Di(4-methylphenyl)methano-C60 bis-adduct for efficient and stable organic photovoltaics with enhanced open-circuit voltage

Yen Ju Cheng, Ming Hung Liao, Chih Yu Chang, Wei Shun Kao, Cheng En Wu, Chain Shu Hsu

Research output: Contribution to journalArticle

88 Citations (Scopus)

Abstract

A new class of fullerene bis-adducts-di(4-methylphenyl)methano-C 60 bis-adduct (DMPCBA), di(4-fluorophenyl)methano-C60 bis-adduct (DFPCBA), and diphenylmethano-C60 bis-adduct (DPCBA)-were rationally designed and easily synthesized. Compared to the lowest unoccupied molecular orbital (LUMO) energy level of PC61BM (-3.95 eV), the double functionalization effectively raises the LUMO energy levels of these fullerene materials to ca.-3.85 eV, regardless of the substituent groups (CH3-, F-, and H-) at the para-position of the phenyl rings. This phenomenon suggests that the plane of the phenyl groups is preferentially parallel to the fullerene surface, leading to poor orbital interactions with C60 and negligible electronic effect. Importantly, such geometry sterically protects and shields the core C60 structure from severe intermolecular aggregation, rendering it intrinsically soluble, morphologically amorphous, and thermally stable. The device based on the P3HT:DMPCBA blend exhibited an open-circuit voltage (Voc) of 0.87 V, a short-circuit current density (Jsc) of 9.05 mA/cm2, and a fill factor (FF) of 65.5%, leading to a high power conversion efficiency (PCE) of 5.2%, which is superior to that of the P3HT:PC61BM-based device. Most significantly, the amorphous nature of DMPCBA effectively suppresses the thermal-driven aggregation and thus stabilizes the morphology of the P3HT:DMPCBA blend. Consequently, the device retained 80% of its original PCE value against thermal heating at 160 °C over 20 h.

Original languageEnglish
Pages (from-to)4056-4062
Number of pages7
JournalChemistry of Materials
Volume23
Issue number17
DOIs
Publication statusPublished - Sep 13 2011
Externally publishedYes

Fingerprint

Fullerenes
Open circuit voltage
Molecular orbitals
Electron energy levels
Conversion efficiency
Agglomeration
Short circuit currents
Current density
Heating
Geometry
Hot Temperature

Keywords

  • C bis-adduct
  • morphological stability
  • open-circuit voltage
  • organic photovoltaics

ASJC Scopus subject areas

  • Materials Chemistry
  • Chemical Engineering(all)
  • Chemistry(all)

Cite this

Di(4-methylphenyl)methano-C60 bis-adduct for efficient and stable organic photovoltaics with enhanced open-circuit voltage. / Cheng, Yen Ju; Liao, Ming Hung; Chang, Chih Yu; Kao, Wei Shun; Wu, Cheng En; Hsu, Chain Shu.

In: Chemistry of Materials, Vol. 23, No. 17, 13.09.2011, p. 4056-4062.

Research output: Contribution to journalArticle

Cheng, Yen Ju ; Liao, Ming Hung ; Chang, Chih Yu ; Kao, Wei Shun ; Wu, Cheng En ; Hsu, Chain Shu. / Di(4-methylphenyl)methano-C60 bis-adduct for efficient and stable organic photovoltaics with enhanced open-circuit voltage. In: Chemistry of Materials. 2011 ; Vol. 23, No. 17. pp. 4056-4062.
@article{5fd1119a9eeb47989e83f249421274f7,
title = "Di(4-methylphenyl)methano-C60 bis-adduct for efficient and stable organic photovoltaics with enhanced open-circuit voltage",
abstract = "A new class of fullerene bis-adducts-di(4-methylphenyl)methano-C 60 bis-adduct (DMPCBA), di(4-fluorophenyl)methano-C60 bis-adduct (DFPCBA), and diphenylmethano-C60 bis-adduct (DPCBA)-were rationally designed and easily synthesized. Compared to the lowest unoccupied molecular orbital (LUMO) energy level of PC61BM (-3.95 eV), the double functionalization effectively raises the LUMO energy levels of these fullerene materials to ca.-3.85 eV, regardless of the substituent groups (CH3-, F-, and H-) at the para-position of the phenyl rings. This phenomenon suggests that the plane of the phenyl groups is preferentially parallel to the fullerene surface, leading to poor orbital interactions with C60 and negligible electronic effect. Importantly, such geometry sterically protects and shields the core C60 structure from severe intermolecular aggregation, rendering it intrinsically soluble, morphologically amorphous, and thermally stable. The device based on the P3HT:DMPCBA blend exhibited an open-circuit voltage (Voc) of 0.87 V, a short-circuit current density (Jsc) of 9.05 mA/cm2, and a fill factor (FF) of 65.5{\%}, leading to a high power conversion efficiency (PCE) of 5.2{\%}, which is superior to that of the P3HT:PC61BM-based device. Most significantly, the amorphous nature of DMPCBA effectively suppresses the thermal-driven aggregation and thus stabilizes the morphology of the P3HT:DMPCBA blend. Consequently, the device retained 80{\%} of its original PCE value against thermal heating at 160 °C over 20 h.",
keywords = "C bis-adduct, morphological stability, open-circuit voltage, organic photovoltaics",
author = "Cheng, {Yen Ju} and Liao, {Ming Hung} and Chang, {Chih Yu} and Kao, {Wei Shun} and Wu, {Cheng En} and Hsu, {Chain Shu}",
year = "2011",
month = "9",
day = "13",
doi = "10.1021/cm201784w",
language = "English",
volume = "23",
pages = "4056--4062",
journal = "Chemistry of Materials",
issn = "0897-4756",
publisher = "American Chemical Society",
number = "17",

}

TY - JOUR

T1 - Di(4-methylphenyl)methano-C60 bis-adduct for efficient and stable organic photovoltaics with enhanced open-circuit voltage

AU - Cheng, Yen Ju

AU - Liao, Ming Hung

AU - Chang, Chih Yu

AU - Kao, Wei Shun

AU - Wu, Cheng En

AU - Hsu, Chain Shu

PY - 2011/9/13

Y1 - 2011/9/13

N2 - A new class of fullerene bis-adducts-di(4-methylphenyl)methano-C 60 bis-adduct (DMPCBA), di(4-fluorophenyl)methano-C60 bis-adduct (DFPCBA), and diphenylmethano-C60 bis-adduct (DPCBA)-were rationally designed and easily synthesized. Compared to the lowest unoccupied molecular orbital (LUMO) energy level of PC61BM (-3.95 eV), the double functionalization effectively raises the LUMO energy levels of these fullerene materials to ca.-3.85 eV, regardless of the substituent groups (CH3-, F-, and H-) at the para-position of the phenyl rings. This phenomenon suggests that the plane of the phenyl groups is preferentially parallel to the fullerene surface, leading to poor orbital interactions with C60 and negligible electronic effect. Importantly, such geometry sterically protects and shields the core C60 structure from severe intermolecular aggregation, rendering it intrinsically soluble, morphologically amorphous, and thermally stable. The device based on the P3HT:DMPCBA blend exhibited an open-circuit voltage (Voc) of 0.87 V, a short-circuit current density (Jsc) of 9.05 mA/cm2, and a fill factor (FF) of 65.5%, leading to a high power conversion efficiency (PCE) of 5.2%, which is superior to that of the P3HT:PC61BM-based device. Most significantly, the amorphous nature of DMPCBA effectively suppresses the thermal-driven aggregation and thus stabilizes the morphology of the P3HT:DMPCBA blend. Consequently, the device retained 80% of its original PCE value against thermal heating at 160 °C over 20 h.

AB - A new class of fullerene bis-adducts-di(4-methylphenyl)methano-C 60 bis-adduct (DMPCBA), di(4-fluorophenyl)methano-C60 bis-adduct (DFPCBA), and diphenylmethano-C60 bis-adduct (DPCBA)-were rationally designed and easily synthesized. Compared to the lowest unoccupied molecular orbital (LUMO) energy level of PC61BM (-3.95 eV), the double functionalization effectively raises the LUMO energy levels of these fullerene materials to ca.-3.85 eV, regardless of the substituent groups (CH3-, F-, and H-) at the para-position of the phenyl rings. This phenomenon suggests that the plane of the phenyl groups is preferentially parallel to the fullerene surface, leading to poor orbital interactions with C60 and negligible electronic effect. Importantly, such geometry sterically protects and shields the core C60 structure from severe intermolecular aggregation, rendering it intrinsically soluble, morphologically amorphous, and thermally stable. The device based on the P3HT:DMPCBA blend exhibited an open-circuit voltage (Voc) of 0.87 V, a short-circuit current density (Jsc) of 9.05 mA/cm2, and a fill factor (FF) of 65.5%, leading to a high power conversion efficiency (PCE) of 5.2%, which is superior to that of the P3HT:PC61BM-based device. Most significantly, the amorphous nature of DMPCBA effectively suppresses the thermal-driven aggregation and thus stabilizes the morphology of the P3HT:DMPCBA blend. Consequently, the device retained 80% of its original PCE value against thermal heating at 160 °C over 20 h.

KW - C bis-adduct

KW - morphological stability

KW - open-circuit voltage

KW - organic photovoltaics

UR - http://www.scopus.com/inward/record.url?scp=80052479467&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=80052479467&partnerID=8YFLogxK

U2 - 10.1021/cm201784w

DO - 10.1021/cm201784w

M3 - Article

VL - 23

SP - 4056

EP - 4062

JO - Chemistry of Materials

JF - Chemistry of Materials

SN - 0897-4756

IS - 17

ER -