Design and synthesis of carbonyl group modified conjugated polymers for photovoltaic application

Polymer Bulletin

Volumn 68, Issue 7, 2012, Pages 1867-1877

  Shi, Minmin ^a   Fu, Lei ^a   Hu, Xiaolian ^a   Zuo, Lijian ^a   Deng, Dan ^a   Chen, Jian ^a   Chen, Hongzheng ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

Carbonyl group; Conjugated polymer; Polymer solar cells

Indexed keywords

ALTERNATING COPOLYMERIZATION; BENZODITHIOPHENE; BULK HETEROJUNCTION SOLAR CELLS; CARBONYL GROUPS; DONOR-ACCEPTORS; ELECTRON ACCEPTOR; ELECTRON DONORS; ELECTRON-ACCEPTING; ELECTRON-DONATING; ELECTRONWITHDRAWING; FILL FACTOR; HIGH PERFORMANCE POLYMER; HIGHEST OCCUPIED MOLECULAR ORBITAL ENERGY LEVELS; METHYL ESTERS; MOLECULAR DESIGN; PHOTOVOLTAIC APPLICATIONS; PHOTOVOLTAIC PERFORMANCE; POLYMER SOLAR CELLS; POWER CONVERSION EFFICIENCIES;

CARBOXYLATION; CONVERSION EFFICIENCY; COPOLYMERS; HETEROJUNCTIONS; OPEN CIRCUIT VOLTAGE; PHOTOVOLTAIC EFFECTS; QUANTUM CHEMISTRY; SOLAR CELLS; THIOPHENE;

CONJUGATED POLYMERS;

EID: 84861460372     PISSN: 01700839     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00289-011-0662-1     Document Type: Article

References (30)

1. Dennler G, Scharber MC, Brabec CJ (2009) Polymer-fullerene bulk-heterojunction solar cells. Adv Mater 21:1323-1338. doi:10.1002/adma. 200801283
2. Gunes S, Neugebauer H, Sariciftci NS (2007) Conjugated polymer-based organic solar cells. Chem Rev 107:1324-1338. doi:10.1021/cr050149z (Pubitemid 46736541)
3. Zhan XW, Tan ZA, Domercq B, An ZS, Zhang X, Barlow S, Li YF, Zhu DB, Kippelen B, Marder SR (2007) A high-mobility electron-transport polymer with broad absorption and its use in field-effect transistors and all-polymer solar cells. J Am Chem Soc 129:7246-7247. doi:10.1021/ja071760d (Pubitemid 46980790)
4. Wang F, Luo J, Yang KX, Chen JW, Huang F, Cao Y (2005) Conjugated fluorene and silole copolymers: synthesis, characterization, electronic transition, light emission, photovoltaic cell, and field effect hole mobility. Macromolecules 38:2253-2260. doi:10.1021/ma047561l (Pubitemid 40430394)
5. Yue W, Zhao Y, Shao SY, Tian HK, Xie ZY, Geng YH, Wang FS (2009) Novel NIR-absorbing conjugated polymers for efficient polymer solar cells: effect of alkyl chain length on device performance. J Mater Chem 19:2199-2206. doi:10.1039/b818885h
6. Helgesen M, Søndergaard R, Krebs FC (2010) Advanced materials and processes for polymer solar cell devices. J Mater Chem 20:36-60. doi:10.1039/b913168j
7. Cheng YJ, Yang SH, Hsu CS (2009) Synthesis of conjugated polymers for organic solar cell applications. Chem Rev 109:5868-5923. doi:10.1021/cr900182s
8. Zhou HX, Yang LQ, Stuart AC, Price SC, Liu SB, You W (2011) Development of fluorinated benzothiadiazole as a structural unit for a polymer solar cell of 7% efficiency. Angew Chem Int Ed 50:2995-2998. doi:10.1002/ange.201005451
9. Price SC, Stuart AC, Yang LQ, Zhou HX, You W (2011) Fluorine substituted conjugated polymer of medium band gap yields 7% efficiency in polymer-fullerene solar cells. J Am Chem Soc 133:4625-4627. doi:10.1021/ja1112595
10. Chen HY, Hou JH, Zhang SQ, Liang YY, Yang GW, Yang Y, Yu LP, Wu Y, Li G (2009) Polymer solar cells with enhanced open-circuit voltage and efficiency. Nat Photon 3:649-653. doi: 10.1038/NPHOTON.2009.192
11. Huo LJ, Hou JH, Chen HY, Zhang SQ, Jiang Y, Chen TL, Yang Y (2009) Bandgap and molecular level control of the low-bandgap polymers based on 3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4- c]pyrrole-1,4-dione toward highly efficient polymer solar cells. Macromolecules 42:6564-6571. doi: 10.1021/ma9012972
12. Liang YY, Wu Y, Feng DQ, Tsai ST, Son HJ, Li G, Yu LP (2009) Development of new semiconducting polymers for high performance solar cells. J Am Chem Soc 131:56-57. doi: 10.1021/ja808373p
13. Thompson BC, Frechet JMJ (2007) Polymer-fullerene composite solar cells. Angew Chem Int Ed 47:58-77. doi:10.1002/anie.200702506
14. Hou JH, Chen HY, Zhang SQ, Chen RI, Yang Y, Wu Y, Li G (2009) Synthesis of a low band gap polymer and its application in highly efficient polymer solar cells. J Am Chem Soc 131: 15586-15587. doi:10.1021/ja9064975
15. Sirringhaus H, Wilson RJ, Friend RH, Inbasekaran M, Wu W, Woo EP, Grell M, Bradley DDC (2000) Mobility enhancement in conjugated polymer field-effect transistors through chain alignment in a liquid-crystalline phase. Appl Phys Lett 77:406-409. doi:10.1063/1.126991
16. Hou JH, Park MH, Zhang SQ, Yao Y, Chen LM, Li JH, Yang Y (2008) Bandgap and molecular energy level control of conjugated polymer photovoltaic materials based on benzo[1,2-b:4,5- b0]dithiophene. Macromolecules 41:6012-6018. doi:10.1021/ma800820r
17. Chen J, Shi MM, Hu XL, Wang M, Chen HZ (2010) Conjugated polymers based on benzodithiophene and arylene imides: extended absorptions and tunable electrochemical properties. Polymer 51:2897-2902. doi:10.1016/j.polymer.2010.04. 035
18. Chen ZH, Zheng Y, Yan H, Facchetti A (2008) Naphthalenedicarboximide- vs perylenedicarboximide- based copolymers. Synthesis and semiconducting properties in bottom-gate n-channel organic transistors. J Am Chem Soc 131:8-9. doi:10.1021/ja805407g
19. Brocks G, Tol A (1996) Small band gap semiconducting polymers made from dye molecules: polysquaraines. J Phys Chem 100:1838-1846. doi:10.1021/jp952276c (Pubitemid 126790005)
20. Gevorgyan SA, Krebs FC (2008) Bulk heterojunctions based on native polythiophene. Chem Mater 20:4386-4390. doi:10.1021/cm800431s
21. Hu XL, Shi MM, Chen J, Zuo LJ, Fu L, Liu YJ, Chen HZ (2010) Synthesis and photovoltaic properties of ester group functionalized polythiophene derivatives. Macromol Rapid Commun 32:506-511. doi:10.1002/marc.201000711
22. Ogawa K, Rasmussen SC (2003) A simple and efficient route to n-functionalized dithieno[3,2-b:20, 30-d]pyrroles: fused-ring building blocks for new conjugated polymeric systems. J Org Chem 68:2921-2928. doi:10.1021/jo034078k (Pubitemid 36512670)
23. Liu JY, Zhang R, Sauve G, Kowalewski T, McCullough RD (2008) Highly disordered polymer field effect transistors: n-alkyl dithieno[3,2-b:20,30-d] pyrrole-based copolymers with surprisingly high charge carrier mobilities. J Am Chem Soc 130:13167-13176. doi:10.1021/ja803077v
24. Bijleveld JC, Gevaerts VS, Di Nuzzo D, Turbiez M, Mathijssen SGJ, de Leeuw DM, Wienk MM, Janssen RAJ (2010) Efficient solar cells based on an easily accessible diketopyrrolopyrrole polymer. Adv Mater 22:242-246. doi:10.1002/adma.201001449
25. Shi MM, Deng D, Chen L, Ling J, Fu L, Hu XL, Chen HZ (2011) Design and synthesis of dithieno[ 3,2-b:2030-d]pyrrole-based conjugated polymers for photovoltaic applications: consensus between low band gap and low HOMO energy level. J Polym Sci A 49:1453-1461. doi:10.1002/pola.24567
26. Hu XL, Shi MM, Zuo LJ, Nan YX, Fu L, Chen HZ (2011) Synthesis, characterization, and photovoltaic property of a low band gap polymer alternating dithienopyrrole and thienopyrroledione units. Polymer 52:2559-2564. doi:10.1016/j.polymer.2011.03.057
27. Zhang GB, Fu YY, Zhang Q, Xie ZY (2010) Benzo[1,2-b:4,5-b0]dithiophene- dioxopyrrolothiophen copolymers for high performance solar cells. Chem Commun 46:4997-4999. doi:10.1039/c0cc00098a
28. Yuan MC, Chou YJ, Chen CM, Hsu CL, Wei KH (2011) A crystalline low-bandgap polymer comprising dithienosilole and thieno[3,4-c]pyrrole-4,6-dione units for bulk heterojunction solar cells. Polymer 52:2792-2798. doi:10.1016/j.polymer.2011.04.057
29. Hong YR, Wong HK, Moh LCH, Tan HS, Chen ZK (2011) Polymer solar cells based on copolymers of dithieno[3,2-b:20,30-d]silole and thienopyrroledione. Chem Commun 47:4920-4922. doi: 10.1039/c1cc10928f
30. Zhang X, Steckler TT, Dasari RR, Ohira S, Potscavage WJ, Tiwari SP, Coppee S, Ellinger S, Barlow S, Bredas JL, Kippelen B, Reynolds JR, Marder SR (2009) Dithienopyrrole-based donor-acceptor copolymers: low band-gap materials for charge transport, photovoltaics and electrochromism. J Mater Chem 20:123-134. doi:10.1039/b915940a