Organic thin-film solar cells using electron-donating perylene tetracarboxylic acid derivatives

Yuki Shibano, Hiroshi Imahori, Chihaya Adachi

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

Various electron-donating amino groups were introduced into the perylene core of perylene tetracarboxylic acid derivatives (PTCs) to address the potential use in organic solar cells. Broad absorptions of the PTC solutions in the visible to near-infrared (NIR) region suggest that PTCs are promising light-harvesting molecules for solar cells. Electrochemical measurements reveal that the introduction of the electron-donating amino groups makes the energy level of the highest occupied molecular orbital (HOMO) shallow, imparting electronrich characteristics to the PTCs. The electronic properties of the PTCs are studied on the basis of quantum chemical calculations. The results show that the variation of the amino groups has a significant influence on the HOMO level, while the lowest unoccupied molecular orbital (LUMO) level is relatively sensitive to the electronegativity of the PTC terminal atoms. The PTC thin films exhibit broad absorption bands in the visible to NIR region, as for the PTC solutions, and possess relatively shallow HOMO and LUMO energies that are higher or comparable to those of fullerene C60. These excellent properties encouraged us to employ aminesubstituted PTCs as electron donors in a thin film solar cell with C60 as an n-type semiconductor. Photovoltaic devices with a structure of indium tin oxide (ITO)/PTCs/C60/bathocuproine (BCP)/Al were fabricated by spin-coating PTCs on an ITO electrode. The devices with perylene tetracarboxylic acid diimides (PTCDIs), bearing highly basic amino groups (Py-PTCDI, Me2N-PTCDI, and Ph2N-PTCDI), exhibit the higher power conversion efficiencies than those with carbazoyl PTCDI (Cz-PTCDI) and perylene tetracarboxylic acid dianhydrides (PTCDAs). The higher device performance originates from the efficient electron transfer from the PTCs to C60 as the results of the relatively shallow HOMO and LUMO levels of the PTCs bearing the highly basic amino groups. The dependence of the device performan the PTC film thickness indicates that the introduction of diphenylamino groups on the perylene core suppresses the nonradiative decay of the exciton without decreasing the hole mobility. These results will provide important information for the molecular design of post PTC derivatives.

Original languageEnglish
Pages (from-to)15454-15466
Number of pages13
JournalJournal of Physical Chemistry C
Volume113
Issue number34
DOIs
Publication statusPublished - Aug 27 2009

Fingerprint

Perylene
Factor IX
Molecular orbitals
molecular orbitals
solar cells
Derivatives
acids
Acids
Electrons
thin films
Bearings (structural)
electrons
Tin oxides
indium oxides
Indium
tin oxides
Infrared radiation
Electronegativity
Hole mobility
n-type semiconductors

All Science Journal Classification (ASJC) codes

  • Electronic, Optical and Magnetic Materials
  • Energy(all)
  • Physical and Theoretical Chemistry
  • Surfaces, Coatings and Films

Cite this

Organic thin-film solar cells using electron-donating perylene tetracarboxylic acid derivatives. / Shibano, Yuki; Imahori, Hiroshi; Adachi, Chihaya.

In: Journal of Physical Chemistry C, Vol. 113, No. 34, 27.08.2009, p. 15454-15466.

Research output: Contribution to journalArticle

@article{4c0db9a6e01f42e6855586e96fb2dfd2,
title = "Organic thin-film solar cells using electron-donating perylene tetracarboxylic acid derivatives",
abstract = "Various electron-donating amino groups were introduced into the perylene core of perylene tetracarboxylic acid derivatives (PTCs) to address the potential use in organic solar cells. Broad absorptions of the PTC solutions in the visible to near-infrared (NIR) region suggest that PTCs are promising light-harvesting molecules for solar cells. Electrochemical measurements reveal that the introduction of the electron-donating amino groups makes the energy level of the highest occupied molecular orbital (HOMO) shallow, imparting electronrich characteristics to the PTCs. The electronic properties of the PTCs are studied on the basis of quantum chemical calculations. The results show that the variation of the amino groups has a significant influence on the HOMO level, while the lowest unoccupied molecular orbital (LUMO) level is relatively sensitive to the electronegativity of the PTC terminal atoms. The PTC thin films exhibit broad absorption bands in the visible to NIR region, as for the PTC solutions, and possess relatively shallow HOMO and LUMO energies that are higher or comparable to those of fullerene C60. These excellent properties encouraged us to employ aminesubstituted PTCs as electron donors in a thin film solar cell with C60 as an n-type semiconductor. Photovoltaic devices with a structure of indium tin oxide (ITO)/PTCs/C60/bathocuproine (BCP)/Al were fabricated by spin-coating PTCs on an ITO electrode. The devices with perylene tetracarboxylic acid diimides (PTCDIs), bearing highly basic amino groups (Py-PTCDI, Me2N-PTCDI, and Ph2N-PTCDI), exhibit the higher power conversion efficiencies than those with carbazoyl PTCDI (Cz-PTCDI) and perylene tetracarboxylic acid dianhydrides (PTCDAs). The higher device performance originates from the efficient electron transfer from the PTCs to C60 as the results of the relatively shallow HOMO and LUMO levels of the PTCs bearing the highly basic amino groups. The dependence of the device performan the PTC film thickness indicates that the introduction of diphenylamino groups on the perylene core suppresses the nonradiative decay of the exciton without decreasing the hole mobility. These results will provide important information for the molecular design of post PTC derivatives.",
author = "Yuki Shibano and Hiroshi Imahori and Chihaya Adachi",
year = "2009",
month = "8",
day = "27",
doi = "10.1021/jp9045726",
language = "English",
volume = "113",
pages = "15454--15466",
journal = "Journal of Physical Chemistry C",
issn = "1932-7447",
publisher = "American Chemical Society",
number = "34",

}

TY - JOUR

T1 - Organic thin-film solar cells using electron-donating perylene tetracarboxylic acid derivatives

AU - Shibano, Yuki

AU - Imahori, Hiroshi

AU - Adachi, Chihaya

PY - 2009/8/27

Y1 - 2009/8/27

N2 - Various electron-donating amino groups were introduced into the perylene core of perylene tetracarboxylic acid derivatives (PTCs) to address the potential use in organic solar cells. Broad absorptions of the PTC solutions in the visible to near-infrared (NIR) region suggest that PTCs are promising light-harvesting molecules for solar cells. Electrochemical measurements reveal that the introduction of the electron-donating amino groups makes the energy level of the highest occupied molecular orbital (HOMO) shallow, imparting electronrich characteristics to the PTCs. The electronic properties of the PTCs are studied on the basis of quantum chemical calculations. The results show that the variation of the amino groups has a significant influence on the HOMO level, while the lowest unoccupied molecular orbital (LUMO) level is relatively sensitive to the electronegativity of the PTC terminal atoms. The PTC thin films exhibit broad absorption bands in the visible to NIR region, as for the PTC solutions, and possess relatively shallow HOMO and LUMO energies that are higher or comparable to those of fullerene C60. These excellent properties encouraged us to employ aminesubstituted PTCs as electron donors in a thin film solar cell with C60 as an n-type semiconductor. Photovoltaic devices with a structure of indium tin oxide (ITO)/PTCs/C60/bathocuproine (BCP)/Al were fabricated by spin-coating PTCs on an ITO electrode. The devices with perylene tetracarboxylic acid diimides (PTCDIs), bearing highly basic amino groups (Py-PTCDI, Me2N-PTCDI, and Ph2N-PTCDI), exhibit the higher power conversion efficiencies than those with carbazoyl PTCDI (Cz-PTCDI) and perylene tetracarboxylic acid dianhydrides (PTCDAs). The higher device performance originates from the efficient electron transfer from the PTCs to C60 as the results of the relatively shallow HOMO and LUMO levels of the PTCs bearing the highly basic amino groups. The dependence of the device performan the PTC film thickness indicates that the introduction of diphenylamino groups on the perylene core suppresses the nonradiative decay of the exciton without decreasing the hole mobility. These results will provide important information for the molecular design of post PTC derivatives.

AB - Various electron-donating amino groups were introduced into the perylene core of perylene tetracarboxylic acid derivatives (PTCs) to address the potential use in organic solar cells. Broad absorptions of the PTC solutions in the visible to near-infrared (NIR) region suggest that PTCs are promising light-harvesting molecules for solar cells. Electrochemical measurements reveal that the introduction of the electron-donating amino groups makes the energy level of the highest occupied molecular orbital (HOMO) shallow, imparting electronrich characteristics to the PTCs. The electronic properties of the PTCs are studied on the basis of quantum chemical calculations. The results show that the variation of the amino groups has a significant influence on the HOMO level, while the lowest unoccupied molecular orbital (LUMO) level is relatively sensitive to the electronegativity of the PTC terminal atoms. The PTC thin films exhibit broad absorption bands in the visible to NIR region, as for the PTC solutions, and possess relatively shallow HOMO and LUMO energies that are higher or comparable to those of fullerene C60. These excellent properties encouraged us to employ aminesubstituted PTCs as electron donors in a thin film solar cell with C60 as an n-type semiconductor. Photovoltaic devices with a structure of indium tin oxide (ITO)/PTCs/C60/bathocuproine (BCP)/Al were fabricated by spin-coating PTCs on an ITO electrode. The devices with perylene tetracarboxylic acid diimides (PTCDIs), bearing highly basic amino groups (Py-PTCDI, Me2N-PTCDI, and Ph2N-PTCDI), exhibit the higher power conversion efficiencies than those with carbazoyl PTCDI (Cz-PTCDI) and perylene tetracarboxylic acid dianhydrides (PTCDAs). The higher device performance originates from the efficient electron transfer from the PTCs to C60 as the results of the relatively shallow HOMO and LUMO levels of the PTCs bearing the highly basic amino groups. The dependence of the device performan the PTC film thickness indicates that the introduction of diphenylamino groups on the perylene core suppresses the nonradiative decay of the exciton without decreasing the hole mobility. These results will provide important information for the molecular design of post PTC derivatives.

UR - http://www.scopus.com/inward/record.url?scp=69549133892&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=69549133892&partnerID=8YFLogxK

U2 - 10.1021/jp9045726

DO - 10.1021/jp9045726

M3 - Article

AN - SCOPUS:69549133892

VL - 113

SP - 15454

EP - 15466

JO - Journal of Physical Chemistry C

JF - Journal of Physical Chemistry C

SN - 1932-7447

IS - 34

ER -