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Vapor-Induced Coating Method for Well-Aligned and Uniform Organic Semiconductor Single Crystals

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Abstract

Uniform and well-aligned organic semiconductor single crystals (OSSCs) are critical for high-performance electronic and optoelectronic device applications due to their long-range order and low defect density. However, it is still challenging to fabricate uniform and well-aligned OSSCs by an efficient and facile method. Here, we report a vapor-induced coating method to prepare uniform organic semiconductor stripe single crystals with well-aligned orientation. The coating velocity and solution concentration are important to control the stripe crystals’ morphology, which influence the triple-phase contact line dewetting behavior and then change the mass transport of the meniscus. Insufficient solute supply causes the generation of dendritic crystals. Uniform stripe single crystals of high quality and pure orientation are prepared in the condition of a sufficient and suitable solute supply. Moreover, the electronic and optoelectronic properties are evaluated. Notably, the polarization-sensitive photodetectors based on the uniform stripe crystals exhibit high polarization sensitivity and its dichroic ratio of photocurrent is 1.98. This method is efficient for the preparation of various high-quality and uniform organic semiconductor stripe single crystals, opening an opportunity for high-performance organic functional devices.

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References

  1. Wang, C.; Dong, H.; Jiang, L.; Hu, W. Organic semiconductor crystals. Chem. Soc. Rev. 2018, 47, 422–500.

    Article  CAS  PubMed  Google Scholar 

  2. Qian, J.; Jiang, S.; Li, S. L.; Wang, X. R.; Shi, Y.; Li, Y. Solution-processed 2D molecular crystals: fabrication techniques, transistor applications. and physics. Adv. Mater. Technol. 2018, 4, 1800182.

    Article  Google Scholar 

  3. Chen, S.; Li, Z.; Qiao, Y.; Song, Y. Solution-processed organic semiconductor crystals for field-effect transistors: from crystallization mechanism towards morphology control. J. Mater. Chem. C 2021, 9, 1126–1149.

    Article  CAS  Google Scholar 

  4. Wang, Y.; Sun, L.; Wang, C.; Yang, F.; Ren, X.; Zhang, X.; Dong, H.; Hu, W. Organic crystalline materials in flexible electronics. Chem. Soc. Rev. 2019, 48, 1492–1530.

    Article  CAS  PubMed  Google Scholar 

  5. Zhang, X.; Jie, J.; Deng, W.; Shang, Q.; Wang, J.; Wang, H.; Chen, X.; Zhang, X. Alignment and patterning of ordered small-molecule organic semiconductor micro-/nanocrystals for device applications. Adv. Mater. 2016, 28, 2475–2503.

    Article  CAS  PubMed  Google Scholar 

  6. Yao, Y.; Dong, H.; Hu, W. Charge transport in organic and polymeric semiconductors for flexible and stretchable devices. Adv. Mater. 2016, 28, 4513–4523.

    Article  CAS  PubMed  Google Scholar 

  7. Yang, Y.; Li, X.; Wang, S.; Duan, X.; Cai, Y.; Sun, X.; Wei, D.; Ma, W.; Sun, Y. An organic small molecule as a solid additive in non-fullerene organic solar cells with improved efficiency and operational stability. Chinese J. Polym. Sci. 2022, 41, 194–201.

    Article  Google Scholar 

  8. Xiao, C.; Kan, X.; Liu, C.; Jiang, W.; Zhao, G.; Zhao, Q.; Zhang, L.; Hu, W.; Wang, Z.; Jiang, L. Controlled formation of large-area single-crystalline TIPS-pentacene arrays through superhydrophobic micropillar flow-coating. J. Mater. Chem. C 2017, 5, 2702–2707.

    Article  CAS  Google Scholar 

  9. Wu, Y.; Feng, J.; Su, B.; Jiang, L. 3D dewetting for crystal patterning: Toward regular single-crystalline belt arrays and their functionality. Adv. Mater. 2016, 28, 2266–2273.

    Article  CAS  PubMed  Google Scholar 

  10. Wei, X.; Gao, H.; Feng, J.; Pi, Y.; Zhang, B.; Zhai, Y.; Wen, W.; He, M.; Matthews, J. R.; Wang, H.; Li, Y.; Jiang, S.; Jiang, L.; Wu, Y. Highly ordered semiconducting polymer arrays for sensitive photodetectors. ACS Appl. Mater. Interfaces 2019, 11, 15829–15836.

    Article  CAS  PubMed  Google Scholar 

  11. Liu, Y.; Feng, J.; Zhang, B.; Wu, Y.; Chen, Y.; Jiang, L. Regular aligned 1D single-crystalline supramolecular arrays for photodetectors. Small 2018, 14, 1701861.

    Article  Google Scholar 

  12. Qin, Z.; Gao, C.; Dong, H.; Hu, W. Organic semiconductor single-crystal light-emitting transistors. Adv. Opt. Mater. 2022, 2201644.

    Google Scholar 

  13. Ding, R.; Feng, J.; Dong, F.; Zhou, W.; Liu, Y.; Zhang, X.; Wang, X.; Fang, H.; Xu, B.; Li, X.; Wang, H.; Hotta, S.; Sun, H. Highly efficient three primary color organic single-crystal light-emitting devices with balanced carrier injection and transport. Adv. Funct. Mater. 2017, 27, 1604659.

    Article  Google Scholar 

  14. Wang, P.; Zhu, Y.; Tao, H.; Ma, Y.; Cai, D.; Tu, Q.; Liao, R.; Zheng, Q. Polymerizing ladder-type heteroheptacene-cored small-molecule acceptors for efficient all-polymer solar cells. Chinese J. Polym. Sci. 2023, DOI: https://doi.org/10.1007/s10118-023-2909-3.

  15. Li, H.; Tee, B. C.; Cha, J. J.; Cui, Y.; Chung, J. W.; Lee, S. Y.; Bao, Z. High-mobility field-effect transistors from large-area solution-grown aligned C60 single crystals. J. Am. Chem. Soc. 2012, 134, 2760–2765.

    Article  CAS  PubMed  Google Scholar 

  16. Peng, B.; Wu, R.; Li, H. Crystallization from a droplet: single-crystalline arrays and heterojunctions for organic electronics. Acc. Chem. Res. 2021, 54, 4498–4507.

    Article  CAS  PubMed  Google Scholar 

  17. Minemawari, H.; Yamada, T.; Matsui, H.; Tsutsumi, J.; Haas, S.; Chiba, R.; Kumai, R.; Hasegawa, T. Inkjet printing of single-crystal films. Nature 2011, 475, 364–367.

    Article  CAS  PubMed  Google Scholar 

  18. Shaw, L.; Bao, Z. The large-area, solution-based deposition of single-crystal organic semiconductors. Isr. J. Chem. 2014, 54, 496–512.

    Article  CAS  Google Scholar 

  19. Diao, Y.; Shaw, L.; Bao, Z.; Mannsfeld, S. C. B. Morphology control strategies for solution-processed organic semiconductor thin films. Energy Environ. Sci. 2014, 7, 2145–2159.

    Article  CAS  Google Scholar 

  20. Fu, B.; Yang, F.; Sun, L.; Zhao, Q.; Ji, D.; Sun, Y.; Zhang, X.; Hu, W. Challenging bendable organic single crystal and transistor arrays with high mobility and durability toward flexible electronics. Adv. Mater. 2022, 34, 2203330.

    Article  CAS  Google Scholar 

  21. Chen, M.; Peng, B.; Huang, S.; Chan, P. K. L. Understanding the meniscus-guided coating parameters in organic field-effect-transistor fabrications. Adv. Funct. Mater. 2020, 30, 1905963.

    Article  CAS  Google Scholar 

  22. Li, L.; Gao, P.; Wang, W.; Mullen, K.; Fuchs, H.; Chi, L. Growth of ultrathin organic semiconductor microstripes with thickness control in the monolayer precision. Angew. Chem. Int. Ed. 2013, 52, 12530–12535.

    Article  CAS  Google Scholar 

  23. Zhang, K.; Marszalek, T.; Wucher, P.; Wang, Z.; Veith, L.; Lu, H.; Räder, H. J.; Beaujuge, P. M.; Blom, P. W. M.; Pisula, W. Crystallization control of organic semiconductors during meniscus-guided coating by blending with polymer binder. Adv. Funct. Mater. 2018, 28, 1805594.

    Article  Google Scholar 

  24. Lee, S. B.; Lee, S.; Kim, D. G.; Kim, S. H.; Kang, B.; Cho, K. Solutalmarangoni-flow-mediated growth of patterned highly crystalline organic semiconductor thin film via gap-controlled bar coating. Adv. Funct. Mater. 2021, 31, 2100196.

    Article  CAS  Google Scholar 

  25. Liu, Z.; Li, Z.; Cai, Z.; Qiao, Y.; Yang, Y.; Chen, S.; Ma, X.; Li, H.; Meng, Q.; Zhang, F.; Song, Y. Vapor-induced marangoni coating for organic functional films. J. Mater. Chem. C 2021, 9, 17518–17525.

    Article  CAS  Google Scholar 

  26. Gu, X.; Shaw, L.; Gu, K.; Toney, M. F.; Bao, Z. The meniscus-guided deposition of semiconducting polymers. Nat. Commun. 2018, 9, 534.

    Article  PubMed  PubMed Central  Google Scholar 

  27. Chai, Z.; Abbasi, S. A.; Busnaina, A. A. Scalable directed assembly of highly crystalline 2,7-dioctyl[1]benzothieno[3,2-b][1]benzothiophene (C8-BTBT) films. ACS Appl. Mater. Interfaces 2018, 10, 18123–18130.

    Article  CAS  PubMed  Google Scholar 

  28. Yildiz, O.; Wang, Z.; Borkowski, M.; Fytas, G.; Blom, P. W. M.; Michels, J. J.; Pisula, W.; Marszalek, T. Optimized charge transport in molecular semiconductors by control of fluid dynamics and crystallization in meniscus-guided coating. Adv. Funct. Mater. 2022, 32, 2107976.

    Article  CAS  Google Scholar 

  29. Kang, S. H.; Shin, Y. C.; Hwang, E. Y.; Lee, J. H.; Kim, C.S.; Lin, Z.; Hur, S. H.; Han, D.-W.; Hong, S. W. Engineered “coffee-rings” of reduced graphene oxide as ultrathin contact guidance to enable patterning of living cells. Mater. Horiz. 2019, 6, 1066–1079.

    Article  CAS  Google Scholar 

  30. Chen, S.; Ma, X.; Cai, Z.; Long, H.; Wang, X.; Li, Z.; Qu, Z.; Zhang, F.; Qiao, Y.; Song, Y. A direct writing approach for organic semiconductor single-crystal patterns with unique orientation. Adv. Mater. 2022, 34, 2200928.

    Article  CAS  Google Scholar 

  31. Diao, Y.; Tee, B. C.; Giri, G.; Xu, J.; Kim, D. H.; Becerril, H. A.; Stoltenberg, R. M.; Lee, T. H.; Xue, G.; Mannsfeld, S. C.; Bao, Z. Solution coating of large-area organic semiconductor thin films with aligned single-crystalline domains. Nat. Mater. 2013, 12, 665–671.

    Article  CAS  PubMed  Google Scholar 

  32. Zhang, X.; Mao, J.; Deng, W.; Xu, X.; Huang, L.; Zhang, X.; Lee, S. T.; Jie, J. Precise patterning of laterally stacked organic microbelt heterojunction arrays by surface-energy-controlled stepwise crystallization for ambipolar organic field-effect transistors. Adv. Mater. 2018, 30, 1800187.

    Article  Google Scholar 

  33. Giri, G.; Park, S.; Vosgueritchian, M.; Shulaker, M. M.; Bao, Z. High-mobility, aligned crystalline domains of TIPS-pentacene with metastable polymorphs through lateral confinement of crystal growth. Adv. Mater. 2014, 26, 487–493.

    Article  CAS  PubMed  Google Scholar 

  34. Lu, Z.; Deng, W.; Fang, X.; Xiao, J.; Lu, B.; Zhang, X.; Pirzado, A. A. A.; Jie, J.; Zhang, X. Wafer-scale growth of aligned C60 single crystals via solution-phase epitaxy for high-performance transistors. Adv. Funct. Mater. 2021, 31, 2105459.

    Article  CAS  Google Scholar 

  35. Deng, W.; Zhang, X.; Dong, H.; Jie, J.; Xu, X.; Liu, J.; He, L.; Xu, L.; Hu, W.; Zhang, X. Channel-restricted meniscus self-assembly for uniformly aligned growth of single-crystal arrays of organic semiconductors. Mater. Today 2019, 24, 17–25.

    Article  CAS  Google Scholar 

  36. Zhao, Y.; Fan, X.; Feng, J.; Wang, X.; Wu, Y.; Su, B.; Jiang, L. Regulated dewetting for patterning organic single crystals with pure crystallographic orientation toward high performance field-effect transistors. Adv. Funct. Mater. 2018, 28, 1800470.

    Article  Google Scholar 

  37. Chen, S.; Liu, Z.; Long, H.; Yang, J.; Li, Z.; Cai, Z.; Qu, Z.; Shao, L.; Shi, X.; Jiang, L.; Xu, W.; Dong, H.; Wei, Z.; Qiao, Y.; Song, Y. A general vapor-induced coating approach for layer-controlled organic single crystals. Adv. Funct. Mater. 2023, DOI: https://doi.org/10.1002/adfm.202212158.

  38. Lee, J. C.; Seo, H.; Lee, M.; Kim, D.; Lee, H. S.; Park, H.; Ball, N.; Woo, J.; Kim, S. Y.; Nam, J.; Park, S. Investigation of the effect of 3D meniscus geometry on fluid dynamics and crystallization via in situ optical microscopy-assisted mathematical modeling. Adv. Mater. 2022, 34, 2105035.

    Article  CAS  Google Scholar 

  39. Huang, J.; Kim, F.; Tao, A. R.; Connor, S.; Yang, P. Spontaneous formation of nanoparticle stripe patterns through dewetting. Nat. Mater. 2005, 4, 896–900.

    Article  CAS  PubMed  Google Scholar 

  40. Corrales, T. P.; Bai, M.; Campo, V. D.; Homm, P; Ferrari, P.; Diama, A.; Wagner, C. Spontaneous formation of nanopatterns in velocity-dependent dip-coated organic films: From dragonflies to stripes. ACS Nano 2014, 8, 9954–9963.

    Article  CAS  PubMed  Google Scholar 

  41. Luo, J.; Wen, S.; Huang, P. Thin film lubrication part I: study on the transition between EHL and thin film lubrication using a relative optical interference intensity technique. Wear 1995, 194, 107–115.

    Article  Google Scholar 

  42. Guo, F.; Wong, P. L. A multi-beam intensity-based approach for lubricant film measurements in non-conformal contacts. Proc. Instn. Mech. Engrs 2002, 216, 281–291.

    Google Scholar 

  43. Goto, O.; Tomiya, S.; Murakami, Y.; Shinozaki, A.; Toda, A.; Kasahara, J.; Hobara, D. Organic single-crystal arrays from solution-phase growth using micropattern with nucleation control region. Adv. Mater. 2012, 24, 1117–1122.

    Article  CAS  PubMed  Google Scholar 

  44. Izawa, T.; Miyazaki, E.; Takimiya, K. Molecular ordering of high-performance soluble molecular semiconductors and reevaluation of their field-effect transistor characteristics. Adv. Mater. 2008, 20, 3388–3392.

    Article  CAS  Google Scholar 

  45. Uemura, T.; Hirose, Y.; Uno, M.; Takimiya, K.; Takeya, J. Very high mobility in solution-processed organic thin-film transistors of highly ordered [1]benzothieno[3,2-b]benzothiophene derivatives. Appl. Phys. Express 2009, 2, 111501.

    Article  Google Scholar 

  46. Feng, J.; Yan, X.; Liu, Y.; Gao, H.; Wu, Y.; Su, B.; Jiang, L. Crystallographically aligned perovskite structures for high-performance polarization-sensitive photodetectors. Adv. Mater. 2017, 29, 1605993.

    Article  Google Scholar 

  47. Hou, H. Y.; Tian, S.; Ge, H. R.; Chen, J. D.; Li, Y. Q.; Tang, J. X. Recent progress of polarization-sensitive perovskite photodetectors. Adv. Funct. Mater. 2022, 32, 2209324.

    Article  CAS  Google Scholar 

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Acknowledgments

This work was financially supported by the National Key R&D Program of China (Nos. 2018YFA0703200 and 2018YFA0208501), the National Natural Science Foundation of China (Nos. 22175185, 52003276, 52203247, 91963212 and 22002171), Beijing National Laboratory for Molecular Sciences (No. BNLMS-CXXM-202005) and CAS-VPST Silk Road Science Fund 2022 (No. 121111KYSB20210006). We thank Jiling Yue, Kaiang Liu and Bo Guan for the cryo-TEM measurements.

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Correspondence to Ya-Li Qiao or Yan-Lin Song.

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Shao, LJ., Chen, SN., Wang, YM. et al. Vapor-Induced Coating Method for Well-Aligned and Uniform Organic Semiconductor Single Crystals. Chin J Polym Sci 41, 1638–1645 (2023). https://doi.org/10.1007/s10118-023-2979-2

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  • DOI: https://doi.org/10.1007/s10118-023-2979-2

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