High-performance amorphous donor-acceptor conjugated polymers containing x-shaped anthracene-based monomer and 2,5-bis(2-octyldodecyl)pyrrolo[3,4-c] pyrrole-1,4(2H,5H)-dione for organic thin-film transistors

Joo Bin Lee, Kyung Hwan Kim, Chang Seop Hong, Dong Hoon Choi

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

New diketopyrrolopyrrole (DPP)-containing amorphous conjugated polymers, such as poly(3-(5-((9,10-bis((4-hexylphenyl)ethynyl)-6-(prop-1-ynyl)anthracen-2- yl)ethynyl) thiophen-2-yl)-5-(2-hexyldecyl)-2-(2-octyldodecyl)-6-(thiophen-2-yl) pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione) (4), and poly(3-(5-((2,6-bis((4- hexylphenyl)ethynyl)-10-(prop-1-ynyl)anthracen-9-yl)ethynyl)thiophen-2-yl)-2, 5-bis(2-octyldodecyl)-6-(thio phen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione) (7), were successfully synthesized via Sonogashira coupling reactions under microwave conditions. Copolymer 7, incorporating a DPP moiety at the 9,10-position of the anthracene ring through a triple bond, showed a much lower bandgap energy (E g = 1.81 eV) than copolymer 4 (E g = 2.13 eV). Tuning of the molecular frontier orbital energies was achieved by only changing the anchoring position of dithiophenyl-DPP from the 2,6- to the 9,10-position in the anthracene ring. Because of the donor-acceptor (D-A) interaction and the two-dimensional planar structure of the X-shaped donor monomer, the resulting polymers showed good interchain π-π stacking in the thin-film state, despite being amorphous polymers. When the newly synthesized polymer 7 was used as a semiconductor material in an organic thin-film transistor, the best mobility of up to 0.12 cm 2 V -1 s -1 (I on/off = ∼ 4.4 × 10 6) was observed, which is one of the highest values recorded for amorphous polymer films reported to date.

Original languageEnglish
Pages (from-to)2809-2818
Number of pages10
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume50
Issue number14
DOIs
Publication statusPublished - 2012 Jul 15

Fingerprint

Pyrroles
Anthracene
Conjugated polymers
Thin film transistors
Polymers
Monomers
Copolymers
Molecular orbitals
Amorphous films
Polymer films
Energy gap
Tuning
Microwaves
Semiconductor materials
Thin films
anthracene

Keywords

  • charge transport
  • conjugated polymer
  • copolymerization
  • heteroatom-containing polymers
  • noncrystalline polymers
  • synthesis

ASJC Scopus subject areas

  • Materials Chemistry
  • Polymers and Plastics
  • Organic Chemistry

Cite this

@article{65694eb880e24068ba24e1b15112e665,
title = "High-performance amorphous donor-acceptor conjugated polymers containing x-shaped anthracene-based monomer and 2,5-bis(2-octyldodecyl)pyrrolo[3,4-c] pyrrole-1,4(2H,5H)-dione for organic thin-film transistors",
abstract = "New diketopyrrolopyrrole (DPP)-containing amorphous conjugated polymers, such as poly(3-(5-((9,10-bis((4-hexylphenyl)ethynyl)-6-(prop-1-ynyl)anthracen-2- yl)ethynyl) thiophen-2-yl)-5-(2-hexyldecyl)-2-(2-octyldodecyl)-6-(thiophen-2-yl) pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione) (4), and poly(3-(5-((2,6-bis((4- hexylphenyl)ethynyl)-10-(prop-1-ynyl)anthracen-9-yl)ethynyl)thiophen-2-yl)-2, 5-bis(2-octyldodecyl)-6-(thio phen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione) (7), were successfully synthesized via Sonogashira coupling reactions under microwave conditions. Copolymer 7, incorporating a DPP moiety at the 9,10-position of the anthracene ring through a triple bond, showed a much lower bandgap energy (E g = 1.81 eV) than copolymer 4 (E g = 2.13 eV). Tuning of the molecular frontier orbital energies was achieved by only changing the anchoring position of dithiophenyl-DPP from the 2,6- to the 9,10-position in the anthracene ring. Because of the donor-acceptor (D-A) interaction and the two-dimensional planar structure of the X-shaped donor monomer, the resulting polymers showed good interchain π-π stacking in the thin-film state, despite being amorphous polymers. When the newly synthesized polymer 7 was used as a semiconductor material in an organic thin-film transistor, the best mobility of up to 0.12 cm 2 V -1 s -1 (I on/off = ∼ 4.4 × 10 6) was observed, which is one of the highest values recorded for amorphous polymer films reported to date.",
keywords = "charge transport, conjugated polymer, copolymerization, heteroatom-containing polymers, noncrystalline polymers, synthesis",
author = "Lee, {Joo Bin} and Kim, {Kyung Hwan} and Hong, {Chang Seop} and Choi, {Dong Hoon}",
year = "2012",
month = "7",
day = "15",
doi = "10.1002/pola.26078",
language = "English",
volume = "50",
pages = "2809--2818",
journal = "Journal of Polymer Science, Part A: Polymer Chemistry",
issn = "0887-624X",
publisher = "John Wiley and Sons Inc.",
number = "14",

}

TY - JOUR

T1 - High-performance amorphous donor-acceptor conjugated polymers containing x-shaped anthracene-based monomer and 2,5-bis(2-octyldodecyl)pyrrolo[3,4-c] pyrrole-1,4(2H,5H)-dione for organic thin-film transistors

AU - Lee, Joo Bin

AU - Kim, Kyung Hwan

AU - Hong, Chang Seop

AU - Choi, Dong Hoon

PY - 2012/7/15

Y1 - 2012/7/15

N2 - New diketopyrrolopyrrole (DPP)-containing amorphous conjugated polymers, such as poly(3-(5-((9,10-bis((4-hexylphenyl)ethynyl)-6-(prop-1-ynyl)anthracen-2- yl)ethynyl) thiophen-2-yl)-5-(2-hexyldecyl)-2-(2-octyldodecyl)-6-(thiophen-2-yl) pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione) (4), and poly(3-(5-((2,6-bis((4- hexylphenyl)ethynyl)-10-(prop-1-ynyl)anthracen-9-yl)ethynyl)thiophen-2-yl)-2, 5-bis(2-octyldodecyl)-6-(thio phen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione) (7), were successfully synthesized via Sonogashira coupling reactions under microwave conditions. Copolymer 7, incorporating a DPP moiety at the 9,10-position of the anthracene ring through a triple bond, showed a much lower bandgap energy (E g = 1.81 eV) than copolymer 4 (E g = 2.13 eV). Tuning of the molecular frontier orbital energies was achieved by only changing the anchoring position of dithiophenyl-DPP from the 2,6- to the 9,10-position in the anthracene ring. Because of the donor-acceptor (D-A) interaction and the two-dimensional planar structure of the X-shaped donor monomer, the resulting polymers showed good interchain π-π stacking in the thin-film state, despite being amorphous polymers. When the newly synthesized polymer 7 was used as a semiconductor material in an organic thin-film transistor, the best mobility of up to 0.12 cm 2 V -1 s -1 (I on/off = ∼ 4.4 × 10 6) was observed, which is one of the highest values recorded for amorphous polymer films reported to date.

AB - New diketopyrrolopyrrole (DPP)-containing amorphous conjugated polymers, such as poly(3-(5-((9,10-bis((4-hexylphenyl)ethynyl)-6-(prop-1-ynyl)anthracen-2- yl)ethynyl) thiophen-2-yl)-5-(2-hexyldecyl)-2-(2-octyldodecyl)-6-(thiophen-2-yl) pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione) (4), and poly(3-(5-((2,6-bis((4- hexylphenyl)ethynyl)-10-(prop-1-ynyl)anthracen-9-yl)ethynyl)thiophen-2-yl)-2, 5-bis(2-octyldodecyl)-6-(thio phen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione) (7), were successfully synthesized via Sonogashira coupling reactions under microwave conditions. Copolymer 7, incorporating a DPP moiety at the 9,10-position of the anthracene ring through a triple bond, showed a much lower bandgap energy (E g = 1.81 eV) than copolymer 4 (E g = 2.13 eV). Tuning of the molecular frontier orbital energies was achieved by only changing the anchoring position of dithiophenyl-DPP from the 2,6- to the 9,10-position in the anthracene ring. Because of the donor-acceptor (D-A) interaction and the two-dimensional planar structure of the X-shaped donor monomer, the resulting polymers showed good interchain π-π stacking in the thin-film state, despite being amorphous polymers. When the newly synthesized polymer 7 was used as a semiconductor material in an organic thin-film transistor, the best mobility of up to 0.12 cm 2 V -1 s -1 (I on/off = ∼ 4.4 × 10 6) was observed, which is one of the highest values recorded for amorphous polymer films reported to date.

KW - charge transport

KW - conjugated polymer

KW - copolymerization

KW - heteroatom-containing polymers

KW - noncrystalline polymers

KW - synthesis

UR - http://www.scopus.com/inward/record.url?scp=84861824925&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84861824925&partnerID=8YFLogxK

U2 - 10.1002/pola.26078

DO - 10.1002/pola.26078

M3 - Article

VL - 50

SP - 2809

EP - 2818

JO - Journal of Polymer Science, Part A: Polymer Chemistry

JF - Journal of Polymer Science, Part A: Polymer Chemistry

SN - 0887-624X

IS - 14

ER -