Chlorinated Effects of Double-Cable Conjugated Polymers on the Photovoltaic Performance in Single-Component Organic Solar Cells

Han-Yi Bao; Zhao-Fan Yang; Yan-Jiao Zhao; Xiang Gao; Xin-Zhu Tong; Yi-Nuo Wang; Feng-Bo Sun; Jian-Hong Gao; Wei-Wei Li; Zhi-Tian Liu

doi:10.1007/s10118-022-2841-y

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Chlorinated Effects of Double-Cable Conjugated Polymers on the Photovoltaic Performance in Single-Component Organic Solar Cells

RESEARCH ARTICLE | Updated：2023-01-06

- Chlorinated Effects of Double-Cable Conjugated Polymers on the Photovoltaic Performance in Single-Component Organic Solar Cells
- role： First author , 第一作者 ,
  
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  Hubei Engineering Technology Research Center of Optoelectronic and New Energy Materials, Hubei Key Laboratory of Plasma Chemistry and Advanced Materials, School of Materials Science and Engineering, Wuhan Institute of Technology, Wuhan 430205, China
  
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  Bao Han-Yi
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  Beijing Advanced Innovation Center for Soft Matter Science and Engineering & State Key Laboratory of Organic-Inorganic Composite, Beijing University of Chemical Technology, Beijing 100029, China
  
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  Yang Zhao-Fan
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  Hubei Engineering Technology Research Center of Optoelectronic and New Energy Materials, Hubei Key Laboratory of Plasma Chemistry and Advanced Materials, School of Materials Science and Engineering, Wuhan Institute of Technology, Wuhan 430205, China
  
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  Zhao Yan-Jiao
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  role： Corresponding author , 通讯作者 ,
  
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  Hubei Engineering Technology Research Center of Optoelectronic and New Energy Materials, Hubei Key Laboratory of Plasma Chemistry and Advanced Materials, School of Materials Science and Engineering, Wuhan Institute of Technology, Wuhan 430205, China
  
  Email： xgao@wit.edu.cn
  
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  Gao Xiang
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  Hubei Engineering Technology Research Center of Optoelectronic and New Energy Materials, Hubei Key Laboratory of Plasma Chemistry and Advanced Materials, School of Materials Science and Engineering, Wuhan Institute of Technology, Wuhan 430205, China
  
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  Tong Xin-Zhu
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  Hubei Engineering Technology Research Center of Optoelectronic and New Energy Materials, Hubei Key Laboratory of Plasma Chemistry and Advanced Materials, School of Materials Science and Engineering, Wuhan Institute of Technology, Wuhan 430205, China
  
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  Wang Yi-Nuo
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  Hubei Engineering Technology Research Center of Optoelectronic and New Energy Materials, Hubei Key Laboratory of Plasma Chemistry and Advanced Materials, School of Materials Science and Engineering, Wuhan Institute of Technology, Wuhan 430205, China
  
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  Sun Feng-Bo
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  Hubei Engineering Technology Research Center of Optoelectronic and New Energy Materials, Hubei Key Laboratory of Plasma Chemistry and Advanced Materials, School of Materials Science and Engineering, Wuhan Institute of Technology, Wuhan 430205, China
  
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  Gao Jian-Hong
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  Beijing Advanced Innovation Center for Soft Matter Science and Engineering & State Key Laboratory of Organic-Inorganic Composite, Beijing University of Chemical Technology, Beijing 100029, China
  
  Email： liweiwei@iccas.ac.cn
  
  Introduction： liweiwei@iccas.ac.cn (W.W.L.)
  
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  Li Wei-Wei
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  Hubei Engineering Technology Research Center of Optoelectronic and New Energy Materials, Hubei Key Laboratory of Plasma Chemistry and Advanced Materials, School of Materials Science and Engineering, Wuhan Institute of Technology, Wuhan 430205, China
  
  Email： able.ztliu@wit.edu.cn
  
  Introduction： able.ztliu@wit.edu.cn (Z.T.L.)
  
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  Liu Zhi-Tian
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- Chinese Journal of Polymer Science Vol. 41, Issue 2, Pages: 187-193(2023)
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  a.Hubei Engineering Technology Research Center of Optoelectronic and New Energy Materials, Hubei Key Laboratory of Plasma Chemistry and Advanced Materials, School of Materials Science and Engineering, Wuhan Institute of Technology, Wuhan 430205, China
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  liweiwei@iccas.ac.cn (W.W.L.)
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- DOI：10.1007/s10118-022-2841-y
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Han-Yi Bao, Zhao-Fan Yang, Yan-Jiao Zhao, et al. Chlorinated Effects of Double-Cable Conjugated Polymers on the Photovoltaic Performance in Single-Component Organic Solar Cells. [J]. Chinese Journal of Polymer Science 41(2):187-193(2023)
DOI：

Han-Yi Bao, Zhao-Fan Yang, Yan-Jiao Zhao, et al. Chlorinated Effects of Double-Cable Conjugated Polymers on the Photovoltaic Performance in Single-Component Organic Solar Cells. [J]. Chinese Journal of Polymer Science 41(2):187-193(2023) DOI： 10.1007/s10118-022-2841-y.

Chlorinated Effects of Double-Cable Conjugated Polymers on the Photovoltaic Performance in Single-Component Organic Solar Cells

Bao Han-Yi ; Yang Zhao-Fan ; Zhao Yan-Jiao ; Gao Xiang ; Tong Xin-Zhu ; Wang Yi-Nuo ; Sun Feng-Bo ; Gao Jian-Hong ; Li Wei-Wei ; Liu Zhi-Tian ;

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Abstract

The recently emerged double-cable conjugated polymers have come into focus due to their significantly improved power conversion efficiencies (PCEs) in single-component organic solar cells (SCOSCs). In this work, the effect of chlorination in double-cable conjugated polymers with linear benzodithiophene backbone and pendant perylene bisimide on the photovoltaic performance in SCOSCs has been studied. After introducing chlorine atoms into conjugated side chains, the highest occupied molecular orbital level of the conjugated polymers is down-shifted, thus resulting in a higher open-circuit voltage. As a result, the chlorinated double-cable conjugated polymer exhibits improved photovoltaic performance from 3.46% to 3.57%.

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Keywords

Double-cable conjugated polymer; Chlorination; Single-component organic solar cells

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INTRODUCTION

Organic solar cells (OSCs) have drawn great attention because of the potential in portal electronics, internet of things, etc.^[

1−4] Among different device configurations, the bulk heterojunction (BHJ) OSCs which use a blend film of donor and acceptor materials as the active layer have been widely investigated. The power conversion efficiency (PCE) of single junction BHJ OSCs has exceeded 19%.^{[Reference 5

5]} However, the vital nano-size phase separation in the BHJ OSCs would become unstable during long time application or under high temperature.^{[Reference 6−14

6−14]} On the contrary, single-component OSCs (SCOSCs) exhibited significantly enhanced phase and thermal stability,^{[Reference 12

12,Reference 15−17

15−17]} suggesting a promising potential of SCOSCs for large-area rugged devices.

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Double-cable polymer is a type of materials that can be applied in SCOSCs.^[

18−28] These materials typically comprise conjugated donor backbones and pendant acceptors. In the early reports, double-cable conjugated polymers were mostly constructed via polythiophene-based backbones and fullerene side units, which severely limited the development of SCOSCs.^{[Reference 23−26

23−26,Reference 29

29]} In recent years, we have designed a series of new double-cable conjugated polymers by using rylene dimides as the pendant acceptors.^{[Reference 8

8,Reference 10

10,Reference 18−20

18−20,Reference 30−32

30−32]} Compared with fullerene, these rylene dimides, including naphthalene diimides (NDIs) and perylene bisimides (PBIs) which have been widely used to construct nonfullerene acceptors,^{[Reference 11

11,Reference 33−38

33−38]} exhibit strong absorption in the visible region. The properties of the double-cable polymers can be modified when changing the position of PBI units to the conjugated backbone.^{[Reference 8

8,Reference 21

21]} It should also be noted that the NDI unit has the great potential to provide a remarkable performance in SCOSCs,^{[Reference 9

9]} Besides changing the pendant acceptors, conjugated backbone engineering is another important way to improve the photovoltaic performance of SCOSCs. We usually use the “functionalization-polymerization” method to synthesize these double-cable conjugated polymers.^{[Reference 39

39]} There are numerous electron-rich and electron-deficient groups that could be introduced into the conjugated polymers by using these methods.^{[Reference 15

15]} Hence, the absorption spectrum, energy levels, and the crystallinity of the donor backbone could be easily tuned by changing the monomer structures.^{[Reference 9

9,Reference 19

19,Reference 21

21,Reference 31

31,Reference 40

40]} Thirdly, the linkers between the conjugated backbone and side acceptors also play an important role in determining the crystallinity, thus improving the nano-phase separation and photovoltaic performance.^{[Reference 41−43

41−43]} Recently, several rigid phenyl linkers have been introduced into double-cable conjugated polymers, suggesting that the D/A distance could also affect the open-circuit voltage (V_oc) and hence the performance of the SCOSCs.^{[Reference 42

42]}

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Halogenation has been widely used to modify the organic photovoltaic materials.^[

44−46] Compared to fluorinated photovoltaic materials, chlorinated ones are more attractive because they could be easily synthesized using low-cost reagents with higher yields.^{[Reference 47−49

47−49]} In addition, the chlorinated p-type polymers possess lower frontier energy levels than the fluorinated ones,^{[Reference 48

48,Reference 50−55

50−55]} benefiting for higher V_oc.^{[Reference 56−58

56−58]} Moreover, chlorination could improve the polymers’ crystallinity, charge mobility, the miscibility with acceptor molecules, and the morphology.^{[Reference 44

44,Reference 48

48,Reference 59−61

59−61]}

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In this work, we studied the effects of chlorination on the physical and photovoltaic properties of double-cable polymers SPJ with linear homopolymer of benzodithiophene (BDT) units and pendant PBI side groups. The donor backbone and acceptor side units are attachedvia a dodecyl linker. The SPJ based SCOSCs showed a PCE of 3.46%, a short-circuit current density (J_sc) of 7.55 mA/cm², a V_oc of 0.71 V and a fill factor (FF) of 0.64, while the chlorinated double-cable polymer SPJ-Cl provided an enhanced PCE of 3.57% mainly because of the significantly improved V_oc (0.85 V versus 0.71 V of SPJ).

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EXPERIMENTAL

All reagents and solvents were purchased from Aladdin, Energy Chemical, etc.; and used without further purification.

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Fabrication

The two polymers were applied as the photoactive layer for SCOSCs using an inverted configuration with ITO/ZnO and MoO₃ (10 nm)/Ag (100 nm) as the electrodes. The optimized condition was spin coating the polymer solution in chloroform with the concentration of 10 mg/mL with 1 vol% DIO as the processing additive, then thermal annealing at 150 °C for 10 min. Details could be found in the electronic supplementary information (ESI).

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Synthesis

Compounds 2−7 and monomers 8−10 for polymerization were synthesized according to the literature procedure.^[

14,19]

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Compound 8

¹H-NMR (400 MHz, chloroform-d, δ, ppm): 8.60 (m, 8H), 8.56–8.50 (m, 8H), 7.52 (s, 2H), 7.16 (d, J=4.4 Hz, 2H), 6.87 (d, J=4.4 Hz, 2H), 5.19 (m, 2H), 4.18 (t, J=6.4 Hz, 4H), 2.89 (t, J=7.6 Hz, 4H), 2.25 (m, 4H), 1.89−1.85 (m, 4H), 1.78−1.71 (m, 8H), 1.44-1.31 (m, 36H), 1.26-1.23 (m, 36H), 0.82 (t, J=6.8 Hz, 12H).

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SPJ

To a degassed solution of compound 8 (50.0 mg, 25.1 µmol), compound 9 (24.3 mg, 25.1 µmol) in toluene (3 mL) and DMF (0.3 mL), Pd(PPh₃)₄ (1.4 mg, 1.2 µmol) were added. The mixture was stirred at 115 °C for 48 h, then it was precipitated in methanol and filtered through a Soxhlet thimble. The polymer was extracted with acetone, hexane, dichloromethane, and chloroform. The chloroform was evaporated and the polymer was precipitated in acetone. The polymer was collected by filter and dried in a vacuum oven to yield SPJ (39 mg, 62%). M_n=13.1 kDa, M_w=32.1 kDa, and Đ_M=1.68.

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SPJ-Cl

The same procedure as for SPJ was used except that compound 8 (50.0 mg, 25.1 µmol) and compound 10 (26.1 mg, 25.1 µmol) were used as the monomers. Yield: 65%. M_n=11.1 kDa, M_w=31.0 kDa, and Đ_M=2.11.

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RESULTS AND DISCUSSION

Synthesis of the Conjugated Polymers

The synthetic procedures for the monomers and the two polymers are shown in Scheme 1. The monomers were synthesized according to the literatures.^[

14,19] The polymers SPJ and SPJ-Cl were synthesized via Stille polymerization using Pd(PPh₃)₄ as the catalyst. The molecular weight of the polymers was determined by GPC with CHCl₃ as eluent at 35 °C. As listed in Table 1, the polymer SPJ exhibits a number-average molecular weight (M_n) of 13.1 kDa with a polydispersity index (Đ_M) of 1.68, and SPJ-Cl shows a M_n of 11.3 kDa with a Đ_M of 2.11. Although the molecular weight of SPJ and SPJ-Cl are lower than the reported linear backbone-based double-cable conjugated polymers,^{[Reference 19

19]} the similar molecular weight and Đ_M could eliminate their effects on the photovoltaic performance and benefit for studying the effects of chlorination on the photovoltaic performance of the double-cable polymers.

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Fig 1 Synthesis routes to SPJ and SPJ-Cl.

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Table 1 Molecular weight and properties of the polymers.

Polymer	M_n (kDa)	Đ_M	HOMO (eV)	LUMO (eV)	${{E} }_{\rm{g} }^{\rm{opt} }$ (eV)
SPJ	13.1	1.68	−5.26	−3.41	2.03
SPJ-Cl	11.3	2.11	−5.40	−3.41	1.99

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Optical and Electrochemical Properties

UV-Vis absorption spectra of the double-cable polymer SPJ and SPJ-Cl in CHCl₃ solution and thin films are shown in Fig. 1. SPJ and SPJ-Cl show similar absorption spectra with two peaks at 492 and 527 nm in CHCl₃ solution which could be attributed to the linear backbone and large aromatic PBI side chains.^[

11,14] In thin film, the two polymers exhibit similar absorption with similar optical band gaps (E_g), revealing that the structure difference of SPJ and SPJ-Cl does not significantly affect the intramolecular and/or intermolecular interaction. The two peaks of the polymers slightly red-shift compared to those in solution, indicating stronger aggregation in thin films. After thermal annealing at 150 °C for 10 min in nitrogen-filled glovebox which is the optimal thermal-annealing condition, the absorption spectrum of SPJ is almost the same as that without thermal annealing. On the contrary, the absorption spectrum of SPJ-Cl slightly blue-shifts and the intensity of the peak at 533 nm significantly decreases, indicating that the thermal-annealing process decreases the aggregation of SPJ-Cl.

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Fig 1 (a) Normalized absorption spectra of SPJ and SPJ-Cl in CHCl₃ solution; (b) Normalized absorption spectra of SPJ (red lines) and SPJ-Cl (blue lines) films with (dash lines) or without (solid lines) thermal annealing at 150 °C for 10 min.

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Electrochemical Properties

The energy levels of SPJ and SPJ-Cl were determined by square wave (SWV) measurements and ferrocene was used as the internal standard (−4.8 eV).^[

62] The SWV curves are shown in Fig. 2. SPJ and SPJ-Cl exhibit similar the lowest unoccupied molecular orbital (LUMO) of −3.41 eV, and SPJ-Cl shows lower the highest occupied molecular orbital (HOMO) of −5.40 eV compared with that of SPJ (−5.26 eV). Unlike other chlorinated conjugated polymer donors or molecular photovoltaic materials,^{[Reference 44

44,Reference 60

60]} the chlorine atoms only downshift the HOMO energy levels of the double-cable polymers. This phenomenon is reasonable because in double-cable conjugated polymers the HOMO levels are determined by the donor backbones, while the LUMO levels mainly dominated by PBI side units.^{[Reference 19

19]} The deeper HOMO level of SPJ-Cl could be attributed to the inductive effect and the empty 3d orbital of chlorine atoms,^{[Reference 63

63,Reference 64

64]} and would benefit for a larger V_oc, thus a higher PCE.

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Fig 2 Square wave voltammetry curves of (a) SPJ and (b) SPJ-Cl.

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Photovoltaic Properties

These double-cable polymers were applied into SCOSCs with an inverted configuration of ITO/ZnO/polymer/MoO₃/Ag. Device optimization was conducted in terms of the active layer thickness, solvent additive and thermal annealing at different temperatures (Tables S1−S5 in ESI). The optimized photovoltaic performance could be obtained when using CF/DIO (1%) as the solvent, thermal annealing at 150 °C for 10 min when the thickness of the polymer is 50 nm. J-V characteristics and external quantum efficiencies (EQEs) spectra of the optimized SCOSCs are presented in Fig. 3 and the key parameters are summarized in Table 2. The SCOSCs based on SPJ exhibit a champion PCE of 3.46% with a J_sc of 7.55 mA/cm², a V_oc of 0.71 eV and an FF of 0.64. By comparison, the PCE is enhanced to 3.57% in SPJ-Cl-based SCOSCs with a higher V_oc of 0.85 V, a similar J_sc of 7.36 mA/cm², and a lower FF of 0.57. The SPJ based SCOSCs provided a similar with the reported PCE value (3.60%),^[

19] indicating that the effects of molecular weight on the photovoltaic performance of this SCOSCs is ignorable. The enhanced V_oc in SPJ-Cl based device, which is a common phenomenon for chlorinated donor materials,^{[Reference 14

14,Reference 33

33,Reference 62

62]} is related to the deeper HOMO level. The EQE spectra of the polymers are presented in Fig. 3(b). The SCOSCs based on SPJ and SPJ-Cl exhibit similar photoresponse region covering from 300 nm to 640 nm. However, the EQE spectrum of SPJ-Cl-based SCOSCs slightly blue shifts with a decreased EQE value in the region of 500−600 nm compared with that of SPJ-based SCOSCs, which is consistent with the absorption spectra of these polymers in films after thermal annealing as shown in Fig. 1(b). The SCOSCs based on SPJ-Cl show the maximum EQE value of 0.70 at 490 nm which is a little higher than that of SPJ (maximum EQEs value of 0.68 at 500 nm). As a result, the J_sc of SPJ-Cl-based SCOSCs (7.36 mA/cm²) is a little lower than that of SPJ-based SCOSCs (7.55 mA/cm²).

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Fig 3 (a) Current density-voltage (J-V) curves and (b) EQE spectra of SPJ and SPJ-Cl based SCOSCs.

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Table 2 Characteristics of optimized SCOSCs under AM 1.5G condition.

Active layer	V_oc (V)	J_sc (mA/cm²)	FF	PCE (%)	μ_h (cm²·V⁻¹·s⁻¹)
SPJ	0.71 (0.71±0.01)	7.55 (7.56±0.10)	0.64 (0.63±0.01)	3.46 (3.42±0.04)	3.78×10⁻⁴
SPJ-Cl	0.85 (0.85±0.01)	7.36 (7.27±0.10)	0.57 (0.57±0.01)	3.57 (3.53±0.03)	1.95×10⁻⁴

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The characteristics of the photocurrent density J_ph versus the effective voltage V_eff are plotted in Fig. 4(a) to study the exciton dissociation efficiency (η_diss). The η_diss of SPJ-based device is 98.2%, while the SPJ-Cl based device provides a little lower η_diss of 96.2%. In addition, the bimolecular recombination could be characterized via measuring the light intensity dependence of J_sc. Their relationship can be described by the power law equation: J_sc∝I_light^α. The less the bimolecular recombination is_, the closer α is to 1. The similar α indicates that low bimolecular recombination in the SCOSCs of SPJ and SPJ-Cl. However, the relatively smaller α value of SPJ-Cl-based SCOSCs indicates a little severer bimolecular recombination. Considering the similar photovoltaic response region, the relatively lower η_diss and severer bimolecular recombination results in the slightly smaller J_sc of SPJ-Cl-based SCOSCs.

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Fig 4 (a) Photocurrent density (J_ph) versus effective voltage (V_eff) curves of the devices; (b) J_sc-light intensity relationships.

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The charge mobility of SPJ and SPJ-Cl were measured by pace charge-limited current (SCLC) method (Fig. S1 in ESI). Unfortunately, only hole mobility could be obtained using hole-only devices with the structure of ITO/PEDOT:PSS/Active Layer/PFN-Br/Ag. The hole mobility of SPJ was calculated to be 3.78×10⁻⁴ cm²·V⁻¹·s⁻¹, which is nearly two times larger than SPJ-Cl (1.95×10⁻⁴ cm²·V⁻¹·s⁻¹). The higher hole mobility of SPJ-based device is consistent with the high J_sc and FF. The enhanced charge carrier mobility can be attributed to the strong aggregation of SPJ after thermal annealing, which is consistent with the absorption spectra as shown in Fig. 1(b) and is further proved by the atomic force microscopy (AFM) images as discussed vide infra.

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To further understand the surface morphology of these polymer thin films, AFM images were recorded. As seen in Fig. 5, both films showed fibrous structures, indicating ordered nanostructures. However, the fiber in the film of SPJ is coarser than that of SPJ-Cl. This results in a larger root-mean-square (RMS) of SPJ film (3.53 nm) than that of SPJ-Cl film (3.22 nm). The coarser nanofiber of SPJ thin films indicates stronger aggregation and larger phase separation, which is beneficial to the higher hole mobility and FF. However, the significant improvement in the V_oc of SPJ-Cl overcompensates for the slight reduction in J_sc and FF. As a result, chlorinated double-cable conjugated polymer SPJ-Cl exhibited higher PCE.

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Fig 5 AFM phase images of SPJ and SPJ-Cl films.

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CONCLUSIONS

In this work, the effect of chlorination at the conjugated side chains of double cable conjugated polymers on the photovoltaic performance of SCOSCs was studied. Since the pendant PBI groups determine the LUMO energy, the chlorination only lowers the HOMO level, which results in a significantly improved V_oc. After thermal annealing which benefit for improved PCE, the aggregation of chlorinated polymer SPJ-Cl decreases, thus the J_sc and FF slightly reduce. As a consequence, the chlorinated double-cable polymer SPJ-Cl based SCOSCs achieved a higher PCE of 3.57%. Our work demonstrates that chlorination is an effective method to improve the performance double-cable polymers for SCOSCs.

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摘要

In this work, the effects of chlorination in double cable conjugated polymers on the photovoltaic performance of SCOSCs were studied. The chlorination lowers the highest occupied molecular orbital level of the conjugated polymers, thus resulting in a higher open-circuit voltage and improved photovoltaic performance.

Abstract

关键词

Keywords

Double-cable conjugated polymerChlorinationSingle-component organic solar cells

references

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Roncali, J.; Grosu, I . The dawn of single material organic solar cells . Adv. Sci. , 2019 . 6 1801026 DOI:10.1002/advs.201801026http://doi.org/10.1002/advs.201801026 .

Yang, F.; Li, J.; Li, C.; Li, W . Improving electron transport in a double-cable conjugated polymer via parallel perylenetriimide design . Macromolecules , 2019 . 52 3689 -3696 . DOI:10.1021/acs.macromol.9b00495http://doi.org/10.1021/acs.macromol.9b00495 .

Liu, Z.; Wu, Y.; Zhang, Q.; Gao, X . Non-fullerene small molecule acceptors based on perylene diimides . J. Mater. Chem. A , 2016 . 4 17604 -17622 . DOI:10.1039/C6TA06978Ahttp://doi.org/10.1039/C6TA06978A .

Hwang, Y. J. ; Courtright, B. A. E. ; Ferreira, A. S. ; Tolbert, S. H. ; Jenekhe, S. A . 7.7% Efficient all-polymer solar cells . Adv. Mater. , 2015 . 27 4578 -4584 . DOI:10.1002/adma.201501604http://doi.org/10.1002/adma.201501604 .

Yang, Z.; Liang, S.; Liu, B.; Wang, J.; Yang, F.; Chen, Q.; Xiao, C.; Tang, Z.; Li, W . Incorporating semiflexible linkers into double-cable conjugated polymers via a click reaction . Polym. Chem. , 2021 . 12 6865 -6872 . DOI:10.1039/D1PY01188Jhttp://doi.org/10.1039/D1PY01188J .

Zhang, Q.; Kelly, M. A.; Bauer, N.; You, W . The curious case of fluorination of conjugated polymers for solar cells . Acc. Chem. Res. , 2017 . 50 2401 -2409 . DOI:10.1021/acs.accounts.7b00326http://doi.org/10.1021/acs.accounts.7b00326 .

Zhang, S.; Qin, Y.; Zhu, J.; Hou, J . Over 14% Efficiency in polymer solar cells enabled by a chlorinated polymer donor . Adv. Mater. , 2018 . 30 e1800868 DOI:10.1002/adma.201800868http://doi.org/10.1002/adma.201800868 .

Fan, Q.; Zhu, Q.; Xu, Z.; Su, W.; Chen, J.; Wu, J.; Guo, X.; Ma, W.; Zhang, M.; Li, Y . Chlorine substituted 2D-conjugated polymer for high-performance polymer solar cells with 13.1% efficiency via toluene processing . Nano Energy , 2018 . 48 413 -420 . DOI:10.1016/j.nanoen.2018.04.002http://doi.org/10.1016/j.nanoen.2018.04.002 .

Tang, A.; Song, W.; Xiao, B.; Guo, J.; Min, J.; Ge, Z.; Zhang, J.; Wei, Z.; Zhou, E . Benzotriazole-based acceptor and donors, coupled with chlorination, achieve a high VOC of 1.24 V and an efficiency of 10.5% in fullerene-free organic solar cells . Chem. Mater. , 2019 . 31 3941 -3947 . DOI:10.1021/acs.chemmater.8b05316http://doi.org/10.1021/acs.chemmater.8b05316 .

Yao, H.; Wang, J.; Xu, Y.; Zhang, S.; Hou, J . Recent progress in chlorinated organic photovoltaic materials . Acc. Chem. Res. , 2020 . 53 822 -832 . DOI:10.1021/acs.accounts.0c00009http://doi.org/10.1021/acs.accounts.0c00009 .

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Wuhan National Laboratory for Optoelectronics, Huazhong University of Science and Technology

School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology

Beijing Advanced Innovation Center for Soft Matter Science and Engineering & State Key Laboratory of Organic-Inorganic Composites, Beijing University of Chemical Technology

College of Basic Medicine, Hebei University

Department of Chemistry, School of Science, Beijing Jiaotong University

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