Description of the publication:

Authors:

Iwan, A., Palewicz, M., Chuchmała, A., Sikora, A., Górecki, L., Sęk, D.

Title:

Opto(electrical) properties of triphenylamine–based polyazomethine and its blend with [6,6]–phenyl C61 butyric acid methyl ester

Journal:

High Performance Polymers

Year:

2013

Vol:

25 (7)

Pages:

832–842

ISSN/ISBN:

09540083

DOI:

10.1177/0954008313486818

Link:

http://hip.sagepub.com/content/25/7/832.abstract/

Keywords:

Polyazomethines; polymer solar cells; triphenylamine–based polymers

Abstract:

Polyazomethine (OFBF–TPA) based on triphenylamine (TPA) and octafluorobiphenyl (OFBF) moieties was tested as donor–acceptor (D–A) for bulk heterojunction polymeric solar cells. The temperatures of 5% weight loss (T5%) of the polyazomethine range from 323 to 328 C, depending on the gas used (air and nitrogen). The conductivity of OFBF–TPA was approximately 10–10 S/cm for not annealed sample and at about 10–6 S/cm for the ones annealed at room temperature, as determined by impedance spectroscopy. Surface of the polymer and mixture polymer–[6,6]–phenyl C61 butyric acid methyl ester (PCBM) was smooth with the Rms value in the range 0.58–1.95 nm as was detected by the atomic force microscopy (AFM) technique. UV–VIS spectrum of the mixture OFBF–TPA–PCBM exhibited higher absorption intensity than the UV–vis spectrum of OFBF–TPA lacking PCBM. The thin solid film of OFBF–TPA and OFBF–TPA–PCBM showed one main absorption band with a maximum peak at 414 and 411 nm, respectively. For the mixture OFBF–TPA–PCBM, the second absorption band at 333 nm was found. No influence of annealing on the absorption properties was observed. The polymer solar cell devices were fabricated by spin coating the blend solution of the OFBF–TPA and PCBM and investigated in dark and under an illumination of 100 mW/cm2, with an AM1.5 G. Electrical behavior of the device indium tin oxide (ITO)/poly(3,4–ethylenedioxythiophene) (PEDOT)– poly(styrenesulfonate) (PSS)/OFBF–TPA–PCBM/Al was tested by impedance spectroscopy in dark and under illumination. For all measured devices, Nyquist plots were presented. The annealing significantly improved the electrical conductivity of the investigated devices. Electrical and photovoltaic properties of OFBF–TPA were compared with the properties of polyazomethine based on TPA and fluorene moieties (F–TPA).

References:

♦ Iwan, A., Sęk, D., Polymers with triphenylamine units: Photonic and electroactive materials (2011) Prog Polym Sci, 36, pp. 1277–1325
♦ Sęk, D., Iwan, A., Jarząbek, B., Kaczmarczyk, B., Kasperczyk, J., Mazurak, Z., Hole transport triphenylamine–azomethine conjugated system: Synthesis and optical, photoluminescence and electrochemical properties (2008) Macromol, 41, pp. 6653–6663
♦ Bernius, M.T., Inbasekaran, M., O'Brien, J., Wu, W.S., Progress with light–emitting polymers (2000) Adv Mater, 12, pp. 1737–1750
♦ Sęk, D., Iwan, A., Jarząbek, B., Kaczmarczyk, B., Kasperczyk, J., Janeczek, H., Characterization and optical properties of oligoazomethines with triphenylamine moieties exhibiting blue, blue–green and green light (2009) Spectrochim Acta A: Mol Biomol Spect, 72, pp. 1–10
♦ Niu, H., Huang, Y., Bai, X., Li, X., Zhang, G., Study on crystallization, thermal stability and hole transport properties of conjugated polyazomethine materials containing 4,4'–bisamine–triphenylamine (2004) Mater Chem Phys, 86, pp. 33–37
♦ Niu, H.–J., Huang, Y.–D., Bai, X.–D., Li, X., Novel poly–Schiff bases containing 4,4'–diamino–triphenylamine as hole transport material for organic electronic device (2004) Mater Lett, 58, pp. 2979–2983
♦ Palewicz, M., Iwan, A., Sibiński, M., Sikora, A., Mazurek, B., Organic photovoltaic devices based on polyazomethine and fullerene (2011) Energ Procedia, 3, pp. 84–91
♦ Iwan, A., Schab–Balcerzak, E., Pociecha, D., Krompiec, M., Grucela, M., Janeczek, H., Characterization, liquid crystalline behavior, electrochemical and optoelectrical properties of new poly(azomethine)s and poly(imide) with siloxane linkages (2011) Opt Mat, 34, pp. 61–74
♦ Jarząbek, B., Weszka, J., Domański, M., Cisowski, J., Optical properties of amorphous polyazomethine thin films (2006) J Non–Cryst Solids, 352, pp. 1660–1662
♦ Barik, S., Bishop, S., Skene, W.G., Spectroelectrochemical and electrochemical investigation of a highly conjugated all–thiophene polyazomethine (2011) Mater Chem Phys, 129, pp. 529–533
♦ Hindson, J.C., Ulgut, B., Friend, R.H., Greenham, N.C., Norder, B., Kotlewski, A., All–aromatic liquid crystal triphenylamine–based poly(azomethine)s as hole transport materials for opto–electronic applications (2010) J Mater Chem, 20, pp. 937–944
♦ Sharma, G.D., Sandogaker, S.G., Roy, M.S., Electrical and photoelectrical properties of poly(phenyl azomethine furane) thin films devices (1996) Thin Solid Films, 278, pp. 129–134
♦ Iwan, A., Palewicz, M., Sikora, A., Chmielowiec, J., Hreniak, A., Paściak, G., Aliphatic–aromatic poly(azomethine)s with ester groups as thermotropic materials for opto(electronic) applications (2010) Synt Met, 160, pp. 1856–1867
♦ Iwan, A., Palewicz, M., Chuchmała, A., Górecki, L., Sikora, A., Mazurek, B., Opto(electrical) properties of new aromatic polyazomethines with fluorene moieties in the main chain for polymeric photovoltaic devices (2012) Synt Met, 162, pp. 143–153
♦ Palewicz, M., Iwan, A., Sikora, A., Doskocz, J., Stręk, W., Sęk, D., Optical, structural and electrical properties of aromatic triphenylamine–based poly(azomethine)s in thin layers (2012) Acta Physica Polonica A, 121, pp. 439–444
♦ Bundgaard, E., Krebs, F.C., Low band gap polymers for organic photovoltaics (2007) Sol Energ Mat Sol C, 91, pp. 954–985
♦ Günes, S., Neugebauer, H., Sariciftci, N.S., Conjugated polymer–based organic solar cells (2007) Chem Rev, 107, pp. 1324–1338
♦ Thompson, B.C., Fréchet, J.M.J., Polymer–fullerene composite solar cells (2008) Angew Chem Int Ed, 47, pp. 58–77
♦ Godlewski, J., Currents and photocurrents in organic materials determined by the interface phenomena (2005) Adv Colloid Interf Sci, 116, pp. 227–243
♦ Venkataraman, D., Yurt, S., Venkatraman, B.H., Gavvalapalli, N., Role of molecular architecture in organic photovoltaic cells (2010) J Phys Chem Lett, 1, pp. 947–958
♦ Zhan, X., Zhu, D., Conjugated polymers for high–efficiency organic photovoltaics (2010) Polym Chem, 1, pp. 409–419
♦ Chen, J.T., Hsu, C.S., Conjugated polymer nanostructures for organic solar cell applications (2011) Polym Chem, 2, pp. 2707–2722
♦ Dennler, G., Scharber, M.C., Brabec, C.J., Polymer–fullerene bulk–heterojunction solar cells (2009) Adv Mater, 21, pp. 1323–1338
♦ Nunzi, J.M., Organic photovoltaic materials and devices (2002) C R Physique, 3, pp. 523–542
♦ Moliton, A., Nunzi, J.M., How to model the behaviour of organic photovoltaic cells (2006) Polym Int, 55, pp. 583–600
♦ Shin, M., Kim, H., Kim, Y., Effect of film and device annealing in polymer: Polymer solar cells with a LiF nanolayer (2011) Mater Sci Eng B, 176, pp. 382–386
♦ Krebs, F.C., Fyenbo, J., Tanenbaum, D.M., Gevorgyan, S.A., Andriessen, R., Van Remoortere, B., The OE–A OPV demonstrator anno domini 2011 (2011) Energy Environ Sci, 4, pp. 4116–4123
♦ Espinosa, N., Hosel, M., Angmo, D., Krebs, F.C., Solar cells with one–day energy payback for the factories of the future (2012) Energy Environ Sci, 5, pp. 5117–5132
♦ Rusu, G.I., Airinei, A., Rusu, M., Prepelit, P., Marin, L., Cozan, V., On the electronic transport mechanism in thin films of some new poly(azomethine sulfone)s (2007) Acta Mater, 55, pp. 433–442
♦ Jarząbek, B., Weszka, J., Burian, A., Pocztowski, G., Optical properties of amorphous thin films of the ZnP system (1996) Thin Solid Films, 279, pp. 204–208
♦ Garcia–Belmonte, G., Munar, A., Barea, E.M., Bisquert, J., Ugarte, I., Pacios, R., Charge carrier mobility and lifetime of organic bulk heterojunctions analyzed by impedance spectroscopy (2008) Org Electr, 9, pp. 847–851
♦ Leever, B.J., Bailey, C.A., Marks, T.J., Hersam, M.C., Durstock, M.F., In situ characterization of lifetime and morphology in operating bulk heterojunction organic photovoltaic devices by impedance spectroscopy (2012) Adv. Energy Mater, 2, pp. 120–128
♦ Huang, W.B., Peng, J.B., Wang, L., Investigation of annealing effects on microstructure of hybrid nanocrystal–polymer solar cells by impedance spectroscopy (2010) Synth Met, 160, pp. 445–449
♦ Kim, C.H., Kisiel, K., Jung, J., Ulański, J., Tondelier, D., Geffroya, B., Persistent photoexcitation effect on the poly(3–hexylthiophene) film: Impedance measurement and modeling (2012) Synth Met, 162, pp. 460–465

Example figure:

3D topography view of the polyazomethine (OFBF-TPA) based on triphenylamine.