CN102558238A - Iridium complexes containing guanidine group and application of iridium complexes to preparation of electroluminescent devices - Google Patents

Iridium complexes containing guanidine group and application of iridium complexes to preparation of electroluminescent devices Download PDF

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CN102558238A
CN102558238A CN2011103996612A CN201110399661A CN102558238A CN 102558238 A CN102558238 A CN 102558238A CN 2011103996612 A CN2011103996612 A CN 2011103996612A CN 201110399661 A CN201110399661 A CN 201110399661A CN 102558238 A CN102558238 A CN 102558238A
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iridium
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organic electroluminescent
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刘宇
王悦
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吉林大学
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Abstract

The invention belongs to the technical field of organic electroluminescence, and in particular relates to iridium complexes containing a guanidine group ligand and application of the iridium complexes to the preparation of electroluminescent devices. The compounds have the advantages that: the compounds are easy to prepare and low in cost, have high electroluminescent properties, and can be further used as luminescent layers of organic electroluminescent devices, and high-performance electroluminescent devices with the emission spectra covering a green light area and a red light area are obtained and can be used in application fields of illuminating sources, signal lamps, alphanumeric displays, signposts, photoelectric couplers, flat panel displays and the like.

Description

含有胍基团的铱配合物及在制备电致发光器件方面的应用 Iridium complex containing a guanidine group, and aspects of the electroluminescent device prepared in electrical applications

技术领域 FIELD

[0001] 本发明属于有机电致发光技术领域,具体涉及一类含有胍基团配体的铱配合物以及这些铱配合物在制备电致发光器件方面的应用。 [0001] The present invention pertains to organic electroluminescent technology, and in particular the application relates to a class of guanidino groups of the ligands and iridium complexes in which iridium complex prepared aspect an electroluminescent device.

背景技术 Background technique

[0002] 作为新一代的显示技术,有机电致发光器件或称有机发光二极管(OLED),以其无以伦比的优势吸引了众多人的目光,国内外无数的科学家和各大电子厂商都投入了大量的精力和资金来研究它,使其进入了实用化阶段。 [0002] As a new generation of display technology, organic electroluminescent devices also known as organic light emitting diode (OLED), with its unparalleled advantages attracted many people's eyes, numerous domestic and foreign scientists and major electronics manufacturers have invested a lot of energy and money to research it and make it into a practical stage. 另外,电致发光技术在白光照明领域也有着巨大的潜在市场,将在不久的将来作为新一代的照明光源得到应用。 Further, white light electroluminescent lighting technology also has a huge potential market, next-generation lighting source as applied in the near future. 回顾有机电致发光的历史,Pope等人于二十世纪六十年代初最早报道了这一现象,他们在蒽单晶两侧施加四百伏的高压时观察到了蒽发出的蓝光。 Recalling the organic electroluminescent history, Pope, who in the early 1960's was first reported the phenomenon was observed when four hundred kilovolts emitted blue light anthracene they applied to both sides of the anthracene single crystal. 但是由于单晶难于生长,器件驱动电压很高GOO〜 2000V),他们所采用的工艺几乎没有实际用途。 However, since the crystal growth is difficult, the device driving voltage is high GOO~ 2000V), they adopt the process of little practical use. 直到1987年,美国Kodak公司的CW Tang 等人采用超薄膜技术以空穴传输效果较好的芳香胺作为空穴传输层,以8-羟基喹啉的铝配合物作为发光层,以氧化铟锡(ITO)薄膜和金属合金分别作为阳极和阴极,制备了发光器件。 Until 1987, the US Kodak Company CW Tang et al ultra thin-film technology to better hole transport aromatic amine as a hole transporting layer, 8-hydroxyquinoline to the aluminum complex as a light emitting layer, indium tin oxide (ITO) films and metal alloys as anode and cathode, respectively, the light emitting device was produced. 该器件在IOV驱动电压下得到了亮度高达lOOOcd/m2的绿光发射,器件的效率为1.51m/W(lC.W.Tang and SA VanSlyke,Appl. Phys. Lett.,1987,51,913)。 The device is obtained at a driving voltage of the brightness up IOV lOOOcd / m2 of green light emission efficiency of the device is 1.51m / W (lC.W.Tang and SA VanSlyke, Appl. Phys. Lett., 1987,51,913) . 这一突破性进展使得有机电致发光研究得以在世界范围内迅速深入地开展起来。 This breakthrough makes it light-emitting organic electroluminescent research rapidly intensified and up in the world.

[0003] 1998年美国普林斯顿大学的!Arrest等人研究发现,使用一般有机材料或采用荧光染料掺杂技术制备的有机发光器件,由于受自旋守恒的量子力学跃迁规律约束,其最大发光内量子效率为25%。 [0003] In 1998! Arrest et al U.S. Princeton University found that, using a general organic material or fluorescent dye-doped organic light-emitting device preparation technique, the transition due to the law of conservation of spin quantum mechanics, bound, within the maximum emission quantum efficiency of 25%. 他们将磷光染料八乙基卟啉钼(PtOEP)掺杂于主体发光材料中, 制备出外量子效率为4%,内量子效率达23%的发光器件,从而开辟了磷光电致发光的新领域(见MA Baldo, DF 0' Brien et al.,Nature, 1998,395,151)。 They phosphorescent dye molybdenum octaethylporphyrin (PtOEP) doped with luminescent material in the body, go prepared 4% quantum efficiency, internal quantum efficiency of 23% of the light emitting device, thus opening up a new field of electroluminescent phosphorus ( see MA Baldo, DF 0 'Brien et al., Nature, 1998,395,151). 有机电致绿色磷光材料是研究最早,也是发展最成熟的一类材料。 Green phosphorescent organic electroluminescent material is the earliest research, but also the most mature class of materials. 1999年,MA Baldo等将三(2-苯基吡啶) 铱(IHppy)3)掺杂到4,4' -N, N' - 二咔唑联苯(CBP)中,器件的最大外量子效率和功率效率分别为8. 0%和311m/W,从此掀起了重金属配合物电磷光材料和器件研究的热潮(见MA Baldo, S. Lamanskv, PE Burrows, et al, Appl. Phys. Lett.,1999,75,4-6)。 In 1999, MA Baldo et tris (2-phenylpyridine) iridium (IHppy) 3) to the doped 4,4 '-N, N' - dicarbazole-biphenyl (CBP), the maximum external quantum efficiency of the device and the power efficiency was 8.0%, respectively, and 311m / W, set off from the heavy metal complex electrical materials and devices research boom phosphors (see MA Baldo, S. Lamanskv, PE Burrows, et al, Appl. Phys. Lett., 1999,75,4-6). 由于具有非常高的效率和亮度,有机磷光配合物在未来的有机固态照明领域有着较强的应用前景。 Due to the very high efficiency and luminance, organic phosphorescent complex has a strong future potential applications in organic solid-state lighting. 但是,由于目前报道的磷光配合物存在较为严重的三重态-三重态湮灭以及较差的载流子传输能力,该类配合物往往要在很低、很窄的掺杂浓度范围内才能实现高性能的电致发光, 这就要求较为苛刻的器件制备条件,从而导致产业化生产中的较高的成本,影响产品的品质和商业竞争能力。 However, due to the presence of more serious triplet phosphorescent complexes reported to date - to achieve the high triplet annihilation and poor carrier transport capability, such complexes tend to be very low, very narrow concentration range of doping EL electrical properties, which requires more stringent conditions preparation device, resulting in higher cost of industrial production, affecting the quality and commercial competitiveness of products.

[0004] 新材料的开发是推动电致发光技术不断进步并进入实用化阶段的必需手段。 [0004] The development of new materials are necessary means of promoting electroluminescent technology advances and into the practical stage. 近年来,人们对新材料的开发投入了巨大的财力和精力,大量性能优良的材料使有机电致发光取得了一些突破性进展(见US Pat. No. 5,150,006 ;5,141,671 ;5,073,446 ;5,061,569 ; 5,059,862 ;5,059,861 ;5,047,687 ;4,950,950 ;5,104,740 ;5,227,252 ;5,256,945 ; 5,069,975 ;5,122,711 ;5,554,450 ;5,683,823 ;5,593,788 ;5,645,948 ;5,451,343 ;5,623,080 ;5,395,862)。 In recent years, the development of new materials into a huge money and effort, a lot of excellent material properties of the organic electroluminescent made some breakthrough (see US Pat No. 5,150,006;. 5,141, 671; 5,073,446; 5,061,569; 5,059,862; 5,059,861; 5,047,687; 4,950,950; 5,104,740; 5,227,252; 5,256,945; 5,069,975; 5,122,711; 5,554,450; 5,683,823; 5,593,788; 5,645,948; 5,451,343; 5, 623,080; 5,395,862). 发明内容 SUMMARY

[0005] 本发明的目的在于提供一系列新的含有胍基团配体的铱配合物,及将其作为有机电致发光材料(化合物1-14)应用于制备高性能的有机电致发光器件。 [0005] The object of the present invention to provide a new series of iridium complexes containing ligands of the guanidine group, and which as an organic electroluminescent material (Compound 1-14) are applicable to the preparation of high performance organic electroluminescent device . 本发明旨在开发新的电致发光材料,涉及的材料具有易于制备、成本低廉的优点,并具有较好的电致发光性能。 The present invention is aimed at developing new electroluminescent material, having a material according to ease of preparation, the advantages of low cost, and has good electroluminescent properties.

[0006] 化合物1-14的合成路线如下图所示。 Synthetic Route [0006] Compound 1-14 as shown in FIG. 化合物1-14分别在氮气保护下以正己烷为 Compound 1-14, respectively, under a nitrogen atmosphere n-hexane as

溶剂反应制得,具体实验条件见实施例。 The reaction solvent is prepared, the specific experimental conditions see example.

[0007] [0007]

Figure CN102558238AD00051

[0008] [0008]

Figure CN102558238AD00061
Figure CN102558238AD00071

[0010] 本发明制备含有胍基团配体的铱配合物可用于制备有机电致发光器件,所述的有机电致发光器件由阴极、阳极和两极之间的一层或多层有机层构成,这些有机层中至少一层为发光层,发光层是由本发明制备的一种或几种含有胍基团配体的铱配合物构成。 [0010] The present invention was prepared containing iridium complex guanidino groups of the ligands may be used to prepare an organic electroluminescent device, the organic electroluminescent device is composed of one or more organic layers between the cathode, the anode and the bipolar , at least one of these layers constituting the organic light-emitting layer, light emitting layer is produced from a complex of the invention or an iridium-containing guanidino groups in several ligands thereof. 进一步的,这些有机层中至少一层为发光层,发光层是由本发明制备的一种或几种含有胍基团配体的铱配合物掺杂于主体材料(如CBP)中构成,在主体材料中含有胍基团配体的铱配合物的质量掺杂浓度为8%〜30%,所制备的器件都具有很高的器件性能和很好的稳定性。 Further, at least one of the organic layers is a light emitting layer, a light emitting layer containing an iridium complex of several guanidino group prepared from a ligand of the present invention or a host material to a dopant (such as CBP) constitutes, in the body mass iridium complex material containing guanidino groups of the ligands doping concentration of ~ 30%, 8%, are prepared devices having high device performance and good stability.

[0011] 进一步,所述的有机电致发光器件的结构如图1所示。 [0011] Further, the structure of the organic electroluminescent device shown in Figure 1. 器件结构依次包括:附着在透光玻璃上的ITO作为阳极、NPB(N,N' -二(ι-萘基)-N,N' - 二苯基-1,1'-联苯-4, 4' - 二胺)作为空穴传输层、本发明所述的铱配合物作为发光层或者以一定比例掺杂于CBP中作为发光层、TPBi (1,3,5-三(1-苯基-IH-苯并咪唑-2-基)苯)作为空穴阻挡层和电子传输层、LiF为电子注入层、金属Al作为阴极。 Device structure sequentially comprising: a light-transmissive glass deposited on the ITO as an anode, NPB (N, N '- two (iota-naphthyl) -N, N' - diphenyl-1,1'-biphenyl -4, 4 '- diamine) as a hole transporting layer, the iridium complex according to the present invention as a light emitting layer or in a certain ratio in the CBP doped with the light-emitting layer, TPBi (1,3,5- tris (1-phenyl -IH- benzimidazol-2-yl) benzene) as a hole blocking layer and electron transport layer, LiF electron injection layer, a metal Al as a cathode.

[0012] 本发明得到了发射光谱涵盖绿光到红光区域的高性能的电致发光器件,这些电致发光器件可用于平板显示器、照明光源、背光源、信号灯、字母数字显示器、指示牌、光电偶合器等应用领域。 [0012] The present invention encompasses obtained emission spectrum to the green electroluminescent device performance red region, which can be used in an electroluminescent flat panel display device, an illumination source, backlight, lamps, alphanumeric displays, signs, applications Optical coupling and so on.

附图说明 BRIEF DESCRIPTION

[0013] 图1 :应用本发明所述材料制备的的电致发光器件结构示意图。 [0013] FIG 1: a schematic view of an electrical structure of a light emitting device material prepared from the application of the present invention is induced.

[0014] 其中,附着在透光玻璃上的ITO作为阳极;各部件名称为:NPB(N,N' - 二(1_萘基)-N,N' - 二苯基-1,1'-联苯-4,4' - 二胺)为空穴传输层1 ;本发明所述的铱配合物作为发光层或者以一定比例掺杂于CBP中作为发光层2;TPBi(l,3,5-三(1-苯基-IH-苯并咪唑-2-基)苯)为空穴阻挡层和电子传输层3;LiF为电子注入材料4;金属Al为阴极5。 [0014] wherein, attached to the light-transmissive ITO glass as an anode; each member name: NPB (N, N '- bis (1_ naphthalenyl) -N, N' - diphenyl-1,1'- biphenyl-4,4 '- diamine) a hole transport layer; iridium complexes of the present invention as a light emitting layer or in a certain ratio in the CBP doped with the light-emitting layer 2; TPBi (l, 3,5 - tris (1-phenyl -IH- benzimidazol-2-yl) benzene) as a hole blocking layer and electron transport layer 3; LiF as the electron injection material 4; 5 metal Al cathode.

具体实施方式[0015] 实施例1 :化合物1的合成 DETAILED DESCRIPTION Embodiments [0015] Example 1: Synthesis of Compound 1

[0016] 50毫升圆底烧瓶中,-78°C,氮气保护下,将n-BuLi(0. 2mL χ 2. 5Μ)逐滴加入至二异丙胺(50mg,0.5mmol)的正己烷溶液(15mL)。 [0016] 50 ml round-bottomed flask, -78 ° C, under nitrogen atmosphere, n-BuLi (0. 2mL χ 2. 5Μ) was added dropwise to diisopropylamine (50mg, 0.5mmol) in n-hexane ( 15mL). 搅拌半个小时后,向混合液中滴加N, N' -二异丙基碳二亚胺(6;3mg,0. 5mmol)。 After stirring for half an hour, to the mixture was added dropwise N, N '- diisopropyl carbodiimide (6; 3mg, 0 5mmol.). 得到无色溶液再搅拌三十分钟后,滴加至Ll桥联铱配合物(0. 25mmOl,30;3mg)的正己烷溶液(20mL),滴加完升温至80°C,搅拌8小时。 After the resulting colorless solution was stirred for thirty minutes, added dropwise to Ll bridged iridium complex (0. 25mmOl, 30; 3mg) in n-hexane (20 mL), dropwise addition was warmed to 80 ° C, stirred for 8 hours. 反应液冷却至室温,溶剂减压蒸出,粗产品用乙醚(20mL)反复冲洗三次得到化合物K212mg)。 The reaction was cooled to room temperature, the solvent was distilled off under reduced pressure, the crude product with diethyl ether (20mL) to give compound repeatedly washed three times with K212mg). 质谱分析证明其分子量为798. 9 (C35H40F4IrN5) 0元素分析结果为:C,52. 57 ;H, 5. 08 ;N, Mass analysis showed a molecular weight of 798. 9 (C35H40F4IrN5) 0 Elementary analysis:. C, 52 57; H, 5. 08; N,

8. 54 (理论值为:C, 52. 62 ;H, 5. 05 ;N, 8. 77)。 8.54 (theoretical value: C, 52. 62; H, 5. 05; N, 8. 77).

[0017] 实施例2 :化合物2的合成 [0017] Example 2: Synthesis of Compound 2

[0018] 50毫升圆底烧瓶中,-78°C,氮气保护下,将n-BuLi(0. 2mL χ 2. 5Μ)逐滴加入至二异丙胺(50mg,0.5mmol)的正己烷溶液(15mL)。 [0018] 50 ml round-bottomed flask, -78 ° C, under nitrogen atmosphere, n-BuLi (0. 2mL χ 2. 5Μ) was added dropwise to diisopropylamine (50mg, 0.5mmol) in n-hexane ( 15mL). 搅拌半个小时后,向混合液中滴加N, N' -二异丙基碳二亚胺(6;3mg,0. 5mmol)。 After stirring for half an hour, to the mixture was added dropwise N, N '- diisopropyl carbodiimide (6; 3mg, 0 5mmol.). 得到无色溶液再搅拌三十分钟后,滴加至L2桥联铱配合物(0. 25mmoU67mg)的正己烷溶液(20mL),滴加完升温至80°C,搅拌8小时。 After the resulting colorless solution was stirred for thirty minutes, was added dropwise to L2 bridged iridium complex (0. 25mmoU67mg) in n-hexane (20 mL), dropwise addition was warmed to 80 ° C, stirred for 8 hours. 反应液冷却至室温,溶剂减压蒸出,粗产品用乙醚(20mL)反复冲洗三次得到化合物2(133mg). 质谱分析证明其分子量为726. 99 (C35H44IrN5) 0元素分析结果为:C,57.83 ;H, 5. 97 ;N, The reaction was cooled to room temperature, the solvent was distilled off under reduced pressure, the crude product with diethyl ether (20mL) to give compound repeatedly washed three times with 2 (133mg) Mass analysis showed a molecular weight of 726. 99 (C35H44IrN5) 0 Elementary analysis:. C, 57.83 ; H, 5. 97; N,

9. 65 (理论值为:C, 57. 83 ;H, 6. 10 ;N, 9. 63)。 9.65 (theoretical value: C, 57. 83; H, 6. 10; N, 9. 63).

[0019] 实施例3 :化合物3的合成 [0019] Example 3: Synthesis of Compound 3

[0020] 50毫升圆底烧瓶中,_78°C,氮气保护下,将n-BuL i (0. 2mL χ 2. 5Μ)逐滴加入至二异丙胺(50mg,0.5mmol)的正己烷溶液(15mL)。 [0020] 50 ml round-bottomed flask, _78 ° C, under nitrogen atmosphere, n-BuL i (0. 2mL χ 2. 5Μ) was added dropwise to diisopropylamine (50mg, 0.5mmol) in n-hexane ( 15mL). 搅拌半个小时后,向混合液中滴加N, N' -二异丙基碳二亚胺(6;3mg,0. 5mmol)。 After stirring for half an hour, to the mixture was added dropwise N, N '- diisopropyl carbodiimide (6; 3mg, 0 5mmol.). 得到无色溶液再搅拌三十分钟后,滴加至L3桥联铱配合物(0.25mmol,^ang)的正己烷溶液(20mL),滴加完升温至80°C,搅拌8小时。 After the resulting colorless solution was stirred for thirty minutes, was added dropwise to L3 bridged iridium complex (0.25mmol, ^ ang) in n-hexane (20 mL), dropwise addition was warmed to 80 ° C, stirred for 8 hours. 反应液冷却至室温,溶剂减压蒸出,粗产品用乙醚(20mL)反复冲洗三次得到化合物3(155mg). 质谱分析证明其分子量为774. 99 (C39H44IrN5)。 The reaction was cooled to room temperature, the solvent was distilled off under reduced pressure, the crude product with diethyl ether (20mL) to give repeatedly washed three times with compound 3 (155mg). Mass analysis showed a molecular weight of 774. 99 (C39H44IrN5). 元素分析结果为:C,60. 24 ;H, 5. 78 ;N, 8. 92 (理论值为=C, 60. 44 ;H, 5. 72 ;N, 9. 04)。 Elementary analysis: C, 60 24; H, 5. 78; N, 8. 92 (theoretical value = C, 60. 44; H, 5. 72; N, 9. 04)..

[0021 ] 实施例4 :化合物4的合成 [0021] Example 4: Synthesis of Compound 4

[0022] 50毫升圆底烧瓶中,-78°C,氮气保护下,将n-BuLi(0. 2mL χ 2. 5Μ)逐滴加入至二异丙胺(50mg,0.5mmol)的正己烷溶液(15mL)。 [0022] 50 ml round-bottomed flask, -78 ° C, under nitrogen atmosphere, n-BuLi (0. 2mL χ 2. 5Μ) was added dropwise to diisopropylamine (50mg, 0.5mmol) in n-hexane ( 15mL). 搅拌半个小时后,向混合液中滴加N, N' -二异丙基碳二亚胺(6;3mg,0. 5mmol)。 After stirring for half an hour, to the mixture was added dropwise N, N '- diisopropyl carbodiimide (6; 3mg, 0 5mmol.). 得到无色溶液再搅拌三十分钟后,滴加至L4桥联铱配合物(0. 25mmol,324mg)的正己烷溶液(20mL),滴加完升温至80°C,搅拌8小时。 After the resulting colorless solution was stirred for thirty minutes, was added dropwise to L4 bridged iridium complex (0. 25mmol, 324mg) in n-hexane (20 mL), dropwise addition was warmed to 80 ° C, stirred for 8 hours. 反应液冷却至室温,溶剂减压蒸出,粗产品用乙醚(20mL)反复冲洗三次得到化合物M270mg)。 The reaction was cooled to room temperature, the solvent was distilled off under reduced pressure, the crude product with diethyl ether (20mL) to give compound repeatedly washed three times with M270mg). 质谱分析证明其分子量为838. 82 (C39H44IrRS2)。 Mass analysis showed a molecular weight of 838. 82 (C39H44IrRS2). 元素分析结果为:C,55. 71 ;H, 5. 33 ;N, 8. 20 (理论值为:C, 55. 82 ;H, 5. 29 ;N, 8. 35)。 Elementary analysis: C, 55 71; H, 5. 33; N, 8. 20. (Theoretical value: C, 55. 82; H, 5. 29; N, 8. 35).

[0023] 实施例5 :化合物5的合成 [0023] Example 5: Synthesis of Compound 5

[0024] 50毫升圆底烧瓶中,-78°C,氮气保护下,将n-BuLi(0. 2mL χ 2. 5Μ)逐滴加入至二异丙胺(50mg,0.5mmol)的正己烷溶液(15mL)。 [0024] 50 ml round-bottomed flask, -78 ° C, under nitrogen atmosphere, n-BuLi (0. 2mL χ 2. 5Μ) was added dropwise to diisopropylamine (50mg, 0.5mmol) in n-hexane ( 15mL). 搅拌半个小时后,向混合液中滴加N, N' -二异丙基碳二亚胺(6;3mg,0. 5mmol)。 After stirring for half an hour, to the mixture was added dropwise N, N '- diisopropyl carbodiimide (6; 3mg, 0 5mmol.). 得到无色溶液再搅拌三十分钟后,滴加至L5桥联铱配合物(0. 25mmol,274mg)的正己烷溶液(20mL),滴加完升温至80°C,搅拌8小时。 After the resulting colorless solution was stirred for thirty minutes, added dropwise to L5 bridged iridium complex (0. 25mmol, 274mg) in n-hexane (20 mL), dropwise addition was warmed to 80 ° C, stirred for 8 hours. 反应液冷却至室温,溶剂减压蒸出,粗产品用乙醚(20mL)反复冲洗三次得到化合物5(166mg)。 The reaction was cooled to room temperature, the solvent was distilled off under reduced pressure, the crude product with diethyl ether (20mL) to give repeatedly washed three times with compound 5 (166mg). 质谱分析证明其分子量为739. H(C31H40IrN5S2)o元素分析结果为:C,50. 21 ;H, 5. 33 ;N,9. 50 (理论值为:C, 50. 38 ;H, 5. 46 ;N, 9. 48)。 Mass analysis showed a molecular weight of 739. H (C31H40IrN5S2) o Elementary analysis as:. C, 50 21; H, 5. 33; N, 9 50 (theoretical value:. C, 50. 38; H, 5. 46; N, 9. 48).

[0025] 实施例6 :化合物6的合成 [0025] Example 6: Synthesis of Compound 6

[0026] 50毫升圆底烧瓶中,-78°C,氮气保护下,将n-BuLi(0. 2mL χ 2. 5Μ)逐滴加入至二异丙胺(50mg,0.5mmol)的正己烷溶液(15mL)。 [0026] 50 ml round-bottomed flask, -78 ° C, under nitrogen atmosphere, n-BuLi (0. 2mL χ 2. 5Μ) was added dropwise to diisopropylamine (50mg, 0.5mmol) in n-hexane ( 15mL). 搅拌半个小时后,向混合液中滴加N, N' -二异丙基碳二亚胺(6;3mg,0. 5mmol)。 After stirring for half an hour, to the mixture was added dropwise N, N '- diisopropyl carbodiimide (6; 3mg, 0 5mmol.). 得到无色溶液再搅拌三十分钟后,滴加至L6桥联铱配合物(0. 25mmol,258mg)的正己烷溶液(20mL),滴加完升温至80°C,搅拌8小时。 After the resulting colorless solution was stirred for thirty minutes, added dropwise to L6 bridged iridium complex (0. 25mmol, 258mg) in n-hexane (20 mL), dropwise addition was warmed to 80 ° C, stirred for 8 hours. 反应液冷却至室温,溶剂减压蒸出,粗产品用乙醚(20mL)反复冲洗三次得到化合物6(159mg)。 The reaction was cooled to room temperature, the solvent was distilled off under reduced pressure, the crude product with diethyl ether (20mL) to give repeatedly washed three times with compound 6 (159mg). 质谱分析证明其分子量为706. 98 (C31H40IrN5O2) 0元素分析结果为:C,52. 53 ;H, 5. 62 ;N, 9. 88 (理论值为:C, 52. 67 ;H, 5. 70 ;N, 9. 91)。 Mass analysis showed a molecular weight of 706. 98 (C31H40IrN5O2) 0 Elementary analysis:. C, 52 53; H, 5. 62; N, 9. 88 (theoretical value: C, 52. 67; H, 5. 70; N, 9. 91).

[0027] 实施例7 :化合物7的合成 [0027] Example 7: Synthesis of Compound 7

[0028] 50毫升圆底烧瓶中,-78°C,氮气保护下,将n-BuLi(0. 2mL χ 2. 5Μ)逐滴加入至二异丙胺(50mg,0.5mmol)的正己烷溶液(15mL)。 [0028] 50 ml round-bottomed flask, -78 ° C, under nitrogen atmosphere, n-BuLi (0. 2mL χ 2. 5Μ) was added dropwise to diisopropylamine (50mg, 0.5mmol) in n-hexane ( 15mL). 搅拌半个小时后,向混合液中滴加N, N' -二异丙基碳二亚胺(6;3mg,0. 5mmol)。 After stirring for half an hour, to the mixture was added dropwise N, N '- diisopropyl carbodiimide (6; 3mg, 0 5mmol.). 得到无色溶液再搅拌三十分钟后,滴加至L7桥联铱配合物(0. 25mmol,318mg)的正己烷溶液(20mL),滴加完升温至80°C,搅拌8小时。 After the resulting colorless solution was stirred for thirty minutes, added dropwise to L7 bridged iridium complex (0. 25mmol, 318mg) in n-hexane (20 mL), dropwise addition was warmed to 80 ° C, stirred for 8 hours. 反应液冷却至室温,溶剂减压蒸出,粗产品用乙醚(20mL)反复冲洗三次得到化合物U207mg)。 The reaction was cooled to room temperature, the solvent was distilled off under reduced pressure, the crude product with diethyl ether (20mL) to give compound repeatedly washed three times with U207mg). 质谱分析证明其分子量为827. 20 (C43H48IrN5)。 Mass analysis showed a molecular weight of 827. 20 (C43H48IrN5). 元素分析结果为:C,62. 21 ;H, 5. 72 ;N, Elementary analysis: C, 62 21; H, 5. 72; N,.

8. 45 (理论值为=C, 62. 44 ;H, 5. 85 ;N, 8. 47)。 8.45 (theoretical = C, 62. 44; H, 5. 85; N, 8. 47).

[0029] 实施例8 :化合物8的合成 [0029] Example 8: Synthesis of Compound 8

[0030] 50毫升圆底烧瓶中,-78°C,氮气保护下,将n-BuLi(0. 2mL χ 2. 5Μ)逐滴加入至二异丙胺(50mg,0.5mmol)的正己烷溶液(15mL)。 [0030] 50 ml round-bottomed flask, -78 ° C, under nitrogen atmosphere, n-BuLi (0. 2mL χ 2. 5Μ) was added dropwise to diisopropylamine (50mg, 0.5mmol) in n-hexane ( 15mL). 搅拌半个小时后,向混合液中滴加N, N' -二异丙基碳二亚胺(6;3mg,0. 5mmol)。 After stirring for half an hour, to the mixture was added dropwise N, N '- diisopropyl carbodiimide (6; 3mg, 0 5mmol.). 得到无色溶液再搅拌三十分钟后,滴加至L8桥联铱配合物(0.25mmol,^ang)的正己烷溶液(20mL),滴加完升温至80°C,搅拌8小时。 After the resulting colorless solution was stirred for thirty minutes, added dropwise to L8 bridged iridium complex (0.25mmol, ^ ang) in n-hexane (20 mL), dropwise addition was warmed to 80 ° C, stirred for 8 hours. 反应液冷却至室温,溶剂减压蒸出,粗产品用乙醚(20mL)反复冲洗三次得到化合物W2^5mg)。 The reaction was cooled to room temperature, the solvent was distilled off under reduced pressure, the crude product with diethyl ether (20mL) to give ^ 5mg repeatedly washed three times with compound W2). 质谱分析证明其分子量为755. 29 (C37H48IrN5)。 Mass analysis showed a molecular weight of 755. 29 (C37H48IrN5). 元素分析结果为:C,58. 75 ;H, 6. 37 ;N, Elementary analysis: C, 58 75; H, 6. 37; N,.

9. 19 (理论值为:C, 58. 86 ;H, 6. 41 ;N, 9. 28)。 9.19 (theoretical value: C, 58. 86; H, 6. 41; N, 9. 28). [0031 ] 实施例9 :化合物9的合成 [0031] Example 9: Synthesis of Compound 9

[0032] 50毫升圆底烧瓶中,-78°C,氮气保护下,将n-BuLi(0. 2mL χ 2. 5Μ)逐滴加入至二异丙胺(50mg,0.5mmol)的正己烷溶液(15mL)。 [0032] 50 ml round-bottomed flask, -78 ° C, under nitrogen atmosphere, n-BuLi (0. 2mL χ 2. 5Μ) was added dropwise to diisopropylamine (50mg, 0.5mmol) in n-hexane ( 15mL). 搅拌半个小时后,向混合液中滴加N, N' -二异丙基碳二亚胺(6;3mg,0. 5mmol)。 After stirring for half an hour, to the mixture was added dropwise N, N '- diisopropyl carbodiimide (6; 3mg, 0 5mmol.). 得到无色溶液再搅拌三十分钟后,滴加至L9桥联铱配合物(0. 25mmol,305mg)的正己烷溶液(20mL),滴加完升温至80°C,搅拌8小时。 After the resulting colorless solution was stirred for thirty minutes, added dropwise to L9 bridged iridium complex (0. 25mmol, 305mg) in n-hexane (20 mL), dropwise addition was warmed to 80 ° C, stirred for 8 hours. 反应液冷却至室温,溶剂减压蒸出,粗产品用乙醚(20mL)反复冲洗三次得到化合物9(160mg)。 The reaction was cooled to room temperature, the solvent was distilled off under reduced pressure, the crude product with diethyl ether (20mL) to give repeatedly washed three times with compound 9 (160mg). 质谱分析证明其分子量为800. 98 (C33H38F4IrN7)。 Mass analysis showed a molecular weight of 800. 98 (C33H38F4IrN7). 元素分析结果为=C, 49. 70 ;H, 4. 67 ;N, 12. 21 (理论值为=C, 49. 49 ;H, 4. 78 ;N, 12. 24)。 Elementary analysis as = C, 49. 70; H, 4. 67; N, 12. 21 (theoretical value = C, 49. 49; H, 4. 78; N, 12. 24).

[0033] 实施例10 :化合物10的合成 [0033] Example 10: Synthesis of Compound 10

[0034] 50毫升圆底烧瓶中,-78°C,氮气保护下,将n-BuLi(0. 2mL χ 2. 5Μ)逐滴加入至二异丙胺(50mg,0.5mmol)的正己烷溶液(15mL)。 [0034] 50 ml round-bottomed flask, -78 ° C, under nitrogen atmosphere, n-BuLi (0. 2mL χ 2. 5Μ) was added dropwise to diisopropylamine (50mg, 0.5mmol) in n-hexane ( 15mL). 搅拌半个小时后,向混合液中滴加N, N' -二异丙基碳二亚胺(6;3mg,0.5mmOl)。 After stirring for half an hour, to the mixture was added dropwise N, N '- diisopropyl carbodiimide (6; 3mg, 0.5mmOl). 得到无色溶液再搅拌三十分钟后,滴加至LlO 桥联铱配合物(0. 25mmol,318mg)的正己烷溶液(20mL),滴加完升温至80°C,搅拌8小时。 After the resulting colorless solution was stirred for thirty minutes, added dropwise to LlO bridged iridium complex (0. 25mmol, 318mg) in n-hexane (20 mL), dropwise addition was warmed to 80 ° C, stirred for 8 hours. 反应液冷却至室温,溶剂减压蒸出,粗产品用乙醚(20mL)反复冲洗三次得到化合物10(145mg)。 The reaction was cooled to room temperature, the solvent was distilled off under reduced pressure, the crude product with diethyl ether (20mL) to give repeatedly washed three times with compound 10 (145mg). 质谱分析证明其分子量为827. 12 (C43H48IrN5)。 Mass analysis showed a molecular weight of 827. 12 (C43H48IrN5). 元素分析结果为=C, 62. 27 ;H, 5. 84 ;N, 8. 34 (理论值为:C,62. 44 ;H, 5. 85 ;N, 8. 47)。 Elementary analysis as = C, 62. 27; H, 5. 84; N, 8. 34 (theoretical value: C, 62 44; H, 5. 85; N, 8. 47.).

[0035] 实施例11 :化合物11的合成 Synthesis of Compound 11: Example 11 [0035] Embodiment

[0036] 50毫升圆底烧瓶中,-78°C,氮气保护下,将n-BuLi(0. 2mL χ 2. 5Μ)逐滴加入至二异丙胺(50mg,0.5mmol)的正己烷溶液(15mL)。 [0036] 50 ml round-bottomed flask, -78 ° C, under nitrogen atmosphere, n-BuLi (0. 2mL χ 2. 5Μ) was added dropwise to diisopropylamine (50mg, 0.5mmol) in n-hexane ( 15mL). 搅拌半个小时后,向混合液中滴加N, N' -二异丙基碳二亚胺(6;3mg,0.5mmOl)。 After stirring for half an hour, to the mixture was added dropwise N, N '- diisopropyl carbodiimide (6; 3mg, 0.5mmOl). 得到无色溶液再搅拌三十分钟后,滴加至Lll 桥联铱配合物(0. 25mm0l,37^ig)的正己烷溶液(20mL),滴加完升温至80°C,搅拌8小时。 After the resulting colorless solution was stirred for thirty minutes, added dropwise to Lll bridged iridium complex (0. 25mm0l, 37 ^ ig) in n-hexane (20 mL), dropwise addition was warmed to 80 ° C, stirred for 8 hours. 反应液冷却至室温,溶剂减压蒸出,粗产品用乙醚(20mL)反复冲洗三次得到化合物11 (141mg)。 The reaction was cooled to room temperature, the solvent was distilled off under reduced pressure, the crude product with diethyl ether (20mL) to give repeatedly washed three times with compound 11 (141mg). 质谱分析证明其分子量为938. 98 (C47H48IrN5S2)。 Mass analysis showed a molecular weight of 938. 98 (C47H48IrN5S2). 元素分析结果为=C, 60. 01 ;H, 5. 20 ;N, 7. 37 (理论值为:C, 60. 10 ;H, 5. 15 ;N, 7. 46)。 Elementary analysis as = C, 60. 01; H, 5. 20; N, 7. 37 (theoretical value: C, 60. 10; H, 5. 15; N, 7. 46).

[0037] 实施例12 :化合物12的合成 [0037] Example 12: Synthesis of Compound 12

[0038] 50毫升圆底烧瓶中,-78°C,氮气保护下,将n-BuLi(0. 2mL χ 2. 5Μ)逐滴加入至二异丙胺(50mg,0.5mmol)的正己烷溶液(15mL)。 [0038] 50 ml round-bottomed flask, -78 ° C, under nitrogen atmosphere, n-BuLi (0. 2mL χ 2. 5Μ) was added dropwise to diisopropylamine (50mg, 0.5mmol) in n-hexane ( 15mL). 搅拌半个小时后,向混合液中滴加N, N' -二异丙基碳二亚胺(6;3mg,0.5mmOl)。 After stirring for half an hour, to the mixture was added dropwise N, N '- diisopropyl carbodiimide (6; 3mg, 0.5mmOl). 得到无色溶液再搅拌三十分钟后,滴加至L12 桥联铱配合物(0. 25mm0l,32^ig)的正己烷溶液(20mL),滴加完升温至80°C,搅拌8小时。 After the resulting colorless solution was stirred for thirty minutes, was added dropwise to L12 bridged iridium complex (0. 25mm0l, 32 ^ ig) in n-hexane (20 mL), dropwise addition was warmed to 80 ° C, stirred for 8 hours. 反应液冷却至室温,溶剂减压蒸出,粗产品用乙醚(20mL)反复冲洗三次得到化合物12(168mg)。 The reaction was cooled to room temperature, the solvent was distilled off under reduced pressure, the crude product with diethyl ether (20mL) to give repeatedly washed three times with compound 12 (168mg). 质谱分析证明其分子量为839. 18 (C39H44IrN5S2)。 Mass analysis showed a molecular weight of 839. 18 (C39H44IrN5S2). 元素分析结果为=C, 55. 79 ;H, 5. 23 ;N, 8. 28 (理论值为:C,55. 82 ;H, 5. 29 ;N, 8. 35)。 Elementary analysis as = C, 55. 79; H, 5. 23; N, 8. 28 (theoretical value:. C, 55 82; H, 5. 29; N, 8. 35).

[0039] 实施例13 :化合物13的合成 [0039] Example 13: Synthesis of Compound 13

[0040] 50毫升圆底烧瓶中,-78°C,氮气保护下,将n-BuLi(0. 2mL χ 2. 5Μ)逐滴加入至二异丙胺(50mg,0.5mmol)的正己烷溶液(15mL)。 [0040] 50 ml round-bottomed flask, -78 ° C, under nitrogen atmosphere, n-BuLi (0. 2mL χ 2. 5Μ) was added dropwise to diisopropylamine (50mg, 0.5mmol) in n-hexane ( 15mL). 搅拌半个小时后,向混合液中滴加N, N' -二异丙基碳二亚胺(6;3mg,0.5mmOl)。 After stirring for half an hour, to the mixture was added dropwise N, N '- diisopropyl carbodiimide (6; 3mg, 0.5mmOl). 得到无色溶液再搅拌三十分钟后,滴加至L13 桥联铱配合物(0. 25mmol,308mg)的正己烷溶液(20mL),滴加完升温至80°C,搅拌8小时。 After the resulting colorless solution was stirred for thirty minutes, added dropwise to L13 bridged iridium complex (0. 25mmol, 308mg) in n-hexane (20 mL), dropwise addition was warmed to 80 ° C, stirred for 8 hours. 反应液冷却至室温,溶剂减压蒸出,粗产品用乙醚(20mL)反复冲洗三次得到化合物13(161mg)。 The reaction was cooled to room temperature, the solvent was distilled off under reduced pressure, the crude product with diethyl ether (20mL) to give repeatedly washed three times with compound 13 (161mg). 质谱分析证明其分子量为807. 25 (C39H44IrN5O2)。 Mass analysis showed a molecular weight of 807. 25 (C39H44IrN5O2). 元素分析结果为=C, 57. 95 ;H, 5. 42 ;N, 8. 54 (理论值为:C,58. 04 ;H, 5. 50 ;N, 8. 68)。 Elementary analysis as = C, 57. 95; H, 5. 42; N, 8. 54 (theoretical value: C, 58 04; H, 5. 50; N, 8. 68.).

[0041] 实施例14 :化合物14的合成 [0041] Example 14: Synthesis of Compound 14

[0042] 50毫升圆底烧瓶中,-78°C,氮气保护下,将n-BuLi(0. 2mL χ 2. 5Μ)逐滴加入至二异丙胺(50mg,0.5mmol)的正己烷溶液(15mL)。 [0042] 50 ml round-bottomed flask, -78 ° C, under nitrogen atmosphere, n-BuLi (0. 2mL χ 2. 5Μ) was added dropwise to diisopropylamine (50mg, 0.5mmol) in n-hexane ( 15mL). 搅拌半个小时后,向混合液中滴加N, N' -二异丙基碳二亚胺(6;3mg,0.5mmOl)。 After stirring for half an hour, to the mixture was added dropwise N, N '- diisopropyl carbodiimide (6; 3mg, 0.5mmOl). 得到无色溶液再搅拌三十分钟后,滴加至L14 桥联铱配合物(0. 25mmol,358mg)的正己烷溶液(20mL),滴加完升温至80°C,搅拌8小时。 After the resulting colorless solution was stirred for thirty minutes, added dropwise to L14 bridged iridium complex (0. 25mmol, 358mg) in n-hexane (20 mL), dropwise addition was warmed to 80 ° C, stirred for 8 hours. 反应液冷却至室温,溶剂减压蒸出,粗产品用乙醚(20mL)反复冲洗三次得到化合物14(158mg)。 The reaction was cooled to room temperature, the solvent was distilled off under reduced pressure, the crude product with diethyl ether (20mL) to give repeatedly washed three times with compound 14 (158mg). 质谱分析证明其分子量为907. 25 (C47H48IrN5O2)。 Mass analysis showed a molecular weight of 907. 25 (C47H48IrN5O2). 元素分析结果为=C, 62. 18 ;H, 5. 30 ;N, 7. 65 (C, 62. 23 ;H, 5. 33 ;N, 7. 72)。 Elementary analysis as = C, 62. 18; H, 5. 30; N, 7. 65 (C, 62. 23; H, 5. 33; N, 7. 72).

[0043]实施例 15 :发光器件[IT0/NPB/CBP : 15%化合物1/TPBi/LiF/Al] [0043] Example 15: light-emitting device [IT0 / NPB / CBP: 15% Compound 1 / TPBi / LiF / Al]

[0044] 在镀有ITO(铟锡氧化物)阳极的玻璃基片上依次蒸镀空穴传输层NPB(厚度为400 A),发光层实施例1制备的化合物1以15%质量浓度掺杂于CBP中(300 A),空穴阻挡及电子传输层TPBi (300 A),电子注入材料LiF (5 A),A1阴极(2000 A)。 [0044] In the compounds plated with ITO (indium tin oxide) were deposited in a hole transport layer NPB (thickness 400 A) of the glass substrate on the anode, the light emitting layer prepared in Example 1 of the embodiment 1 to 15% by mass concentration doped in the CBP (300 A), a hole blocking layer and electron transport TPBi (300 A), the electron injecting material LiF (5 A), A1 cathode (2000 A). 在蒸镀过程中保持压力为5 X KT4Pa以下。 Maintaining the pressure in the evaporation process is less 5 X KT4Pa. 该器件发射峰位为532nm (绿光),开启电压3V,最大电流效率为64. 2cd/A,最大功率效率为611m/W。 The peak emission device is 532nm (green), turn-on voltage 3V, the maximum current efficiency was 64. 2cd / A, the maximum power efficiency of 611m / W.

[0045]实施例 16 :发光器件[IT0/NPB/CBP 化合物2/TPBi/LiF/Al] [0045] Example 16: light-emitting device [IT0 / NPB / CBP Compound 2 / TPBi / LiF / Al]

[0046] 在镀有ITO阳极的玻璃基片上依次蒸镀空穴传输层NPB(厚度为400 A ),发光层实施例2制备的化合物2以8%质量浓度掺杂于CBP中(300 A),空穴阻挡及电子传输层1?81(300八),电子注入材料1^?(5八),八1阴极(2000 A)。 [0046] The hole transport layer are sequentially deposited NPB (thickness 400 A) on a glass substrate coated with an ITO anode, light emitting layer in Example 2 compound prepared in a concentration of 2 to 8% by mass in the CBP doped (300 A) , a hole blocking layer and electron transport 1? 81 (300%), the electron injecting material 1 ^? (5 h), eight cathode (2000 A). 在蒸镀过程中保持压力为5 X IO^4Pa以下。 Keep the pressure in the evaporation process is 5 X IO ^ 4Pa less. 该器件发射峰位为556nm (黄光),开启电压3V,最大电流效率为63. Icd/ A,最大功率效率为63. 61m/W。 The peak emission device was 556 nm (yellow light), the threshold voltage 3V, the maximum current efficiency was 63. Icd / A, the maximum power efficiency was 63. 61m / W.

[0047]实施例 17 :发光器件[IT0/NPB/CBP : 15%化合物3/TPBi/LiF/Al] [0047] Example 17: light-emitting device [IT0 / NPB / CBP: 15% Compound 3 / TPBi / LiF / Al]

[0048] 在镀有ITO阳极的玻璃基片上依次蒸镀空穴传输层NPB(厚度为400 A ),发光层实施例1制备的化合物3以15%质量浓度掺杂于CBP中(300 A),空穴阻挡及电子传输层TPBi (300 A),电子注入材料LiF (5 A),Al阴极(2000 A)。 [0048] The hole transport layer are sequentially deposited NPB (thickness 400 A) on a glass substrate having an ITO anode plating, the compound prepared in Example 1 embodiment the light emitting layer 3 is doped in a concentration of 15% by mass of CBP (300 A) , a hole blocking layer and electron transport TPBi (300 A), the electron injecting material LiF (5 A), Al cathode (2000 A). 在蒸镀过程中保持压力为5X 10_4Pa以下。 The pressure was kept 5X 10_4Pa in less evaporation process. 该器件发射峰位为588nm(橙红光),开启电压2. 6V,最大电流效率为29. lcd/A,最大功率效率为25. 41m/W。 The device for the emission peak of 588 nm (orange light), the threshold voltage 2. 6V, the maximum current efficiency was 29. lcd / A, the maximum power efficiency was 25. 41m / W.

[0049]实施例 18 :发光器件[IT0/NPB/CBP 化合物4/TPBi/LiF/Al] [0049] Example 18: light-emitting device [IT0 / NPB / CBP Compound 4 / TPBi / LiF / Al]

[0050] 在镀有ITO阳极的玻璃基片上依次蒸镀空穴传输层NPB(厚度为400 A),发光层实施例1制备的化合物4以8%质量浓度掺杂于CBP中(300 A),空穴阻挡及电子传输层1?81(300八),电子注入材料1^?(5八),八1阴极(2000 A)。 [0050] The hole transport layer are sequentially deposited NPB (thickness 400 A) on a glass substrate having an ITO anode plating, the compound prepared in Example 1 embodiment the light emitting layer 4 doped with a concentration of 8% by mass in the CBP (300 A) , a hole blocking layer and electron transport 1? 81 (300%), the electron injecting material 1 ^? (5 h), eight cathode (2000 A). 在蒸镀过程中保持压力为5X 10_4Pa以下。 The pressure was kept 5X 10_4Pa in less evaporation process. 该器件发射峰位为624nm (红光),开启电压3. 2V,最大电流效率为7. Scd/ A,最大功率效率为5. 61m/W。 The peak emission device of 624nm (red light), the threshold voltage 3. 2V, the maximum current efficiency was 7. Scd / A, the maximum power efficiency of 5. 61m / W.

Claims (6)

1. ー类含有胍基团配体的铱配合物,其结构式如下所示: 1. ー class containing iridium complex ligands guanidino group, the structural formula is shown below:
Figure CN102558238AC00021
Figure CN102558238AC00031
2.权利要求1所述的含有胍基团配体的铱配合物在制备有机电致发光器件方面的应用。 Iridium-containing guanidine groups of the ligands according to claim 1 for the preparation of complex organic electroluminescent devices have application aspects.
3.如权利要求2所述的含有胍基团配体的铱配合物在制备有机电致发光器件方面的应用,其特征在于:有机电致发光器件由阴极、阳极和两极之间的一层或多层有机层构成, 这些有机层中至少一层为发光层,且是由权利要求1所述的一种或几种含有胍基团配体的铱配合物构成。 Iridium complexes containing ligands guanidino group as claimed in claim 2 in the preparation of organic electroluminescent devices have application aspects of emission, wherein: the organic electroluminescent device a layer between the cathode, anode and poles the organic layer or a plurality of layers, at least one of the organic layers is a light emitting layer, and is one of the claims 1 or more guanidino group-containing iridium complex ligands configuration.
4.如权利要求2所述的含有胍基团配体的铱配合物在制备有机电致发光器件方面的应用,其特征在于:有机电致发光器件由阴极、阳极和两极之间的一层或多层有机层构成, 这些有机层中至少一层为发光层,且是由权利要求1所述的一种或几种含有胍基团配体的铱配合物掺杂于主体材料中构成。 Iridium complexes containing ligands guanidino group as claimed in claim 2 in the preparation of organic electroluminescent devices have application aspects of emission, wherein: the organic electroluminescent device a layer between the cathode, anode and poles the organic layer or a plurality of layers, at least one of the organic layers is a light emitting layer, and is one of the claims 1 or more guanidino group-containing ligands in the iridium complex dopant material constituting the body.
5.如权利要求4所述的含有胍基团配体的铱配合物在制备有机电致发光器件方面的应用,其特征在于:在主体材料中,含有胍基团配体的铱配合物的质量掺杂浓度为8%〜 30%。 As claimed in claim 4 containing iridium complex guanidino groups of the ligands have application in the manufacture of organic electroluminescent light emitting device aspect, wherein: the host material, an iridium containing guanidino groups of the ligands of the complexes mass doping concentration of 8% to 30%.
6.如权利要求2〜5任何一项所述的含有胍基团配体的铱配合物在制备有机电致发光器件方面的应用,其特征在于:用于平板显示或照明光源。 6. 2 ~ 5 any iridium containing guanidino groups of the ligands of a complex according to claim in the manufacture of an organic electroluminescent device has application aspect, wherein: a flat panel display or lighting.
CN2011103996612A 2011-12-06 2011-12-06 Iridium complexes containing guanidine group and application of iridium complexes to preparation of electroluminescent devices CN102558238A (en)

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