Title: Quantitative Dedoping of Conductive Polymers

Abstract

Although doping is a cornerstone of the inorganic semiconductor industry, most devices using organic semiconductors (OSCs) make use of intrinsic (undoped) materials. Recent work on OSC doping has focused on the use of dopants to modify a material’s physical properties, such as solubility, in addition to electronic and optical properties. However, if these effects are to be exploited in device manufacturing, a method for dedoping organic semiconductors is required. In this work, we outline two chemical strategies for dedoping OSC films. In the first strategy, we use an electron donor (a tertiary amine) to act as competitive donor. This process is based on a thermodynamic equilibrium between ionization of the donor and OSC and results in only partial dedoping. In the second strategy, we use an electron donor that subsequently reacts with the p-type dopant to create a nondoping product molecule. Primary and secondary amines undergo a rapid addition reaction with the dopant molecule 2,3,5,6-tetrafluoro-7,7,8,8,-tetracyanoquinodimethane (F4TCNQ), with primary amines undergoing a further reaction eliminating HCN. Under optimized conditions, films of semiconducting polymer poly(3-hexylthiophene) (P3HT) dedoped with 1-propylamine (PA) reach as-cast fluorescence intensities within 5 s of exposure to the amine, eventually reaching 140% of the as-cast values. Field-effect mobilities similarlymore » recover after dedoping. Quantitative fluorescence recovery is possible even in highly fluorescent polymers such as PFB, which are expected to be much more sensitive to residual dopants. Interestingly, treatment of undoped films with PA also yields increased fluorescence intensity and a reduction in conductivity of at least 2 orders of magnitude. These results indicate that the process quantitatively removes not only F4TCNQ but also intrinsic p-type impurities present in as-cast films. The dedoping strategies outlined in this article are generally applicable to other p- and n-type molecular dopants in OSC films.« less

Authors:

Jacobs, Ian E.  ^[1];

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Wang, Faustine ^[1]; Hafezi, Nema ^[1]; Medina-Plaza, Cristina ^[2]; Harrelson, Thomas F. ^[1]; Li, Jun ^[1]; Augustine, Matthew P. ^[1]; Mascal, Mark ^[1]; Moulé, Adam J. ^[1]

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+ Show Author Affiliations

1. Univ. of California, Davis, CA (United States)
2. Univ. of California, Davis, CA (United States); Univ. of Valladolid (Spain)

Publication Date:

Fri Dec 30 00:00:00 EST 2016

Research Org.:

Univ. of California, Davis, CA (United States)

Sponsoring Org.:

USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Materials Sciences & Engineering Division

OSTI Identifier:

1534452

Grant/Contract Number:  

SC0010419

Resource Type:

Accepted Manuscript

Journal Name:

Chemistry of Materials

Additional Journal Information:

Journal Volume: 29; Journal Issue: 2; Journal ID: ISSN 0897-4756

Publisher:

American Chemical Society (ACS)

Country of Publication:

United States

Language:

English

Subject:

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 36 MATERIALS SCIENCE; Impurities; Amines; Organic polymers; Fluorescence; Doping