Organic and Organometallic Fluorinated Materials for Electronics and Optoelectronics: A Survey on Recent Research

Abstract

Conjugated organic polymers, small molecules, and transition metal organometallic complexes are used as active semiconducting materials in electronic and optoelectronic devices including organic solar cells (OSCs), organic field effect transistors (OFETS), organic light emitting diodes (OLEDs). While some of these technologies are mature and already available on the market, research is still very active in academic and industrial laboratories to gain better performances. Major drawbacks which still limit large industrial production of some of these devices are not only the non‐optimized performances, but also stability issues and cost. In fact, wide applicability of organic electronic technology largely relies on the development of efficient, durable and cost‐effective materials. Properties of molecular and polymeric semiconductors can be properly engineered and finely tuned by the design of the conjugated molecular structure and the selective introduction of various functional groups as substituents. Selective functionalization of the conjugated backbone with fluorine atoms and fluorinated substituents has been largely demonstrated to be an effective structural modification not only for tuning optoelectronic properties, but also to affect solid state organization and to improve stability. This review covers the most important classes of materials (conjugated polymers, small molecules, and organometallic complexes) reporting for each of these classes the applications in OSCs, OFETs, and OLEDs and highlighting the role of fluorine functionalization on the properties. The literature shows intriguing results that can be achieved by fluorine functionalization, and it also points out that this research field is still promising for future progress.

A General Synthetic Approach and Photophysical Properties of Regioselectively Fluorinated [5]‐ and [6]‐Helical Bispiroindenofluorenes

“…These properties predetermined interest in various kind of fluorinated compounds and their application in various fields of material science, namely as material for electronics and optoelectronics. [1,2] A considerable attention has been payed to fluorinated aromatic and poly-aromatic compounds (PAHs) including fluorinated helicenes and these endeavors have been recently nicely summarized. [3,4] It should be mentioned that attaching of fluorine atoms to specific position of the polyaromatic scaffold (pinpoint-fluorinated polycyclic aromatic hydrocarbons -F-PAHs) is often a synthetic challenge and requires special approaches.…”

Fluorinated Organic Porous Materials

“…3,4 Materials chemistry has also been exploring fluorination as a method of modulating chemical and thermal stability, as well as physical properties, in polymers and other classes of materials. 5,6 In this minireview, we will summarize the recent advances in the preparation and utilization of fluorinated porous materials. Our text will be divided into four sections, discussing the effects of fluorination on the structures and properties of (1) metal-organic frameworks (MOFs), (2) covalent organic frameworks (COFs) and porous organic polymers (POPs), (3) extrinsically porous molecular crystals (PMCs), and (4) intrinsically porous molecular cages.…”

Fluorination and chlorination effects on quinoxalineimides as an electron-deficient building block for n-channel organic semiconductors

“…[21][22][23] Therefore, uorination has received much attention in the elds of OFETs and OPVs. 24,25 As compared to uorinated p-conjugated materials, a limited number of reports exist on chlorinated materials because of the large size of the chlorine atom, which induces steric hindrance effects in the pconjugated backbone. 26 However, chlorine atoms possess attractive properties such as a greater electron density capacity and easier accessibility with a lower cost compared to uorine atoms.…”