Regioisomeric wide-band-gap polymers with different fluorine topologies for non-fullerene organic solar cells

Yuxiang Li, Jin Woo Lee, Minseok Kim, Changyeon Lee, Young Woong Lee, Bumjoon J. Kim, Han Young Woo

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Two regioisomeric wide-band-gap donor polymers with different fluorine topologies are designed and synthesized for use in nonfullerene organic solar cells (NFOSCs). Two fluorine atoms are substituted on the phenylene moiety in an anti (PTBDD2F-a) or a syn (PTBDD2F-s) fashion. The two isomeric polymers show nearly identical optical, thermal, and electrochemical properties, but exhibit different interchain packing and film morphologies in both pristine and blend films with an n-type acceptor (ITIC). These different morphological properties are related to differences in the molecular dipole, symmetry, and backbone curvatures of PTBDD2F-a and PTBDD2F-s, which influence the interchain packing and resulting electrical properties. From grazing incidence X-ray scattering measurements, PTBDD2F-a:ITIC shows more pronounced and two separate out-of-plane (010) peaks compared to PTBDD2F-s:ITIC, suggesting a stronger face-on cofacial packing of ITIC molecules in the PTBDD2F-a:ITIC blend. A higher domain purity (1.00 vs. 0.71) is also observed for PTBDD2F-a:ITIC compared to PTBDD2F-s:ITIC in the resonant soft X-ray scattering measurements. These different morphological features induce ∼2.5 times higher hole mobility and ∼6 times higher electron mobility with higher power conversion efficiency (6.60 vs. 5.47%) for PTBDD2F-a:ITIC than for PTBDD2F-s:ITIC. This comparative study highlights the effects of different fluorine topologies along the polymer backbone, which should be carefully considered to optimize the blend morphology and optoelectronic properties of NFOSCs.

Original languageEnglish
Pages (from-to)395-402
Number of pages8
JournalPolymer Chemistry
Volume10
Issue number3
DOIs
Publication statusPublished - 2019 Jan 21

Fingerprint

Fluorine
Polymers
Energy gap
Topology
X ray scattering
X-Rays
Hole mobility
Electron mobility
Electrochemical properties
Optoelectronic devices
Conversion efficiency
Electric properties
Thermodynamic properties
Optical properties
Hot Temperature
Electrons
Atoms
Molecules
Incidence
Organic solar cells

ASJC Scopus subject areas

  • Bioengineering
  • Biochemistry
  • Polymers and Plastics
  • Organic Chemistry

Cite this

Regioisomeric wide-band-gap polymers with different fluorine topologies for non-fullerene organic solar cells. / Li, Yuxiang; Lee, Jin Woo; Kim, Minseok; Lee, Changyeon; Lee, Young Woong; Kim, Bumjoon J.; Woo, Han Young.

In: Polymer Chemistry, Vol. 10, No. 3, 21.01.2019, p. 395-402.

Research output: Contribution to journalArticle

Li, Yuxiang ; Lee, Jin Woo ; Kim, Minseok ; Lee, Changyeon ; Lee, Young Woong ; Kim, Bumjoon J. ; Woo, Han Young. / Regioisomeric wide-band-gap polymers with different fluorine topologies for non-fullerene organic solar cells. In: Polymer Chemistry. 2019 ; Vol. 10, No. 3. pp. 395-402.
@article{946321d2b0b74031970ad3ed3820f3b0,
title = "Regioisomeric wide-band-gap polymers with different fluorine topologies for non-fullerene organic solar cells",
abstract = "Two regioisomeric wide-band-gap donor polymers with different fluorine topologies are designed and synthesized for use in nonfullerene organic solar cells (NFOSCs). Two fluorine atoms are substituted on the phenylene moiety in an anti (PTBDD2F-a) or a syn (PTBDD2F-s) fashion. The two isomeric polymers show nearly identical optical, thermal, and electrochemical properties, but exhibit different interchain packing and film morphologies in both pristine and blend films with an n-type acceptor (ITIC). These different morphological properties are related to differences in the molecular dipole, symmetry, and backbone curvatures of PTBDD2F-a and PTBDD2F-s, which influence the interchain packing and resulting electrical properties. From grazing incidence X-ray scattering measurements, PTBDD2F-a:ITIC shows more pronounced and two separate out-of-plane (010) peaks compared to PTBDD2F-s:ITIC, suggesting a stronger face-on cofacial packing of ITIC molecules in the PTBDD2F-a:ITIC blend. A higher domain purity (1.00 vs. 0.71) is also observed for PTBDD2F-a:ITIC compared to PTBDD2F-s:ITIC in the resonant soft X-ray scattering measurements. These different morphological features induce ∼2.5 times higher hole mobility and ∼6 times higher electron mobility with higher power conversion efficiency (6.60 vs. 5.47{\%}) for PTBDD2F-a:ITIC than for PTBDD2F-s:ITIC. This comparative study highlights the effects of different fluorine topologies along the polymer backbone, which should be carefully considered to optimize the blend morphology and optoelectronic properties of NFOSCs.",
author = "Yuxiang Li and Lee, {Jin Woo} and Minseok Kim and Changyeon Lee and Lee, {Young Woong} and Kim, {Bumjoon J.} and Woo, {Han Young}",
year = "2019",
month = "1",
day = "21",
doi = "10.1039/c8py01458b",
language = "English",
volume = "10",
pages = "395--402",
journal = "Polymer Chemistry",
issn = "1759-9954",
publisher = "Royal Society of Chemistry",
number = "3",

}

TY - JOUR

T1 - Regioisomeric wide-band-gap polymers with different fluorine topologies for non-fullerene organic solar cells

AU - Li, Yuxiang

AU - Lee, Jin Woo

AU - Kim, Minseok

AU - Lee, Changyeon

AU - Lee, Young Woong

AU - Kim, Bumjoon J.

AU - Woo, Han Young

PY - 2019/1/21

Y1 - 2019/1/21

N2 - Two regioisomeric wide-band-gap donor polymers with different fluorine topologies are designed and synthesized for use in nonfullerene organic solar cells (NFOSCs). Two fluorine atoms are substituted on the phenylene moiety in an anti (PTBDD2F-a) or a syn (PTBDD2F-s) fashion. The two isomeric polymers show nearly identical optical, thermal, and electrochemical properties, but exhibit different interchain packing and film morphologies in both pristine and blend films with an n-type acceptor (ITIC). These different morphological properties are related to differences in the molecular dipole, symmetry, and backbone curvatures of PTBDD2F-a and PTBDD2F-s, which influence the interchain packing and resulting electrical properties. From grazing incidence X-ray scattering measurements, PTBDD2F-a:ITIC shows more pronounced and two separate out-of-plane (010) peaks compared to PTBDD2F-s:ITIC, suggesting a stronger face-on cofacial packing of ITIC molecules in the PTBDD2F-a:ITIC blend. A higher domain purity (1.00 vs. 0.71) is also observed for PTBDD2F-a:ITIC compared to PTBDD2F-s:ITIC in the resonant soft X-ray scattering measurements. These different morphological features induce ∼2.5 times higher hole mobility and ∼6 times higher electron mobility with higher power conversion efficiency (6.60 vs. 5.47%) for PTBDD2F-a:ITIC than for PTBDD2F-s:ITIC. This comparative study highlights the effects of different fluorine topologies along the polymer backbone, which should be carefully considered to optimize the blend morphology and optoelectronic properties of NFOSCs.

AB - Two regioisomeric wide-band-gap donor polymers with different fluorine topologies are designed and synthesized for use in nonfullerene organic solar cells (NFOSCs). Two fluorine atoms are substituted on the phenylene moiety in an anti (PTBDD2F-a) or a syn (PTBDD2F-s) fashion. The two isomeric polymers show nearly identical optical, thermal, and electrochemical properties, but exhibit different interchain packing and film morphologies in both pristine and blend films with an n-type acceptor (ITIC). These different morphological properties are related to differences in the molecular dipole, symmetry, and backbone curvatures of PTBDD2F-a and PTBDD2F-s, which influence the interchain packing and resulting electrical properties. From grazing incidence X-ray scattering measurements, PTBDD2F-a:ITIC shows more pronounced and two separate out-of-plane (010) peaks compared to PTBDD2F-s:ITIC, suggesting a stronger face-on cofacial packing of ITIC molecules in the PTBDD2F-a:ITIC blend. A higher domain purity (1.00 vs. 0.71) is also observed for PTBDD2F-a:ITIC compared to PTBDD2F-s:ITIC in the resonant soft X-ray scattering measurements. These different morphological features induce ∼2.5 times higher hole mobility and ∼6 times higher electron mobility with higher power conversion efficiency (6.60 vs. 5.47%) for PTBDD2F-a:ITIC than for PTBDD2F-s:ITIC. This comparative study highlights the effects of different fluorine topologies along the polymer backbone, which should be carefully considered to optimize the blend morphology and optoelectronic properties of NFOSCs.

UR - http://www.scopus.com/inward/record.url?scp=85060042998&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85060042998&partnerID=8YFLogxK

U2 - 10.1039/c8py01458b

DO - 10.1039/c8py01458b

M3 - Article

AN - SCOPUS:85060042998

VL - 10

SP - 395

EP - 402

JO - Polymer Chemistry

JF - Polymer Chemistry

SN - 1759-9954

IS - 3

ER -