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Asymmetrically Functionalized Electron-Deficient π-Conjugated System for Printed Single-Crystalline Organic

Craig P Yu1, Shohei Kumagai2, Michitsuna Tsutsumi1

  • 1Material Innovation Research Center (MIRC) and Department of Advanced Materials Science, Graduate School of Frontier Sciences, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba, 277-8561, Japan.

Advanced Science (Weinheim, Baden-Wurttemberg, Germany)
|September 15, 2023
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Summary

Researchers developed asymmetric organic semiconductors for high-performance electronics. This new design enables large-area, single-crystalline thin films with improved solubility and excellent electron mobility, advancing organic electronics applications.

Keywords:
asymmetric n-type organic semiconductorslarge-area single-crystalline thin filmsmolecular designnitrogen-containing π-electron systemsorganic field-effect transistors

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Area of Science:

  • Materials Science
  • Organic Electronics
  • Semiconductor Physics

Background:

  • Large-area single-crystalline n-type organic semiconductor (OSC) thin films are crucial for advanced electronics.
  • Existing molecular designs for n-type OSCs often lack a balance of charge transport, solution-processability, and robustness.
  • Benzo[de]isoquinolino[1,8-gh]quinolinetetracarboxylic diimide (BQQDI) derivatives show promise but suffer from poor solubility.

Purpose of the Study:

  • To design asymmetric BQQDI molecules that enhance solubility and solution-processability while retaining excellent charge transport.
  • To develop an effective synthetic strategy for producing these novel asymmetric BQQDI derivatives.
  • To investigate the structure-property relationships and electronic performance of the new materials.

Main Methods:

  • Asymmetric molecular design incorporating alkyl chains onto the BQQDI core.
  • Development of a synthetic route to produce asymmetric BQQDI derivatives (PhC2-BQQDI-Cn).
  • Characterization of molecular conformation, aggregation behavior, and thin-film properties.
  • Measurement of electron mobility and assessment of thin-film quality and scale.

Main Results:

  • Asymmetric PhC2-BQQDI-Cn molecules with linear alkyl chains (n=5-7) adopted a stable gauche conformation.
  • The asymmetric design significantly improved solubility and solution-processability compared to the parent PhC2-BQQDI.
  • Asymmetric PhC2-BQQDI-C5 achieved high electron mobility and enabled the fabrication of centimeter-scale continuous single-crystalline thin films.
  • The resulting films showed enhanced electron transport properties and allowed for the study of anisotropy.

Conclusions:

  • The asymmetric molecular design strategy is effective for creating solution-processable n-type OSCs with high performance.
  • PhC2-BQQDI-C5 represents a significant advancement, enabling large-area single-crystalline films for practical electronic applications.
  • This work provides a pathway for developing next-generation organic electronic devices based on tailored molecular architectures.