Abstract

Solid-state, single-component green light-emitting electrochemical cells (LECs) based on a fluorene-benzothiadiazole copolymer has been successfully demonstrated. The solubilizing side groups are octyl and 2-(2-(2-methoxyethoxy)ethoxy)ethyl, with the latter introduced to promote ionic conductivity necessary for the operation of the LECs. The copolymer was synthesized by Suzuki coupling reactions with number-average molecular weight between 5,600 and 13,200 and polydispersity between 2.06 and 3.21. The LECs were fabricated by spin-coating the copolymer admixed with lithium trifluoromethanesulfonate onto indium-tin oxide (ITO) substrate coated with polyethylenedioxythiophene-polystyrene sulfonic acid (PEDOT:PSS). The opposite electrode was vapor evaporated aluminum. The LEC devices shows green electroluminescence with CIE coordinates of (0.37, 0.59). The devices exhibit comparable performance with corresponding light emitting diodes using evaporated barium as cathode. The copolymer with higher benzothiadiazole (BT) content shows relatively higher LEC device performance. Cyclic voltammetry and chemical doping measurements indicate that the polymer with higher BT content in the backbone can be more readily n-doped, which is consistent with the higher LEC performance.

© 2013 IEEE

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  2. Q. B. Pei, A. J. Heeger, "Operating mechanism of light-emitting electrochemical cells," Nat. Mater. 7, 167 (2008).
  3. Q. B. Pei, Y. Yang, G. Yu, C. Zhang, A. J. Heeger, "Polymer light-emitting electrochemical cells: In situ formation of a light-emitting p–n junction," J. Amer. Chem. Soc. 118, 3922-3929 (1996).
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  14. S. H. Oh, S. I. Na, Y. C. Nah, D. Vak, S. S. Kim, D. Y. Kim, "Novel cationic water-soluble polyfluorene derivatives with ion-transporting side groups for efficient electron injection in PLEDs," Organic Electron. 8, 773-783 (2007).
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  16. L. Edman, M. Pauchard, B. Liu, G. Bazan, D. Moses, A. J. Heeger, "Single-component light-emitting electrochemical cell with improved stability," Appl. Phys. Lett. 82, 3961 (2003).
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  18. F. Huang, L. Hou, H. Wu, X. Wang, H. Shen, W. Cao, W. Yang, Y. Cao, "High-efficiency, environment-friendly electroluminescent polymers with stable high work function metal as a cathode: Green- and yellow-emitting conjugated polyfluorene polyelectrolytes and their neutral precursors," J. Amer. Chem. Soc. 126, 9845-9853 (2004).
  19. J. Zaumseil, C. L. Donley, J.-S. Kim, R. H. Friend, H. Sirringhaus, "Efficient top-gate, ambipolar, light-emitting field-effect transistors based on a green-light-emitting polyfluorene," Adv. Mater. 18, 2708-2712 (2006).
  20. F. Wang, G. C. Bazan, "Aggregation-mediated optical properties of pH-responsive anionic conjugated polyelectrolytes," J. Amer. Chem. Soc,. 128, 15786-15792 (2006).
  21. E. M. D. Keegstra, J. W. Zwikker, M. R. Roest, L. W. Jenneskens, "A highly selective synthesis of monodisperse oligo(ethylene glycols)," J. Org. Chem. 57, 6678-6680 (1992).
  22. Y. Kim, S. Cook, S. A. Choulis, J. Nelson, J. R. Durrant, D. D. C. Bradley, "Organic photovoltaic devices based on blends of regioregular Poly(3-hexylthiophene) and Poly(9,9-dioctylfluorene-co-benzothiadiazole)," Chem. Mater. 16, 4812-4818 (2004).
  23. H. J. Snaith, R. H. Friend, "Morphological dependence of charge generation and transport in blended polyfluorene photovoltaic devices," Thin Solid Films 451–452, 567-571 (2004).
  24. R. Marcilla, D. Mecerreyes, G. Winroth, S. Brovelli, M. M. R. Yebra, F. Cacialli, "Light-emitting electrochemical cells using polymeric ionic liquid/polyfluorene blends as luminescent material," Appl. Phys. Lett,. 96, 043308 (2010).
  25. M. L. Sun, L. Wang, Y. Xia, B. Du, R. Liu, Y. Cao, "Fluorene-based copolymers for red light-emitting diodes and bulk heterojunction photovoltaic cell," Acta Polymerica Sinica. 10, 952-958 (2007).
  26. Y. F. Li, Y. Cao, J. Gao, D. L. Wang, G. Yu, A. J. Heeger, "Electrochemical properties of luminescent polymers and polymer light-emitting electrochemical cells," Synth. Met. 99, 243-248 (1999).
  27. L. S. Liao, M. K. Fung, C. S. Lee, S. T. Lee, M. Inbasekaran, E. P. Woo, W. W. Wu, "Electronic structure and energy band gap of poly (9,9-dioctylfluorene) investigated by photoelectron spectroscopy," Appl. Phys. Lett. 76, 3582-3584 (2000).
  28. S. Janietz, D. D. C. Bradley, M. Grell, C. Giebler, M. Inbasekaran, E. P. Woo, "Electrochemical determination of the ionization potential and electron affinity of poly(9,9-dioctylfluorene)," Appl. Phys. Lett.. 73, 2453-2455 (1998).
  29. J. H. Shin, N. D. Robinson, S. Xiao, L. Edman, "Polymer light-emitting electrochemical cells: Doping concentration, emission-zone position, and turn-on time," Adv. Funct. Mater. 17, 1807-1813 (2007).
  30. P. Pachler, F. P. Wenzl, U. Scherf, G. Leising, "The efficiency of light-emitting electrochemical cells," J. Phys. Chem. B 109, 6020-6024 (2005).
  31. D. H. Park, H. S. Kim, M. Y. Jeong, Y. B. Lee, H. J. Kim, D. C. Kim, J. Kim, J. Joo, "Significantly enhanced photoluminescence of doped polymer-metal hybrid nanotubes," Adv. Funct. Mater. 18, 2526-2534 (2008).

2012 (1)

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

2010 (2)

M. L. Sun, C. M. Zhong, F. Li, Y. Cao, Q. B. Pei, "A fluorene-oxadiazole copolymer for white light emitting electrochemical cells," Macromolecules 43, 1714-1718 (2010).

R. Marcilla, D. Mecerreyes, G. Winroth, S. Brovelli, M. M. R. Yebra, F. Cacialli, "Light-emitting electrochemical cells using polymeric ionic liquid/polyfluorene blends as luminescent material," Appl. Phys. Lett,. 96, 043308 (2010).

2009 (1)

D. Vak, S. H. Oh, D.-Y. Kim, "Efficient single-component light-emitting electrochemical cells with an ion-conducting water-soluble polyfluorene," Appl. Phys. Lett. 94, 243305 (2009).

2008 (3)

S. H. Oh, D. Vak, S. I. Na, T. W. Lee, D. Y. Kim, "Water-soluble polyfluorenes as an electron injecting layer in PLEDs for extremely high quantum efficiency," Adv. Mater. 20, 1624-1629 (2008).

Q. B. Pei, A. J. Heeger, "Operating mechanism of light-emitting electrochemical cells," Nat. Mater. 7, 167 (2008).

D. H. Park, H. S. Kim, M. Y. Jeong, Y. B. Lee, H. J. Kim, D. C. Kim, J. Kim, J. Joo, "Significantly enhanced photoluminescence of doped polymer-metal hybrid nanotubes," Adv. Funct. Mater. 18, 2526-2534 (2008).

2007 (4)

J. H. Shin, N. D. Robinson, S. Xiao, L. Edman, "Polymer light-emitting electrochemical cells: Doping concentration, emission-zone position, and turn-on time," Adv. Funct. Mater. 17, 1807-1813 (2007).

M. L. Sun, L. Wang, Y. Xia, B. Du, R. Liu, Y. Cao, "Fluorene-based copolymers for red light-emitting diodes and bulk heterojunction photovoltaic cell," Acta Polymerica Sinica. 10, 952-958 (2007).

Q. J. Sun, Y. L. Li, Q. B. Pei, "Polymer light-emitting electrochemical cells for high-efficiency, low-voltage electroluminescent devices," J. Display Technol. 3, 211-224 (2007).

S. H. Oh, S. I. Na, Y. C. Nah, D. Vak, S. S. Kim, D. Y. Kim, "Novel cationic water-soluble polyfluorene derivatives with ion-transporting side groups for efficient electron injection in PLEDs," Organic Electron. 8, 773-783 (2007).

2006 (2)

J. Zaumseil, C. L. Donley, J.-S. Kim, R. H. Friend, H. Sirringhaus, "Efficient top-gate, ambipolar, light-emitting field-effect transistors based on a green-light-emitting polyfluorene," Adv. Mater. 18, 2708-2712 (2006).

F. Wang, G. C. Bazan, "Aggregation-mediated optical properties of pH-responsive anionic conjugated polyelectrolytes," J. Amer. Chem. Soc,. 128, 15786-15792 (2006).

2005 (1)

P. Pachler, F. P. Wenzl, U. Scherf, G. Leising, "The efficiency of light-emitting electrochemical cells," J. Phys. Chem. B 109, 6020-6024 (2005).

2004 (3)

Y. Kim, S. Cook, S. A. Choulis, J. Nelson, J. R. Durrant, D. D. C. Bradley, "Organic photovoltaic devices based on blends of regioregular Poly(3-hexylthiophene) and Poly(9,9-dioctylfluorene-co-benzothiadiazole)," Chem. Mater. 16, 4812-4818 (2004).

H. J. Snaith, R. H. Friend, "Morphological dependence of charge generation and transport in blended polyfluorene photovoltaic devices," Thin Solid Films 451–452, 567-571 (2004).

F. Huang, L. Hou, H. Wu, X. Wang, H. Shen, W. Cao, W. Yang, Y. Cao, "High-efficiency, environment-friendly electroluminescent polymers with stable high work function metal as a cathode: Green- and yellow-emitting conjugated polyfluorene polyelectrolytes and their neutral precursors," J. Amer. Chem. Soc. 126, 9845-9853 (2004).

2003 (1)

L. Edman, M. Pauchard, B. Liu, G. Bazan, D. Moses, A. J. Heeger, "Single-component light-emitting electrochemical cell with improved stability," Appl. Phys. Lett. 82, 3961 (2003).

2002 (1)

P. Herguth, X. Jiang, M. S. Liu, A. K.-Y. Jen, "Highly efficient fluorene- and benzothiadiazole-based conjugated copolymers for polymer light-emitting diodes," Macromolecules 35, 6094-6100 (2002).

2001 (1)

J. Morgado, F. Cacialli, R. H. Friend, B. S. Chuah, H. Rost, A. B. Holmes, "Light-emitting devices based on a poly(p-phenylenevinylene) statistical copolymer with oligo(ethylene oxide) side groups," Macromolecules 34, 3094-3099 (2001).

2000 (2)

G. He, C. Yang, R. Wang, Y. Li, "Light-emitting electro-chemical cells based on poly-[2-methoxy-5-triethyxy-14-phenylene vinylene," Displays 21, 69-72 (2000).

L. S. Liao, M. K. Fung, C. S. Lee, S. T. Lee, M. Inbasekaran, E. P. Woo, W. W. Wu, "Electronic structure and energy band gap of poly (9,9-dioctylfluorene) investigated by photoelectron spectroscopy," Appl. Phys. Lett. 76, 3582-3584 (2000).

1999 (3)

Y. F. Li, Y. Cao, J. Gao, D. L. Wang, G. Yu, A. J. Heeger, "Electrochemical properties of luminescent polymers and polymer light-emitting electrochemical cells," Synth. Met. 99, 243-248 (1999).

L. Holzer, F. P. Wenzl, S. Tasch, G. Leising, B. Winkler, L. Dai, A. W. H. Mau, "Ionochromism in a light-emitting electrochemical cell with low response time based on an ionic conductive poly-phenylene vinylene," Appl. Phys. Lett. 75, 2014 (1999).

T. Johansson, W. Mammo, M. R. Andersson, O. Inganäs, "Light-emitting electrochemical cells from oligo(ethylene oxide)-substituted polythiophenes: Evidence for in situ doping," Chem. Mater. 11, 3133-3139 (1999).

1998 (1)

S. Janietz, D. D. C. Bradley, M. Grell, C. Giebler, M. Inbasekaran, E. P. Woo, "Electrochemical determination of the ionization potential and electron affinity of poly(9,9-dioctylfluorene)," Appl. Phys. Lett.. 73, 2453-2455 (1998).

1997 (1)

Y. Yang, Q. B. Pei, "Efficient blue-green and white light-emitting electrochemical cells based on poly[9,9-bis(3,6-dioxaheptyl)-fluorene-2,7-diyl]," J. Appl. Phys. 81, 3294 (1997).

1996 (2)

Q. B. Pei, Y. Yang, G. Yu, C. Zhang, A. J. Heeger, "Polymer light-emitting electrochemical cells: In situ formation of a light-emitting p–n junction," J. Amer. Chem. Soc. 118, 3922-3929 (1996).

Q. B. Pei, Y. Yang, "Efficient photoluminescence and electroluminescence from a soluble polyfluorene," J. Amer. Chem. Soc. 118, 7416-7417 (1996).

1995 (1)

Q. B. Pei, G. Yu, C. Zhang, Y. Yang, A. J. Heeger, "Polymer light-emitting electrochemical cells," Science 269, 1086-1088 (1995).

1992 (1)

E. M. D. Keegstra, J. W. Zwikker, M. R. Roest, L. W. Jenneskens, "A highly selective synthesis of monodisperse oligo(ethylene glycols)," J. Org. Chem. 57, 6678-6680 (1992).

Acta Polymerica Sinica. (1)

M. L. Sun, L. Wang, Y. Xia, B. Du, R. Liu, Y. Cao, "Fluorene-based copolymers for red light-emitting diodes and bulk heterojunction photovoltaic cell," Acta Polymerica Sinica. 10, 952-958 (2007).

Adv. Funct. Mater. (1)

J. H. Shin, N. D. Robinson, S. Xiao, L. Edman, "Polymer light-emitting electrochemical cells: Doping concentration, emission-zone position, and turn-on time," Adv. Funct. Mater. 17, 1807-1813 (2007).

Adv. Mater. (1)

S. H. Oh, D. Vak, S. I. Na, T. W. Lee, D. Y. Kim, "Water-soluble polyfluorenes as an electron injecting layer in PLEDs for extremely high quantum efficiency," Adv. Mater. 20, 1624-1629 (2008).

Adv. Funct. Mater. (1)

D. H. Park, H. S. Kim, M. Y. Jeong, Y. B. Lee, H. J. Kim, D. C. Kim, J. Kim, J. Joo, "Significantly enhanced photoluminescence of doped polymer-metal hybrid nanotubes," Adv. Funct. Mater. 18, 2526-2534 (2008).

Adv. Mater. (1)

J. Zaumseil, C. L. Donley, J.-S. Kim, R. H. Friend, H. Sirringhaus, "Efficient top-gate, ambipolar, light-emitting field-effect transistors based on a green-light-emitting polyfluorene," Adv. Mater. 18, 2708-2712 (2006).

Appl. Phys. Lett,. (1)

R. Marcilla, D. Mecerreyes, G. Winroth, S. Brovelli, M. M. R. Yebra, F. Cacialli, "Light-emitting electrochemical cells using polymeric ionic liquid/polyfluorene blends as luminescent material," Appl. Phys. Lett,. 96, 043308 (2010).

Appl. Phys. Lett. (4)

L. S. Liao, M. K. Fung, C. S. Lee, S. T. Lee, M. Inbasekaran, E. P. Woo, W. W. Wu, "Electronic structure and energy band gap of poly (9,9-dioctylfluorene) investigated by photoelectron spectroscopy," Appl. Phys. Lett. 76, 3582-3584 (2000).

D. Vak, S. H. Oh, D.-Y. Kim, "Efficient single-component light-emitting electrochemical cells with an ion-conducting water-soluble polyfluorene," Appl. Phys. Lett. 94, 243305 (2009).

L. Edman, M. Pauchard, B. Liu, G. Bazan, D. Moses, A. J. Heeger, "Single-component light-emitting electrochemical cell with improved stability," Appl. Phys. Lett. 82, 3961 (2003).

L. Holzer, F. P. Wenzl, S. Tasch, G. Leising, B. Winkler, L. Dai, A. W. H. Mau, "Ionochromism in a light-emitting electrochemical cell with low response time based on an ionic conductive poly-phenylene vinylene," Appl. Phys. Lett. 75, 2014 (1999).

Appl. Phys. Lett.. (1)

S. Janietz, D. D. C. Bradley, M. Grell, C. Giebler, M. Inbasekaran, E. P. Woo, "Electrochemical determination of the ionization potential and electron affinity of poly(9,9-dioctylfluorene)," Appl. Phys. Lett.. 73, 2453-2455 (1998).

Chem. Mater. (2)

Y. Kim, S. Cook, S. A. Choulis, J. Nelson, J. R. Durrant, D. D. C. Bradley, "Organic photovoltaic devices based on blends of regioregular Poly(3-hexylthiophene) and Poly(9,9-dioctylfluorene-co-benzothiadiazole)," Chem. Mater. 16, 4812-4818 (2004).

T. Johansson, W. Mammo, M. R. Andersson, O. Inganäs, "Light-emitting electrochemical cells from oligo(ethylene oxide)-substituted polythiophenes: Evidence for in situ doping," Chem. Mater. 11, 3133-3139 (1999).

Chinese J. Polymer Sci. (1)

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

Displays (1)

G. He, C. Yang, R. Wang, Y. Li, "Light-emitting electro-chemical cells based on poly-[2-methoxy-5-triethyxy-14-phenylene vinylene," Displays 21, 69-72 (2000).

J. Org. Chem. (1)

E. M. D. Keegstra, J. W. Zwikker, M. R. Roest, L. W. Jenneskens, "A highly selective synthesis of monodisperse oligo(ethylene glycols)," J. Org. Chem. 57, 6678-6680 (1992).

J. Amer. Chem. Soc. (1)

Q. B. Pei, Y. Yang, "Efficient photoluminescence and electroluminescence from a soluble polyfluorene," J. Amer. Chem. Soc. 118, 7416-7417 (1996).

J. Amer. Chem. Soc,. (1)

F. Wang, G. C. Bazan, "Aggregation-mediated optical properties of pH-responsive anionic conjugated polyelectrolytes," J. Amer. Chem. Soc,. 128, 15786-15792 (2006).

J. Amer. Chem. Soc. (2)

Q. B. Pei, Y. Yang, G. Yu, C. Zhang, A. J. Heeger, "Polymer light-emitting electrochemical cells: In situ formation of a light-emitting p–n junction," J. Amer. Chem. Soc. 118, 3922-3929 (1996).

F. Huang, L. Hou, H. Wu, X. Wang, H. Shen, W. Cao, W. Yang, Y. Cao, "High-efficiency, environment-friendly electroluminescent polymers with stable high work function metal as a cathode: Green- and yellow-emitting conjugated polyfluorene polyelectrolytes and their neutral precursors," J. Amer. Chem. Soc. 126, 9845-9853 (2004).

J. Appl. Phys. (1)

Y. Yang, Q. B. Pei, "Efficient blue-green and white light-emitting electrochemical cells based on poly[9,9-bis(3,6-dioxaheptyl)-fluorene-2,7-diyl]," J. Appl. Phys. 81, 3294 (1997).

J. Display Technol. (1)

J. Phys. Chem. B (1)

P. Pachler, F. P. Wenzl, U. Scherf, G. Leising, "The efficiency of light-emitting electrochemical cells," J. Phys. Chem. B 109, 6020-6024 (2005).

Macromolecules (3)

M. L. Sun, C. M. Zhong, F. Li, Y. Cao, Q. B. Pei, "A fluorene-oxadiazole copolymer for white light emitting electrochemical cells," Macromolecules 43, 1714-1718 (2010).

J. Morgado, F. Cacialli, R. H. Friend, B. S. Chuah, H. Rost, A. B. Holmes, "Light-emitting devices based on a poly(p-phenylenevinylene) statistical copolymer with oligo(ethylene oxide) side groups," Macromolecules 34, 3094-3099 (2001).

P. Herguth, X. Jiang, M. S. Liu, A. K.-Y. Jen, "Highly efficient fluorene- and benzothiadiazole-based conjugated copolymers for polymer light-emitting diodes," Macromolecules 35, 6094-6100 (2002).

Nat. Mater. (1)

Q. B. Pei, A. J. Heeger, "Operating mechanism of light-emitting electrochemical cells," Nat. Mater. 7, 167 (2008).

Organic Electron. (1)

S. H. Oh, S. I. Na, Y. C. Nah, D. Vak, S. S. Kim, D. Y. Kim, "Novel cationic water-soluble polyfluorene derivatives with ion-transporting side groups for efficient electron injection in PLEDs," Organic Electron. 8, 773-783 (2007).

Science (1)

Q. B. Pei, G. Yu, C. Zhang, Y. Yang, A. J. Heeger, "Polymer light-emitting electrochemical cells," Science 269, 1086-1088 (1995).

Synth. Met. (1)

Y. F. Li, Y. Cao, J. Gao, D. L. Wang, G. Yu, A. J. Heeger, "Electrochemical properties of luminescent polymers and polymer light-emitting electrochemical cells," Synth. Met. 99, 243-248 (1999).

Thin Solid Films (1)

H. J. Snaith, R. H. Friend, "Morphological dependence of charge generation and transport in blended polyfluorene photovoltaic devices," Thin Solid Films 451–452, 567-571 (2004).

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