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

doi:10.6023/cjoc202503030

摘要/Abstract

综述了基于吲哚并[3,2,1-jk]咔唑(ICz)的多重共振型(MR)发光分子的研究进展. 吲哚并咔唑类MR分子因其独特的分子结构和优异的光电性能, 在有机发光二极管(OLED)领域展现出巨大的应用潜力. 首先介绍了吲哚并咔唑骨架的基本结构及其在MR发光分子中的应用优势, 然后详细讨论了延长共轭长度、外围基团修饰以及重原子效应等分子设计策略来优化其光电性能的方法. 研究表明, 通过多种分子设计策略的优化, 吲哚并咔唑类MR发光分子在提高发光效率和实现窄带发射方面取得了显著进展, 为MR类发光分子的发展提供了新的可能性. 此外, 通过合理的分子设计, 实现从紫外到红光的全色发光, 也为OLED技术的发展提供了新的思路. 最后, 总结了当前研究中存在的挑战, 并对未来的研究方向进行了展望.

关键词: 多重共振, 有机发光二极管, 发光材料, 吲哚并咔唑

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

引用此文

任志明, 谢立娟, 晋静, 吴玉洁, 刘迪, 李久艳. 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[J]. 有机化学, 2025, 45(11): 4108-4127.

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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参考文献 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]