J. Semicond. > 2021, Volume 42 > Issue 1 > 010502
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SHORT COMMUNICATION

D18, an eximious solar polymer!

Ke Jin, Zuo Xiao and Liming Ding

+ Author Affiliations

 Corresponding author: Z Xiao, xiaoz@nanoctr.cn; L Ding, ding@nanoctr.cn

DOI: 10.1088/1674-4926/42/1/010502

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Organic solar cell (OSC) is a promising photovoltaic technology with great commercialization potential due to the advantages like solution-processing, roll-to-roll fabrication, lightweight, flexibility, and semitransparency[1-7]. Conjugated polymer donors are key materials for OSCs[8]. Their functions include harvesting photons, constructing a 3D interpenetrating network in the active layer for efficient exciton dissociation, and transporting holes to the anode[9-11]. Copolymers containing fused-ring acceptor units (i.e. electron-accepting building blocks) are the most efficient type of donors for OSCs. The copolymer donors, such as Li’s J71[12] and PTQ10[13], Hou’s PBDB-T[14], PM6[15] and PM7[16], Sun’s PDBT-T1[17] and PBT1-C[18], Yu’s PTB7[19], Chen’s PTB7-Th[20], You’s FTAZ[21], Janssen’s PDPP3T[22], Yan’s PffBT4T-C9C13[23], Huang’s NT812[24] and P2F-EHp[25], Ding’s D18[26] and D18-Cl[27], all contain fused-ring acceptor units. The merits for fused-ring acceptor units are prominent: 1) the strong electron-withdrawing capability of these units gifts polymers deep HOMO (the highest occupied molecular orbital) levels, leading to high open-circuit voltage (Voc); 2) the rigid and extended molecular planes of these units gift polymers enhanced π–π stacking and good hole mobility, leading to high short-circuit current density (Jsc) and fill factor (FF). In the past decade, our group has been developing fused-ring-acceptor-unit-based polymer donors (Fig. 1).

Figure  1.  (Color online) Polymer donors with fused-ring acceptor units developed in Ding’s lab.
DownLoad: Full-Size Img PowerPoint

Fused-ring ketones are frequently-used acceptor units for polymer donors due to their strong electron-withdrawing property. In 2012, we reported donor–acceptor (D–A) copolymers P1[28] and P2[29] based on thiophene-fused ketone units benzo[1,2-b:4,5-c′]-dithiophene-4,8-dione and cyclopenta[2,1-b:3,4-c′]dithiophene-4-one, respectively. 4.33% and 2.20% PCEs were obtained from P1:PC61BM and P2:PC71BM solar cells, respectively. Fused-ring lactams are another important building blocks. The lactam moieties endow the unit with electron affinity and offer the sites for introducing alkyl chains to guarantee good solubility. In 2013, we first reported pentacyclic aromatic bislactam unit TPTI[30]. By copolymerizing TPTI with a thiophene unit, we got a donor PThTPTI. PThTPTI:PC71BM solar cells gave a PCE of 7.80% with a high Voc of 0.87 V. PThTPTI was among the best polymer donors at that time. Following this work, we designed a hexacyclic bislactam unit TD2 and used it to construct a selenophene-containing copolymer donor PSeTD2 in 2015[31]. Inverted PSeTD2:PC71BM solar cells offered a PCE of 8.18%, which was a record for D–A copolymers with selenophene as the donor unit. Later on, we designed a bislactam unit BDTP[32]. The structure of BDTP can be viewed as dividing TD2 into two tricyclic dithieno[3,2-b:2′,3′-d]pyridin-5(4H)-one (DTP) units and connecting them with a single bond. The D–A copolymer PThBDTP based on BDTP exhibited deep HOMO levels, good hole mobility and excellent performance in solar cells when blending with PC71BM. PThBDTP:PC71BM solar cells gave a PCE of 9.13% with a Voc of 0.96 V. PThBDTP was one of the few D–A copolymers with PCEs of over 9% at that time. After this work, we considered the tricyclic lactam DTP could be a useful building block for copolymer donors. In 2017, we reported a low-bandgap copolymer PDTP4TFBT based on DTP[33]. PDTP4TFBT is compatible not only with fullerene acceptors but also with nonfullerene acceptors. Blending PDTP4TFBT with the fullerene acceptor PC71BM or the nonfullerene acceptor ITIC[34] yielded 8.75% and 7.58% PCEs, respectively. The ternary cells based on PDTP4TFBT:PC71BM:ITIC (1 : 1.2 : 0.3) delivered a PCE of 9.20%. In 2018, we designed an analogue of DTP, thieno[3,2-c]isoquinolin-5(4H)-one (TIQ), by replacing one thiophene of DTP with a benzene[35]. TIQ-based D–A copolymer PTIQ4TFBT has a high hole mobility of 1.33 × 10–3 cm2 V–1 s–1 and gave a PCE of 10.16% in polymer:fullerene solar cells with an active layer thickness of 267 nm. Moreover, the thick-film PTIQ4TFBT solar cells kept over 8% PCE with active layer thickness over 500 nm. Regarding the rapid advance of nonfullerene acceptors in recent years, developing efficient donors matching nonfullerene acceptors became an imperative mission. Thus, we started focusing on the development of nonfullerene-acceptor-compatible polymer donors. In 2019, we reported a wide-bandgap copolymer PBD2T based on DTP[36]. Solar cells based on PBD2T and a nonfullerene acceptor IT-M[37] afforded PCEs up to 10.34%. The good performance of PBD2T stimulated our exploration for other fused-ring-acceptor-unit-based polymer donors. In the same year, we first reported the fused-ring-lactone-based polymer donors[38]. Thanks to the strong electron-withdrawing capability and rigid molecular plane of the tricyclic lactone unit 5H-dithieno[3,2-b:2′,3′-d]pyran-5-one, the resulting polymer L1 presents a deep HOMO level and good mobility. Inverted solar cells based on L1 and a nonfullerene acceptor Y6[39] gave PCEs up to 14.36%. Later on, we designed the tricyclic thiolactone unit 5H-dithieno[3,2-b:2′,3′-d]thiopyran-5-one (DTTP), and used it to synthesize the copolymer D16[40]. From L1 to D16, the simple replacement of lactone with thiolactone improves polymer π–π stacking. D16:Y6 solar cells gave PCEs up to 16.72% (certified 16.0%). In 2020, we designed copolymer D18 by using a fused-ring thiadiazole unit dithieno[3′,2′:3,4;2′′,3′′:5,6]benzo[1,2-c][1,2,5]thiadiazole (DTBT)[26]. Compared with DTTP, DTBT has a larger molecular plane and gifts D18 a high hole mobility of 1.59 × 10–3 cm2 V–1 s–1. D18:Y6 solar cells demonstrated an outstanding PCE of 18.22% (certified 17.6%), which was the highest efficiency for OSCs at that time. Recently, we reported a chlorinated analogue of D18, the D18-Cl[27]. D18-Cl also showed high performance in solar cells. Blending D18-Cl with a nonfullerene acceptor N3[41] yielded a PCE of 18.13% (certified 17.6%), demonstrating the great potential of cost-effective chlorinated polymer donors in OSCs. We also tried other fused-ring acceptor units with larger molecular planes to make polymer donors. In 2020, we reported a donor P3 based on a fused-ring phenazine unit 9,10-difluorodithieno[3,2-a:2′,3′-c]phenazine (FDTPz)[42]. P3:Y6 solar cells gave PCEs up to 15.14%, which is the highest efficiency from phenazine-based donors to date. In the same year, we reported polymer donors P4 and P5 based on two novel pentacyclic bislactone units, BL1 and BL2[43]. Compared with previous lactone units, BL1 and BL2 have stronger electron-withdrawing capability and gift P4 and P5 deeper HOMO levels. P4:IT-4F and P5:IT-4F solar cells gave high Vocs of 0.96 and 0.94 V, respectively, and PCEs of 10.44% and 7.31%, respectively.

Among all the polymer donors invented in our lab, D18 exhibited high hole mobility and outstanding performance. The grazing-incidence wide-angle X-ray scattering (GIWAXS) for D18 neat film or blend film shows distinct (001) and (002) diffraction peaks[44]. Besides common π–π stacking and lamellar stacking ordering, D18 also shows unusually strong backbone direction ordering. This may explain its excellent hole mobility and photovoltaic performance. The high hole mobility of D18 suggests that it could be applied in thick-film solar cells. Recently, we made thick-film solar cells by adding small amount of PC61BM into the D18:Y6 blend[45]. D18:Y6:PC61BM (1 : 1.6 : 0.2) solar cells afforded a PCE of 17.89% (certified 17.4%) at the thickness of 110 nm, and offered 16.32% and 16.19% PCEs at the thickness of 300 and 350 nm, respectively. To the best of our knowledge, this is the first report that OSCs gave over 16% PCEs with active layer thickness over 300 nm. To further explore the potential of D18, we screened a series of nonfullerene acceptors and found that N3 is a good partner for D18. The solar cells with a structure of ITO/PEDOT:PSS/D18:N3/PDIN/Ag delivered a PCE of 18.56%, with a Voc of 0.862 V, a Jsc of 27.44 mA cm–2 and a FF of 78.5% (Fig. S1), setting a new world record of PCE for organic solar cells. These cells have a D/A ratio of 1 : 1.6 (w/w), an active layer thickness of 121 nm and 0.15 vol% 1-chloronaphthalene (CN) as the additive (Tables S1–S3). D18:N3 solar cells presented >80% EQE at 450–810 nm, showing a maximum of 89% at 540 nm (Fig. S2). The integrated current density for D18:N3 solar cells is 26.61 mA cm –2. The best D18:N3 solar cells were also measured at the National Institute of Metrology (NIM) (Beijing), and a certified PCE of 17.9% was recorded (Voc, 0.850 V; Jsc, 26.71 mA cm–2; FF, 78.9%; effective area, 2.580 mm2) (Fig. 2).

Figure  2.  NIM (Beijing) report for D18:N3 solar cells.
DownLoad: Full-Size Img PowerPoint

Since 2010, we have been devoting our efforts in inventing fused-ring-acceptor-unit-based copolymer donors. Some copolymer donors present high performance not only in fullerene-acceptor-based solar cells but also in nonfullerene-acceptor-based solar cells. Among them, D18 demonstrates the highest PCE (18.56%) in OSCs. We are expecting that more innovative building blocks will be synthesized, and we believe more high-performance donors and acceptors are coming. With the innovative contribution and synergetic efforts from OSC community, OSC products will eventually go to market.

We thank the National Key Research and Development Program of China (2017YFA0206600), the National Natural Science Foundation of China (51773045, 21772030, 51922032 and 21961160720) and the Youth Association for Promoting Innovation (CAS) for financial support.

Appendix A. Supplementary materials

Supplementary materials to this article can be found online at https://doi.org/1674-4926/42/1/010502https://doi.org/1674-4926/42/1/010502.



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Fig. 1.  (Color online) Polymer donors with fused-ring acceptor units developed in Ding’s lab.

DownLoad: Full-Size Img PowerPoint
Fig. 2.  NIM (Beijing) report for D18:N3 solar cells.

DownLoad: Full-Size Img PowerPoint
[1]
Tong Y, Xiao Z, Du X, et al. Progress of the key materials for organic solar cells. Sci China Chem, 2020, 63, 758 doi: 10.1007/s11426-020-9726-0
[2]
Tong Y, Xiao Z, Du X, et al. Progress of the key materials for organic solar cells. Sci Sin Chim, 2020, 50, 437 doi: 10.1360/SSC-2020-0018
[3]
Duan C, Ding L. The new era for organic solar cells: non-fullerene small molecular acceptors. Sci Bull, 2020, 65, 1231 doi: 10.1016/j.scib.2020.04.030
[4]
Duan C, Ding L. The new era for organic solar cells: polymer donors. Sci Bull, 2020, 65, 1422 doi: 10.1016/j.scib.2020.04.044
[5]
Duan C, Ding L. The new era for organic solar cells: polymer acceptors. Sci Bull, 2020, 65, 1508 doi: 10.1016/j.scib.2020.05.023
[6]
Duan C, Ding L. The new era for organic solar cells: small molecular donors. Sci Bull, 2020, 65, 1597 doi: 10.1016/j.scib.2020.05.019
[7]
Zhang Y, Duan C, Ding L. Indoor organic photovoltaics. Sci Bull, 2020, 65, 2040 doi: 10.1016/j.scib.2020.08.030
[8]
Wu J, Cheng S, Cheng Y, et al. Donor-acceptor conjugated polymers based on multifused ladder-type arenes for organic solar cells. Chem Soc Rev, 2015, 44, 1113 doi: 10.1039/C4CS00250D
[9]
Müllen K, Pisula W. Donor-acceptor polymers. J Am Chem Soc, 2015, 137, 9503 doi: 10.1021/jacs.5b07015
[10]
Zhou H, Yang L, You W. Rational design of high performance conjugated polymers for organic solar cells. Macromolecules, 2012, 45, 607 doi: 10.1021/ma201648t
[11]
Yu G, Gao J, Hummelen J C. Polymer photovoltaic cells: enhanced efficiencies via a network of internal donor-acceptor heterojunctions. Science, 1995, 270, 1789 doi: 10.1126/science.270.5243.1789
[12]
Bin H, Gao L, Zhang Z G, et al. 11.4% efficiency non-fullerene polymer solar cells with trialkylsilyl substituted 2D-conjugated polymer as donor. Nat Commun, 2016, 7, 13651 doi: 10.1038/ncomms13651
[13]
Sun C, Pan F, Bin H, et al. A low cost and high performance polymer donor material for polymer solar cells. Nat Commun, 2018, 9, 743 doi: 10.1038/s41467-018-03207-x
[14]
Qian D, Ye L, Zhang M, et al. Design, application, and morphology study of a new photovoltaic polymer with strong aggregation in solution state. Macromolecules, 2012, 45, 9611 doi: 10.1021/ma301900h
[15]
Zhang M, Guo X, Ma W, et al. A large-bandgap conjugated polymer for versatile photovoltaic applications with high performance. Adv Mater, 2015, 27, 4655 doi: 10.1002/adma.201502110
[16]
Zhang S, Qin Y, Zhu J, et al. Over 14% efficiency in polymer solar cells enabled by a chlorinated polymer donor. Adv Mater, 2018, 30, 1800868 doi: 10.1002/adma.201800868
[17]
Huo L, Liu T, Sun X, et al. Single-junction organic solar cells based on a novel wide-bandgap polymer with efficiency of 9.7%. Adv Mater, 2015, 27, 2938 doi: 10.1002/adma.201500647
[18]
Liu T, Huo L, Chandrabose S, et al. Optimized fibril network morphology by precise side-chain engineering to achieve high-performance bulk-heterojunction organic solar cells. Adv Mater, 2018, 30, 1707353 doi: 10.1002/adma.201707353
[19]
Liang Y, Xu Z, Xia J, et al. For the bright future-bulk heterojunction polymer solar cells with power conversion efficiency of 7.4%. Adv Mater, 2010, 22, E135 doi: 10.1002/adma.200903528
[20]
Liao S H, Jhuo H J, Cheng Y S, et al. Fullerene derivative-doped zinc oxide nanofilm as the cathode of inverted polymer solar cells with low-bandgap polymer (PTB7-Th) for high performance. Adv Mater, 2013, 25, 4766 doi: 10.1002/adma.201301476
[21]
Price S C, Stuart A C, Yang L, et al. Fluorine substituted conjugated polymer of medium band gap yields 7% efficiency in polymer-fullerene solar cells. J Am Chem Soc, 2011, 133, 4625 doi: 10.1021/ja1112595
[22]
Hendriks K H, Heintges G H L, Gevaerts V S, et al. High-molecular-weight regular alternating diketopyrrolopyrrole-based terpolymers for efficient organic solar cells. Angew Chem, 2013, 125, 8499 doi: 10.1002/ange.201302319
[23]
Zhao J, Li Y, Yang G, et al. Efficient organic solar cells processed from hydrocarbon solvents. Nat Energy, 2016, 1, 15027 doi: 10.1038/nenergy.2015.27
[24]
Jin Y, Chen Z, Dong S, et al. A novel naphtho[1,2-c:5,6-c']bis([1,2,5]thiadiazole)-based narrow-bandgap π-conjugated polymer with power conversion efficiency over 10%. Adv Mater, 2016, 28, 9811 doi: 10.1002/adma.201603178
[25]
Fan B, Zhang D, Li M, et al. Achieving over 16% efficiency for single-junction organic solar cells. Sci China Chem, 2019, 62, 746 doi: 10.1007/s11426-019-9457-5
[26]
Liu Q, Jiang Y, Jin K, et al. 18% efficiency organic solar cells. Sci Bull, 2020, 65, 272 doi: 10.1016/j.scib.2020.01.001
[27]
Qin J, Zhang L, Zuo C, et al. A chlorinated copolymer donor demonstrates a 18.13% power conversion efficiency. J Semicond, 2021, 42, 010501 doi: 10.1088/1674-4926/42/1/010501
[28]
Cao J, Zhang W, Xiao Z, et al. Synthesis and photovoltaic properties of low band gap polymers containing benzo[1,2-b:4,5-c′]dithiophene-4,8-dione. Macromolecules, 2012, 45, 1710 doi: 10.1021/ma202578y
[29]
Zhang W, Cao J, Liu Y, et al. Using cyclopenta[2,1-b:3,4-c']dithiophene-4-one as a building block for low-bandgap conjugated copolymers applied in solar cells. Macromol Rapid Commun, 2012, 33, 1574 doi: 10.1002/marc.201200311
[30]
Cao J, Liao Q, Du X, et al. A pentacyclic aromatic lactam building block for efficient polymer solar cells. Energy Environ Sci, 2013, 6, 3224 doi: 10.1039/c3ee41948g
[31]
Cao J, Zuo C, Du B, et al. Hexacyclic lactam building blocks for highly efficient polymer solar cells. Chem Commun, 2015, 51, 12122 doi: 10.1039/C5CC04375A
[32]
Cao J, Qian L, Lu F, et al. A lactam building block for efficient polymer solar cells. Chem Commun, 2015, 51, 11830 doi: 10.1039/C5CC03620H
[33]
An M, Xie F, Geng X, et al. A high-performance D-A copolymer based on dithieno[3,2-b:2′,3′-d]pyridin-5(4H)-one unit compatible with fullerene and nonfullerene acceptors in solar cells. Adv Energy Mater, 2017, 7, 1602509 doi: 10.1002/aenm.201602509
[34]
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    Ke Jin, Zuo Xiao, Liming Ding. D18, an eximious solar polymer![J]. Journal of Semiconductors, 2021, 42(1): 010502. doi: 10.1088/1674-4926/42/1/010502
    K Jin, Z Xiao, L M Ding, D18, an eximious solar polymer![J]. J. Semicond., 2021, 42(1): 010502. doi: 10.1088/1674-4926/42/1/010502.
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    Received: 26 December 2020 Revised: Online: Accepted Manuscript: 26 December 2020Uncorrected proof: 28 December 2020Published: 09 January 2021

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      Article Navigation >  Journal of Semiconductors  > 2021  >  42(1): 010502
      Ke Jin, Zuo Xiao, Liming Ding. D18, an eximious solar polymer![J]. Journal of Semiconductors, 2021, 42(1): 010502. doi: 10.1088/1674-4926/42/1/010502 ****K Jin, Z Xiao, L M Ding, D18, an eximious solar polymer![J]. J. Semicond., 2021, 42(1): 010502. doi: 10.1088/1674-4926/42/1/010502.
      Citation:
      Ke Jin, Zuo Xiao, Liming Ding. D18, an eximious solar polymer![J]. Journal of Semiconductors, 2021, 42(1): 010502. doi: 10.1088/1674-4926/42/1/010502 ****
      K Jin, Z Xiao, L M Ding, D18, an eximious solar polymer![J]. J. Semicond., 2021, 42(1): 010502. doi: 10.1088/1674-4926/42/1/010502.
      shu

      D18, an eximious solar polymer!

      DOI: 10.1088/1674-4926/42/1/010502

      • Center for Excellence in Nanoscience (CAS), Key Laboratory of Nanosystem and Hierarchical Fabrication (CAS), National Center for Nanoscience and Technology, Beijing 100190, China

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      • Ke Jin：got his MS degree from Wuhan Institute of Technology in 2019. Now he is a research assistant in Liming Ding Group at National Center for Nanoscience and Technology. His current research focuses on organic solar cells
      • Zuo Xiao：got his BS and PhD degrees from Peking University under the supervision of Prof. Liangbing Gan. He did postdoctoral research in Eiichi Nakamura Lab at the University of Tokyo. In March 2011, he joined Liming Ding Group at National Center for Nanoscience and Technology as an associate professor. In April 2020, he was promoted to be a full professor. His current research focuses on organic solar cells
      • Liming Ding：got his PhD from University of Science and Technology of China (was a joint student at Changchun Institute of Applied Chemistry, CAS). He started his research on OSCs and PLEDs in Olle Inganäs Lab in 1998. Later on, he worked at National Center for Polymer Research, Wright-Patterson Air Force Base and Argonne National Lab (USA). He joined Konarka as a Senior Scientist in 2008. In 2010, he joined National Center for Nanoscience and Technology as a full professor. His research focuses on functional materials and devices. He is RSC Fellow, the nominator for Xplorer Prize, and the Associate Editors for Science Bulletin and Journal of Semiconductors
      • Corresponding author: Z Xiao, xiaoz@nanoctr.cn; L Ding, ding@nanoctr.cn
      • Received Date: 2020-12-26
      • Published Date: 2021-01-10

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