TY - JOUR
T1 - Can hydrogen bonds improve the hole-mobility in amorphous organic semiconductors? Experimental and theoretical insights
AU - Mimaite, Viktorija
AU - Grazulevicius, Juozas Vidas
AU - Laurinaviciute, Rasa
AU - Volyniuk, Dmytro
AU - Jankauskas, Vygintas
AU - Sini, Gjergji
N1 - KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: This work has been financially supported by the Taiwan–Latvia–Lithuania cooperation project “Synthesis and studies of organic electroactive materials for effective and reliable optoelectronic devices” (TAPLLT1/13). G.S. acknowledges the calculation centre of Cergy-Pontoise University for the computer time support, and V. Coropceanu and B. Kippelen (Georgia Tech', Atlanta, Georgia, USA), M. K. Ravva (KAUST, Saudi Arabia), and V. Cobut (Cergy-Pontoise University, France) for stimulating.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.
PY - 2015
Y1 - 2015
N2 - © The Royal Society of Chemistry 2015. Five hole-transporting triphenylamine derivatives containing methoxy and methyl groups are synthesized and investigated. The hole-mobility increases in the presence of methyl and methoxy substituents, exceeding 10-2 cm2 V-1 s-1 in the case of methyl groups. Quantum mechanical calculations on these compounds indicate very different dipole moments and intermolecular interaction strengths, with intriguing correlations with the trend in hole-mobility. Temperature dependent hole-mobility measurements indicate disorder dominated hole transport. The values of the energetic disorder parameter (σ) decrease upon methyl and methoxy substitutions despite the increase in dipole moments. This trend is discussed as a function of the interaction energy between adjacent molecules, the dipole moment, the molecular polarizability, and the conformational degree of freedom. Our results indicate that the global decrease of σ upon methyl and methoxy substitutions is dominated by the larger decrease in the geometrical randomness component of the energetic disorder. A direct correlation is established between the decrease in geometrical randomness and the increase in intermolecular interaction energies, mainly stemming from the additional C-H⋯π, O, N hydrogen bonds induced by methyl and methoxy groups.
AB - © The Royal Society of Chemistry 2015. Five hole-transporting triphenylamine derivatives containing methoxy and methyl groups are synthesized and investigated. The hole-mobility increases in the presence of methyl and methoxy substituents, exceeding 10-2 cm2 V-1 s-1 in the case of methyl groups. Quantum mechanical calculations on these compounds indicate very different dipole moments and intermolecular interaction strengths, with intriguing correlations with the trend in hole-mobility. Temperature dependent hole-mobility measurements indicate disorder dominated hole transport. The values of the energetic disorder parameter (σ) decrease upon methyl and methoxy substitutions despite the increase in dipole moments. This trend is discussed as a function of the interaction energy between adjacent molecules, the dipole moment, the molecular polarizability, and the conformational degree of freedom. Our results indicate that the global decrease of σ upon methyl and methoxy substitutions is dominated by the larger decrease in the geometrical randomness component of the energetic disorder. A direct correlation is established between the decrease in geometrical randomness and the increase in intermolecular interaction energies, mainly stemming from the additional C-H⋯π, O, N hydrogen bonds induced by methyl and methoxy groups.
UR - http://hdl.handle.net/10754/597718
UR - http://xlink.rsc.org/?DOI=C5TC02534F
UR - http://www.scopus.com/inward/record.url?scp=84946565391&partnerID=8YFLogxK
U2 - 10.1039/c5tc02534f
DO - 10.1039/c5tc02534f
M3 - Article
SN - 2050-7526
VL - 3
SP - 11660
EP - 11674
JO - J. Mater. Chem. C
JF - J. Mater. Chem. C
IS - 44
ER -