Search for: All records

We present a series of new dopants based on a bicyclcic guanidine-type structure, 1,5,7-triazabicyclo[4.4.0]dec-5-ene ( TBD ), for organic semiconductors. A series of TBD derivatives that were alkylated at the 7-position were synthesized and their physical properties were determined. These stable dopants were shown to be effective n-type dopants for [6,6]-phenyl- C 61 -butyric acid methyl ester (PC 61 BM), poly{[ N , N ′-bis(2-octyldodecyl)naphthalene-1,4,5,8-bis(dicarboximide)-2,6-diyl]- alt -5,5′-(2,2′-bithiophene)} (P(NDI2OD-T2)) and 3,9-bis(2-methylene-(3-(1,1-dicyanomethylene)-indanone))-5,5,11,11-tetrakis(4-hexylphenyl)-dithieno[2,3- d :2′,3′- d ′]- s -indaceno[1,2- b :5,6- b ′]dithiophene (ITIC). Films of PC 61 BM doped with 10 mol% of a dimeric derivative of TBD had electrical conductivities of 0.065 S cm −1 . The utility of the dopants was further shown by doping electron transport layers of PC 61 BM with 2TBD-C10 for methyl ammonium lead iodide (MAPbI 3 ) solar cells leading to improved fill factors and PCEs relative to undoped ETLs. 

The heterogeneous microstructure of semicrystalline polymers complicates the relationship between their electrical conductivity and carrier concentration. Charge transport models typically describe conductivity with an assumption of uniform doping throughout the material. Here, the evolution in morphology and optoelectronic properties of poly(3‐hexylthiophene) (P3HT) is reported as a function of carrier concentration in an organic electrochemical transistor using a polymeric ionic liquid (PIL) as the gate insulator.Operandograzing incidence X‐ray scattering reveals that negatively charged ions from the dielectric first infiltrate the amorphous regions of the semiconductor, and then penetrate the crystalline regions at a critical carrier density of 4 × 10²⁰cm⁻³. Upon infiltration, the crystallites expand by 12% in the alkyl stacking direction and compress by 4% in the π–π stacking direction. The change in crystal structure of P3HT correlates with a sharply increasing effective carrier mobility. UV–visible spectroscopy reveals that holes induced in P3HT first reside in the crystalline regions of the polymer, which verifies that a charge carrier need not be in the same physical domain as its associated counterion. The dopant‐induced morphological changes of P3HT rationalize the dependence of mobility on carrier concentration, suggesting a phase transition of crystalline regions at high carrier concentration.