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化学进展 2019, Vol. 31 Issue (6): 906-928 DOI: 10.7536/PC181005 前一篇   

• •

含硼有机发光二极管材料与器件

杨智文1, 詹迎迎1, 籍少敏1,2, 杨庆旦1, 李琦1, 霍延平1,2,*()   

  1. 1.广东工业大学轻工化工学院 广州 510006
    2.中国科学院上海有机化学研究所 有机氟化学中国科学院重点实验室 上海 200032
  • 收稿日期:2018-10-08 出版日期:2019-06-15 发布日期:2019-04-26
  • 通讯作者: 霍延平
  • 基金资助:
    国家自然科学基金项目(61671162); 广东省科技计划项目(2016A010103031); 广东省教育厅重点项目(2017KZDXM025)
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Boron-Containing Organic Light-Emitting Diodes: Materials and Devices

Zhiwen Yang1, Yingying Zhan1, Shaomin Ji1,2, Qingdan Yang1, Qi Li1, Yanping Huo1,2,*()   

  1. 1.School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, China
    2.Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
  • Received:2018-10-08 Online:2019-06-15 Published:2019-04-26
  • Contact: Yanping Huo
  • About author:
    ** E-mail:
  • Supported by:
    National Natural Science Foundation of China(61671162); Technology Plan of Guangdong Province(2016A010103031); Key Project of Educational Commission of Guangdong Province, China(2017KZDXM025)

硼元素因其独特的价层电子结构——价电子数少于价轨道数,而拥有一个空的p轨道,其三配位化合物既可以和邻近的π体系产生有效共轭,又可以容易地与路易斯碱发生络合,形成四配位化合物。将硼元素引入传统的光电功能分子当中,往往能给整个体系带来独特的光电性质,这已成为新型有机光电功能分子设计的重要思路。本文围绕硼元素的三配位化合物和四配位化合物,从分子设计理念、化合物光电性质、相关器件的结构与效率等方面对含硼有机光电功能分子及其器件的研究进展进行综述,并对其未来发展做出展望。

关键词： 硼, 有机发光二极管, 材料, 器件

Due to its unique valence electron distribution characteristics that the number of valence electron is less than the number of valence orbital, boron has an empty p orbit. It makes its tri-coordinated compounds can be effectively conjugated with the adjacent π system, and also can easily complex with the Lewis base to form a tetra-coordinated compound. The introduction of boron into traditional photoelectric functional molecules always brings unique photoelectric properties to the whole system, which has become an important idea for the design of new organic photoelectric functional molecules. In this paper, developments on tri-coordinated compounds and tetra-coordinated compounds of boron and performance of their OLED devices are reviewed around the aspects of molecular design, photoelectric properties of compounds, device structure and efficiency. The future development is also discussed.

Key words: boron, organic light-emitting diodes, materials, devices
()
图1 典型的三层OLED器件结构
Fig. 1 Typical structure of triple-layer OLED
图2 各代OLED器件发光机理示意图
Fig. 2 Luminescence Mechanism of various generations of OLEDs
图3 含硼有机光电功能分子设计原理
Fig. 3 Principles of designing organic boron-containing photoelectric functional molecules
表1 化合物1 ~ 3部分OLED器件的性能
Table 1 Performance of OLEDs using compounds 1~3
Compound Application Von/V Lmax/
cd·m-2		 ηp/
lm·w-1		 EQE/% λEL/nm ref
1 ETL 21 400 1.7 1.1 25
1 EML 3 1100 0.05 0.17 446,472 25
2 ETL 23 200 1.5 1.1 25
3 ETL 17 4130 0.48 0.8 27
表2 以化合物5~7为空穴阻挡层的OLED器件的性能
Table 2 Performance of OLEDs using compound 5 ~ 7 as HBL
Compound EML Von/V Lmax/
cd·m-2		 ηp/
lm·w-1		 EQE/% λEL/nm ref
5 α-NPD 3.2 3600 0.60 1.9 444 28
6 α-NPD 3.2 7100 0.72 2.1 444 28
7 α-NPD 3.2 9100 1.0 2.5 444 28
5 p-TTA 3.4 3500 0.58 1.9 435 28
6 p-TTA 3.4 7300 0.72 2.7 435 28
7 p-TTA 3.4 7400 0.78 2.8 435 28
5 TPD 3.4 790 0.12 0.89 404 28
6 TPD 3.4 2500 0.26 1.5 404 28
7 TPD 3.4 2600 0.33 1.5 404 28
表3 化合物11 ~18的OLED器件性能
Table 3 Performance of OLEDs using compounds 11 ~18
Compound Application Von/V Lmax/cd·m-2 ηp/lm·w-1 EQE/% λEL/nm CIE ref
11 EML 3.7 16 148 5.04 9.36 609 (0.58, 0.36) 33
12 EML 4.0 31 510 29.8 8.9 (0.35, 0.61) 34/37
13 ETL 3.0 5590 34.8 10.6 580 (0.51, 0.48) 35
14 EML 4.0 4165 41.6 17.9 (0.34, 0.53) 38
15 EML 3.6 2098 22.5 9.8 (0.27, 0.50) 38
16 ETL 3.5 27 756 24.9 17.5 612 (0.62, 0.38) 39
17 EML 3.4 59 154 50.1 28.5 604 (0.61, 0.39) 39
18 EML 3.3 33 659 18.8 11.3 604 (0.60, 0.40) 39
表4 化合物19 ~23的OLED器件性能
Table 4 Performance of OLEDs using compounds 19 ~23
Compound Application Von/V Lmax/cd·m-2 ηp/
lm·w-1		 EQE/% λEL/nm ref
19a EML 3.0 12 500 1.1 0.8 40
20a EML 3.0 23 700 1.3 1.0 40
20b EML 35 740 4.3 2.1 40
21a EML 13 800 1.8 1.6 479 41
22a EML 28 200 2.6 1.1 535 41
23a EML 16 600 0.9 0.6 562 41
表5 化合物24 ~ 40作为发光层的OLED器件性能
Table 5 Performance of OLEDs using compounds 24 ~ 40 as EML
Compound Von/V ηp/lm·w-1 EQE/% λEL/nm CIE ref
24 22.8 502 (0.22, 0.55) 42
25 21.6 492 (0.18, 0.43) 42
26 14.0 488 (0.17, 0.30) 42
27 21.7 43
28 19.0 43
29 20.1 (0.14, 0.16) 43
30 13.3 (0.14, 0.16) 43
31 15.1 466 44
32 22.1 503 44
33 16.0 479 (0.14, 0.24) 45
34 17.3 525 (0.28, 0.58) 45
37 4.4 8.0 463 (0.15, 0.17) 47
38 3.9 19.0 474 (0.15, 0.26) 47
39 2.7 121.6 37.8 528 (0.31, 0.61) 18
40 3.1 109.8 32.4 542 (0.37, 0.60) 18
表6 分子41 ~43作为发光层的 OLED器件性能
Table 6 Performance of OLEDs using compounds 41 ~43 as EML
Compound Von/V Lmax/cd·m-2 ηp/lm·w-1 EQE/% λEL/nm FWHM/nm CIE ref
41a 8.3 13.5 459 28 (0.13, 0.09) 48
42a 15.1 20.2 467 28 (0.12, 0.13) 48
43a 3.5 16 593 30.0 32.1 474 27 (0.12, 0.19) 49
43b 3.2 30 339 67.1 22.2 559 32 49
表7 化合物45 ~ 56的部分OLED器件性能
Table 7 Performance of OLEDs using compounds 45 ~ 56
Compound Application Von/V Lmax/cd·m-2 ηp/lm·w-1 λEL/nm CIE ref
45 EML&ETL 80 0.08 565 53
45 EML 100 0.1 575 53
47 EML (0.34, 0.49) 54
48 EML 4000 (0.43, 0.53) 54
54 EML 3.5~3.7 >1000 556 56
55 EML 3.5~3.7 >1000 587 56
56 EML 3.5~3.7 >1000 566 56
表8 化合物56 ~ 72的OLED器件性能
Table 8 Performance of OLEDs using compounds 56 ~ 72
Compound Application Von/V Lmax/cd·m-2 ηp/lm·w-1 λEL/nm CIE ref
57 EML&ETL 400~600 0.1 450 57
58 EML 4.1 1852 1.17 (0.26, 0.38) 58
59 EML 4.7 1323 0.79 (0.27, 0.44) 58
60 EML 3.5 1537 0.95 (0.27, 0.37) 58
61 EML 4.5 1271 0.70 (0.20, 0.33) 58
62 EML 3.8 2654 3.6 59
63 EML 5.4 2338 (0.28, 0.36) 60
64 EML 6.0 1507 (0.25, 0.34) 60
65 EML 6.0 1245 (0.29, 0.37) 60
66 EML 4.5 990 (0.28, 0.34) 60
67 EML 7.0 763 555 20
68 EML 7.5 2451 557 20
69 EML 7.5 206 598 20
70 EML 7.5 990 588 20
71 EML 7.4 1217 542 20
72 EML 6.5 1831 543 20
表9 化合物73 ~ 78的OLED器件性能
Table 9 Performance of OLEDs using compounds 73 ~ 78
Compound Application Von/V Lmax/cd·m-2 ηp/lm·w-1 λEL/nm CIE ref
73 EML 5.0 2237 2.6 465 (0.16, 0.19) 61
74 EML 4.8 3639 4.4 500 (0.19, 0.44)
75 EML 4.5 9181 1.8 544 (0.41, 0.55)
76 EML 3.0 31 220 4.8 560 (0.45, 0.53)
77 EML 4.5 14 010 3.1 612 (0.61, 0.39)
78 EML 4.0 4662 0.47 652 (0.66, 0.34)
表10 化合物79 ~ 81的OLED器件性能
Table 10 Performance of OLEDs using compounds 79 ~ 81
Compound Application Von/V Lmax/cd·m-2 ηp/lm·w-1 λEL/nm CIE ref
79 EML 5.0 2061 1.76 440 (0.15, 0.09) 51
80 EML 3.9 1412 1.41 432 (0.16, 0.08)
81 EML 4.1 2692 1.81 441 (0.16, 0.08)
表11 化合物82 ~ 85的OLED器件性能
Table 11 Performance of OLEDs using compounds 82 ~ 85
Compound Application Von/V Lmax/cd·m-2 ηp/lm·w-1 λEL/nm CIE ref
82 EML 3.0 4400 4.52 468 (0.19, 0.26) 50
83 EML 3.0 5065 5.42 492 (0.27, 0.46)
84 EML 3.0 2602 4.29 468 (0.19, 0.24)
85 EML 2.9 2392 3.09 445 (0.16, 0.08)
表12 化合物86 ~ 89的OLED器件性能
Table 12 Performance of OLEDs using compounds 86 ~ 89
Compound Application Von/V Lmax/cd·m-2 ηp/lm·w-1 λEL/nm CIE ref
86 EML 2.8 9041 7.58 476 (0.18, 0.30) 60
87 EML 3.0 6860 5.03 500 (0.27, 0.50)
88 EML 3.0 2118 4.88 468 (0.19, 0.24)
89 EML 3.2 4960 5.87 468 (0.19, 0.25)
表13 化合物90 ~ 94的部分OLED器件性能
Table 13 Performance of OLEDs using compounds 90 ~ 94
Compound Application Von/V Lmax/cd·m-2 ηp/lm·w-1 λEL/nm CIE ref
90 EML&ETL 2.6 8156 588 78
90 EML 2.4 8438 588
91 EML&ETL 3.2 8505 580
91 EML 2.5 9754 580
94 EML&ETL 3.2 2415 3.58 558 (0.40, 0.47) 49
表14 化合物96 ~ 122的部分OLED器件性能
Table 14 Performance of OLEDs using compounds 96 ~ 122
Compound Application Von/V Lmax/cd·m-2 EQE/% λEL/nm CIE ref
96 EML 7.0 450 62
99 EML 9.0 2300 490 (0.20, 0.33) 63
100 EML 11.0 141 64
107 EML 8.0 412 452 65
109 EML 157 432/636 65
113 EML 8.0 5000 (0.55, 0.45) 66
114 EML 3.5 332 543 (0.45, 0.53) 67
116 EML 320 400~750 (0.33, 0.37) 67
118 EML 1000 68
119 EML 1000 68
122 EML 4370 0.36 69
表15 化合物125 ~ 128的OLED器件性能
Table 15 Performance of OLEDs using compounds 125 ~ 128
Compound Application Von/V Lmax/cd·m-2 EQE/% λEL/nm CIE ref
125 EML 4 28 829 6.8 602 (0.49, 0.42) 78
126 EML 9.43 1.1 720 79
127 EML 8 2.1 626 80
128 EML ~10 >10 721 81
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摘要

含硼有机发光二极管材料与器件