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2021 | OriginalPaper | Buchkapitel

15. π-Conjugated Polymers Incorporating Naphthalene-Based Nitrogen-Containing Heteroaromatics for Organic Photovoltaics

verfasst von : Itaru Osaka

Erschienen in: Progress in the Science of Functional Dyes

Verlag: Springer Singapore

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Abstract

Recently, a wide variety of π-conjugated polymers have been developed for the use as the active layer in organic photovoltaics (OPVs). This chapter will summarize the recent development of π-conjugated polymers with donor–acceptor motifs, specifically, based on naphthalene-based nitrogen-containing heteroaromatics as the acceptor unit. With the strong electron-deficient nature as well as the large π-conjugation system, incorporation of these heteroaromatics in the backbone allows us to create π-conjugated polymers having wide absorption range, i.e., narrow bandgap, deep HOMO energy levels, and high crystallinity, all of which are important for improving the efficiency of OPV cells. We describe the syntheses, properties, structural order in the thin films, and OPV performances of the π-conjugated polymers based on naphthobisthiadiazole and its analogues.

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Literatur
Zurück zum Zitat Adachi C, Hattori R, Kaji H, Tsujimura T (2019) Handbook of organic light-emitting diodes. Springer Adachi C, Hattori R, Kaji H, Tsujimura T (2019) Handbook of organic light-emitting diodes. Springer
Zurück zum Zitat Bao Z, Locklin J (2007) Organic field-effect transistors. CRC Press Bao Z, Locklin J (2007) Organic field-effect transistors. CRC Press
Zurück zum Zitat Biniek L, Schroeder BC, Nielsen CB, McCulloch I (2012) Recent advances in high mobility donor-acceptor semiconducting polymers. J Mater Chem 22:14803–14813CrossRef Biniek L, Schroeder BC, Nielsen CB, McCulloch I (2012) Recent advances in high mobility donor-acceptor semiconducting polymers. J Mater Chem 22:14803–14813CrossRef
Zurück zum Zitat Boudreault P-LT, Najari A, Leclerc M (2011) Processable low-bandgap polymers for photovoltaic applications. Chem Mater 23:456–469CrossRef Boudreault P-LT, Najari A, Leclerc M (2011) Processable low-bandgap polymers for photovoltaic applications. Chem Mater 23:456–469CrossRef
Zurück zum Zitat Brabec C, Scherf U, Dyakonov V (2014) Organic photovoltaics. Wiley-VCH Brabec C, Scherf U, Dyakonov V (2014) Organic photovoltaics. Wiley-VCH
Zurück zum Zitat Dong Y, Hu X, Duan C, Liu P, Liu S, Lan L, Chen D, Ying L, Su S, Gong X, Huang F, Cao Y (2013) A series of new medium-bandgap conjugated polymers based on naphtho[1,2-c:5,6-c]bis(2-octyl-[1,2,3]triazole) for high-performance polymer solar cells. Adv Mater 25:3683–3688CrossRef Dong Y, Hu X, Duan C, Liu P, Liu S, Lan L, Chen D, Ying L, Su S, Gong X, Huang F, Cao Y (2013) A series of new medium-bandgap conjugated polymers based on naphtho[1,2-c:5,6-c]bis(2-octyl-[1,2,3]triazole) for high-performance polymer solar cells. Adv Mater 25:3683–3688CrossRef
Zurück zum Zitat Green MA, Ho-Baillie A, Snaith HJ (2014) The emergence of perovskite solar cells. Nat Photon 8:506–514CrossRef Green MA, Ho-Baillie A, Snaith HJ (2014) The emergence of perovskite solar cells. Nat Photon 8:506–514CrossRef
Zurück zum Zitat Imai K, Kurihara M, Mathias L, Wittmann J, Alston WB, Stille JK (1973) Synthesis and properties of thermally stable ladder polymers containing the 1,4-pyrazine ring obtained from polyheterocyclizations of tetramines and tetraketones in poly(phosphoric acid) and m-cresol. Macromolecules 6:158–162CrossRef Imai K, Kurihara M, Mathias L, Wittmann J, Alston WB, Stille JK (1973) Synthesis and properties of thermally stable ladder polymers containing the 1,4-pyrazine ring obtained from polyheterocyclizations of tetramines and tetraketones in poly(phosphoric acid) and m-cresol. Macromolecules 6:158–162CrossRef
Zurück zum Zitat Kawashima K, Miyazaki E, Shimawaki M, Inoue Y, Mori H, Takemura N, Osaka I, Takimiya K (2013) 5,10-diborylated naphtho[1,2-c:5,6-c′]bis[1,2,5]thiadiazole: a ready-to-use precursor for the synthesis of high-performance semiconducting polymers. Polym Chem 4:5224–5227CrossRef Kawashima K, Miyazaki E, Shimawaki M, Inoue Y, Mori H, Takemura N, Osaka I, Takimiya K (2013) 5,10-diborylated naphtho[1,2-c:5,6-c′]bis[1,2,5]thiadiazole: a ready-to-use precursor for the synthesis of high-performance semiconducting polymers. Polym Chem 4:5224–5227CrossRef
Zurück zum Zitat Kawashima K, Osaka I, Takimiya K (2015a) Effect of chalcogen atom on the properties of naphthobischalcogenadiazole-based π-conjugated polymers. Chem Mater 27:6558–6570CrossRef Kawashima K, Osaka I, Takimiya K (2015a) Effect of chalcogen atom on the properties of naphthobischalcogenadiazole-based π-conjugated polymers. Chem Mater 27:6558–6570CrossRef
Zurück zum Zitat Kawashima K, Tamai Y, Ohkita H, Osaka I, Takimiya K (2015b) High-efficiency polymer solar cells with small photon energy loss. Nat Commun 6:10085CrossRef Kawashima K, Tamai Y, Ohkita H, Osaka I, Takimiya K (2015b) High-efficiency polymer solar cells with small photon energy loss. Nat Commun 6:10085CrossRef
Zurück zum Zitat Kawashima K, Fukuhara T, Suda Y, Suzuki Y, Koganezawa T, Yoshida H, Ohkita H, Osaka I, Takimiya K (2016) Implication of fluorine atom on electronic properties, ordering structures, and photovoltaic performance in naphthobisthiadiazole-based semiconducting polymers. J Am Chem Soc 138:10265–10275CrossRef Kawashima K, Fukuhara T, Suda Y, Suzuki Y, Koganezawa T, Yoshida H, Ohkita H, Osaka I, Takimiya K (2016) Implication of fluorine atom on electronic properties, ordering structures, and photovoltaic performance in naphthobisthiadiazole-based semiconducting polymers. J Am Chem Soc 138:10265–10275CrossRef
Zurück zum Zitat King RR, Bhusari D, Boca A, Larrabee D, Liu XQ, Hong W, Fetzer CM, Law DC, Karam NH (2011) Band gap-voltage offset and energy production in next-generation multijunction solar cells. Prog Photovolt 19:797–812CrossRef King RR, Bhusari D, Boca A, Larrabee D, Liu XQ, Hong W, Fetzer CM, Law DC, Karam NH (2011) Band gap-voltage offset and energy production in next-generation multijunction solar cells. Prog Photovolt 19:797–812CrossRef
Zurück zum Zitat Li W, Hendriks KH, Furlan A, Wienk MM, Janssen RAJ (2015) High quantum efficiencies in polymer solar cells at energy losses below 0.6 eV. J Am Chem Soc 137:2231–2234CrossRef Li W, Hendriks KH, Furlan A, Wienk MM, Janssen RAJ (2015) High quantum efficiencies in polymer solar cells at energy losses below 0.6 eV. J Am Chem Soc 137:2231–2234CrossRef
Zurück zum Zitat Mataka S, Takahashi K, Ikezaki Y, Hatta T, Tori-i A, Tashiro M (1991) Sulfur nitride in organic chemsitry. XIV, Selective formation of benzo-and benzobis [1, 2, 5] thiadiazole skeleton in the reaction of tetrasulfur tetranitride with naphthalenols and related compounds. Bull Chem Soc Jpn 64:68–73CrossRef Mataka S, Takahashi K, Ikezaki Y, Hatta T, Tori-i A, Tashiro M (1991) Sulfur nitride in organic chemsitry. XIV, Selective formation of benzo-and benzobis [1, 2, 5] thiadiazole skeleton in the reaction of tetrasulfur tetranitride with naphthalenols and related compounds. Bull Chem Soc Jpn 64:68–73CrossRef
Zurück zum Zitat McCullough RD (1998) The chemistry of conducting polythiophenes. Adv Mater 10:93–116CrossRef McCullough RD (1998) The chemistry of conducting polythiophenes. Adv Mater 10:93–116CrossRef
Zurück zum Zitat Mikie T, Osaka I (2018) Selective synthesis and properties of electron-deficient hybrid naphthalene-based π-conjugated systems. Chem Eur J 24:19228–19235CrossRef Mikie T, Osaka I (2018) Selective synthesis and properties of electron-deficient hybrid naphthalene-based π-conjugated systems. Chem Eur J 24:19228–19235CrossRef
Zurück zum Zitat Mikie T, Osaka I (2019) Ester-Functionalized naphthobispyrazine as an acceptor building unit for semiconducting polymers: synthesis, properties, and photovoltaic performance. Macromolecules 52:3909–3917CrossRef Mikie T, Osaka I (2019) Ester-Functionalized naphthobispyrazine as an acceptor building unit for semiconducting polymers: synthesis, properties, and photovoltaic performance. Macromolecules 52:3909–3917CrossRef
Zurück zum Zitat Mikie T, Kawashima K, Komeyama K, Yoshida H, Osaka I (2017) Naphthobispyrazine as an electron-deficient building unit for π-conjugated polymers: efficient synthesis and polymer properties. Chem Lett 46:1193–1196CrossRef Mikie T, Kawashima K, Komeyama K, Yoshida H, Osaka I (2017) Naphthobispyrazine as an electron-deficient building unit for π-conjugated polymers: efficient synthesis and polymer properties. Chem Lett 46:1193–1196CrossRef
Zurück zum Zitat Osaka I, Takimiya K (2017) Naphthobischalcogenadiazole conjugated polymers: emerging materials for organic electronics. Adv Mater 39:1605218CrossRef Osaka I, Takimiya K (2017) Naphthobischalcogenadiazole conjugated polymers: emerging materials for organic electronics. Adv Mater 39:1605218CrossRef
Zurück zum Zitat Osaka I, Shimawaki M, Mori H, Doi I, Miyazaki E, Koganezawa T, Takimiya K (2012) Synthesis, characterization, and transistor and solar cell applications of a naphthobisthiadiazole-based semiconducting polymer. J Am Chem Soc 134:3498–3507CrossRef Osaka I, Shimawaki M, Mori H, Doi I, Miyazaki E, Koganezawa T, Takimiya K (2012) Synthesis, characterization, and transistor and solar cell applications of a naphthobisthiadiazole-based semiconducting polymer. J Am Chem Soc 134:3498–3507CrossRef
Zurück zum Zitat Osaka I, Saito M, Koganezawa T, Takimiya K (2014) Thiophene-thiazolothiazole copolymers: significant impact of side chain composition on backbone orientation and solar cell performances. Adv Mater 26:331–338CrossRef Osaka I, Saito M, Koganezawa T, Takimiya K (2014) Thiophene-thiazolothiazole copolymers: significant impact of side chain composition on backbone orientation and solar cell performances. Adv Mater 26:331–338CrossRef
Zurück zum Zitat Peet J, Wen L, Byrne P, Rodman S, Forberich K, Shao Y, Drolet N, Gaudiana R, Dennler G, Waller D (2011) Bulk heterojunction solar cells with thick active layers and high fill factors enabled by a bithiophene-co-thiazolothiazole push-pull copolymer. Appl Phys Lett 98:043301CrossRef Peet J, Wen L, Byrne P, Rodman S, Forberich K, Shao Y, Drolet N, Gaudiana R, Dennler G, Waller D (2011) Bulk heterojunction solar cells with thick active layers and high fill factors enabled by a bithiophene-co-thiazolothiazole push-pull copolymer. Appl Phys Lett 98:043301CrossRef
Zurück zum Zitat Reynolds JR, Thompson BC, Skotheim TA (2019) Handbook of conducting polymers, 4th ed. CRC Press Reynolds JR, Thompson BC, Skotheim TA (2019) Handbook of conducting polymers, 4th ed. CRC Press
Zurück zum Zitat Saito M, Koganezawa T, Osaka I (2018) Correlation between distribution of polymer orientation and cell structure in organic photovoltaics. ACS Appl Mater Interfaces 10:32420–32425CrossRef Saito M, Koganezawa T, Osaka I (2018) Correlation between distribution of polymer orientation and cell structure in organic photovoltaics. ACS Appl Mater Interfaces 10:32420–32425CrossRef
Zurück zum Zitat Thompson BC, Fréchet JMJ (2008) Polymer-fullerene composite solar cells. Angew Chem Int Ed 47:58–77CrossRef Thompson BC, Fréchet JMJ (2008) Polymer-fullerene composite solar cells. Angew Chem Int Ed 47:58–77CrossRef
Zurück zum Zitat Villena-Blanco M, Jolly WL (1967) Tetrasulfur tetranitride, S4N4. Inorganic syntheses, vol 9. Wiley, 98–102 Villena-Blanco M, Jolly WL (1967) Tetrasulfur tetranitride, S4N4. Inorganic syntheses, vol 9. Wiley, 98–102
Zurück zum Zitat Vohra V, Kawashima K, Kakara T, Koganezawa T, Osaka I, Takimiya K, Murata H (2015) Efficient inverted polymer solar cells employing favourable molecular orientation. Nat Photon 9:403–408CrossRef Vohra V, Kawashima K, Kakara T, Koganezawa T, Osaka I, Takimiya K, Murata H (2015) Efficient inverted polymer solar cells employing favourable molecular orientation. Nat Photon 9:403–408CrossRef
Zurück zum Zitat Wang M, Hu X, Liu P, Li W, Gong X, Huang F, Cao Y (2011) Donor-acceptor conjugated polymer based on naphtho[1,2-c:5,6-c]bis[1,2,5]thiadiazole for high-performance polymer solar cells. J Am Chem Soc 133:9638–9641CrossRef Wang M, Hu X, Liu P, Li W, Gong X, Huang F, Cao Y (2011) Donor-acceptor conjugated polymer based on naphtho[1,2-c:5,6-c]bis[1,2,5]thiadiazole for high-performance polymer solar cells. J Am Chem Soc 133:9638–9641CrossRef
Zurück zum Zitat Wang M, Wang H, Yokoyama T, Liu X, Huang Y, Zhang Y, Nguyen TQ, Aramaki S, Bazan GC (2014) High open circuit voltage in regioregular narrow band gap polymer solar cells. J Am Chem Soc 136:12576–12579CrossRef Wang M, Wang H, Yokoyama T, Liu X, Huang Y, Zhang Y, Nguyen TQ, Aramaki S, Bazan GC (2014) High open circuit voltage in regioregular narrow band gap polymer solar cells. J Am Chem Soc 136:12576–12579CrossRef
Zurück zum Zitat Yang T, Wang M, Duan C, Hu X, Huang L, Peng J, Huang F, Gong X (2012) Inverted polymer solar cells with 8.4% efficiency by conjugated polyelectrolyte. Energy Environ Sci 5:8208–8214CrossRef Yang T, Wang M, Duan C, Hu X, Huang L, Peng J, Huang F, Gong X (2012) Inverted polymer solar cells with 8.4% efficiency by conjugated polyelectrolyte. Energy Environ Sci 5:8208–8214CrossRef
Zurück zum Zitat Yu T, Xu X, Zhang G, Wan J, Li Y, Peng Q (2017) Wide bandgap copolymers based on quinoxalino[6,5-f]quinoxaline for highly efficient nonfullerene polymer solar cells. Adv Funct Mater 27:1701491CrossRef Yu T, Xu X, Zhang G, Wan J, Li Y, Peng Q (2017) Wide bandgap copolymers based on quinoxalino[6,5-f]quinoxaline for highly efficient nonfullerene polymer solar cells. Adv Funct Mater 27:1701491CrossRef
Zurück zum Zitat Zhang Z, Lin F, Chen HC, Wu HC, Chung CL, Lu C, Liu SH, Tung SH, Chen WC, Wong KT, Chou PT (2015) A silole copolymer containing a ladder-type heptacylic arene and naphthobisoxadiazole moieties for highly efficient polymer solar cells. Energy Environ Sci 8:552–557CrossRef Zhang Z, Lin F, Chen HC, Wu HC, Chung CL, Lu C, Liu SH, Tung SH, Chen WC, Wong KT, Chou PT (2015) A silole copolymer containing a ladder-type heptacylic arene and naphthobisoxadiazole moieties for highly efficient polymer solar cells. Energy Environ Sci 8:552–557CrossRef
Metadaten
Titel
π-Conjugated Polymers Incorporating Naphthalene-Based Nitrogen-Containing Heteroaromatics for Organic Photovoltaics
verfasst von
Itaru Osaka
Copyright-Jahr
2021
Verlag
Springer Singapore
DOI
https://doi.org/10.1007/978-981-33-4392-4_15