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

doi:10.6023/cjoc202404033

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (9): 2810-2819.DOI: 10.6023/cjoc202404033 Previous Articles Next Articles

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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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Abstract

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

Cite this article

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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References 18

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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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