Thiazoloisoindigo-based Polymer Semiconductors: Synthesis, Structure-Property Relationship, Charge Carrier Polarity, and Field-Effect Transistor Performance

Bo-Wen Li; Miao Xiong; Mei-Hua Liu; Zhi-Gao Li; Long Sang; Zi-Han Xiong; Biao Xiao; Jian Pei; Xiao-Bo Wan

doi:10.1007/s10118-023-3043-y

Your Location：

Home >

Browse articles >

Thiazoloisoindigo-based Polymer Semiconductors: Synthesis, Structure-Property Relationship, Charge Carrier Polarity, and Field-Effect Transistor Performance

RESEARCH ARTICLE | Updated：2023-12-26

- Thiazoloisoindigo-based Polymer Semiconductors: Synthesis, Structure-Property Relationship, Charge Carrier Polarity, and Field-Effect Transistor Performance
- Chinese Journal of Polymer Science Vol. 42, Issue 1, Pages: 24-31(2024)
- Affiliations：
  
  a.Key Laboratory of Optoelectronic Chemical Materials and Devices, Ministry of Education, School of Optoelectronic Materials & Technology, Jianghan University, Wuhan 430056, China
  b.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, Beijing 100871, China
- Author bio：
  
  libw@jhun.edu.cn (B.W.L.)
  wanxb@jhun.edu.cn (X.B.W.)
- Funds：
- DOI：10.1007/s10118-023-3043-y
  CLC：
- Received：24 June 2023，
  
  Revised：2023-7-23，
  
  Accepted：16 August 2023，
  
  Online First：20 September 2023，
  
  Published：01 January 2024
- Accepted：
Scan QR Code
Li, B. W.; Xiong, M.; Liu, M. H.; Li, Z. G.; Sang, L.; Xiong, Z. H.; Xiao, B.; Pei, J.; Wan, X. B. Thiazoloisoindigo-based polymer semiconductors: synthesis, structure-property relationship, charge carrier polarity, and field-effect transistor performance. Chinese J. Polym. Sci. 2024, 42, 24–31

Bo-Wen Li, Miao Xiong, Mei-Hua Liu, et al. Thiazoloisoindigo-based Polymer Semiconductors: Synthesis, Structure-Property Relationship, Charge Carrier Polarity, and Field-Effect Transistor Performance[J]. Chinese Journal of Polymer Science, 2024, 42(1): 24-31.
Li, B. W.; Xiong, M.; Liu, M. H.; Li, Z. G.; Sang, L.; Xiong, Z. H.; Xiao, B.; Pei, J.; Wan, X. B. Thiazoloisoindigo-based polymer semiconductors: synthesis, structure-property relationship, charge carrier polarity, and field-effect transistor performance. Chinese J. Polym. Sci. 2024, 42, 24–31 DOI： 10.1007/s10118-023-3043-y.

Bo-Wen Li, Miao Xiong, Mei-Hua Liu, et al. Thiazoloisoindigo-based Polymer Semiconductors: Synthesis, Structure-Property Relationship, Charge Carrier Polarity, and Field-Effect Transistor Performance[J]. Chinese Journal of Polymer Science, 2024, 42(1): 24-31. DOI： 10.1007/s10118-023-3043-y.

摘要

Two new polymers based on based on thiophene-flanked thiazoloisoindigo (Th-TzII) were synthesized by simply copolymerizing it with bisthiophene and bisthiazole

and the charge carrier polarity can be adjusted between unipolar hole transport and bipolar transport

which provides an effective molecular design strategy for further optimization of polymer OFET performance.

Abstract

Developing new polymeric semiconductors with excellent device performance is essential for organic electronics. Herein

we synthesized two new thiazoloisoindigo (TzII)-based polymers

namely

P(TzII-dTh-dTh) and P(TzII-dTh-dTz)

by copolymerizing thiophene-flanked TzII with bithiophene and bithiazole

respectively. Owing to the more electron-deficient nature of bithiazole than bithiophene

P(TzII-dTh-dTz) possesses deeper LUMO/HOMO levels of −3.45/−5.47 eV than P(TzII-dTh-dTh) (−3.34/−5.32 eV). The organic field-effect transistor (OFET) devices based on P(TzII-dTh-dTh) exhibited p-type behaviors with an average hole mobility value as high as 1.43 cm

·V

−1

·s

−1

while P(TzII-dTh-dTz) showed typical ambipolar characteristics with average hole and electron mobilities of 0.38 and 0.56 cm

·V

−1

·s

−1

. In addition

we compared the performances of both polymers with other TzII-based polymers reported in our previous work

and showed that the charge carrier polarity can be manipulated by adjusting the number of the thiophene units between the acceptor unit. As the increase of the number of thiophene rings

charge carrier polarity shifts from electron-dominated ambipolar transport to hole-dominated ambipolar transport and then to unipolar hole transport in OFETs

which provides an effective molecular design strategy for further optimization of polymer OFET performance.

关键词

Keywords

references

Huang,J.;Yu,G.Structuralengineeringinpolymersemiconductorswitharomaticn-heterocycles. Chem. Mater. 2021 , 33 ,1513−1539..

Sun,H.;Guo,X.;Facchetti,A.High-performancen-typepolymersemiconductors:applications,recentdevelopment,andchallenges. Chem 2020 , 6 ,1310−1326..

Zhang,Y.;Wang,Y.;Gao,C.;Ni,Z.;Zhang,X.;Hu,W.;Dong,H.Recentadvancesinn-typeandambipolarorganicsemiconductorsandtheirmulti-functionalapplications. Chem. Soc. Rev. 2023 , 52 ,1331−1381..

Wei,X.;Zhang,W.;Yu,G.Semiconductingpolymersbasedonisoindigoanditsderivatives:synthetictactics,structuralmodifications,andapplications. Adv. Funct. Mater. 2021 , 31 ,2010979..

Liu,Q.;Bottle,S.E.;Sonar,P.Developmentsofdiketopyrrolopyrrole-dye-basedorganicsemiconductorsforawiderangeofapplicationsinelectronics. Adv. Mater. 2020 , 32 ,1903882..

Li,B.;Zou,X.;Xiong,M.;Li,Q.;Kang,X.;Mu,Y.;Wang,J.;Pei,J.;Yang,C.;Lan,Z.;Wan,X.Thiazoloisoindigo-basedambipolarpolymersforexcellentbalancedholeandelectronmobility. Mater. Chem. Front. 2022 , 6 ,3369−3381..

Fusco,S.;Barra,M.;Gontrani,L.;Bonomo,M.;Chianese,F.;Galliano,S.;Centore,R.;Cassinese,A.;Carbone,M.;Carella,A.Novelthienyldppderivativesfunctionalizedwithterminalelectron-acceptorgroups:synthesis,opticalpropertiesandOFETperformance. Chem. Eur. J. 2022 , 28 ,e202104552..

Ocheje,M.U.;Comí,M.;Yang,R.;Chen,Z.;Liu,Y.;Yousefi,N.;Al-Hashimi,M.;Rondeau-Gagné,S.Molecularengineeringofbenzothiadiazole-basedpolymers:balancingchargetransportandstretchabilityinorganicfield-effecttransistors. J. Mater. Chem. C 2022 , 10 ,4236−4246..

Shi,Y.;Guo,H.;Qin,M.;Wang,Y.;Zhao,J.;Sun,H.;Wang,H.;Wang,Y.;Zhou,X.;Facchetti,A.;Lu,X.;Zhou,M.;Guo,X.Imide-functionalizedthiazole-basedpolymersemiconductors:synthesis,structure-propertycorrelations,chargecarrierpolarity,andthin-filmtransistorperformance. Chem. Mater. 2018 , 30 ,7988−8001..

Kim,M.;Ryu,S.U.;Park,S.A.;Choi,K.;Kim,T.;Chung,D.;Park,T.Donor-acceptor-conjugatedpolymerforhigh-performanceorganicfield-effecttransistors:aprogressreport. Adv. Funct. Mater. 2019 , 30 ,1904545..

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

Zou,X.;Cui,S.;Li,J.;Wei,X.;Zheng,M.Diketopyrrolopyrrolebasedorganicsemiconductormaterialsforfield-effecttransistors. Front. Chem. 2021 , 9 ,671294..

Cheon,H.J.;An,T.K.;Kim,Y.H.Diketopyrrolopyrrole(DPP)-basedpolymersandtheirorganicfield-effecttransistorapplications:areview. Macromol. Res. 2022 , 30 ,71−84..

Wang,X.;Liu,S.;Ren,C.;Cao,L.;Zhang,W.;Wu,T.Synthesis,characterization,andfield-effecttransistorpropertiesofnaphthalenediimide-basedconjugatedpolymerswithfluorine-containingbranchedsidechains. Macromolecules 2022 , 55 ,6415−6425..

Ye,G.;Liu,J.;Qiu,X.;Stäter,S.;Qiu,L.;Liu,Y.;Yang,X.;Hildner,R.;Koster,L.J.A.;Chiechi,R.C.Controllingn-typemoleculardoping via regiochemistryandpolarityofpendantgroupsonlowbandgapdonor-acceptorcopolymers. Macromolecules 2021 , 54 ,3886−3896..

Zhang,L.;Wang,Z.;Duan,C.;Wang,Z.;Deng,Y.;Xu,J.;Huang,F.;Cao,Y.Conjugatedpolymersbasedonthiazoleflankednaphthalenediimideforunipolarn-typeorganicfield-effecttransistors. Chem. Mater. 2018 , 30 ,8343−8351..

Feng,K.;Guo,H.;Wang,J.;Shi,Y.;Wu,Z.;Su,M.;Zhang,X.;Son,J.H.;Woo,H.Y.;Guo,X.Cyano-functionalizedbithiopheneimide-basedn-typepolymersemiconductors:synthesis,structureвауpropertycorrelations,andthermoelectricperformance. J. Am. Chem. Soc. 2021 , 143 ,1539−1552..

Comí,M.;Ocheje,M.U.;Attar,S.;Mu,A.U.;Philips,B.K.;Kalin,A.J.;Kakosimos,K.E.;Fang,L.;Rondeau-gagné,S.;al-hashimi,M.synthesisandphotocyclizationofconjugateddiselenophenepyrrole-2,5-dionebasedmonomersforoptoelectronics. Macromolecules 2021, 54 ,665-672..

Kim,M.;Park,W.-T.;Park,S.A.;Park,C.W.;Ryu,S.U.;Lee,D.H.;Noh,Y.-Y.;Park,T.Controllingambipolarchargetransportinisoindigo-basedconjugatedpolymersbyalteringfluorinesubstitutionpositionforhigh-performanceorganicfield-effecttransistors. Adv. Funct. Mater. 2019 , 29 ,1805994..

Wakioka,M.;Yamashita,N.;Mori,H.;Murdey,R.;Shimoaka,T.;Shioya,N.;Wakamiya,A.;Nishihara,Y.;Hasegawa,T.;Ozawa,F.Formationof trans -poly(thienylenevinylene)thinfilmsbysolid-statethermalisomerization. Chem. Mater. 2021 , 33 ,5631−5638..

Cho,H.J.;Kang,S.J.;Lee,S.M.;Jeong,M.;Kim,G.;Noh,Y.Y.;Yang,C.Influenceofsimultaneoustuningofmolecularweightsandalkylsubstituentsofpoly(thienoisoindigo- alt -naphthalene)sonmorphologyandchangetransportproperties. ACS Appl. Mater. Interfaces 2017 , 9 ,30755−30763..

Raj,M.R.;Kim,Y.;Park,C.E.;An,T.K.;Park,T.Effectofthelengthofasymmetricbranchedsidechainonchargetransportinthienoisoindigo-basedpolymerfield-effecttransistors. Org. Electron. 2019 , 65 ,251−258..

Li,C.;Un,H.I.;Peng,J.;Cai,M.;Wang,X.;Wang,J.;Lan,Z.;Pei,J.;Wan,X.Thiazoloisoindigo:abuildingblockthatmergesthemeritsofthienoisoindigoanddiazaisoindigoforconjugatedpolymers. Chem. Eur. J. 2018 , 24 ,9807−9811..

Li,C.;Zhang,H.;Mirie,S.;Peng,J.;Cai,M.;Wang,X.;Lan,Z.;Wan,X.Anewapproachtothiazoloisoindigoandderivativesusingalithiumtetramethylpiperidinepromotedcyclizationtothiazoloisatin. Org. Chem. Front. 2018 , 5 ,442−446..

Lv,S.Y.;Li,Q.Y.;Li,B.W.;Wang,J.Y.;Mu,Y.B.;Li,L.;Pei,J.;Wan,X.B.Thiazole-flankedthiazoloisoindigoasamonomerforbalancedambipolarpolymericfield-effecttransistors. Chinese J. Polym. Sci. 2022 , 40 ,1131−1140..

Li,C.C.;Xiong,M.;Peng,J.W.;Wang,J.Y.;Zhang,H.R.;Mu,Y.B.;Pei,J.;Wan,X.B.Finelytunedelectron/holetransportpreferenceofthiazoloisoindigo-basedconjugatedpolymersbyincorporationofheavychalcogenophenes. Chinese J. Polym. Sci. 2021 , 39 ,838−848..

Li,B.;Zou,X.;Li,Q.;Sang,H.;Mu,Y.;Wang,J.;Pei,J.;Yang,C.;Li,L.;Wan,X.Alternatingcopolymersofthiophene-flankedthiazoloisoindigoandthiophene-flankedbenzothiadiazoleforhigh-performanceambipolarorganicfield-effecttransistors. Org. Electron. 2023 , 113 ,106708..

Eckstein,B.J.;Melkonyan,F.S.;Wang,G.;Wang,B.;Manley,E.F.;Fabiano,S.;Harbuzaru,A.;PonceOrtiz,R.;Chen,L.X.;Facchetti,A.;Marks,T.J.ProcessablehighelectronmobilityЅа-copolymers via mesoscalebackboneconformationalordering. Adv. Funct. Mater. 2021 , 31 ,2009359..

Views

247

Downloads

CSCD

Alert me when the article has been cited

Submit

Tools

Publicity Resources

Thiazole-Flanked Thiazoloisoindigo as a Monomer for Balanced Ambipolar Polymeric Field-effect Transistors

Finely Tuned Electron/Hole Transport Preference of Thiazoloisoindigo- based Conjugated Polymers by Incorporation of Heavy Chalcogenophenes

Energy Storage Performance of Supercapacitors with Polyelectrolyte Surface Coatings: Effects of Dielectric Contrast

Preparation and Chiral Recognition Ability of Crystalline Cellulose Phenylcarbamate

Enhanced Segment Mobility Promotes Stereocomplex Crystallization in Polymer Blends via Elevated Segmental Miscibility

Related Author

Jian Pei

Liang Li

You-Bing Mu

Jie-Yu Wang

Si-Yu Lv

Qi-Yi Li

Xiao-Bo Wan

You-Bing Mu

Related Institution

School of Materials Science and Engineering, Wuhan Institute of Technology

Key Laboratory of Optoelectronic Chemical Materials and Devices, Ministry of Education, School of Chemical & Environmental Engineering, Jianghan University

Qingdao Institute of Bioenergy & Bioprocess Technology, Chinese Academy of Sciences

⁰