Straight chain D-A copolymers based on thienothiophene and benzothiadiazole for efficient polymer field effect transistors and photovoltaic cells

Yuxiang Li, Tack Ho Lee, Song Yi Park, Mohammad Afsar Uddin, Taehyo Kim, Sungu Hwang, Jin Young Kim, Han Young Woo

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

Three types of linear and planar-structured donor (D)-acceptor (A) type alternating copolymers were synthesized by incorporating intrachain noncovalent Coulombic interactions, based on thieno[3,2-b]thiophene and benzothiadiazole (BT) moieties. The chain linearity and fine adjustment of interchain organization by the incorporation of different numbers of electronegative fluorine atoms onto BT, significantly affected the frontier energy levels, film morphology, and the resulting charge transport properties. The semi-crystalline morphology and charge carrier transport properties were studied by grazing incidence wide-angle X-ray scattering and polymer field-effect transistor (PFET) characteristic measurements. A hole mobility as high as 0.1 cm2 V-1 s-1 in PFET was obtained for poly[2,5-bis(decyltetradecyloxy)benzene-alt-4,7-bis(thieno[3,2-b]thiophene)-5,6-difluoro-2,1,3-benzothiadiazole] (PPDTT2FBT), suggesting a strong self-organization due to the linear chain configuration with conformation lock. The difluorinated PPDTT2FBT also showed the highest power conversion efficiency (PCE, 6.4%) by blending with PC71BM, but a poorer photovoltaic performance was obtained compared to the wavy-structured counterpart, poly[2,5-bis(2-hexyldecyloxy)phenylene-alt-5,6-difluoro-4,7-di(thiophen-2-yl)-2,1,3-benzothiadiazole] (PPDT2FBT), reported previously. The mainly edge-on orientation of PPDTT2FBT (with π-π stacking in both xy and z directions) is attributed to the moderate PCE in the blends. Fine modulation of chain linearity may suggest an effective way to control the desirable interchain ordering and bulk film morphology for specific application in polymer solar cells or field effect transistors.

Original languageEnglish
Pages (from-to)4638-4646
Number of pages9
JournalPolymer Chemistry
Volume7
Issue number28
DOIs
Publication statusPublished - 2016 Jul 28

Fingerprint

Photovoltaic cells
Field effect transistors
Polymers
Copolymers
Thiophene
Thiophenes
Transport properties
Hole mobility
Carrier transport
Charge carriers
X ray scattering
Fluorine
Electron energy levels
Conversion efficiency
Conformations
Charge transfer
Benzene
Modulation
Crystalline materials
Atoms

ASJC Scopus subject areas

  • Bioengineering
  • Biochemistry
  • Polymers and Plastics
  • Organic Chemistry

Cite this

Straight chain D-A copolymers based on thienothiophene and benzothiadiazole for efficient polymer field effect transistors and photovoltaic cells. / Li, Yuxiang; Lee, Tack Ho; Park, Song Yi; Uddin, Mohammad Afsar; Kim, Taehyo; Hwang, Sungu; Kim, Jin Young; Woo, Han Young.

In: Polymer Chemistry, Vol. 7, No. 28, 28.07.2016, p. 4638-4646.

Research output: Contribution to journalArticle

Li, Yuxiang ; Lee, Tack Ho ; Park, Song Yi ; Uddin, Mohammad Afsar ; Kim, Taehyo ; Hwang, Sungu ; Kim, Jin Young ; Woo, Han Young. / Straight chain D-A copolymers based on thienothiophene and benzothiadiazole for efficient polymer field effect transistors and photovoltaic cells. In: Polymer Chemistry. 2016 ; Vol. 7, No. 28. pp. 4638-4646.
@article{f39c3bafadd740d7b4d79e767188f5b9,
title = "Straight chain D-A copolymers based on thienothiophene and benzothiadiazole for efficient polymer field effect transistors and photovoltaic cells",
abstract = "Three types of linear and planar-structured donor (D)-acceptor (A) type alternating copolymers were synthesized by incorporating intrachain noncovalent Coulombic interactions, based on thieno[3,2-b]thiophene and benzothiadiazole (BT) moieties. The chain linearity and fine adjustment of interchain organization by the incorporation of different numbers of electronegative fluorine atoms onto BT, significantly affected the frontier energy levels, film morphology, and the resulting charge transport properties. The semi-crystalline morphology and charge carrier transport properties were studied by grazing incidence wide-angle X-ray scattering and polymer field-effect transistor (PFET) characteristic measurements. A hole mobility as high as 0.1 cm2 V-1 s-1 in PFET was obtained for poly[2,5-bis(decyltetradecyloxy)benzene-alt-4,7-bis(thieno[3,2-b]thiophene)-5,6-difluoro-2,1,3-benzothiadiazole] (PPDTT2FBT), suggesting a strong self-organization due to the linear chain configuration with conformation lock. The difluorinated PPDTT2FBT also showed the highest power conversion efficiency (PCE, 6.4{\%}) by blending with PC71BM, but a poorer photovoltaic performance was obtained compared to the wavy-structured counterpart, poly[2,5-bis(2-hexyldecyloxy)phenylene-alt-5,6-difluoro-4,7-di(thiophen-2-yl)-2,1,3-benzothiadiazole] (PPDT2FBT), reported previously. The mainly edge-on orientation of PPDTT2FBT (with π-π stacking in both xy and z directions) is attributed to the moderate PCE in the blends. Fine modulation of chain linearity may suggest an effective way to control the desirable interchain ordering and bulk film morphology for specific application in polymer solar cells or field effect transistors.",
author = "Yuxiang Li and Lee, {Tack Ho} and Park, {Song Yi} and Uddin, {Mohammad Afsar} and Taehyo Kim and Sungu Hwang and Kim, {Jin Young} and Woo, {Han Young}",
year = "2016",
month = "7",
day = "28",
doi = "10.1039/c6py00674d",
language = "English",
volume = "7",
pages = "4638--4646",
journal = "Polymer Chemistry",
issn = "1759-9954",
publisher = "Royal Society of Chemistry",
number = "28",

}

TY - JOUR

T1 - Straight chain D-A copolymers based on thienothiophene and benzothiadiazole for efficient polymer field effect transistors and photovoltaic cells

AU - Li, Yuxiang

AU - Lee, Tack Ho

AU - Park, Song Yi

AU - Uddin, Mohammad Afsar

AU - Kim, Taehyo

AU - Hwang, Sungu

AU - Kim, Jin Young

AU - Woo, Han Young

PY - 2016/7/28

Y1 - 2016/7/28

N2 - Three types of linear and planar-structured donor (D)-acceptor (A) type alternating copolymers were synthesized by incorporating intrachain noncovalent Coulombic interactions, based on thieno[3,2-b]thiophene and benzothiadiazole (BT) moieties. The chain linearity and fine adjustment of interchain organization by the incorporation of different numbers of electronegative fluorine atoms onto BT, significantly affected the frontier energy levels, film morphology, and the resulting charge transport properties. The semi-crystalline morphology and charge carrier transport properties were studied by grazing incidence wide-angle X-ray scattering and polymer field-effect transistor (PFET) characteristic measurements. A hole mobility as high as 0.1 cm2 V-1 s-1 in PFET was obtained for poly[2,5-bis(decyltetradecyloxy)benzene-alt-4,7-bis(thieno[3,2-b]thiophene)-5,6-difluoro-2,1,3-benzothiadiazole] (PPDTT2FBT), suggesting a strong self-organization due to the linear chain configuration with conformation lock. The difluorinated PPDTT2FBT also showed the highest power conversion efficiency (PCE, 6.4%) by blending with PC71BM, but a poorer photovoltaic performance was obtained compared to the wavy-structured counterpart, poly[2,5-bis(2-hexyldecyloxy)phenylene-alt-5,6-difluoro-4,7-di(thiophen-2-yl)-2,1,3-benzothiadiazole] (PPDT2FBT), reported previously. The mainly edge-on orientation of PPDTT2FBT (with π-π stacking in both xy and z directions) is attributed to the moderate PCE in the blends. Fine modulation of chain linearity may suggest an effective way to control the desirable interchain ordering and bulk film morphology for specific application in polymer solar cells or field effect transistors.

AB - Three types of linear and planar-structured donor (D)-acceptor (A) type alternating copolymers were synthesized by incorporating intrachain noncovalent Coulombic interactions, based on thieno[3,2-b]thiophene and benzothiadiazole (BT) moieties. The chain linearity and fine adjustment of interchain organization by the incorporation of different numbers of electronegative fluorine atoms onto BT, significantly affected the frontier energy levels, film morphology, and the resulting charge transport properties. The semi-crystalline morphology and charge carrier transport properties were studied by grazing incidence wide-angle X-ray scattering and polymer field-effect transistor (PFET) characteristic measurements. A hole mobility as high as 0.1 cm2 V-1 s-1 in PFET was obtained for poly[2,5-bis(decyltetradecyloxy)benzene-alt-4,7-bis(thieno[3,2-b]thiophene)-5,6-difluoro-2,1,3-benzothiadiazole] (PPDTT2FBT), suggesting a strong self-organization due to the linear chain configuration with conformation lock. The difluorinated PPDTT2FBT also showed the highest power conversion efficiency (PCE, 6.4%) by blending with PC71BM, but a poorer photovoltaic performance was obtained compared to the wavy-structured counterpart, poly[2,5-bis(2-hexyldecyloxy)phenylene-alt-5,6-difluoro-4,7-di(thiophen-2-yl)-2,1,3-benzothiadiazole] (PPDT2FBT), reported previously. The mainly edge-on orientation of PPDTT2FBT (with π-π stacking in both xy and z directions) is attributed to the moderate PCE in the blends. Fine modulation of chain linearity may suggest an effective way to control the desirable interchain ordering and bulk film morphology for specific application in polymer solar cells or field effect transistors.

UR - http://www.scopus.com/inward/record.url?scp=84978823421&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84978823421&partnerID=8YFLogxK

U2 - 10.1039/c6py00674d

DO - 10.1039/c6py00674d

M3 - Article

AN - SCOPUS:84978823421

VL - 7

SP - 4638

EP - 4646

JO - Polymer Chemistry

JF - Polymer Chemistry

SN - 1759-9954

IS - 28

ER -