Regioregular Asymmetric Diketopyrrolopyrrole Copolymers with Good Molecular Ordered Assembly Ability for High-performance Polymer Transistors

Qing-Qing Liu; Jia-Xin Yang; Man Zhao; Can Gao; Bo Guan; Huan-Li Dong

doi:10.1007/s10118-023-2918-2

Your Location：

Home >

Browse articles >

Regioregular Asymmetric Diketopyrrolopyrrole Copolymers with Good Molecular Ordered Assembly Ability for High-performance Polymer Transistors

RESEARCH ARTICLE | Updated：2023-07-18

- Regioregular Asymmetric Diketopyrrolopyrrole Copolymers with Good Molecular Ordered Assembly Ability for High-performance Polymer Transistors
- Chinese Journal of Polymer Science Vol. 41, Issue 8, Pages: 1215-1222(2023)
- Affiliations：
  
  a.Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
  b.School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, China
- Author bio：
  
  cangao@iccas.ac.cn (C.G.)
  guanbo@iccas.ac.cn (B.G.)
  dhl522@iccas.ac.cn (H.L.D.)
- Funds：
- DOI：10.1007/s10118-023-2918-2
  CLC： M
- Received：28 October 2022，
  
  Revised：2022-11-27，
  
  Accepted：01 December 2022，
  
  Online First：01 February 2023，
  
  Published：01 August 2023
- Accepted：
Scan QR Code
Liu, Q. Q.; Yang, J. X.; Zhao, M.; Gao, C.; Guan, B.; Dong, H. L. Regioregular asymmetric diketopyrrolopyrrole copolymers with good molecular ordered assembly ability for high-performance polymer transistors. Chinese J. Polym. Sci. 2023, 41, 1215–1222

Qing-Qing Liu, Jia-Xin Yang, Man Zhao, et al. Regioregular Asymmetric Diketopyrrolopyrrole Copolymers with Good Molecular Ordered Assembly Ability for High-performance Polymer Transistors[J]. Chinese Journal of Polymer Science, 2023, 41(8): 1215-1222.
Liu, Q. Q.; Yang, J. X.; Zhao, M.; Gao, C.; Guan, B.; Dong, H. L. Regioregular asymmetric diketopyrrolopyrrole copolymers with good molecular ordered assembly ability for high-performance polymer transistors. Chinese J. Polym. Sci. 2023, 41, 1215–1222 DOI： 10.1007/s10118-023-2918-2.

Qing-Qing Liu, Jia-Xin Yang, Man Zhao, et al. Regioregular Asymmetric Diketopyrrolopyrrole Copolymers with Good Molecular Ordered Assembly Ability for High-performance Polymer Transistors[J]. Chinese Journal of Polymer Science, 2023, 41(8): 1215-1222. DOI： 10.1007/s10118-023-2918-2.

摘要

Abstract

Introduction of asymmetric units into conjugated polymers is an important strategy to regulate the photophysical and electronic properties of polymers

as asymmetric units can not only regulate solubility and energy levels

but also molecular stacking and orientation

thus giving much higher optoelectronic properties. However

very few studies have been reported in this field. The semiconducting properties of conjugated polymers could be regulated through regioregularity adjustment. Here

we took the asymmetric thiophene/pyridine side group DPP as core and developed the regioregular monomer T-Py-DPP through three steps: alkyl chain introduction

tin monomer coupling and NBS double bromination. The T-Py-DPP monomer was polymerized into

reg

-PPyTDPP-2FBT with a head-to-head structure. The regioregularity of T-Py-DPP unit endowed

reg

-PPyTDPP-2FBT with backbone planarity

self-assembly orientation

network-like morphology and high crystallinity in films

thus the superior bipolar transport properties. The highest hole and electron mobilities of

reg

-PPyTDPP-2FBT were 0.93 and 0.57 cm

·V

−1

·s

−1

respectively

with 40% improvement relative to the regiorandom polymer.

关键词

Keywords

references

Luo,L.;Huang,W.;Yang,C.;Zhang,J.;Zhang,Q.Recentadvanceson π -conjugatedpolymersasactiveelementsinhighperformanceorganicfield-effecttransistors. Front. Phys. 2021 , 16 ,33500..

Yao,Z.F.;Li,Q.Y.;Wu,H.T.;Ding,Y.F.;Wang,Z.Y.;Lu,Y.;Wang,J.Y.;Pei,J.BuildingcrystalstructuresofconjugatedpolymersthroughX-raydiffractionandmolecularmodeling. SmartMat 2021 , 2 ,378−387..

Zhou,Y.;Zhang,W.;Yu,G.Recentstructuralevolutionoflactam-andimide-functionalizedpolymersappliedinorganicfield-effecttransistorsandorganicsolarcells. Chem. Sci. 2021 , 12 ,6844−6878..

Adachi,C.;Sandanayaka,A.S.D.TheleapfromOrganiclight-emittingdiodestoorganicsemiconductorlaserdiodes. CCS Chem. 2020 , 2 ,1203−1216..

He,M.N.;Zhao,Y.;Liu,Y.Q.;Wei,D.C.A3Dprintableself-healingcompositeconductivepolymerforsensitivetemperaturedetection. Chin. Chem. Lett. 2020 , 31 ,826−830..

Yang,Y.Multi-tiercomputingnetworksforintelligentIoT. Nat. Electron. 2019 , 2 ,4−5..

Ni,Z.j.;Dong,H.L.;Wang,H.L.;Ding,S.;Zou,Y.;Zhao,Q.;Zhen,Y.G.;Liu,F.;Jiang,L.;Hu.W.P.Quinoline-flankeddiketopyrrolopyrrolecopolymersbreakingthroughelectronmobilityover6cm 2 V −1 s −1 inflexiblethinfilmdevices. Adv. Mater. 2018 , 30 ,1704843..

Yang,J.;Wang,H.;Chen,J.;Huang,J.;Jiang,Y.;Zhang,J.;Shi,L.;Sun,Y.;Wei,Z.;Yu,G.;Guo,Y.;Wang,S.;Liu,Y.Bis-diketopyrrolopyrrolemoietyasapromisingbuildingblocktoenablebalancedambipolarpolymersforflexibletransistors. Adv. Mater. 2017 , 29 ,1606162..

Yi,Z.;Wang,S.;Liu,Y.Designofhigh-mobilitydiketopyrrolopyrrole- b based π -conjugatedcopolymersfororganicthin-filmtransistors. Adv. Mater. 2015 , 27 ,3589−3606..

Ma,J.;Tian,J.;Liu,Z.;Shi,D.;Zhang,X.;Zhang,G.;Zhang,D.Multi-stimuli-responsivefield-effecttransistorwithconjugatedpolymerentailingspiropyraninthesidechains. CCS Chem. 2020 , 2 ,632−641..

Xu,J.;Wang,S.H.;Wang,G.J.N.;Zhu,C.X.;Luo,S.C.;Jin,L.H.;Gu,X.D.;Chen,S.C.;Feig,V.R.;To,J.W.F.;Rondeau-Gagne,S.;Park,J.;Schroeder,B.C.;Lu,C.;Oh,J.Y.;Wang,Y.M.;Kim,Y.H.;Yan,H.;Sinclair,R.;Zhou,D.S.;Xue,G.;Murmann,B.;Linder,C.;Cai,W.;Tok,J.B.H.;Chung,J.W.;Bao,Z.N.Highlystretchablepolymersemiconductorfilmsthroughthenanoconfinementeffect. Science 2017 , 355 ,59−64..

Qin,Z.S.;Gao,H.K.;Dong,H.L.;Hu,W.P.Organiclight-emittingtransistorsenteringanewdevelopmentstage. Adv. Mater. 2021 , 33 ,2007149..

Huang,F;Bo,Z.S;Geng,Y.H.;Wang,X.H.;Wang,L.X.;Ma,Y.G.;Hou,J.H.;Hu,W.P.;Pei,J.;Dong,H.L.;Wang,S.;Li,Z;Shuai,Z.G.;Li,Y.F.;Cao,Y.Studyonoptoelectronicpolymers:anoverviewandoutlook. Acta Polymerica Sinica (inChinese) 2019 , 50 ,988−1046..

Zhao,R.Y.;Liu,J.;Wang,L.X.PolymeracceptorscontainingB◊Nunitsfororganicphotovoltaics. Acc. Chem. Res. 2020 , 53 ,1557−1567..

Yue,H.;Wang,Z.;Zhen,Y.Recentadvancesofself-healingelectronicmaterialsappliedinorganicfield-effecttransistors. ACS Omega 2022 , 7 ,18197−18205..

Miao,J.;Wang,Y.;Liu,J.;Wang,L.Organoboronmoleculesandpolymersfororganicsolarcellapplications. Chem. Soc. Rev. 2022 , 51 ,153−187..

Yao,Z.F.;Zheng,Y.Q.;Dou,J.H.;Lu,Y.;Ding,Y.F.;Ding,L.;Wang,J.Y.;Pei,J.Approachingcrystalstructureandhighelectronmobilityinconjugatedpolymercrystals. Adv. Mater. 2021 , 33 ,e2006794..

Yu,Z.D.;Lu,Y.;Wang,J.Y.;Pei,J.Conformationcontrolofconjugatedpolymers. Chemistry 2020 , 26 ,16194−16205..

Wu,Y.J.;Zhao,Y.;Liu,Y.Q.Towardefficientchargetransportofpolymer-basedorganicfield-effecttransistors:moleculardesign,processing,andfunctionalutilization. Acc. Chem. Res. 2021 , 2 ,1047−1058..

Wang,M.;Ford,M.;Phan,H.;Coughlin,J.;Nguyen,T.Q.;Bazan,G.C.Fluorinesubstitutioninfluenceonbenzo[2,1,3]thiadiazolebasedpolymersforfield-effecttransistorapplications. Chem. Commun. 2016 , 52 ,3207−3210..

Yu,Y.;Wu,Y.;Zhang,A.;Li,C.;Tang,Z.;Ma,W.;Wu,Y.;Li,W.Diketopyrrolopyrrolepolymerswiththienylandthiazolyllinkersforapplicationinfield-effecttransistorsandpolymersolarcells. ACS Appl. Mater. Interfaces 2016 , 8 ,30328−30335..

Hu,D.P.;Chen,M.;Yang,Y.H.;Li,H.Y.Textureinducedbymolecularweightdispersity:polymorphismwithinpoly(L-lacticacid)spherulites. Chinese J. Polym. Sci. 2020 , 38 ,1365−1373..

Qiu,G.G.;Ni,Z.J.;Wang,H.L.;Dong,H.L.;Zhang,J.Q.;Zhang,X.T.;Shu,Z.B.;Lu,K.;Zhen,Y.G.;Wei,Z.X.;Hu,W.P.Asymmetricthiophene/pyridineflankeddiketopyrrolopyrrolepolymersforhighperformancepolymerambipolarfield-effecttransistorsandsolarcells. J. Mater. Chem. C 2017 , 5 ,566−572..

Fan,B.;Li,M.;Zhang,D.;Zhong,W.;Ying,L.;Zeng,Z.;An,K.;Huang,Z.;Shi,L.;Bazan,G.C.;Huang,F.;Cao,Y.Tailoringregioisomericstructuresof π -conjugatedpolymerscontainingmonofluorinated π -bridgesforhighlyefficientpolymersolarcells. ACS Energy Lett. 2020 , 5 ,2087−2094..

Yen,H.C.;Lin,Y.C.;Chen,W.C.Modulationofthehydrophilicityonasymmetricsidechainsofisoindigo-basedpolymersforimprovingcarriermobility-stretchabilityproperties. Macromolecules 2021 , 54 ,1665−1676..

Ji,Y.;Xiao,C.;Wang,Q.;Zhang,J.;Li,C.;Wu,Y.;Wei,Z.;Zhan,X.;Hu,W.;Wang,Z.;Janssen,R.A.;Li,W.Asymmetricdiketopyrrolopyrroleconjugatedpolymersforfield-effecttransistorsandpolymersolarcellsprocessedfromanonchlorinatedsolvent. Adv. Mater. 2016 , 28 ,943−950..

Gao,W.;Zhang,M.;Liu,T.;Ming,R.;An,Q.;Wu,K.;Xie,D.;Luo,Z.;Zhong,C.;Liu,F.;Zhang,F.;Yan,H.;Yang,C.Asymmetricalladder-typedonor-inducedpolarsmallmoleculeacceptortopromotefillfactorsapproaching77%forhigh-performancenonfullerenepolymersolarcells. Adv. Mater. 2018 , 30 ,1800052..

Zhong,W.;Sun,S.;Ying,L.;Liu,F.;Lan,L.;Huang,F.;Cao,Y.High-performanceorganicfield-effecttransistorsfabricatedbasedonanovelternarypi-conjugatedcopolymer. ACS Appl. Mater. Interfaces 2017 , 9 ,7315−7321..

Cho,Y.;Park,S.;Jeong,S.;Yang,H.;Lee,B.;Lee,S.M.;Lee,B.H.;Yang,C.Regioregular,yetductileandamorphousindacenodithiophene-basedpolymerswithhigh-mobilityforstretchableplastictransistors. J. Mater. Chem. C 2021 , 9 ,9670−9682..

Huang,Y.;Zheng,N.;Wang,Z.;Ying,L.;Huang,F.;Cao,Y.Synthesisofregioregular π -conjugatedpolymersconsistingofalactammoiety via directheteroarylationpolymerization. Chem. Commun. 2017 , 53 ,1997−2000..

Leenaers,P.J.;vanEersel,H.;Li,J.;Wienk,M.M.;Janssen,R.A.J.InfluenceofregioregularityontheoptoelectronicpropertiesofconjugateddiketopyrrolopyrrolepolymerscomprisingasymmetricMonomers. Macromolecules 2020 , 53 ,7749−7758..

Zhong,H.;Li,C.Z.;Carpenter,J.;Ade,H.;Jen,A.K.Influenceofregio-andchemoselectivityonthepropertiesoffluoro-substitutedthienothiopheneandbenzodithiophenecopolymers. J. Am. Chem. Soc. 2015 , 137 ,7616−7619..

Kim,Y.;Cook,S.;Tuladhar,S.M.;Choulis,S.A.;Nelson,J.;Durrant,J.R.;Bradley,D.D.C.;Giles,M.;McCulloch,I.;Ha,C.S.;Ree,M.Astrongregioregularityeffectinself-organizingconjugatedpolymerfilmsandhigh-efficiencypolythiophene:fullerenesolarcells. Nat. Mater. 2006 , 5 ,197−203..

Sirringhaus,H.;Brown,P.J.;Friend,R.H.;Nielsen,M.M.;Bechgaard,K.;Langeveld-Voss,B.M.W.;Spiering,A.J.H.;Janssen,R.A.J.;Meijer,E.W.;Herwig,P.;deLeeuw,D.M.Two-dimensionalchargetransportinself-organized,high-mobilityconjugatedpolymers. Nature 1999 , 401 ,685−688..

Coughlin,J.E.;Zhugayevych,A.;Wang,M.;Bazan,G.C.;Tretiak,S.Chargedelocalizationcharacteristicsofregioregularhighmobilitypolymers. Chem. Sci. 2017 , 8 ,1146−1151..

Perez,L.A.;Zalar,P.;Ying,L.;Schmidt,K.;Toney,M.F.;Nguyen,T.Q.;Bazan,G.C.;Kramer,E.J.Effectofbackboneregioregularityonthestructureandorientationofadonor-acceptorsemiconductingcopolymer. Macromolecules 2014 , 47 ,1403−1410..

Yang,J.X.;Liu,Q.Q.;Hu,M.X.;Ding,S.;Liu,J.;Wang,Y.S.;Liu,D.;Gao,H.K.;Hu,W.P.;Dong,H.L.Well-balancedambipolardiketopyrrolopyrrole-basedcopolymersforOFETs,invertersandfrequencydoublers. Sci. China Chem. 2021 , 64 ,1410−1416..

Ding,S.;Ni,Z.J.;Hu,M.X.;Qiu,G.G.;Li,J.;Ye,J.;Zhang,X.T.;Liu,F.;Dong,H.L.;Hu,W.P.Anasymmetricfuran/thieno[3,2- b ]thiophenediketopyrrolopyrrolebuildingblockforannealing-freegreensolventprocessableorganicthin-filmtransistors. Macromol. Rapid Commun. 2018 , 39 ,1800225..

Aoshima,K.;Nomura,M.;Saeki,A.Regioregularityandelectrondeficiencycontrolofunsymmetricdiketopyrrolopyrrolecopolymersfororganicphotovoltaics. ACS Omega 2019 , 4 ,15645−15652..

Ying,L.;Hsu,B.B.;Zhan,H.;Welch,G.C.;Zalar,P.;Perez,L.A.;Kramer,E.J.;Nguyen,T.Q.;Heeger,A.J.;Wong,W.Y.;Bazan,G.C.Regioregularpyridal[2,1,3]thiadiazole π -conjugatedcopolymers. J. Am. Chem. Soc. 2011 , 133 ,18538−18541..

Wang,Z.Y.;DiVirgilio,L.;Yao,Z.F.;Yu,Z.D.;Wang,X.Y.;Zhou,Y.Y.;Li,Q.Y.;Lu,Y.;Zou,L.;Wang,H.I.;Wang,X.Y.;Wang,J.Y.;Pei,J.Correlatingchargetransportpropertiesofconjugatedpolymersinsolutionaggregatesandthin-filmaggregates. Angew. Chem. Int. Ed. 2021 , 60 ,20483−20488..

Rivnay,J.M.S.C.;Miller,C.E.;Salleo,A.;Toney,M.F.Quantitativedeterminationoforganicsemiconductormicrostructurefromthemoleculartodevicescale. Chem. Rev. 2012 , 112 ,5488−5519..

Ni,Z.J;Wang,H.L.;Zhao,Q.;Zhang,J.Q.;Wei,Z.X.;Dong,H.L.;Hu,W.P.Ambipolarconjugatedpolymerswithultrahighbalancedholeandelectronmobilityforprintedorganiccomplementarylogic via atwo-stepC-Hactivationstrategy. Adv. Mater. 2019 , 31 ,e1806010..

Views

256

Downloads

CSCD

Alert me when the article has been cited

Submit

Tools

Publicity Resources

Pyrimidoisoindigo-based Polymers for Ambipolar Charge Transport

Poly(3-hexylthio) thiophene Field-effect Transistor Device Performance: Impact of the Content of Hexylthio Side Chain on Backbone

Topology-regulated Co-assembly of Single Chain Polymer Nanoparticles and Block Copolymers into Hierarchical Micelle@Vesicle Composite Structures

Epoxy-functionalized Cyclohexane-based Ricinoleate Plasticizer: Synthesis, Performance Evaluation, and Plasticizing Mechanism

Sliding Dynamics of Ring Chain on a Rod-Coil Block Copolymer in Rotaxane

Related Author

Xiao-Bo Wan

Yun-Qi Liu

Jian Pei

Jie-Yu Wang

Zhi-Yuan Zhao

You-Bing Mu

Ze-Zhou Liang

Xiao-Yan Zhang

Related Institution

Key Laboratory of Flexible Optoelectronic Materials and Technology, Ministry of Education, School of Optoelectronic Materials & Technology, Jianghan University

Beijing National Laboratory for Molecular Sciences, the Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University

Institute of Chemistry Chinese Academy of Sciences

State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University

School of Electronic Information and Electrical Engineering, Shanghai Jiao Tong University

⁰