Highly efficient organic solar cells with improved stability enabled by ternary copolymers with antioxidant side chains

Ao Song; Qiri Huang; Chunyang Zhang; Haoran Tang; Kai Zhang; Chunchen Liu; Fei Huang; Yong Cao

doi:10.1088/1674-4926/44/8/082202

J. Semicond. > 2023, Volume 44 > Issue 8 > 082202

ARTICLES

Highly efficient organic solar cells with improved stability enabled by ternary copolymers with antioxidant side chains

Ao Song^§, Qiri Huang^§, Chunyang Zhang, Haoran Tang, Kai Zhang, Chunchen Liu, Fei Huang and Yong Cao

+ Author Affiliations

Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology (SCUT), Guangzhou 510640, China
^§A. Song and Q. Huang contributed equally to this work and should be considered as co-first authors.

Author Bio:

Ao Song received her BS degree in engineering from Hunan Normal University in 2020. She is now a Master's student in the State Key Laboratory of Luminescent Materials and Devices in South China University of Technology. Her research focuses on the stability of high-performance organic solar cells.

Qiri Huang received his BS degree from Hefei University of Technology in 2020. He is now a Master's student in the State Key Laboratory of Luminescent Materials and Devices in South China University of Technology. His research focuses on developing high performance inverted organic solar cells.

Chunchen Liu is an associate research fellow in South China University of Technology. He received his BS degree in Polymer Materials and Engineering from South China University of Technology in 2010 and gained his PhD degree in Materials Science from the South China University of Technology in 2005 under the supervision of Prof. Yong Cao. After postdoctoral work at National University of Singapore with Prof. Jishan Wu, he began his academic carrier in 2019 as a research assistant professor of Southern University of Science and Technology and then moved to South China University of Technology in 2021. He mainly focuses on the design and synthesis of conjugated molecules, polymers, and polycyclic aromatic hydrocarbons with polyradicals for opto-electronics.

Fei Huang is a full professor at South China University of Technology. He received his BS degree in Chemistry from Peking University in 2000 and gained his PhD degree in Materials Science from the South China University of Technology in 2005 under the supervision of Prof. Yong Cao. After postdoctoral work at University of Washington with Prof. Alex K.-Y. Jen, he began his academic career in 2009 as a professor of South China University of Technology. His main interests are in organic functional materials and devices for opto-electronics.

Corresponding author: Chunchen Liu, mscliu@scut.edu.cn; Fei Huang, msfhuang@scut.edu.cn

DOI: 10.1088/1674-4926/44/8/082202

Abstract: The stability of organic solar cells (OSCs) remains a major concern for their ultimate industrialization due to the photo, oxygen, and water susceptibility of organic photoactive materials. Usually, antioxidant additives are blended as radical scavengers into the active layer. However, it will induce the intrinsic morphology instability and adversely affect the efficiency and long-term stability. Herein, the antioxidant dibutylhydroxytoluene (BHT) group has been covalently linked onto the side chain of benzothiadiazole (BT) unit, and a series of ternary copolymers D18-Cl-BTBHTx (x = 0, 0.05, 0.1, 0.2) with varied ratio of BHT-containing side chains have been synthesized. It was found that the introduction of BHT side chains would have a negligible effect on the photophysical properties and electronic levels, and the D18-Cl-BTBHT0.05: Y6-based OSC achieved the highest power conversion efficiency (PCE) of 17.6%, which is higher than those based active layer blended with BHT additives. More importantly, the unencapsulated device based on D18-Cl-BTBHTx (x = 0.05, 0.1, 0.2) retained approximately 50% of the initial PCE over 30 hours operation under ambient conditions, significantly outperforming the control device based on D18-Cl (90% degradation in PCE after 30 h). This work provides a new structural design strategy of copolymers for OSCs with simultaneously improved efficiency and stability.

Key words: organic solar cells, ternary copolymers, antioxidant side chain, photostability

References

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Fig. 1. (Color online) (a) Chemical structures of the copolymers D18-Cl-BTBHTx (x = 0, 0.05, 0.1, 0.2); (b) absorption spectra of D18-Cl, D18-Cl-BTBHT0.05, D18-Cl-BTBHT0.1, D18-Cl-BTBHT0.2 and Y6 in films; (c) schematic illustration of energy levels of D18-Cl, D18-Cl-BTBHT0.05, D18-Cl-BTBHT0.1, D18-Cl-BTBHT0.2 and Y6; (d) device architecture of OSCs employed in this study.

DownLoad: Full-Size Img PowerPoint

Fig. 2. (Color online) UV absorption spectra of D18-Cl-BTBHTx (x = 0, 0.05, 0.1, 0.2): Y6 blend films under continuous light irradiation at ambient condition, (a) D18-Cl: Y6, (b) D18-Cl-BTBHT0.05: Y6, (c) D18-Cl-BTBHT0.1: Y6, and (d) D18-Cl-BTBHT0.2: Y6 blend film, respectively.

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Fig. 3. (Color online) (a) J-V characteristics and (b) EQE spectra of the optimized OSCs measured under AM 1.5 G illumination (100 mW/cm²); PCEs evolution of D18-Cl-BTBHTx: Y6 cells aged at maximum power point (mpp) with continuous light illumination, encapsulated devices (c) in inert atmosphere and unencapsulated devices (d) at ambient conditions.

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Fig. 4. (Color online) EQEs evolution of D18-Cl-BTBHTx: Y6 cells aged at maximum power point (mpp) under continuous light illumination and ambient conditions; (a) D18-Cl, (b) D18-Cl-BTBHT0.05, (c) D18-Cl-BTBHT0.1 and (d) D18-Cl-BTBHT0.2-based device, respectively.

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Fig. 5. (Color online) Photocurrent density (J_ph) versus effective voltage (V_eff) curves of the (a) fresh and (b) aged 10 days D18-Cl-BTBHTx: Y6 cells; light intensity dependence of J_SC of the (c) fresh and (d) aged 20 hours D18-Cl-BTBHTx: Y6 cells; light intensity dependence of V_OC of the (e) fresh and (f) aged 20 hours D18-Cl-BTBHTx: Y6 cells.

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Fig. 6. (Color online) 2D-GIWAXS patterns of (a) as-prepared and (b) aged D18-Cl-BTBHTx: Y6 blend films, 1D line-cut profiles of (c) as-prepared and (d) aged D18-Cl-BTBHTx: Y6 blend films.

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Table 1. Molecular weights, optical properties, and electronic energy levels of copolymers D18-Cl-BTBHTx (x = 0, 0.05, 0.1, 0.2).

Polymer	Mn (kDa)	PDI	λ_max^a (nm)	λ_onset^a (nm)	E_g^{opt b} (eV)	E_ox (V)	E_HOMO^c (eV)	E_LUMO^d (eV)
D18-Cl	58.0	2.3	545, 580	636	1.95	1.16	−5.57	−3.62
D18-Cl-BTBHT0.05	58.2	1.9	540, 574	626	1.98	1.19	−5.60	−3.62
D18-Cl-BTBHT0.1	49.8	1.6	541, 576	642	1.93	1.20	−5.61	−3.68
D18-Cl-BTBHT0.2	49.9	1.9	540, 576	646	1.92	1.16	−5.57	−3.65
^a In films. ^b E_g^opt = 1240/λ_onset. ^cE_HOMO = -(E_ox - E_{(Fc/ Fc}⁺₎+ 4.8) eV, ^dE_LUMO = E_HOMO+ E_g^opt.

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Table 2. Photovoltaic parameters of D18-Cl-BTBHTx: Y6-based OSCs. ^a

Active layer	V_OC (V)	J_SC (mA/cm²)	FF (%)	PCE_MAX (%)
D18-Cl: Y6	0.89 (0.88±0.00)	26.92 (26.71±0.18)	72.15 (71.57±0.73)	17.13 (16.91±0.22)
D18-Cl-BTBHT0.05: Y6	0.88 (0.87±0.00)	27.43 (26.98±0.45)	73.25 (72.88±0.33)	17.6 (17.17±0.41)
D18-Cl-BTBHT0.1: Y6	0.88 (0.88±0.00)	27.16 (26.82±0.28)	73.35 (72.66±0.58)	17.41 (17.06±0.25)
D18-Cl-BTBHT0.2: Y6	0.87 (0.87±0.00)	26.95 (26.43±0.42)	70.49 (69.66±0.60)	16.61 (16.07±0.40)
^a The average data and the corresponding standard deviation were calculated over 12 individual devices.

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Table 3. The carrier mobilities of blended active-layer films. ^a

	μ_h (10⁻⁴ cm²/(V·s))	μ_e (10⁻⁴cm²/(V·s))	μ_h/μ_e
D18-Cl: Y6	6.46	3.50	1.84
D18-Cl-BTBHT0.05: Y6	7.94	4.73	1.68
D18-Cl-BTBHT0.1: Y6	8.27	4.59	1.80
D18-Cl-BTBHT0.2: Y6	6.10	3.30	1.85
^a Mobility data were measured by the SCLC method.

DownLoad: CSV

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[33]	Rivaton A, Tournebize A, Gaume J, et al. Photostability of organic materials used in polymer solar cells. Polym Int, 2014, 63(8), 1335 doi: 10.1002/pi.4656
[34]	Jørgensen M, Norrman K, Gevorgyan S A, et al. Stability of polymer solar cells. Adv Mater, 2012, 24(5), 580 doi: 10.1002/adma.201104187
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[43]	Qin J, Zhang L, Zuo C, et al. A chlorinated copolymer donor demonstrates a 18.13% power conversion efficiency. J Semicond, 2021, 42(1), 010501 doi: 10.1088/1674-4926/42/1/010501
[44]	Gong X, Li G W, Wu Y, et al. Enhancing the performance of polymer solar cells by using donor polymers carrying discretely distributed side chains. ACS Appl Mater Interfaces, 2017, 9(28), 24020 doi: 10.1021/acsami.7b04369
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[50]	Koster L J A, Mihailetchi V D, Ramaker R, et al. Light intensity dependence of open-circuit voltage of polymer: Fullerene solar cells. Appl Phys Lett, 2005, 86(12), 123509 doi: 10.1063/1.1889240
[51]	Mihailetchi V D, Wildeman J, Blom P W M. Space-charge limited photocurrent. Phys Rev Lett, 2005, 94(12), 126602 doi: 10.1103/PhysRevLett.94.126602

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Received: 15 February 2023 Revised: 15 March 2023 Online: Accepted Manuscript: 24 May 2023Corrected proof: 27 June 2023Uncorrected proof: 28 June 2023Published: 10 August 2023

Article Navigation > Journal of Semiconductors > 2023 > 44(8): 082202

Ao Song, Qiri Huang, Chunyang Zhang, Haoran Tang, Kai Zhang, Chunchen Liu, Fei Huang, Yong Cao. Highly efficient organic solar cells with improved stability enabled by ternary copolymers with antioxidant side chains[J]. Journal of Semiconductors, 2023, 44(8): 082202. doi: 10.1088/1674-4926/44/8/082202 ****A Song, Q R Huang, C Y Zhang, H R Tang, K Zhang, C C Liu, F Huang, Y Cao. Highly efficient organic solar cells with improved stability enabled by ternary copolymers with antioxidant side chains[J]. J. Semicond, 2023, 44(8): 082202. doi: 10.1088/1674-4926/44/8/082202

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A Song, Q R Huang, C Y Zhang, H R Tang, K Zhang, C C Liu, F Huang, Y Cao. Highly efficient organic solar cells with improved stability enabled by ternary copolymers with antioxidant side chains[J]. J. Semicond, 2023, 44(8): 082202. doi: 10.1088/1674-4926/44/8/082202

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Highly efficient organic solar cells with improved stability enabled by ternary copolymers with antioxidant side chains

DOI: 10.1088/1674-4926/44/8/082202

Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology (SCUT), Guangzhou 510640, China

More Information

Ao Song：received her BS degree in engineering from Hunan Normal University in 2020. She is now a Master's student in the State Key Laboratory of Luminescent Materials and Devices in South China University of Technology. Her research focuses on the stability of high-performance organic solar cells
Qiri Huang：received his BS degree from Hefei University of Technology in 2020. He is now a Master's student in the State Key Laboratory of Luminescent Materials and Devices in South China University of Technology. His research focuses on developing high performance inverted organic solar cells
Chunchen Liu：is an associate research fellow in South China University of Technology. He received his BS degree in Polymer Materials and Engineering from South China University of Technology in 2010 and gained his PhD degree in Materials Science from the South China University of Technology in 2005 under the supervision of Prof. Yong Cao. After postdoctoral work at National University of Singapore with Prof. Jishan Wu, he began his academic carrier in 2019 as a research assistant professor of Southern University of Science and Technology and then moved to South China University of Technology in 2021. He mainly focuses on the design and synthesis of conjugated molecules, polymers, and polycyclic aromatic hydrocarbons with polyradicals for opto-electronics
Fei Huang：is a full professor at South China University of Technology. He received his BS degree in Chemistry from Peking University in 2000 and gained his PhD degree in Materials Science from the South China University of Technology in 2005 under the supervision of Prof. Yong Cao. After postdoctoral work at University of Washington with Prof. Alex K.-Y. Jen, he began his academic career in 2009 as a professor of South China University of Technology. His main interests are in organic functional materials and devices for opto-electronics
Corresponding author: mscliu@scut.edu.cn; msfhuang@scut.edu.cn
Received Date: 2023-02-15
Revised Date: 2023-03-15

Available Online: 2023-05-24

Abstract

Abstract

The stability of organic solar cells (OSCs) remains a major concern for their ultimate industrialization due to the photo, oxygen, and water susceptibility of organic photoactive materials. Usually, antioxidant additives are blended as radical scavengers into the active layer. However, it will induce the intrinsic morphology instability and adversely affect the efficiency and long-term stability. Herein, the antioxidant dibutylhydroxytoluene (BHT) group has been covalently linked onto the side chain of benzothiadiazole (BT) unit, and a series of ternary copolymers D18-Cl-BTBHTx (x = 0, 0.05, 0.1, 0.2) with varied ratio of BHT-containing side chains have been synthesized. It was found that the introduction of BHT side chains would have a negligible effect on the photophysical properties and electronic levels, and the D18-Cl-BTBHT0.05: Y6-based OSC achieved the highest power conversion efficiency (PCE) of 17.6%, which is higher than those based active layer blended with BHT additives. More importantly, the unencapsulated device based on D18-Cl-BTBHTx (x = 0.05, 0.1, 0.2) retained approximately 50% of the initial PCE over 30 hours operation under ambient conditions, significantly outperforming the control device based on D18-Cl (90% degradation in PCE after 30 h). This work provides a new structural design strategy of copolymers for OSCs with simultaneously improved efficiency and stability.
- organic solar cells,
- ternary copolymers,
- antioxidant side chain,
- photostability

Supplementary materials to this article can be found on-line at https://doi.org/1674-4926/44/8/082202.
^§A. Song and Q. Huang contributed equally to this work and should be considered as co-first authors.

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References

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Highly efficient organic solar cells with improved stability enabled by ternary copolymers with antioxidant side chains

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