核扩展的萘二酰亚胺-插烯四硫富瓦烯类双极性有机半导体

doi:10.6023/cjoc202404033

有机化学 ›› 2024, Vol. 44 ›› Issue (9): 2810-2819.DOI: 10.6023/cjoc202404033 上一篇下一篇

研究论文

核扩展的萘二酰亚胺-插烯四硫富瓦烯类双极性有机半导体

张瑞^a^,^b, 何萌萌^b^,^c, 向焌钧^b, 蔡莎莉^b, 葛从伍^b^,^*(), 高希珂^b^,^*()

a 中国科学技术大学化学与材料科学学院合肥 230026
b 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032
c 四川师范大学化学与材料科学学院成都 610066

收稿日期:2024-04-22 修回日期:2024-05-23 发布日期:2024-05-28
通讯作者: 葛从伍, 高希珂
作者简介:
^†共同第一作者.
基金资助:
国家自然科学基金(22225506); 中国科学院战略性先导科技专项B类(XDB0520101); 上海市启明星计划(21QA1411100); 中国科学院青年创新促进会(2022252)

Core-Expanded Naphthalene Diimides-Vinylogous Tetrathia-fulvalenes toward Ambipolar Organic Semiconductors

Rui Zhang^a^,^b, Mengmeng He^b^,^c, Junjun Xiang^b, Shali Cai^b, Congwu Ge^b(), Xike Gao^b()

a School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
c College of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610066

Received:2024-04-22 Revised:2024-05-23 Published:2024-05-28
Contact: Congwu Ge, Xike Gao
About author:
^†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22225506); Strategic Priority Research Program of the Chinese Academy of Sciences(XDB0520101); Shanghai Rising-Star Program(21QA1411100); Youth Innovation Promotion Association CAS(2022252)

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摘要/Abstract

与p-型和n-型有机半导体相结合的方法相比, 双极性有机半导体在构筑逻辑互补电路方面具有明显优势, 然而,目前综合性能优良的双极性有机半导体仍较为缺乏. 通过能级调控策略, 设计合成了五个苯并六元氮/氧/硫杂环核扩展的萘二酰亚胺-插烯四硫富瓦烯(NDI-VTTF)衍生物1~5, 并对其底栅顶接触结构的有机场效应晶体管(OFET)器件性能进行了研究. 结果表明化合物1~5均具有双极性载流子传输特性, 其中化合物1, 3~5是电子传输主导的双极性有机半导体, 而化合物2是电子和空穴传输性能平衡的双极性有机半导体. 得益于热退火处理对薄膜结晶性的提高和微观形貌的改善, 基于化合物1~5的薄膜OFET器件的迁移率均随热退火温度的升高而增大, 其中基于化合物2的薄膜OFET器件经180 ℃热退火后的电子和空穴迁移率分别达到0.037和0.050 cm²•V^－1•s^－1.

关键词: 逻辑互补电路, 有机场效应晶体管, 双极性有机半导体, 萘二酰亚胺-插烯四硫富瓦烯, 核扩展, 能级调控

In comparison with the combination of p- and n-type organic semiconductors, the way to construct logic comple- mentary circuits by ambipolar organic semiconductors has obvious advantages. However, so far, the ambipolar ones with high performance are still scarce. In this work, a series of benzo six-membered nitrogen/oxygen/sulfur heterocycles core-substituted naphthalene diimides-vinylogous tetrathiafulvalene (NDI-VTTF) derivatives 1~5 were designed by energy level regulation strategy. Subsequently, bottom-gate and top-contact organic field-effect transistors (OFETs) based on compounds 1~5 were fabricated and systematically studied. The results showed that all the OFET devices exhibit ambipolar semiconducting behaviors, among them the OFET devices based on compounds 1, 3~5 displayed electron-dominated ambipolar charge transport characteristics, while the devices based on compound 2 showed balanced ambipolar charge transport features. Due to the improvement of thin-film crystallinity and morphology by thermal annealing treatment, the performance of OFETs based on compounds 1~5 was improved with the increase of thermal annealing temperature. When thermal annealed at 180 ℃, OFETs based on compound 2 showed the balanced electron and hole mobilities of up to 0.037 and 0.050 cm²•V^－1•s^－1, respectively.

Key words: logic complementary circuits, organic field-effect transistors, ambipolar organic semiconductors, naphthalene diimides-vinylogous tetrathiafulvalenes, core-substituted, energy level regulation

引用此文

张瑞, 何萌萌, 向焌钧, 蔡莎莉, 葛从伍, 高希珂. 核扩展的萘二酰亚胺-插烯四硫富瓦烯类双极性有机半导体[J]. 有机化学, 2024, 44(9): 2810-2819.

Rui Zhang, Mengmeng He, Junjun Xiang, Shali Cai, Congwu Ge, Xike Gao. Core-Expanded Naphthalene Diimides-Vinylogous Tetrathia-fulvalenes toward Ambipolar Organic Semiconductors[J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2810-2819.

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[1]	(a) Crone, B.; Dodabalapur, A.; Lin, Y. Y.; Filas, R. W.; Bao, Z.; LaDuca, A.; Sarpeshkar, R.; Katz, H. E.; Li, W. Nature 2000, 403, 521.
	(b) Liu, K.; Ouyang, B.; Guo, X. J.; Guo, Y. L.; Liu, Y. Q. npj Flexible Electron. 2022, 6, 1.
	(c) Liu, H. R.; Liu, D.; Yang, J. C.; Gao, H. F.; Wu, Y. C. Small 2023, 19, 2206938.
	(d) Watanabe, K.; Miura, N.; Taguchi, H.; Komatsu, T.; Aratake, A.; Makita, T.; Tanabe, M.; Wakimoto, T.; Kumagai, S.; Okamoto, T.; Watanabe, S.; Takeya, J. Adv. Mater. Technol. 2024, 9, 2301673.
	(e) Zeng, W.-J.; Zhou, X.-Y.; Pan, X.-J.; Song, C.-L.; Zhang, H.-L. AIP Adv. 2013, 3, 012101.
[2]	(a) Higashino, T.; Mori, T. Phys. Chem. Chem. Phys. 2022, 24, 9770.
	(b) Zhang, Y. H.; Wang, Y. S.; Gao, C.; Ni, Z. J.; Zhang, X. T.; Hu, W. P.; Dong, H. L. Chem. Soc. Rev. 2023, 52, 1331.
[3]	(a) Kobaisi, M. A.; Bhosale, S. V.; Latham, K.; Raynor, A. M.; Bhosale, S. V. Chem. Rev. 2016, 116, 11685. pmid: 30675934
	(b) Takimiya, K.; Nakano, M. Bull. Chem. Soc. Jpn 2018, 91, 121. pmid: 30675934
	(c) Shukla, J.; Mukhopadhyay, P. Eur. J. Org. Chem. 2019, 7770. pmid: 30675934
	(d) Insuasty, A.; Maniam, S.; Langford, S. J. Chem.-Eur. J. 2019, 25, 7058. doi: 10.1002/chem.201806009 pmid: 30675934
	(e) Zhang, C.; Wang, Z. R.; Li, H.; Lu, J. M.; Zhang, Q. C. Org. Chem. Front. 2020, 7, 3001. pmid: 30675934
	(f) Bhosale, S. V.; Kobaisi, M. A.; Jadhav, R. W.; Morajkar, P. P.; Jones, L. A.; George, S. Chem. Soc. Rev. 2021, 50, 9845. pmid: 30675934
[4]	Luo, H. W.; Cai, Z. X.; Tan, L. X.; Guo, Y. L.; Yang, G.; Liu, Z. T.; Zhang, G. X.; Zhang, D. Q.; Xu, W.; Liu, Y. Q. J. Mater. Chem. C 2013, 1, 2688.
[5]	Hu, J. Y.; Nakano, M.; Osaka, I.; Takimiya, K. J. Mater. Chem. C 2015, 3, 4244.
[6]	Cui, X. P.; Xiao, C. Y.; Winands, T.; Koch, T.; Li, Y.; Zhang, L.; Doltsinis, N. L.; Wang, Z. H. J. Am. Chem. Soc. 2018, 140, 12175.
[7]	Hu, Y. B.; Wang, Z. L.; Zhang, X.; Yang, X. D.; Ge, C. W.; Fu, L. N.; Gao, X. K. Org. Lett. 2017, 19, 468.
[8]	((a) Zhou, M.; Li, J.; Cheng, J.; Ge, C. W.; Cheng, T. Y.; Gao, X. K. Chin. J. Org. Chem. 2021, 41, 4400 (in Chinese).
	(周敏, 李晶, 程杰, 葛从伍, 程探宇, 高希珂, 有机化学, 2021, 41, 4400.) doi: 10.6023/cjoc202105023
	(b) Zhao, B.; Li, C.-Z.; Liu, S.-Q.; Richards, J. J.; Chueh, C.-C.; Ding, F. Z.; Pozzo, L. D.; Li, X. S.; Jen, A. K. Y. J. Mater. Chem. A 2015, 3, 6929.
	(c) Gao, X. K.; Di, C.-A.; Hu, Y. B.; Yang, X. D.; Fan, H. Y.; Zhang, F.; Liu, Y. Q.; Li, H. Q.; Zhu, D. B. J. Am. Chem. Soc. 2010, 132, 3697.
	(d) Henriksen, L. Acta Chem. Scand. 1996, 50, 432.
[9]	Azumi, R.; Götz, G.; Bäuerle, P. Synth. Met. 1999, 101, 544.
[10]	Ohtsuka, N.; Nakano, M.; Nakagawa, S.; Shahiduzzaman, M.; Karakawa, M.; Taima, T.; Minoura, M. Chem. Commun. 2020, 56, 12343.
[11]	Cai, K.; Xie, J. J.; Yang, X.; Zhao, D. H. Org. Lett. 2014, 16, 1852.
[12]	Mishra, A.; Behera, R. K.; Behera, P. K.; Mishra, B. K.; Behera, G. B. Chem. Rev. 2000, 100, 1973. doi: 10.1021/cr990402t pmid: 11749281
[13]	Dou, L. T.; Liu, Y. S.; Hong, Z. R.; Li, G.; Yang, Y. Chem. Rev. 2015, 115, 12633.
[14]	Cardona, C. M.; Li, W.; Kaifer, A. E.; Stockdale, D.; Bazan, G. C. Adv. Mater. 2011, 23, 2367.
[15]	(a) Cameron, J.; Kanibolotsky, A. L.; Skabara, P. J. Adv. Mater. 2023, 2302259. pmid: 29420879
	(b) Gleiter, R.; Haberhauer, G.; Werz, D. B.; Rominger, F.; Bleiholder, C. Chem. Rev. 2018, 118, 2010. doi: 10.1021/acs.chemrev.7b00449 pmid: 29420879
	(c) Xie, J. J.; Shi, K.; Cai, K.; Zhang, D.; Wang, J.-Y.; Pei, J.; Zhao, D. H. Chem. Sci. 2016, 7, 499. pmid: 29420879
	(d) Han, W. J.; Wang, Z. L.; Hu, Y. B.; Yang, X. D.; Ge, C. W.; Gao, X. K. Sci. China Chem. 2020, 63, 1182. pmid: 29420879
[16]	(a) Hu, Y. B.; Gao, X. K.; Di, C.-A.; Yang, X. D.; Zhang, F.; Liu, Y. Q.; Li, H. X.; Zhu, D. B. Chem. Mater. 2011, 23, 1204.
	(b) Chen, X.; Guo, Y. L.; Tan, L. X.; Yang, G.; Li, Y. H.; Zhang, G. X.; Liu, Z. T.; Xu, W.; Zhang, D. Q. J. Mater. Chem. C 2013, 1, 1087.
	(c) Zhou, Q.; Yang, J. F.; Du, M. X.; Yu, X. B.; Li, C.; Zhang, X.-S.; Peng, Q.; Zhang, G. X.; Zhang, D. Q. J. Mater. Chem. C 2022, 10, 2814.
[17]	(a) Shukla, D.; Nelson, S. F.; Freeman, D. C.; Rajeswaran, M.; Ahearn, W. G.; Meyer, D. M.; Carey, J. T. Chem. Mater. 2008, 20, 7486.
	(b) Ichikawa, M.; Yokota, Y.; Jeon, H.-G.; Banoukepa, G. d. R.; Hirata, N.; Oguma, N. Org. Electron. 2013, 14, 516.
	(c) Welford, A.; Maniam, S.; Gann, E.; Jiao, X. C.; Thomsen, L.; Langford, S. J.; McNeill, C. R. Org. Electron. 2019, 75, 105378.
[18]	Röger, C.; Würthner, F. J. Org. Chem. 2007, 72, 8070.

Compound	λ_max/nm		E_g^opt/eV^b	E_LUMO/eV^c	E_HOMO/eV^c	E_HOMO/eV^d	E_LUMO/eV^e	E_HOMO/eV^e
Compound	Solution^a	Film	E_g^opt/eV^b	E_LUMO/eV^c	E_HOMO/eV^c	E_HOMO/eV^d	E_LUMO/eV^e	E_HOMO/eV^e
1	701	731	1.48	－4.08	－5.63	－5.56	－3.36	－5.40
2	662	684	1.60	－3.84	－5.46	－5.44	－3.06	－5.15
3	628	651	1.60	－4.21	—	－5.81	－3.55	－5.77
4	644	662	1.66	－4.02	－5.71	－5.68	－3.28	－5.47
5	576	586	1.67	－4.17	—	－5.84	－3.47	－5.82

Compound	λ_max/nm		E_g^opt/eV^b	E_LUMO/eV^c	E_HOMO/eV^c	E_HOMO/eV^d	E_LUMO/eV^e	E_HOMO/eV^e
Compound	Solution^a	Film	E_g^opt/eV^b	E_LUMO/eV^c	E_HOMO/eV^c	E_HOMO/eV^d	E_LUMO/eV^e	E_HOMO/eV^e
1	701	731	1.48	－4.08	－5.63	－5.56	－3.36	－5.40
2	662	684	1.60	－3.84	－5.46	－5.44	－3.06	－5.15
3	628	651	1.60	－4.21	—	－5.81	－3.55	－5.77
4	644	662	1.66	－4.02	－5.71	－5.68	－3.28	－5.47
5	576	586	1.67	－4.17	—	－5.84	－3.47	－5.82

Compound	T_a/℃	μ_e,ave (μ_e,max)/(cm²•V^－1•s^－1)	V_T,ave (V_T,min)/V	I_on/I_off	μ_h,ave (μ_h,max)/(cm²•V^－1•s^－1)	V_T,ave (V_T,min)/V	I_on/I_off
1	As-spun	2.8×10^－3 (3.4×10^－3)	25.2 (20.1)	10³~10⁴	—	—	—
	60	0.017 (0.022)	17.2 (7.9)	10³~10⁴	3.6×10^－4 (3.9×10^－4)	－30.6 (－24.6)	10~10²
	120	0.34 (0.44)	11.5 (7.3)	10³~10⁴	0.022 (0.031)	－50.2 (－44.5)	10~10²
	180	0.48 (0.58)	13.5 (10.0)	10³~10⁴	0.054 (0.064)	－44.1 (－39.6)	10~10²
2	As-spun	3.9×10^－5 (6.0×10^－5)	38.7 (30.9)	10²~10³	2.0×10^－5 (3.4×10^－5)	－11.6 (－3.7)	10²~10³
	60	3.1×10^－4 (4.2×10^－4)	23.3 (19.3)	10²~10³	6.3×10^－5 (8.8×10^－5)	－27.9 (－11.6)	10²~10³
	120	0.019 (0.024)	22.6 (15.7)	10³~10⁴	0.016 (0.021)	－40.3 (－35.7)	10²~10³
	180	0.027 (0.037)	39.1 (36.9)	10³~10⁴	0.025 (0.050)	－33.9 (－17.0)	10²~10³
3	As-spun	0.013 (0.015)	21.4 (15.4)	10⁵~10⁶	—	—	—
	60	0.036 (0.041)	20.5 (16.5)	10⁵~10⁶	—	—	—
	120	0.046 (0.076)	15.0 (11.0)	10⁵~10⁶	1.3×10^－4 (2.8×10^－4)	－59.7 (－28.2)	~10²
4	As-spun	3.5×10^－4 (4.5×10^－4)	24.3 (22.6)	10⁴~10⁶	—	—	—
	60	5.5×10^－4 (7.5×10^－4)	32.9 (29.8)	10⁴~10⁵	—	—	—
	120	0.020 (0.024)	27.8 (21.0)	10⁵~10⁶	1.2×10^－4 (3.3×10^－4)	－59.4 (－27.4)	10~10³
5	As-spun	7.2×10^－4 (9.8×10^－4)	22.0 (15.9)	10⁴~10⁶	—	—	—
	60	2.6×10^－3 (3.2×10^－3)	22.8 (19.1)	10⁴~10⁶	—	—	—
	120	5.4×10^－3 (8.1×10^－3)	19.4 (12.5)	10⁵~10⁶	4.5×10^－6 (1.2×10^－5)	－62.8 (－38.8)	~10

Compound	T_a/℃	μ_e,ave (μ_e,max)/(cm²•V^－1•s^－1)	V_T,ave (V_T,min)/V	I_on/I_off	μ_h,ave (μ_h,max)/(cm²•V^－1•s^－1)	V_T,ave (V_T,min)/V	I_on/I_off
1	As-spun	2.8×10^－3 (3.4×10^－3)	25.2 (20.1)	10³~10⁴	—	—	—
	60	0.017 (0.022)	17.2 (7.9)	10³~10⁴	3.6×10^－4 (3.9×10^－4)	－30.6 (－24.6)	10~10²
	120	0.34 (0.44)	11.5 (7.3)	10³~10⁴	0.022 (0.031)	－50.2 (－44.5)	10~10²
	180	0.48 (0.58)	13.5 (10.0)	10³~10⁴	0.054 (0.064)	－44.1 (－39.6)	10~10²
2	As-spun	3.9×10^－5 (6.0×10^－5)	38.7 (30.9)	10²~10³	2.0×10^－5 (3.4×10^－5)	－11.6 (－3.7)	10²~10³
	60	3.1×10^－4 (4.2×10^－4)	23.3 (19.3)	10²~10³	6.3×10^－5 (8.8×10^－5)	－27.9 (－11.6)	10²~10³
	120	0.019 (0.024)	22.6 (15.7)	10³~10⁴	0.016 (0.021)	－40.3 (－35.7)	10²~10³
	180	0.027 (0.037)	39.1 (36.9)	10³~10⁴	0.025 (0.050)	－33.9 (－17.0)	10²~10³
3	As-spun	0.013 (0.015)	21.4 (15.4)	10⁵~10⁶	—	—	—
	60	0.036 (0.041)	20.5 (16.5)	10⁵~10⁶	—	—	—
	120	0.046 (0.076)	15.0 (11.0)	10⁵~10⁶	1.3×10^－4 (2.8×10^－4)	－59.7 (－28.2)	~10²
4	As-spun	3.5×10^－4 (4.5×10^－4)	24.3 (22.6)	10⁴~10⁶	—	—	—
	60	5.5×10^－4 (7.5×10^－4)	32.9 (29.8)	10⁴~10⁵	—	—	—
	120	0.020 (0.024)	27.8 (21.0)	10⁵~10⁶	1.2×10^－4 (3.3×10^－4)	－59.4 (－27.4)	10~10³
5	As-spun	7.2×10^－4 (9.8×10^－4)	22.0 (15.9)	10⁴~10⁶	—	—	—
	60	2.6×10^－3 (3.2×10^－3)	22.8 (19.1)	10⁴~10⁶	—	—	—
	120	5.4×10^－3 (8.1×10^－3)	19.4 (12.5)	10⁵~10⁶	4.5×10^－6 (1.2×10^－5)	－62.8 (－38.8)	~10

核扩展的萘二酰亚胺-插烯四硫富瓦烯类双极性有机半导体

Core-Expanded Naphthalene Diimides-Vinylogous Tetrathia-fulvalenes toward Ambipolar Organic Semiconductors

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[7]	辛涵申, 葛从伍, 傅丽娜, 杨笑迪, 高希珂. 薁乙炔封端的萘二酰亚胺小分子的设计合成与场效应性能研究[J]. 有机化学, 2017, 37(3): 711-719.
[8]	陈华杰. 高迁移率聚合物半导体材料最新进展[J]. 有机化学, 2016, 36(3): 460-479.
[9]	夏昕, 雷霆, 裴坚, 刘晨江. 有机场效应晶体管中给体-受体共聚物材料研究进展[J]. 有机化学, 2014, 34(9): 1905-1915.