Self-assembly and charge carrier transport of sublimated dialkyl substituted quinacridones

Tomasz Marszałek , Izabela Krygier , Adam Proń , Zbigniew Wróbel , Paul M.W. Blom , Irena Kulszewicz-Bajer , Wojciech Pisula

Abstract

Quinacridone, an industrial pigment, has recently shown a high charge carriers mobility in field-effect transistors. In search for new cheap organic semiconductors of improved vacuum processability we have synthesized three dialkyl derivatives of quinacridone, namely N,N'-dialkylquinacridones (alkyl = butyl, octyl, dodecyl), abbreviated as QA-C4, QA-C8 and QA-C12. The alkylation of quinacridone results in a significant decrease of its melting temperature which drops from 390 degrees C for quinacridone to 261 degrees C, 177 degrees C and 134 degrees C for QA-C4, QA-C8 and QA-C12, respectively, while retaining the onset of thermal decomposition above 390 degrees C. The elimination of the hydrogen bonding network between the carbonyl groups and amine hydrogens through alkylation not only lowers the melting temperature, but also induces supramolecular ordering in contrast to unsubstituted quinacridone. Detailed morphological and structural investigations of the vacuum deposited thin films have revealed that the length of the alkyl substituent is crucial for the molecular self-organization. Compound QA-C4 forms poorly ordered films, whereas QA-C8 and QA-C12 grow into a spherulitic dense morphology with increasing domain size at higher deposition temperatures. The more pronounced morphology is related to the lower melting point of the compounds and strong molecular diffusion during deposition. The poorly ordered films of QA-C4 do not show any field-effect response, what is consistent with previous reports. In contrast, transistors with QA-C8 or QA-C12 as active layers exhibit hole transport. Optimization of the deposition temperature, in which nucleation and crystal growth are properly balanced, resulted in OA-C8-based transistors with a hole mobility of 0.3 cm(2)/V, i.e. higher than in devices with unsubstituted quinacridone.
Author Tomasz Marszałek - [Max Planck Institute for Polymer Research]
Tomasz Marszałek,,
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, Izabela Krygier - [Max Planck Institute for Polymer Research]
Izabela Krygier,,
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, Adam Proń (FC / CPCT)
Adam Proń,,
- Chair Of Polymer Chemistry And Technology
, Zbigniew Wróbel - [Institute of Organic Chemistry of the Polish Academy of Sciences]
Zbigniew Wróbel,,
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, Paul M.W. Blom - [Max Planck Institute for Polymer Research]
Paul M.W. Blom,,
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, Irena Kulszewicz-Bajer (FC / CPCT)
Irena Kulszewicz-Bajer,,
- Chair Of Polymer Chemistry And Technology
, Wojciech Pisula - [Max Planck Institute for Polymer Research]
Wojciech Pisula,,
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Journal seriesOrganic Electronics, ISSN 1566-1199, (A 35 pkt)
Issue year2019
Vol65
Pages127-134
Publication size in sheets0.5
Keywords in EnglishOrganic field-effect transistor; Self-assembly; Thin film morphology; Quinacridone; Sublimation
ASJC Classification2208 Electrical and Electronic Engineering; 2505 Materials Chemistry; 3104 Condensed Matter Physics; 1600 General Chemistry; 2502 Biomaterials; 2504 Electronic, Optical and Magnetic Materials
DOIDOI:10.1016/j.orgel.2018.11.004
Languageen angielski
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wdpb_publikacje_pliki_plik_publikacja_3607_org.pdf 2.34 MB
Score (nominal)35
ScoreMinisterial score = 35.0, 30-04-2019, ArticleFromJournal
Ministerial score (2013-2016) = 40.0, 11-03-2019, ArticleFromJournal
Publication indicators Scopus Citations = 0; WoS Citations = 0; Scopus SNIP (Source Normalised Impact per Paper): 2017 = 0.884; WoS Impact Factor: 2017 = 3.68 (2) - 2017=3.243 (5)
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