Research Progress of Circularly Polarized Thermally Activated Delayed Fluorescence Materials and Devices

doi:10.6023/cjoc202208023

Abstract

Circularly polarized thermally activated delayed fluorescence (CP-TADF) materials have the characteristics of easily modified molecular structure, high exciton utilization and circularly polarized luminescence, which are the promising luminescent materials for the application of optical information storage, 3D displays, light-emitting devices and data encryption. The circular-polarized organic light-emitting diodes (CP-OLED) prepared by using such materials as emitting layers can simultaneously achieve high luminescence dissymmetry factor and theoretical 100% exciton utilization, which is crucial for the development of low-power and high-performance OLED. Recently, through the design and optimization of molecular structure, electroluminescence efficiency of CP-TADF materials were improved, but the problems of low luminescence dissymmetry factor and serious efficiency roll-off still existed. On this basis, the reported CP-TADF materials is reviewed and the relationship between the design strategies of molecular structure and the characters of excellent photophysical properties, circular polarization properties and electroluminescent properties is summaried. Furthermore, the preparation of high-perfor- mance of CP-TADF materials and their applications in OLEDs are prospected.

Key words: chiral organic luminescent material, circularly polarized light, thermally activated delayed fluorescence, organic light-emitting diode

Cite this article

Xiaodong Yang, Xiaokang Zheng, Hailiang Dong, Jing Sun, Hua Wang. Research Progress of Circularly Polarized Thermally Activated Delayed Fluorescence Materials and Devices[J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1292-1309.

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Compound	λ_PL/nm	Host/[ω(emitter)/%]	ΔE_ST/eV	τ_d/μs	PLQY/%	\|g_lum\|/10^－3	λ_EL/nm	EQE/%	\|g_EL\|/10^－3	Ref.
1	519^a	mCP (9)	0.14^b	–	26%^a	1.1^b	–	–	–	[28]
2	533^c	mCBP (15)	0.06^a	130^a	98^a	1.1^a	520	19.8	2.3	[29]
3	597^b	CBP (6)	0.07^a	37.4^a	39.9^a	0.92^a	592	12.4	–	[30]
4	512^b	mCBP (30)	0.052^b	6.78^a	53.1^a	2.2^b	508	12.5	1.3	[31]
5	512^b	mCBP (30)	0.053^b	7.98^a	89.0^a	3.4^b	508	23.1	1.0	[31]
6	470^b	DPEPO (25)	0.022^b	4.7^a	81.2^a	3.0^b	472	20.0	3.1	[32]
7	473^a	mCPCN (12)	0.19^a	2.3^b	89^a	0.59^b	494	20.3	0.74	[35]
8	565^a	mCPCN (6)	0.22^a	9.7^b	86^a	2.0^b	591	23.7	2.4	[35]
9	451^a	DPEPO (12)	0.05^a	3.4^a	86^a	0.3^b	458	18.5	–	[36]
10	541^c	–	0.03^c	1.1^c	85^c	1.9^c	534	25.5	1.5	[38]
11	497^b	DMIC-TRZ (1)	0.01^b	28.1^a	96^a	0.25^b	504	37.2	0.27	[41]
12	517^b	mCP (20)	–	2.9^b	53^b	1.3^b	540	9.1	–	[49]
13	493^a	mCP (10)	0.15^b	24.3^a	32^a	1.2^b	496	9.3	60	[50]
14	571^a	mCP (10)	0.11^b	1.07^a	38^a	0.5^b	571	1.7	91	[50]
15	534^a	mCP (10)	0.11^b	2.51^a	12.5^a	1.1^b	527	6.3	63	[50]
16	540^a	mCP (10)	0.02^b	1.77^a	45^a	0.7^b	547	3.5	82	[50]
17	516^a	mCP (10)	0.08^g	15^a	20^a	0.37^c	496	10.1	3.7	[51]
18	529^a	mCP (10)	0.03^g	8^a	55^a	0.58^c	516	10.6	3.9	[51]
19	568^a	TCTA (15)	0.059^b	1.03^a	18.5^a	1.6^b	580	1.8	1.0	[52]
20	600^a	mCP (10)	0.14^b	5.5^a	15.8^a	2.2^b	600	2.0	2.1	[53]
21	469^b	–	0.054^f	10^a	7^a	2.1^b	–	–	–	[54]
22	490^b	–	0.051^f	45^a	16^a	1.6^b	–	–	–	[54]
23	506^b	–	0.017^f	39^a	18^a	0.2^b	–	–	–	[54]
24	516^b	–	0.022^f	16^a	30^a	<0.1^b	–	–	–	[54]
25	481^b	–	0.013^f	6^a	29^a	1.1^b	–	–	–	[54]
26	504^b	–	0.053^f	19^a	46^a	1.0^b	–	–	–	[54]
27	510^b	mCP	0.009^f	17^a	42^a	1.1^b	510	0.8	1.0	[54]
28	493^b	–	0.136^f	18^a	25^a	<0.1^b	–	–	–	[54]
29	511^b	–	0.07^f	40^a	31^a	<0.1^b	–	–	–	[54]
30	519^b	–	0.075^f	22^a	47^a	0.7^b	–	–	–	[54]
31	612^b	–	–	0.46^h	5.3^h	0.31^h	–	–	–	[55]
32	670^c	–	0.28^b	0.9^b	1^c	0.25^d	716	1.9	–	[56]
33	662^c	–	0.23^b	1.2^b	2^c	0.15^d	700	0.7	–	[59]
34	537^a	TCTA (8)	0.18^b	170^a	86^a	0.3^b	530	27.6	–	[57]
35	503^a	2,6-DCzPPy (8)	0.12^b	75^a	77^a	5.3^b	506	20.5	–	[57]
36	503^b	2,6-DCzPPy (10)	0.037^b	7.7^a	92^a	0.56^b	501	32.6	2.34	[59]
37	538^b	2,6-DCzPPy (10)	0.09^b	13.5^a	85^a	1.88^b	544	12.3	2.3	[60]
38	504^b	mCP (15)	0.04^b	3.2^a	73^a	0.7^b	502	15.0	0.8	[64]
39	520^b	mCP (15)	0.05^b	2.7^a	87^a	0.39^b	514	20.3	0.5	[64]
40	589^b	CBP (15)	0.16^b	3.6^a	92^a	1.9^b	548	28.3	0.6	[65]
41	630^b	CBP (7)	0.07^b	3.7^a	89^a	0.4^b	600	20.3	2.4	[65]
42	509^a	mCBP (13)	0.08^c	4.0^a	81^a	2.6^b	514	19.0	0.47	[72]
43	493^b	PhCzBCz (3)	0.12^b	95.3^a	99^b	0.91^a	496	29.4	1.4	[73]
44	500^b	PhCzBCz (3)	0.13^b	97.4^a	96^b	1.04^a	508	24.5	0.46	[73]
45	505^c	CBP (25)	0.067^c	12.9^a	79.7^c	2.2^b	522	17.1	1.5	[76]
46	458^b	DPEPO (20)	0.029^a	12.6^a	68.2^a	4.8^a	468	12.7	14	[77]
47	497^b	DPEPO (25)	0.05^a	4.0^a	74^a	5.4^b	500	20.8	–	[78]
48	543^b	2,6-DCzPPy (8)	0.04^b	1.1^b	86.1^b	9.7^b	537	17.8	–	[79]
49	485^a	DPEPO (25)	0.09^b	6.4^a	64^a	7.09^b	483	16.7	5.5	[80]
50	482^a	DPEPO (25)	0.05^b	7.0^a	76^a	5.05^b	480	18.3	3.8	[80]
51	529^b	mCP (1)	0.00^f	0.78^a	11^b	0.7	–	–	–	[81]
52	530^b	mCP (1)	0.00^f	0.95^a	29^b	2.0	–	–	–	[81]
53	492^b	mCP (1)	0.22^f	0.57^a	23^b	0.8	–	–	–	[81]
54	482^a	DPEPO (10)	0.16^a	65^a	70^a	1.3^b	480	17.0	–	[84]
55	527^a	CBP (10)	0.03^b	12.1^a	60^a	2.3^b	560	7.8	4.3	[85]
56	565^b	CBP (10)	0.19^f	75^a	78^a	1.9^b	557	20.1	1.5	[86]
57	522^a	mCPCN (3)	0.14^b	8.3^b	96^a	1.5^b	510	20.6	3.7	[88]
58	512^a	mCPCN (1)	0.14^b	23.1^b	92^a	1.5^b	506	26.5	1.9	[88]
59	660^b	–	0.22^b	16.4^b	100^b	2.0^e	–	–	–	[89]
60	684^b	–	0.21^b	43.9^b	99^b	2.0^e	–	–	–	[89]
61	696^b	–	0.18^b	26.8^b	90^b	1.5^e	–	–	–	[89]
62	461^b	mCBP (5)	0.11^b	40.3^a	46.6^a	1.1^b	467	14.0	1.5	[90]
63	446^b	DPEPO (18)	0.23^b	536^a	51.0^a	1.2^e	488	10.6	1.6	[91]
64	473^b	mCP (1)	0.15^a	4.37^a	4.1^a	0.4^b	–	–	–	[92]
65	539^c	CBP (5)	–	1.35^c	6.7^c	2.01^c	529	0.37	–	[94]
66	542^c	CBP (5)	–	1.37^c	10.3^c	1.39^c	528	0.87	–	[94]
67	487^a	mCP (15)	0.03^a	1.07^a	63^a	1.4^a	496	12.0	1.1	[95]
68	532^a	mCP (10)	0.01^a	1.75^a	92^a	1.0^a	534	22.1	1.0	[95]
69	547^b	mCP (10)	0.061^f	2.3^a	76^a	1.9^a	544	15.8	1.6	[96]

Compound	λ_PL/nm	Host/[ω(emitter)/%]	ΔE_ST/eV	τ_d/μs	PLQY/%	\|g_lum\|/10^－3	λ_EL/nm	EQE/%	\|g_EL\|/10^－3	Ref.
1	519^a	mCP (9)	0.14^b	–	26%^a	1.1^b	–	–	–	[28]
2	533^c	mCBP (15)	0.06^a	130^a	98^a	1.1^a	520	19.8	2.3	[29]
3	597^b	CBP (6)	0.07^a	37.4^a	39.9^a	0.92^a	592	12.4	–	[30]
4	512^b	mCBP (30)	0.052^b	6.78^a	53.1^a	2.2^b	508	12.5	1.3	[31]
5	512^b	mCBP (30)	0.053^b	7.98^a	89.0^a	3.4^b	508	23.1	1.0	[31]
6	470^b	DPEPO (25)	0.022^b	4.7^a	81.2^a	3.0^b	472	20.0	3.1	[32]
7	473^a	mCPCN (12)	0.19^a	2.3^b	89^a	0.59^b	494	20.3	0.74	[35]
8	565^a	mCPCN (6)	0.22^a	9.7^b	86^a	2.0^b	591	23.7	2.4	[35]
9	451^a	DPEPO (12)	0.05^a	3.4^a	86^a	0.3^b	458	18.5	–	[36]
10	541^c	–	0.03^c	1.1^c	85^c	1.9^c	534	25.5	1.5	[38]
11	497^b	DMIC-TRZ (1)	0.01^b	28.1^a	96^a	0.25^b	504	37.2	0.27	[41]
12	517^b	mCP (20)	–	2.9^b	53^b	1.3^b	540	9.1	–	[49]
13	493^a	mCP (10)	0.15^b	24.3^a	32^a	1.2^b	496	9.3	60	[50]
14	571^a	mCP (10)	0.11^b	1.07^a	38^a	0.5^b	571	1.7	91	[50]
15	534^a	mCP (10)	0.11^b	2.51^a	12.5^a	1.1^b	527	6.3	63	[50]
16	540^a	mCP (10)	0.02^b	1.77^a	45^a	0.7^b	547	3.5	82	[50]
17	516^a	mCP (10)	0.08^g	15^a	20^a	0.37^c	496	10.1	3.7	[51]
18	529^a	mCP (10)	0.03^g	8^a	55^a	0.58^c	516	10.6	3.9	[51]
19	568^a	TCTA (15)	0.059^b	1.03^a	18.5^a	1.6^b	580	1.8	1.0	[52]
20	600^a	mCP (10)	0.14^b	5.5^a	15.8^a	2.2^b	600	2.0	2.1	[53]
21	469^b	–	0.054^f	10^a	7^a	2.1^b	–	–	–	[54]
22	490^b	–	0.051^f	45^a	16^a	1.6^b	–	–	–	[54]
23	506^b	–	0.017^f	39^a	18^a	0.2^b	–	–	–	[54]
24	516^b	–	0.022^f	16^a	30^a	<0.1^b	–	–	–	[54]
25	481^b	–	0.013^f	6^a	29^a	1.1^b	–	–	–	[54]
26	504^b	–	0.053^f	19^a	46^a	1.0^b	–	–	–	[54]
27	510^b	mCP	0.009^f	17^a	42^a	1.1^b	510	0.8	1.0	[54]
28	493^b	–	0.136^f	18^a	25^a	<0.1^b	–	–	–	[54]
29	511^b	–	0.07^f	40^a	31^a	<0.1^b	–	–	–	[54]
30	519^b	–	0.075^f	22^a	47^a	0.7^b	–	–	–	[54]
31	612^b	–	–	0.46^h	5.3^h	0.31^h	–	–	–	[55]
32	670^c	–	0.28^b	0.9^b	1^c	0.25^d	716	1.9	–	[56]
33	662^c	–	0.23^b	1.2^b	2^c	0.15^d	700	0.7	–	[59]
34	537^a	TCTA (8)	0.18^b	170^a	86^a	0.3^b	530	27.6	–	[57]
35	503^a	2,6-DCzPPy (8)	0.12^b	75^a	77^a	5.3^b	506	20.5	–	[57]
36	503^b	2,6-DCzPPy (10)	0.037^b	7.7^a	92^a	0.56^b	501	32.6	2.34	[59]
37	538^b	2,6-DCzPPy (10)	0.09^b	13.5^a	85^a	1.88^b	544	12.3	2.3	[60]
38	504^b	mCP (15)	0.04^b	3.2^a	73^a	0.7^b	502	15.0	0.8	[64]
39	520^b	mCP (15)	0.05^b	2.7^a	87^a	0.39^b	514	20.3	0.5	[64]
40	589^b	CBP (15)	0.16^b	3.6^a	92^a	1.9^b	548	28.3	0.6	[65]
41	630^b	CBP (7)	0.07^b	3.7^a	89^a	0.4^b	600	20.3	2.4	[65]
42	509^a	mCBP (13)	0.08^c	4.0^a	81^a	2.6^b	514	19.0	0.47	[72]
43	493^b	PhCzBCz (3)	0.12^b	95.3^a	99^b	0.91^a	496	29.4	1.4	[73]
44	500^b	PhCzBCz (3)	0.13^b	97.4^a	96^b	1.04^a	508	24.5	0.46	[73]
45	505^c	CBP (25)	0.067^c	12.9^a	79.7^c	2.2^b	522	17.1	1.5	[76]
46	458^b	DPEPO (20)	0.029^a	12.6^a	68.2^a	4.8^a	468	12.7	14	[77]
47	497^b	DPEPO (25)	0.05^a	4.0^a	74^a	5.4^b	500	20.8	–	[78]
48	543^b	2,6-DCzPPy (8)	0.04^b	1.1^b	86.1^b	9.7^b	537	17.8	–	[79]
49	485^a	DPEPO (25)	0.09^b	6.4^a	64^a	7.09^b	483	16.7	5.5	[80]
50	482^a	DPEPO (25)	0.05^b	7.0^a	76^a	5.05^b	480	18.3	3.8	[80]
51	529^b	mCP (1)	0.00^f	0.78^a	11^b	0.7	–	–	–	[81]
52	530^b	mCP (1)	0.00^f	0.95^a	29^b	2.0	–	–	–	[81]
53	492^b	mCP (1)	0.22^f	0.57^a	23^b	0.8	–	–	–	[81]
54	482^a	DPEPO (10)	0.16^a	65^a	70^a	1.3^b	480	17.0	–	[84]
55	527^a	CBP (10)	0.03^b	12.1^a	60^a	2.3^b	560	7.8	4.3	[85]
56	565^b	CBP (10)	0.19^f	75^a	78^a	1.9^b	557	20.1	1.5	[86]
57	522^a	mCPCN (3)	0.14^b	8.3^b	96^a	1.5^b	510	20.6	3.7	[88]
58	512^a	mCPCN (1)	0.14^b	23.1^b	92^a	1.5^b	506	26.5	1.9	[88]
59	660^b	–	0.22^b	16.4^b	100^b	2.0^e	–	–	–	[89]
60	684^b	–	0.21^b	43.9^b	99^b	2.0^e	–	–	–	[89]
61	696^b	–	0.18^b	26.8^b	90^b	1.5^e	–	–	–	[89]
62	461^b	mCBP (5)	0.11^b	40.3^a	46.6^a	1.1^b	467	14.0	1.5	[90]
63	446^b	DPEPO (18)	0.23^b	536^a	51.0^a	1.2^e	488	10.6	1.6	[91]
64	473^b	mCP (1)	0.15^a	4.37^a	4.1^a	0.4^b	–	–	–	[92]
65	539^c	CBP (5)	–	1.35^c	6.7^c	2.01^c	529	0.37	–	[94]
66	542^c	CBP (5)	–	1.37^c	10.3^c	1.39^c	528	0.87	–	[94]
67	487^a	mCP (15)	0.03^a	1.07^a	63^a	1.4^a	496	12.0	1.1	[95]
68	532^a	mCP (10)	0.01^a	1.75^a	92^a	1.0^a	534	22.1	1.0	[95]
69	547^b	mCP (10)	0.061^f	2.3^a	76^a	1.9^a	544	15.8	1.6	[96]

圆偏振热活化延迟荧光材料及其器件的研究进展