稠环电子受体光伏材料
|
摘要
基于非富勒烯受体的有机太阳能电池是化学和材料领域的热点前沿之一,中国领跑这个热点前沿.中国学者在非富勒烯受体材料方面取得了一系列重要的创新成果.我们提出了"稠环电子受体(FREA)"这一新概念,构建了高性能稠环电子受体新体系,发明了明星分子ITIC.我们的原创性工作引起了国内外同行的广泛关注和跟进.目前,基于稠环电子受体的有机太阳能电池效率已达到13%~14%,超过富勒烯体系.ITIC等稠环电子受体的出现颠覆了富勒烯受体在有机太阳能电池领域的统治地位,开创了有机太阳能电池的非富勒烯时代.本文简要评述了我们在高性能稠环电子受体设计与器件应用中的研究进展,并展望稠环电子受体的未来发展.
Nonfullerene organic solar cell(OPV) is one of the hottest frontiers in chemistry and materials science. China has been leading this hot frontier, and Chinese researchers have made great contribution to this research field. We proposed a novel concept — fused-ring electron acceptor(FREA), established a brand-new, high-performance nonfullerene acceptor system, and invented star molecule ITIC. These FREAs show some advantages:(1) they have high electron mobility similar to those of fullerenes;(2) they exhibit strong and broad absorption, especially in the 700 – 1000 nm range, and can match with wide-bandgap donor materials to achieve complementary absorption;(3) their energy level can be tuned and thus they match with various high-performance electron donors;(4) their crystallinity and film morphology can be tuned;(5) their synthesis is easy to scale up. Our original and pioneering work has received extensive attention. FREAs are now commercial available. Many well-known research groups across the world have already utilized these FREAs to fabricate high-efficiency OPV. FREA-based OPV now has achieved a power conversation efficiency of 13%-14%, surpassing the fullerene counterpart. Moreover, the FREA-based OPV exhibits better device stability than the fullerene-based counterpart. The emergence of ITIC-like FREAs has overturned predominant position of fullerene acceptor in OPV and is inaugurating the nonfullerene OPV era. In this review, we summarize our progress of FREA design and application in OPV, and give an outlook of the FREAs. We first introduce the background information, concept and working mechanism of OPV; then the advantages and disadvantages of fullerene acceptors are compared with nonfullerene acceptors; and the concept and merits of FREAs are finally discussed. The main text focuses on fused-ring core engineering, electron-withdrawing group engineering and side chain engineering, and we emphasize effects of electron-donating fused-ring cores, electron-withdrawing end groups and side chains on solubility, crystallinity, energy levels, absorption spectra, electron mobilities and photovoltaic properties of FREAs.
Nonfullerene organic solar cell(OPV) is one of the hottest frontiers in chemistry and materials science. China has been leading this hot frontier, and Chinese researchers have made great contribution to this research field. We proposed a novel concept — fused-ring electron acceptor(FREA), established a brand-new, high-performance nonfullerene acceptor system, and invented star molecule ITIC. These FREAs show some advantages:(1) they have high electron mobility similar to those of fullerenes;(2) they exhibit strong and broad absorption, especially in the 700 – 1000 nm range, and can match with wide-bandgap donor materials to achieve complementary absorption;(3) their energy level can be tuned and thus they match with various high-performance electron donors;(4) their crystallinity and film morphology can be tuned;(5) their synthesis is easy to scale up. Our original and pioneering work has received extensive attention. FREAs are now commercial available. Many well-known research groups across the world have already utilized these FREAs to fabricate high-efficiency OPV. FREA-based OPV now has achieved a power conversation efficiency of 13%-14%, surpassing the fullerene counterpart. Moreover, the FREA-based OPV exhibits better device stability than the fullerene-based counterpart. The emergence of ITIC-like FREAs has overturned predominant position of fullerene acceptor in OPV and is inaugurating the nonfullerene OPV era. In this review, we summarize our progress of FREA design and application in OPV, and give an outlook of the FREAs. We first introduce the background information, concept and working mechanism of OPV; then the advantages and disadvantages of fullerene acceptors are compared with nonfullerene acceptors; and the concept and merits of FREAs are finally discussed. The main text focuses on fused-ring core engineering, electron-withdrawing group engineering and side chain engineering, and we emphasize effects of electron-donating fused-ring cores, electron-withdrawing end groups and side chains on solubility, crystallinity, energy levels, absorption spectra, electron mobilities and photovoltaic properties of FREAs.
引文
1 Li Y.Acc Chem Res,2012,45(5):723-733
2 Chen J,Cao Y.Acc Chem Res,2009,42(11):1709-718
3 Cheng P,Zhan X.Chem Soc Rev,2016,45(9):2544-2582
4 Zhan X,Zhu D.Polym Chem,2010,1(4):409-419
5 Lin Y,Li Y,Zhan X.Chem Soc Rev,2012,41(11):4245-4272
6 Zhao X,Zhan X.Chem Soc Rev,2011,40(7):3728-3743
7 Chen Y,Wan X,Long G.Acc Chem Res,2013,46(11):2645-2655
8 Lin Y,Zhan X.Acc Chem Res,2016,49(2):175-183
9 Ye L,Zhang S,Huo L,Zhang M,Hou J.Acc Chem Res,2014,47(5):1595-1603
10 Cheng P,Zhan X.Mater Horiz,2015,2(5):462-485
11 Xu B,Wang C,Ma W,Liu L,Xie Z,Ma Y.J Phys Chem C,2017,121(10):5498-5502
12 Price S C,Stuart A C,Yang L,Zhou H,You W.J Am Chem Soc,2011,133(12):4625-4631
13 Min J,Zhang Z G,Zhang S,Li Y.Chem Mater,2012,24(16):3247-3254
14 Huo L,Liu T,Sun X,Cai Y,Heeger A J,Sun Y.Adv Mater,2015,27(18):2938-2944
15 Zhao W,Qian D,Zhang S,Li S,Inganas O,Gao F,Hou J.Adv Mater,2016,28(23):4734-4739
16 Liao S H,Jhuo H J,Cheng Y S,Chen S A.Adv Mater,2013,25(34):4766-4771
17 Zhan X,Tan Z A,Domercq B,An Z,Zhang X,Barlow S,Li Y,Zhu D,Kippelen B,Marder S R.J Am Chem Soc,2007,129(23):7246-7247
18 Zhan X,Tan Z A,Zhou E J,Li Y F,Misra R,Grant A,Domercq B,Zhang X H,An Z S,Zhang X,Barlow S,Kippelen B,Marder S R.J Mater Chem,2009,19(32):5794-5803
19 Dai S,Cheng P,Lin Y,Wang Y,Ma L,Ling Q,Zhan X.Polym Chem,2015,6(29):5254-5263
20 Dai S,Huang S,Yu H,Ling Q,Zhan X.J Polym Sci,Part A:Polym Chem,2017,55(4):682-689
21 Dai S,Lin Y,Cheng P,Wang Y,Zhao X,Ling Q,Zhan X.Dyes Pigments,2015,114:283-289
22 Dai S,Zhang S,Ling Q,Zhan X.Chinese J Polym Sci,2016,35(2):230-238
23 Wang J,Yao Y,Dai S,Zhang X,Wang W,He Q,Han L,Lin Y,Zhan X.J Mater Chem A,2015,3(24):13000-13010
24 Lin Y,Wang J,Dai S,Li Y,Zhu D,Zhan X.Adv Energy Mater,2014,4(13):1400420
25 Zhan X,Facchetti A,Barlow S,Marks T,Ratner M,Wasielewski M,Marder S.Adv Mater,2011,23(2):268-284
26 Lin Y,Wang Y,Wang J,Hou J,Li Y,Zhu D,Zhan X.Adv Mater,2014,26(30):5137-5142
27 Cheng P,Zhao X,Zhou W,Hou J,Li Y,Zhan X.Org Electron,2014,15(10):2270-2276
28 Cheng P,Ye L,Zhao X,Hou J,Li Y,Zhan X.Energy Environ Sci,2014,7(4):1351-1356
29 Lin Y,Cheng P,Li Y,Zhan X.Chem Commun,2012,48(39):4773-4775
30 Lin Y Z,Ma L C,Li Y F,Liu Y Q,Zhu D B,Zhan X.Adv Energy Mater,2013,3(9):1166-1170
31 Li T F,Wang J Y,Chen H,Cheng P,Huang S,Lin Y Z,Yu H F,Zhan X.Dyes Pigments,2017,137:553-559
32 Dou C D,Long X J,Ding Z C,Xie Z Y,Liu J,Wang L X.Angew Chem Int Ed,2016,55(4):1436-1440
33 Lin Y,Wang J,Zhang Z,Bai H,Li Y,Zhu D,Zhan X.Adv Mater,2015,27(7):1170-1174
34 Lin Y,Zhan X.Adv Energy Mater,2015,5(20):1501063
35 Lin Y,Li T,Zhao F,Han L,Wang Z,Wu Y,He Q,Wang J,Huo L,Sun Y,Wang C,Ma W,Zhan X.Adv Energy Mater,2016,6(18):1600854
36 Zhao W,Qian D,Zhang S,Li S,Inganas O,Gao F,Hou J.Adv Mater,2016,28(23):4734-4739
37 Bin H,Gao L,Zhang Z G,Yang Y,Zhang Y,Zhang C,Chen S,Xue L,Yang C,Xiao M,Li Y.Nat Commun,2016,7:13651
38 Dai S,Zhao F,Zhang Q,Lau T,Li T,Liu K,Ling Q,Wang C,Lu X,You W,Zhan X.J Am Chem Soc,2017,139(3):1336-1343
39 Wang W,Yan C,Lau T K,Wang J,Liu K,Fan Y,Lu X,Zhan X.Adv Mater,2017,29:1701308
40 Lin Y,He Q,Zhao F,Huo L,Mai J,Lu X,Su C J,Li T,Wang J,Zhu J,Sun Y,Wang C,Zhan X.J Am Chem Soc,2016,138(9):2973-2976
41 Lin Y,Zhao F,Wu Y,Chen K,Xia Y,Li G,Prasad S K,Zhu J,Huo L,Bin H,Zhang Z G,Guo X,Zhang M,Sun Y,Gao F,Wei Z,Ma W,Wang C,Hodgkiss J,Bo Z,Inganas O,Li Y,Zhan X.Adv Mater,2017,29(3):1604155
42 Lin Y,Zhao F,He Q,Huo L,Wu Y,Parker T,Ma W,Sun Y,Wang C,Zhu D,Heeger A J,Marder S R,Zhan X.J Am Chem Soc,2016,138(14):4955-4961
43 Wang J,Wang W,Wang X,Wu Y,Zhang Q,Yan C,Ma W,You W,Zhan X.Adv Mater,2017,29:1702125
44 Bai H,Cheng P,Wang Y,Ma L,Li Y,Zhu D,Zhan X.J Mater Chem A,2014,2(3):778-784
45 Wu Y,Bai H,Wang Z,Cheng P,Zhu S,Wang Y,Ma W,Zhan X.Energy Environ Sci,2015,8(11):3215-3221
46 Bai H T,Wu Y,Wang Y F,Wu Y,Li R,Cheng P Y,Zhang M Y,Wang J Y,Ma W,Zhan X.J Mater Chem A,2015,3(41):20758-20766
47 Bai H T,Wang Y F,Cheng P,Wang J Y,Wu Y,Hou J H,Zhan X.J Mater Chem A,2015,3(5):1910-1914
48 Cheng P,Zhang M Y,Lau T K,Wu Y,Jia B Y,Wang J Y,Yan C Q,Qin M,Lu X H,Zhan X.Adv Mater,2017,29(11):1605216
49 Jia B Y,Wu Y,Zhao F W,Yan C Q,Zhu S Y,Cheng P,Mai J Q,Lau T K,Lu X H,Su C J,Wang C R,Zhan X.Sci China Chem,2017,60(2):257-263
50 Zhao F,Dai S,Wu Y,Zhang Q,Wang J,Jiang L,Ling Q,Wei Z,Ma W,You W,Wang C,Zhan X.Adv Mater,2017,29(18):1700144
51 Lin Y,Zhang Z G,Bai H,Wang J,Yao Y,Li Y,Zhu D,Zhan X.Energy Environ Sci,2015,8(2):610-616
52 Wang Y F,Bai H T,Zhan X W.J Energy Chem,2015,24(6):744-749
53 Yan C Q,Wu Y,Wang J Y,Li R,Cheng P,Bai H T,Zhan Z Q,Ma W,Zhan X.Dyes Pigments,2017,139:627-634
54 Zhao W,Li S,Yao H,Zhang S,Zhang Y,Yang B,Hou J.J Am Chem Soc,2017,139(21):7148-7151
55 Bin H,Zhang Z G,Gao L,Chen S,Zhong L,Xue L,Yang C,Li Y.J Am Chem Soc,2016,138(13):4657-4664
2 Chen J,Cao Y.Acc Chem Res,2009,42(11):1709-718
3 Cheng P,Zhan X.Chem Soc Rev,2016,45(9):2544-2582
4 Zhan X,Zhu D.Polym Chem,2010,1(4):409-419
5 Lin Y,Li Y,Zhan X.Chem Soc Rev,2012,41(11):4245-4272
6 Zhao X,Zhan X.Chem Soc Rev,2011,40(7):3728-3743
7 Chen Y,Wan X,Long G.Acc Chem Res,2013,46(11):2645-2655
8 Lin Y,Zhan X.Acc Chem Res,2016,49(2):175-183
9 Ye L,Zhang S,Huo L,Zhang M,Hou J.Acc Chem Res,2014,47(5):1595-1603
10 Cheng P,Zhan X.Mater Horiz,2015,2(5):462-485
11 Xu B,Wang C,Ma W,Liu L,Xie Z,Ma Y.J Phys Chem C,2017,121(10):5498-5502
12 Price S C,Stuart A C,Yang L,Zhou H,You W.J Am Chem Soc,2011,133(12):4625-4631
13 Min J,Zhang Z G,Zhang S,Li Y.Chem Mater,2012,24(16):3247-3254
14 Huo L,Liu T,Sun X,Cai Y,Heeger A J,Sun Y.Adv Mater,2015,27(18):2938-2944
15 Zhao W,Qian D,Zhang S,Li S,Inganas O,Gao F,Hou J.Adv Mater,2016,28(23):4734-4739
16 Liao S H,Jhuo H J,Cheng Y S,Chen S A.Adv Mater,2013,25(34):4766-4771
17 Zhan X,Tan Z A,Domercq B,An Z,Zhang X,Barlow S,Li Y,Zhu D,Kippelen B,Marder S R.J Am Chem Soc,2007,129(23):7246-7247
18 Zhan X,Tan Z A,Zhou E J,Li Y F,Misra R,Grant A,Domercq B,Zhang X H,An Z S,Zhang X,Barlow S,Kippelen B,Marder S R.J Mater Chem,2009,19(32):5794-5803
19 Dai S,Cheng P,Lin Y,Wang Y,Ma L,Ling Q,Zhan X.Polym Chem,2015,6(29):5254-5263
20 Dai S,Huang S,Yu H,Ling Q,Zhan X.J Polym Sci,Part A:Polym Chem,2017,55(4):682-689
21 Dai S,Lin Y,Cheng P,Wang Y,Zhao X,Ling Q,Zhan X.Dyes Pigments,2015,114:283-289
22 Dai S,Zhang S,Ling Q,Zhan X.Chinese J Polym Sci,2016,35(2):230-238
23 Wang J,Yao Y,Dai S,Zhang X,Wang W,He Q,Han L,Lin Y,Zhan X.J Mater Chem A,2015,3(24):13000-13010
24 Lin Y,Wang J,Dai S,Li Y,Zhu D,Zhan X.Adv Energy Mater,2014,4(13):1400420
25 Zhan X,Facchetti A,Barlow S,Marks T,Ratner M,Wasielewski M,Marder S.Adv Mater,2011,23(2):268-284
26 Lin Y,Wang Y,Wang J,Hou J,Li Y,Zhu D,Zhan X.Adv Mater,2014,26(30):5137-5142
27 Cheng P,Zhao X,Zhou W,Hou J,Li Y,Zhan X.Org Electron,2014,15(10):2270-2276
28 Cheng P,Ye L,Zhao X,Hou J,Li Y,Zhan X.Energy Environ Sci,2014,7(4):1351-1356
29 Lin Y,Cheng P,Li Y,Zhan X.Chem Commun,2012,48(39):4773-4775
30 Lin Y Z,Ma L C,Li Y F,Liu Y Q,Zhu D B,Zhan X.Adv Energy Mater,2013,3(9):1166-1170
31 Li T F,Wang J Y,Chen H,Cheng P,Huang S,Lin Y Z,Yu H F,Zhan X.Dyes Pigments,2017,137:553-559
32 Dou C D,Long X J,Ding Z C,Xie Z Y,Liu J,Wang L X.Angew Chem Int Ed,2016,55(4):1436-1440
33 Lin Y,Wang J,Zhang Z,Bai H,Li Y,Zhu D,Zhan X.Adv Mater,2015,27(7):1170-1174
34 Lin Y,Zhan X.Adv Energy Mater,2015,5(20):1501063
35 Lin Y,Li T,Zhao F,Han L,Wang Z,Wu Y,He Q,Wang J,Huo L,Sun Y,Wang C,Ma W,Zhan X.Adv Energy Mater,2016,6(18):1600854
36 Zhao W,Qian D,Zhang S,Li S,Inganas O,Gao F,Hou J.Adv Mater,2016,28(23):4734-4739
37 Bin H,Gao L,Zhang Z G,Yang Y,Zhang Y,Zhang C,Chen S,Xue L,Yang C,Xiao M,Li Y.Nat Commun,2016,7:13651
38 Dai S,Zhao F,Zhang Q,Lau T,Li T,Liu K,Ling Q,Wang C,Lu X,You W,Zhan X.J Am Chem Soc,2017,139(3):1336-1343
39 Wang W,Yan C,Lau T K,Wang J,Liu K,Fan Y,Lu X,Zhan X.Adv Mater,2017,29:1701308
40 Lin Y,He Q,Zhao F,Huo L,Mai J,Lu X,Su C J,Li T,Wang J,Zhu J,Sun Y,Wang C,Zhan X.J Am Chem Soc,2016,138(9):2973-2976
41 Lin Y,Zhao F,Wu Y,Chen K,Xia Y,Li G,Prasad S K,Zhu J,Huo L,Bin H,Zhang Z G,Guo X,Zhang M,Sun Y,Gao F,Wei Z,Ma W,Wang C,Hodgkiss J,Bo Z,Inganas O,Li Y,Zhan X.Adv Mater,2017,29(3):1604155
42 Lin Y,Zhao F,He Q,Huo L,Wu Y,Parker T,Ma W,Sun Y,Wang C,Zhu D,Heeger A J,Marder S R,Zhan X.J Am Chem Soc,2016,138(14):4955-4961
43 Wang J,Wang W,Wang X,Wu Y,Zhang Q,Yan C,Ma W,You W,Zhan X.Adv Mater,2017,29:1702125
44 Bai H,Cheng P,Wang Y,Ma L,Li Y,Zhu D,Zhan X.J Mater Chem A,2014,2(3):778-784
45 Wu Y,Bai H,Wang Z,Cheng P,Zhu S,Wang Y,Ma W,Zhan X.Energy Environ Sci,2015,8(11):3215-3221
46 Bai H T,Wu Y,Wang Y F,Wu Y,Li R,Cheng P Y,Zhang M Y,Wang J Y,Ma W,Zhan X.J Mater Chem A,2015,3(41):20758-20766
47 Bai H T,Wang Y F,Cheng P,Wang J Y,Wu Y,Hou J H,Zhan X.J Mater Chem A,2015,3(5):1910-1914
48 Cheng P,Zhang M Y,Lau T K,Wu Y,Jia B Y,Wang J Y,Yan C Q,Qin M,Lu X H,Zhan X.Adv Mater,2017,29(11):1605216
49 Jia B Y,Wu Y,Zhao F W,Yan C Q,Zhu S Y,Cheng P,Mai J Q,Lau T K,Lu X H,Su C J,Wang C R,Zhan X.Sci China Chem,2017,60(2):257-263
50 Zhao F,Dai S,Wu Y,Zhang Q,Wang J,Jiang L,Ling Q,Wei Z,Ma W,You W,Wang C,Zhan X.Adv Mater,2017,29(18):1700144
51 Lin Y,Zhang Z G,Bai H,Wang J,Yao Y,Li Y,Zhu D,Zhan X.Energy Environ Sci,2015,8(2):610-616
52 Wang Y F,Bai H T,Zhan X W.J Energy Chem,2015,24(6):744-749
53 Yan C Q,Wu Y,Wang J Y,Li R,Cheng P,Bai H T,Zhan Z Q,Ma W,Zhan X.Dyes Pigments,2017,139:627-634
54 Zhao W,Li S,Yao H,Zhang S,Zhang Y,Yang B,Hou J.J Am Chem Soc,2017,139(21):7148-7151
55 Bin H,Zhang Z G,Gao L,Chen S,Zhong L,Xue L,Yang C,Li Y.J Am Chem Soc,2016,138(13):4657-4664