Recent Advances in Multi-resonance Luminescent Materials Based on Indolo[3,2,1-jk]carbazole

doi:10.6023/cjoc202503030

Abstract

The research progress of multi-resonance (MR) luminescent materials based on indolo[3,2,1-jk]carbazole is summarized. Indolo[3,2,1-jk]carbazole-based MR molecules have shown great application potential in the field of organic light-emitting diodes (OLEDs) due to their unique molecular structures and excellent optoelectronic properties. The basic structure of the indolo[3,2,1-jk]carbazole skeleton and its application advantages in MR luminescent molecules are introduced, and then the methods for optimizing their optoelectronic properties through strategies including conjugation length extension, peripheral group modification, and heavy atom effects are discussed in detail. It has been shown that through various molecular design strategies, indolo[3,2,1-jk]carbazole-based MR luminescent molecules have made significant progress in improving luminescence efficiency and achieving narrowband emission, providing new possibilities for the development of MR luminescent molecules. In addition, through reasonable molecular design, it is possible to achieve full-color emission from ultraviolet to red light, which also provides new ideas and materials for OLED technology. Finally, the current challenges in research and the future prospects are discussed.

Key words: multi-resonance, organic light-emitting diode (OLED), luminescent material, indolo[3,2,1-jk]carbazole

Cite this article

Zhiming Ren, Lijuan Xie, Jing Jin, Yujie Wu, Di Liu, Jiuyan Li. Recent Advances in Multi-resonance Luminescent Materials Based on Indolo[3,2,1-jk]carbazole[J]. Chinese Journal of Organic Chemistry, 2025, 45(11): 4108-4127.

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References 67

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Compound	λ_em/nm (Sol/film)	Ф_PL/% (Sol/film)	E_S1/E_T1/∆E_ST/eV	HOMO/LUMO/E_g/eV	T_d/T_g/℃	Ref.
tDIDCz	393/—	60.0/—	3.15/2.71/0.44	－5.98/－2.59/3.39	—/—	[12]
m-FLDID	400/404	71.0/—	3.08/2.72/0.36	－5.94/－2.62/3.32	—/—	[27]
m-FDIDCz-2DPA	451^a/458	—/66.7	—/—/—	－5.14/－2.39/2.75^b	545/—	[29]
DICz	446^a/451	99/93	—/—/—	—/—/—	—/—	[16]
mMes₂DICz	445^a/451	99/99	—/—/—	－5.28/－2.77/2.51	455/—
mtPh₂DICz	457^a461	99/94	—/—/—	－5.45/－2.69/3.02	496/—
Cz-DICz	457/460	98.6/98.4	2.71/2.37/0.34	−5.55/−2.59/2.96/	—/—	[31]
DiICzMes4	—/—	—/82	2.82/2.56/0.26	－5.45/－2.43/3.02	450/—	[26]
p-FLDID	445/449	97.3/82.8	2.76/2.57/0.19	－5.76/－2.90/2.85	0.32/0.65	[33]
BisICz	436/442	81/76	2.84/2.55/0.29	－5.80/－3.00/2.80	0.81/—	[16]
tBisICz	436/442	95/77	2.84/2.55/0.29	－5.70/－2.90/2.80	0.48/0.47
tPBisICz	445/450	91/78	2.81/2.54/0.27	－5.90/－3.20/2.70	0.35/0.56
pICz-PPO	438/—	42/—	2.82/2.47/0.35	－5.34/－2.54/2.80	514/—	[35]
pICz-2PPO	439/—	42/—	2.82/2.46/0.36	－5.37/－2.57/2.80	552/—
tBisICz-DPA	444/—	96/—	2.79/2.52/0.28	－5.65/－2.89/2.76	0.45/0.51	[43]
tBisICz-PhCz	440/—	91/—	2.82/2.51/0.31	－5.67/－2.89/2.78	0.45/0.46
pICz	441^a/—	88/—	2.81/2.52/0.29	－5.29/－2.5/2.79	—/—	[45]
pICz-TPA	447^a/—	90/—	2.77/2.45/0.32	－5.14/－2.39/2.75	—/—
DPA-bisICZ	500/505	78/92	2.48/2.34/0.14	－4.91/－2.43/2.48	0.78/0.14	[46]
tBuDPA-bisICZ	508/515	82/93	2.44/2.29/0.15	－4.82/－2.39/2.43	0.79/0.14
MeODPA-bisICZ	523/532	83/90	2.35/2.19/0.16	－4.68/－2.33/2.35	0.78/0.12
2,5-tDPAtDIDCz	—/438^c	88/—	2.83/2.65/0.18	－5.55/－2.74/2.81	0.26/0.62	[47]
1,6-tDPAtDIDCz	—/415^c	92/—	2.99/2.58/0.41	－5.54/－2.66/2.88	0.92/—
tBu-TiTAT	452^a/454	—/76	2.90/2.54/0.36	－5.39/－2.64/2.75^b	468/—	[49]
tBu-TTAT	425^a/430	—/36	3.13/2.60/0.53	－5.30/－2.55/2.75^b	409/—
α-NAICZ	598/—	97/—	2.07/1.69/0.38	－4.69/－2.56/2.13	431/—	[53]
α-EtNAICZ	620/—	90/—	2.00/1.69/0.31	－4.53/－2.48/2.05	412/—
NBisICz	445/457	—/63	2.79/2.37/0.42	－5.68/－2.92/2.76^b	525/—	[56]
NBisICz-PCz	445/454	—/64	2.79/2.37/0.42	－5.65/－2.90/2.75^b	541/—
NBisICz-DPA	451/460	—/64	2.75/2.37/0.37	－5.71/－2.98/2.73^b	520/—
ββICZ	502/—	99/—	2.47/1.94/0.53	－5.35/－2.85/2.50	518/—	[58]
αβICZ	472/—	56/—	2.64/2.11/0.53	－5.55/－2.82/2.73	—/—
ββCNICZ	501/—	95/—	2.47/1.93/0.54	－5.51/－3.00/2.51	550/—
t-mp3ICz	436^c	99/—	2.84/2.54/0.30	－5.63/－2.84/2.79	0.49/0.50	[61]
p-mp3ICz	444^c	97/—	2.80/2.54/0.26	－5.63/－2.87/2.76	0.35/0.62
t3IDCz	—/459^c	92/—	2.70/2.49/0.21	－5.50/－2.85/2.65	0.28/0.64	[64]
p3IDCz	—/461^c	100/—	2.69/2.50/0.19	－5.41/－2.77/2.64	0.28/0.72
IDCz-DBS	456/—	99/—	2.72/2.35/0.37	—/—/—	—/—	[66]

Compound	λ_em/nm (Sol/film)	Ф_PL/% (Sol/film)	E_S1/E_T1/∆E_ST/eV	HOMO/LUMO/E_g/eV	T_d/T_g/℃	Ref.
tDIDCz	393/—	60.0/—	3.15/2.71/0.44	－5.98/－2.59/3.39	—/—	[12]
m-FLDID	400/404	71.0/—	3.08/2.72/0.36	－5.94/－2.62/3.32	—/—	[27]
m-FDIDCz-2DPA	451^a/458	—/66.7	—/—/—	－5.14/－2.39/2.75^b	545/—	[29]
DICz	446^a/451	99/93	—/—/—	—/—/—	—/—	[16]
mMes₂DICz	445^a/451	99/99	—/—/—	－5.28/－2.77/2.51	455/—
mtPh₂DICz	457^a461	99/94	—/—/—	－5.45/－2.69/3.02	496/—
Cz-DICz	457/460	98.6/98.4	2.71/2.37/0.34	−5.55/−2.59/2.96/	—/—	[31]
DiICzMes4	—/—	—/82	2.82/2.56/0.26	－5.45/－2.43/3.02	450/—	[26]
p-FLDID	445/449	97.3/82.8	2.76/2.57/0.19	－5.76/－2.90/2.85	0.32/0.65	[33]
BisICz	436/442	81/76	2.84/2.55/0.29	－5.80/－3.00/2.80	0.81/—	[16]
tBisICz	436/442	95/77	2.84/2.55/0.29	－5.70/－2.90/2.80	0.48/0.47
tPBisICz	445/450	91/78	2.81/2.54/0.27	－5.90/－3.20/2.70	0.35/0.56
pICz-PPO	438/—	42/—	2.82/2.47/0.35	－5.34/－2.54/2.80	514/—	[35]
pICz-2PPO	439/—	42/—	2.82/2.46/0.36	－5.37/－2.57/2.80	552/—
tBisICz-DPA	444/—	96/—	2.79/2.52/0.28	－5.65/－2.89/2.76	0.45/0.51	[43]
tBisICz-PhCz	440/—	91/—	2.82/2.51/0.31	－5.67/－2.89/2.78	0.45/0.46
pICz	441^a/—	88/—	2.81/2.52/0.29	－5.29/－2.5/2.79	—/—	[45]
pICz-TPA	447^a/—	90/—	2.77/2.45/0.32	－5.14/－2.39/2.75	—/—
DPA-bisICZ	500/505	78/92	2.48/2.34/0.14	－4.91/－2.43/2.48	0.78/0.14	[46]
tBuDPA-bisICZ	508/515	82/93	2.44/2.29/0.15	－4.82/－2.39/2.43	0.79/0.14
MeODPA-bisICZ	523/532	83/90	2.35/2.19/0.16	－4.68/－2.33/2.35	0.78/0.12
2,5-tDPAtDIDCz	—/438^c	88/—	2.83/2.65/0.18	－5.55/－2.74/2.81	0.26/0.62	[47]
1,6-tDPAtDIDCz	—/415^c	92/—	2.99/2.58/0.41	－5.54/－2.66/2.88	0.92/—
tBu-TiTAT	452^a/454	—/76	2.90/2.54/0.36	－5.39/－2.64/2.75^b	468/—	[49]
tBu-TTAT	425^a/430	—/36	3.13/2.60/0.53	－5.30/－2.55/2.75^b	409/—
α-NAICZ	598/—	97/—	2.07/1.69/0.38	－4.69/－2.56/2.13	431/—	[53]
α-EtNAICZ	620/—	90/—	2.00/1.69/0.31	－4.53/－2.48/2.05	412/—
NBisICz	445/457	—/63	2.79/2.37/0.42	－5.68/－2.92/2.76^b	525/—	[56]
NBisICz-PCz	445/454	—/64	2.79/2.37/0.42	－5.65/－2.90/2.75^b	541/—
NBisICz-DPA	451/460	—/64	2.75/2.37/0.37	－5.71/－2.98/2.73^b	520/—
ββICZ	502/—	99/—	2.47/1.94/0.53	－5.35/－2.85/2.50	518/—	[58]
αβICZ	472/—	56/—	2.64/2.11/0.53	－5.55/－2.82/2.73	—/—
ββCNICZ	501/—	95/—	2.47/1.93/0.54	－5.51/－3.00/2.51	550/—
t-mp3ICz	436^c	99/—	2.84/2.54/0.30	－5.63/－2.84/2.79	0.49/0.50	[61]
p-mp3ICz	444^c	97/—	2.80/2.54/0.26	－5.63/－2.87/2.76	0.35/0.62
t3IDCz	—/459^c	92/—	2.70/2.49/0.21	－5.50/－2.85/2.65	0.28/0.64	[64]
p3IDCz	—/461^c	100/—	2.69/2.50/0.19	－5.41/－2.77/2.64	0.28/0.72
IDCz-DBS	456/—	99/—	2.72/2.35/0.37	—/—/—	—/—	[66]

Emitter	Doping conc./%	V_on/V	CE_max/(cd•A⁻¹)	EQE_max(100/1000)/%	EL_max/nm	CIE(x, y)	FWHM	Ref.
tDIDCz	1	3.5	—	2.75	401	(0.164, 0.018)	14	[12]
	3	3.5	—	3.30	402	(0.164, 0.019)	20
m-FLDID	1	4.1	—	4.40	407	(0.168, 0.024)	17	[27]
	3	4.0	—	5.10	409	(0.166, 0.025)	22
m-FDIDCz-2DPA		2.64	—	8.32 (—/7.20)	459	(0.140, 0.105)	30	[29]
DICz	1	3.8	—	5.5 (4.6/—)	—	(0.14, 0.10)	35	[17]
mMes₂DICz	1	3.3	—	9.5 (7.8/—)	—	(0.15, 0.04)	13
	2	3.1	—	10.2 (8.2/—)	—	(0.14, 0.05)	15
	4	3.0	—	10.6 (8.6/—)	—	(0.14, 0.09)	33
mtPh2DICz	1	3.4	—	10.3 (8.3/—)	—	(0.13, 0.14)	33
Cz-DICz (non- sensitized)	1	3.1	8.59	8.79	460	(0.14, 0.11)	18	[31]
	2	3.1	7.77	7.93	461	(0.13, 0.11)	19
	4	3.2	7.28	7.65	462	(0.13, 0.12)	19
Cz-DICza	1	2.9	25.62	25.6	460	(0.14, 0.10)	18
	2	2.8	25.28	23.8	460	(0.14, 0.11)	18
	4	2.8	25.21	22.1	461	(0.14, 0.11)	18
Cz-DICz^b	—	2.5	8.6	9.4	460	(0.13, 0.09)	15
DiICzMes4	—	5.2	—	3.0 (1.9/—)	446	(0.15, 0.11)	—	[26]
p-FLDID	1	3.5	11.2	18.7	452	(0.147, 0.058)	23	[33]
BisICz	1	—	2.9	6.5	437	(0.16, 0.04)	24	[16]
tBisICz	1	—	8.4	15.1	445	(0.16, 0.05)	22
tPBisICz	1	—	13.5	23.1	452	(0.15, 0.05)	21
pICz-PPO^a	1	3.6	8.7	12.1 (7.1/—)	442	(0.16, 0.08)	20	[35]
pICz-2PPO^a	1	3.6	12.6	17.7 (12.8/—)	441	(0.16, 0.07)	19
tBisICz-DPA	1	—	11.0	20.0	448	(0.15, 0.05)	28	[43]
	3	—	12.3	20.4	452	(0.15, 0.05)	28
	5	—	12.1	19.5	453	(0.15, 0.06)	29
tBisICz-PhCz	1	—	8.5	19.7	445	(0.17, 0.05)	20
	3	—	11.6	24.9	446	(0.16, 0.04)	19
	5	—	7.7	16.6	447	(0.15, 0.04)	19
pICz^c		3.5	30.1	32.0 (6.7/—)	445	(0.15, 0.10)	—	[45]
pICz-TPA^c		3.6	31.5	34.7 (11.2/—)	445	(0.15, 0.085)	—
DPA-bisICZ		2.5	—	24.4	508	(0.17, 0.66)	34	[46]
tBuDPA-bisICZ		2.9	—	24.7	514	(0.20, 0.68)	35
MeODPA-bisICZ		2.1	—	22.6	532	(0.31, 0.65)	40
2,5-tDPAtDIDCz^d	1	3.7 (@1.0 cd•m^－2)	24.2	23.4	464	(0.13, 0.12)	36	[47]
2,5-tDPAtDIDCz^e	1	4.1 (@1.0 cd•m^－2)	34.1	30.8	466	(0.13, 0.14)	38
1,6-tDPAtDIDCz^d	1	3.5 (@1.0 cd•m^－2)	3.4	6.4	437	(0.16, 0.04)	32
1,6-tDPAtDIDCz^e	1	3.9 (@1.0 cd•m^－2)	8.7	7.3	438	(0.16, 0.05)	36
tBu-TiTAT		6.0	7.8	6.3 (4.1/2.6)	454	(0.14, 0.14)		[49]
tBu-TiTAT^c		6.0	19.6	12.6 (7.1/5.7)	454	(0.16, 0.19)	55
α-NAICZ	—	2.3	27.4	20.2 (—/19.6), 18.6^f	610	(0.65, 0.35)	38	[53]
α-EtNAICZ	—	2.2	5.7	6.3 (—/4.5), 3.9^f	631	(0.51, 0.39)	44
NBisICz	5% TTF	6.1	7.9	7.1 (—/6.9)	469	(0.127, 0.148)	48.4	[56]
NBisICz-PCz	2% PSF	7.2	16.6	18.8 (—/5.5)	453	(0.143, 0.076)	22
NBisICz-DPA	2% PSF	6.6	19.1	20.6 (—/7.9)	454	(0.141, 0.085)	27.5
ββICZ^a	1	2.4	100.9	30.9 (—/28.9), 23.2^f	508	(0.22, 0.64)	19	[58]
ββCNICZ^a	1	2.6	87.3	27.0 (—/25.5), 18.6^f	509	(0.21, 0.65)	19
t-mp3ICz	1	V_d-5.7	12.2	24.3	446	(0.154, 0.044)	21	[61]
p-mp3ICz	1	V_d-5.7	16.1	24.2	451	(0.147, 0.061)	23
	1	V_d-5.3	18.8	26.8	452	(0.142, 0.061)	25
t3IDCz	1	6.9 (@1000 cd•m^－2)	36.9	30.0	472	(0.119, 0.161)	25	[64]
t3IDC^g	1	6.9 (@100 cd•m^－2)	35.4	30.9	471	(0.116, 0.158)	26
p3IDCz	1	6.9 (@1000 cd•m^－2)	37.9	30.9	472	(0.120, 0.158)	23
p3IDCz^g	1	6.9 (@100 cd•m^－2)	43.4	33.8	473	(0.111, 0.188)	28
p3IDCz^h	1	6.9 (@100 cd•m^－2)	42.6	30.5	474	(0.116, 0.213)	33
IDCz-DBS	—	—	—	31.1	461	(0.135, 0.160)	21	[66]

Emitter	Doping conc./%	V_on/V	CE_max/(cd•A⁻¹)	EQE_max(100/1000)/%	EL_max/nm	CIE(x, y)	FWHM	Ref.
tDIDCz	1	3.5	—	2.75	401	(0.164, 0.018)	14	[12]
	3	3.5	—	3.30	402	(0.164, 0.019)	20
m-FLDID	1	4.1	—	4.40	407	(0.168, 0.024)	17	[27]
	3	4.0	—	5.10	409	(0.166, 0.025)	22
m-FDIDCz-2DPA		2.64	—	8.32 (—/7.20)	459	(0.140, 0.105)	30	[29]
DICz	1	3.8	—	5.5 (4.6/—)	—	(0.14, 0.10)	35	[17]
mMes₂DICz	1	3.3	—	9.5 (7.8/—)	—	(0.15, 0.04)	13
	2	3.1	—	10.2 (8.2/—)	—	(0.14, 0.05)	15
	4	3.0	—	10.6 (8.6/—)	—	(0.14, 0.09)	33
mtPh2DICz	1	3.4	—	10.3 (8.3/—)	—	(0.13, 0.14)	33
Cz-DICz (non- sensitized)	1	3.1	8.59	8.79	460	(0.14, 0.11)	18	[31]
	2	3.1	7.77	7.93	461	(0.13, 0.11)	19
	4	3.2	7.28	7.65	462	(0.13, 0.12)	19
Cz-DICza	1	2.9	25.62	25.6	460	(0.14, 0.10)	18
	2	2.8	25.28	23.8	460	(0.14, 0.11)	18
	4	2.8	25.21	22.1	461	(0.14, 0.11)	18
Cz-DICz^b	—	2.5	8.6	9.4	460	(0.13, 0.09)	15
DiICzMes4	—	5.2	—	3.0 (1.9/—)	446	(0.15, 0.11)	—	[26]
p-FLDID	1	3.5	11.2	18.7	452	(0.147, 0.058)	23	[33]
BisICz	1	—	2.9	6.5	437	(0.16, 0.04)	24	[16]
tBisICz	1	—	8.4	15.1	445	(0.16, 0.05)	22
tPBisICz	1	—	13.5	23.1	452	(0.15, 0.05)	21
pICz-PPO^a	1	3.6	8.7	12.1 (7.1/—)	442	(0.16, 0.08)	20	[35]
pICz-2PPO^a	1	3.6	12.6	17.7 (12.8/—)	441	(0.16, 0.07)	19
tBisICz-DPA	1	—	11.0	20.0	448	(0.15, 0.05)	28	[43]
	3	—	12.3	20.4	452	(0.15, 0.05)	28
	5	—	12.1	19.5	453	(0.15, 0.06)	29
tBisICz-PhCz	1	—	8.5	19.7	445	(0.17, 0.05)	20
	3	—	11.6	24.9	446	(0.16, 0.04)	19
	5	—	7.7	16.6	447	(0.15, 0.04)	19
pICz^c		3.5	30.1	32.0 (6.7/—)	445	(0.15, 0.10)	—	[45]
pICz-TPA^c		3.6	31.5	34.7 (11.2/—)	445	(0.15, 0.085)	—
DPA-bisICZ		2.5	—	24.4	508	(0.17, 0.66)	34	[46]
tBuDPA-bisICZ		2.9	—	24.7	514	(0.20, 0.68)	35
MeODPA-bisICZ		2.1	—	22.6	532	(0.31, 0.65)	40
2,5-tDPAtDIDCz^d	1	3.7 (@1.0 cd•m^－2)	24.2	23.4	464	(0.13, 0.12)	36	[47]
2,5-tDPAtDIDCz^e	1	4.1 (@1.0 cd•m^－2)	34.1	30.8	466	(0.13, 0.14)	38
1,6-tDPAtDIDCz^d	1	3.5 (@1.0 cd•m^－2)	3.4	6.4	437	(0.16, 0.04)	32
1,6-tDPAtDIDCz^e	1	3.9 (@1.0 cd•m^－2)	8.7	7.3	438	(0.16, 0.05)	36
tBu-TiTAT		6.0	7.8	6.3 (4.1/2.6)	454	(0.14, 0.14)		[49]
tBu-TiTAT^c		6.0	19.6	12.6 (7.1/5.7)	454	(0.16, 0.19)	55
α-NAICZ	—	2.3	27.4	20.2 (—/19.6), 18.6^f	610	(0.65, 0.35)	38	[53]
α-EtNAICZ	—	2.2	5.7	6.3 (—/4.5), 3.9^f	631	(0.51, 0.39)	44
NBisICz	5% TTF	6.1	7.9	7.1 (—/6.9)	469	(0.127, 0.148)	48.4	[56]
NBisICz-PCz	2% PSF	7.2	16.6	18.8 (—/5.5)	453	(0.143, 0.076)	22
NBisICz-DPA	2% PSF	6.6	19.1	20.6 (—/7.9)	454	(0.141, 0.085)	27.5
ββICZ^a	1	2.4	100.9	30.9 (—/28.9), 23.2^f	508	(0.22, 0.64)	19	[58]
ββCNICZ^a	1	2.6	87.3	27.0 (—/25.5), 18.6^f	509	(0.21, 0.65)	19
t-mp3ICz	1	V_d-5.7	12.2	24.3	446	(0.154, 0.044)	21	[61]
p-mp3ICz	1	V_d-5.7	16.1	24.2	451	(0.147, 0.061)	23
	1	V_d-5.3	18.8	26.8	452	(0.142, 0.061)	25
t3IDCz	1	6.9 (@1000 cd•m^－2)	36.9	30.0	472	(0.119, 0.161)	25	[64]
t3IDC^g	1	6.9 (@100 cd•m^－2)	35.4	30.9	471	(0.116, 0.158)	26
p3IDCz	1	6.9 (@1000 cd•m^－2)	37.9	30.9	472	(0.120, 0.158)	23
p3IDCz^g	1	6.9 (@100 cd•m^－2)	43.4	33.8	473	(0.111, 0.188)	28
p3IDCz^h	1	6.9 (@100 cd•m^－2)	42.6	30.5	474	(0.116, 0.213)	33
IDCz-DBS	—	—	—	31.1	461	(0.135, 0.160)	21	[66]

基于吲哚并[3,2,1-jk]咔唑的多重共振型发光分子研究进展