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

doi:10.6023/cjoc202212037

摘要/Abstract

近年来, 多重共振热活化延迟荧光(multi-resonance thermally activated delayed fluorescence, MR-TADF)材料由于其优异的光物理性质和电致发光器件性能而受到广泛关注. 这类材料通常以稠环芳烃骨架为基础, 通过引入具有相反共振效应的缺电子中心(如硼原子)和富电子中心(如氮原子), 诱导最高占据分子轨道(HOMO)和最低未占分子轨道(LUMO)在分子骨架中分别定域在不同原子上, 从而获得小的单线态-三线态能级差(ΔE_ST), 实现TADF的性质. 与传统的给受体型TADF材料相比, MR-TADF材料具有刚性结构和局域电荷转移特征, 有利于获得高色纯度的窄谱带发光和极高的量子效率, 使其成为理想的发光材料并广泛应用于有机发光二极管(organic light-emitting diode, OLED)中. 自2016年首例基于硼氮杂稠环芳烃的MR-TADF材料被报道以来, 该领域取得了飞速的发展, 但尚缺乏针对材料分子研究进展的系统总结. 综述了基于硼氮杂稠环芳烃的MR-TADF分子的设计策略和合成方法, 从分子骨架的发展、分子骨架的取代基修饰策略以及新型手性MR-TADF材料三个方面, 具体阐述了最新的研究进展, 并展望了未来发展方向, 期望进一步促进MR-TADF分子材料的发展与应用.

关键词: 多重共振, 热活化延迟荧光, 有机发光二极管, 硼氮杂稠环芳烃, 窄谱带发光

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

引用此文

张祎, 杜呈卓, 李继坤, 王小野. 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[J]. 有机化学, 2023, 43(5): 1645-1690.

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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图/表 63

图1. TADF与MR-TADF分子的设计策略与性质特点

Figure 1. Design strategy and the characteristics of TADF and MR-TADF molecules

图2. MR-TADF分子的一般合成策略

Figure 2. General synthetic strategy of MR-TADF molecules

图3. 硼氮杂稠环芳烃类MR-TADF分子骨架概况

Figure 3. Summary of MR-TADF molecular skeletons based on B,N-heteroarenes

图式1. 具有对称结构的MR-TADF分子3和6a~6c的合成

Scheme 1. Synthesis of symmetric MR-TADF molecules 3 and 6a~6c

图式2. 具有对称结构的MR-TADF分子9的合成

Scheme 2. Synthesis of symmetric MR-TADF molecule 9

图式3. 具有对称结构的MR-TADF分子12a~12c的合成

Scheme 3. Synthesis of symmetric MR-TADF molecules 12a~12c

图式4. 具有对称结构的MR-TADF分子14的合成

Scheme 4. Synthesis of symmetric MR-TADF molecule 14

图式5. 具有对称结构的MR-TADF分子17a和17b的合成

Scheme 5. Synthesis of symmetric MR-TADF molecules 17a and 17b

图式6. 具有对称结构的MR-TADF分子19的合成

Scheme 6. Synthesis of symmetric MR-TADF molecule 19

图式7. 具有对称结构的MR-TADF分子21的合成

Scheme 7. Synthesis of symmetric MR-TADF molecule 21

图式8. 具有对称结构的MR-TADF分子24a和24b的合成

Scheme 8. Synthesis of symmetric MR-TADF molecules 24a and 24b

图4. 分子24a和24b的光物理性质及器件性能[23]

Figure 4. Photophysical properties and device performance of 24a and 24b (a) UV-vis absorption (gray line) and fluorescence (red line) spectra at room temperature and phosphorescence (blue line) spectra of 24a and 24b at 77 K. (b) EL spectra of the TADF OLEDs compared with the absorption spectrum of 24a (tCzphB-Ph). (c) CIE (x,y) coordinates of the devices. (d) EQE-L curves of the investigated OLEDs. Inset: diagram of the Fo?rster resonance energy transfer (FRET) and RISC pathways in the PSTADF OLED. Reproduced with permission from Ref. [23]. Copyright 2022 Springer.

图式9. 具有对称结构的MR-TADF分子27的合成

Scheme 9. Synthesis of symmetric MR-TADF molecule 27

图式10. 具有非对称结构的MR-TADF分子30的合成

Scheme 10. Synthesis of unsymmetric MR-TADF molecule 30

图式11. 具有非对称结构的MR-TADF分子33a和33b的合成

Scheme 11. Synthesis of unsymmetric MR-TADF molecules 33a and 33b

图式12. 具有非对称结构的MR-TADF分子37的合成

Scheme 12. Synthesis of unsymmetric MR-TADF molecule 37

图式13. 外围共轭延伸的MR-TADF分子40的合成

Scheme 13. Synthesis of MR-TADF molecule 40 with peripheral π-extension

图式14. 外围共轭延伸的MR-TADF分子42的合成

Scheme 14. Synthesis of MR-TADF molecule 42 with peripheral π-extension

图式15. 外围共轭延伸的MR-TADF分子45和47的合成

Scheme 15. Synthesis of MR-TADF molecules 45 and 47 with peripheral π-extension

图式16. 外围共轭延伸的MR-TADF分子49和50的合成

Scheme 16. Synthesis of MR-TADF molecules 49 and 50 with peripheral π-extension

图5. 分子49、50和53的光物理性质及器件性能[30-31]

Figure 5. Photophysical properties and device performance of 49, 50 and 53 (a) UV-vis absorption, fluorescence (298 K), and phosphorescence (77 K) spectra of 49 and 50. (b) PL spectra of 42, 49 and 50. (c) EQE-L curves of 49 and 50. Inset: EL spectra. Reproduced with permission from Ref. [30]. Copyright 2022 Wiley-VCH. (d) UV-vis absorption, measured and calculated fluorescence (298 K) spectra of 53. (e) EL spectra of 53 at 1000 cd?m-2. (f) EQE-L curves (green), CE-L curves (blue) and PE-L curves (sky blue) of 53. Reproduced with permission from Ref. [31]. Copyright 2022 Springer.

图式17. 外围共轭延伸的MR-TADF分子53的合成

Scheme 17. Synthesis of MR-TADF molecule 53 with peripheral π-extension

图式18. 核心共轭拓展的MR-TADF分子56的合成

Scheme 18. Synthesis of MR-TADF molecule 56 with π-exten- sion on the central core

图式19. 核心共轭拓展的MR-TADF分子59和62的合成

Scheme 19. Synthesis of MR-TADF molecules 56 and 62 with π-extension on the central core

图式20. 核心共轭拓展的MR-TADF分子65的合成

Scheme 20. Synthesis of MR-TADF molecule 65 with π-extension on the central core

图式21. 核心共轭拓展的MR-TADF分子68a和68b的合成

Scheme 21. Synthesis of MR-TADF molecules 68a and 68b with π-extension on the central core

图式22. 一步直接硼化法合成MR-TADF分子70~72

Scheme 22. Synthesis of MR-TADF molecules 70~72 via the one-shot borylation method

图式23. 一步直接硼化法合成MR-TADF分子74和76a~76c

Scheme 23. Synthesis of MR-TADF molecules 74 and 76a~76c via the one-shot borylation method

图6. 分子74、76b和76c的器件性能[37,39]

Figure 6. Device performance of 74, 76b and 76c (a) EL spectrum and 74. (b) EQE-L curves of 74. Reproduced with permission from Ref. [37]. Copyright 2019 Springer. (c) EL spectra and 76a and 76b. (d) EQE-L curves of 76a and 76b. (e) CIE (x, y) coordinates of 76a and 76b. Reproduced with permission from Ref. [39]. Copyright 2022 Wiley-VCH.

图式24. 一步直接硼化法合成MR-TADF分子78~80

Scheme 24. Synthesis of MR-TADF molecules 78~80 via the one-shot borylation method

图式25. 一步直接硼化法合成MR-TADF分子81

Scheme 25. Synthesis of MR-TADF molecules 81 via the one-shot borylation method

图式26. B/N/B型MR-TADF分子的合成

Scheme 26. Synthesis of B/N/B-type MR-TADF molecules

图式27. B/N二元掺杂型MR-TADF分子91、94、97和100的合成

Scheme 27. Synthesis of binary-B/N-doped MR-TADF molecules 91, 94, 97 and 100

图式28. B/N二元掺杂型MR-TADF分子103和105的合成

Scheme 28. Synthesis of binary-B/N-doped MR-TADF molecules 103 and 105

图式29. 含有B—N共价键或配位键的MR-TADF分子的合成

Scheme 29. Synthesis of MR-TADF molecules with B—N covalent bond or coordination bond

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]

表1. 硼氮杂稠环芳烃类MR-TADF分子骨架的光物理性质和器件性能

Table 1. Photophysical properties and device performance of MR-TADF molecules based on B,N-heteroarenes

表1. 硼氮杂稠环芳烃类MR-TADF分子骨架的光物理性质和器件性能

Table 1. Photophysical properties and device performance of MR-TADF molecules based on B,N-heteroarenes

图7. 含其他杂原子的硼氮杂稠环芳烃类MR-TADF分子骨架概览

Figure 7. Chemical structures of MR-TADF molecules based on B,N-heteroarenes with other heteroatoms

图式30. 杂原子掺杂的DABNA类MR-TADF分子119和121的合成

Scheme 30. Synthesis of DABNA-type MR-TADF molecules 119 and 121 with other heteroatoms

图式31. 杂原子掺杂的DABNA类MR-TADF分子123a和123b的合成

Scheme 31. Synthesis of DABNA-type MR-TADF molecules 123a and 123b with other heteroatoms

图式32. 杂原子掺杂的DABNA类MR-TADF分子126a和126b的合成

Scheme 32. Synthesis of DABNA-type MR-TADF molecules 126a and 126b with other heteroatoms

图式33. 杂原子掺杂的DABNA类MR-TADF分子128a~128c的合成

Scheme 33. Synthesis of DABNA-type MR-TADF molecules 128a~128c with other heteroatoms

图式34. 杂原子掺杂的DABNA类MR-TADF分子131a和131b的合成

Scheme 34. Synthesis of DABNA-type MR-TADF molecules 131a and 131b with other heteroatoms

图式35. 杂原子掺杂的DABNA类MR-TADF分子133、136a和136b的合成

Scheme 35. Synthesis of DABNA-type MR-TADF molecules 133, 136a and 136b with other heteroatoms

图式36. 杂原子掺杂的ν-DABNA类MR-TADF分子139、142、145和148的合成

Scheme 36. Synthesis of ν-DABNA-type MR-TADF molecules 139, 142, 145 and 148 with other heteroatoms

图式37. 杂原子掺杂的ν-DABNA类MR-TADF分子151的合成

Scheme 37. Synthesis of ν-DABNA-type MR-TADF molecule 151 with other heteroatoms

图式38. 杂原子掺杂的ν-DABNA类MR-TADF分子154的合成

Scheme 38. Synthesis of ν-DABNA-type MR-TADF molecule 154 with other heteroatoms

图式39. 杂原子掺杂的ν-DABNA类MR-TADF分子157的合成

Scheme 39. Synthesis of ν-DABNA-type MR-TADF molecule 157 with other heteroatoms

图式40. 其他类型的杂原子掺杂的MR-TADF分子159、161a和161b的合成

Scheme 40. Synthesis of other types of MR-TADF molecules 159, 161a and 161b with other heteroatoms

图式41. 其他类型的杂原子掺杂的MR-TADF分子164a~164c的合成

Scheme 41. Synthesis of other types of MR-TADF molecules 164a~164c with other heteroatoms

图8. 分子164a~164c的光物理性质及器件性能[63]

Figure 8. Photophysical properties and device performance of 164a~164c (a) Fluorescence spectra of 164a~164c. (b) EL spectra of 164a~164c. (c) EQE-L curves of 164a~164c. (d) CIE (x, y) coordinates of 164a~164c. Reproduced with permission from Ref. [63]. Copyright 2022 Wiley-VCH.

图式42. 其他类型的杂原子掺杂的MR-TADF分子166a和166b的合成

Scheme 42. Synthesis of other types of MR-TADF molecules 166a and 166b with other heteroatoms

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]

表2. 含其他杂原子的硼氮杂稠环芳烃类MR-TADF分子骨架的光物理性质和器件性能

Table 2. Photophysical properties and device performance of MR-TADF molecules based on B,N-heteroarenes with other heteroatoms

表2. 含其他杂原子的硼氮杂稠环芳烃类MR-TADF分子骨架的光物理性质和器件性能

Table 2. Photophysical properties and device performance of MR-TADF molecules based on B,N-heteroarenes with other heteroatoms

图9. 基于DABNA骨架取代基修饰的MR-TADF分子

Figure 9. MR-TADF molecules based on the modifications of the DABNA skeleton

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]

表3. 基于DABNA骨架修饰的MR-TADF分子的光物理性质和器件性能

Table 3. Photophysical properties and device performance of MR-TADF molecules based on the DABNA skeleton

图10. 基于ν-DABNA骨架取代基修饰的MR-TADF分子

Figure 10. Chemical structures of MR-TADF molecules based on the modifications of the ν-DABNA skeleton

Emitter	λ_PL/nm (sol)	FWHM_PL/nm	PLQY/%	ΔE_ST/eV		λ_EL/nm	FWHM_EL/nm	EQE/%	CIE	Ref.
74	469	18	82	0.017	2.01	469	18	34.4	(0.12, 0.11)	[37]
174a	464	14	91	0.07	2.30	471	18	36.2	(0.12, 0.12)	[72]
174b	457	14	90	0,05	2.28	464	18	26.8	(0.13, 0.08)	[72]
174c	455	14	89	0.07	2.10	461	18	24.9	(0.13, 0.06)	[72]
175	496	17	86	0.1	1.05	504	23	31.6	(0.13, 0.65)	[73]

表4. 基于ν-DABNA骨架的MR-TADF分子的光物理性质和器件性能

Table 4. Photophysical properties and device performance of MR-TADF molecules based on the ν-DABNA skeleton

图11. 基于DtBuCzB骨架修饰的MR-TADF分子

Figure 11. MR-TADF molecules based on the modifications of the DtBuCzB skeleton

Emitter	λ_PL/nm	FWHM_PL/nm	PLQY/%	ΔE_ST/eV	k_RISC/(10⁵ s^–1)	λ_EL/nm	FWHM_EL/nm	EQE/%	CIE	Ref.
Emitter	(sol/film)	(sol/film)	(sol/film)	ΔE_ST/eV	k_RISC/(10⁵ s^–1)	λ_EL/nm	FWHM_EL/nm	EQE/%	CIE	Ref.
6b	481/—	22/—	91/—	0.13	0.15	488	29	21.6	(0.01, 0.42)	[15]
176	496/—	21/—	97/—	0.09	—	512	33	25.5	(0.20, 0.65)	[15]
177a	562/563	30/44	98/86	0.09	1.4	568	43	24.7	(0.47, 0.52)	[75]
177b	572/576	34/44	87/87	0.14	0.18	571	44	19.6	(0.47, 0.51)	[19]
178	512/517	27/31	100/89	0.09	0.2	515	30	29.2	(0.16, 0.71)	[19]
179	534/538	30/41	98/89	0.13	1.5	545	46	24.5	(0.38, 0.61)	[75]
180	496/499	23/38	99/93	0.11	1.9	506	36	24.3	(0.15, 0.63)	[75]
181	567/—	34/—	95/—	0.12	—	—	—	—	—	[76]
182	624/—	46/—	94/—	0.11	0.11	618	47	20.1	(0.64, 0.34)	[76]
183	549/—	42/—	85/—	0.14	1	549	48	29.3	(0.39, 0.59)	[16]
184	581/—	42/—	96/—	0.18	4.2	583	49	33.7	(0.54, 0.46)	[82]
185	517/—	34/—	90/—	0.14	1.8	515	54	31.8	(0.26, 0.68)	[16]
186	514/—	34/—	93/—	0.13	21.3	513	37	32.5	(0.17, 0.68)	[83]
187	513/—	29/—	95/—	0.11	15.5	513	33	31.4	(0.16, 0.70)	[83]
189	494/—	24/—	89/—	0.16	0.22	501	40	22	(0.16, 0.60)	[74]
190	499/—	24/—	83/—	0.08	0.39	499	39	22.7	(0.20, 0.58)	[74]
191	496/—	25/—	91/—	0.11	0.44	493	32	20.9	(0.12, 0.48)	[74]
192	486/485	20/25	86/92	0.12	0.08	488	26	27.8	(0.14, 036)	[84]
193	477/—	19/—	96/—	0.13	0.09	484	25	29	(0.10, 0.29)	[86]
194	485/494	26/—	80/—	0.14	0.29	491	26	19	(0.11, 0.43)	[89]
195	485/494	26/—	78/—	0.15	0.3	493	29	25.6	(0.10, 0.47)	[89]
196	486/500	24/—	71/—	0.14	0.81	492	28	24.1	(0.10, 0.46)	[89]
197	515/—	36/—	93/—	0.15	0.01	540	44	28.1	(0.35, 0.63)	[78]
198	499/—	25/—	96/—	0.11	0.1	508	33	28.6	(0.16, 0.66)	[78]
199	470/—	21/—	86/—	0.11	0.25	480	27	30.2	(0.11, 0.24)	[86]
200	491/496	21/30	90/95	0.15	0.06	496	30	27.2	(0.13, 0.54)	[84]
201	490/—	23/—	94/—	0.15	0.18	488	26	30.5	(0.12, 0.43)	[80]
202	495/494	21/29	85/88	0.14	0.16	496	31	25.9	(0.15, 0.55)	[84]
203	490/—	23/—	93/—	0.12	0.16	496	25	40	(0.09, 0.50)	[81]
204	490/—	23/—	91/—	0.13	0.14	497	26	36.4	(0.10, 0.53)	[81]
205	492/495	21/28	91/94	0.09	0.14	492	28	28.9	(0.01, 0.46)	[84]
206	489/—	23/—	96/—	0.14	0.16	492	28	26	(0.09, 0.46)	[90]
207	521/—	24/—	94/—	0.18	0.01	532	39	24.6	(0.33, 0.63)	[78]
208	501/—	27/—	97/—	0.11	0.11	516	38	29.8	(0.18, 0.67)	[78]
209	491/—	24/—	96/—	0.13	0.35	498	31	26.4	(0.10, 0.56)	[90]
210	493/—	23/—	90/—	0.13	0.91	492	28	35.9	(0.08, 0.48)	[85]
211	493/—	25/—	86/—	0.15	0.33	496	30	32.2	(0.09, 0.52)	[85]
212	487/—	22/—	92/—	0.11	4.6	496	34	27.3	(0.12, 0.54)	[87]
213	489/—	22/—	90/—	0.12	2.3	496	31	24.6	(0.11, 0.53)	[87]
214	505/513	34/41	85/80	0.17	0.04	511	41	20.2	(0.16, 0.66)	[88]
215	519/—	38/—	97/—	0.08	10	520	44	27	(0.23, 0.69)	[77]
216	488/496	25/32	93/95	0.16	0.09	492	28	35	(0.09, 0.48)	[79]
217	491/498	25/32	96/98	0.16	0.12	496	28	41.1	(0.09, 0.53)	[79]
218	494/500	25/33	97/98	0.15	0.13	504	29	36.8	(0.11, 0.61)	[79]
219	491/498	26/34	97/97	0.14	0.12	496	28	42	(0.09, 0.54)	[79]
220	515/517	35/40	90/85	0.13	1.2	515	39	23.5	(0.20, 0.70)	[88]

Emitter	λ_PL/nm	FWHM_PL/nm	PLQY/%	ΔE_ST/eV	k_RISC/(10⁵ s^–1)	λ_EL/nm	FWHM_EL/nm	EQE/%	CIE	Ref.
Emitter	(sol/film)	(sol/film)	(sol/film)	ΔE_ST/eV	k_RISC/(10⁵ s^–1)	λ_EL/nm	FWHM_EL/nm	EQE/%	CIE	Ref.
6b	481/—	22/—	91/—	0.13	0.15	488	29	21.6	(0.01, 0.42)	[15]
176	496/—	21/—	97/—	0.09	—	512	33	25.5	(0.20, 0.65)	[15]
177a	562/563	30/44	98/86	0.09	1.4	568	43	24.7	(0.47, 0.52)	[75]
177b	572/576	34/44	87/87	0.14	0.18	571	44	19.6	(0.47, 0.51)	[19]
178	512/517	27/31	100/89	0.09	0.2	515	30	29.2	(0.16, 0.71)	[19]
179	534/538	30/41	98/89	0.13	1.5	545	46	24.5	(0.38, 0.61)	[75]
180	496/499	23/38	99/93	0.11	1.9	506	36	24.3	(0.15, 0.63)	[75]
181	567/—	34/—	95/—	0.12	—	—	—	—	—	[76]
182	624/—	46/—	94/—	0.11	0.11	618	47	20.1	(0.64, 0.34)	[76]
183	549/—	42/—	85/—	0.14	1	549	48	29.3	(0.39, 0.59)	[16]
184	581/—	42/—	96/—	0.18	4.2	583	49	33.7	(0.54, 0.46)	[82]
185	517/—	34/—	90/—	0.14	1.8	515	54	31.8	(0.26, 0.68)	[16]
186	514/—	34/—	93/—	0.13	21.3	513	37	32.5	(0.17, 0.68)	[83]
187	513/—	29/—	95/—	0.11	15.5	513	33	31.4	(0.16, 0.70)	[83]
189	494/—	24/—	89/—	0.16	0.22	501	40	22	(0.16, 0.60)	[74]
190	499/—	24/—	83/—	0.08	0.39	499	39	22.7	(0.20, 0.58)	[74]
191	496/—	25/—	91/—	0.11	0.44	493	32	20.9	(0.12, 0.48)	[74]
192	486/485	20/25	86/92	0.12	0.08	488	26	27.8	(0.14, 036)	[84]
193	477/—	19/—	96/—	0.13	0.09	484	25	29	(0.10, 0.29)	[86]
194	485/494	26/—	80/—	0.14	0.29	491	26	19	(0.11, 0.43)	[89]
195	485/494	26/—	78/—	0.15	0.3	493	29	25.6	(0.10, 0.47)	[89]
196	486/500	24/—	71/—	0.14	0.81	492	28	24.1	(0.10, 0.46)	[89]
197	515/—	36/—	93/—	0.15	0.01	540	44	28.1	(0.35, 0.63)	[78]
198	499/—	25/—	96/—	0.11	0.1	508	33	28.6	(0.16, 0.66)	[78]
199	470/—	21/—	86/—	0.11	0.25	480	27	30.2	(0.11, 0.24)	[86]
200	491/496	21/30	90/95	0.15	0.06	496	30	27.2	(0.13, 0.54)	[84]
201	490/—	23/—	94/—	0.15	0.18	488	26	30.5	(0.12, 0.43)	[80]
202	495/494	21/29	85/88	0.14	0.16	496	31	25.9	(0.15, 0.55)	[84]
203	490/—	23/—	93/—	0.12	0.16	496	25	40	(0.09, 0.50)	[81]
204	490/—	23/—	91/—	0.13	0.14	497	26	36.4	(0.10, 0.53)	[81]
205	492/495	21/28	91/94	0.09	0.14	492	28	28.9	(0.01, 0.46)	[84]
206	489/—	23/—	96/—	0.14	0.16	492	28	26	(0.09, 0.46)	[90]
207	521/—	24/—	94/—	0.18	0.01	532	39	24.6	(0.33, 0.63)	[78]
208	501/—	27/—	97/—	0.11	0.11	516	38	29.8	(0.18, 0.67)	[78]
209	491/—	24/—	96/—	0.13	0.35	498	31	26.4	(0.10, 0.56)	[90]
210	493/—	23/—	90/—	0.13	0.91	492	28	35.9	(0.08, 0.48)	[85]
211	493/—	25/—	86/—	0.15	0.33	496	30	32.2	(0.09, 0.52)	[85]
212	487/—	22/—	92/—	0.11	4.6	496	34	27.3	(0.12, 0.54)	[87]
213	489/—	22/—	90/—	0.12	2.3	496	31	24.6	(0.11, 0.53)	[87]
214	505/513	34/41	85/80	0.17	0.04	511	41	20.2	(0.16, 0.66)	[88]
215	519/—	38/—	97/—	0.08	10	520	44	27	(0.23, 0.69)	[77]
216	488/496	25/32	93/95	0.16	0.09	492	28	35	(0.09, 0.48)	[79]
217	491/498	25/32	96/98	0.16	0.12	496	28	41.1	(0.09, 0.53)	[79]
218	494/500	25/33	97/98	0.15	0.13	504	29	36.8	(0.11, 0.61)	[79]
219	491/498	26/34	97/97	0.14	0.12	496	28	42	(0.09, 0.54)	[79]
220	515/517	35/40	90/85	0.13	1.2	515	39	23.5	(0.20, 0.70)	[88]

表5. 基于DtBuCzB骨架修饰的MR-TADF分子的光物理性质和器件性能

Table 5. Photophysical properties and device performance of MR-TADF molecules based on the modifications of the DtBuCzB skeleton

表5. 基于DtBuCzB骨架修饰的MR-TADF分子的光物理性质和器件性能

Table 5. Photophysical properties and device performance of MR-TADF molecules based on the modifications of the DtBuCzB skeleton

图12. 轴手性MR-TADF分子及其器件性能[91]

Figure 12. Axial chiral MR-TADF molecules and their device performances (a, d, g) Chemical structures of chiral MR-TADF molecules. (b, e) EQE-L curves of 221a and 221b. (c, f) CPEL spectra of (R/S)-221a and (R/S)-221b. Reproduced with permission from Ref. [91a]. Copyright 2021 Wiley-VCH. (h) CE-L and EQE-L curves of 223a and 223b. (i) CPEL spectra of (R/S)-223a and (R/S)-223b. Reproduced with permission from Ref. [91b]. Copyright 2022 Wiley-VCH.

图13. 螺旋手性MR-TADF分子及其器件性能[17-18,93]

Figure 13. Helical chiral MR-TADF molecules and their device performance (a, f, i) Chemical structures of chiral MR-TADF molecules. (b, c) EQE-current density curves of (+)/(–)-224a and (+)/(–)-224b. (d, e) CPEL spectra of (+)/(–)-224a and (+)/(–)-224b. Reproduced with permission from Ref. [93a]. Copyright 2022 Wiley-VCH. (g) EQE-current density curves of 12a and 12b. Reproduced with permission from Ref. [17]. Copyright 2021 Wiley-VCH. (h) CPL spectra of 12a-(P,P) and 12a-(M,M). Reproduced with permission from Ref. [18]. Copyright 2021 American Chemical Society. (j) EQE-L curves of (P/M)-225. (k) CPEL spectra of (P/M)-225. Reproduced with permission from Ref. [93b]. Copyright 2022 CCS Chemistry.

图14. 中心手性MR-TADF分子及其器件性能[94]

Figure 14. Central chiral MR-TADF molecules and its device performance (a) Chemical structures of chiral MR-TADF molecule 226. (b) EQE-L curves of (R/S)-226. (c) CE-L-PE of (R/S)-226. (d) CPEL spectra of (R/S)-226. Reproduced with permission from Ref. [94]. Copyright 2022 Wiley-VCH.

图15. 面手性MR-TADF分子及其器件性能[95]

Figure 15. Planar chiral MR-TADF molecules and their device performances (a, d) Chemical structures of chiral MR-TADF molecules 227 and 228. (b) EL spectra of (R/S)-227 and (R/S)-228. (c) EQE-L curves of (R/S)-227 and (R/S)-228. (e, f) CPEL spectra of (R/S)-227 and (R/S)-228. Reproduced with permission from Ref. [95]. Copyright 2022 Wiley-VCH.

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	g_EL(10^–3)	Ref.
221	493/—	22/—	99/—	0.12	0.10	496	33	29.8	(0.13, 0.53)	+1.43/–1.27	[91a]
222	500/—	27/—	96/—	0.13	0.08	508	34	24.7	(0.16, 0.66)	+4.60/–4.76	[91a]
223a	453/—	21/—	83/—	0.14	0.16	459	38	23.9	(0.14, 0.10)	+0.9/–0.9	[91b]
223b	459/—	21/—	89/—	0.12	0.08	464	35	25.6	(0.13, 0.12)	+0.9/–1.0	[91b]
224a	500/522	43/50	88/96	0.14	1.60	510	49	20.6	(0.19, 0.63)	+3.7/–3.1	[93a]
224b	497/512	44/49	87/92	0.14	0.74	506	48	26.5	(0.17, 0.60)	+1.9/–1.6	[93a]
225	520/—	46/—	98/—	0.18	0.46	523	49	31.5	(0.26, 0.66)	+1.2/–2.2	[93b]
226	497/—	30/—	96/—	0.11	0.63	504	33	37.2	(0.12, 0.63)	+0.27/–0.29	[94]
227	478/—	23/—	98/—	0.09	0.58	479	24	32.1	(0.10, 0.19)	+1.54/–1.48	[95]
228	498/—	36/—	93/—	0.13	0.15	513	48	28.7	(0.11, 0.54)	+1.30/–1.25	[95]

表6. 硼氮杂稠环芳烃类手性MR-TADF分子的光物理性质和器件性能总结

Table 6. Photophysical properties and device performance of chiral MR-TADF emitters based on B,N-heteroarenes

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