含氮异靛蓝衍生物的合成及其在光电材料中的应用

doi:10.6023/cjoc202202031

摘要/Abstract

异靛蓝因其良好的平面性以及较强的拉电子能力, 一直作为优秀的受体材料在有机光电材料中扮演着重要的角色, 对异靛蓝的结构改造也成为了学术界关注的重点. 其中, 含氮异靛蓝衍生物的合成及其在光电材料中的应用取得了较大的进展, 氮原子的引入可进一步调节异靛蓝衍生物推拉电子的能力以及平面性, 从而调节其光电性能. 本综述总结了近年来含氮的芳杂环异靛蓝衍生物的发展过程以及在光电材料中的应用, 以期为功能化共轭分子的设计提供有益的借鉴和指导.

关键词: 含氮异靛蓝, 有机光电材料, 聚合物场效应晶体管

Isoindigo has played an important role in organic optoelectronic materials as an excellent acceptor building block due to its planarity and electron-withdrawing capability. The modification, of isoindigo has also become the focus of academia. Recently, great achievements have been made in the synthesis of nitrogen-containing isoindigo derivatives and their applications as optoelectronic materials. The incorporation of nitrogen atom can further adjust the electron push/pull ability and the planarity of isoindigo derivatives, thereby tune their optoelectronic properties. The development of nitrogen-containing isoindigo derivatives, as well as their applications in optoelectronic materials, which we hope would provide useful information for the design of conjugated optoelectronic materials, is summarized.

Key words: nitrogen-containing isoindigo, organic optoelectronic materials, polymer field effect transistors

引用此文

罗力铖, 李亮, 穆有炳, 李博文, 万晓波. 含氮异靛蓝衍生物的合成及其在光电材料中的应用[J]. 有机化学, 2022, 42(7): 1960-1973.

Licheng Luo, Liang Li, Youbing Mu, Bowen Li, Xiaobo Wan. Synthesis of Nitrogen-Containing Isoindigo Derivatives and Their Applications in Optoelectronic Materials[J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 1960-1973.

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Compd.	V_oc/V	J_sc/(mA•cm^–2)	FF/%	PCE/%
24	0.66±0.05	2.7±0.3	31±3	0.74
25	0.28±0.09	0.22±0.04	28±2	0.03
26	0.67±0.01	2.5±0.9	40±3	0.93
27	0.3±0.1	0.6±0.2	22±2	0.07

Compd.	V_oc/V	J_sc/(mA•cm^–2)	FF/%	PCE/%
24	0.66±0.05	2.7±0.3	31±3	0.74
25	0.28±0.09	0.22±0.04	28±2	0.03
26	0.67±0.01	2.5±0.9	40±3	0.93
27	0.3±0.1	0.6±0.2	22±2	0.07

Polymer	M_n(kDa)/PDI	HOMO/eV	LUMO/eV	μ_h/(cm²•V^–1•s^–1)	μ_e/(cm²•V^–1•s^–1)	I_on/I_off	Device structure
IIDDT-C3	20.4/2.0	–5.70	–3.70	3.62 (2.98)	N/A	10⁶	BG/TC
PAIID-BT-C1	61.1/3.0	–5.66	–3.62	3.63 (2.86)	N/A	N/A	BG/BC
PAIID-BT-C3	50.6/3.87	–5.67	–3.64	7.28 (6.43)	N/A	N/A	BG/BC
PAIID-BT-C1	61.1/3.0	–5.66	–3.62	0.45 (0.27)	0.47 (0.30)	N/A	TG/BC
PAIID-BT-C3	50.6/3.87	–5.67	–3.64	2.33 (1.89）	0.78 (0.48)	N/A	TG/BC
5DNIID-2T	33.46/2.68	–5.92	–3.82	1.27×10^–3	N/A	N/A	BG/TC
PAIIDBT	14/1.6	–5.5	–3.4	N/A	1.0	10⁶	TG/BC
PAIIDSe	96/2.0	–5.3	–3.3	0.2	0.5	10²~10³	TG/BC
PAIID-TT-C3	19.8/2.63	–5.68	–3.70	1.14 (0.78)	1.54 (1.12)	10~10²	TG/BC
PAIID-DTE-C3	116.4/2.49	–5.56	–3.60	1.91 (1.59)	0.04 (0.02)	10³~10⁴	TG/BC
PAIID-BS-C3	37.7/3.92	–5.58	–3.66	2.56 (2.38)	0.44 (0.32)	10³~10⁴	TG/BC
PAIID-DSE-C3	42.4/4.24	–5.54	–3.65	0.80 (0.73)	0.18 (0.14)	10³~10⁴	TG/BC
BDPPV	41.8/2.39	–6.20	–4.01	N/A	0.5	10⁴	TG/BC
BDOPV-2T	77.2/3.00	–5.72	–4.15	N/A	1.74(1.42)	N/A	TG/BC
AzaBDOPV-2T	135/2.62	–5.77	–4.45	N/A	3.22 (1.63)	N/A	TG/BC
PBABDF-DT	32.6/5.0	–5.70	–4.04	1.86 (1.34)	N/A	10⁶	BG/TC
PBABDF-TVT	30.8/5.83	–5.60	–3.99	1.56 (1.17)	N/A	1.0×10⁶	BG/TC
PNBDOPV-DTBT	29.9/2.68	–5.87	–3.92	5.97(4.70)	7.07 (4.75)	N/A	TG/BC
PNBDOPV-DTF2BT	31.31/2.71	–6.05	–3.92	0.83 (0.80)	3.77 (3.14)	N/A	TG/BC
PAIID-TFBVB-C1	26.06/1.48	–6.23	–3.69	N/A	5.9×10^–4(3.6×10^–4)	10⁴	TG/BC
PAIID-TFBVB-C3	32.16/1.95	–6.18	–3.61	N/A	8.8×10^–4(5.9×10^–4)	10⁵	TG/BC
PAIID-BVB-C3	55.3/2.32	–5.73	–3.47	0.047 (0.036)	N/A	10⁵	TG/BC
PAZDTBT	19.3/1.94	–5.63	–3.53	0.377 (0.496)	0.092 (0.137)	10³~10⁴	TG/BC
PBABDF-TVT	30.8/5.83	–5.60	–3.99	1.56 (1.17)	N/A	1.0×10⁶	BG/TC
PNBDOPV-DTBT	29.9/2.68	–5.87	–3.92	5.97 (4.70)	7.07 (4.75)	N/A	TG/BC
PAZDTBTF	13.5/1.71	–5.78	–3.56	0.358 (0.417)	0.126 (0.143)	10³~10⁴	TG/BC
PBAID1-BT	39.5/2.5	–5.15	–3.87	1.8×10^–2	N/A	N/A	BG/TC
Polymer	M_n(kDa)/PDI	HOMO/eV	LUMO/eV	μ_h/(cm²•V^–1•s^–1)	μ_e/(cm²•V^–1•s^–1)	I_on/I_off	Device structure
PBAID2-BT	46.8/2.3	–5.16	–3.87	1.33	0.94	10²~10³	BG/TC
PBAID3-BT	42.3/2.7	–5.15	–3.86	1.66	0.88	10²~10³	BG/TC
PBAID3-2FBT	40.6/2.6	–5.17	–3.90	1.68	1.37	10³~10⁴	BG/TC
PNBDO-TT	54.3/2.36	–5.99	–4.07	N/A	2.08	10³~10⁴	N/A
PNBDO-DMTT	43.7/1.72	–5.94	–4.00	0.0255	0.739	10³~10⁴	N/A
PNBDO-MOTT	34.5/1.93	–5.75	–4.00	0.0711	0.103	10³~10⁴	N/A
P2N2F-BT	35.3/2.88	–5.67	–3.88	0.30 (0.19)	1.51 (1.28)	10³	TG/BC
P2N2F-4FBT	20.3/2.20	–6.04	–4.01	N/A	1.24 (1.08)	10⁵	TG/BC
P(TzII-TTT)	71.1/N/A	–5.13	–3.58	3.93 (3.31)	1.07 (0.76)	10²	TG/BC
P(TzII-TTT)	71.1/N/A	–5.13	–3.58	4.34 (3.20)	N/A	10²	BG/TC
P(TzII-T-Se-T)	103.7/N/A	–5.12	–3.53	3.77 (2.73)	1.59 (0.83)	10²	TG/BC
P(TzII-T-Te-T)	19.4/N/A	–5.11	–3.55	0.04 (0.04)	0.64 (0.39)	10	TG/BC
P(TzII-Se-T-Se)	28.8/N/A	–5.17	–3.60	0.12 (0.05)	0.58 (0.41)	10	TG/BC
P(TzII-Se-Se-Se)	28.1/N/A	–5.20	–3.59	1.26 (0.72)	0.15 (0.13)	10²	TG/BC
P(TzII-Se-Te-Se)	8.3/N/A	–5.21	–3.61	0.90 (0.66)	0.08 (0.04)	10²	TG/BC

Polymer	M_n(kDa)/PDI	HOMO/eV	LUMO/eV	μ_h/(cm²•V^–1•s^–1)	μ_e/(cm²•V^–1•s^–1)	I_on/I_off	Device structure
IIDDT-C3	20.4/2.0	–5.70	–3.70	3.62 (2.98)	N/A	10⁶	BG/TC
PAIID-BT-C1	61.1/3.0	–5.66	–3.62	3.63 (2.86)	N/A	N/A	BG/BC
PAIID-BT-C3	50.6/3.87	–5.67	–3.64	7.28 (6.43)	N/A	N/A	BG/BC
PAIID-BT-C1	61.1/3.0	–5.66	–3.62	0.45 (0.27)	0.47 (0.30)	N/A	TG/BC
PAIID-BT-C3	50.6/3.87	–5.67	–3.64	2.33 (1.89）	0.78 (0.48)	N/A	TG/BC
5DNIID-2T	33.46/2.68	–5.92	–3.82	1.27×10^–3	N/A	N/A	BG/TC
PAIIDBT	14/1.6	–5.5	–3.4	N/A	1.0	10⁶	TG/BC
PAIIDSe	96/2.0	–5.3	–3.3	0.2	0.5	10²~10³	TG/BC
PAIID-TT-C3	19.8/2.63	–5.68	–3.70	1.14 (0.78)	1.54 (1.12)	10~10²	TG/BC
PAIID-DTE-C3	116.4/2.49	–5.56	–3.60	1.91 (1.59)	0.04 (0.02)	10³~10⁴	TG/BC
PAIID-BS-C3	37.7/3.92	–5.58	–3.66	2.56 (2.38)	0.44 (0.32)	10³~10⁴	TG/BC
PAIID-DSE-C3	42.4/4.24	–5.54	–3.65	0.80 (0.73)	0.18 (0.14)	10³~10⁴	TG/BC
BDPPV	41.8/2.39	–6.20	–4.01	N/A	0.5	10⁴	TG/BC
BDOPV-2T	77.2/3.00	–5.72	–4.15	N/A	1.74(1.42)	N/A	TG/BC
AzaBDOPV-2T	135/2.62	–5.77	–4.45	N/A	3.22 (1.63)	N/A	TG/BC
PBABDF-DT	32.6/5.0	–5.70	–4.04	1.86 (1.34)	N/A	10⁶	BG/TC
PBABDF-TVT	30.8/5.83	–5.60	–3.99	1.56 (1.17)	N/A	1.0×10⁶	BG/TC
PNBDOPV-DTBT	29.9/2.68	–5.87	–3.92	5.97(4.70)	7.07 (4.75)	N/A	TG/BC
PNBDOPV-DTF2BT	31.31/2.71	–6.05	–3.92	0.83 (0.80)	3.77 (3.14)	N/A	TG/BC
PAIID-TFBVB-C1	26.06/1.48	–6.23	–3.69	N/A	5.9×10^–4(3.6×10^–4)	10⁴	TG/BC
PAIID-TFBVB-C3	32.16/1.95	–6.18	–3.61	N/A	8.8×10^–4(5.9×10^–4)	10⁵	TG/BC
PAIID-BVB-C3	55.3/2.32	–5.73	–3.47	0.047 (0.036)	N/A	10⁵	TG/BC
PAZDTBT	19.3/1.94	–5.63	–3.53	0.377 (0.496)	0.092 (0.137)	10³~10⁴	TG/BC
PBABDF-TVT	30.8/5.83	–5.60	–3.99	1.56 (1.17)	N/A	1.0×10⁶	BG/TC
PNBDOPV-DTBT	29.9/2.68	–5.87	–3.92	5.97 (4.70)	7.07 (4.75)	N/A	TG/BC
PAZDTBTF	13.5/1.71	–5.78	–3.56	0.358 (0.417)	0.126 (0.143)	10³~10⁴	TG/BC
PBAID1-BT	39.5/2.5	–5.15	–3.87	1.8×10^–2	N/A	N/A	BG/TC
Polymer	M_n(kDa)/PDI	HOMO/eV	LUMO/eV	μ_h/(cm²•V^–1•s^–1)	μ_e/(cm²•V^–1•s^–1)	I_on/I_off	Device structure
PBAID2-BT	46.8/2.3	–5.16	–3.87	1.33	0.94	10²~10³	BG/TC
PBAID3-BT	42.3/2.7	–5.15	–3.86	1.66	0.88	10²~10³	BG/TC
PBAID3-2FBT	40.6/2.6	–5.17	–3.90	1.68	1.37	10³~10⁴	BG/TC
PNBDO-TT	54.3/2.36	–5.99	–4.07	N/A	2.08	10³~10⁴	N/A
PNBDO-DMTT	43.7/1.72	–5.94	–4.00	0.0255	0.739	10³~10⁴	N/A
PNBDO-MOTT	34.5/1.93	–5.75	–4.00	0.0711	0.103	10³~10⁴	N/A
P2N2F-BT	35.3/2.88	–5.67	–3.88	0.30 (0.19)	1.51 (1.28)	10³	TG/BC
P2N2F-4FBT	20.3/2.20	–6.04	–4.01	N/A	1.24 (1.08)	10⁵	TG/BC
P(TzII-TTT)	71.1/N/A	–5.13	–3.58	3.93 (3.31)	1.07 (0.76)	10²	TG/BC
P(TzII-TTT)	71.1/N/A	–5.13	–3.58	4.34 (3.20)	N/A	10²	BG/TC
P(TzII-T-Se-T)	103.7/N/A	–5.12	–3.53	3.77 (2.73)	1.59 (0.83)	10²	TG/BC
P(TzII-T-Te-T)	19.4/N/A	–5.11	–3.55	0.04 (0.04)	0.64 (0.39)	10	TG/BC
P(TzII-Se-T-Se)	28.8/N/A	–5.17	–3.60	0.12 (0.05)	0.58 (0.41)	10	TG/BC
P(TzII-Se-Se-Se)	28.1/N/A	–5.20	–3.59	1.26 (0.72)	0.15 (0.13)	10²	TG/BC
P(TzII-Se-Te-Se)	8.3/N/A	–5.21	–3.61	0.90 (0.66)	0.08 (0.04)	10²	TG/BC