Synthesis of Nitrogen-Containing Isoindigo Derivatives and Their Applications in Optoelectronic Materials

doi:10.6023/cjoc202202031

Abstract

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

Cite this article

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

含氮异靛蓝衍生物的合成及其在光电材料中的应用