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
1. [1]
  Min Chen , Boyu Peng , Xuyun Guo , Ye Zhu , Hanying Li . Polyethylene interfacial dielectric layer for organic semiconductor single crystal based field-effect transistors. Chinese Chemical Letters, 2024, 35(4): 109051-. doi: 10.1016/j.cclet.2023.109051
2. [2]
  Zhiwei Zhong , Yanbin Huang , Wantai Yang . A simple photochemical method for surface fluorination using perfluoroketones. Chinese Chemical Letters, 2024, 35(5): 109339-. doi: 10.1016/j.cclet.2023.109339
3. [3]
  Zhixiang Li , Zhirong Yang , Chang Yao , Bin Wu , Gang Qian , Xuezhi Duan , Xinggui Zhou , Jing Zhang . Efficient continuous synthesis of 2-hydroxycarbazole and 4-hydroxycarbazole in a millimeter scale photoreactor. Chinese Chemical Letters, 2024, 35(4): 108893-. doi: 10.1016/j.cclet.2023.108893
4. [4]
  Yi Liu , Peng Lei , Yang Feng , Shiwei Fu , Xiaoqing Liu , Siqi Zhang , Bin Tu , Chen Chen , Yifan Li , Lei Wang , Qing-Dao Zeng . Topologically engineering of π-conjugated macrocycles: Tunable emission and photochemical reaction toward multi-cyclic polymers. Chinese Chemical Letters, 2024, 35(10): 109571-. doi: 10.1016/j.cclet.2024.109571
5. [5]
  Jing-Jing Zhang , Lujun Lou , Rui Lv , Jiahui Chen , Yinlong Li , Guangwei Wu , Lingchao Cai , Steven H. Liang , Zhen Chen . Recent advances in photochemistry for positron emission tomography imaging. Chinese Chemical Letters, 2024, 35(8): 109342-. doi: 10.1016/j.cclet.2023.109342
6. [6]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
7. [7]
  Wanmin Cheng , Juan Du , Peiwen Liu , Yiyun Jiang , Hong Jiang . Photoinitiated Grignard Reagent Synthesis and Experimental Improvement in Triphenylmethanol Preparation. University Chemistry, 2024, 39(5): 238-242. doi: 10.3866/PKU.DXHX202311066
8. [8]
  Fei Liu , Dong-Yang Zhao , Kai Sun , Ting-Ting Yu , Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047
9. [9]
  Zhaohong Chen , Mengzhen Li , Jinfei Lan , Shengqian Hu , Xiaogang Chen . Organic ferroelastic enantiomers with high T_c and large dielectric switching ratio triggered by order-disorder and displacive phase transition. Chinese Chemical Letters, 2024, 35(10): 109548-. doi: 10.1016/j.cclet.2024.109548
10. [10]
  Jing Wang , Zhongliao Wang , Jinfeng Zhang , Kai Dai . Single-layer crystalline triazine-based organic framework photocatalysts with different linking groups for H2O2 production. Chinese Journal of Structural Chemistry, 2023, 42(12): 100202-100202. doi: 10.1016/j.cjsc.2023.100202
11. [11]
  Yuanzhe Lu , Yuanqin Zhu , Linfeng Zhong , Dingshan Yu . Long-lifespan aqueous alkaline and acidic batteries enabled by redox conjugated covalent organic polymer anodes. Chinese Journal of Structural Chemistry, 2024, 43(3): 100249-100249. doi: 10.1016/j.cjsc.2024.100249
12. [12]
  Zihao Wang , Jing Xue , Zhicui Song , Jianxiong Xing , Aijun Zhou , Jianmin Ma , Jingze Li . Li-Zn alloy patch for defect-free polymer interface film enables excellent protection effect towards stable Li metal anode. Chinese Chemical Letters, 2024, 35(10): 109489-. doi: 10.1016/j.cclet.2024.109489
13. [13]
  Panke Zhou , Hong Yu , Mun Yin Chee , Tao Zeng , Tianli Jin , Hongling Yu , Shuo Wu , Wen Siang Lew , Xiong Chen . Electron push-pull effects induced performance promotion in covalent organic polymer thin films-based memristor for neuromorphic application. Chinese Chemical Letters, 2024, 35(5): 109279-. doi: 10.1016/j.cclet.2023.109279
14. [14]
  Jun Guo , Zhenbang Zhuang , Wanqiang Liu , Gang Huang . "Co-coordination force" assisted rigid-flexible coupling crystalline polymer for high-performance aqueous zinc-organic batteries. Chinese Chemical Letters, 2024, 35(9): 109803-. doi: 10.1016/j.cclet.2024.109803
15. [15]
  Linshan Peng , Qihang Peng , Tianxiang Jin , Zhirong Liu , Yong Qian . Highly efficient capture of thorium ion by citric acid-modified chitosan gels from aqueous solution. Chinese Chemical Letters, 2024, 35(5): 108891-. doi: 10.1016/j.cclet.2023.108891
16. [16]
  Xiaobo Li , Qunyan Wu , Congzhi Wang , Jianhui Lan , Meng Zhang , Weiqun Shi . Theoretical perspectives on the reduction of Pu(Ⅳ) and Np(Ⅵ) by methylhydrazine in HNO₃ solution: Implications for Np/Pu separation. Chinese Chemical Letters, 2024, 35(7): 109359-. doi: 10.1016/j.cclet.2023.109359
17. [17]
  Zheng Zhao , Ben Zhong Tang . An efficient strategy enabling solution processable thermally activated delayed fluorescence emitter with high horizontal dipole orientation. Chinese Journal of Structural Chemistry, 2024, 43(6): 100270-100270. doi: 10.1016/j.cjsc.2024.100270
18. [18]
  Tian Yang , Yi Liu , Lina Hua , Yaoyao Chen , Wuqian Guo , Haojie Xu , Xi Zeng , Changhao Gao , Wenjing Li , Junhua Luo , Zhihua Sun . Lead-free hybrid two-dimensional double perovskite with switchable dielectric phase transition. Chinese Chemical Letters, 2024, 35(6): 108707-. doi: 10.1016/j.cclet.2023.108707
19. [19]
  Xiao-Tong Sun , Hao-Fei Ni , Yi Zhang , Da-Wei Fu . Hybrid perovskite shows temperature-dependent photoluminescence and dielectric response triggered by halogen substitution. Chinese Journal of Structural Chemistry, 2024, 43(6): 100212-100212. doi: 10.1016/j.cjsc.2024.100212
20. [20]
  Tiankai Sun , Hui Min , Zongsu Han , Liang Wang , Peng Cheng , Wei Shi . Rapid detection of nanoplastic particles by a luminescent Tb-based coordination polymer. Chinese Chemical Letters, 2024, 35(5): 108718-. doi: 10.1016/j.cclet.2023.108718

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(628)
HTML views(2)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142