Introducing Solubility Control for Improved Organic P-Type Dopants

Li, Jun; Zhang, Guangwu; Holm, Daniella M.; Jacobs, Ian E.; Yin, Bin; Stroeve, Pieter; Mascal, Mark; Moulé, Adam J.

doi:10.1021/acs.chemmater.5b02340

Introducing Solubility Control for Improved Organic P-Type Dopants

Journal Article · Fri Jul 24 00:00:00 EDT 2015 · Chemistry of Materials

DOI:https://doi.org/10.1021/acs.chemmater.5b02340· OSTI ID:1924290

Li, Jun ^[1]; Zhang, Guangwu ^[2]; Holm, Daniella M. ^[2]; Jacobs, Ian E. ^[2]; Yin, Bin ^[2]; Stroeve, Pieter ^[2]; Mascal, Mark ^[2]; ^[2]

Univ. of California, Davis, CA (United States); University of California-Davis
Univ. of California, Davis, CA (United States)

To overcome the poor solubility of the widely used p-type dopant 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), we have synthesized a series of structure-modified, organic p-type dopants to include alkyl ester groups designed to enable solubility and miscibility control. UV–vis–NIR and cyclic voltammetry measurements show increased solubility of mono- and diester substituted dopants with only modest changes to acceptor strength. Using absorption spectroscopy, photoluminescence, and in-plane conductivity measurements, we demonstrate that the new dopants can successfully p-type dope poly(3-hexylthiophene- 2,5-diyl) (P3HT). Monoester substituted dopants are characterized by only slightly reduced electron affinity relative to F4TCNQ, but greater doping effectiveness due to increased miscibility with P3HT. Diester substituted dopants undergo a dimerization reaction before assuming their doped states, which may help anchor dopants into position post deposition, thus decreasing the negative effect of dopant drift and diffusion. Here, we conclude that increased dopant solubility/miscibility increases the overall effectiveness of doping in solution-cast polymer films and that ester modification is a practical approach to achieving solubility/miscibility control in TCNQ-type dopants.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of California, Davis, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Materials Sciences & Engineering Division

Grant/Contract Number:: SC0010419

OSTI ID:: 1924290

Journal Information:: Chemistry of Materials, Journal Name: Chemistry of Materials Journal Issue: 16 Vol. 27; ISSN 0897-4756

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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