TY - JOUR

T1 - Synthetic approach for the control of self-doping in luminescent organic semiconductors

AU - Kuimov, Anatoly D.

AU - Becker, Christina S.

AU - Shumilov, Nikita A.

AU - Koskin, Igor P.

AU - Sonina, Alina A.

AU - Komarov, Vladislav Yu

AU - Shundrina, Inna K.

AU - Kazantsev, Maxim S.

N1 - Funding Information: This work was supported by the RSF project 20-73-10090. The authors thank the XRD Facility of NIIC SB RAS for the data collection at 80K. Powder diffraction experiments were carried out at the Research and Education Centre of Novosibirsk State University REC-008. The assistance of Dr Evgeny Losev is gratefully acknowledged. The authors acknowledge the Multi-Access Chemical Service Center SB RAS for spectral and analytical measurements and Siberian Supercomputing Center SB RAS for supercomputing facilities. Publisher Copyright: © 2022 The Royal Society of Chemistry

PY - 2022/7/5

Y1 - 2022/7/5

N2 - Molecular doping of organic luminescent materials is an efficient tool to tune their optoelectronic properties. In particular, self-doping by luminescent longer-conjugation chain chemical by-products is a convenient way to obtain highly emissive organic semiconductors. Although the self-doping approach allows us to avoid the necessity of dopant synthesis, to realize the self-doping and optimize dopant concentration there is a need for a stepwise gradual purification of a material which may be problematic. Here we report a synthetic approach allowing us to control self-doping in luminescent organic semiconductors based on arylene-vinylene co-oligomers. We designed 1,2-bis(5-(4-octylphenyl)thiophen-2-yl)ethene (C8-BPTE) and synthesized it via two pathways yielding batches with different self-dopant concentrations. Our approach does not require a complex purification and excludes a possible degradation of the materials under sublimation or chromatography conditions. The optical properties of C8-BPTE crystals have been demonstrated to be finely tuned by simple mixing of synthesized batches of the material in a desired proportion, the increase of self-doped material content showed an increase in PL QY by up to 1.7 times and caused a red shift of photoluminescence spectra. Moreover, C8-BPTE demonstrated good film-formation ability and the substrate-inclined crystallization showed an efficient way to control crystal lateral size and its orientation on the substrate. C8-BPTE thin-film also demonstrated good p-type charge transport in solution-processed organic field-effect transistors with mobility of up to 0.1 cm2 V−1 s−1

AB - Molecular doping of organic luminescent materials is an efficient tool to tune their optoelectronic properties. In particular, self-doping by luminescent longer-conjugation chain chemical by-products is a convenient way to obtain highly emissive organic semiconductors. Although the self-doping approach allows us to avoid the necessity of dopant synthesis, to realize the self-doping and optimize dopant concentration there is a need for a stepwise gradual purification of a material which may be problematic. Here we report a synthetic approach allowing us to control self-doping in luminescent organic semiconductors based on arylene-vinylene co-oligomers. We designed 1,2-bis(5-(4-octylphenyl)thiophen-2-yl)ethene (C8-BPTE) and synthesized it via two pathways yielding batches with different self-dopant concentrations. Our approach does not require a complex purification and excludes a possible degradation of the materials under sublimation or chromatography conditions. The optical properties of C8-BPTE crystals have been demonstrated to be finely tuned by simple mixing of synthesized batches of the material in a desired proportion, the increase of self-doped material content showed an increase in PL QY by up to 1.7 times and caused a red shift of photoluminescence spectra. Moreover, C8-BPTE demonstrated good film-formation ability and the substrate-inclined crystallization showed an efficient way to control crystal lateral size and its orientation on the substrate. C8-BPTE thin-film also demonstrated good p-type charge transport in solution-processed organic field-effect transistors with mobility of up to 0.1 cm2 V−1 s−1

UR - http://www.scopus.com/inward/record.url?scp=85134829410&partnerID=8YFLogxK

U2 - 10.1039/d2qm00345g

DO - 10.1039/d2qm00345g

M3 - Article

AN - SCOPUS:85134829410

VL - 6

SP - 2244

EP - 2255

JO - Materials Chemistry Frontiers

JF - Materials Chemistry Frontiers

SN - 2052-1537

IS - 16

ER -