Article  CAS  Google Scholar 

  39. D. Ma, Y. Hu, Y. Zhang, L. Wang, X. Jing, F. Wang, J.M. Lupton, I.D.W. Samuel, S. Lo, P.L. Burn, Synth. Met. 137, 1125 (2003)

    Article  CAS  Google Scholar 

  40. A. Nantalaksakul, D.R. Reddy, C.J. Bardeen, S. Thayumanavan, Photosynth. Res. 87, 133 (2006)

    Article  CAS  Google Scholar 

  41. A.W. Freeman, S.C. Koene, P.R.L. Malenfant, M.E. Thompson, J.M.J. Fréchet, J. Am. Chem. Soc. 122, 12385 (2000)

    Article  CAS  Google Scholar 

  42. S. Setayesh, A.C. Grimsdale, T. Weil, V. Enkelmann, K. Müllen, F. Meghdadi, E.J.W. List, G. Leising, J. Am. Chem. Soc. 123, 946 (2001)

    Article  CAS  Google Scholar 

  43. C.C. Kwok, M.S. Wong, Macromolecules 34, 6821 (2001)

    Article  CAS  Google Scholar 

  44. A. Pogantsch, F.P. Wenzl, E.J.W. List, G. Leising, A.C. Grimsdale, K. Müllen, Adv. Mater. 14, 1061 (2002)

    Article  CAS  Google Scholar 

  45. P. Du, W.H. Zhu, Y.Q. Xie, F. Zhao, C.F. Ku, Y. Cao, C.P. Chang, H. Tian, Macromolecules 37, 4378 (2004)

    Google Scholar 

  46. J.P.J. Markham, S.C. Lo, S.W. Magennis, P.L. Burn, I.D.W. Samuel, Appl. Phys. Lett. 80, 2645 (2002)

    Article  CAS  Google Scholar 

  47. S.C. Lo, N.A.H. Male, J.P.J. Markham, S.W. Magennis, P.L. Burn, O.V. Salata, D.W. Samuel, Adv. Mater. 14, 975 (2002)

    CAS  Google Scholar 

  48. S.C. Lo, E.B. Namdas, P.L. Burn, I.D.W. Samuel, Macromolecules 36, 9721 (2003)

    Article  CAS  Google Scholar 

  49. T.D. Anthopoulos, M.J. Frampton, E.B. Namdas, P.L. Burn, I.D.W. Samuel, Adv. Mater. 16, 557 (2004)

    Article  CAS  Google Scholar 

  50. J.P.J. Markham, E.B. Namdas, T.D. Anthopoulos, I.D.W. Samuel, G.J. Richards, P.L. Burn, Appl. Phys. Lett. 85, 1463 (2004)

    Article  CAS  Google Scholar 

  51. M.J. Frampton, E.B. Namdas, S.C. Lo, P.L. Burn, I.D.W. Samuel, J. Mater. Chem. 14, 2881 (2004)

    Article  CAS  Google Scholar 

  52. N.D. McClenaghan, R. Passalacqua, F. Loiseau, S. Campagna, B. Verheyde, A. Hameurlaine, W. Dehaen, J. Am. Chem. Soc. 125, 5356 (2003)

    Article  Google Scholar 

  53. F. Loiseau, S. Campagna, A. Hameurlaine, W. Dehaen, J. Am. Chem. Soc. 127, 11352 (2005)

    Article  CAS  Google Scholar 

  54. T.H. Xu, R. Lu, X.P. Qiu, X.L. Liu, P.C. Xue, C.H. Tan, C.Y. Bao, Y.Y. Zhao, Eur. J. Org. Chem. 2006, 4014 (2006)

    Article  Google Scholar 

  55. T. Konno, M.E. El-Khouly, Y. Nakamura, K. Kinoshita, Y. Araki, O. Ito, T. Yoshihara, S. Tobita, J. Nishimura, J. Phys. Chem. C 112, 1244 (2008)

    Article  CAS  Google Scholar 

  56. J. Lu, P.F. Xia, P.K. Lo, Y. Tao, M.S. Wong, Chem. Mater. 18, 6194 (2006)

    Article  CAS  Google Scholar 

  57. K.T. Wong, Y.H. Lin, H.H. Wu, F. Fungo, Org. Lett. 9, 4531 (2007)

    Article  CAS  Google Scholar 

  58. K. Albrecht, K. Yamamoto, J. Photopoly. Sci. Technol. 19, 175 (2006)

    Article  CAS  Google Scholar 

  59. K. Yamamoto, M. Higuchi, S. Shiki, M. Tsuruta, H. Chiba, Nature 415, 509 (2002)

    Article  CAS  Google Scholar 

  60. M. Higuchi, S. Shiki, K. Ariga, K. Yamamoto, J. Am. Chem. Soc. 123, 4414 (2001)

    Article  CAS  Google Scholar 

  61. K. Yamamoto, T. Imaoka, Bull. Chem. Soc. Jpn. 79, 511 (2006)

    Article  CAS  Google Scholar 

  62. K. Albrecht, Y. Kasai, A. Kimoto, K. Yamamoto, Macromolecules 41, 3793 (2008)

    Article  CAS  Google Scholar 

  63. A. Kimoto, J.S. Cho, M. Higuchi, K. Yamamoto, Macromolecules 37, 5531 (2004)

    Article  CAS  Google Scholar 

  64. A. Kimoto, J.S. Cho, M. Higuchi, K. Yamamoto, Macromol. Symp. 209, 51 (2004)

    Article  CAS  Google Scholar 

  65. A. Kimoto, J.S. Cho, K. Ito, D. Aoki, T. Miyake, K. Yamamoto, Macromol. Rapid Commun. 26, 597 (2005)

    Article  CAS  Google Scholar 

  66. Q. Zhang, Y.F. Hu, Y.X. Cheng, G.P. Su, D.G. Ma, L.X. Wang, X.B. Jing, F.S. Wang, Synth. Met. 137, 1111 (2003)

    Article  CAS  Google Scholar 

  67. J. Ding, J. Gao, Y. Cheng, Z. Xie, L. Wang, D. Ma, X. Jing, F. Wang, dv. Funct. Mater. 16, 575 (2006)

    Article  CAS  Google Scholar 

  68. M.H. Tsai, Y.H. Hong, C.H. Chang, H.C. Su, C.C. Wu, A. Matoliukstyte, J. Simokaitiene, S. Grigalevicius, J.V. Grazulevicius, C.P. Hsu, Adv. Mater. 19, 862 (2007)

    Article  CAS  Google Scholar 

  69. J.S. Cho, K. Takanashi, M. Higuchi, K. Yamamoto, Synth. Met. 150, 79 (2005)

    Article  CAS  Google Scholar 

  70. N. Satoh, J.S. Cho, M. Higuchi, K. Yamamoto, J. Am. Chem. Soc. 125, 8104 (2003)

    Article  CAS  Google Scholar 

  71. K. Albrecht, A. Kimoto, J.S. Cho, Y. Matsuura, K. Yamamoto, J. Photopolym. Sci. Technol. 21, 181 (2008)

    Article  CAS  Google Scholar 

  72. A. Kimoto, K. Masachika, J.S. Cho, M. Higuchi, K. Yamamoto, Chem. Mater. 16, 5706 (2004)

    Article  CAS  Google Scholar 

  73. T. Imaoka, R. Tanaka, S. Arimoto, M. Sakai, M. Fujii, K. Yamamoto, J. Am. Chem. Soc. 127, 13896 (2005)

    Article  CAS  Google Scholar 

  74. S. Campagna, S. Serroni, F. Puntoriero, C. Di Pietro, V. Ricevuto, in Electron Transfer in Chemistry, vol. 5, ed. by V. Balzani (Wiley-VCH, Weinheim, 2001)

    Google Scholar 

  75. S.K. Lower, M.A. El-Sayed, Chem. Rev. 66, 199 (1966)

    Article  CAS  Google Scholar 

  76. M.A. El-Sayed, J. Chem. Phys. 36, 573 (1962)

    Article  CAS  Google Scholar 

  77. M.A. El-Sayed, J. Chem. Phys. 38, 2834 (1963)

    Article  CAS  Google Scholar 

  78. S. Speiser, Chem. Rev. 96, 1953 (1996)

    Article  CAS  Google Scholar 

  79. T.H. Förster, Discuss. Faraday Soc. 27, 7 (1959)

    Article  Google Scholar 

  80. D.L. Dexter, J. Chem. Phys. 21, 836 (1953)

    Article  CAS  Google Scholar 

  81. L. De Cola, P. Belser, in Electron Transfer in Chemistry, vol. 5, ed. by V. Balzani (Wiley-VCH, Weinheim, 2001)

    Google Scholar 

  82. 3D model of ZnPG2-2 was optimized by a MOPAC (MM-AM1) calculation with the CAChe Worksystem ver. 5.04 (Fujitsu)

Download references

Acknowledgement

This work was partially supported by Grants-in-Aid for Scientific Research (Nos. 19205020, 19022034), the Core Research for Evolution Science and Technology (CREST) program of the Japan Science and Technology (JST) Agency, and Global COE program “High-Level Global Cooperation for Leading-Edge Platform on Access Space (C12)”.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Kimihisa Yamamoto.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Albrecht, K., Kasai, Y. & Yamamoto, K. The Fluorescence and Electroluminescence Properties of the Carbazole–Phenylazomethine Double Layer-Type Dendrimer. J Inorg Organomet Polym 19, 118–123 (2009). https://doi.org/10.1007/s10904-008-9239-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10904-008-9239-3

Keywords

Navigation