nach oben

Erschienen in:

2015 | OriginalPaper | Buchkapitel

5. All-Polymer Solar Cells Based on Organometallic Polymers

verfasst von : Tsuyoshi Michinobu

Erschienen in: Organometallics and Related Molecules for Energy Conversion

Verlag: Springer Berlin Heidelberg

Einloggen

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

search-config

KI-gestützte Suche

Aus

Abstract

Bulk-heterojunction (BHJ) solar cells using n-type semiconducting polymers, instead of the conventional fullerene derivatives, are known as all-polymer solar cells. Their significant advantages include designable structures of both p-type and n-type semiconducting polymers. In this chapter, recent advances in all-polymer solar cells are introduced. Particular attention is focused on the development of high-performance n-type semiconducting polymers. However, organometallic polymers have generally been employed as p-type semiconductors in BHJ solar cells. Therefore, there are a few examples of all-polymer solar cells based on organometallic polymers. In order to solve this problem, a novel method of inverting the semiconducting feature is applied to produce promising Pt-polyyne polymers with potentially n-type energy levels. The main chain alkynes of the precursor Pt-polyyne polymers are modified by the high-yielding transformation into tetracyanobutadiene units through a [2 + 2] cycloaddition-retroelectrocyclization with tetracyanoethylene (TCNE). All-polymer solar cells composed of the p-type poly(3-hexylthiophene) (P3HT) and n-type Pt-polyyne polymer are successfully fabricated, and the photocurrent generation is demonstrated.

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!

Jetzt informieren

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!

Jetzt informieren

Vorheriges Kapitel Ruthenium-Based Photosensitizers for Dye-Sensitized Solar Cells

Nächstes Kapitel Transition-Metal Complexes for Triplet–Triplet Annihilation-Based Energy Upconversion

Thompson BC, Fréchet JMJ (2008) Polymer-fullerene composite solar cells. Angew Chem Int Ed 47:58–77CrossRef

Dennler G, Scharber MC, Brabec CJ (2009) Polymer-fullerene bulk-heterojunction solar cells. Adv Mater 21:1323–1338CrossRef

Brabec CJ, Gowrisanker S, Malls JJM, Laird D, Jia S, Williams SP (2010) Polymer-fullerene bulk-heterojunction solar cells. Adv Mater 22:3839–3856CrossRef

Dang MT, Hirsch L, Wantz G (2011) P3HT:PCBM, best seller in polymer photovoltaic research. Adv Mater 23:3597–3602CrossRef

He Z, Zhong C, Su S, Xu M, Wu H, Cao Y (2012) Enhanced power-conversion efficiency in polymer solar cells using an inverted device structure. Nat Photon 6:591–595

You J, Dou L, 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 4:1446CrossRef

Zhang Y, Zhou H, Seifter J, Ying L, Mikhailovsky A, Heeger AJ, Bazan GC, Nguyen TQ (2013) Molecular doping enhances photoconductivity in polymer bulk heterojunction solar cells. Adv Mater 25:7038–7044CrossRef

Facchetti A (2013) Polymer donor-polymer acceptor (all-polymer) solar cells. Mater Today 16:123–132CrossRef

Stalder R, Mei J, Graham KR, Estrada LA, Reynolds JR (2014) Isoindigo, a versatile electron-deficient unit for high-performance organic electronics. Chem Mater 26:664–678CrossRef

10.

Halls JJM, Walsh CA, Greenham NC, Marseglia EA, Friend RH, Moratti SC, Holmes AB (1995) Efficient photodiodes from interpenetrating polymer networks. Nature 376:498–500CrossRef

11.

Granström M, Petritsch K, Arias AC, Lux A, Andersson MR, Friend RH (1998) Laminated fabrication of polymeric photovoltaic diodes. Nature 395:257–260CrossRef

12.

Holcombe TW, Woo CH, Kavulak DFJ, Thompson BC, Fréchet JMJ (2009) All-polymer photovoltaic devices of poly(3-(4-n-octyl)-phenylthiophene) from Grignard metathesis (GRIM) polymerization. J Am Chem Soc 131:14160–14161CrossRef

13.

Zhan X, Tan Z, Zhou E, Li Y, Misra R, Grant A, Domercq B, Zhang XH, An Z, Zhang X, Barlow S, Kippelen B, Marder SR (2009) Copolymers of perylene diimide with dithienothiophene and dithienopyrrole as electron-transport materials for all-polymer solar cells and field-effect transistors. J Mater Chem 19:5794–5803CrossRef

14.

Zhou E, Cong J, Hashimoto K, Tajima K (2013) Control of miscibility and aggregation via the material design and coating process for high-performance polymer blend solar cells. Adv Mater 25:6991–6996CrossRef

15.

Earmme T, Hwang YJ, Murari NM, Subramaniyan S, Jenekhe SA (2013) All-polymer solar cells with 3.3 % efficiency based on naphthalene diimide-selenophene copolymer acceptor. J Am Chem Soc 135:14960–14963CrossRef

16.

Salim T, Sun S, Wong LH, Xi L, Foo YL, Lam YM (2010) The role of poly(3-hexylthiophene) nanofibers in an all-polymer blend with a polyfluorene copolymer for solar cell applications. J Phys Chem C 114:9459–9468CrossRef

17.

Mori D, Benten H, Ohkita H, Ito S, Miyake K (2012) Polymer/polymer blend solar cells improved by using high-molecular-weight fluorene-based copolymer as electron acceptor. ACS Appl Mater Interfaces 4:3325–3329CrossRef

18.

Cao Y, Lei T, Yuan J, Wang JY, Pei J (2013) Dithiazolyl-benzothiadiazole-containing polymer acceptors: synthesis, characterization, and all-polymer solar cells. Polym Chem 4:5228–5236CrossRef

19.

Sang G, Zou Y, Huang Y, Zhao G, Yang Y, Li Y (2009) All-polymer solar cells based on a blend of poly[3-(10-n-octyl-3-phenothiazine-vinylene)thiophene-co-2,5-thiophene] and poly[1,4-dioctyloxyl-p-2,5-dicyanophenylenevinylene]. Appl Phys Lett 94:193302-1–193302-3CrossRef

20.

Vijayakumar C, Saeki A, Seki S (2012) Optoelectronic properties of dicyanofluorene-based n-type polymers. Chem Asian J 7:1845–1852CrossRef

21.

Wong WY (2008) Metallopolyyne polymers as new functional materials for photovoltaic and solar cell applications. Macromol Chem Phys 209:14–24CrossRef

22.

Wong WY, Ho CL (2010) Organometallic photovoltaics: a new and versatile approach for harvesting solar energy using conjugated polymetallaynes. Acc Chem Res 43:1246–1256CrossRef

23.

Ho CL, Wong WY (2011) Metal-containing polymers: facile tuning of photophysical traits and emerging applications in organic electronics and photonics. Coord Chem Rev 225:2469–2502CrossRef

24.

Köhler A, Wittmann HF, Friend RH, Khan MS, Lewis J (1996) Enhanced photocurrent response in photocells made with platinum-poly-yne/C₆₀ blends by photoinduced electron transfer. Synth Met 77:147–150CrossRef

25.

Guo F, Kim YG, Reynolds JR, Schanze KS (2006) Platinum-acetylide polymer based solar cells: involvement of the triplet state for energy conversion. Chem Commun 42:1887–1889

26.

Wong WY, Wang XZ, He Z, Djurišić AB, Yip CT, Cheung KY, Wang H, Mak CSK, Chan WK (2007) Metallated conjugated polymers as a new avenue towards high-efficiency polymer solar cells. Nat Mater 6:521–527CrossRef

27.

Wu PT, Bull T, Kim FS, Luscombe CK, Jenekhe SA (2009) Organometallic donor-acceptor conjugated polymer semiconductors: tunable optical, electrochemical, charge transport, and photovoltaic properties. Macromolecules 42:671–681CrossRef

28.

Baek NS, Hau SK, Yip HL, Acton O, Chen KS, Jen AKY (2008) High performance amorphous metallated π-conjugated polymers for field-effect transistors and polymer solar cells. Chem Mater 20:5734–5736CrossRef

29.

Mei J, Ogawa K, Kim YG, Heston NC, Arenas DJ, Nasrollahi Z, McCarley TD, Tanner DB, Reynolds JR, Schanze KS (2009) Low-band-gap platinum acetylide polymers as active materials for organic solar cells. ACS Appl Mater Interfaces 1:150–161CrossRef

30.

Wong WY, Wang XZ, He Z, Chan KK, Djurišić AB, Cheung KY, Yip CT, Ng AMC, Xi YY, Mak CSK, Chan WK (2007) Tuning the absorption, charge transport properties, and solar cell efficiency with the number of thienyl rings in platinum-containing poly(aryleneethynylene)s. J Am Chem Soc 129:14372–14380CrossRef

31.

Liu L, Ho CL, Wong WY, Cheung KY, Fung MK, Lam WT, Djurišić AB, Chan WK (2008) Effect of oligothienyl chain length on tuning the solar cell performance in fluorene-based polyplatinynes. Adv Funct Mater 18:2824–2833CrossRef

32.

Wong WY, Chow WC, Cheung KY, Fung MK, Djurišić AB, Chan WK (2009) Harvesting solar energy using conjugated metallopolyyne donors containing electron-rich phenothiazine-oligothiophene moieties. J Organomet Chem 694:2717–2726CrossRef

33.

Li L, Chow WC, Wong WY, Chui CH, Wong RSM (2011) Synthesis, characterization and photovoltaic behavior of platinum acetylide polymers with electron-deficient 9,10-anthraquinone moiety. J Organomet Chem 696:1189–1197CrossRef

34.

Zhan H, Wong WY, Ng A, Djurišić AB, Chan WK (2011) Synthesis, characterization and photovoltaic properties of platinum-containing poly(aryleneethynylene) polymers with phenanthrenyl-imidazole moiety. J Organomet Chem 696:4112–4120CrossRef

35.

Zhan H, Lamare S, Ng A, Kenny T, Guernon H, Chan WK, Djurišić AB, Harvey PD, Wong WY (2011) Synthesis and photovoltaic properties of new metalloporphyrin-containing polyplatinyne polymers. Macromolecules 44:5155–5167CrossRef

36.

Wang Q, Wong WY (2011) New low-bandgap polymetallaynes of platinum functionalized with a triphenylamine-benzothiadiazole donor-acceptor unit for solar cell applications. Polym Chem 2:432–440CrossRef

37.

Cyr PW, Klem EJD, Sargent EH, Manners I (2005) Photoconductivity in donor-acceptor polyferrocenylsilane-fullerene composite films. Chem Mater 17:5770–5773CrossRef

38.

Padhy H, Sahu D, Chiang IH, Patra D, Kekuda D, Chu CW, Lin HC (2011) Synthesis and applications of main-chain Ru(II) metallo-polymers containing bis-terpyridyl ligands with various benzodiazole cores for solar cells. J Mater Chem 21:1196–1205CrossRef

39.

Feng K, Shen X, Li Y, He Y, Huang D, Peng Q (2013) Ruthenium(II) containing supramolecular polymers with cyclopentadithiophene-benzothiazole conjugated bridges for photovoltaic applications. Polym Chem 4:5701–5710CrossRef

40.

Liao CY, Chen CP, Chang CC, Hwang GW, Chou HH, Cheng CH (2013) Synthesis of conjugated polymers bearing indacenodithiophene and cyclometalated platinum(II) units and their application in organic photovoltaics. Sol Energy Mater Sol Cells 109:111–119CrossRef

41.

Mak CSK, Cheung WK, Leung QY, Chan WK (2010) Conjugated copolymers containing low bandgap rhenium(I) complexes. Macromol Rapid Commun 31:875–882CrossRef

42.

Kimoto A, Tajima Y (2012) Donor-acceptor-type low bandgap polymer carrying phenylazomethine moiety as a metal-collecting pendant unit: open-circuit voltage modulation of solution-processed organic photovoltaic devices induced by metal complexation. ACS Macro Lett 1:667–671CrossRef

43.

Guo F, Ogawa K, Kim YG, Danilov EO, Castellano FN, Reynolds JR, Schanze KS (2007) A fulleropyrrolidine end-capped platinum-acetylide triad: the mechanism of photoinduced charge transfer in organometallic photovoltaic cells. Phys Chem Chem Phys 9:2724–2734CrossRef

44.

Liu S, Zhang K, Lu J, Zhang J, Yip HL, Huang F, Cao Y (2013) High-efficiency polymer solar cells via the incorporation of an amino-functionalized conjugated metallopolymer as a cathode interlayer. J Am Chem Soc 135:15326–15329CrossRef

45.

Rodríguez JG, Lafuente A, Martín-Villamil R, Martínez-Alcazar MP (2001) Synthesis and structural analysis of 1,4-bis[n-(N,N-dimethylamino)pheny]buta-1,3-diynes and charge-transfer complexes with TCNE. J Phys Org Chem 14:859–868CrossRef

46.

Michinobu T, May JS, Lim JH, Boudon C, Gisselbrecht JP, Seiler P, Gross M, Biaggio I, Diederich F (2005) A new class of organic donor-acceptor molecules with large third-order optical nonlinearities. Chem Commun 41:737–739

47.

Kivala M, Diederich F (2009) Acetylene-derived strong organic acceptors for planar and nonplanar push-pull chromophores. Acc Chem Res 42:235–248CrossRef

48.

Kato SI, Diederich F (2010) Non-planar push-pull chromophores. Chem Commun 46:1994–2006CrossRef

49.

Michinobu T (2011) Adapting semiconducting polymer doping techniques to create new types of click postfunctionalization. Chem Soc Rev 40:2306–2316CrossRef

50.

Michinobu T, Li Y, Hyakutake T (2013) Polymeric ion sensors with multiple detection modes achieved by a new type of click chemistry reaction. Phys Chem Chem Phys 15:2623–2631CrossRef

51.

Kato SI, Kivala M, Schweizer WB, Boudon C, Gisselbrecht JP, Diederich F (2009) Origin of intense intramolecular charge-transfer interactions in nonplanar push-pull chromophores. Chem Eur J 15:8687–8691CrossRef

52.

Kivala M, Boudon C, Gisselbrecht JP, Seiler P, Gross M, Diederich F (2007) Charge-transfer chromophores by cycloaddition-retroelectrocyclization: multivalent systems and cascade reactions. Angew Chem Int Ed 46:6357–6360CrossRef

53.

Silvestri F, Jordan M, Howes K, Kivala M, Rivera-Fuentes P, Boudon C, Gisselbrecht JP, Schweizer WB, Seiler P, Chiu M, Diederich F (2011) Regular acyclic and macrocyclic [AB] oligomers by formation of push-pull chromophores in the chain-growth step. Chem Eur J 17:6088–6097CrossRef

54.

Kivala M, Boudon C, Gisselbrecht JP, Enko B, Seiler P, Müller IB, Langer N, Jarowski PD, Gescheidt G, Diederich F (2009) Organic super-acceptors with efficient intramolecular charge-transfer interactions by [2 + 2] cycloadditions of TCNE, TCNQ, and F₄-TCNQ to donor-substituted cyanoalkynes. Chem Eur J 15:4111–4123CrossRef

55.

Leliège A, Blanchard P, Rousseau T, Roncali J (2011) Triphenylamine/tetracyanobutadiene-based D-A-D π-conjugated systems as molecular donors for organic solar cells. Org Lett 13:3098–3101CrossRef

56.

Ohshita J, Kajihara T, Tanaka D, Ooyama Y (2014) Preparation of poly(disilanylenetetracyanobutadienyleneoligothienylene)s as new donor-acceptor type organosilicon polymers. J Organomet Chem 749:255–260CrossRef

57.

Michinobu T, Satoh N, Cai J, Li Y, Han L (2014) Novel design of organic donor-acceptor dyes without carboxylic acid anchoring groups for dye-sensitized solar cells. J Mater Chem C 2:3367–3372CrossRef

58.

Bruce MI, Rodgers JR, Snow MR, Swincer AG (1981) Cyclopentadienyl-ruthenium and –osmium chemistry. cleavage of tetracyanoethylene under mild conditions: X-ray crystal structures of [Ru{η³-C(CN)₂CPhC = C(CN)₂}(PPh₃)(η-C₅H₅)] and [Ru{C[=C(CN)₂]CPh = C(CN)₂}(CNBu^t)(PPh₃)(η-C₅H₅)]. J Chem Soc Chem Commun 17:271–272

59.

Bruce MI (2013) Reactions of polycyano-alkenes with alkynyl- and poly-ynyl-Group 8 metal complexes. J Organomet Chem 730:3–19CrossRef

60.

Onitsuka K, Takahashi S (1995) Synthesis and structure of s-cis- and s-trans-μ-butadiene-2,3-diyldiplatinum complexes by the reaction of μ-ethynediyldiplatinum complexes with tetracyanoethylene. J Chem Soc Chem Commun 31:2095–2096

61.

Onitsuka K, Ose N, Ozawa F, Takahashi S (1999) Reactions of acetylene-bridged diplatinum complexes with tetracyanoethylene. J Organomet Chem 578:169–177CrossRef

62.

Tchitchanov BH, Chiu M, Jordan M, Kivala M, Schweizer WB, Diederich F (2013) Platinum(II) acetylides in the formal [2+2] cycloaddition-retroelectrocyclization reaction: organodonor versus metal activation. Eur J Org Chem 2013:3729–3740

63.

Sonogashira K, Morimoto H, Takai Y, Takahashi S (1981) Reactions of metal poly-yne polymers with free phosphines, coordinated phosphines, carbon monoxide, and tetracyanoethylene. Symp Organomet Chem Jpn 28:64–66

64.

Yuan Y, Michinobu T (2012) Construction of donor-acceptor chromophores in platinum polyyne polymer by [2 + 2] cycloaddition of organic acceptors. Macromol Chem Phys 213:2114–2119CrossRef

65.

Yuan Y, Michinobu T, Oguma J, Kato T, Miyake K (2013) Attempted inversion of semiconducting features of platinum polyyne polymers: a new approach for all-polymer solar cells. Macromol Chem Phys 214:1465–1472CrossRef

66.

Michinobu T (2008) Click-type reaction of aromatic polyamines for improvement of thermal and optoelectronic properties. J Am Chem Soc 130:14074–14075CrossRef

67.

Michinobu T, Seo C, Noguchi K, Mori T (2012) Effects of click postfunctionalization on thermal stability and field effect transistor performances of aromatic polyamines. Polym Chem 3:1427–1435CrossRef

Titel: All-Polymer Solar Cells Based on Organometallic Polymers
verfasst von: Tsuyoshi Michinobu
Verlag: Springer Berlin Heidelberg
Buch: Organometallics and Related Molecules for Energy Conversion
Print ISBN: 978-3-662-46053-5

Electronic ISBN: 978-3-662-46054-2

Copyright-Jahr: 2015
DOI: https://doi.org/10.1007/978-3-662-46054-2_5