Fluorinated Thiophene-Phenylene Co-Oligomers for Optoelectronic Devices

Fluorinated Thiophene-Phenylene Co-Oligomers for Optoelectronic Devices Full article

Journal

ACS Applied Materials and Interfaces
ISSN: 1944-8244 , E-ISSN: 1944-8252

Output data

Year: 2020, Volume: 12, Number: 8, Pages: 9507-9519 Pages count : 13 DOI: 10.1021/acsami.9b20295

Tags

organic electronics; organic semiconductors; field-effect transistor; light-emitting transistor; crystal structure; charge transport; fluorination

Authors

Sosorev Andrey Yu ^1,3,4,5 , Trukhanov Vasiliy A. ^1,3,4 , Maslennikov Dmitry R. ^1,3,4,5 , Borshchev Oleg, V ¹ , Polyakov Roman A. ¹ , Skorotetcky Maxim S. ¹ , Surin Nikolay M. ¹ , Kazantsev Maxim S. ⁶ , Dominskiy Dmitry, I ^1,3,4 , Tafeenko Viktor A. ² , Ponomarenko Sergey A. ^1,2 , Paraschuk Dmitry Yu ^1,3,4

Affiliations

1	(Данные Web of science) Russian Acad Sci, Enikolopov Inst Synthet Polymer Mat, Moscow 117393, Russia
2	(Данные Web of science) Lomonosov Moscow State Univ, Dept Chem, Moscow 119991, Russia
3	(Данные Web of science) Lomonosov Moscow State Univ, Fac Phys, Moscow 119991, Russia
4	(Данные Web of science) Lomonosov Moscow State Univ, Int Laser Ctr, Moscow 119991, Russia
5	(Данные Web of science) Russian Acad Sci, Inst Spect, Moscow 108840, Russia
6	(Данные Web of science) NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia

Organic optoelectronics requires materials combining bright luminescence and efficient ambipolar charge transport. Thiophene-phenylene co-oligomers (TPCOs) are promising highly emissive materials with decent charge-carrier mobility; however, they typically show poor electron injection in devices, which is usually assigned to high energies of their lowest unoccupied molecular orbitals (LUMOs). A widely used approach to lower the frontier orbitals energy levels of a conjugated molecule is its fluorination. In this study, we synthesized three new fluorinated derivatives of one of the most popular TPCOs, 2,2'-(1,4-phenylene)bis[5-phenylthiophene] (PTPTP) and studied them by cyclic voltammetry, absorption, photoluminescence, and Raman spectroscopies. The obtained data reveal a positive effect of fluorination on the optoelectronic properties of PTPTP: LUMO levels are finely tuned, and photoluminescence quantum yield and absorbance are increased. We then grew crystals from fluorinated PTPTPs, resolved their structures, and showed that fluorination dramatically affects the packing motif and facilitates pi-stacking. Finally, we fabricated thin-film organic field-effect transistors (OFETs) and demonstrated a strong impact of fluorination on charge injection/transport for both types of charge carriers, namely, electrons and holes. Specifically, balanced ambipolar charge transport and electroluminescence were observed only in the OFET active channel based on the partially fluorinated PTPTP. The obtained results can be extended to other families of conjugated oligomers and highlight the efficiency of fluorination for rational design of organic semiconductors for optoelectronic devices.

Sosorev A.Y. , Trukhanov V.A. , Maslennikov D.R. , Borshchev O.V. , Polyakov R.A. , Skorotetcky M.S. , Surin N.M. , Kazantsev M.S. , Dominskiy D.I. , Tafeenko V.A. , Ponomarenko S.A. , Paraschuk D.Y.
Fluorinated Thiophene-Phenylene Co-Oligomers for Optoelectronic Devices
ACS Applied Materials and Interfaces. 2020. V.12. N8. P.9507-9519. DOI: 10.1021/acsami.9b20295 WOS Scopus РИНЦ

Published online:	Feb 3, 2020
Published print:	Feb 26, 2020

Web of science	WOS:000517360000057
Scopus	2-s2.0-85080997948
Elibrary	43257065
OpenAlex	W3005398707