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구동건,이다빈,노주란,이용현,장서현,남인호,신태주,박주현 한국고분자학회 2021 Macromolecular Research Vol.29 No.1
In this study, intermolecular interactions were investigated for increasing the charge carrier mobility of organic field-effect transistors (OFETs) based on a conjugated polymer. A diketopyrrolopyrrole (DPP)-based conjugated polymer widely used in OFETs, i.e., poly[2,5-(2-octyldodecyl)-3,6-diketopyrrolopyrrole-alt-5,5-(2,5-di(thien-2- yl)thieno[3,2-b]thiophene)] (PDPP-DTT), was assembled using 2-bromobenzaldehyde (2-BBA) and used as an active layer for OFETs. Morphological characterization and analysis for non-covalent intermolecular interactions suggested that the halogen bonding between the bromide of 2-BBA and electron-donor group of PDPP-DTT and the association between the electron-acceptor group in 2-BBA and sulfur of PDPP-DTT improved the hole transfer in the PDPP-DTT-based OFETs. The intermolecular interactions resulting from the addition of 2-BBA contributed to the two-fold enhancement of the hole mobility, two-order increase in magnitude of the current on/off ratio, and 50% decrease in the threshold voltage of the OFETs based on PDPP-DPP.
Hong, Han Na,Kim, Hyung Jong,Kim, Aesun,Choi, Suna,Kim, Young Un,Cho, Min Ju,Choi, Dong Hoon Elsevier Sequoia 2018 Synthetic metals Vol.236 No.-
<P><B>Abstract</B></P> <P>The <I>p</I>- and <I>n</I>-type semiconducting characteristics of four conjugated polymers, P(DPPBT), P(DPPBTz), P(TzDPPBT), and P(TzDPPBTz) with molecular energy levels that were systematically varied in a cascade manner, was investigated. The four polymers were synthesized using 3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-<I>c</I>]pyrrole-1,4(2<I>H</I>,5<I>H</I>)-dione or 3,6-bis(5-bromothiazol-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo [3,4-<I>c</I>]pyrrole-1,4(2<I>H</I>,5<I>H</I>)-dione monomers coupled with bithiophene or bithiazole monomers. By replacing the electron-rich thiophene with electron-deficient thiazole, the energy levels of the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) were significantly lowered. Thin film transistors (TFTs) based on the four polymers were investigated to observe the effect of the polymer energy levels. The results demonstrate that DPP-based polymers have the potential to exhibit <I>p</I>-type or <I>n</I>-type semiconducting properties based on the number of thiazole units incorporated into the conjugated polymer structure.</P> <P><B>Highlights</B></P> <P> <UL> <LI> DPP-based copolymers were synthesized for organic thin film transistors. </LI> <LI> Electronic properties of the <I>p</I>-type and <I>n</I>-type semiconducting polymers are systematically investigated. </LI> <LI> P(TzDPPBTz) displayed <I>n</I>-type semiconducting characteristics under ambient conditions. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>The electronic properties of a diketopyrrolopyrrole-based copolymer were easily tuned by employing thiophene or thiazole units in the conjugated polymer backbone. P(TzDPPBTz) showed unique <I>n</I>-type semiconducting characteristics without passivation, under ambient conditions.</P> <P>[DISPLAY OMISSION]</P>
송인호,김기현,박선희,유호정,강현범,김범준,오준학 한국공업화학회 2015 한국공업화학회 연구논문 초록집 Vol.2015 No.1
Tuning crystalline properties of polymers has been proven to boost electrical performance in conjugated polymers. Herein, a new series of conjugated random terpolymers was synthesized from an electron-deficient diketopyrrolopyrrole-based unit in conjugation with two electronrich selenophene and thiophene species. The crystallinity of the terpolymers could be systematically controlled by tuning the ratio between the two species. An increase in selenophene content induced a remarkable enhancement in crystallinity of the terpolymers. These changes in the crystalline properties of polymers had a dramatic effect on the performances of organic field-effect transistors. The investigation of control of crystallinity via terpolymer approach in this work can provide new insight into the molecular design of high-performance polymer semiconductors.
김재윤,김영운,김현종,엄현아,신지철,조민주,최동훈 한국고분자학회 2016 Macromolecular Research Vol.24 No.11
The new diketopyrrolopyrrole-based copolymer, referred to as PDPPBDTE, bearing linear alkyl ester groups, was synthesized with the objective of improving the miscibility between the donor polymer and [6,6]-phenyl C71 butyric acid methyl ester (PC71BM). PDPPBDTA bearing ethylhexyl side-chains was also synthesized as a control polymer. The PDPPBDTE:PC71BM blend film showed a relatively small crystalline domain size compared to the PDPPBDTA:PC71BM blend film. A polymer solar cell fabricated with PDPPBDTE and PC71BM exhibited twofold higher power conversion efficiency than that employing PDPPBDTA.
송인호,오준학,유호정,김범준,강현범,박선희,김기현 한국공업화학회 2015 한국공업화학회 연구논문 초록집 Vol.2015 No.0
Tuning crystalline properties of polymers has been proven to boost electrical performance in conjugated polymers. Herein, a new series of conjugated random terpolymers was synthesized from an electron-deficient diketopyrrolopyrrole-based unit in conjugation with two electronrich selenophene and thiophene species. The crystallinity of the terpolymers could be systematically controlled by tuning the ratio between the two species. An increase in selenophene content induced a remarkable enhancement in crystallinity of the terpolymers. These changes in the crystalline properties of polymers had a dramatic effect on the performances of organic field-effect transistors. The investigation of control of crystallinity via terpolymer approach in this work can provide new insight into the molecular design of high-performance polymer semiconductors.
Shin, Jicheol,Park, Gi Eun,Lee, Dae Hee,Um, Hyun Ah,Lee, Tae Wan,Cho, Min Ju,Choi, Dong Hoon American Chemical Society 2015 ACS APPLIED MATERIALS & INTERFACES Vol.7 No.5
<P>New thienothiophene-flanked diketopyrrolopyrrole and thiophene-containing π-extended conjugated polymers with various branched alkyl side-chains were successfully synthesized. 2-Octyldodecyl, 2-decyltetradecyl, 2-tetradecylhexadecyl, 2-hexadecyloctadecyl, and 2-octadecyldocosyl groups were selected as the side-chain moieties and were anchored to the N-positions of the thienothiophene-flanked diketopyrrolopyrrole unit. All five polymers were found to be soluble owing to the bulkiness of the side chains. The thin-film transistor based on the 2-tetradecylhexadecyl-substituted polymer showed the highest hole mobility of 1.92 cm<SUP>2</SUP> V<SUP>–1</SUP> s<SUP>–1</SUP> due to it having the smallest π–π stacking distance between the polymer chains, which was determined by grazing incidence X-ray diffraction. Bulk heterojunction polymer solar cells incorporating [6,6]-phenyl-C71-butyric acid methyl ester as the n-type molecule and the additive 1,8-diiodooctane (1 vol %) were also constructed from the synthesized polymers without thermal annealing; the device containing the 2-octyldodecyl-substituted polymer exhibited the highest power conversion efficiency of 5.8%. Although all the polymers showed similar physical properties, their device performance was clearly influenced by the sizes of the branched alkyl side-chain groups.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/aamick/2015/aamick.2015.7.issue-5/am508026s/production/images/medium/am-2014-08026s_0009.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/am508026s'>ACS Electronic Supporting Info</A></P>
Kim, Ji Ho,Lee, Dae Hee,Yang, Da Seul,Heo, Dong Uk,Kim, Kyung Hwan,Shin, Jicheol,Kim, Hyun‐,Ji,Baek, Kyung‐,Youl,Lee, Kwangyeol,Baik, Hionsuck,Cho, Min Ju,Choi, Dong Hoon WILEY‐VCH Verlag 2013 ADVANCED MATERIALS Vol.25 No.30
<P><B>The first demonstration of polymer nanowire (PNW) crystals</B> based on a diketopyrrolopyrrole‐based copolymer (i.e., PDTTDPP), and their application to field‐effect transistors (FETs) is reported. Remarkably, transmission electron microscopy and selected area electron diffraction analyses of the PNW reveal its single‐crystalline (SC) nature. FETs fabricated of a SC PNW exhibit a maximal charge carrier mobility of ≈7.00 cm<SUP>2</SUP> V<SUP>−1</SUP> s<SUP>−1</SUP>, which is almost one order of magnitude higher than that of the thin‐film transistors made of the same polymer (PDTTDPP).</P>