DOI: 10.1002/pola.23019. Synthesis and electroluminescent properties of fluorene‐based copolymers containing electron‐withdrawing thiazole derivatives

Synthesis and electroluminescent properties of fluorene‐based copolymers containing electron‐withdrawing thiazole derivatives

10.1002/pola.23019

Crossref journal-article

Wiley

Journal of Polymer Science Part A: Polymer Chemistry (311)

Abstract

AbstractWe synthesized two fluorene‐based copolymers poly[(2,5‐bis(4‐hexylthiophen‐2‐yl)thiazolo[5,4‐day]thiazole‐5,5′‐diyl)‐alt‐(9,9′‐dioctylfluorene‐2,7‐diyl)] (PF‐TTZT), and poly[(5,5′‐bis(4‐hexylthiophen‐2‐yl)‐2,2′‐bithiazole‐5,5′‐diyl)‐alt‐(9,9′‐dioctylfluorene‐2,7‐diyl)] (PF‐TBTT), which contain the electron‐withdrawing moieties, thiazolothiazole, and bithiazole, respectively. Through electrochemical studies, we found that these two polymers exhibit stable reversible oxidation and reduction behaviors. Moreover, the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels of PF‐TBTT are lower than those of PF‐TTZT, and the bandgap of PF‐TBTT is smaller than that of PF‐TTZT. Thus the bithiazole moiety in PF‐TBTT is more electron‐withdrawing than the thiazolothiazole moiety in PF‐TTZT. Light‐emitting devices with indium tin oxide (ITO)/poly(3,4‐ethylene dioxythiophene):poly(styrenesulfonate)(PEDOT)/polymer/bis(2‐methyl‐8‐quinolinato)‐4‐phenylphenolate aluminum (BAlq)/LiF/Al configurations were fabricated. The performance of the PF‐TBTT device was found to be almost three times better than that of the PF‐TTZT device, which is because electron injection from the cathode to PF‐TBTT is much easier than for PF‐TTZT. We also investigated the planarity and frontier orbitals of the electron donor‐acceptor (D‐A) moieties with computational calculations using ab initio Hartree–Fock with the split‐valence 6‐31G* basis set. These calculations show that TBTT has a more nonplanar structure than TTZT and that the bithiazole moiety is more electron‐withdrawing than thiazolothiazole. These calculations are in good agreement with the experimental results. © Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 7148–7161, 2008

Bibliography

Jung, I. H., Jung, Y. K., Lee, J., Park, J., Woo, H. Y., Lee, J., Chu, H. Y., & Shim, H. (2008). Synthesis and electroluminescent properties of fluoreneâbased copolymers containing electronâwithdrawing thiazole derivatives. Journal of Polymer Science Part A: Polymer Chemistry, 46(21), 7148â7161. Portico.

Authors 8

In Hwan Jung (first)
Young Kwan Jung (additional)
Jonghee Lee (additional)
Jong‐Hwa Park (additional)
Han Young Woo (additional)
Jeong‐Ik Lee (additional)
Hye Yong Chu (additional)
Hong‐Ku Shim (additional)

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Dates

Type	When
Created	16 years, 11 months ago (Sept. 25, 2008, 6:19 p.m.)
Deposited	2 years ago (Sept. 2, 2023, 6:02 a.m.)
Indexed	1 year, 10 months ago (Oct. 17, 2023, 1:26 a.m.)
Issued	16 years, 11 months ago (Sept. 25, 2008)
Published	16 years, 11 months ago (Sept. 25, 2008)
Published Online	16 years, 11 months ago (Sept. 25, 2008)
Published Print	16 years, 10 months ago (Nov. 1, 2008)

Funders 0

None

BibTeX

@article{Jung_2008, title={Synthesis and electroluminescent properties of fluorene‐based copolymers containing electron‐withdrawing thiazole derivatives}, volume={46}, ISSN={1099-0518}, url={http://dx.doi.org/10.1002/pola.23019}, DOI={10.1002/pola.23019}, number={21}, journal={Journal of Polymer Science Part A: Polymer Chemistry}, publisher={Wiley}, author={Jung, In Hwan and Jung, Young Kwan and Lee, Jonghee and Park, Jong‐Hwa and Woo, Han Young and Lee, Jeong‐Ik and Chu, Hye Yong and Shim, Hong‐Ku}, year={2008}, month=sep, pages={7148–7161} }

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