DOI: 10.1063/1.1583872. Pyronin B as a donor for <i>n</i>-type doping of organic thin films

Pyronin B as a donor for n-type doping of organic thin films

10.1063/1.1583872

Crossref journal-article

AIP Publishing

Applied Physics Letters (317)

Abstract

We present an approach to stable n-type doping of organic matrices using organic dopands. To circumvent stability limitations inherent in strong organic donors, we produce the donor from a stable precursor compound in situ. As an example, pyronin B chloride is studied as a dopant in a 1,4,5,8-naphthalene tetracarboxylic dianhydride matrix. Conductivities up to 2×10−4 S/cm are obtained, which is two orders of magnitude higher than obtained previously using bis(ethylenedithio)-tetrathiafulvalene as a dopant [A. Nollau, M. Pfeiffer, T. Fritz, and K. Leo, J. Appl. Phys. 87, 4340 (2000)]. Field-effect measurements are used to prove n-type conduction. Other matrices which can be doped are N,N′-dimethyl-perylene-3,4,9,10-tetracarboxylic diimide and fullerene C60, frequently used in organic solar cells. Visible light and Fourier-transform infrared spectroscopy confirm the donor properties of pyronin B.

Bibliography

Werner, A. G., Li, F., Harada, K., Pfeiffer, M., Fritz, T., & Leo, K. (2003). Pyronin B as a donor for n-type doping of organic thin films. Applied Physics Letters, 82(25), 4495â4497.

Authors 6

A. G. Werner (first)
F. Li (additional)
K. Harada (additional)
M. Pfeiffer (additional)
T. Fritz (additional)
K. Leo (additional)

References 19 Referenced 123

10.1103/PhysRevB.64.195208 / Phys. Rev. B (2001)
10.1016/S1566-1199(01)00016-7 / Org. Electr. (2001)
10.1063/1.122612 / Appl. Phys. Lett. (1998)
10.1063/1.1432110 / Appl. Phys. Lett. (2002)
10.1063/1.1496502 / Appl. Phys. Lett. (2002)
10.1002/1521-4095(20021118)14:22<1633::AID-ADMA1633>3.0.CO;2-# / Adv. Mater. (2002)
{'key': '2024020400463125700_r7'}
10.1063/1.1359161 / J. Appl. Phys. (2001)
10.1063/1.373413 / J. Appl. Phys. (2000)
10.1063/1.120330 / Appl. Phys. Lett. (1997)
{'key': '2024020400463125700_r11'}
10.1063/1.337151 / J. Appl. Phys. (1986)
10.1002/(SICI)1521-4095(199803)10:5<365::AID-ADMA365>3.0.CO;2-U / Adv. Mater. (1998)
10.1021/ja962461j / J. Am. Chem. Soc. (1996)
10.1021/ja00876a029 / J. Am. Chem. Soc. (1962)
10.1021/ja00399a066 / J. Am. Chem. Soc. (1981)
10.1016/S0379-6779(00)01496-X / Synth. Met. (2001)
10.1016/S0927-0248(00)00022-2 / Sol. Energy Mater. Sol. Cells (2000)
{'key': '2024020400463125700_r19'}

Dates

Type	When
Created	22 years, 2 months ago (June 19, 2003, 6:21 p.m.)
Deposited	1 year, 7 months ago (Feb. 3, 2024, 7:46 p.m.)
Indexed	3 months ago (June 5, 2025, 4:26 a.m.)
Issued	22 years, 2 months ago (June 23, 2003)
Published	22 years, 2 months ago (June 23, 2003)
Published Print	22 years, 2 months ago (June 23, 2003)

Funders 0

None

BibTeX

@article{Werner_2003, title={Pyronin B as a donor for n-type doping of organic thin films}, volume={82}, ISSN={1077-3118}, url={http://dx.doi.org/10.1063/1.1583872}, DOI={10.1063/1.1583872}, number={25}, journal={Applied Physics Letters}, publisher={AIP Publishing}, author={Werner, A. G. and Li, F. and Harada, K. and Pfeiffer, M. and Fritz, T. and Leo, K.}, year={2003}, month=jun, pages={4495–4497} }

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