有机化学 ›› 2023, Vol. 43 ›› Issue (4): 1292-1309.DOI: 10.6023/cjoc202208023 上一篇 下一篇
综述与进展
杨晓东a, 郑小康a, 董海亮a, 孙静a,b,*(), 王华
收稿日期:
2022-08-19
修回日期:
2022-11-02
发布日期:
2022-12-21
通讯作者:
孙静
基金资助:
Xiaodong Yanga, Xiaokang Zhenga, Hailiang Donga, Jing Suna,b(), Hua Wang
Received:
2022-08-19
Revised:
2022-11-02
Published:
2022-12-21
Contact:
Jing Sun
Supported by:
文章分享
圆偏振热活化延迟荧光材料具有分子结构易修饰、激子利用率高及圆偏振发光等特点, 在光学信息存储、3D显示、发光器件和数据加密等领域具有广阔应用前景. 利用此类材料作为发光层制备的圆偏振有机发光二极管, 能够同时实现高发光不对称因子和理论上达100%的激子利用率, 对发展低功耗和高性能有机发光二极管至关重要. 近年来, 通过不断的分子结构设计与优化, 该类材料在有机发光二极管中的电致发光效率不断提高, 但是仍然存在不对称因子低及效率滚降严重等问题. 基于此, 整理了目前已报道的圆偏振热活化延迟荧光化合物, 重点讨论了其分子结构设计与光物理性质、圆偏振特性以及电致发光性能的关系规律, 并对高性能圆偏振热活化延迟荧光材料的制备及其在有机发光二极管中的应用进行了展望.
杨晓东, 郑小康, 董海亮, 孙静, 王华. 圆偏振热活化延迟荧光材料及其器件的研究进展[J]. 有机化学, 2023, 43(4): 1292-1309.
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.
Compound | λPL/nm | Host/[ω(emitter)/%] | ΔEST/eV | τd/μs | PLQY/% | |glum|/10-3 | λEL/nm | EQE/% | |gEL|/10-3 | Ref. |
---|---|---|---|---|---|---|---|---|---|---|
1 | 519a | mCP (9) | 0.14b | – | 26%a | 1.1b | – | – | – | [ |
2 | 533c | mCBP (15) | 0.06a | 130a | 98a | 1.1a | 520 | 19.8 | 2.3 | [ |
3 | 597b | CBP (6) | 0.07a | 37.4a | 39.9a | 0.92a | 592 | 12.4 | – | [ |
4 | 512b | mCBP (30) | 0.052b | 6.78a | 53.1a | 2.2b | 508 | 12.5 | 1.3 | [ |
5 | 512b | mCBP (30) | 0.053b | 7.98a | 89.0a | 3.4b | 508 | 23.1 | 1.0 | [ |
6 | 470b | DPEPO (25) | 0.022b | 4.7a | 81.2a | 3.0b | 472 | 20.0 | 3.1 | [ |
7 | 473a | mCPCN (12) | 0.19a | 2.3b | 89a | 0.59b | 494 | 20.3 | 0.74 | [ |
8 | 565a | mCPCN (6) | 0.22a | 9.7b | 86a | 2.0b | 591 | 23.7 | 2.4 | [ |
9 | 451a | DPEPO (12) | 0.05a | 3.4a | 86a | 0.3b | 458 | 18.5 | – | [ |
10 | 541c | – | 0.03c | 1.1c | 85c | 1.9c | 534 | 25.5 | 1.5 | [ |
11 | 497b | DMIC-TRZ (1) | 0.01b | 28.1a | 96a | 0.25b | 504 | 37.2 | 0.27 | [ |
12 | 517b | mCP (20) | – | 2.9b | 53b | 1.3b | 540 | 9.1 | – | [ |
13 | 493a | mCP (10) | 0.15b | 24.3a | 32a | 1.2b | 496 | 9.3 | 60 | [ |
14 | 571a | mCP (10) | 0.11b | 1.07a | 38a | 0.5b | 571 | 1.7 | 91 | [ |
15 | 534a | mCP (10) | 0.11b | 2.51a | 12.5a | 1.1b | 527 | 6.3 | 63 | [ |
16 | 540a | mCP (10) | 0.02b | 1.77a | 45a | 0.7b | 547 | 3.5 | 82 | [ |
17 | 516a | mCP (10) | 0.08g | 15a | 20a | 0.37c | 496 | 10.1 | 3.7 | [ |
18 | 529a | mCP (10) | 0.03g | 8a | 55a | 0.58c | 516 | 10.6 | 3.9 | [ |
19 | 568a | TCTA (15) | 0.059b | 1.03a | 18.5a | 1.6b | 580 | 1.8 | 1.0 | [ |
20 | 600a | mCP (10) | 0.14b | 5.5a | 15.8a | 2.2b | 600 | 2.0 | 2.1 | [ |
21 | 469b | – | 0.054f | 10a | 7a | 2.1b | – | – | – | [ |
22 | 490b | – | 0.051f | 45a | 16a | 1.6b | – | – | – | [ |
23 | 506b | – | 0.017f | 39a | 18a | 0.2b | – | – | – | [ |
24 | 516b | – | 0.022f | 16a | 30a | <0.1b | – | – | – | [ |
25 | 481b | – | 0.013f | 6a | 29a | 1.1b | – | – | – | [ |
26 | 504b | – | 0.053f | 19a | 46a | 1.0b | – | – | – | [ |
27 | 510b | mCP | 0.009f | 17a | 42a | 1.1b | 510 | 0.8 | 1.0 | [ |
28 | 493b | – | 0.136f | 18a | 25a | <0.1b | – | – | – | [ |
29 | 511b | – | 0.07f | 40a | 31a | <0.1b | – | – | – | [ |
30 | 519b | – | 0.075f | 22a | 47a | 0.7b | – | – | – | [ |
31 | 612b | – | – | 0.46h | 5.3h | 0.31h | – | – | – | [ |
32 | 670c | – | 0.28b | 0.9b | 1c | 0.25d | 716 | 1.9 | – | [ |
33 | 662c | – | 0.23b | 1.2b | 2c | 0.15d | 700 | 0.7 | – | [ |
34 | 537a | TCTA (8) | 0.18b | 170a | 86a | 0.3b | 530 | 27.6 | – | [ |
35 | 503a | 2,6-DCzPPy (8) | 0.12b | 75a | 77a | 5.3b | 506 | 20.5 | – | [ |
36 | 503b | 2,6-DCzPPy (10) | 0.037b | 7.7a | 92a | 0.56b | 501 | 32.6 | 2.34 | [ |
37 | 538b | 2,6-DCzPPy (10) | 0.09b | 13.5a | 85a | 1.88b | 544 | 12.3 | 2.3 | [ |
38 | 504b | mCP (15) | 0.04b | 3.2a | 73a | 0.7b | 502 | 15.0 | 0.8 | [ |
39 | 520b | mCP (15) | 0.05b | 2.7a | 87a | 0.39b | 514 | 20.3 | 0.5 | [ |
40 | 589b | CBP (15) | 0.16b | 3.6a | 92a | 1.9b | 548 | 28.3 | 0.6 | [ |
41 | 630b | CBP (7) | 0.07b | 3.7a | 89a | 0.4b | 600 | 20.3 | 2.4 | [ |
42 | 509a | mCBP (13) | 0.08c | 4.0a | 81a | 2.6b | 514 | 19.0 | 0.47 | [ |
43 | 493b | PhCzBCz (3) | 0.12b | 95.3a | 99b | 0.91a | 496 | 29.4 | 1.4 | [ |
44 | 500b | PhCzBCz (3) | 0.13b | 97.4a | 96b | 1.04a | 508 | 24.5 | 0.46 | [ |
45 | 505c | CBP (25) | 0.067c | 12.9a | 79.7c | 2.2b | 522 | 17.1 | 1.5 | [ |
46 | 458b | DPEPO (20) | 0.029a | 12.6a | 68.2a | 4.8a | 468 | 12.7 | 14 | [ |
47 | 497b | DPEPO (25) | 0.05a | 4.0a | 74a | 5.4b | 500 | 20.8 | – | [ |
48 | 543b | 2,6-DCzPPy (8) | 0.04b | 1.1b | 86.1b | 9.7b | 537 | 17.8 | – | [ |
49 | 485a | DPEPO (25) | 0.09b | 6.4a | 64a | 7.09b | 483 | 16.7 | 5.5 | [ |
50 | 482a | DPEPO (25) | 0.05b | 7.0a | 76a | 5.05b | 480 | 18.3 | 3.8 | [ |
51 | 529b | mCP (1) | 0.00f | 0.78a | 11b | 0.7 | – | – | – | [ |
52 | 530b | mCP (1) | 0.00f | 0.95a | 29b | 2.0 | – | – | – | [ |
53 | 492b | mCP (1) | 0.22f | 0.57a | 23b | 0.8 | – | – | – | [ |
54 | 482a | DPEPO (10) | 0.16a | 65a | 70a | 1.3b | 480 | 17.0 | – | [ |
55 | 527a | CBP (10) | 0.03b | 12.1a | 60a | 2.3b | 560 | 7.8 | 4.3 | [ |
56 | 565b | CBP (10) | 0.19f | 75a | 78a | 1.9b | 557 | 20.1 | 1.5 | [ |
57 | 522a | mCPCN (3) | 0.14b | 8.3b | 96a | 1.5b | 510 | 20.6 | 3.7 | [ |
58 | 512a | mCPCN (1) | 0.14b | 23.1b | 92a | 1.5b | 506 | 26.5 | 1.9 | [ |
59 | 660b | – | 0.22b | 16.4b | 100b | 2.0e | – | – | – | [ |
60 | 684b | – | 0.21b | 43.9b | 99b | 2.0e | – | – | – | [ |
61 | 696b | – | 0.18b | 26.8b | 90b | 1.5e | – | – | – | [ |
62 | 461b | mCBP (5) | 0.11b | 40.3a | 46.6a | 1.1b | 467 | 14.0 | 1.5 | [ |
63 | 446b | DPEPO (18) | 0.23b | 536a | 51.0a | 1.2e | 488 | 10.6 | 1.6 | [ |
64 | 473b | mCP (1) | 0.15a | 4.37a | 4.1a | 0.4b | – | – | – | [ |
65 | 539c | CBP (5) | – | 1.35c | 6.7c | 2.01c | 529 | 0.37 | – | [ |
66 | 542c | CBP (5) | – | 1.37c | 10.3c | 1.39c | 528 | 0.87 | – | [ |
67 | 487a | mCP (15) | 0.03a | 1.07a | 63a | 1.4a | 496 | 12.0 | 1.1 | [ |
68 | 532a | mCP (10) | 0.01a | 1.75a | 92a | 1.0a | 534 | 22.1 | 1.0 | [ |
69 | 547b | mCP (10) | 0.061f | 2.3a | 76a | 1.9a | 544 | 15.8 | 1.6 | [ |
Compound | λPL/nm | Host/[ω(emitter)/%] | ΔEST/eV | τd/μs | PLQY/% | |glum|/10-3 | λEL/nm | EQE/% | |gEL|/10-3 | Ref. |
---|---|---|---|---|---|---|---|---|---|---|
1 | 519a | mCP (9) | 0.14b | – | 26%a | 1.1b | – | – | – | [ |
2 | 533c | mCBP (15) | 0.06a | 130a | 98a | 1.1a | 520 | 19.8 | 2.3 | [ |
3 | 597b | CBP (6) | 0.07a | 37.4a | 39.9a | 0.92a | 592 | 12.4 | – | [ |
4 | 512b | mCBP (30) | 0.052b | 6.78a | 53.1a | 2.2b | 508 | 12.5 | 1.3 | [ |
5 | 512b | mCBP (30) | 0.053b | 7.98a | 89.0a | 3.4b | 508 | 23.1 | 1.0 | [ |
6 | 470b | DPEPO (25) | 0.022b | 4.7a | 81.2a | 3.0b | 472 | 20.0 | 3.1 | [ |
7 | 473a | mCPCN (12) | 0.19a | 2.3b | 89a | 0.59b | 494 | 20.3 | 0.74 | [ |
8 | 565a | mCPCN (6) | 0.22a | 9.7b | 86a | 2.0b | 591 | 23.7 | 2.4 | [ |
9 | 451a | DPEPO (12) | 0.05a | 3.4a | 86a | 0.3b | 458 | 18.5 | – | [ |
10 | 541c | – | 0.03c | 1.1c | 85c | 1.9c | 534 | 25.5 | 1.5 | [ |
11 | 497b | DMIC-TRZ (1) | 0.01b | 28.1a | 96a | 0.25b | 504 | 37.2 | 0.27 | [ |
12 | 517b | mCP (20) | – | 2.9b | 53b | 1.3b | 540 | 9.1 | – | [ |
13 | 493a | mCP (10) | 0.15b | 24.3a | 32a | 1.2b | 496 | 9.3 | 60 | [ |
14 | 571a | mCP (10) | 0.11b | 1.07a | 38a | 0.5b | 571 | 1.7 | 91 | [ |
15 | 534a | mCP (10) | 0.11b | 2.51a | 12.5a | 1.1b | 527 | 6.3 | 63 | [ |
16 | 540a | mCP (10) | 0.02b | 1.77a | 45a | 0.7b | 547 | 3.5 | 82 | [ |
17 | 516a | mCP (10) | 0.08g | 15a | 20a | 0.37c | 496 | 10.1 | 3.7 | [ |
18 | 529a | mCP (10) | 0.03g | 8a | 55a | 0.58c | 516 | 10.6 | 3.9 | [ |
19 | 568a | TCTA (15) | 0.059b | 1.03a | 18.5a | 1.6b | 580 | 1.8 | 1.0 | [ |
20 | 600a | mCP (10) | 0.14b | 5.5a | 15.8a | 2.2b | 600 | 2.0 | 2.1 | [ |
21 | 469b | – | 0.054f | 10a | 7a | 2.1b | – | – | – | [ |
22 | 490b | – | 0.051f | 45a | 16a | 1.6b | – | – | – | [ |
23 | 506b | – | 0.017f | 39a | 18a | 0.2b | – | – | – | [ |
24 | 516b | – | 0.022f | 16a | 30a | <0.1b | – | – | – | [ |
25 | 481b | – | 0.013f | 6a | 29a | 1.1b | – | – | – | [ |
26 | 504b | – | 0.053f | 19a | 46a | 1.0b | – | – | – | [ |
27 | 510b | mCP | 0.009f | 17a | 42a | 1.1b | 510 | 0.8 | 1.0 | [ |
28 | 493b | – | 0.136f | 18a | 25a | <0.1b | – | – | – | [ |
29 | 511b | – | 0.07f | 40a | 31a | <0.1b | – | – | – | [ |
30 | 519b | – | 0.075f | 22a | 47a | 0.7b | – | – | – | [ |
31 | 612b | – | – | 0.46h | 5.3h | 0.31h | – | – | – | [ |
32 | 670c | – | 0.28b | 0.9b | 1c | 0.25d | 716 | 1.9 | – | [ |
33 | 662c | – | 0.23b | 1.2b | 2c | 0.15d | 700 | 0.7 | – | [ |
34 | 537a | TCTA (8) | 0.18b | 170a | 86a | 0.3b | 530 | 27.6 | – | [ |
35 | 503a | 2,6-DCzPPy (8) | 0.12b | 75a | 77a | 5.3b | 506 | 20.5 | – | [ |
36 | 503b | 2,6-DCzPPy (10) | 0.037b | 7.7a | 92a | 0.56b | 501 | 32.6 | 2.34 | [ |
37 | 538b | 2,6-DCzPPy (10) | 0.09b | 13.5a | 85a | 1.88b | 544 | 12.3 | 2.3 | [ |
38 | 504b | mCP (15) | 0.04b | 3.2a | 73a | 0.7b | 502 | 15.0 | 0.8 | [ |
39 | 520b | mCP (15) | 0.05b | 2.7a | 87a | 0.39b | 514 | 20.3 | 0.5 | [ |
40 | 589b | CBP (15) | 0.16b | 3.6a | 92a | 1.9b | 548 | 28.3 | 0.6 | [ |
41 | 630b | CBP (7) | 0.07b | 3.7a | 89a | 0.4b | 600 | 20.3 | 2.4 | [ |
42 | 509a | mCBP (13) | 0.08c | 4.0a | 81a | 2.6b | 514 | 19.0 | 0.47 | [ |
43 | 493b | PhCzBCz (3) | 0.12b | 95.3a | 99b | 0.91a | 496 | 29.4 | 1.4 | [ |
44 | 500b | PhCzBCz (3) | 0.13b | 97.4a | 96b | 1.04a | 508 | 24.5 | 0.46 | [ |
45 | 505c | CBP (25) | 0.067c | 12.9a | 79.7c | 2.2b | 522 | 17.1 | 1.5 | [ |
46 | 458b | DPEPO (20) | 0.029a | 12.6a | 68.2a | 4.8a | 468 | 12.7 | 14 | [ |
47 | 497b | DPEPO (25) | 0.05a | 4.0a | 74a | 5.4b | 500 | 20.8 | – | [ |
48 | 543b | 2,6-DCzPPy (8) | 0.04b | 1.1b | 86.1b | 9.7b | 537 | 17.8 | – | [ |
49 | 485a | DPEPO (25) | 0.09b | 6.4a | 64a | 7.09b | 483 | 16.7 | 5.5 | [ |
50 | 482a | DPEPO (25) | 0.05b | 7.0a | 76a | 5.05b | 480 | 18.3 | 3.8 | [ |
51 | 529b | mCP (1) | 0.00f | 0.78a | 11b | 0.7 | – | – | – | [ |
52 | 530b | mCP (1) | 0.00f | 0.95a | 29b | 2.0 | – | – | – | [ |
53 | 492b | mCP (1) | 0.22f | 0.57a | 23b | 0.8 | – | – | – | [ |
54 | 482a | DPEPO (10) | 0.16a | 65a | 70a | 1.3b | 480 | 17.0 | – | [ |
55 | 527a | CBP (10) | 0.03b | 12.1a | 60a | 2.3b | 560 | 7.8 | 4.3 | [ |
56 | 565b | CBP (10) | 0.19f | 75a | 78a | 1.9b | 557 | 20.1 | 1.5 | [ |
57 | 522a | mCPCN (3) | 0.14b | 8.3b | 96a | 1.5b | 510 | 20.6 | 3.7 | [ |
58 | 512a | mCPCN (1) | 0.14b | 23.1b | 92a | 1.5b | 506 | 26.5 | 1.9 | [ |
59 | 660b | – | 0.22b | 16.4b | 100b | 2.0e | – | – | – | [ |
60 | 684b | – | 0.21b | 43.9b | 99b | 2.0e | – | – | – | [ |
61 | 696b | – | 0.18b | 26.8b | 90b | 1.5e | – | – | – | [ |
62 | 461b | mCBP (5) | 0.11b | 40.3a | 46.6a | 1.1b | 467 | 14.0 | 1.5 | [ |
63 | 446b | DPEPO (18) | 0.23b | 536a | 51.0a | 1.2e | 488 | 10.6 | 1.6 | [ |
64 | 473b | mCP (1) | 0.15a | 4.37a | 4.1a | 0.4b | – | – | – | [ |
65 | 539c | CBP (5) | – | 1.35c | 6.7c | 2.01c | 529 | 0.37 | – | [ |
66 | 542c | CBP (5) | – | 1.37c | 10.3c | 1.39c | 528 | 0.87 | – | [ |
67 | 487a | mCP (15) | 0.03a | 1.07a | 63a | 1.4a | 496 | 12.0 | 1.1 | [ |
68 | 532a | mCP (10) | 0.01a | 1.75a | 92a | 1.0a | 534 | 22.1 | 1.0 | [ |
69 | 547b | mCP (10) | 0.061f | 2.3a | 76a | 1.9a | 544 | 15.8 | 1.6 | [ |
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