Photocurrent in the Polyfluorene Copolymer/PTCDI Heterojunction Enhanced by Reabsorption of Fluorescence Emission

Dmitriy A. Lypenko; Alexey E. Aleksandrov; Artem V. Dmitriev; Anton A. Yakimanskiy; Ilya E. Kolesnikov; Tatiana G. Chulkova; Alexander V. Yakimansky; Alexey R. Tameev

doi:10.1007/s10118-024-3231-4

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Photocurrent in the Polyfluorene Copolymer/PTCDI Heterojunction Enhanced by Reabsorption of Fluorescence Emission

RESEARCH ARTICLE | Updated：2024-12-03

- Photocurrent in the Polyfluorene Copolymer/PTCDI Heterojunction Enhanced by Reabsorption of Fluorescence Emission
- Chinese Journal of Polymer Science Vol. 42, Issue 12, Pages: 1941-1947(2024)
- Affiliations：
  
  a.Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences, 31/bld.4 Leninskiy Prospect, Moscow 119071, Russia
  b.Institute of Macromolecular Compounds of the Russian Academy of Sciences, 31 Bolshoi pr. VO, Saint Petersburg 199004, Russia
  c.Saint Petersburg State University, 7/9 Universitetskaya nab., Saint Petersburg 199034, Russia
- Author bio：
  
  tameev@elchem.ac.ru
- Funds：
- DOI：10.1007/s10118-024-3231-4
  CLC：
- Published：01 December 2024，
  
  Published Online：29 October 2024，
  
  Received：08 June 2024，
  
  Revised：28 August 2024，
  
  Accepted：05 September 2024
- Accepted：
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Lypenko, D. A.; Aleksandrov, A. E.; Dmitriev, A. V.; Yakimanskiy, A. A.; Kolesnikov, I. E.; Chulkova, T. G.; Yakimansky, A. V.; Tameev, A. R. Photocurrent in the polyfluorene copolymer/PTCDI heterojunction enhanced by reabsorption of fluorescence emission. Chinese J. Polym. Sci. 2024, 42, 1941–1947

DMITRIY A. LYPENKO, ALEXEY E. ALEKSANDROV, ARTEM V. DMITRIEV, et al. Photocurrent in the Polyfluorene Copolymer/PTCDI Heterojunction Enhanced by Reabsorption of Fluorescence Emission. [J]. Chinese journal of polymer science, 2024, 42(12): 1941-1947.
Lypenko, D. A.; Aleksandrov, A. E.; Dmitriev, A. V.; Yakimanskiy, A. A.; Kolesnikov, I. E.; Chulkova, T. G.; Yakimansky, A. V.; Tameev, A. R. Photocurrent in the polyfluorene copolymer/PTCDI heterojunction enhanced by reabsorption of fluorescence emission. Chinese J. Polym. Sci. 2024, 42, 1941–1947 DOI： 10.1007/s10118-024-3231-4.

DMITRIY A. LYPENKO, ALEXEY E. ALEKSANDROV, ARTEM V. DMITRIEV, et al. Photocurrent in the Polyfluorene Copolymer/PTCDI Heterojunction Enhanced by Reabsorption of Fluorescence Emission. [J]. Chinese journal of polymer science, 2024, 42(12): 1941-1947. DOI： 10.1007/s10118-024-3231-4.

摘要

Energy diagram of the studied devices and transport of photogenerated charge carriers. HTL and ETL are hole and electron transport layers

respectively; PL is photoluminescence; CPF is copolyfluorene with dicyanostilbene (FFCN) or dicyanophenatrene (PFCN). CPF and PTCDI were used as photoactive materials. The structure of the PFCN copolymer (top).

Abstract

Copolyfluorenes are of great interest due to their ability to form thin films with tunable optical and electrical properties. In this paper

copolymers of polyfluorene with electron withdrawing dicyanostilbene and dicyanophenanthrene moieties were synthesized; their thin films were characterized by electron spectroscopy

cyclic voltammetry

electrical

and photoelectrical measurements. The mobility of charge carriers in the copolymers was measured for the first time

with the acceptor components providing balanced electron and hole mobilities of the order of 10

−6

·V

−1

·s

−1

. Photodetectors based on the copolymer/PTCDI heterojunction exhibited the photoresponse band extended into the green region due to the absorption of PTCDI and an increased photocurrent in the UV-blue absorption band of the copolymer

which is related to the absorption of photoluminescent emission of the copolymers in PTCDI. The presented approach to improving the performance of a polymer-based photodetector is promising in organic optoelectronics.

关键词

Keywords

Polyfluorene copolymerPerylenedicarboximide derivativeCharge carrier mobilityFluorescencePhotoconductivity

references

Grimsdale, A. C.; Chan, K. L.; Martin, R. E.; Jokisz, P. G.; Holmes, A. B. Synthesis of light-emitting conjugated polymers for applications in electroluminescent devices.Chem. Rev.2009,109, 897−1091..

Nosova, G.I.; Lypenko, D.A.; Smyslov, R.Y.; Zhukova, E. V.; Berezin, I. A.; Litvinova, L. S.; Maltsev, E. I.; Yakimansky, A. V. Copolyfluorenes containing carbazole or triphenylamine and diethoxylphosphoryl groups in the side chains as white-light-emitting polymers.Polymer2020,210, 122978..

Ostroverkhova, O. Organic optoelectronic materials: mechanisms and applications.Chem. Rev.2016,116, 22, 13279−13412..

Khasbaatar, A.; Xu, Z.; Lee, J. H.; Campillo-Alvarado, G.; Hwang, C.; Onusaitis, B.N.; Diao, Y. From solution to thin film: molecular assembly ofπ-conjugated systems and impact on (opto)electronic properties.Chem. Rev.2023,123, 8395−8487..

Dou, L.; Liu, Y.; Hong, Z.; Li, G.; Yang, Y. Low-bandgap near-IR conjugated polymers/molecules for organic electronics.Chem. Rev.2015,115, 23, 12633−12665..

Yang, Y.; Turnbull, G. A.; and Samuel, I. D. W. Sensitive explosive vapor detection with polyfluorene lasers.Adv. Funct. Mater.2010,20, 13, 2093−2097..

Yang, Y.; Turnbull, G. A.; Samuel, I. D. W. Hybrid optoelectronics: a polymer laser pumped by a nitride light-emitting diode.Appl. Phys. Lett.2008,92, 16, 163306..

Bai, Z.; Liu, Y.; Li, T.; Li, X.; Liu, B.; Liu, B.; Lu, D. Quantitative study onβ-phase heredity based on poly(9,9-dioctylfluorene) from solutions to films and the effect on hole mobility.J. Phys. Chem. C2016,120, 27820−27828..

Redecker, M.; Bradley, D. D. C.; Inbasekaran, M.; Woo, E. P. Nondispersive hole transport in an electroluminescent polyfluorene.Appl. Phys. Lett.1998,73, 1565−1567..

Lu, H. H.; Liu, C. Y.; Chang, C. H.; Chen, S. A. Self-dopant formation in poly(9,9-di-n-octylfluorene)viaa dipping method for efficient and stable pure-blue electroluminescence.Adv. Mater.2007,19, 2574−2579..

Liu, B.; Bai, Z.; Li, T.; Liu, Y.; Li, X.; Zhang, H.; Lu, D. Discovery and structure characteristics of the intermediate-state conformation of poly(9,9-dioctylfluorene) (PFO) in the dynamic process of conformation transformation and its effects on carrier mobility.RSC Adv. 2020,10, 1, 492−500..

Prins, P.; Grozema, F. C.; Nehls, B. S.; Farrell, T.; Scherf, U.; Siebbeles, L. D. A. Enhanced charge-carrier mobility inβ-phase polyfluorene.Phys. Rev. B2006,74, 113203..

Chua, L.L.; Zaumseil, J.; Chang, J.F.; Ou, E. C. W.; Ho, P. K. H.; Sirringhaus. H.; Friend, R. H. General observation of n-type field-effect behaviour in organic semiconductors.Nature2005,434, 194−199..

Al-Azzawi, A. G. S.; Aziz, S. B.; Dannoun, E. M. A.; Iraqi, A.; Nofal, M. M.; Murad, A. R.; M. Hussein, A. A mini review on the development of conjugated polymers: steps towards the commercialization of organic solar cells.Polymers2023,15, 164..

Azadinia, M.; Boroumand, F. A.; Fathollahi, M. R.; Mohajerani, E. Polyfluorene copolymer /Al Schottky junction for UV-A photodetector with relatively high stability and photocurrent density.Optics Commun.2020,458, 124809..

Yakimanskiy, A.A.; Kaskevich, K.I.; Chulkova, T.G.; Krasnopeeva, E.L.; Savilov, S.V.; Voinova, V.V.; Neumolotov, N.K.; Zhdanov, A.P.; Rogova, A.V.; Tomilin, F.N. Effect of complexation with closo-decaborate anion on photophysical properties of copolyfluorenes containing dicyanophenanthrene units in the main chain.Micro2023,3, 930−940..

Jeong, H. G.; Khim, D.; Jung, E.; Yun, J. M.; Kim, J.; Ku, J.; Jang, Y. H.; Kim, D. Y. Synthesis and characterization of a novel ambipolar polymer semiconductor based on a fumaronitrile core as an electron-withdrawing group.J. Polym. Sci., Part A: Polym. Chem.2013,51, 1029−1039..

Yakimanskiy, A. A.; Kaskevich, K. I.; Zhukova, E. V.; Berezin, I. A.; Litvinova, L. S.; Chulkova, T. G.; Lypenko, D. A.; Dmitriev, A. V.; Pozin, S. I.; Nekrasova, N. V. Synthesis, photo- and electroluminescence of new polyfluorene copolymers containing dicyanostilbene and 9,10-dicyanophenanthrene in the main chain.Materials2023,16, 5592..

Levell, J.; Giardini, M.; Samuel, I. A hybrid organic semiconductor/silicon photodiode for efficient ultraviolet photodetection.Opt. Express2010,18, 3219−3225..

Jansen-van Vuuren, R. D.; Armin, A.; Pandey, A. K.; Burn, P. L.; Meredith, P. Organic photodiodes: the future of full color detection and image sensing.Adv. Mater.2016,28, 4766−4802..

Gunduz, B. Sensing properties of theN,N′-dipentyl-3,4,9,10-perylenedicarboximide small molecule for different concentrations and solvents for sensor applications.Sensor Letters2015,13, 52−63..

Hiroshiba, N.; Hayakawa, R.; Chikyow, T.; Matsuishi, K.; Wakayama, Y. Ambipolar carrier transport in hetero-layered organic transistors consisting of quaterrylene andN,N′-dioctyl-3,4,9,10-perylenedicarboximide.Org. Electron.2011,12, 1336−1340..

Würthner, F.; Stepanenko, V.; Chen, Z.; Saha-Möller, C.R.; Kocher, N.; Stalke, D. Preparation and characterization of regioisomerically pure 1,7-disubstituted perylene bisimide dyes.J. Org. Chem.2004,69, 7933−7939..

Donati, F.; Pucci, A.; Cappelli, C.; Mennucci, B.; Ruggeri, G. Modulation of the optical response of polyethylene films containing luminescent perylene chromophores.J. Phys. Chem. B2008,112, 3668−3679..

Demina, N. S.; Rasputin, N. A.; Irgashev, R. A.; Tameev, A. R.; Nekrasova, N. V.; Rusinov, G. L.; Nunzi, J. M.; Charushin, V. N. Benzo[b]selenophene/thieno[3,2-b]indole-based N,S,Se-heteroacenes for hole-transporting layers.ACS Omega2020,5, 9377−9383..

Namazian, M.; Lin, C. Y.; Coote, M. L. Benchmark calculations of absolute reduction potential of ferricinium/ferrocene couple in nonaqueous solutions.J. Chem. Theory Comput.2010,6, 2721−2725..

Malov, V. V.; Tanwistha, G.; Nair, V. C.; Maslov, M. M.; Katin, K. P.; Unni, K. N. N.; Tameev, A. R. Hole mobility in thieno [3,2-bthiophene oligomers].Mendeleev Commun.2019,29, 218−219..

Simonova, M.; Filippov, A.; Nosova, G.; Zhukova, E.; Litvinova, L.; Berezin, I.; Yakimansky, A. Carbazole-functionalized polyfluorenes: synthesis and conformational properties in chloroform solution andβ-phase formation in copolyfluorene films.Mater. Today Chem.2021,22, 100553..

Klärner, G.; Lee, J. I.; Davey, M. H.; Miller, R. D. Exciton migration and trapping in copolymers based on dialkylfluorenes.Adv. Mater.1999,11, 115−119..

Chew, K. W.; Abdul Rahim, N. A.; Teh, P. L.; Abdul Hisam, N. S.; Alias, S. S. Thermal degradation of photoluminescence poly(9,9-dioctylfluorene) solvent-tuned aggregate films.Polymers2022,14, 1615..

Perevedentsev, A.; Chander, N.; Kim, J. S.; Bradley, D. D. C. Spectroscopic properties of poly(9,9-dioctylfluorene) thin films possessing varied fractions ofβ-phase chain segments: enhanced photoluminescence efficiency via conformation structuring.J. Polym. Sci., Part B: Polym. Phys.2016,54, 1995−2006..

Zhao, S.; Liang, J.; Guo, T.; Wang, Y.; Chen, X.; Fu, D.; Xiong, J.; Ying, L.; Yang, W.; Peng, J. Formation of poly(9,9-dioctylfluorene)β-phase by incorporating aromatic moiety in side chain.Org. Electron.2016,38, 130−138..

Zhang, Q.; Chi, L.; Hai, G.; Fang, Y.; Li, X.; Xia, R.; Huang, W.; Gu, E. An easy approach to controlβ-phase formation in PFO films for optimized emission properties.Molecules2017,22, 1−8..

Kim, J. Y.; Chung, I. J.; Kim, Y. C.; Yu, J. W. Mobility of electrons and holes in a liquid crystalline perylene diimide thin film with time of flight technique.Chem. Phys. Lett.2004,398, 367−371..

Cheng, J.; Kanehashi, S.; Ogino, K. Synthesis and electron transporting properties of triblock copolymers consisting of polyfluorene and polystyrene.Jpn. J. Appl. Phys.2022,61, SE1008..

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