Highly Red Emissive Conjugated Homopolymers Based on Double B←N Bridged Bipyridine Unit

Yu-Yue Gao; Kai-Yuan Zhang; Shu-Meng Wang; Hui Tong; Jun Liu

doi:10.1007/s10118-024-3123-7

Your Location：

Home >

Browse articles >

Highly Red Emissive Conjugated Homopolymers Based on Double B←N Bridged Bipyridine Unit

RESEARCH ARTICLE | Updated：2024-08-06

- Highly Red Emissive Conjugated Homopolymers Based on Double B←N Bridged Bipyridine Unit
- Chinese Journal of Polymer Science Vol. 42, Issue 8, Pages: 1029-1037(2024)
- Affiliations：
  
  a.State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
  b.School of Applied Chemistry and Engineering, University of Science and Technology of China, Hefei 230026, China
- Author bio：
  
  liujun@ciac.ac.cn
- Funds：
- DOI：10.1007/s10118-024-3123-7
  CLC：
- Received：28 January 2024，
  
  Revised：2024-03-09，
  
  Accepted：11 March 2024，
  
  Online First：25 April 2024，
  
  Published：01 August 2024
- Accepted：
Scan QR Code
Gao, Y. Y.; Zhang, K. Y.; Wang, S. M.; Tong, H.; Liu, J. Highly red emissive conjugated homopolymers based on double B←N bridged bipyridine unit. Chinese J. Polym. Sci. 2024, 42, 1029–1037

Yu-Yue Gao, Kai-Yuan Zhang, Shu-Meng Wang, et al. Highly Red Emissive Conjugated Homopolymers Based on Double B←N Bridged Bipyridine Unit[J]. Chinese Journal of Polymer Science, 2024, 42(8): 1029-1037.
Gao, Y. Y.; Zhang, K. Y.; Wang, S. M.; Tong, H.; Liu, J. Highly red emissive conjugated homopolymers based on double B←N bridged bipyridine unit. Chinese J. Polym. Sci. 2024, 42, 1029–1037 DOI： 10.1007/s10118-024-3123-7.

Yu-Yue Gao, Kai-Yuan Zhang, Shu-Meng Wang, et al. Highly Red Emissive Conjugated Homopolymers Based on Double B←N Bridged Bipyridine Unit[J]. Chinese Journal of Polymer Science, 2024, 42(8): 1029-1037. DOI： 10.1007/s10118-024-3123-7.

摘要

In this manuscript

a series of new organoboron conjugated homopolymers based on double B←N bridged bipyridine (BNBP) unit are designed and synthesized. All these polymers exhibit deep-red emission (

max

650 nm) with high fluorescence efficiency (

ca. 0.6) in solution. The polymers can be used as the emitters in solution processed OLEDs with decent device performance.

Abstract

Conjugated homopolymers based on six-member rings

e.g.

polyfluorene

always exhibit blue emission and conjugated homopolymers based on five-member rings

e.g.

polythiophene

can give red emission with low efficiency. In this work

we report a series of new conjugated homopolymers based on six-member r

ings with high-efficiency deep-red emission. The repeating units of the red light emitting homopolymers are double B←N bridged bipyridine (BNBP) with the boron atoms functionalized with diphenyl

borafluorene

and 2

7-di-

tert

-butyl-borafluorene groups

respectively. The relationship between the chemical structures and the opto-electronic properties of the monomers and the homopolymers has been systematically studied. The three polymers emit pure red light (

max

=656 nm) or deep red light (

max

=693 nm) with fluorescence quantum efficiency in solution higher than 60%. The polymers can be used as the emitters in solution-processed organic light-emitting diodes with red emission and decent device performance. This work indicates a new strategy to design highly efficient light emitting conjugated polymers.

关键词

Keywords

references

Burroughes, J. H.; Bradley, D. D. C.; Brown, A. R.; Marks, R. N.; Mackay, K.; Friend, R. H.; Burns, P. L.; Holmes, A. B. Light-emitting diodes based on conjugated polymers. Nature 1990 , 347 , 539−541..

Heeger, A. J. Semiconducting and metallic polymers: the fourth generation of polymeric materials (Nobel Lecture). Angew. Chem. Int. Ed. 2001 , 40 , 2591−2611..

Wang, Z. B.; Helander, M. G.; Qiu, J.; Puzzo, D. P.; Greiner, M. T.; Hudson, Z. M.; Wang, S.; Liu, Z. W.; Lu, Z. H. Unlocking the full potential of organic light-emitting diodes on flexible plastic. Nat. Photon. 2011 , 5 , 753−757..

Guo, X.; Baumgarten, M.; Müllen, K. Designing π -conjugated polymers for organic electronics. Prog. Polym. Sci. 2013 , 38 , 1832−1908..

Huang, W. Polymers for flexible electronics. Chinese J. Polym. Sci. 2022 , 40 , 1513−1514..

Murto, P.; Minotto, A.; Zampetti, A.; Xu, X.; Andersson, M. R.; Cacialli, F.; Wang, E. Triazolobenzothiadiazole-based copolymers for polymer light-emitting diodes: pure near-infrared emission via optimized energy and charge transfer. Adv. Opt. Mater. 2016 , 4 , 2068−2076..

Ostroverkhova, O. Organic optoelectronic materials: mechanisms and applications. Chem. Rev. 2016 , 116 , 13279−13412..

Tang, S.; Murto, P.; Xu, X.; Larsen, C.; Wang, E.; Edman, L. Intense and stable near-infrared emission from light-emitting electrochemical cells comprising a metal-free indacenodithieno[3,2- b ] thiophene-based copolymer as the single emitter. Chem. Mat. 2017 , 29 , 7750−7759..

Bai, L.; Sun, C.; Han, Y.; Wei, C.; An, X.; Sun, L.; Sun, N.; Yu, M.; Zhang, K.; Lin, J.; Xu, M.; Xie, L.; Ling, H.; Cabanillas-Gonzales, J.; Song, L.; Hao, X.; Huang, W. Steric poly(diarylfluorene-co-benzothiadiazole) for efficient amplified spontaneous emission and polymer light-emitting diodes: benefit from preventing interchain aggregation and polaron formation. Adv. Opt. Mater. 2020 , 8 , 1901616..

Liu, Y.; Hua, L.; Yan, S.; Ren, Z. Halogenated π -conjugated polymeric emitters with thermally activated delayed fluorescence for highly efficient polymer light emitting diodes. Nano Energy 2020 , 73 , 104800..

Gon, M.; Wakabayashi, J.; Nakamura, M.; Tanaka, K.; Chujo, Y. Controlling energy gaps of pi-conjugated polymers by multi-fluorinated boron-fused azobenzene acceptors for highly efficient near-infrared emission. Chem. Asian J. 2021 , 16 , 696−703..

Guo, X.; Zhang, Y.; Hu, Y.; Yang, J.; Li, Y.; Ni, Z.; Dong, H.; Hu, W. Molecular weight engineering in high-performance ambipolar emissive mesopolymers. Angew. Chem. Int. Ed. 2021 , 60 , 14902−14908..

Wang, T.; Zou, Y.; Huang, Z.; Li, N.; Miao, J.; Yang, C. Narrowband emissive TADF conjugated polymers towards highly efficient solution-processible OLEDs. Angew. Chem. Int. Ed. 2022 , 61 , e202211172..

Li, X.; Yan, L.; Liu, S.; Wang, S.; Rao, J.; Zhao, L.; Tian, H.; Ding, J.; Wang, L. Polymerized thermally activated delayed-fluorescence small molecules: long-axis polymerization leads to a nearly concentration-independent luminescence. Angew. Chem. Int. Ed. 2023 , 62 , e202300529..

Nakamura, M.; Gon, M.; Tanaka, K.; Chujo, Y. Solid-state near-infrared emission of π -conjugated polymers consisting of boron complexes with vertically projected steric substituents. Macromolecules 2023 , 56 , 2709−2718..

He, Z. W.; Zhang, Q.; Li, C. X.; Han, H. T.; Lu, Y. Synthesis of thieno[3,4- b ] pyrazine-based alternating conjugated polymers via direct arylation for near-infrared OLED applications. Chinese J. Polym. Sci. 2022 , 40 , 138−146..

Pei, Q.; Yang, Y. Efficient photoluminescence and electroluminescence from a soluble polyfluorene. J. Am. Chem. Soc. 1996 , 118 , 7416−7417..

Grell, M.; Bradley, D. D. C.; Ungar, G.; Hill, J.; Whitehead, K. S. Interplay of physical structure and photophysics for a liquid crystalline polyfluorene. Macromolecules 1999 , 32 , 5810−5817..

Bernius, M. T.; Inbasekaran, M.; O'Brien, J.; Wu, W. Progress with light-emitting polymers. Adv. Mater. 2000 , 12 , 1737−1750..

Leclerc, M. Polyfluorenes: twenty years of progress. J. Polym. Sci., Part A: Polym. Chem. 2001 , 39 , 2867−2873..

List, E. J. W.; Guentner, R.; Scanducci de Freitas, P.; Scherf, U. The effect of Keto defect sites on the emission properties of polyfluorene-type materials. Adv. Mater. 2002 , 14 , 374−378..

Wang, M.; Li, Y.; Xie, Z.; Wang, L. Polyfluorenes containing pyrazine units: synthesis, photophysics and electroluminescence. Sci. China Chem. 2011 , 54 , 656−665..

Sun, M. L.; Zhong, C. M.; Li, F.; Pei, Q. B. Purified polar polyfluorene for light-emitting diodes and light-emitting electrochemical cells. Chinese J. Polym. Sci. 2012 , 30 , 503−510..

Braun, D.; Gustafsson, G.; McBranch, D.; Heeger, A. J. Electroluminescence and electrical transport in poly(3-octylthiophene) diodes. J. Appl. Phys. 1992 , 72 , 564−568..

Ruseckas, A.; Namdas, E. B.; Theander, M.; Svensson, M.; Yartsev, A.; Zigmantas, D.; Andersson, M. R.; Inganäs, O.; Sundström, V. Luminescence quenching by inter-chain aggregates in substituted polythiophenes. J. Photochem. Photobiol. A-Chem. 2001 , 144 , 3−12..

Brown, P. J.; Thomas, D. S.; Köhler, A.; Wilson, J. S.; Kim, J.-S.; Ramsdale, C. M.; Sirringhaus, H.; Friend, R. H. Effect of interchain interactions on the absorption and emission of poly(3-hexylthiophene). Phys. Rev. B 2003 , 67 , 064203..

Barbarella, G.; Melucci, M.; Sotgiu, G. The versatile thiophene: an overview of recent research on thiophene-based materials. Adv. Mater. 2005 , 17 , 1581−1593..

Dou, C.; Long, X.; Ding, Z.; Xie, Z.; Liu, J.; Wang, L. An electron-deficient building block based on the B←N Unit: an electron acceptor for all-polymer solar cells. Angew. Chem. Int. Ed. 2016 , 55 , 1436−1440..

Long, X.; Ding, Z.; Dou, C.; Zhang, J.; Liu, J.;Wang, L. Polymer acceptor based on double B←N bridged bipyridine (BNBP) unit for high-efficiency all-polymer solar cells. Adv. Mater. 2016 , 28 , 6504−6508..

Zhang, Z.; Miao, J.; Ding, Z.; Kan, B.; Lin, B.; Wan, X.; Ma, W.; Chen, Y.; Long, X.; Dou, C.; Zhang, J.; Liu, J.; Wang, L. Efficient and thermally stable organic solar cells based on small molecule donor and polymer acceptor. Nat. Commun. 2019 , 10 , 3271..

Zhao, R.; Wang, N.; Yu, Y.; Liu, J. Organoboron polymer for 10% efficiency all-polymer solar cells. Chem. Mat. 2020 , 32 , 1308−1314..

Cao, X.; Li, H.; Hu, J.; Tian, H.; Han, Y.; Meng, B.; Liu, J.; Wang, L. An amorphous n-type conjugated polymer with an ultra-rigid planar backbone. Angew. Chem. Int. Ed. 2023 , 62 , e202212979..

Dong, C.; Deng, S.; Meng, B.; Liu, J.; Wang, L. A distannylated monomer of a strong electron-accepting organoboron building block: enabling acceptor-acceptor-type conjugated polymers for n-type thermoelectric applications. Angew. Chem. Int. Ed. 2021 , 60 , 16184−16190..

Wang, J.; Zhao, R.; Zhang, L.; Miao, J.; Liu, J.; Wang, L. A Direct surface modification strategy of ITO anodes enables high-performance organic photodetectors. J. Mater. Chem. C 2023 , 11 , 14421−14428..

Long, X.; Li, D.; Wang, B.; Jiang, Z.; Xu, W.; Wang, B.; Yang, D.; Xia, Y. Heterocyclization strategy for construction of linear conjugated polymers: efficient metal-free electrocatalysts for oxygen reduction. Angew. Chem. Int. Ed. 2019 , 58 , 11369−11373..

Hübner, A.; Diefenbach, M.; Bolte, M.; Lerner, H. W.; Holthausen, M. C.; Wagner, M. Confirmation of an early postulate: B-C-B two-electron-three-center bonding in organo(hydro)boranes. Angew. Chem. Int. Ed. 2012 , 51 , 12514−12518..

Müller, M.; Maichle-Mössmer, C.; Bettinger, H. F. BN-phenanthryne: cyclotetramerization of an 1,2-azaborine derivative. Angew. Chem. Int. Ed. 2014 , 53 , 9380−9383..

Liu, Q.; Yang, L.; Yao, C.; Geng, J.; Wu, Y.; Hu, X. Controlling the lewis acidity and polymerizing effectively prevent frustrated lewis pairs from deactivation in the hydrogenation of terminal alkynes. Org. Lett. 2021 , 23 , 3685−3690..

Müller, C. D.; Falcou, A.; Reckefuss, N.; Rojahn, M.; Wiederhirn, V.; Rudati, P.; Froh ne, H.; Nuyken, O.; Becker, H.; Meerholz, K. Multi-colour organic light-emitting displays by solution processing. Nature 2003 , 421 , 829−833..

Li, B.; Xu, X.; Sun, M.; Fu, Y.; Yu, G.; Liu, Y.; Bo, Z. Porphyrin-cored star polymers as efficient nondoped red light-emitting materials. Macromolecules 2006 , 39 , 456−461..

Qu, B.; Chen, Z.; Liu, Y.; Cao, H.; Xu, S.; Cao, S.; Lan, Z.; Wang, Z.; Gong, Q. Orange and red emitting OLEDs based on phenothiazine polymers. J. Phys. D: Appl. Phys. 2006 , 39 , 2680..

Gather, M. C.; Köhnen, A.; Falcou, A.; Becker, H.; Meerholz, K. Solution-processed full-color polymer organic light-emitting diode displays fabricated by direct photolithography. Adv. Funct. Mater. 2007 , 17 , 191−200..

Wang, T.; Li, K.; Yao, B.; Chen, Y.; Zhan, H.; Xie, Z.; Xie, G.; Yi, X.; Cheng, Y. Rigidity and polymerization amplified red thermally activated delayed fluorescence polymers for constructing red and single-emissive-layer white OLEDs. Adv. Funct. Mater. 2020 , 30 , 2002493..

Fan, Q.; Liu, Y.; Hao, Z.; Li, C.; Wang, Y.; Tan, H.; Zhu, W.; Cao, Y. Polymer light-emitting devices based on europium(III) complex with 11-bromo-dipyrido[3,2- a :2′,3′- c ] phenazine. Sci. China Chem. 2015 , 58 , 1152−1158..

Chen, L. L.; Peng, L.; Wang, L. Y.; Zhu, X. H.; Zou, J. H.; Peng, J. Molecular engineering of an electron-transport triarylphosphine oxide-triazine conjugate toward high-performance phosphorescent organic light-emitting diodes with remarkable stability. Sci. China Chem. 2020 , 63 , 904−910..

Tao, Y.; Yang, C.; Qin, J. Organic host materials for phosphorescent organic light-emitting diodes. Chem. Soc. Rev. 2011 , 40 , 2943−2970..

Yook, K. S.; Lee, J. Y. Small molecule host materials for solution processed phosphorescent organic light-emitting diodes. Adv. Mater. 2014 , 26 , 4218−4233..

Views

235

Downloads

CSCD

Alert me when the article has been cited

Submit

Tools

Publicity Resources

Experimental Investigation of Graphene and TiO2 Reinforced Poly(vinyl alcohol)-based Fiber Metal Laminates

Circularly Polarized Luminescence Based on Helical Polymers: Structure-Property Relationships and Regulation Mechanisms

Silk Sericin-inspired Poly-β-homoserine for Protein Protection

Tunable Circularly Polarized Luminescence of Helical Poly(phenylacetylene)s via Side-chain-to-Backbone Förster Resonance Energy Transfer

Highly Regio- and trans-Selective Ring-opening Metathesis Polymerization of Chiral Aza-norbornene with a Simple Phenylimido-Tungsten Catalyst

Related Author

No data

Related Institution

No data

⁰