Premium
The Role of Heteroatoms Leading to Hydrogen Bonds in View of Extended Chemical Stability of Organic Semiconductors
Author(s) -
Enengl Christina,
Enengl Sandra,
Havlicek Marek,
Stadler Philipp,
Glowacki Eric D.,
Scharber Markus C.,
White Matthew,
Hingerl Kurt,
Ehrenfreund Eitan,
Neugebauer Helmut,
Sariciftci Niyazi Serdar
Publication year - 2015
Publication title -
advanced functional materials
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 6.069
H-Index - 322
eISSN - 1616-3028
pISSN - 1616-301X
DOI - 10.1002/adfm.201503241
Subject(s) - pentacene , materials science , heteroatom , organic semiconductor , doping , chemical stability , semiconductor , organic electronics , nanotechnology , molecule , hydrogen bond , hydrogen , photochemistry , optoelectronics , organic chemistry , chemistry , ring (chemistry) , thin film transistor , physics , layer (electronics) , transistor , voltage , quantum mechanics
The major challenge in organic electronics concerns the stability of organic semiconductor materials which affects the operational lifetime of devices. Recent reports have shown that hydrogen‐bonded pigments of the indigoid family are air‐ and moisture resistant. The magenta pigment quinacridone, a hydrogen‐bonded molecule in the solid state with a pentacene like frame, is a perfect example for extraordinary chemical stability. Here, studies using in situ spectroscopic methods comparing quinacridone and pentacene are presented. A different spectral response of their radical cations is observed upon chemical doping. While in pentacene the barrier between doping and irreversible overoxidation is small, this stability toward overoxidation is increased by the heteroatomic structure, leading to hydrogen‐bonded quinacridone. This work provides insight into molecular design principles that may lead to next‐generation organic semiconductors with enhanced stability and performance.