The Rise of Silicon Phthalocyanine: From Organic Photovoltaics to Organic Thin Film Transistors

Abstract

Silicon phthalocyanines are emerging n-type semiconductors for use in organic photovoltaics (OPVs) and organic thin-film transistors (OTFTs). Their low synthetic complexity paired with their versatile axial group facilitates the fine-tuning of their chemical properties, solution properties and processing characteristics without significantly affecting their frontier orbital levels or their absorption properties. The crystal engineering and film forming characteristics of silicon phthalocyanine semiconductors can be tuned through appropriate axial group functionalization, therefore facilitating their integration into both OTFTs and OPVs by solution processing or vapor deposition. This Spotlight on Applications will discuss recent advances in the integration of this exciting class of phthalocyanine into OTFTs and OPVs and highlights their promising future.

Chloro aluminum phthalocyanine-based organic thin-film transistors as cannabinoid sensors: engineering the thin film response

“…23,24 MPcs are thermally and chemically stable, inexpensive to manufacture on the ton scale with facile metal substitution providing opportunities to tune molecular interactions for integration into OTFT sensors. 6,21,[25][26][27][28][29][30] While many MPcs are insoluble 2 or sparingly soluble in organic solvents, they can be modified with solubilizing groups making them potentially compatible with low-cost solution processing techniques. Previously, we demonstrated copper phthalocyanine (CuPc) OTFT sensors for ratiometric detection and differentiation of cannabinoids.…”

Thermodynamic Property–Performance Relationships in Silicon Phthalocyanine-Based Organic Photovoltaics

“…Metal phthalocyanines (MPcs) are commercial pigments, produced on the multi-ton scale annually, that have been explored in organic electronic applications for over 50 years. In fact, the first ever heterojunction OPV, developed by Tang in 1986, utilized copper phthalocyanine (CuPc) in combination with a perylene derivative as the donor and acceptor, respectively. , Most widely studied MPcs exhibit p-type characteristics, where they preferentially transport holes over electrons. , Alternatively, silicon phthalocyanines (R 2 -SiPcs) are tetravalent MPcs displaying impressive n-type characteristics, , with demonstrated applications in light-emitting diodes (OLEDs), − thin-film transistors (OTFTs), ,,− and OPVs. ,− R 2 -SiPcs have additional chemical versatility compared to most MPcs, with two axial sites available for chemical modification, facilitating tuning of electronic, chemical, and physical properties, ultimately improving the prospects for device optimization through fine-tuning such properties. ,− …”

Correlating Morphology, Molecular Orientation, and Transistor Performance of Bis(pentafluorophenoxy)silicon Phthalocyanine Using Scanning Transmission X-ray Microscopy

“…47−50 SiPcs have recently attracted interest in the field of organic electronics due to their ability to efficiently transport electrons. 51 Our group has reported the synthesis and integration of various SiPcs into OPV devices and OTFT devices. 32,50,52−58 When studying thin films of SiPcs, we often observe significant changes in morphology as a result of molecular structure and processing conditions.…”

“…In this study, we report the use of STXM to investigate the impact of processing conditions on thin films of low-symmetry bis­(pentafluorophenoxy) silicon phthalocyanine (F 10 -SiPc) (Figure b). Silicon phthalocyanines (SiPc) are highly conjugated macrocycles chelating a silicon atom that can easily be functionalized through axial substitutions. − SiPcs have recently attracted interest in the field of organic electronics due to their ability to efficiently transport electrons . Our group has reported the synthesis and integration of various SiPcs into OPV devices and OTFT devices. ,,− When studying thin films of SiPcs, we often observe significant changes in morphology as a result of molecular structure and processing conditions.…”