Recent Advances in Multi-Resonance Thermally Activated Delayed Fluorescence Materials Based on B,N-Heteroarenes

doi:10.6023/cjoc202212037

Abstract

In recent years, multi-resonance thermally activated delayed fluorescence (MR-TADF) materials have attracted wide attention because of their excellent photophysical properties and electroluminescent performance. By introducing electron-deficient and electron-rich centers (such as boron and nitrogen atoms) in the framework of polycyclic aromatic hydrocarbons (PAHs), the HOMO and LUMO can be separated on different atoms due to the opposite resonance effects, which can reduce the singlet-triplet energy gap (ΔE_ST) to achieve TADF properties. Compared with conventional donor-acceptor type TADF materials, MR-TADF materials have rigid skeletons and show short-range charge transfer characteristics, which are conducive to realizing narrowband luminescence with high color purity and high quantum efficiency, making them ideal luminescent materials and widely used in organic light-emitting diodes (OLEDs). Since the first report of MR-TADF materials based on B,N-heteroarenes in 2016, significant progress has been achieved in the development of new materials. However, a timely summary on this topic is still lacking. In this review, the design strategy and synthetic method of MR-TADF materials based on B,N-heteroarenes are summarized, and the recent advances in the development of new molecular skeletons, the backbone modification strategy to tune the properties, and a novel type of chiral MR-TADF materials are discussed. It is expected that the current review would further promote the development and application of MR-TADF materials in the future.

Key words: multi-resonance, thermally activated delayed fluorescence, organic light-emitting diodes, B,N-heteroarenes, narrowband luminescence

Cite this article

Yi Zhang, Cheng-Zhuo Du, Ji-Kun Li, Xiao-Ye Wang. Recent Advances in Multi-Resonance Thermally Activated Delayed Fluorescence Materials Based on B,N-Heteroarenes[J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1645-1690.

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Emitter	λ_PL/nm (sol/film)	FWHM_PL/nm (sol/film)	PLQY/% (sol/film)	ΔE_ST/eV	k_RISC/ (×10⁵ s^–1)	λ_EL/nm	FWHM_EL/nm	EQE/%	CIE	Ref.
3	462/—	33/—	89/—	0.20	0.10	459	28	13.5	(0.13, 0.09)	[11]
6a	479/—	30/—	87/—	0.12	0.17	480	35	14.7	—	[14]
6b	497/—	28/—	86/—	0.11	0.15	490	32	16.3	—	[14]
6b	481/—	22/—	91/—	0.13	0.15	488	29	21.6	(0.01, 0.42)	[15]
9	466/—	16/—	93/—	0.15	0.19	469	27	29.3	(0.12, 0.18)	[16]
12a	662/—	38/—	100/—	0.18	0.67	664	48	25.6	(0.72, 0.28)	[17]
12b	692/—	38/—	100/—	0.16	0.25	686	49	24.7	(0.72, 0.28)	[17]
12c	696/—	—	90/—	0.18	0.30	—	—	—	—	[18]
14	460/461	23/30	83/89	0.12	0.58	461	28	19.0	(0.13, 0.13)	[19]
17a	485/—	29/—	63/—	0.14	0.96	502	48	21.1	(0.14, 0.54)	[20]
17b	490/—	30/—	86/—	0.11	1.26	504	48	28.2	(0.14, 0.56)	[20]
19	475/—	23/—	66/—	0.39	0.46	480	31	9.0	(0.13, 0.26)	[21]
21	558/—	38/—	99/—	0.12	0.78	588	61	39.2	(0.54, 0.45)	[22]
24a	523/527	21/23	98/—	0.04	—	527	24	29.3	(0.21, 0.75)	[23]
24b	531/535	21/25	93/—	0.04	—	535	26	26.2	(0.26, 0.72)	[23]
27	509/—	22/—	87/—	0.013	1.20	512	25	31.1	(0.13, 0.73)	[24]
30	467/479	23/31	98/—	0.11	0.12	475	34	23.6	(0.14, 0.30)	[25]
33a	504/—	39/—	87/—	0.06	0.51	497	29	26.7	(0.12, 0.57)	[26]
33b	483/—	38/—	88/—	0.11	0.31	—	—	—	—	[26]
37	468/475	26/34	90/95	0.15	0.48	472	34	23.7	(0.12, 0.19)	[27]
40	615/—	21/—	89/—	0.19	0.12	616	26	22.0	(0.67, 0.33)	[16]
42	521/—	21/—	99/—	0.22	0.29	523	23	30.5	(0.22, 0.74)	[28]
45	461/465	22/26	93/—	0.20	0.27	466	26	26.4	(0.13, 0.11)	[29]
47	456/462	22/26	93/—	0.20	0.28	463	26	28.0	(0.13, 0.09)	[29]
49	533/—	20/—	99/—	0.26	0.78	541	27	31.5	(0.30, 0.58)	[30]
50	542/—	18/—	99/—	0.20	0.70	551	23	37.4	(0.36, 0.59)	[30]
53	512/—	20/—	92/—	0.06	1.7	520	29	35.2	(0.19, 0.74)	[31]
56	522/—	28/—	94/—	0.18	0.08	527	30	28.2	(0.27, 0.69)	[32]
59	487/—	27/—	92/—	0.12	9.3	502	33	28.0	(0.12, 0.62)	[33]
62	500/—	29/—	93/—	0.09	3.0	491	29	26.1	(0.09, 0.41)	[33]
65	523/—	34/—	96/—	0.14	0.21	528	36	35.1	(0.26, 0.70)	[34]
68a	496/—	34/—	98/—	0.06	10.0	499	38	31.7	(0.14, 0.56)	[35]
68b	521/—	29/—	98/—	<0.01	9.0	524	37	32.2	(0.22, 0.71)	[35]
70	455/—	32/—	53/—	0.19	0.09	460	37	18.3	(0.13, 0.11)	[36]
74	468/467	18/—	82/—	0.017	2.01	469	18	34.4	(0.12, 0.11)	[37]
76a	484/—	16/—	76/—	0.005	4.4	480	27	22.9	(0.09, 0.21)	[38]
76b	481/—	17/—	90/—	0.009	5.7	483	17	26.2	(0.09, 0.27)	[39]
76c	464/—	16/—	81/—	0.005	6.5	468	15	26.6	(0.12, 0.10)	[39]
78	454/—	18/—	91/—	0.20	0.13	457	28	31.2	(0.14, 0.08)	[40]
79	450/—	15/—	93/—	0.16	0.26	467	23	33.2	(0.13, 0.11)	[40]
80	444/—	17/—	98/—	0.15	2.55	458	23	37.6	(0.14, 0.08)	[40]
82	450/455	19/26	100/95	0.21	0.18	452	25	26.6	(0.14, 0.08)	[41]
85a	482/—	33/—	89/—	0.19	0.08	481	32	16.2	(0.10, 0.27)	[42]
85b	479/—	34/—	88/—	0.20	0.09	480	33	21.4	(0.11, 0.29)	[42]
91	432/—	31/—	82/—	0.29	0.04	431	42	19.4	(0.16, 0.05)	[44]
94	431/—	33/—	68/—	0.31	0.05	431	42	13.5	(0.16, 0.05)	[44]
97	471/—	41/—	96/—	0.15	0.03	466	48	39.8	(0.14, 0.16)	[44]
100	539/—	30/—	85/—	0.35	—	535	30	31.0	(0.33, 0.64)	[44]
103	420/—	29/—	86/—	0.37	0.001	—	—	—	—	[46]
105	417/—	25/—	86/—	0.30	0.002	423	31	9.1	(0.17, 0.04)	[46]
108a	514/—	82/—	92/—	0.20	2.90	507	—	9.9	(0.27, 0.49)	[47]
108b	517/—	89/—	89/—	0.16	4.67	507	—	11.5	(0.28, 0.48)	[47]
111a	567/—	97/—	64/—	0.19	2.10	547	—	19.9	(0.40, 0.57)	[47]
111b	584/—	108/—	61/—	0.17	2.44	554	—	25.1	(0.41, 0.56)	[47]
112	694/—	151/—	1/—	—	—	—	—	—	—	[47]
115a	481/483	29/28	93/91	0.10	0.02	479	27	36.0	(0.12, 0.27)	[48]
115b	491/491	34/33	91/90	0.13	0.14	485	33	33.4	(0.11, 0.32)	[48]

Emitter	λ_PL/nm (sol/film)	FWHM_PL/nm (sol/film)	PLQY/% (sol/film)	ΔE_ST/eV	k_RISC/ (×10⁵ s^–1)	λ_EL/nm	FWHM_EL/nm	EQE/%	CIE	Ref.
3	462/—	33/—	89/—	0.20	0.10	459	28	13.5	(0.13, 0.09)	[11]
6a	479/—	30/—	87/—	0.12	0.17	480	35	14.7	—	[14]
6b	497/—	28/—	86/—	0.11	0.15	490	32	16.3	—	[14]
6b	481/—	22/—	91/—	0.13	0.15	488	29	21.6	(0.01, 0.42)	[15]
9	466/—	16/—	93/—	0.15	0.19	469	27	29.3	(0.12, 0.18)	[16]
12a	662/—	38/—	100/—	0.18	0.67	664	48	25.6	(0.72, 0.28)	[17]
12b	692/—	38/—	100/—	0.16	0.25	686	49	24.7	(0.72, 0.28)	[17]
12c	696/—	—	90/—	0.18	0.30	—	—	—	—	[18]
14	460/461	23/30	83/89	0.12	0.58	461	28	19.0	(0.13, 0.13)	[19]
17a	485/—	29/—	63/—	0.14	0.96	502	48	21.1	(0.14, 0.54)	[20]
17b	490/—	30/—	86/—	0.11	1.26	504	48	28.2	(0.14, 0.56)	[20]
19	475/—	23/—	66/—	0.39	0.46	480	31	9.0	(0.13, 0.26)	[21]
21	558/—	38/—	99/—	0.12	0.78	588	61	39.2	(0.54, 0.45)	[22]
24a	523/527	21/23	98/—	0.04	—	527	24	29.3	(0.21, 0.75)	[23]
24b	531/535	21/25	93/—	0.04	—	535	26	26.2	(0.26, 0.72)	[23]
27	509/—	22/—	87/—	0.013	1.20	512	25	31.1	(0.13, 0.73)	[24]
30	467/479	23/31	98/—	0.11	0.12	475	34	23.6	(0.14, 0.30)	[25]
33a	504/—	39/—	87/—	0.06	0.51	497	29	26.7	(0.12, 0.57)	[26]
33b	483/—	38/—	88/—	0.11	0.31	—	—	—	—	[26]
37	468/475	26/34	90/95	0.15	0.48	472	34	23.7	(0.12, 0.19)	[27]
40	615/—	21/—	89/—	0.19	0.12	616	26	22.0	(0.67, 0.33)	[16]
42	521/—	21/—	99/—	0.22	0.29	523	23	30.5	(0.22, 0.74)	[28]
45	461/465	22/26	93/—	0.20	0.27	466	26	26.4	(0.13, 0.11)	[29]
47	456/462	22/26	93/—	0.20	0.28	463	26	28.0	(0.13, 0.09)	[29]
49	533/—	20/—	99/—	0.26	0.78	541	27	31.5	(0.30, 0.58)	[30]
50	542/—	18/—	99/—	0.20	0.70	551	23	37.4	(0.36, 0.59)	[30]
53	512/—	20/—	92/—	0.06	1.7	520	29	35.2	(0.19, 0.74)	[31]
56	522/—	28/—	94/—	0.18	0.08	527	30	28.2	(0.27, 0.69)	[32]
59	487/—	27/—	92/—	0.12	9.3	502	33	28.0	(0.12, 0.62)	[33]
62	500/—	29/—	93/—	0.09	3.0	491	29	26.1	(0.09, 0.41)	[33]
65	523/—	34/—	96/—	0.14	0.21	528	36	35.1	(0.26, 0.70)	[34]
68a	496/—	34/—	98/—	0.06	10.0	499	38	31.7	(0.14, 0.56)	[35]
68b	521/—	29/—	98/—	<0.01	9.0	524	37	32.2	(0.22, 0.71)	[35]
70	455/—	32/—	53/—	0.19	0.09	460	37	18.3	(0.13, 0.11)	[36]
74	468/467	18/—	82/—	0.017	2.01	469	18	34.4	(0.12, 0.11)	[37]
76a	484/—	16/—	76/—	0.005	4.4	480	27	22.9	(0.09, 0.21)	[38]
76b	481/—	17/—	90/—	0.009	5.7	483	17	26.2	(0.09, 0.27)	[39]
76c	464/—	16/—	81/—	0.005	6.5	468	15	26.6	(0.12, 0.10)	[39]
78	454/—	18/—	91/—	0.20	0.13	457	28	31.2	(0.14, 0.08)	[40]
79	450/—	15/—	93/—	0.16	0.26	467	23	33.2	(0.13, 0.11)	[40]
80	444/—	17/—	98/—	0.15	2.55	458	23	37.6	(0.14, 0.08)	[40]
82	450/455	19/26	100/95	0.21	0.18	452	25	26.6	(0.14, 0.08)	[41]
85a	482/—	33/—	89/—	0.19	0.08	481	32	16.2	(0.10, 0.27)	[42]
85b	479/—	34/—	88/—	0.20	0.09	480	33	21.4	(0.11, 0.29)	[42]
91	432/—	31/—	82/—	0.29	0.04	431	42	19.4	(0.16, 0.05)	[44]
94	431/—	33/—	68/—	0.31	0.05	431	42	13.5	(0.16, 0.05)	[44]
97	471/—	41/—	96/—	0.15	0.03	466	48	39.8	(0.14, 0.16)	[44]
100	539/—	30/—	85/—	0.35	—	535	30	31.0	(0.33, 0.64)	[44]
103	420/—	29/—	86/—	0.37	0.001	—	—	—	—	[46]
105	417/—	25/—	86/—	0.30	0.002	423	31	9.1	(0.17, 0.04)	[46]
108a	514/—	82/—	92/—	0.20	2.90	507	—	9.9	(0.27, 0.49)	[47]
108b	517/—	89/—	89/—	0.16	4.67	507	—	11.5	(0.28, 0.48)	[47]
111a	567/—	97/—	64/—	0.19	2.10	547	—	19.9	(0.40, 0.57)	[47]
111b	584/—	108/—	61/—	0.17	2.44	554	—	25.1	(0.41, 0.56)	[47]
112	694/—	151/—	1/—	—	—	—	—	—	—	[47]
115a	481/483	29/28	93/91	0.10	0.02	479	27	36.0	(0.12, 0.27)	[48]
115b	491/491	34/33	91/90	0.13	0.14	485	33	33.4	(0.11, 0.32)	[48]

Emitter	λ_PL/nm (sol/film)	FWHM_PL/nm (sol/film)	PLQY/% (sol/film)	ΔE_ST/eV	k_RISC/(10⁵ s^–1)	λ_EL/nm	FWHM_EL/nm	EQE/%	CIE	Ref.
119	433/—	28/—	86/—	0.18	0.08	443	32	16.3	(0.15, 0.05)	[49]
121	462/470	34/41	99/—	0.23	0.14	472	41	20.4	(0.13, 0.19)	[50]
123a	504/515	34/40	78/84	0.19	1.03	522	60	17.7	(0.28, 0.64)	[51]
123b	510/519	39/44	58/80	0.18	1.17	528	58	25.5	(0.28, 0.65)	[51]
126a	510/524	37/50	84/91	0.11	0.81	520	54	27.6	(0.26, 0.65)	[52]
126b	505/512	38/48	87/96	0.09	1.05	516	56	32.8	(0.24, 0.63)	[52]
128a	445/448	26/29	98/99	0.15	0.09	448	30	16.3	(0.15, 0.05)	[53]
128b	471/472	28/30	99/98	0.11	4.0	474	31	29.1	(0.11, 0.16)	[53]
128c	477/479	33/34	98/98	0.12	1500	481	33	30.1	(0.10, 0.24)	[53]
131a	505/520	—	99/—	0.12	6.0	515	50	35.7	(0.22, 0.66)	[54]
131b	502/514	—	100/—	0.14	20.0	512	48	36.8	(0.19, 0.66)	[54]
133	490/—	41/—	98/—	0.16	1.11	489	47	32.7	(0.14, 0.41)	[55]
136a	483/—	41/—	95/—	0.15	4.51	478	48	34.8	(0.15, 0.29)	[55]
136b	468/—	30/—	98/—	0.17	1.08	468	46	32.0	(0.15, 0.24)	[55]
139	461/464	19/24	90/—	0.029	1.6	465	23	29.5	(0.13, 0.10)	[56]
142	441/445	15/18	76/64	0.15	0.7	445	18	16.6	(0.15, 0.04)	[57]
145	460/464	20/22	93/88	0.144	8.8	463	22	32.2	(0.13, 0.08)	[57]
148	453/457	21/24	94/93	0.159	4.3	455	23	33.1	(0.14, 0.06)	[12b]
151	445/—	19/—	88/—	0.05	2.51	455	29	30.7	(0.14, 0.06)	[58]
154	473/378	21/24	58/89	0.13	15.0	478	25	27.8	(0.11, 0.22)	[59]
157	405/410	40/38	33/71	0.31	0.04	412	41	11.2	(0.18, 0.07)	[60]
159	456/—	17/—	94/—	0.06	0.31	466	21	24.2	(0.13, 0.10)	[61]
161a	505/—	20/—	98/—	0.13	0.8	510	29	26.7	(0.17, 0.68)	[62]
161b	553/—	28/—	98/—	0.13	1.9	556	43	21.8	(0.42, 0.57)	[62]
164a	605/610	32/35	96/—	0.25	—	610	39	35.6	(0.64, 0.34)	[63]
164b	609/618	32/37	95/—	0.27	—	618	39	34.4	(0.65, 0.35)	[63]
164c	616/624	33/38	96/—	0.26	—	625	40	36.1	(0.66, 0.33)	[63]
166a	631/—	40/—	80/—	0.20	2.1	613	66	5.8	(0.64, 0.34)	[64]
166b	641/—	39/—	85/—	0.19	2.2	616	65	7.8	(0.65, 0.34)	[64]

Emitter	λ_PL/nm (sol/film)	FWHM_PL/nm (sol/film)	PLQY/% (sol/film)	ΔE_ST/eV	k_RISC/(10⁵ s^–1)	λ_EL/nm	FWHM_EL/nm	EQE/%	CIE	Ref.
119	433/—	28/—	86/—	0.18	0.08	443	32	16.3	(0.15, 0.05)	[49]
121	462/470	34/41	99/—	0.23	0.14	472	41	20.4	(0.13, 0.19)	[50]
123a	504/515	34/40	78/84	0.19	1.03	522	60	17.7	(0.28, 0.64)	[51]
123b	510/519	39/44	58/80	0.18	1.17	528	58	25.5	(0.28, 0.65)	[51]
126a	510/524	37/50	84/91	0.11	0.81	520	54	27.6	(0.26, 0.65)	[52]
126b	505/512	38/48	87/96	0.09	1.05	516	56	32.8	(0.24, 0.63)	[52]
128a	445/448	26/29	98/99	0.15	0.09	448	30	16.3	(0.15, 0.05)	[53]
128b	471/472	28/30	99/98	0.11	4.0	474	31	29.1	(0.11, 0.16)	[53]
128c	477/479	33/34	98/98	0.12	1500	481	33	30.1	(0.10, 0.24)	[53]
131a	505/520	—	99/—	0.12	6.0	515	50	35.7	(0.22, 0.66)	[54]
131b	502/514	—	100/—	0.14	20.0	512	48	36.8	(0.19, 0.66)	[54]
133	490/—	41/—	98/—	0.16	1.11	489	47	32.7	(0.14, 0.41)	[55]
136a	483/—	41/—	95/—	0.15	4.51	478	48	34.8	(0.15, 0.29)	[55]
136b	468/—	30/—	98/—	0.17	1.08	468	46	32.0	(0.15, 0.24)	[55]
139	461/464	19/24	90/—	0.029	1.6	465	23	29.5	(0.13, 0.10)	[56]
142	441/445	15/18	76/64	0.15	0.7	445	18	16.6	(0.15, 0.04)	[57]
145	460/464	20/22	93/88	0.144	8.8	463	22	32.2	(0.13, 0.08)	[57]
148	453/457	21/24	94/93	0.159	4.3	455	23	33.1	(0.14, 0.06)	[12b]
151	445/—	19/—	88/—	0.05	2.51	455	29	30.7	(0.14, 0.06)	[58]
154	473/378	21/24	58/89	0.13	15.0	478	25	27.8	(0.11, 0.22)	[59]
157	405/410	40/38	33/71	0.31	0.04	412	41	11.2	(0.18, 0.07)	[60]
159	456/—	17/—	94/—	0.06	0.31	466	21	24.2	(0.13, 0.10)	[61]
161a	505/—	20/—	98/—	0.13	0.8	510	29	26.7	(0.17, 0.68)	[62]
161b	553/—	28/—	98/—	0.13	1.9	556	43	21.8	(0.42, 0.57)	[62]
164a	605/610	32/35	96/—	0.25	—	610	39	35.6	(0.64, 0.34)	[63]
164b	609/618	32/37	95/—	0.27	—	618	39	34.4	(0.65, 0.35)	[63]
164c	616/624	33/38	96/—	0.26	—	625	40	36.1	(0.66, 0.33)	[63]
166a	631/—	40/—	80/—	0.20	2.1	613	66	5.8	(0.64, 0.34)	[64]
166b	641/—	39/—	85/—	0.19	2.2	616	65	7.8	(0.65, 0.34)	[64]

Emitter	λ_PL/nm (sol/film)	FWHM_PL/nm (sol/film)	PLQY/% (sol/film)	ΔE_ST/eV		λ_EL/nm	FWHM_EL/nm	EQE/%	CIE	Ref.
167a	470/—	28/—	88/—	0.17	2.53	466	31	31.4	(0.13, 0.15)	[65]
167b	470/—	26/—	97/—	0.14	—	474	27	32.1	(0.12, 0.19)	[66]
168a	449/—	23/—	61/—	0.06	0.70	456	31	14.7	(0.15, 0.08)	[67]
168b	456/—	26/—	77/—	0.08	0.63	456	27	8.0	(0.15, 0.08)	[67]
169a	465/—	22/—	99/—	0.20	0.21	471	22	30.1	(0.12, 0.11)	[68]
169b	454/460	19/26	94/92	0.17	0.12	460	28	21.6	(0.14, 0.09)	[27]
170	470/—	28/—	90/—	0.20	0.15	467	28	20.2	(0.12, 0.13)	[11]
168c	438/—	23/—	74/—	0.10	0.57	460	26	10.2	(0.14, 0.08)	[67]
171a	459/—	21/—	91/—	0.16	0.05	—	—	25.4	(—, 0.165)	[69]
171b	459/—	21/—	89 /—	0.14	0.10	—	—	26.6	(—, 0.165)	[69]
172	462/467	—	97/—	0.12	0.20	468	28	21.3	(0.12, 0.14)	[70]
173	462/—	22/—	98/—	0.18	0.69	462	22	30.1	(0.13, 0.11)	[71]

基于硼氮杂稠环芳烃的多重共振热活化延迟荧光材料研究进展