中文 |
English |
Email Alert
基于8-羟基喹啉及其衍生物的有机小分子电致发光材料
苏斌1, 赵静1, 刘春波2*, 车广波1*, 王庆伟2, 徐占林2
化学进展 ›› 2013, Vol. 25 ›› Issue (07) :1090-1101
基于8-羟基喹啉及其衍生物的有机小分子电致发光材料
苏斌1, 赵静1, 刘春波2*, 车广波1*, 王庆伟2, 徐占林2
化学进展 ›› 2013, Vol. 25 ›› Issue (07) :1090-1101
基于8-羟基喹啉及其衍生物的有机小分子电致发光材料
Small Molecular Organic Electroluminescent Materials Based on 8-Hydroxyquinoline and Its Derivatives
有机电致发光器件因驱动电压低、亮度和效率高等优点,已经成为最具潜力的平板显示技术。自以8-羟基喹啉铝为发光材料制备双层有机电致发光器件开始,科研人员在发光材料设计合成方面做了大量工作并取得了重大研究进展。在小分子荧光材料中,8-羟基喹啉及其衍生物为配体的有机金属配合物因合成方法简单、发光效率和亮度高、成膜性好等优点而被广泛应用。本文简述了有机电致发光器件的优点、结构及工作原理,重点介绍了基于8-羟基喹啉及其衍生物为配体的有机小分子电致发光材料的研究现状。从分子设计的角度出发,旨在总结8-羟基喹啉及其衍生物为配体的有机小分子电致发光材料对有机电致发光器件性能的影响,包括:以8-羟基喹啉为单一配体的有机金属配合物展示了良好的电子传输能力、亮度高且可作为基质材料等卓越的特性;通过对8-羟基喹啉的苯氧环或吡啶环进行修饰可以调节电致发光颜色;混合配体的使用可以增加玻璃化温度、改善薄膜形貌进而提高器件的效率和稳定性。最后,对该领域存在的问题和有机电致发光材料的应用前景作了评述。
Organic light-emitting diodes (OLEDs) have emerged as a potential candidate for new flat panel display due to their advantages such as low driving voltage, high brightness and luminous efficiency. Since tris(8-hydroxyquinolinato)aluminum (Alq3)-based double layer thin-film device was prepared, much progress has been made in new electroluminescence (EL) materials which were designed and synthesized by researchers. Organic metal complexes based on 8-hydroxyquinoline and its derivatives are widely used due to simple synthesis, high luminance and efficiency as well as superior film morphology. This paper sketches the advantages, construction and working mechanism of OLEDs and stresses the research progress in small molecular organic EL materials based on 8-hydroxyquinoline and its derivatives as ligands. This article is written basically from the molecular design point of view and aims at the significant developments in metal organic complexes based on 8-hydroxyquinoline and its derivatives that have been designed and synthesized intentionally for OLEDs. Firstly, organic metal complexes based on 8-hydroxyquinoline as single ligand show favourable characteristics such as excellent electron-transport capability, high brightness and employment as host materials. Secondly, the EL colors could be tuned by modification of substituents at phenoxide or pyridine ring. Thirdly, the usage of mixed ligand can increase glass transition temperature and decorate morphology of film then result in high efficiency and stability. In the end, the current status, existing issues and prospects in this field are also discussed. Contents
1 Introduction
2 Structure and working mechanism of OLEDs
2.1 Structure of OLEDs
2.2 Working mechanism of OLEDs
3 Application of 8-hydroxyquinoline organic metal complexes in OLED
3.1 8-Hydroxyquinoline as single ligand
3.2 Derivatives of 8-hydroxyquinoline as ligands
3.3 Complexes of mixed-ligands
4 Conclusion and outlook
8-羟基喹啉
8-hydroxyquinoline
[1] Pope M, Kallmann H P, Magnante P. J. Chem. Phys., 1963, 38: 2042-2043
[2] Vincett P S, Barlow W A, Hann R A, Roberts G G. Thin Solid Films, 1982, 94: 171-183
[3] Tang C W, VanSlyke S A. Appl. Phys. Lett., 1987, 51: 913-915
[4] Lee J, Hofmann S, Thomschke M, Furno M, Kim Y H, Lüssem B, Leo K. Appl. Phys. Lett., 2011, 99: art. no. 073303
[5] Yang Q, Hao Y Y, Wang Z G, Li Y F, Wang H, Xu B S. Synth. Met., 2012, 162: 398-401
[6] Park J, Lee J, Noh Y Y. Org. Electron., 2012, 13: 184-194
[7] Moon B J, Yook K S, Lee J Y, Shin S, Hwang S H. J. Lumin., 2012, 132: 2557-2560
[8] Milián-Medina B, Gierschner J. Org. Electron., 2012, 13: 985-991
[9] Li T L, Li W L, Li X, Han L L, Chu B, Li M T, Hu Z Z, Zhang Z Q. Solid-State Electron., 2009, 53: 120-123
[10] Iwama Y, Itoh T, Mori T, Mizutani T. Thin Solid Films, 2006, 499: 364-368
[11] Chen W B, Lu L L, Cheng J B. Optik, 2010, 121: 107-112
[12] Kang I, Back J Y, Kim R, Kim Y H, Kwon S K. Dyes Pigm., 2011, 92: 588-595
[13] Kumar A, Srivastava R, Tyagi P, Mehta D S, Kamalasanan M N. Synth. Met., 2011, 161: 1172-1176
[14] Divayana Y, Liu S W, Kyaw A K K, Sun X W. Org. Electron., 2011, 12: 1-7
[15] Uddin A, Lee C B, Wong J. J. Lumin., 2011, 131: 1037-1041
[16] Lee C B, Uddin A, Andersson T G. Solid State Commun., 2007, 142: 206-211
[17] Kim M S, Lim J T, Jeong C H, Lee J H, Yeom G Y. Thin Solid Films, 2006, 515: 891-895
[18] Park H C, Park J W, Oh S G. Curr. Appl. Phys., 2010, 10: 1103-1107
[19] Hamada Y, Sano T, Fujita M, Fujii T, Nishio Y, Shibata K. Jpn. J. Appl. Phys., 1993, 32: L514-L515
[20] 郝玉英(Hao Y Y), 王华(Wang H), 郝海涛(Hao H T), 周禾丰(Zhou H F), 刘旭光(Liu X G), 许并社(Xu B S). 发光学报(Chinese Journal of Luminescence), 2004, 25(11): 419-424
[21] 朱海华(Zhu H H), 陈金伙(Chen J H), 胡加兴(Hu J X), 张福甲(Zhang F J). 功能材料与器件学报(Journal of Functional Materials and Devices), 2007, 13(1): 90-94
[22] Sano T, Nishio Y, Hamada Y, Takahashi H, Usuki T, Shibata K. J. Mater. Chem., 2000, 10: 157-161
[23] Burrows P E, Sapochak L S, McCarty D M, Forrest S R, Thompson M E. Appl. Phys. Lett., 1994, 64: 2718-2720
[24] 彭俊彪(Peng J B), 孙润光(Sun R G), 马於光(Ma Y G), 刘式墉(Liu S Y). 发光学报(Chinese Journal of Luminescence), 1994, 15(3): 263-266
[25] Xiang H F, Xu Z X, Roy V A L, Yan B P, Chan S C, Che C M, Lai P T. Appl. Phys. Lett., 2008, 92: art. no. 163305
[26] Hopkins T A, Meerholz K, Shaheen S, Anderson M L, Schmidt A, Kippelen B, Padias A B, Hall H K Jr, Peyghambarian N, Armstrong N R. Chem. Mater., 1996, 8: 344-351
[27] Pohl R, Anzenbacher P Jr. Org. Lett., 2003, 5: 2769-2772
[28] Montes V A, Li G, Pohl R, Shinar J, Anzenbacher P Jr. Adv. Mater., 2004, 16: 2001-2003
[29] Montes V A, Pohl R, Shinar J, Anzenbacher P Jr. Chem. Eur. J., 2006, 12: 4523-4535
[30] Pohl R, Montes V A, Shinar J, Anzenbacher P Jr. J. Org. Chem., 2004, 69: 1723-1725
[31] Liu N, Shi M M, Li Y Z, Shi Y W, Ran G Z, Qin G G, Wang M, Chen H Z. J. Lumin., 2011, 131: 199-205
[32] Fazaeli Y, Amini M M, Najafi E, Mohajerani E, Janghouri M, Jalilian A, Ng S W. J. Fluoresc., 2012, 22: 1263-1270
[33] Zlojutro V, Sun Y, Hudson Z M, Wang S N. Chem. Commun., 2011, 47: 3837-3839
[34] Gahungu G, Zhang J P. J. Phys. Chem. B, 2005, 109: 17762-17767
[35] Mishra A, Nayak P K, Periasamy N. Tetrahedron Lett., 2004, 45: 6265-6268
[36] Li L H, Xu B. Tetrahedron, 2008, 64: 10986-10995
[37] Ghedini M, Deda M L, Aiello I, Grisolia A. Inorg. Chim. Acta, 2004, 357: 33-40
[38] Xie J T, Ning Z J, Tian H. Tetrahedron Lett., 2005, 46: 8559-8562
[39] Kido J, Iizumi Y. Chem. Lett., 1997, 26: 963-964
[40] Matsumura M, Akai T. Jpn. J. Appl. Phys., 1996, 35: 5357-5360
[41] Yu J S, Chen Z J, Sakuratani Y, Suzuki H, Tokita M, Miyata S. Jpn. J. Appl. Phys., 1999, 38: 6762-6763
[42] Sapochak L S, Padmaperuma A, Washton N, Endrino F, Schmett G T, Marshall J, Fogarty D, Burrows P E, Forrest S R. J. Am. Chem. Soc., 2001, 123: 6300-6307
[43] Omar W A E, Haverinen H, Hormi O E O. Tetrahedron, 2009, 65: 9709-9712
[44] Heiskanen J P, Hormi O E O. Tetrahedron, 2009, 65: 8244-8249
[45] Irfan A, Cui R H, Zhang J P, Hao L Z. Chem. Phys., 2009, 364: 39-45
[46] Kumar A, Srivastava R, Bawa S S, Singh D, Singh K, Chauhan G, Singh I, Kamalasanan M N. J. Lumin., 2010, 130: 1516-1520
[47] 周亚东(Zhou Y D), 曾和平(Zeng H P), 靖慧莲(Jing H L), 袁国赞(Yuan G Z), 欧阳新华(OuYang X H). 有机化学(Chinese Journal of Organic Chemistry), 2006, 26(6): 783-792
[48] 杜乃婴(Du N Y), 梅群波(Mei Q B), 吕满庚(Lü M G). 功能材料(Journal of Functional Materials), 2004, 35(z1): 238-246
[49] 赵玉玲(Zhao Y L), 俞天智(Yu T Z). 材料导报(Materials Review), 2007, 21(4): 21-25
[50] 周瑞(Zhou R), 安忠维(An Z W), 柴生勇(Chai S Y). 光谱学与光谱分析(Spectroscopy and Spectral Analysis), 2004, 24(8): 922-926
[51] Shi Y W, Shi M M, Huang J C, Chen H Z, Wang M, Liu X D, Ma Y G, Xu H, Yang B. Chem. Commun., 2006, (18): 1941-1943
[52] 陈柳青(Chen L Q), 刘旭光(Liu X G), 许慧侠(Xu H X), 王华(Wang H), 许并社(Xu B S). 中国材料进展(Materials China), 2009, 28(3): 22-25
[53] Tao X T, Suzuki H, Wada T, Miyata S, Sasabe H. J. Am. Chem. Soc., 1999, 121: 9447-9448
[54] Yin S G, Hua Y L, Chen X H, Yang X H, Hou Y B, Xu X R. Synth. Met., 2000, 111/112: 109-112
[55] Ma D G, Wang G, Hu Y F, Zhang Y G, Wang L X, Jing X B, Wang F S, Lee C S, Lee S T. Appl. Phys. Lett., 2003, 82: 1296-1298
[56] Yang K S, Shin H K, Kim C, Kwon Y S. Synth. Met., 2005, 152: 245-248
[57] Yang K S, Lee H S, Kim S U, Jang Y K, Kim D S, Shin H K, Kwon Y S, Kim C. Int. J. Nanosci., 2006, 5: 859-864
[58] Ghedini M, Deda M L, Aiello I, Grisolia A. Synth. Met., 2003, 138: 189-192
[59] Du N Y, Mei Q B, Lu M G. Synth. Met., 2005, 149: 193-197
[60] Mishra A, Periasamy N, Patankar M P, Narasimhan K L. Dyes Pigm., 2005, 66: 89-97
[61] Shao Y, Qiu Y, Hu X M, Hong X Y. Chem. Lett., 2000, 29: 1068-1069
[62] Anderson S, Weaver M S, Hudson A J. Synth. Met., 2000, 111: 459-463
[63] Cui Y, Liu Q D, Bai D R, Jia W L, Tao Y, Wang S N. Inorg. Chem., 2005, 44: 601-609
[64] Kappaun S, Rentenberger S, Pogantsch A, Zojer E, Mereiter K, Trimmel G, Saf R, Möller K C, Stelzer F, Slugovc C. Chem. Mater., 2006, 18: 3539-3547
[65] Xu B S, Chen L Q, Liu X G, Zhou H F, Xu H X, Fang X H, Wang Y L. Appl. Pyhs. Lett., 2008, 92: art. no. 103305
[66] Petrova P K, Tomova R L, Stoycheva-Topalova R T, Kaloyanova S S, Deligeorgiev T G. J. Lumin., 2012, 132: 495-501
[67] Su B, Liu C B, Wang Q W, Che G B. Optoelectron. Adv. Mat., 2011, 5: 587-589
[68] 苏斌(Su B), 袁晶(Yuan J), 荣光怡(Rong G Y). 吉林师范大学学报(Journal of Jilin Normal University), 2011, 32(4): 126-128
[69] Jang H, Do L M, Kim Y, Kim J G, Zyung T, Do Y. Synth. Met., 2001, 121: 1669-1670
[70] Hamada Y, Kanno H, Sano T, Fujii H, Nishio Y, Takahashi H, Usuki T, Shibata K. Appl. Phys. Lett., 1998, 72: 1939-1941
[71] Giro G, Cocchi M, Marco P D, Fattori V, Dembech P, Rizzoli S. Synth. Met., 2001, 123: 529-533
[72] Pérez-Bolívar C, Montes V A, Anzenbacher P Jr. Inorg. Chem., 2006, 45: 9610-9612
[73] Leung L M, Lo W Y, So S K, Lee K M, Choi W K. J. Am. Chem. Soc., 2000, 122: 5640-5641
[74] Qiu Y, Shao Y, Zhang D Q, Hong X Y. Jpn. J. Appl. Phys., 2000, 39: 1151-1153
[75] Wong K Y, Lo C F, Sham W Y, Fong H H, So S K, Leung L M. Phys. Lett. A, 2004, 321: 194-198
[76] Wang G, He Y, Wang L X. Mater. Lett., 2008, 62: 2611-2614
[77] Qin Y, Kiburu I, Shah S, Jäkle F. Org. Lett., 2006, 8: 5227-5230
[78] Kwong C Y, Djuriši Dc' A B, Choy W C H, Li D, Xie M H, Chan W K, Cheah K W, Lai P T, Chui P C. Mat. Sci. Eng. B, 2005, 116: 75-81
[79] Itoh T, Mizutani T, Mori T. Colloids and Surfaces A: Physicochem. Eng. Aspects, 2006, 284/285: 594-598
[80] Chen P Y, Ueng H Y, Yokoyama M. J. Lumin., 2010, 130: 1764-1767
[81] Kim J H, Yoon D Y, Kim J W, Kim J J. Synth. Met., 2007, 157: 743-750
[82] Jung S O, Kim Y H, Kwon S K, Oh H Y, Yang J H. Org. Electron., 2007, 8: 349-356
[83] Wang Y, Hua Y L, Wu X M, Zhang L J, Hou Q C, Liu Q. Org. Electron., 2008, 9: 273-278
[84] Lim J T, Jeong C H, Lee J H, Yeom G Y, Jeong H K, Chai S Y, Lee I M, Lee W I. J. Organomet. Chem., 2006, 691: 2701-2707
[85] 邵炎(Shao Y), 刘宇宏(Liu Y H), 邱勇(Qiu Y). 功能材料(Journal of Functional Materials), 2001, 32(6): 662-663
[86] Katkova M A, IIichev V A, Konev A N, Bochkarev M N, Vitukhnovsky A G, Parshin M A, Pandey L, Auweraer M V. J. Appl. Phys., 2008, 104: art. no. 053706
[87] Shi L L, Geng Y, Gao H Z, Su Z M, Wu Z J. Dalton Trans., 2010, 39: 7733-7740
[88] Leung C F, Ng S M, Xiang J, Wong W Y, Lam M H W, Ko C C, Lau T C. Organometallics, 2009, 28: 5709-5714
[89] Kunkely H, Vogler A. Inorg. Chim. Acta, 2009, 362: 196-198
[90] Khreis O M, Gillin W P, Somerton M, Curry R J. Org. Electron., 2001, 2: 45-51
[91] Cheng Y M, Yeh Y S, Ho M L, Chou P T. Inorg. Chem., 2005, 44: 4594-4603
[92] Xu H, Huang L F, Guo L M, Zhang Y G, Ren X M, Song Y, Xie J. J. Lumin., 2008, 128: 1665-1672
[93] Ghedini M, Aiello I, Deda M L, Grisolia A. Chem. Commun., 2003, 2198-2199
[94] Shavaleev N M, Adams H, Best J, Edge R, Navaratnam S, Weinstein J A. Inorg. Chem., 2006, 45: 9410-9415
[95] Kappaun S, Sax S, Eder S, Möller K C, Waich K, Niedermair F, Saf R, Mereiter K, Jacob J, Müllen K, List E J W, Slugovc C. Chem. Mater., 2007, 19: 1209-1211
[96] Yi C, Yang C J, Liu J, Xu M, Wang J H, Cao Q Y, Gao X C. Inorg. Chim. Acta, 2007, 360: 3493-3498
[97] Niu J H, Li W L, Wei H Z, Li M T, Su W M, Xin Q, Zhang Z Q, Hu Z Z. J. Phys. D: Appl. Phys., 2005, 38: 1136-1139
[98] Lim J T, Lee M J, Lee N H, Ahn Y J, Lee C H, Hwang D H. Curr. Appl. Phys., 2004, 4: 327-330
[99] Nayak P K, Agarwal N, Ali F, Patankar M P, Narasimhan K L, Periasamy N. J. Chem. Sci., 2010, 122: 847-855
[100] Tyagi P, Srivastava R, Kumar A, Rai V K, Grover R, Kamalasanan M N. Synth. Met., 2010, 160: 756-761
[101] Kim D E, Kim W S, Kim B S, Lee B J, Kwon Y S. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2008, 313/314: 320-323
/
| 〈 |
|
〉 |
PDF
(1259KB)
