环金属化合物发光材料的合成与性质
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摘要
环金属化铱配合物具有发光效率高、发光颜色可以通过改变配体结构进行调节及磷光寿命较短等优点而成为研究的热点。而详细研究配体化学结构与配合物发光性能的关系(即构效关系)的研究和阐明配合物的发光机理是设计新型、高效发光材料的理论基础和关键因素。
本论文设计并合成了一系列新型以2-苯基喹啉为主配体、酰胺化合物为辅助配体的新型环金属化铱配合物的有机发光材料。先对氯桥二聚铱配合物(pq)_2Ir(μ-Cl)_2Ir(pq)_2(其中pq=2-phenylquinoline)中Ir-Cl键的稳定程度进行研究,合成得到了吡啶的铱配合物(pq)_2Ir(pyridine)Cl。具体的合成方案为:将吡啶与氯桥二聚铱配合物(pq)_2Ir(μ-Cl)_2Ir(pq)_2在二氯甲烷溶液中回流生成目标的配合物(pq)_2Ir(pyridine)Cl。然后合成了酰胺的铱配合物,具体的合成方案为:将酰胺化合物与氯桥二聚铱配合物(pq)_2Ir(μ-Cl)_2Ir(pq)_2在高温、弱碱存在的条件下反应生成目标的化合物——(pq)_2Ir(acetylaniline),(pq)_2Ir(N-tert-butylbenzamide),(pq)_2Ir(N-phenylbenzamide)及(pq)_2Ir(pyridine)。对所得到的产物进行了红外、核磁、单晶衍射及元素分析表征,确定了所得配合物为目标产物。
并对得到的配合物进行了紫外和荧光的光学性质研究。此类化合物都具有相类似的紫外和荧光光谱,但由于结构不同,紫外吸收波长和荧光发射波长都存在不同程度的位移。荧光光谱表明,此类配合物在590nm左右有强的荧光发射,表明这些化合物是良好的红光发光材料。同时对这些配合物通过循环伏安法测定了电化学性质,并以此确定了其HOMO和LOMO能级。此类配合物有较好的氧化-还原可逆性,其良好的发光性能及稳定性使此类材料具有很好的应用前景。
Recently, iridium complex have received considerable attention because of their high emission efficiencies and easy tuning of emission colors by changing chemical structures of ligands.An efficacious solution to this problem is to modify the structrure of ligands or introduce phosphorescent dye into the polymer chain by grafting.
In this thesis a series of heteroleptic cyclometalate Ir complexes with acylamide derivants as ancillary ligands (pq)_2Ir(LX) (pq=2-phenylquinoline,LX=acetylaniline, N-phenylbenzamide,N-tert-butylbenzamide,pyridine) have been successfully synthesized. At first, the iridium complexe containing pyridine ligands was synthesized in order to confirm the stabilization of Ir-Cl bond. The synthetic procedures are as follows: (pq)_2Ir(μ-Cl)_2Ir(pq)_2 was refleuxed with pyridine, and obtained the (pq)_2Ir(pyridine)Cl. Then the Ir complexes containing amides ligands were synthesized. The synthetic procedures are as follows:Stirred the dicholoro-phenylquinoline complex and amide derivants in the presence of alkali in 2-ethoxyethanol to give birth to the aimed complexes,these are (pq)_2Ir(acetylaniline), (pq)_2Ir(pyridine),(pq)_2Ir(N-Phenylbenzamide),(pq)_2Ir(N-tert-butylbenzamide).All of the structures of complexes were characterized by HNMR, x-ray single crystal diffusion or element analysis.
All the complexes give rise to resemble absorptions at around 260nm, and their solution emissions are all fell into the red light region but differ in the max emission wavelength around 590nm, which prove all the complexes are red phosphorescence complexes. The cyclic voltammetry spectra of these complex show that they are redox reversibility The stability of devices can be expected due to their excellent redox stabilities.
本论文设计并合成了一系列新型以2-苯基喹啉为主配体、酰胺化合物为辅助配体的新型环金属化铱配合物的有机发光材料。先对氯桥二聚铱配合物(pq)_2Ir(μ-Cl)_2Ir(pq)_2(其中pq=2-phenylquinoline)中Ir-Cl键的稳定程度进行研究,合成得到了吡啶的铱配合物(pq)_2Ir(pyridine)Cl。具体的合成方案为:将吡啶与氯桥二聚铱配合物(pq)_2Ir(μ-Cl)_2Ir(pq)_2在二氯甲烷溶液中回流生成目标的配合物(pq)_2Ir(pyridine)Cl。然后合成了酰胺的铱配合物,具体的合成方案为:将酰胺化合物与氯桥二聚铱配合物(pq)_2Ir(μ-Cl)_2Ir(pq)_2在高温、弱碱存在的条件下反应生成目标的化合物——(pq)_2Ir(acetylaniline),(pq)_2Ir(N-tert-butylbenzamide),(pq)_2Ir(N-phenylbenzamide)及(pq)_2Ir(pyridine)。对所得到的产物进行了红外、核磁、单晶衍射及元素分析表征,确定了所得配合物为目标产物。
并对得到的配合物进行了紫外和荧光的光学性质研究。此类化合物都具有相类似的紫外和荧光光谱,但由于结构不同,紫外吸收波长和荧光发射波长都存在不同程度的位移。荧光光谱表明,此类配合物在590nm左右有强的荧光发射,表明这些化合物是良好的红光发光材料。同时对这些配合物通过循环伏安法测定了电化学性质,并以此确定了其HOMO和LOMO能级。此类配合物有较好的氧化-还原可逆性,其良好的发光性能及稳定性使此类材料具有很好的应用前景。
Recently, iridium complex have received considerable attention because of their high emission efficiencies and easy tuning of emission colors by changing chemical structures of ligands.An efficacious solution to this problem is to modify the structrure of ligands or introduce phosphorescent dye into the polymer chain by grafting.
In this thesis a series of heteroleptic cyclometalate Ir complexes with acylamide derivants as ancillary ligands (pq)_2Ir(LX) (pq=2-phenylquinoline,LX=acetylaniline, N-phenylbenzamide,N-tert-butylbenzamide,pyridine) have been successfully synthesized. At first, the iridium complexe containing pyridine ligands was synthesized in order to confirm the stabilization of Ir-Cl bond. The synthetic procedures are as follows: (pq)_2Ir(μ-Cl)_2Ir(pq)_2 was refleuxed with pyridine, and obtained the (pq)_2Ir(pyridine)Cl. Then the Ir complexes containing amides ligands were synthesized. The synthetic procedures are as follows:Stirred the dicholoro-phenylquinoline complex and amide derivants in the presence of alkali in 2-ethoxyethanol to give birth to the aimed complexes,these are (pq)_2Ir(acetylaniline), (pq)_2Ir(pyridine),(pq)_2Ir(N-Phenylbenzamide),(pq)_2Ir(N-tert-butylbenzamide).All of the structures of complexes were characterized by HNMR, x-ray single crystal diffusion or element analysis.
All the complexes give rise to resemble absorptions at around 260nm, and their solution emissions are all fell into the red light region but differ in the max emission wavelength around 590nm, which prove all the complexes are red phosphorescence complexes. The cyclic voltammetry spectra of these complex show that they are redox reversibility The stability of devices can be expected due to their excellent redox stabilities.
引文
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2. Burroughes J H, Bradley D C, Brown A R, etc, Light emitting diodes based on conjugated polymers[J]. Nature, 1990, 347: 539-541
3.黄春辉,李富友,黄维.有机电致发光材料与器件导论[M].上海:复旦大学出版社, 2005.315-384
4.张建成,王夺元,现代光化学[M].化学工业出版社. 2006. 274-280
5. Baldo, O’Brien, etc. Highly efficient phosphoresecent emission from organic electroluminescent devices[J]. Nature 1998, 395(6698): 151-154
6. Gu G, Parthasarathy G, Forrest S R. A metal-free full-color stacked organic light-emitting device[J]. ApplPhysLett, 1999, 74(2): 305-308
7.甄宏宇,杨伟,朱卫国,等.利用三线态激子提高有机高分子发光器件的量子效率[J].化学进展,2004,16(1):99-104
8. Tang C W, VanSlyke S A, And C. Electroluminescence of doped organic thin film[J]. J Appl Phys, 1989, 65(9): 3610-3616
9.吴世康,李述汤,张晓宏.磷光电致发光器件研究中的若干问题[J].化学进展, 2001, 13,413-419
10. Hamada Y, Kanno H, Tsujioka T, etc. Red orangic light-emitting diodes using an emitting assist dopant[J]. Appl Phys Lett, 1999, 75(12): 1682-1684
11. Kawamura Y, Goushi K, Brooks J, etc. al.100% phosphorescence quantum efficiency of Ir(Ⅲ) complexes in organic semiconductor films[J]. Appl Phys Lett, 2005, 86(7):1-3
12. Takaya M, Douglas J, Roy A, etc. Anti-Markovnikov olefin arylation catalyzed byan iridium complex [J]. J.Am.Chem.Soc.2000,122,7414-7415
13. Tanaka D, Sasabe H, Li Y J. Ultra high efficiency green organic light-emitting devices[J]. J Appl Phys, 2007, 46(1): L10-L12
14. Jason B, Yelizaveta B, sergey L, etc. Synthesis and characterization of phosphorescent cyclometalated platinum complexes[J]. Inorg Chem, 2002, 41: 3055-3066
15. Carlson B, Gregory P, Kaminsky W, etc. Divalent osmium complexes: Synthesis, characterization, strong red phosphorescence, and electrophosphorescence[J]. J Am Chem Soc, 2002, 124: 14162
16.卞祖强,高德青,关敏,等.不同邻菲洛琳衍生物作为中性配体的三元铕配合物电致发光性质研究[J].中国科学(B辑), 2004, 34:113
17.陈芳芳,卞祖强,黄春辉,等.铕配合物电致发光研究进展[J].中国稀土学报, 2007, 25(4):385-395
18.黄岩谊,于安池,黄春辉,等,强荧光铽配合物LB膜光学微腔[J].高等学校化学学报, 1998, 19:1375-1377
19. Lo L, Kenneth K, Kenneth Y, etc.Synthesis, photophysical and electrochemical properties, and protein-binding studies of luminescent cyclometalated iridium(III) bipyridine estradiol conjugates[J]. Chemistry 2007, 13(25), 7110-7120
20. Jiang J, Jiang C, Yang W, etc.High-efficiency electrophosphorescent fluorene-alt-carbazole copolymers N-Grafted with cyclometalated Ir complexes[J].Macromolecules.2005,38(10), 4072-4080
21. Kenneth Kam W, Joe Sai Wan C, Chi Keung C, etc.Synthesis, photophysical and electrochemical properties, and biological labelling studies of luminescentcyclometallatediridium(III) bipyridine–aldehyde complexes[J]. Inorganica Chimica Acta 2004, 357: 3109-3118
22. Mark E T, Peter D, Sergey L, etc. Organometallic complexes a phosphorescent emitters in organic leds[P].US.Patent. 20040127710A1, 2004-7-1
23. Thompson, Peter D, Sergey L, etc. Organometallic complexes a phosphorescent emitters in organic leds[P].US.Patent.6830828 B2, 2004-12-24
24. Baldo M A, Lamansky S, Burrows P E, etc. Very high-efficiency green organic light-emitting devices based on electrophosphorescence[J]. Appl. Phys. Lett. 1999,75:4-6
25. Tsutsui T, Yang M J, Yahiro M, etc. High quantum efficiency in organic light-emitting devices with Iridium-complex as a triplet emissive center[J]. Jpn.J.Appl.Phys.Part2, 1999, 38: L1502-L1504
26. Lamansky S, Djurovich P., Murphy D., etc, Synthesis and characterization of phosphorescent cyclometalated Iridium complexes[J]. Inorg.Chem. 2001, 40:1704-1711
27. Suzuki T, Shirasawa, Suzuki, etc Organic light-emitting diodes using pentafluorophenyl-substituted Iridium complexes[J]. Adv.Mater.2003, 15: 1455-1458
28. Huang W, Lin J T, Chien C H, etc. Highly phosphorescent bis-cyclometalated iridium complexes containing benzoimidazole-based ligands[J]. Chem.Mater.2004,16:2480-2488
29. Frederick J., Michael S., Oyler K, etc. Synthesis, separation, and circularly polarized luminescence studies of enantiomers of Iridium(III) luminophores[J]. Inorg Chem 20
08, 47(6): 2039-2048
30. Yeh S J, Wu M F, Chen C T, etc. New dopant and host materials for blue-light-emitting phosphorescent organic electroluminescent devices[J].Adv.Mater,2005,17:285-289
31. Tokito, Lijima T, Tsuzuki T., etc, High-efficiency white phosphorescent organic light-emitting devices with greenish-blue and red-emitting layers[J]. Appl.Phys.Lett. 2003,83: 2459-2461
32. Holmes R J., Forrest S R., Tung Y J., etc. Blue organic electrophosphorescence using exothermic host-guest energy transfer[J]. Appl.Phys.Lett. 2003, 82: 2422-2424
33. Coppo P., Plummer E A., Cola L D. Tuning iridium(Ⅲ)complexes inthe“almost blue”region[J]. Chem.Commun. 2004, 1774-1775
34. Tao L, Xia B H, Xin Z, etc. Theoretical studies on structures and spectroscopic properties of bis-cycloetalated iridium complexes[J]. Organometallics 2007(26):143-149
35. Cheuk L, Lin, Mei F, etc. High-efficiency and color-stable white organic light-emitting devices based on sky blue electrofluorescence and orange electrophosphorescence[J]. Applied Physics Letters.2008, 92(8): 083301/1-083301/3
36. Yuan-Min W, Teng Feng G, hua L, etc. Blue light-emitting bisorthometalated Ir(III) complex: origin of blue emission and application in electrophosphorescent devices[J].Journal of Physical Chemistry C, 2008, 112(12), 4743-4747
37. Adachi C., Baldo M.A, Forrest S R., etc. High-efficiency red electrophosphorescence devices[J]. Appl.Phys.Lett. 2001(78):1622-1624
38. Seo Ji H, Seung Ch, Yong H, etc. Red electrophosphorescent devices based on heteroleptic tris-cyclometalated iridium complexes with fluorinated 2,4-diphenylquinoline ligands[J]. Molecular Crystals and Liquid Crystals. 2007, 471:305-312
39. Jung K, Jeong S, Hyun C, etc. Red phosphorescent compounds and organic electroluminescent devices using the same[P]. US.Patent.20070104980A1.2007-3-10
40. Youngmin Y, Cheng-Guo K, Jang J, etc. A deep red phosphorescent Ir(III) complex for use in polymer light-emitting diodes: role of the arylsilyl substituents[J]. Journal of Organic Chemistry, 2007, 72(16):6241-6246
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