Bithiophene-imide-based polymeric semiconductors for field-effect transistors: Synthesis, structure-property correlations, charge carrier polarity, and device stability

Xugang Guo, Rocio Ponce Ortiz, Yan Zheng, Yan Hu, Yong Young Noh, Kang Jun Baeg, Antonio Facchetti, Tobin J Marks

Research output: Contribution to journalArticle

167 Citations (Scopus)

Abstract

Developing new high-mobility polymeric semiconductors with good processability and excellent device environmental stability is essential for organic electronics. We report the synthesis, characterization, manipulation of charge carrier polarity, and device air stability of a new series of bithiophene-imide (BTI)-based polymers for organic field-effect transistors (OFETs). By increasing the conjugation length of the donor comonomer unit from monothiophene (P1) to bithiophene (P2) to tetrathiophene (P3), the electron transport capacity decreases while the hole transport capacity increases. Compared to the BTI homopolymer P(BTimR) having an electron mobility of 10 -2 cm2 V-1 s-1, copolymer P1 is ambipolar with balanced hole and electron mobilities of ∼10-4 cm2 V-1 s-1, while P2 and P3 exhibit hole mobilities of ∼10-3 and ∼10-2 cm2 V-1 s-1, respectively. The influence of P(BTimR) homopolymer Mn on film morphology and device performance was also investigated. The high Mn batch P(BTimR)-H affords more crystalline film microstructures; hence, 3- increased electron mobility (0.038 cm 2 V-1 s-1) over the low Mn one P(BTimR)-L (0.011 cm2 V-1 s-1). In a top-gate/bottom-contact OFET architecture, P(BTimR)-H achieves a high electron mobility of 0.14 cm2 V-1 s-1, only slightly lower than that of state-of-the-art n-type polymer semiconductors. However, the high-lying P(BTimR)-H LUMO results in minimal electron transport on exposure to ambient. Copolymer P3 exhibits a hole mobility approaching 0.1 cm2 V-1 s-1 in top-gate OFETs, comparable to or slightly lower than current state-of-the-art p-type polymer semiconductors (0.1-0.6 cm 2 V-1 s-1). Although BTI building block incorporation does not enable air-stable n-type OFET performance for P(BTimR) or P1, it significantly increases the OFET air stability for p-type P2 and P3. Bottom-gate/top-contact and top-gate/bottom-contact P2 and P3 OFETs exhibit excellent stability in the ambient. Thus, P2 and P3 OFET hole mobilities are almost unchanged after 200 days under ambient, which is attributed to their low-lying HOMOs (>0.2 eV lower than that of P3HT), induced by the strong BTI electron-withdrawing capacity. Complementary inverters were fabricated by inkjet patterning of P(BTimR)-H (n-type) and P3b (p-type).

Original languageEnglish
Pages (from-to)1405-1418
Number of pages14
JournalJournal of the American Chemical Society
Volume133
Issue number5
DOIs
Publication statusPublished - Feb 9 2011

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Imides
Organic field effect transistors
Semiconductors
Field effect transistors
Charge carriers
Electrons
Semiconductor materials
Hole mobility
Electron mobility
Equipment and Supplies
Polymers
Air
Electron Transport
Homopolymerization
Copolymers
Electronic equipment
Crystalline materials
Microstructure

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Bithiophene-imide-based polymeric semiconductors for field-effect transistors : Synthesis, structure-property correlations, charge carrier polarity, and device stability. / Guo, Xugang; Ortiz, Rocio Ponce; Zheng, Yan; Hu, Yan; Noh, Yong Young; Baeg, Kang Jun; Facchetti, Antonio; Marks, Tobin J.

In: Journal of the American Chemical Society, Vol. 133, No. 5, 09.02.2011, p. 1405-1418.

Research output: Contribution to journalArticle

Guo, Xugang ; Ortiz, Rocio Ponce ; Zheng, Yan ; Hu, Yan ; Noh, Yong Young ; Baeg, Kang Jun ; Facchetti, Antonio ; Marks, Tobin J. / Bithiophene-imide-based polymeric semiconductors for field-effect transistors : Synthesis, structure-property correlations, charge carrier polarity, and device stability. In: Journal of the American Chemical Society. 2011 ; Vol. 133, No. 5. pp. 1405-1418.
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abstract = "Developing new high-mobility polymeric semiconductors with good processability and excellent device environmental stability is essential for organic electronics. We report the synthesis, characterization, manipulation of charge carrier polarity, and device air stability of a new series of bithiophene-imide (BTI)-based polymers for organic field-effect transistors (OFETs). By increasing the conjugation length of the donor comonomer unit from monothiophene (P1) to bithiophene (P2) to tetrathiophene (P3), the electron transport capacity decreases while the hole transport capacity increases. Compared to the BTI homopolymer P(BTimR) having an electron mobility of 10 -2 cm2 V-1 s-1, copolymer P1 is ambipolar with balanced hole and electron mobilities of ∼10-4 cm2 V-1 s-1, while P2 and P3 exhibit hole mobilities of ∼10-3 and ∼10-2 cm2 V-1 s-1, respectively. The influence of P(BTimR) homopolymer Mn on film morphology and device performance was also investigated. The high Mn batch P(BTimR)-H affords more crystalline film microstructures; hence, 3- increased electron mobility (0.038 cm 2 V-1 s-1) over the low Mn one P(BTimR)-L (0.011 cm2 V-1 s-1). In a top-gate/bottom-contact OFET architecture, P(BTimR)-H achieves a high electron mobility of 0.14 cm2 V-1 s-1, only slightly lower than that of state-of-the-art n-type polymer semiconductors. However, the high-lying P(BTimR)-H LUMO results in minimal electron transport on exposure to ambient. Copolymer P3 exhibits a hole mobility approaching 0.1 cm2 V-1 s-1 in top-gate OFETs, comparable to or slightly lower than current state-of-the-art p-type polymer semiconductors (0.1-0.6 cm 2 V-1 s-1). Although BTI building block incorporation does not enable air-stable n-type OFET performance for P(BTimR) or P1, it significantly increases the OFET air stability for p-type P2 and P3. Bottom-gate/top-contact and top-gate/bottom-contact P2 and P3 OFETs exhibit excellent stability in the ambient. Thus, P2 and P3 OFET hole mobilities are almost unchanged after 200 days under ambient, which is attributed to their low-lying HOMOs (>0.2 eV lower than that of P3HT), induced by the strong BTI electron-withdrawing capacity. Complementary inverters were fabricated by inkjet patterning of P(BTimR)-H (n-type) and P3b (p-type).",
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N2 - Developing new high-mobility polymeric semiconductors with good processability and excellent device environmental stability is essential for organic electronics. We report the synthesis, characterization, manipulation of charge carrier polarity, and device air stability of a new series of bithiophene-imide (BTI)-based polymers for organic field-effect transistors (OFETs). By increasing the conjugation length of the donor comonomer unit from monothiophene (P1) to bithiophene (P2) to tetrathiophene (P3), the electron transport capacity decreases while the hole transport capacity increases. Compared to the BTI homopolymer P(BTimR) having an electron mobility of 10 -2 cm2 V-1 s-1, copolymer P1 is ambipolar with balanced hole and electron mobilities of ∼10-4 cm2 V-1 s-1, while P2 and P3 exhibit hole mobilities of ∼10-3 and ∼10-2 cm2 V-1 s-1, respectively. The influence of P(BTimR) homopolymer Mn on film morphology and device performance was also investigated. The high Mn batch P(BTimR)-H affords more crystalline film microstructures; hence, 3- increased electron mobility (0.038 cm 2 V-1 s-1) over the low Mn one P(BTimR)-L (0.011 cm2 V-1 s-1). In a top-gate/bottom-contact OFET architecture, P(BTimR)-H achieves a high electron mobility of 0.14 cm2 V-1 s-1, only slightly lower than that of state-of-the-art n-type polymer semiconductors. However, the high-lying P(BTimR)-H LUMO results in minimal electron transport on exposure to ambient. Copolymer P3 exhibits a hole mobility approaching 0.1 cm2 V-1 s-1 in top-gate OFETs, comparable to or slightly lower than current state-of-the-art p-type polymer semiconductors (0.1-0.6 cm 2 V-1 s-1). Although BTI building block incorporation does not enable air-stable n-type OFET performance for P(BTimR) or P1, it significantly increases the OFET air stability for p-type P2 and P3. Bottom-gate/top-contact and top-gate/bottom-contact P2 and P3 OFETs exhibit excellent stability in the ambient. Thus, P2 and P3 OFET hole mobilities are almost unchanged after 200 days under ambient, which is attributed to their low-lying HOMOs (>0.2 eV lower than that of P3HT), induced by the strong BTI electron-withdrawing capacity. Complementary inverters were fabricated by inkjet patterning of P(BTimR)-H (n-type) and P3b (p-type).

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