Skip to main content
Erschienen in: Journal of Materials Science 16/2015

01.08.2015 | Original Paper

Fine tuning of terpolymer properties by incorporating electron-accepting difluorobenzene and diketopyrrolopyrrole units

verfasst von: Zhanfeng Li, Zhihui Wang, Weipeng Liu, Yanxia Cui, Hua Wang, Fang Shi, Yuying Hao

Erschienen in: Journal of Materials Science | Ausgabe 16/2015

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

Abstract

A series of low band gap terpolymers (PBDT–DFBx–DPPy) incorporating various ratios of two acceptor units, difluorobenzene (DFB) and diketopyrrolo[3,4-c]pyrrole (DPP), were synthesized by Pd-catalyzed Stille polymerization. The effects of the DFB and DPP units on UV–Vis absorption, highest occupied molecular orbital (HOMO) energy levels, and terpolymer: PC60BM solar cell performance, especially the short-circuit current (J sc), were investigated. The polymer films exhibited broad and intense absorption spectra, covering the spectral range from 300 nm up to 900 nm. The optical properties of these random terpolymers can be easily controlled by tuning the ratio between DFB and DPP; an increase in DFB induced increased absorption between 300 and 550 nm and a lower HOMO energy level. The terpolymer PBDT–DFB50–DPP50 with the percentage of DFB up to 50 % in the bulk heterojunction polymer solar cell showed a high open-circuit voltage of 0.74 V and a J sc of 7.83 mA cm−2. This study demonstrated that significant changes in polymer electronic properties can be tuned by the strategic combination of simple electron-deficient monomers and their composition in the random terpolymers.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Literatur
1.
Zurück zum Zitat Nelson J (2011) Polymer: fullerene bulk heterojunction solar cells. Mater Today 14:462–470CrossRef Nelson J (2011) Polymer: fullerene bulk heterojunction solar cells. Mater Today 14:462–470CrossRef
2.
Zurück zum Zitat Dou LT, You JB, Hong ZR, Xu Z, Li G, Street RA, yang Y (2013) 25th anniversary article: a decade of organic/polymeric photovoltaic research. Adv Mater 25:6642–6671CrossRef Dou LT, You JB, Hong ZR, Xu Z, Li G, Street RA, yang Y (2013) 25th anniversary article: a decade of organic/polymeric photovoltaic research. Adv Mater 25:6642–6671CrossRef
3.
Zurück zum Zitat Li G, Zhu R, Yang Y (2012) Polymer solar cells. Nat Photonics 6:153–161CrossRef Li G, Zhu R, Yang Y (2012) Polymer solar cells. Nat Photonics 6:153–161CrossRef
4.
Zurück zum Zitat Cao JM, Liao QG, Du XY, Chen JH, Xia Z, Zuo QQ, Ding LM (2013) A pentacyclic a romatic lactam building block for efficient polymer solar cells. Energy Environ Sci 6:3224–3228CrossRef Cao JM, Liao QG, Du XY, Chen JH, Xia Z, Zuo QQ, Ding LM (2013) A pentacyclic a romatic lactam building block for efficient polymer solar cells. Energy Environ Sci 6:3224–3228CrossRef
5.
Zurück zum Zitat You JB, Dou LT, Yoshimura K, Kato T, Ohya K, Moriarty T, Emery K, Chen CC, Gao J, Li G, Yang Y (2013) A polymer tandem solar cell with 10.6 % power conversion efficiency. Nat Commun 4:1446–1455CrossRef You JB, Dou LT, Yoshimura K, Kato T, Ohya K, Moriarty T, Emery K, Chen CC, Gao J, Li G, Yang Y (2013) A polymer tandem solar cell with 10.6 % power conversion efficiency. Nat Commun 4:1446–1455CrossRef
6.
Zurück zum Zitat He ZC, Zhong CM, Su SJ, Xu M, Wu HB, Cao Y (2012) Enhanced power-conversion efficiency in polymer solar cells using an inverted device structure. Nat Photonics 6:591–595 He ZC, Zhong CM, Su SJ, Xu M, Wu HB, Cao Y (2012) Enhanced power-conversion efficiency in polymer solar cells using an inverted device structure. Nat Photonics 6:591–595
7.
Zurück zum Zitat Dou L, You J, Yang J, Chen CC, He Y, Murase S, Moriarty T, Emery K, Li G, Yang Y (2012) Tandem polymer solar cells featuring a spectrally matched low-band gap polymer. Nat Photonics 6:180–185CrossRef Dou L, You J, Yang J, Chen CC, He Y, Murase S, Moriarty T, Emery K, Li G, Yang Y (2012) Tandem polymer solar cells featuring a spectrally matched low-band gap polymer. Nat Photonics 6:180–185CrossRef
8.
Zurück zum Zitat Zhang SQ, Ye L, Wang Q, Li ZJ, Guo X, Huo LJ, Fan HL, Hou JH (2013) Enhanced photovoltaic performance of diketopyrrolopyrrole (DPP)-based polymers with extended π conjugation. J Phys Chem C 117:9550–9557CrossRef Zhang SQ, Ye L, Wang Q, Li ZJ, Guo X, Huo LJ, Fan HL, Hou JH (2013) Enhanced photovoltaic performance of diketopyrrolopyrrole (DPP)-based polymers with extended π conjugation. J Phys Chem C 117:9550–9557CrossRef
9.
Zurück zum Zitat Sun S, Zhang P, Li JF, Li YK, Wang JL, Zhang SJ, Xia YJ, Meng XJ, Fan DW, Chu JH (2014) Synthetically controlling the optoelectronic properties of dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene-alt-diketopyrrolopyrrole-conjugated polymers for efficient solar cells. J Mater Chem A 2:15316–15325CrossRef Sun S, Zhang P, Li JF, Li YK, Wang JL, Zhang SJ, Xia YJ, Meng XJ, Fan DW, Chu JH (2014) Synthetically controlling the optoelectronic properties of dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene-alt-diketopyrrolopyrrole-conjugated polymers for efficient solar cells. J Mater Chem A 2:15316–15325CrossRef
10.
Zurück zum Zitat Kang TE, Kim KH, Kim BJ (2014) Design of terpolymers as electron donors for highly efficient polymer solar cells. J Mater Chem A 2:15252–15267CrossRef Kang TE, Kim KH, Kim BJ (2014) Design of terpolymers as electron donors for highly efficient polymer solar cells. J Mater Chem A 2:15252–15267CrossRef
11.
Zurück zum Zitat Chao YH, Jheng JF, Wu JS, Wu KY, Peng HH, Tsai MC, Wang CL, Hsiao YN, Wang CL, Lin CY, Hsu CS (2014) Porphyrin-incorporated 2D D-A polymers with over 8.5 % polymer solar cell efficiency. Adv Mater 26:5205–5210CrossRef Chao YH, Jheng JF, Wu JS, Wu KY, Peng HH, Tsai MC, Wang CL, Hsiao YN, Wang CL, Lin CY, Hsu CS (2014) Porphyrin-incorporated 2D D-A polymers with over 8.5 % polymer solar cell efficiency. Adv Mater 26:5205–5210CrossRef
12.
Zurück zum Zitat Wang H, Yu X, Yi C, Ren H, Liu C, Yang Y, Xiao S, Zheng J, Karim A, Cheng SZD, Gong X (2013) Fine-tuning of fluorinated thieno[3,4-b]thiophene copolymer for efficient polymer solar cells. J Phys Chem C 117:4358–4363CrossRef Wang H, Yu X, Yi C, Ren H, Liu C, Yang Y, Xiao S, Zheng J, Karim A, Cheng SZD, Gong X (2013) Fine-tuning of fluorinated thieno[3,4-b]thiophene copolymer for efficient polymer solar cells. J Phys Chem C 117:4358–4363CrossRef
13.
Zurück zum Zitat Jung JW, Liu F, Russell TP, Jo WH (2013) Semi-crystalline random conjugated copolymers with panchromatic absorption for highly efficient polymer solar cells. Energy Environ Sci 6:3301–3307CrossRef Jung JW, Liu F, Russell TP, Jo WH (2013) Semi-crystalline random conjugated copolymers with panchromatic absorption for highly efficient polymer solar cells. Energy Environ Sci 6:3301–3307CrossRef
14.
Zurück zum Zitat Kang TE, Cho HH, Kim H, Lee W, Kang H, Kim BJ (2013) Importance of optimal composition in random terpolymer-based polymer solar cells. Macromolecules 46:6806–6813CrossRef Kang TE, Cho HH, Kim H, Lee W, Kang H, Kim BJ (2013) Importance of optimal composition in random terpolymer-based polymer solar cells. Macromolecules 46:6806–6813CrossRef
15.
Zurück zum Zitat Deng Z, Chen L, Wu F, Chen Y (2014) Novel donor-acceptor random copolymers containing phenanthrocarbazole and diketopyrrolopyrrole for organic photovoltaics and the significant molecular geometry effect on their performance. J Phys Chem C 118:6038–6045CrossRef Deng Z, Chen L, Wu F, Chen Y (2014) Novel donor-acceptor random copolymers containing phenanthrocarbazole and diketopyrrolopyrrole for organic photovoltaics and the significant molecular geometry effect on their performance. J Phys Chem C 118:6038–6045CrossRef
16.
Zurück zum Zitat Zhou J, Xie S, Amond EF, Becker ML (2013) Tuning energy levels of low band gap semi-random two acceptor copolymers. Macromolecules 46:3391–3394CrossRef Zhou J, Xie S, Amond EF, Becker ML (2013) Tuning energy levels of low band gap semi-random two acceptor copolymers. Macromolecules 46:3391–3394CrossRef
17.
Zurück zum Zitat Hendriks KH, Heintges GH, Gevaerts VS, Wienk MM, Janssen RA (2013) High-molecular-weight regular alternating diketopyrrolopyrrole-based terpolymers for efficient organic solar cells. Angew Chem Int Ed 52:8341–8344CrossRef Hendriks KH, Heintges GH, Gevaerts VS, Wienk MM, Janssen RA (2013) High-molecular-weight regular alternating diketopyrrolopyrrole-based terpolymers for efficient organic solar cells. Angew Chem Int Ed 52:8341–8344CrossRef
18.
Zurück zum Zitat Li W, Furlan A, Christian Roelofs WS, Hendriks KH, Pruissen GWP, Wienk MM, Janssen RAJ (2014) Wide band gap diketopyrrolopyrrole-based conjugated polymers incorporating biphenyl units applied in polymer solar cells. Chem Commun 50:679–681CrossRef Li W, Furlan A, Christian Roelofs WS, Hendriks KH, Pruissen GWP, Wienk MM, Janssen RAJ (2014) Wide band gap diketopyrrolopyrrole-based conjugated polymers incorporating biphenyl units applied in polymer solar cells. Chem Commun 50:679–681CrossRef
19.
Zurück zum Zitat Zhou HX, Yang LQ, Stuart AC, Price SC, Liu S, You W (2011) Development of fluorinated benzothiadiazole as a structural unit for a polymer solar cell of 7 % efficiency. Angew Chem 123:3051–3054CrossRef Zhou HX, Yang LQ, Stuart AC, Price SC, Liu S, You W (2011) Development of fluorinated benzothiadiazole as a structural unit for a polymer solar cell of 7 % efficiency. Angew Chem 123:3051–3054CrossRef
20.
Zurück zum Zitat Park JH, Jung EH, Jung JW, Jo WH (2013) A fluorinated phenylene unit as a building block for high-performance n-type semiconducting polymer. Adv Mater 25:2583–2588CrossRef Park JH, Jung EH, Jung JW, Jo WH (2013) A fluorinated phenylene unit as a building block for high-performance n-type semiconducting polymer. Adv Mater 25:2583–2588CrossRef
21.
Zurück zum Zitat Wang Z, Li Z, Zhang H, Liu W, Xu X, Si C, Cui Y, Sun Q, Wang H, Shi F, Hao YA (2014) Conjugated random copolymer of benzodithiophene–difluorobenzene–diketopyrrolopyrrole with full visible-light absorption for bulk-heterojunction solar cells. Macromol Chem Phys 215:2119–2124CrossRef Wang Z, Li Z, Zhang H, Liu W, Xu X, Si C, Cui Y, Sun Q, Wang H, Shi F, Hao YA (2014) Conjugated random copolymer of benzodithiophene–difluorobenzene–diketopyrrolopyrrole with full visible-light absorption for bulk-heterojunction solar cells. Macromol Chem Phys 215:2119–2124CrossRef
22.
Zurück zum Zitat Li Z, Qiao Z, Liu W, Wang Z, Wang H, Shi F, Hao Y (2015) Conjugated random copolymer of benzodithiophene–difluorobenzene–diketopyrrolopyrrole–benzothiadiazole with a broad absorption range of 300–900 nm for bulk heterojunction solar cells. Mater Lett 139:307–310CrossRef Li Z, Qiao Z, Liu W, Wang Z, Wang H, Shi F, Hao Y (2015) Conjugated random copolymer of benzodithiophene–difluorobenzene–diketopyrrolopyrrole–benzothiadiazole with a broad absorption range of 300–900 nm for bulk heterojunction solar cells. Mater Lett 139:307–310CrossRef
23.
Zurück zum Zitat Liu C, Wang K, Hu X, Yang Y, Hsu CH, Zhang W, Xiao S, Gong X, Cao Y (2013) Molecular weight effect on the efficiency of polymer solar cells. ACS Appl Mater Interfaces 5:12163–12167CrossRef Liu C, Wang K, Hu X, Yang Y, Hsu CH, Zhang W, Xiao S, Gong X, Cao Y (2013) Molecular weight effect on the efficiency of polymer solar cells. ACS Appl Mater Interfaces 5:12163–12167CrossRef
24.
Zurück zum Zitat Li WT, Yang LQ, Tumbleston JR, Yan L, Ade H, You W (2014) Controlling molecular weight of a high efficiency donor-acceptor conjugated polymer and understanding its significant impact on photovoltaic properties. Adv Mater 26:4456–4462CrossRef Li WT, Yang LQ, Tumbleston JR, Yan L, Ade H, You W (2014) Controlling molecular weight of a high efficiency donor-acceptor conjugated polymer and understanding its significant impact on photovoltaic properties. Adv Mater 26:4456–4462CrossRef
25.
Zurück zum Zitat Dou L, Gao J, Richard E, You J, Chen CC, Cha KC, He Y, Li G, Yang Y (2012) Systematic investigation of benzodithiophene- and diketopyrrolopyrrole-based low-bandgap polymers designed for single junction and tandem polymer solar cells. J Am Chem Soc 134:10071–10079CrossRef Dou L, Gao J, Richard E, You J, Chen CC, Cha KC, He Y, Li G, Yang Y (2012) Systematic investigation of benzodithiophene- and diketopyrrolopyrrole-based low-bandgap polymers designed for single junction and tandem polymer solar cells. J Am Chem Soc 134:10071–10079CrossRef
26.
Zurück zum Zitat Liang Y, Feng D, Wu Y, Tsai ST, Li G, Ray C, Yu LP (2009) Highly efficient solar cell polymers developed via fine-tuning of structural and electronic properties. J Am Chem Soc 131:7792–7799CrossRef Liang Y, Feng D, Wu Y, Tsai ST, Li G, Ray C, Yu LP (2009) Highly efficient solar cell polymers developed via fine-tuning of structural and electronic properties. J Am Chem Soc 131:7792–7799CrossRef
27.
Zurück zum Zitat Wang E, Hou L, Wang Z, Hellström S, Mammo W, Zhang F, Inganäs O, Andersson MR (2010) Small band gap polymers synthesized via a modified nitration of 4,7-dibromo-2,1,3-benzothiadiazole. Org Lett 12:4470–4473CrossRef Wang E, Hou L, Wang Z, Hellström S, Mammo W, Zhang F, Inganäs O, Andersson MR (2010) Small band gap polymers synthesized via a modified nitration of 4,7-dibromo-2,1,3-benzothiadiazole. Org Lett 12:4470–4473CrossRef
28.
Zurück zum Zitat Kang TE, Cho H, Cho C, Kim K, Kang H, Lee M, Lee S, Kim B, Im C, Kim BJ (2013) Photoinduced charge transfer in donor-acceptor (DA) copolymer: fullerene bis-adduct polymer solar cells. ACS Appl Mater Interfaces 5:861–868CrossRef Kang TE, Cho H, Cho C, Kim K, Kang H, Lee M, Lee S, Kim B, Im C, Kim BJ (2013) Photoinduced charge transfer in donor-acceptor (DA) copolymer: fullerene bis-adduct polymer solar cells. ACS Appl Mater Interfaces 5:861–868CrossRef
29.
Zurück zum Zitat Wu PT, Kim FS, Champion RD, Jenekhe SA (2008) Conjugated donor-acceptor copolymer semiconductors. Synthesis, optical properties, electrochemistry, and field-effect carrier mobility of pyridopyrazine-based copolymers. Macromolecules 41:7021–7028CrossRef Wu PT, Kim FS, Champion RD, Jenekhe SA (2008) Conjugated donor-acceptor copolymer semiconductors. Synthesis, optical properties, electrochemistry, and field-effect carrier mobility of pyridopyrazine-based copolymers. Macromolecules 41:7021–7028CrossRef
30.
Zurück zum Zitat Shen P, Bin H, Xiao L, Li Y (2013) Enhancing photovoltaic performance of copolymers containing thiophene unit with D−A conjugated side chain by rational molecular design. Macromolecules 46:9575–9586CrossRef Shen P, Bin H, Xiao L, Li Y (2013) Enhancing photovoltaic performance of copolymers containing thiophene unit with D−A conjugated side chain by rational molecular design. Macromolecules 46:9575–9586CrossRef
31.
Zurück zum Zitat Li W, Roelofs WSC, Wienk MM, Janssen RAJ (2012) Enhancing the photocurrent in diketopyrrolopyrrole-based polymer solar cells via energy level control. J Am Chem Soc 134:13787–13795CrossRef Li W, Roelofs WSC, Wienk MM, Janssen RAJ (2012) Enhancing the photocurrent in diketopyrrolopyrrole-based polymer solar cells via energy level control. J Am Chem Soc 134:13787–13795CrossRef
Metadaten
Titel
Fine tuning of terpolymer properties by incorporating electron-accepting difluorobenzene and diketopyrrolopyrrole units
verfasst von
Zhanfeng Li
Zhihui Wang
Weipeng Liu
Yanxia Cui
Hua Wang
Fang Shi
Yuying Hao
Publikationsdatum
01.08.2015
Verlag
Springer US
Erschienen in
Journal of Materials Science / Ausgabe 16/2015
Print ISSN: 0022-2461
Elektronische ISSN: 1573-4803
DOI
https://doi.org/10.1007/s10853-015-8924-1

Weitere Artikel der Ausgabe 16/2015

Journal of Materials Science 16/2015 Zur Ausgabe

    Marktübersichten

    Die im Laufe eines Jahres in der „adhäsion“ veröffentlichten Marktübersichten helfen Anwendern verschiedenster Branchen, sich einen gezielten Überblick über Lieferantenangebote zu verschaffen.