Push–Pull Dyes for Yellow to NIR Emitting Electrochemical Cells

Maxime Rémond; Jongun Hwang; Jinbo Kim; Saeon Kim; Donghwan Kim; Christophe Bucher; Yann Bretonnière; Chantal Andraud; Eunkyoung Kim

doi:10.1002/adfm.202004831

Push–Pull Dyes for Yellow to NIR Emitting Electrochemical Cells

Maxime Rémond, Jongun Hwang, Jinbo Kim, Saeon Kim, Donghwan Kim, Christophe Bucher, Yann Bretonnière, Chantal Andraud, Eunkyoung Kim

Department of Chemical and Biomolecular Engineering

Research output: Contribution to journal › Article › peer-review

Abstract

Push–pull (D-π-A) dyes are explored for organic light-emitting electrochemical cells (LECs) taking advantages of their tunability in the intramolecular charge transfer (CT) through a π-bridge between donor and acceptor. These dyes present high thermal stability beyond 290 °C and fluorescence quantum yields (Φ_f), and simple thin film processability. The fluorene-based dyes with diphenylamine donor (DPF) show high tunability in electroluminescence wavelength up to 825 nm that corresponds to the most red-shifted metal-free LECs reported to date. The DPFs show high irradiance under a low working voltage in the presence of poly(9-vinylcarbazole) (PVK) and 2,5-bis(5-tert-butyl-benzoxazol-2-yl)thiophene (BBOT) hosts. As the CT distance of dyes is increased, V_on of the LECs is decreased, since Φ_f and lifetime of dyes are higher. Furthermore, the smaller angle between the π-bridge and acceptor (A_πA) of dye is critical to increase irradiance, for a closer dye–host proximity. Thus a DPF dye with the lowest A_πA (dye I) affords the highest irradiance of 425 µW cm⁻² (>220 Cd m⁻²) among the dyes in this study. Therefore push–pull dyes could provide a rational material design principle toward near-infrared emitting LECs.

Original language	English
Article number	2004831
Journal	Advanced Functional Materials
Volume	30
Issue number	50
DOIs	https://doi.org/10.1002/adfm.202004831
Publication status	Published - 2020 Dec 8

Bibliographical note

Funding Information:
This research was supported by a National Research Foundation (NRF) grant funded by Korean government (Ministry of Science, ICT & Future Planning, MSIP) through the Global Research Lab (GRL: 2016K1A1A2912753), Creative Materials Discovery Program (2018M3D1A1058536), and AOARD, Air Force Office of Scientific Research (AFOSR) under the Grant number FA9550‐19‐S‐0003.

Publisher Copyright:
© 2020 Wiley-VCH GmbH

All Science Journal Classification (ASJC) codes

Chemistry(all)
Materials Science(all)
Condensed Matter Physics

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@article{d84c6fcdca4243ab86270d4971c7802f,

title = "Push–Pull Dyes for Yellow to NIR Emitting Electrochemical Cells",

abstract = "Push–pull (D-π-A) dyes are explored for organic light-emitting electrochemical cells (LECs) taking advantages of their tunability in the intramolecular charge transfer (CT) through a π-bridge between donor and acceptor. These dyes present high thermal stability beyond 290 °C and fluorescence quantum yields (Φf), and simple thin film processability. The fluorene-based dyes with diphenylamine donor (DPF) show high tunability in electroluminescence wavelength up to 825 nm that corresponds to the most red-shifted metal-free LECs reported to date. The DPFs show high irradiance under a low working voltage in the presence of poly(9-vinylcarbazole) (PVK) and 2,5-bis(5-tert-butyl-benzoxazol-2-yl)thiophene (BBOT) hosts. As the CT distance of dyes is increased, Von of the LECs is decreased, since Φf and lifetime of dyes are higher. Furthermore, the smaller angle between the π-bridge and acceptor (AπA) of dye is critical to increase irradiance, for a closer dye–host proximity. Thus a DPF dye with the lowest AπA (dye I) affords the highest irradiance of 425 µW cm−2 (>220 Cd m−2) among the dyes in this study. Therefore push–pull dyes could provide a rational material design principle toward near-infrared emitting LECs.",

author = "Maxime R{\'e}mond and Jongun Hwang and Jinbo Kim and Saeon Kim and Donghwan Kim and Christophe Bucher and Yann Bretonni{\`e}re and Chantal Andraud and Eunkyoung Kim",

note = "Funding Information: This research was supported by a National Research Foundation (NRF) grant funded by Korean government (Ministry of Science, ICT & Future Planning, MSIP) through the Global Research Lab (GRL: 2016K1A1A2912753), Creative Materials Discovery Program (2018M3D1A1058536), and AOARD, Air Force Office of Scientific Research (AFOSR) under the Grant number FA9550‐19‐S‐0003. Publisher Copyright: {\textcopyright} 2020 Wiley-VCH GmbH",

year = "2020",

month = dec,

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doi = "10.1002/adfm.202004831",

language = "English",

volume = "30",

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AU - Rémond, Maxime

AU - Hwang, Jongun

AU - Kim, Jinbo

AU - Kim, Saeon

AU - Kim, Donghwan

AU - Bucher, Christophe

AU - Bretonnière, Yann

AU - Andraud, Chantal

AU - Kim, Eunkyoung

N1 - Funding Information: This research was supported by a National Research Foundation (NRF) grant funded by Korean government (Ministry of Science, ICT & Future Planning, MSIP) through the Global Research Lab (GRL: 2016K1A1A2912753), Creative Materials Discovery Program (2018M3D1A1058536), and AOARD, Air Force Office of Scientific Research (AFOSR) under the Grant number FA9550‐19‐S‐0003. Publisher Copyright: © 2020 Wiley-VCH GmbH

PY - 2020/12/8

Y1 - 2020/12/8

N2 - Push–pull (D-π-A) dyes are explored for organic light-emitting electrochemical cells (LECs) taking advantages of their tunability in the intramolecular charge transfer (CT) through a π-bridge between donor and acceptor. These dyes present high thermal stability beyond 290 °C and fluorescence quantum yields (Φf), and simple thin film processability. The fluorene-based dyes with diphenylamine donor (DPF) show high tunability in electroluminescence wavelength up to 825 nm that corresponds to the most red-shifted metal-free LECs reported to date. The DPFs show high irradiance under a low working voltage in the presence of poly(9-vinylcarbazole) (PVK) and 2,5-bis(5-tert-butyl-benzoxazol-2-yl)thiophene (BBOT) hosts. As the CT distance of dyes is increased, Von of the LECs is decreased, since Φf and lifetime of dyes are higher. Furthermore, the smaller angle between the π-bridge and acceptor (AπA) of dye is critical to increase irradiance, for a closer dye–host proximity. Thus a DPF dye with the lowest AπA (dye I) affords the highest irradiance of 425 µW cm−2 (>220 Cd m−2) among the dyes in this study. Therefore push–pull dyes could provide a rational material design principle toward near-infrared emitting LECs.

AB - Push–pull (D-π-A) dyes are explored for organic light-emitting electrochemical cells (LECs) taking advantages of their tunability in the intramolecular charge transfer (CT) through a π-bridge between donor and acceptor. These dyes present high thermal stability beyond 290 °C and fluorescence quantum yields (Φf), and simple thin film processability. The fluorene-based dyes with diphenylamine donor (DPF) show high tunability in electroluminescence wavelength up to 825 nm that corresponds to the most red-shifted metal-free LECs reported to date. The DPFs show high irradiance under a low working voltage in the presence of poly(9-vinylcarbazole) (PVK) and 2,5-bis(5-tert-butyl-benzoxazol-2-yl)thiophene (BBOT) hosts. As the CT distance of dyes is increased, Von of the LECs is decreased, since Φf and lifetime of dyes are higher. Furthermore, the smaller angle between the π-bridge and acceptor (AπA) of dye is critical to increase irradiance, for a closer dye–host proximity. Thus a DPF dye with the lowest AπA (dye I) affords the highest irradiance of 425 µW cm−2 (>220 Cd m−2) among the dyes in this study. Therefore push–pull dyes could provide a rational material design principle toward near-infrared emitting LECs.

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SN - 1616-301X

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ER -

Push–Pull Dyes for Yellow to NIR Emitting Electrochemical Cells

Abstract

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