journal article·2025-01Open access

Post‐Polymerization Strategy via Dual Site Clicking for Synthesizing Intrinsically Cross‐Linkable Semiconducting Polymers

Jaehoon Lee, Seungju Kang, Eunsoo Lee, Jiyun Lee, Tae Woong Yoon, Min‐Jae Kim, Yongjoon Cho, Mingfei Xiao, Yorrick Boeije, Wenjin Zhu, Changduk Yang, Jin‐Wook Lee, Sungjoo Lee, Guobing Zhang, Henning Sirringhaus, Boseok Kang

EcoMat· Volume 7· Issue 1

Abstract

ABSTRACT Crosslinked organic semiconductors have opened the way for various fabrication techniques in the field of organic electronics owing to their three‐dimensional network structure with high solvent resistivity. However, recent efforts to synthesize cross‐linkable semiconducting polymers have been limited by their low molecular weights and yields. In this study, this limitation is overcome by a novel post‐polymerization strategy. A reagent with a cross‐linkable functional group, (3‐mercaptopropyl)trimethoxysilane, is attached to a diketopyrrolopyrrole‐based donor–acceptor copolymer (DPPTT) via thioesterification and para‐fluoro‐thiol reaction, modifying two sites simultaneously. This modification preserves the molecular weight and electrical properties of the original polymers. In addition, the use of click chemistry enables high yield (98%) without any purification. The modified DPPTT demonstrated high resistance to organic solvents (80% retention dipped in 1‐chlorobenzene for 1 h). Exploiting this benefit, an ultrathin flexible array of 100 organic field‐effect transistors fabricated using conventional photolithography showed high‐performance reliability. Thus, this study provides a universal strategy to synthesize versatile polymer semiconductors for practical organic electronics. image
Source: crossref · Quality: baseline

Research context

OpenAlex topics: Conducting polymers and applications · Organic Electronics and Photovoltaics · Advanced Sensor and Energy Harvesting Materials

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

SKKU Advanced Institute of Nanotechnology (SAINT) and Department of Nano Science and Technology Sungkyunkwan University Suwon Korea

School of Energy and Chemical Engineering, Perovtronics Research Center, Low Dimensional Carbon Materials Center Ulsan National Institute of Science and Technology (UNIST) Ulsan South Korea

Department of Instrument Science and Technology, School of Mechanical Science and Engineering Huazhong University of Science and Technology Wuhan China

State Key Laboratory of Intelligent Manufacturing Equipment and Technology Huazhong University of Science and Technology Wuhan China

Optoelectronics Group, Cavendish Laboratory University of Cambridge Cambridge UK

Department of Physics, Cavendish Laboratory University of Cambridge Cambridge UK

Department of Nano Engineering Sungkyunkwan University Suwon Korea

Special Display and Imaging Technology Innovation Center of Anhui Province, State Key Laboratory of Advanced Display Technology, Academy of Opto‐Electronic Technology Hefei University of Technology Hefei P. R. China

School of Chemistry and Chemical Engineering, Key Laboratory of Advanced Functional Materials and Devices of Anhui Province Hefei University of Technology Hefei P. R. China

Department of Semiconductor Convergence Engineering Sungkyunkwan University Suwon Korea

Funding

National Research Foundation of Korea

References (62)

Show source-provided references
1. 10.1021/acs.jpcc.8b0498110.1021/acs.jpcc.8b04981 ↗
2. 10.1039/c9ee01935a10.1039/c9ee01935a ↗
3. 10.1016/j.cej.2023.14412910.1016/j.cej.2023.144129 ↗
4. 10.1021/acsami.9b2331810.1021/acsami.9b23318 ↗
5. 10.1038/s41467‐021‐23798‐210.1038/s41467‐021‐23798‐2 ↗
6. 10.1126/sciadv.aav309710.1126/sciadv.aav3097 ↗
7. 10.1002/marc.20150032410.1002/marc.201500324 ↗
8. 10.1002/admt.20200085710.1002/admt.202000857 ↗
9. 10.1002/pola.2427910.1002/pola.24279 ↗
10. 10.1021/acs.chemmater.8b0208510.1021/acs.chemmater.8b02085 ↗
11. 10.1016/j.dyepig.2018.06.01810.1016/j.dyepig.2018.06.018 ↗
12. 10.1002/adfm.20201097910.1002/adfm.202010979 ↗
13. 10.1002/adfm.20210019610.1002/adfm.202100196 ↗
14. 10.1039/c9py01469a10.1039/c9py01469a ↗
15. 10.1021/acsaelm.3c0037310.1021/acsaelm.3c00373 ↗
16. 10.1021/ma502289n10.1021/ma502289n ↗
17. 10.1021/acs.chemrev.8b0006310.1021/acs.chemrev.8b00063 ↗
18. 10.1021/acsami.0c0435610.1021/acsami.0c04356 ↗
19. 10.1002/adfm.20221212710.1002/adfm.202212127 ↗
20. 10.1016/j.apsusc.2019.02.10610.1016/j.apsusc.2019.02.106 ↗
21. 10.1002/adfm.20160260310.1002/adfm.201602603 ↗
22. 10.1038/s41467‐020‐15181‐410.1038/s41467‐020‐15181‐4 ↗
23. 10.1002/admi.20220205310.1002/admi.202202053 ↗
24. 10.1021/acs.chemmater.8b0431410.1021/acs.chemmater.8b04314 ↗
25. 10.3390/molecules2504100910.3390/molecules25041009 ↗
26. 10.1039/c6ta01450j10.1039/c6ta01450j ↗
27. 10.1021/acs.macromol.6b0021810.1021/acs.macromol.6b00218 ↗
28. 10.1021/ja403949g10.1021/ja403949g ↗
29. 10.1098/rsos.17202510.1098/rsos.172025 ↗
30. 10.1002/adom.20230098810.1002/adom.202300988 ↗
31. 10.1039/d2mh00519k10.1039/d2mh00519k ↗
32. 10.1002/ange.20230384110.1002/ange.202303841 ↗
33. 10.1002/anie.20221926210.1002/anie.202219262 ↗
34. 10.1557/s43578‐023‐01250‐z10.1557/s43578‐023‐01250‐z ↗
35. 10.1016/j.cplett.2020.13750710.1016/j.cplett.2020.137507 ↗
36. 10.1021/acs.macromol.2c0014310.1021/acs.macromol.2c00143 ↗
37. 10.1002/chem.20190129010.1002/chem.201901290 ↗
38. 10.1039/c6sc04427a10.1039/c6sc04427a ↗
39. 10.1039/c9nj01748h10.1039/c9nj01748h ↗
40. 10.1039/c7py00812k10.1039/c7py00812k ↗
41. 10.1039/c8py00287h10.1039/c8py00287h ↗
42. 10.3390/polym1516339210.3390/polym15163392 ↗
43. 10.1002/adma.20120179510.1002/adma.201201795 ↗
44. 10.1016/j.polymer.2016.09.07210.1016/j.polymer.2016.09.072 ↗
45. 10.1364/ol.5.00037710.1364/ol.5.000377 ↗
46. 10.1002/adma.20130306010.1002/adma.201303060 ↗
47. 10.1038/nature1385410.1038/nature13854 ↗
48. 10.1002/adfm.20190454510.1002/adfm.201904545 ↗
49. 10.1021/cr050154310.1021/cr0501543 ↗
50. 10.1021/acsami.6b0999310.1021/acsami.6b09993 ↗
51. 10.1007/s10118‐023‐2943‐110.1007/s10118‐023‐2943‐1 ↗
52. 10.1021/cm203058p10.1021/cm203058p ↗
53. 10.1039/C5PY01669J10.1039/C5PY01669J ↗
54. 10.1039/c5tc04151a10.1039/c5tc04151a ↗
55. 10.1016/j.apsusc.2022.15428210.1016/j.apsusc.2022.154282 ↗
56. 10.1016/j.cej.2023.14388710.1016/j.cej.2023.143887 ↗
57. 10.1021/jacs.1c1011910.1021/jacs.1c10119 ↗
58. 10.1002/adma.20090113610.1002/adma.200901136 ↗
59. 10.1016/j.orgel.2005.10.00210.1016/j.orgel.2005.10.002 ↗
60. 10.1002/adfm.20100043610.1002/adfm.201000436 ↗
61. 10.1002/adfm.20190459010.1002/adfm.201904590 ↗
62. 10.1016/j.orgel.2008.02.01510.1016/j.orgel.2008.02.015 ↗