Triplet Acceptors with a D-A Structure and Twisted Conformation for Efficient Organic Solar Cells

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2020 May 10

PMID 32385920

Citations 6

Authors

Linqing Qin

Xingzheng Liu

Xin Zhang

Jianwei Yu

Lei Yang

Fenggui Zhao

Miaofei Huang

Kangwei Wang

Xiaoxi Wu

Yuhao Li

Hao Chen

Kai Wang

Jianlong Xia

Xinhui Lu

Feng Gao

Yuanping Yi

Hui Huang

Affiliations

Soon will be listed here.

Abstract

Triplet acceptors have been developed to construct high-performance organic solar cells (OSCs) as the long lifetime and diffusion range of triplet excitons may dissociate into free charges instead of net recombination when the energy levels of the lowest triplet state (T ) are close to those of charge-transfer states ( CT). The current triplet acceptors were designed by introducing heavy atoms to enhance the intersystem crossing, limiting their applications. Herein, two twisted acceptors without heavy atoms, analogues of Y6, constructed with large π-conjugated core and D-A structure, were confirmed to be triplet materials, leading to high-performance OSCs. The mechanism of triplet excitons were investigated to show that the twisted and D-A structures result in large spin-orbit coupling (SOC) and small energy gap between the singlet and triplet states, and thus efficient intersystem crossing. Moreover, the energy level of T is close to CT, facilitating the split of triplet exciton to free charges.

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References

Liu S, Zhang H, Li Y, Liu J, Du L, Chen M . Strategies to Enhance the Photosensitization: Polymerization and the Donor-Acceptor Even-Odd Effect. Angew Chem Int Ed Engl. 2018; 57(46):15189-15193. DOI: 10.1002/anie.201810326. View

Hou J, Inganas O, Friend R, Gao F . Organic solar cells based on non-fullerene acceptors. Nat Mater. 2018; 17(2):119-128. DOI: 10.1038/nmat5063. View

Yuan J, Wang R, Han G, Huang T, Huang W, Xue J . Rational Tuning of Molecular Interaction and Energy Level Alignment Enables High-Performance Organic Photovoltaics. Adv Mater. 2019; 31(43):e1904215. DOI: 10.1002/adma.201904215. View

Wadsworth A, Moser M, Marks A, Little M, Gasparini N, Brabec C . Critical review of the molecular design progress in non-fullerene electron acceptors towards commercially viable organic solar cells. Chem Soc Rev. 2018; 48(6):1596-1625. DOI: 10.1039/c7cs00892a. View

Vandewal K, Albrecht S, Hoke E, Graham K, Widmer J, Douglas J . Efficient charge generation by relaxed charge-transfer states at organic interfaces. Nat Mater. 2013; 13(1):63-8. DOI: 10.1038/nmat3807. View

Yuan J, Huang T, Cheng P, Zou Y, Zhang H, Yang J . Enabling low voltage losses and high photocurrent in fullerene-free organic photovoltaics. Nat Commun. 2019; 10(1):570. PMC: 6362024. DOI: 10.1038/s41467-019-08386-9. View

Meng L, Zhang Y, Wan X, Li C, Zhang X, Wang Y . Organic and solution-processed tandem solar cells with 17.3% efficiency. Science. 2018; 361(6407):1094-1098. DOI: 10.1126/science.aat2612. View

Chow P, Gelinas S, Rao A, Friend R . Quantitative bimolecular recombination in organic photovoltaics through triplet exciton formation. J Am Chem Soc. 2014; 136(9):3424-9. DOI: 10.1021/ja410092n. View

Uoyama H, Goushi K, Shizu K, Nomura H, Adachi C . Highly efficient organic light-emitting diodes from delayed fluorescence. Nature. 2012; 492(7428):234-8. DOI: 10.1038/nature11687. View

10.

Qian D, Zheng Z, Yao H, Tress W, Hopper T, Chen S . Design rules for minimizing voltage losses in high-efficiency organic solar cells. Nat Mater. 2018; 17(8):703-709. DOI: 10.1038/s41563-018-0128-z. View

11.

Yan T, Song W, Huang J, Peng R, Huang L, Ge Z . 16.67% Rigid and 14.06% Flexible Organic Solar Cells Enabled by Ternary Heterojunction Strategy. Adv Mater. 2019; 31(39):e1902210. DOI: 10.1002/adma.201902210. View

12.

Rao A, Chow P, Gelinas S, Schlenker C, Li C, Yip H . The role of spin in the kinetic control of recombination in organic photovoltaics. Nature. 2013; 500(7463):435-9. DOI: 10.1038/nature12339. View

13.

Zhang G, Zhao J, Chow P, Jiang K, Zhang J, Zhu Z . Nonfullerene Acceptor Molecules for Bulk Heterojunction Organic Solar Cells. Chem Rev. 2018; 118(7):3447-3507. DOI: 10.1021/acs.chemrev.7b00535. View

14.

Burrows H, Fernandes M, Seixas de Melo J, Monkman A, Navaratnam S . Characterization of the triplet state of tris(8-hydroxyquinoline)aluminium(III) in benzene solution. J Am Chem Soc. 2003; 125(50):15310-1. DOI: 10.1021/ja037254f. View

15.

Qian M, Zhang R, Hao J, Zhang W, Zhang Q, Wang J . Dramatic Enhancement of Power Conversion Efficiency in Polymer Solar Cells by Conjugating Very Low Ratio of Triplet Iridium Complexes to PTB7. Adv Mater. 2015; 27(23):3546-52. DOI: 10.1002/adma.201500730. View

16.

Zhao W, Cheung T, Jiang N, Huang W, Lam J, Zhang X . Boosting the efficiency of organic persistent room-temperature phosphorescence by intramolecular triplet-triplet energy transfer. Nat Commun. 2019; 10(1):1595. PMC: 6453937. DOI: 10.1038/s41467-019-09561-8. View

17.

Cui Y, Yao H, Zhang J, Zhang T, Wang Y, Hong L . Over 16% efficiency organic photovoltaic cells enabled by a chlorinated acceptor with increased open-circuit voltages. Nat Commun. 2019; 10(1):2515. PMC: 6555805. DOI: 10.1038/s41467-019-10351-5. View

18.

Xiong J, Jin K, Jiang Y, Qin J, Wang T, Liu J . Thiolactone copolymer donor gifts organic solar cells a 16.72% efficiency. Sci Bull (Beijing). 2023; 64(21):1573-1576. DOI: 10.1016/j.scib.2019.10.002. View

19.

Monkman A, Burrows H, Hartwell L, Horsburgh L, Hamblett I, Navaratnam S . Triplet energies of pi-conjugated polymers. Phys Rev Lett. 2001; 86(7):1358-61. DOI: 10.1103/PhysRevLett.86.1358. View

20.

Wang K, Zheng C, Liu W, Liang K, Shi Y, Tao S . Avoiding Energy Loss on TADF Emitters: Controlling the Dual Conformations of D-A Structure Molecules Based on the Pseudoplanar Segments. Adv Mater. 2017; 29(47). DOI: 10.1002/adma.201701476. View