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Solution-Processable Silicon Phthalocyanines in Electroluminescent and Photovoltaic Devices.

ABSTRACT: Phthalocyanines and their main group and metal complexes are important classes of organic semiconductor materials but are usually highly insoluble and so frequently need to be processed by vacuum deposition in devices. We report two highly soluble silicon phthalocyanine (SiPc) diester compounds and demonstrate their potential as organic semiconductor materials. Near-infrared (?(EL) = 698-709 nm) solution-processed organic light-emitting diodes (OLEDs) were fabricated and exhibited external quantum efficiencies (EQEs) of up to 1.4%. Binary bulk heterojunction solar cells employing P3HT or PTB7 as the donor and the SiPc as the acceptor provided power conversion efficiencies (PCE) of up to 2.7% under simulated solar illumination. Our results show that soluble SiPcs are promising materials for organic electronics.

SUBMITTER: Zysman-Colman E

PROVIDER: S-EPMC4832396 | biostudies-literature | 2016 Apr

REPOSITORIES: biostudies-literature

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Solution-Processable Silicon Phthalocyanines in Electroluminescent and Photovoltaic Devices.

Zysman-Colman Eli E Ghosh Sanjay S SS Xie Guohua G Varghese Shinto S Chowdhury Mithun M Sharma Nidhi N Cordes David B DB Slawin Alexandra M Z AM Samuel Ifor D W ID

ACS applied materials & interfaces 20160331 14

Phthalocyanines and their main group and metal complexes are important classes of organic semiconductor materials but are usually highly insoluble and so frequently need to be processed by vacuum deposition in devices. We report two highly soluble silicon phthalocyanine (SiPc) diester compounds and demonstrate their potential as organic semiconductor materials. Near-infrared (λ(EL) = 698-709 nm) solution-processed organic light-emitting diodes (OLEDs) were fabricated and exhibited external quant ...[more]

PMID: 26990151

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Project description:Through the incorporation of a thiophene functionality, a novel solution-processable small organic chromophore was designed, synthesized and characterized for application in bulk-heterojunction solar cells. The new chromophore, (2Z,2'Z)-2,2'-(1,4-phenylene)bis(3-(5-(4-(diphenylamino)phenyl)thiophen-2-yl)acrylonitrile) (coded as AS2), was based on a donor-acceptor-donor (D-A-D) module where a simple triphenylamine unit served as an electron donor, 1,4-phenylenediacetonitrile as an electron acceptor, and a thiophene ring as the π-bridge embedded between the donor and acceptor functionalities. AS2 was isolated as brick-red, needle-shaped crystals, and was fully characterized by ¹H- and (13)C-NMR, IR, mass spectrometry and single crystal X-ray diffraction. The optoelectronic and photovoltaic properties of AS2 were compared with those of a structural analogue, (2Z,2'Z)-2,2'-(1,4-phenylene)bis(3-(4-(diphenylamino)phenyl)-acrylonitrile) (AS1). Benefiting from the covalent thiophene bridges, compared to AS1 thin solid film, the AS2 film showed: (1) an enhancement of light-harvesting ability by 20%; (2) an increase in wavelength of the longest wavelength absorption maximum (497 nm vs. 470 nm) and (3) a narrower optical band-gap (1.93 eV vs. 2.17 eV). Studies on the photovoltaic properties revealed that the best AS2-[6,6]-phenyl-C61-butyric acid methyl ester (PC61BM)-based device showed an impressive enhanced power conversion efficiency of 4.10%, an approx. 3-fold increase with respect to the efficiency of the best AS1-based device (1.23%). These results clearly indicated that embodiment of thiophene functionality extended the molecular conjugation, thus enhancing the light-harvesting ability and short-circuit current density, while further improving the bulk-heterojunction device performance. To our knowledge, AS2 is the first example in the literature where a thiophene unit has been used in conjunction with a 1,4-phenylenediacetonitrile accepting functionality to extend the π-conjugation in a given D-A-D motif for bulk-heterojunction solar cell applications.

Dataset Information

Solution-Processable Silicon Phthalocyanines in Electroluminescent and Photovoltaic Devices.

Publications

Solution-Processable Silicon Phthalocyanines in Electroluminescent and Photovoltaic Devices.

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