Citation: Ying Liu, Jia-Qing Zhao, Wen-Jian Sun, Yu-Kun Huang, Su-Jie Chen, Xiao-Jun Guo, Qing Zhang. A Facile Photo-cross-linking Method for Polymer Gate Dielectrics and Their Applications in Fully Solution Processed Low Voltage Organic Field-effect Transistors on Plastic Substrate[J]. Chinese Journal of Polymer Science, ;2018, 36(8): 918-924. doi: 10.1007/s10118-018-2110-2 shu

A Facile Photo-cross-linking Method for Polymer Gate Dielectrics and Their Applications in Fully Solution Processed Low Voltage Organic Field-effect Transistors on Plastic Substrate

Ying Liu ^1,T ,
Jia-Qing Zhao ^2,T ,
Wen-Jian Sun ¹ ,
Yu-Kun Huang ² ,
Su-Jie Chen ² ,
Xiao-Jun Guo ^2,, ,
Qing Zhang ^1,,

a.
Shanghai Key Laboratory of Electrical Insulation and Thermal Aging, Department of Polymer Science and Engineering, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China
b.
Department of Electronic Engineering, School of Electronic Information and Electrical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China

Corresponding author: Xiao-Jun Guo, x.guo@sjtu.edu.cn Qing Zhang, qz14@sjtu.edu.cn
Received Date: 19 December 2017
Accepted Date: 14 January 2018
Available Online: 9 March 2018

A simple and effective photochemical method was developed for cross-linking of polymer gate dielectrics. Laborious synthetic processes for functionalizing polymer dielectrics with photo-cross-linkable groups were avoided. The photo-cross-linker, BBP-4, was added into host polymers by simple solution blending process, which was capable of abstracting hydrogen atoms from polymers containing active C―H groups upon exposure to ultraviolet (UV) radiation. The cross-linking can be completed with a relatively long wavelength UV light (365 nm). The approach has been applied to methacrylate and styrenic polymers such as commercial poly(methylmethacrylate) (PMMA), poly(iso-butylmethacrylate) (PiBMA) and poly(4-methylstyrene) (PMS). The cross-linked networks enhanced dielectric properties and solvent resistance of the thin films. The bottom-gate organic field-effect transistors (OFETs) through all solution processes on plastic substrate were fabricated. The OFET devices showed low voltage operation and steep subthreshold swing at relatively small gate dielectric capacitance.
- Organic field-effect transistors,
- Solution processed,
- Polymer dielectric,
- Cross-linking,
- Photochemistry
1. [1]
  Rogers, J. A.; Someya, T.; Huang, Y. Materials and mechanics for stretchable electronics. Science 2017, 327, 1603−1607
2. [2]
  Tee, B. C. K.; Chortos, A.; Berndt, A.; KimNguyen, A.; Tom, A.; McGuire, A.; Lin, Z. C.; Tien, K.; Bae, W. G.; Wang, H.; Ping, M.; Chou, H. H.; Cui, B.; Deisseroth, K.; Ng, T.; Bao, Z. A skin-inspired organic digital mechanoreceptor. Science 2015, 350, 313−316 doi: 10.1126/science.aaa9306
3. [3]
  Di, C. A.; Zhang, F.; Zhu, D. Multi-functional integration of organic field-effect transistors (OFETs): advances and perspectives. Adv. Mater. 2013, 25, 313−330 doi: 10.1002/adma.201201502
4. [4]
  Liu, B.; Bao, Y.; Ling, H. F.; Zhu, W. S.; Gong, R. J.; Lin, J. Y.; Xie, L. H.; Yi, M. D.; Huang, W. Fluorinated p-n type copolyfluorene as polymer electret for stable nonvolatile organic transistor memory device. Chinese J. Polym. Sci. 2016, 34, 1183−1195 doi: 10.1007/s10118-016-1826-0
5. [5]
  Guo, X. J.; Xu, Y.; Ogier, S.; Ng, T. N.; Caironi, M.; Perinot, A.; Li, L.; Zhao, J. Q.; Tang, W.; Sporea, R. A.; Nejim, A.; Carrabina, J.; Cain, P.; Yan, F. Current status and opportunities of organic thin-film transistor technologies. IEEE Trans. Electron Devices 2017, 64, 1906−1921 doi: 10.1109/TED.2017.2677086
6. [6]
  Veres, J.; Ogier, S.; Lloyd, G.; de Leeuw, D. Gate insulators in organic field-effect transistors. Chem. Mater. 2004, 16, 4543−4555 doi: 10.1021/cm049598q
7. [7]
  Seong, H.; Baek, J.; Pak, K.; Im, S. G. A surface tailoring method of ultrathin polymer gate dielectrics for organic transistors: improved device performance and the thermal stability thereof. Adv. Funct. Mater. 2015, 25, 4462−4469 doi: 10.1002/adfm.v25.28
8. [8]
  Arias, A. C.; MacKenzie, J. D.; McCulloch, I.; Salleo, J. R. A. A. Materials and applications for large area electronics: solution-based approaches. Chem. Rev. 2010, 110, 3−24 doi: 10.1021/cr900150b
9. [9]
  Sun, J.; Zhang, B.; Katz, H. E. Materials for printable, transparent, and low-voltage transistors. Adv. Funct. Mater. 2011, 21, 29−45 doi: 10.1002/adfm.201001530
10. [10]
  Ortiz, R. P.; Facchetti, A.; Marks, T. J. High-k organic, inorganic, and hybrid dielectrics for low-voltage organic field-effect transistors. Chem. Rev. 2010, 110, 205−239 doi: 10.1021/cr9001275
11. [11]
  Cheng, X. Y.; Caironi, M.; Noh, Y. Y.; Wang, J. P.; Newman, C.; Yan, H.; Facchetti, A.; Sirringhaus, H. Air Stable cross-linked cytop ultrathin gate dielectric for high yield low-voltage top-gate organic field-effect transistors. Chem. Mater. 2010, 22, 1559−1566 doi: 10.1021/cm902929b
12. [12]
  Jung, S.; Albariqi, M.; Gruntz, G.; Al-Hathal, T.; Peinado, A.; Garcia-Caurel, E.; Nicolas, Y.; Toupance, T.; Bonnassieux, Y.; Horowitz, G. A TIPS-TPDO-tetraCN-Based n-type organic field-effect transistor with a cross-linked PMMA polymer gate dielectric. ACS Appl. Mater. Interfaces 2016, 8, 14701−14708 doi: 10.1021/acsami.6b00480
13. [13]
  Wang, C.; Lee, W. Y.; Nakajima, R.; Mei, J. G.; Kim, D. H.; Bao, Z. A. Thiol-ene cross-linked polymer gate dielectrics for low-voltage organic thin-film transistors. Chem. Mater. 2013, 25, 4806−4812 doi: 10.1021/cm403203k
14. [14]
  Li, Y.; Wang, H.; Zhang, C. Y.; Zhang, Y. C.; Cui, Z. C.; Yan, D. H.; Shi, Z. S. Organic thin-film transistors with novel high-k polymers as dielectric layers. Polym. Chem. 2015, 6, 3685−3693 doi: 10.1039/C5PY00221D
15. [15]
  Hung, C. C.; Wu, H. C.; Chiu, Y. C.; Tung, S. H.; Chen, W. C. Crosslinkable high dielectric constant polymer dielectrics for low voltage organic field-effect transistor memory devices. J. Polym. Sci., Part A: Polym. Chem. 2016, 54, 3224−3236 doi: 10.1002/pola.v54.19
16. [16]
  Kim, S. H.; Jang, M.; Kim, J.; Choi, H.; Baek, K. Y.; Park, C. E.; Yang, H. Complementary photo and temperature cured polymer dielectrics with high-quality dielectric properties for organic semiconductors. J. Mater. Chem. 2012, 22, 19940−19947 doi: 10.1039/c2jm33203e
17. [17]
  Lu, C.; Lee, W. Y.; Shih, C. C.; Wen, M. Y.; Chen, W. C. Stretchable polymer dielectrics for low-voltage-driven field-effect transistors. ACS Appl. Mater. Interfaces 2017, 9, 25522−25532 doi: 10.1021/acsami.7b06765
18. [18]
  Yoon, M. H.; Yan, H.; Facchetti, A.; Marks, T. J. Low-voltage organic field-effect transistors and inverters enabled by ultrathin cross-linked polymers as gate dielectrics. J. Am. Chem. Soc. 2005, 127, 10388−10395 doi: 10.1021/ja052488f
19. [19]
  Roberts, M. E.; Queralto, N.; Mannsfeld, S. C. B.; Reinecke, B. N.; Knoll, W.; Bao, Z. N. Cross-linked polymer gate dielectric films for low-voltage organic transistors. Chem. Mater. 2009, 21, 2292−2299 doi: 10.1021/cm900637p
20. [20]
  Han, H. J.; Zhang, S.; Sun, R. Y.; Wu, J. H.; Xie, M. R.; Liao, X. J. Photocrosslinkable polynorbornene-based block copolymers with enhanced dielectric and thermal properties. Chinese J. Polym. Sci. 2016, 34, 378−389 doi: 10.1007/s10118-016-1753-0
21. [21]
  Berndt, A.; Pospiech, D.; Jehnichen, D.; Haussler, L.; Voit, B.; Al-Hussein, M.; Plotner, M.; Kumar, A.; Fischer, W. J. Methacrylate copolymers with liquid crystalline side chains for organic gate dielectric applications. ACS Appl. Mater. Interfaces 2015, 7, 12339−12347 doi: 10.1021/am5069479
22. [22]
  Lee, T. W.; Shin, J. H.; Kang, I. N.; Lee, S. Y. photocurable organic gate insulator for the fabrication of high-field effect mobility organic transistors by low temperature and solution processing. Adv. Mater. 2007, 19, 2702−2706 doi: 10.1002/(ISSN)1521-4095
23. [23]
  Jang, J.; Kim, S. H.; Hwang, J.; Nam, S.; Yang, C.; Chung, D. S.; Park, C. E. Photopatternable ultrathin gate dielectrics for low-voltage-operating organic circuits. Appl. Phys. Lett. 2009, 95, 073302 doi: 10.1063/1.3206665
24. [24]
  Lee, E. K.; Kim, J. Y.; Chung, J. W.; Lee, B. L.; Kang, Y. Photo-crosslinkable polymer gate dielectrics for hysteresis-free organic field-effect transistors with high solvent resistance. RSC Adv. 2014, 4, 293−300 doi: 10.1039/C3RA43890B
25. [25]
  Kim, Y.; Roh, J.; Kim, J. H.; Kang, C. M.; Kang, I. N.; Jung, B. J.; Lee, C.; Hwang, D. H. Photocurable propyl-cinnamate-functionalized polyhedral oligomeric silsesquioxane as a gate dielectric for organic thin film transistors. Org. Electron. 2013, 14, 2315−2323 doi: 10.1016/j.orgel.2013.05.030
26. [26]
  de Col, C.; Nawaz, A.; Cruz-Cruz, I.; Kumar, A.; Kumar, A.; Hümmelgen, I. A. Poly(vinyl alcohol) gate dielectric surface treatment with vitamin C for poly(3-hexylthiophene-2,5-diyl) based field effect transistors performance improvement. Org. Electron. 2015, 17, 22−27 doi: 10.1016/j.orgel.2014.11.015
27. [27]
  Kim, S. H.; Hong, K.; Jang, M.; Jang, J.; Anthony, J. E.; Yang, H.; Park, C. E. Photo-curable polymer blend dielectrics for advancing organic field-effect transistor applications. Adv. Mater. 2010, 22, 4809−4813 doi: 10.1002/adma.201000904
28. [28]
  Jang, J.; Nam, S.; Hwang, J.; Park, J. J.; Im, J.; Park, C. E.; Kim, J. M. Photocurable polymer gate dielectrics for cylindrical organic field-effect transistors with high bending stability. J. Mater. Chem. 2012, 22, 1054−1060 doi: 10.1039/C1JM14091D
29. [29]
  Carbone, N. D.; Ene, M.; Lancaster, J. R.; Koberstein, J. T. Kinetics and mechanisms of radical-based branching/cross-linking reactions in preformed polymers induced by benzophenone and bis-benzophenone photoinitiators. Macromolecules 2013, 46, 5434−5444 doi: 10.1021/ma4007347
30. [30]
  Katzenstein, J. M.; Kim, C. B.; Prisco, N. A.; Katsumata, R.; Li, Z.; Janes, D. W.; Blachut, G.; Ellison, C. J. A Photochemical approach to directing flow and stabilizing topography in polymer films. Macromolecules 2014, 47, 6804−6812 doi: 10.1021/ma5010698
31. [31]
  Carroll, G. T.; Sojka, M. E.; Lei, X.; Turro, N. J.; Koberstein, J. T. Photoactive additives for cross-linking polymer films: inhibition of dewetting in thin polymer films. Langmuir 2006, 22, 7748−7754 doi: 10.1021/la0611099
32. [32]
  Czech, Z.; Kowalczyk, A.; Kabatc, J.; Swiderska, J. Photoreactive UV-crosslinkable solvent-free acrylic pressure-sensitive adhesives containing copolymerizable photoinitiators based on benzophenones. Eur. Polym. J. 2012, 48, 1446−1454 doi: 10.1016/j.eurpolymj.2012.05.010
33. [33]
  Jang, J. Y.; Kim, S. H.; Nam, S.; Chung, D. S.; Yang, C. W.; Yun, W. M.; Park, C. E.; Koo, J. B. Hysteresis-free organic field-effect transistors and inverters using photocrosslinkable poly(vinyl cinnamate) as a gate dielectric. Appl. Phys. Lett. 2008, 92, 143306 doi: 10.1063/1.2907974
34. [34]
  Li, Y.; Wang, H.; Zhang, X.; Zhang, Q.; Wang, X.; Cao, D.; Shi, Z.; Yan, D.; Cui, Z. Organic thin film transistors with novel photosensitive polyurethane as dielectric layer. RSC Adv. 2016, 6, 5377−5383 doi: 10.1039/C5RA22970G
35. [35]
  Kalb, W. L.; Batlogg, B. Calculating the trap density of states in organic field-effect transistors from experiment: A comparison of different methods. Phys. Rev. B 2010, 81, 035327 doi: 10.1103/PhysRevB.81.035327
36. [36]
  Raghuwanshi, V.; Bharti, D.; Varun, I.; Mahato, A. K.; Tiwari, S. P. Performance enhancement in mechanically stable flexible organic-field effect transistors with TIPS-pentacene:polymer blend. Org. Electron. 2016, 34, 284−288 doi: 10.1016/j.orgel.2016.04.039
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