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Use of a Multiple Hydride Donor To Achieve an n-Doped Polymer with High Solvent Resistance

Journal Article · · ACS Applied Materials and Interfaces
 [1];  [2];  [3];  [4];  [5];  [2];  [6];  [7];  [3];  [5];  [6]
  1. Georgia Institute of Technology, Atlanta, GA (United States); University of Colorado, Boulder, CO (United States); SLAC
  2. Humboldt University of Berlin (Germany)
  3. Peking University, Beijing (China)
  4. SLAC National Accelerator Lab., Menlo Park, CA (United States); Stanford University, CA (United States)
  5. Humboldt University of Berlin (Germany); Helmholtz-Zentrum Berlin für Materialien und Energie GmbH, Berlin (Germany)
  6. Georgia Institute of Technology, Atlanta, GA (United States); University of Colorado, Boulder, CO (United States)
  7. University of Colorado, Boulder, CO (United States)
+ Show Author Affiliations

We report the ability to insolubilize doped semiconducting polymer layers can help enable the fabrication of efficient multilayer solution-processed electronic and optoelectronic devices. Here, we present a promising approach to simultaneously n-dope and largely insolubilize conjugated polymer films using tetrakis[{4-(1,3-dimethyl-2,3-dihydro-1H-benzo[d]imidazol-2-yl)phenoxy}methyl]methane (tetrakis-O-DMBI-H), which consists of four 2,3-dihydro-1H-benzoimidazole (DMBI-H) n-dopant moieties covalently linked to one another. Doping a thiophene-fused benzodifurandione-based oligo(p-phenylenevinylene)-co-thiophene polymer (TBDOPV-T) with tetrakis-O-DMBI-H results in a highly n-doped film with bulk conductivity of 15 S cm–1. Optical absorption spectra provide evidence for film retention of ~93% after immersion in o-dichlorobenzene for 5 min. The optical absorption signature of the charge carriers in the n-doped polymer decreases only slightly more than that of the neutral polymer under these conditions, indicating that the exposure to solvent also results in negligible dedoping of the film. Moreover, thermal treatment studies on a tetrakis-O-DMBI-H-doped TBDOPV-T film in contact with another undoped polymer film indicate immobilization of the molecular dopant in TBDOPV-T. This is attributed to the multiple electrostatic interactions between each dopant tetracation and up to four nearby anionic doped polymer segments.

Research Organization:
SLAC National Accelerator Laboratory (SLAC), Menlo Park, CA (United States)
Sponsoring Organization:
USDOE Office of Science (SC); German Research Foundation (DFG); National Science Foundation (NSF); U.S. Air Force of Scientific Research
Grant/Contract Number:
AC02-76SF00515
OSTI ID:
1884813
Journal Information:
ACS Applied Materials and Interfaces, Journal Name: ACS Applied Materials and Interfaces Journal Issue: 29 Vol. 14; ISSN 1944-8244
Publisher:
American Chemical Society (ACS)Copyright Statement
Country of Publication:
United States
Language:
English

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Related Subjects

36 MATERIALS SCIENCE
conductivity
cross-linking
donor
hydride
insolubilization
n-doping