9 Parts-Per-Million-Level Doping Effects …
249
bulk-doped organic single crystals. In the future, organic single-crystal electronics
including the organic solar cells constructed on the doped organic single-crystal
substrates could be constructed.
Acknowledgements The authors thank M. Kubo, Y. Shinmura, C. Ohashi, and N. Ishiyama for
their important work on doping and Professors M. Izaki and H. Naito for their helpful discussions.
The authors also appreciate A. Adachi and S. Ohashi of Epitech Inc. for their help in the design and
construction of the built-in chamber globe box systems with extremely slow deposition apparatuses.
Funding from CREST/JST and NEDO is gratefully acknowledged.
References
1. Martin, M., Andre, J.J., Simon, J.: Influence of dioxygen on the junction properties of
metallophthalocyanine based devices. J. Appl. Phys. 54, 2792–2794 (1983)
2. Tada, H., Touda, H., Takada, M., Matsushige, K.: Quasi-intrinsic semiconducting state of
titanyl-phthalocyanine films obtained under ultrahigh vacuum conditions. Appl. Phys. Lett. 76,
873–875 (2000)
3. Hiramoto, M., Kishigami, Y., Yokoyama, M.: Doping effect on the two-layer organic solar cell.
Chem. Lett. 1990, 119–122 (1990)
4. Akamatsu, H., Inokuchi, H., Matsunaga, Y.: Electrical conductivity of the perylene–bromine
complex. Nature 173, 168–169 (1954)
5. Hiramoto, M., Ihara, K., Fukusumi, H., Yokoyama, M.: Conduction type control from n to p
type for organic pigment films purified by reactive sublimation. J. Appl. Phys. 78, 7153–7157
(1995)
6. Hiramoto, M., Ihara, K., Yokoyama, M.: Fermi level shift in photoconductive organic pigment
films measured by Kelvin vibrating capacitor method. Jpn. J. Appl. Phys. 34, 3803–3807 (1995)
7. Hiramoto, M.: Organic solar cells incorporating a p-i-n junction and a p-n homojunction. In:
Sun, S. -S., Sariciftci, N. S. (ed.) Organic photovoltaics, Mechanisms, Materials and Devices,
p. 268. CRC Press, New York (2005)
8. Huang, S.J., Pfeiffer, M., Werner, A., Blochwitz, J., Leo, K., Liu, Y.S.: Low-voltage organic
electroluminescent devices using pin structures. Appl. Phys. Lett. 80, 139–141 (2002)
9. Blochwitz, J., Pfeiffer, M., Fritz, T., Leo, K.: Low voltage organic light emitting diodes featuring
doped phthalocyanine as hole transport material. Appl. Phys. Lett. 73, 729–731 (1998)
10. Tietze, M.L., Pahner, P., Schmidt, K., Leo, K., Lüssem, B.: Doped organic semiconductors:
trap-filling, impurity saturation, and reserve regimes. Adv. Funct. Mater. 25, 2701–2707 (2015)
11. Koech, P.K., Padmaperuma, A.B., Wang, L., Swensen, J.S., Polikarpov, E.,
Darsell, J.T., Rainbolt, J.E., Gaspar, D.J.: Synthesis and application of 1,3,4,5,7,8hexafluorotetracyanonaphthoquinodimethane (F6-TNAP): A conductivity dopant for organic
light-emitting devices. Chem. Mater. 22, 3926–3932 (2010)
12. Cho, S.H., Pyo, S.W., Suh, M.C.: Low voltage top-emitting organic light emitting devices by
using 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile. Synth. Met. 162, 402–405 (2012)
13. Solomeshch, O., Yu, Y.J., Goryunkov, A.A., Sidorov, L.N., Tuktarov, R.F., Choi, D.H., Jin, J.
–ll., Tessler, N.: Ground-state interaction and electrical doping of fluorinated C 60 in conjugated
polymers. Adv. Mater. 21, 4456–4460 (2009)
14. Tokito, S., Noda, K., Taga, Y., J. Phys. D: Metal oxides as a hole-injecting layer for an organic
electroluminescent device. Appl. Phys. 29, 2750–2753 (1996)
15. Matsushima, T., Kinoshita, Y., Murata, H.: Formation of Ohmic hole injection by inserting an
ultrathin layer of molybdenum trioxide between indium tin oxide and organic hole-transporting
layers. Appl. Phys. Lett. 91, 253504 (3 pages) (2007)
249
bulk-doped organic single crystals. In the future, organic single-crystal electronics
including the organic solar cells constructed on the doped organic single-crystal
substrates could be constructed.
Acknowledgements The authors thank M. Kubo, Y. Shinmura, C. Ohashi, and N. Ishiyama for
their important work on doping and Professors M. Izaki and H. Naito for their helpful discussions.
The authors also appreciate A. Adachi and S. Ohashi of Epitech Inc. for their help in the design and
construction of the built-in chamber globe box systems with extremely slow deposition apparatuses.
Funding from CREST/JST and NEDO is gratefully acknowledged.
References
1. Martin, M., Andre, J.J., Simon, J.: Influence of dioxygen on the junction properties of
metallophthalocyanine based devices. J. Appl. Phys. 54, 2792–2794 (1983)
2. Tada, H., Touda, H., Takada, M., Matsushige, K.: Quasi-intrinsic semiconducting state of
titanyl-phthalocyanine films obtained under ultrahigh vacuum conditions. Appl. Phys. Lett. 76,
873–875 (2000)
3. Hiramoto, M., Kishigami, Y., Yokoyama, M.: Doping effect on the two-layer organic solar cell.
Chem. Lett. 1990, 119–122 (1990)
4. Akamatsu, H., Inokuchi, H., Matsunaga, Y.: Electrical conductivity of the perylene–bromine
complex. Nature 173, 168–169 (1954)
5. Hiramoto, M., Ihara, K., Fukusumi, H., Yokoyama, M.: Conduction type control from n to p
type for organic pigment films purified by reactive sublimation. J. Appl. Phys. 78, 7153–7157
(1995)
6. Hiramoto, M., Ihara, K., Yokoyama, M.: Fermi level shift in photoconductive organic pigment
films measured by Kelvin vibrating capacitor method. Jpn. J. Appl. Phys. 34, 3803–3807 (1995)
7. Hiramoto, M.: Organic solar cells incorporating a p-i-n junction and a p-n homojunction. In:
Sun, S. -S., Sariciftci, N. S. (ed.) Organic photovoltaics, Mechanisms, Materials and Devices,
p. 268. CRC Press, New York (2005)
8. Huang, S.J., Pfeiffer, M., Werner, A., Blochwitz, J., Leo, K., Liu, Y.S.: Low-voltage organic
electroluminescent devices using pin structures. Appl. Phys. Lett. 80, 139–141 (2002)
9. Blochwitz, J., Pfeiffer, M., Fritz, T., Leo, K.: Low voltage organic light emitting diodes featuring
doped phthalocyanine as hole transport material. Appl. Phys. Lett. 73, 729–731 (1998)
10. Tietze, M.L., Pahner, P., Schmidt, K., Leo, K., Lüssem, B.: Doped organic semiconductors:
trap-filling, impurity saturation, and reserve regimes. Adv. Funct. Mater. 25, 2701–2707 (2015)
11. Koech, P.K., Padmaperuma, A.B., Wang, L., Swensen, J.S., Polikarpov, E.,
Darsell, J.T., Rainbolt, J.E., Gaspar, D.J.: Synthesis and application of 1,3,4,5,7,8hexafluorotetracyanonaphthoquinodimethane (F6-TNAP): A conductivity dopant for organic
light-emitting devices. Chem. Mater. 22, 3926–3932 (2010)
12. Cho, S.H., Pyo, S.W., Suh, M.C.: Low voltage top-emitting organic light emitting devices by
using 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile. Synth. Met. 162, 402–405 (2012)
13. Solomeshch, O., Yu, Y.J., Goryunkov, A.A., Sidorov, L.N., Tuktarov, R.F., Choi, D.H., Jin, J.
–ll., Tessler, N.: Ground-state interaction and electrical doping of fluorinated C 60 in conjugated
polymers. Adv. Mater. 21, 4456–4460 (2009)
14. Tokito, S., Noda, K., Taga, Y., J. Phys. D: Metal oxides as a hole-injecting layer for an organic
electroluminescent device. Appl. Phys. 29, 2750–2753 (1996)
15. Matsushima, T., Kinoshita, Y., Murata, H.: Formation of Ohmic hole injection by inserting an
ultrathin layer of molybdenum trioxide between indium tin oxide and organic hole-transporting
layers. Appl. Phys. Lett. 91, 253504 (3 pages) (2007)