CN1726606A - 有机发光材料和器件 - Google Patents
有机发光材料和器件 Download PDFInfo
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- CN1726606A CN1726606A CNA2003801061055A CN200380106105A CN1726606A CN 1726606 A CN1726606 A CN 1726606A CN A2003801061055 A CNA2003801061055 A CN A2003801061055A CN 200380106105 A CN200380106105 A CN 200380106105A CN 1726606 A CN1726606 A CN 1726606A
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- 229910052751 metal Inorganic materials 0.000 claims abstract description 33
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 9
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical group CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 claims description 27
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- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
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- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Abstract
提供了一种有机发光器件。该器件包括阳极、阴极和放置在阳极和阴极之间的发射层。该发射层包括具有结构(I)的材料，M为原子量大于40的金属，m至少为1，n至少为0，R″为H或任意的取代基，X为辅助配体，且A选自芳环或杂芳环，和B为芳环。还提供了包括上述材料的光敏配体的材料。
Description
发明领域
本发明涉及有机发光器件(OLED)，更具体地说涉及在该器件中使用的有机材料。
背景技术
出于许多原因，使用有机材料的光-电子器件越来越合乎人们的需要。用于制造该器件的许多材料都比较廉价，因此有机光-电子器件比无机器件更具有潜在的价格优势。此外，有机材料的内在性质，例如柔性，可使其非常适用于某些特殊应用，例如适于在柔性基底上进行制造。有机光-电子器件的例子包括有机发光器件(OLED)、有机光敏晶体管、有机光电池和有机光检测器。对于OLED而言，有机材料可能比常规材料具有性能优越性。例如，通常可借助适当的掺杂剂容易地调整有机发射层的发光波长。
本文中所用的术语“有机”包括可用于制造有机光-电子器件的聚合材料和小分子有机材料。“小分子”指非聚合物的任何有机材料，而且“小分子”实际上也可能非常大。某些情况下小分子可包括重复单元。例如，使用长链烷基作为取代基的分子也不排除在“小分子”类之外。小分子还可结合在聚合物中，例如作为聚合物主链上的连接基团，或作为主链的一部分。小分子还可作为枝状体(dendrimer)的核心部分，其由一系列构架在核心部分上的化学外壳组成。枝状体的核心部分可为小分子的荧光或磷光发射体。
OLED使用有机薄膜，向器件施加电压时该有机薄膜能发光。在诸如平板显示器、照明和逆光应用中，OLED技术越来越引起人们的兴趣。美国专利No.5,844,363、No.6,303,238和No.5,707,745中公开了若干种OLED材料和构造，其全部内容引入本文作为参考。
OLED器件通常(但不总是)是要透过至少一个电极发光，因此可将一个或多个透明电极用于有机光-电子器件中。例如，可将诸如铟锡氧化物(ITO)的透明电极材料用作底电极。可使用，例如美国专利No.5,703,436和No.5,707,745中公开的透明顶电极，该专利的全部内容引入本文作为参考。对于只意图透过底电极进行发光的器件，顶电极不需要为透明的，其可由具有高电导率的厚反射金属层组成。类似地，对于只意图透过顶电极进行发光的器件，底电极可为不透明和/或反射性的。当电极不需要为透明时，使用较厚的层可提供更好的导电性，使用反射性电极，由于其将光反射回透明电极，因此可提高透过另一个电极的发射光。还可制造完全透明的器件，此时两个电极都为透明的。还可制造侧面发光的OLED，这种器件中，一个或两个电极可为不透明或反射性的。
本文中所用的“顶”指离基底最远，而“底”指离基底最近。例如，对于具有两个电极的器件，底电极为最接近基底的电极，其通常是制造出来的第一个电极。底电极具有两个表面，底表面与基底最接近，顶表面远离基底。若将第一层描述为“放置在第二层之上”，则第一层远离基底放置。除非特别指出第一层与第二层为“物理接触”，否则在第一和第二层之间还可有其它层。例如，阴极可被描述为“放置在阳极之上”，即使在二者之间还有各种有机层。
磷光发射材料的一个应用是全色显示器。这种显示器的工业标准要求像素适于发射特定的颜色，称作“饱和”色。尤其，这些标准要求饱和的红色、绿色和蓝色像素。可使用CIE坐标测定颜色，其为本领域公知技术。CIE坐标在H.Zollinger，“Color Chemistry”VCHPublishers，1991和H.J.A.Dartnall、J.K.Bowmaker和J.D.Mollon，Proc.Roy.Soc.B(London)，1983，220，115-130中有所描述，其引入本文作为参考。
磷光发射材料的另一个应用是全色显示器，或另外的、意图用电池驱动的显示器，例如移动电话显示器或数字摄像机。对于这种应用，功率系数是特别重要的参数，因为有效发光可显著延长电池寿命，和/或可以使用更小的电池。照明设备是另一个应用，该应用中功率系数也特别重要，这是由于用于照明应用的纯功率容量。对于许多其它应用，功率系数也很重要。而且，由于效率低的器件通常将功率浪费在发热而非发光上，且热还可以给器件寿命带来负面影响，因此高功率系数可导致更长的寿命。
发明概述
提供了一种有机发光器件。该器件包括阳极、阴极和放置在阳极和阴极之间的发射层。发射层包括具有下式结构的材料：
M为原子量大于40的金属，m至少为1，n至少为0，R″为H或任意的取代基，X为辅助配体，A选自芳环和杂芳环，且B为芳环。还提供了包括上述材料的光敏(photoactive)配体的材料。
附图简述
图1显示了具有分离的电子传递层、空穴传递层和发射层以及其它层的有机发光器件。
图2显示了不具有分离的电子传递层的反相(inverted)有机发光器件。
图3显示了不同器件的发光效率-亮度曲线图。
图4显示了不同器件的外量子效率-亮度曲线图。
发明详述
通常，OLED包括至少一个放置在阳极和阴极之间且与阳极和阴极电连接的有机层。当施加电流时，阳极将空穴注入到有机层中，并且阴极将电子注入到有机层中。注入的空穴和电子各自向相反电荷的电极迁移。当电子和空穴定位在同一个分子上时，则形成了“激子”，其为具有激发能量态的定域电子-空穴对。当激子通过光电发射机理衰减时则发光。一些情况下，激子可定域在受激准分子(excimer)或激态复合物(exciplex)上。也可能出现非发射性机理，例如热弛豫现象，但通常认为其是不希望的。
例如，美国专利No.4,769,292中所公开的，最初的OLED使用从单重态(“荧光”)发光的发射分子，该专利的全部内容引入本文作为参考。荧光的发射通常出现在小于10纳秒的期间内。
新近，已证实了具有从三重态(“磷光”)发光的发射材料的OLED。Baldo等人的“Highly Efficient Phosphorescent Emission fromOrganic Electroluminescent Devices”，Nature，vol.395，151-154，1998；(“Baldo-I”)和Baldo等人的“Very high-efficiency greenorganic light-emitting devices based on electro-phosphorescence”，Appl.Phys.Lett.，vol.75，No.3，4-6(1999)(“Baldo-II”)，其全部内容引入本文作为参考。磷光还可称作“禁阻”跃迁，因为该跃迁需要改变自旋状态，而且量子力学表明这种跃迁是不利的。结果，磷光通常在超过至少10纳秒的期间内出现，而且通常大于100纳秒。如果磷光的自然发射寿命过长，三重态可能按照非发射机理衰变，进而不会发光。非常低的温度下，在含有杂原子和非共用电子对的分子里也常常能观察到有机磷光，2，2′-联吡啶就是这种分子。非发射衰变机理通常依赖于温度，因此在液氮温度下显示出磷光的材料可能在室温下不显示磷光。但是，如Baldo所论述的，可通过选择在室温下发磷光的磷光化合物来处理该问题。
通常，人们认为在OLED中按照约3∶1的比例产生激子，即，约75％的三重态和25％的单重态。参见Adachi等人的“Nearly 100％Internal Phosphorescent Efficiency In An Organic Light EmittingDevice”，J.Appl.Phys.，90，5048(2001)，其全部内容引入本文作为参考。许多情况下，单重态激子通过“系间窜跃”可容易地将能量转移至三重激发态，而三重态激子可能不容易将能量转移至单重激发态。结果，对于磷光OLED，100％的内量子效率在理论上是可能的。在荧光器件中，三重态激子的能量通常损失在将器件加热了的非辐射衰变过程中，结果使内量子效率更低得多。使用从三重激发态发光的磷光材料的OLED在例如，美国专利No.6,303,238中有所公开，其全部内容引入本文作为参考。
在产生磷光之前可能要从三重激发态跃迁至产生发射衰变的中间的非三重态。例如，与镧系元素配位的有机分子通常在定域在镧系金属上的激发态发出磷光。但是，这种材料并不会直接从三重激发态发出磷光，而是从以镧系金属离子为中心的原子激发态发光。铕的二酮化物络合物说明了一组这种类型的物质。
通过将有机分子非常接近地限制，优选键合在高原子序数的原子上可使从三重态发出的磷光相对于荧光有所增强。此现象称作重原子效应，其是通过已知的自旋轨道耦合机理产生的。从有机金属分子，例如三(2-苯基吡啶)铱(III)的激发的金属-配体电荷转移(MLCT)状态可观察到这种磷光性跃迁。
图1显示了有机发光器件100。该图并不必须按比例绘制。器件100可包括基底110、阳极115、空穴注入层120、空穴传递层125、电子阻挡层130、发射层135、空穴阻挡层140、电子传递层145、电子注入层150、保护层155和阴极160。阴极160为具有第一导电层162和第二导电层164的化合物阴极。器件100可通过依次沉积所述各层进行制造。
基底110可为能提供希望的结构性质的任何适当基底。基底110可为柔性或刚性。基底110可为透明、半透明或不透明的。塑料和玻璃为优选的刚性基底材料的例子。塑料和金属箔为优选的柔性基底材料的例子。为了有助于制造电路，基底110可为半导体材料。例如，基底110可为硅片，在其上面制造电路，其能控制随后沉积在基底之上的OLED。也可使用其它基底。可对基底110的材料和厚度进行选择以获得希望的结构和光学性质。
阳极115可为任何导电性能足以将空穴传递至有机层的适当的阳极。阳极115的材料优选具有大于约4eV(“高功函材料”)的功函。优选的阳极材料包括导电金属氧化物，例如铟锡氧化物(ITO)和铟锌氧化物(IZO)、铝锌氧化物(AlZnO)和金属。阳极115(和基底110)可具有足够的透明度以生成一个底部发射器件。优选的透明基底和阳极组合为可商购获得的沉积在玻璃或塑料(基底)之上的ITO(阳极)。柔性和透明基底-阳极的组合在美国专利No.5,844,363中有所公开，其全部内容引入本文作为参考。阳极115可为不透明和/或反射性的。对于一些顶部发射器件来说，反射性阳极115可能是优选的，其用来增加从器件顶部发射的光的量。可对阳极115的材料和厚度进行选择，以获得希望的导电性和光学性质。阳极115为透明时，对于特定的材料可能具有一个厚度范围，厚度足够大则提供希望的导电性，而厚度足够小则提供希望的透明度。也可使用其它阳极材料和结构。
空穴传递层125可包括能传递空穴的材料。空穴传递层130可为固有的(未掺杂的)或掺杂的。掺杂作用可用来提高导电性。α-NPD和TPD是固有空穴传递层的例子。p-掺杂的空穴传递层的例子是按照50∶1的摩尔比掺杂了F4-TCNQ的m-MTDATA，参见Forrest等人在美国专利申请No.10/173,682中所公开的内容，其全部内容引入本文作为参考。也可使用其它空穴传递层。
发射层135可包括在电流通过阳极115和阴极160之间时能发光的有机材料。虽然也可使用荧光发射材料，但优选发射层135含有磷光发射材料。优选使用磷光材料是因为这种材料具有更高的发光效率。发射层135还可包括能传递电子和/或空子的主体(host)材料，并掺杂有能捕获电子、空穴和/或激子的发射材料，从而激子通过光电发射机理从发射材料衰减。发射层135可包括结合了传递和发射性质的单一材料。无论发射材料是掺杂剂还是主要成分，发射层135都可包括其它材料，例如对发射材料的发射进行调协的掺杂剂。发射层135可包括多种发射材料，其结合起来能发射希望的光谱带的光。磷光发射材料的例子包括Ir(ppy)3。荧光发射材料的例子包括DCM和DMQA。主体材料的例子包括Alq3、CBP和mCP。发射和主体材料的例子公开在Thompson等人的美国专利No.6,303,238中，其全部内容引入本文作为参考。发射材料可按照许多种方式包括在发射层135中。例如，可将发射小分子结合在聚合物或枝状体分子中。也可使用其它发射层材料和结构。
电子传递层140可包括能够传递电子的材料。电子传递层140可为固有的(未掺杂的)或掺杂的。掺杂作用可用来提高导电性。Alq3是固有电子传递层的例子。n-掺杂的电子传递层的例子是按照1∶1的摩尔比掺杂了Li的BPhen，参见Forrest等人在美国专利申请No.10/173,682中所公开的内容，其全部内容引入本文作为参考。还可使用其它电子传递层。
阴极160可为本领域已知的任何适当材料或材料的组合，以使阴极160能够传导电子并将它们注入到器件100的有机层中。阴极160可为透明或不透明的，而且可为反射性的。金属和金属氧化物为适当的阴极材料的例子。阴极160可为单层，或者可具有化合物结构。图1显示了具有薄金属层162和较厚导电金属氧化物层164的化合物阴极160。在化合物阴极中，较厚层164的优选材料包括ITO、IZO和其它本领域已知的材料。美国专利No.5,703,436和No.5,707,745(其全部内容引入本文作为参考)公开了包括化合物阴极的阴极的例子，该化合物阴极具有例如Mg:Ag的金属薄层，其上覆盖了透明、导电、溅射沉积的ITO层。对于阴极160中与下面的有机层接触的部分，无论其是否为单层阴极160，化合物阴极的薄金属层162或一些其它部分均优选由功函低于约4eV(“低功函材料”)的材料制成。还可使用其它阴极材料及结构。
阻挡层可用于减少电荷载体(电子或空穴)和/或离开发射层的激子的数量。电子阻挡层130可沉积在发射层135和空穴传递层125之间，用以阻挡电子沿空穴传递层125的方向离开发射层135。同样，空穴阻挡层140可放置在发射层135和电子传递层145之间，用以阻挡空穴沿电子传递层140的方向离开发射层135。阻挡层还可用于阻挡激子散射出发射层。阻挡层理论及阻挡层的使用在Forrest等人的美国专利No.6,097,147和美国专利申请No.10/173,682中进行了详细描述，其全部内容引入本文作为参考。
通常，注入层由下述材料构成：可使电荷载体由一个层，例如电极或有机层到相邻有机层的注入得到改善的材料。注入层还可进行电荷传递功能。在器件100中，空穴注入层120可为改善空穴由阳极115到空穴传递层125的注入的任何层。CuPc是可用作来自ITO阳极115和其它阳极的空穴注入层的材料实例。在器件100中，电子注入层150可为使对电子传递层145的电子注入得到改善的任何层。LiF/Al是可用作电子注入层材料的例子，该电子注入层是从相邻层注入到电子传递层中的层。其它材料或材料的组合也可用作注入层。取决于特定器件的构造，注入层放置的位置可不同于器件100中所示的位置。Lu等人在系列号为No.09/931,948的美国专利申请中提供了更多注入层的例子，其全部内容引入本文作为参考。
保护层可用于在随后的制造过程中保护下面的层。例如，用于制造金属或金属氧化物顶电极的过程可能损坏有机层，而保护层可用于减小或消除这种损坏。在器件100中，保护层155可在制造阴极160的过程中减小对下面有机层的损坏。优选，对于可传递(器件100中的电子)的载体类型，保护层具有高载体移动性，从而其不会显著增大器件100的操作电压。CuPc、BCP和各种金属酞菁是可用在保护层中的材料的例子。还可使用其它材料或材料的组合。保护层155的厚度优选足够厚，从而在沉积有机保护层160后的制造过程中对下面的层产生的损坏很小或没有，但也不能太厚以免显著增大器件100的操作电压。可对保护层155进行掺杂以提高导电性。例如，CuPc或BCP保护层160可掺杂Li。在Lu等人的系列号为No.09/931,948的美国专利申请中可找到对保护层的更详细描述，其全部内容引入本文作为参考。
图2显示了反相OLED 200。该器件包括基底210、阴极215、发射层220、空穴传递层225和阳极230。器件200可通过按所述顺序沉积各层来制造。由于最常见的OLED构造是阴极放置在阳极之上，而器件200却是阴极215放置在阳极230之下，因此器件200可称作“反相”OLED。与所述器件100相类似的材料可用在器件200的相应层中。图2提供了一个怎样从器件100中删除一些层的例子。
通过非限制性实施例提供了图1和2中所示的简单的层状结构，而且应理解为本发明的实施方案可与各种其它结构结合使用。所述的具体材料和结构为示范性质，还可使用其它材料和结构。根据设计、效能和成本因素，可将以不同方式描述的各种层结合起来而获得功能性OLED，或者完全删除所述层。还可包括其它未具体说明的层。可使用与具体说明的那些材料不同的其它材料。虽然本文中提供的许多实施例都将各层描述为包括单一材料，但应该理解为可以使用组合材料，例如主体材料和掺杂剂的混合物，或更广泛的混合物。而且，所述层可具有各种子层。本文中对不同层的命名并非意图进行严格限制。例如，在器件200中，空穴传递层225将空穴传递和注入到发射层220中，因此可被描述为空穴传递层或空穴注入层。一个实施方案中，OLED可被描述为具有放置在阴极和阳极之间的“有机层”。该有机层可包括一个单层，或还可进一步包括所述不同有机材料的多个层，例如，参考图1和2。
还可使用未具体描述的结构和材料，例如Friend等人在美国专利No.5,247,190中公开的包括聚合材料的OLED(PLED)，该文献的全部内容引入本文作为参考。根据其它实施例，还可使用具有单一有机层的OLED。OLED可为叠层结构，例如Forrest等人在美国专利No.5,707,745中所作的描述，其全部内容引入本文作为参考。OLED结构可脱离图1和2中所示的简单的层状结构。例如，基底可包括有角度的反射性表面，用以改善输出-耦合，例如Forrest等人在美国专利No.6,091,195中描述的台式结构，和/或Bulovic等人在美国专利No.5,834,893中描述的纹孔结构，其全部内容引入本文作为参考。
各个实施方案的任何层都可用任何适当的方法进行沉积。对于有机层，优选的方法包括热蒸发、喷墨，如美国专利No.6,013,982和No.6,087,196中的描述，其全部内容引入本文作为参考，有机气相沉积法(OVPD)，如Forrest等人在美国专利No.6,337,102中的描述，其全部内容引入本文作为参考，以及通过有机气相喷印(OVJD)进行沉积，如美国专利申请No.10/233,470中的描述，其全部内容引入本文作为参考。其它适当的沉积方法包括旋涂和其它溶液基处理方法。对于其它层，优选的方法包括热蒸发。优选的图案化方法包括掩模沉积、冷焊法，如美国专利No.6,294,398和No.6,468,819中所作的描述，其全部内容引入本文作为参考，以及与一些沉积方法，如喷墨和OVJD相联合的图案化方法。还可使用其它方法。可对欲沉积的材料进行变型，以使其与特定的沉积方法相适合。
根据本发明实施方案制造的器件可结合在各种消费产品中，包括平板显示器、计算机监测器、电视、广告牌、室内或室外照明灯和/或信号灯、警告牌、全透明显示器、柔性显示器、激光打印机、电话、手机、个人数字助理装置(PDA)、膝上型计算机、数码摄像机、可携式摄像机、探视器、微显示器、车辆、大面积屏壁、电影院或体育场屏幕或标记。可使用各种调节机制来控制根据本发明制造的器件，包括无源矩阵和有源矩阵。许多器件意图用于适合人的温度范围内，例如18℃-30℃，更优选在室温(20-25℃)下。
本文中描述的材料和结构可应用在非OLED器件中。例如，其它光电子器件，如有机太阳能电池和有机光检测器中可以使用该材料和结构。更通常，有机器件，如有机晶体管中可以使用该材料和结构。
用于全色显示器的工业标准要求饱和红色、饱和绿色和饱和蓝色发射材料。希望具有一种可与大范围彩色坐标系相“调谐”的材料，从而可获得特定的颜色，例如高度饱和的颜色。
某种程度上，由于使用磷光发射材料可获得高效率，因此该材料引起了人们的兴趣。这种材料的例子为Ir(ppy)3：
式1：
在本发明的实施方案中，提供了一种高度调谐的磷光发射材料。该材料可包括具有下列结构的配体：
式2：
式2中，环A和B可为任何芳环或杂芳环。优选，环B为芳环，因为杂芳基B环可能难于合成。优选，环A和B为5-或6-元芳环体系。由于人们认为当A和B为芳环时器件稳定性更好，因此芳环比杂芳环更优选。环A和B可包括单个或多个杂原子。氮为适当的杂原子的例子。环A和B可为苯环化的(benzannulated)环，还可含有取代基。H或任意的取代基都可用于环A和B以及R″上。优选的取代基包括烷基、烷氧基、氨基、卤素、羧基、芳基、杂芳基、烯基和炔基。环A和B可选自相同的环系，或者还可不同。环A和B可包括相同或不同的取代基。R″可为H或任意的取代基。
式2的配体可连接在原子量大于40的金属M上。优选的金属包括Ir、Pt、Pd、Rh、Re、Ru、Os、Tl、Pb、Bi、In、Sn、Sb、Te、Au和Ag。更优选，金属为Pt。最优选，金属为Ir。可使多个配体与金属连接。在一个实施方案中，配体按照下列方式连接在金属M上：
式3：
环A和B以及R″如式2中的描述。
“X”可称作“辅助配体”。优选的配体包括任意的单-阴离子配体。X可在单个或多个位置处与金属配位。例如，X可为二齿配体。X配体称作“辅助”是因为人们认为其可以改进材料的光敏特性，而不是直接对光敏特性起作用。通过比较，左侧的配体被称作“光敏”配体，因为人们认为它对材料的光敏特性起作用。光敏和辅助的定义是意图作为非限制性理论。
“m”是特定类型的光敏配体的数量，“n”是特定类型辅助配体的数量。取决于金属M，可有确定数量的配体连接于金属上。通常，配体为二齿，其意指与金属形成两个键，但并不必须是二齿配体。例如，两个氯原子可替代二齿辅助配体连接在金属上。“m”至少为1，且可以为大于0至金属可连接的最大配体数量的任意整数。“n”可为0，且可为大于0的整数，但要满足“m”至少为1的要求。“m”+“n”可小于可连接于M上的配体总数，这样，除式2中具体说明的那些配体之外的配体也可连接于M上。这些额外的配体可为光敏或辅助物质。对于铱，其上可连接3个二齿配体，“m”可为1、2或3，“n”可为0、1或2。
优选的辅助配体包括乙酰丙酮化物(acac)，甲基吡啶化物(pic)和二新戊酰基甲烷化物(叔丁基acac)。一些优选的辅助配体具有下列的根据式4(pic)、式5(acac)和式6(叔丁基acac)的结构。还可使用其它辅助配体。在Lamansky等人的PCT申请公开文本WO02/15645A1的89-90页中还有其它辅助配体，其引入本文作为参考：
甲基吡啶化物 乙酰丙酮化物 二新戊酰基甲烷化物
在优选的实施方案中，n为0，m为可连接至金属上的最大配体数量。例如，对于Ir，在该优选实施方案中m为3，而且该结构可称作“三体(tris)”结构。优选采用该三体结构，因为人们认为其特别稳定。该三体结构的稳定性再联合R3基团提供的稳定性和颜色调谐就可产生特别稳定的发射蓝光的磷光材料。
在一个实施方案中，m+n等于可连接于所述金属上的二齿配体的总数一例如，对于Ir为3。在另一个实施方案中，m+n可小于可连接于金属上的二齿配体的最大数量，这种情况下，其它配体—辅助配体、光敏配体或另外的配体也可连接在金属上。优选，如果有不同的光敏配体连接于金属上，则每个光敏配体具有式2中所示的结构。
在一个实施方案中，式3的材料具有式7的结构：
式7：
Y可选自C和N。优选，Y为C，因为人们认为当顶部和底部的环为芳环而非杂芳环时使用式3的化合物得到更稳定的器件。R2、R3、R4、R5、R′2、R′3、R′4、R′5和R″可各自独立选自H和任意的取代基。具有多个取代基时，R″、R2、R3、R4、R5、R′2、R′3、R′4和R′5可连接在另一个R″、R2、R3、R4、R5、R′2、R′3、R′4和R′5上形成环。
应该理解，本文中描述的各种实施方案只是作为实施例，并不意图限制发明范围。例如，在不偏离本发明精神的条件下，本文中描述的许多材料和结构都可被其它材料和结构所取代。应该理解，关于本发明为什么可行的各种理论并不意图进行限制。例如，有关电荷迁移的理论并不意图起限制作用。
材料定义：
本文中所用的缩写指下列材料：
CBP：4，4′-N，N′-二咔唑-联苯
m-MTDATA：4，4′，4″-三(3-甲基苯基苯基氨基)三苯基胺
Alq3：8-三-羟基喹啉合铝
BPhen：4，7-二苯基-1，10-菲咯啉
n-BPhen：n-掺杂BPhen(掺杂了锂)
F4-TCNQ：四氟-四氰基-醌二甲烷
p-MTDATA：p-掺杂的m-MTDATA(掺杂了F4-TCNQ)
Ir(ppy)3：三(2-苯基吡啶)-合铱
Ir(ppz)3：三(1-苯基吡唑(pyrazoloto)，N，C(2′)合铱(III)
BCP：2，9-二甲基-4，7-二苯基-1，10-菲咯啉
TAZ：3-苯基-4-(1′-萘基)-5-苯基-1，2，4-三唑
CuPc：铜酞菁
ITO：铟锡氧化物
NPD：萘基-苯基-二胺
TPD：N，N′-双(3-甲基苯基)-N，N′-双(苯基)联苯胺
BAlq：双(2-甲基-8-喹啉)-4-苯基苯酚铝(III)
mCP：1，3-二咔唑-苯
DCM：4-(二氰基亚甲基)-6-(4-二甲基氨基苯乙烯基-2-甲基)-4H-吡喃
DMQA：N，N′-二甲基喹吖酮
试验：
现在将对本发明具体的代表性实施方案进行描述，包括怎样实施这些实施方案。应该理解，该具体方法、材料、条件、过程参数、装置等并不对本发明进行必要的限制。
通常，苯并咪唑配体的合成可按照下列反应A和B中描述的两个步骤进行。取代或未取代芳香胺可商购获得或经反应A合成。在反应A中，由图示式I代表的取代或未取代2-氯硝基苯在无杂质条件下通过氮气氛下的回流来与取代苯胺和诸如NaHCO3的碱反应，得到图示式II代表的化合物。纯化后，可使用任意数量的还原剂，即，肼，并加入FeCl3·6H2O将产物还原为相应的芳香族二胺，从而得到III
反应方案A
取代或未取代苯并咪唑配体的合成可使用反应B中所述的由图示式III代表的二胺进行。然后可按照Synthesis，2000，10，1380-90中所述的、反应方案B中的描述使二胺III与取代或未取代苯并咪唑反应，得到图示式IV代表的取代苯并咪唑配体。
反应方案B
在反应C中，可在溶剂，例如，2-甲氧基乙醇或2-乙氧基乙醇和水存在下，在回流条件下使反应B中制得并由图示式IV代表的苯并咪唑配体与各种金属，例如，铱、铂反应，制得图示式V代表的二氯桥接二聚体。反应结束后形成的固体沉积物用真空过滤法收集，如果需要则进一步纯化。
反应C
在反应D中，由图示式VI代表的二氯桥接二聚体可与各种单阴离子配位体，如乙酰丙酮化物(acac)、吡啶甲酸、4-二甲基氨基吡啶甲酸(DMAPic)，和单阴离子金属-碳配体，如取代的2-苯基吡啶等反应，且该配体用X表示。分离出来的由图示VII表示的最终产物用标准方法进行纯化。
反应D
使用上述合成路径或类似的路径制备表1中列出的根据式7的材料：
表1
| Cmp | M | R2 | R3 | R4 | R5 | R″ | Y | R′2 | R′4 | X | C.I.E(MeCl2) | PL(nm) |
| 1 | Ir | H | H | H | H | CH3 | C | H | H | acac | 0.32，0.60 | 509 |
| 2 | Ir | F | H | F | H | CH3 | C | H | H | pic | 0.25，0.48 | 476 |
| 3 | Ir | H | H | OCH3 | H | CH | C | H | H | acac | 0.23，0.53 | 488 |
| 4 | Ir | H | H | CF3 | H | CH3 | C | H | H | pic | 0.34，0.59 | 510 |
| 5 | Ir | H | CF3 | H | H | H | C | H | H | pic | 0.28，0.55 | 490 |
| 6 | Ir | H | H | H | H | C6H5 | C | H | CF3 | acac | 0.37，0.60 | 522 |
| 7 | Ir | H | H | OCH3 | H | CH3 | C | H | H | tris | 0.25，0.54 | 488 |
| 8 | Ir | H | H | N(CH3)2 | H | C6H5 | C | H | H | acac | 0.35，0.60 | 519 |
| 9 | Ir | H | H | CF3 | H | C6H5 | N | H | H | acac | 0.54，0.45 | 584 |
| 10 | Ir | H | H | H | H | pOCH3Ph | C | H | H | acac | 0.36，0.60 | 515 |
| 11 | Ir | Cl | Cl | H | Cl | C6H10 | C | H | OCH3 | acac | 0.50，0.49 | 580 |
| 12 | Ir | OCH3 | H | OCH3 | H | CH3 | C | H | H | acac | 0.33，0.53 | 494 |
| 13 | Ir | F | F | F | H | CH3 | C | H | H | acac | 0.28，0.55 | 490 |
| 14 | Ir | F | F | F | H | CH3 | C | H | H | pic | 0.28，0.55 | 488 |
| 15 | Ir | Cl | Cl | H | Cl | CH3 | C | H | H | acac | 0.26，0.47 | 470 |
| 16 | Ir | H | CF3 | F | H | CH3 | C | H | H | acac | 0.27，0.53 | 485 |
| 17 | Ir | H | CF3 | F | H | CH3 | C | H | H | pic | 0.24，0.46 | 474 |
| Cmp | M | R2 | R3 | R4 | R5 | R″ | Y | R′2 | R′4 | X | C.I.E(MeCl2) | PL(nm) |
| 18 | Ir | H | F | OCH3 | H | CH3 | C | H | H | acac | 0.29，0.52 | 488 |
| 19 | Ir | H | 二氧环戊烯环 | H | CH3 | C | H | H | acac | 0.35，0.54 | 522 | |
| 20 | Ir | H | CF3 | H | CF3 | CH3 | C | H | H | acac | 0.30，0.56 | 490 |
| 21 | Ir | H | CF3 | H | CF3 | CH3 | C | H | H | pic | 0.30，0.56 | 488 |
| 22 | Ir | H | H | OCF3 | H | CH3 | C | H | H | acac | 0.32，0.58 | 500 |
| 23 | Ir | H | H | OCF3 | H | CH3 | C | H | H | pic | 0.27，0.54 | 486 |
| 24 | Ir | CF3 | H | CF3 | H | CH3 | C | H | H | acac | 0.55，0.45 | 580 |
| 25 | Ir | F | F | F | F | CH3 | C | H | H | acac | 0.32，0.58 | 496 |
| 26 | Pt | H | H | H | H | CH3 | C | H | H | acac | 0.31，0.56 | 486 |
| 27 | Pt | F | H | F | H | CH3 | C | H | H | acac | 0.28，0.52 | 479 |
| 28 | Ir | H | H | H | H | CH2CH2-R′2 | C | CH2CH2-R″2 | H | acac | 0.33，0.60 | 508 |
对于制备的各种材料，R′3＝R′5＝H。在辅助配体X上引入“三体”表示其偏离式7，因为没有辅助配体X，而是三个光敏配体(m＝3，n＝0)。在化合物28中，R″和R′2取代基相连接，即，两个取代基位置通过亚乙基基团连接起来。PL是光致发光波长的峰值，用nm度量。Pt化合物也偏离了式7，因为Pt只可以配位在两个二齿配体上，从而使表1中列出的Pt化合物具有一个辅助配体，且只有一个光敏配体(m＝1，n＝1)，而不是式7中列出的两个光敏配体。
对于化合物1-28中的每个化合物，取其少量溶解在二氯甲烷中。对每个溶液进行光抽，并测定所得的光致发光谱图。将所得的峰波长和CIE坐标值列于表1中。
优选实施方案中，化合物1具有式8的结构：
制备并表征了包括化合物1、3和5以及Ir(ppy)3的器件。在涂覆了约130-150nm ITO阳极(得自Colorado，Longmont，Applied FilmsCorp.)的玻璃基底之上制备所有试样。在＜1×10-6托的压力下用热蒸发方法沉积薄膜。首先，以0.3埃/秒的速率将CuPc沉积在阳极之上，成为10nm厚的空穴注入层。接下来，以1.5埃/秒的速率将NPD沉积成30nm厚的空穴传递层。然后，通过不同来源的共-蒸发作用沉积发射层。各个器件都具有以CBP为主体材料的发射层，其特征在于掺杂了6重量％的化合物。制备的器件以化合物1、3和5以及Ir(ppy)3作为掺杂物。以1.6埃/秒的速率(具有6％的掺杂物)将发射层的CBP沉积成30nm厚度。接下来，在发射层之上，以1.0埃/秒的速率将BAlq沉积为10nm厚的空穴阻挡层。然后，在空穴阻挡层之上，以1.0埃/秒的速率将Alq3沉积为40nm厚的电子传递层。然后，在电子传递层之上，以0.5埃/秒的速率将氟化锂(LiF)沉积为0.5nm厚的电子注入层。最后，以2埃/秒的速率将铝(Al)阴极沉积在电子注入层之上，厚度为100nm，从而制成该有机发光器件。
包括化合物1、3和5以及Ir(ppy)3的器件的特征在于多种亮度。图3显示了发光效率-亮度曲线图。曲线310、320、330和340分别对应于掺杂了化合物1、化合物3、化合物5和Ir(ppy)3的器件。图4显示了外量子效率-亮度曲线图。曲线410、420、430和440分别对应于掺杂了化合物1、化合物3、化合物5和Ir(ppy)3的器件。
图3和4显示出用化合物1制造的器件比用Ir(ppy)3制造的器件更有效。虽然化合物3显示出与Ir(ppy)3等效，而化合物5显示出较差的效率，但对于Ir(ppy)3来说，器件结构已被优化。使用不同结构可使化合物1、3和5的效率相对于Ir(ppy)3有所改善。在对于Ir(ppy)3来说被优化的器件结构中，与Ir(ppy)3相比化合物1具有更大的效率，这表明化合物1显示出效率上的显著改进。图3进一步显示出使用化合物1的器件在亮度为500cd/m2时能够获得至少20cd/A，更优选22.5cd/A的发光效率，，其优于试验的Ir(ppy)3器件。
按照上述方法制造一个器件，只是以12％而非6％的浓度将化合物5掺杂在发射层中。具有12％掺杂物的器件与掺杂了6％化合物5的器件显示出稍微改善的效率，其表明通过优化器件可使效率获得一些改善。
虽然本发明就特别的实施例和优选实施方案进行了描述，但应该理解，本发明并不限于这些实施例和实施方案。因此，所要求的本发明包括对本领域熟练技术人员来说显而易见的、本文中所述的特定实施例和优选实施方案的变型。
Claims (35)
1.一种有机发光器件，包括：
(a)阳极；
(b)阴极；和
(c)放置在阳极和阴极之间的发射层，该发射层包括具有下列结构的材料：
其中，M为原子量大于40的金属，m至少为1，n至少为0，R″为H或任意的取代基，X为辅助配体，A选自芳环和杂芳环，且B为芳环。
2.权利要求1的器件，其中A和B中至少一个包括取代基。
3.权利要求1的器件，其中M选自Ir、Pt、Pd、Rh、Re、Ru、Os、Tl、Pb、Bi、In、Sn、Sb、Te、Au和Ag。
4.权利要求1的器件，其中M为Ir。
5.权利要求1的器件，其中M为Pt。
6.权利要求1的器件，其中n为0。
7.权利要求1的器件，其中该发射材料被混合入聚合物中。
8.权利要求1的器件，其中该发射材料被混合入枝状体中。
9.权利要求1的器件，其中该发射层还包括主体材料。
10.权利要求9的器件，其中该发射材料为主体材料中的掺杂物。
11.权利要求1的器件，其中该发射材料基本上由发射材料的无杂质膜组成。
12.权利要求3的器件，其中m为2，且其中n为1。
13.权利要求1的器件，其中发射层包括具有下列结构的材料：
其中：
M为Ir；
Y为C；和
R2、R3、R4、R5、R′2、R′3、R′4和R′5彼此独立地选自H和任意的取代基。
14.权利要求13的器件，其中R2、R3、R4、R5、R′2、R′3、R′4和R′5各自为氢原子，R″为-CH3，以及X为acac。
15.权利要求13的器件，其中R2、R3、R4、R5、R′2、R′3、R′4和R′5中的至少一个与R2、R3、R4、R5、R′2、R′3、R′4和R′5中的另一个相连接而形成一个环。
16.一种有机发光器件，包括：
(a)阳极；
(b)阴极；和
(c)放置在阳极和阴极之间的发射层，该发射层包括具有配体的材料，该配体具有下列结构：
其中，该配体连接于原子量大于40的金属，并且A和B为杂环，且R″选自H和任意的取代基。
17.一种有机发光器件，包括：
(a)阳极；
(b)阴极；和
(c)放置在阳极和阴极之间的发射层，该发射层包括具有下列结构的材料：
18.权利要求1的器件，其中该器件在亮度为500cd/m2时具有至少22.5cd/A的发光效率。
19.一种具有下列结构的发射材料：
其中，M为原子量大于40的金属，m至少为1，n至少为0，R″为H或任意的取代基，X为辅助配体，A选自芳环和杂芳环，且B为芳环。
20.权利要求19的发射材料，其中A和B中至少一个包括取代基。
21.权利要求19的发射材料，其中M选自Ir、Pt、Pd、Rh、Re、Ru、Os、Tl、Pb、Bi、In、Sn、Sb、Te、Au和Ag。
22.权利要求19的发射材料，其中M为Ir。
23.权利要求19的发射材料，其中M为Pt。
24.权利要求19的发射材料，其中n为0。
25.权利要求19的发射材料，其中该发射材料被混合入聚合物中。
26.权利要求19的发射材料，其中该发射材料被混合入枝状体中。
27.权利要求19的发射材料，其中该发射层还包括主体材料。
28.权利要求27的发射材料，其中该发射材料为主体材料中的掺杂物。
29.权利要求19的发射材料，其中该发射材料基本上由发射材料的无杂质膜组成。
30.权利要求21的发射材料，其中m为2，且其中n为1。
31.权利要求19的发射材料，其中该发射层包括具有下列结构的材料：
其中：
M为Ir；
Y为C；和
R2、R3、R4、R5、R′2、R′3、R′4和R′5彼此独立地选自H和任意的取代基。
32.权利要求31的发射材料，其中R2、R3、R4、R5、R′2、R′3、R′4和R′5各自为氢原子，R″为-CH3，以及X为acac。
33.权利要求31的发射材料，其中R2、R3、R4、R5、R′2、R′3、R′4和R′5中的至少一个与R2、R3、R4、R5、R′2、R′3、R′4和R′5中的另一个相连接而形成一个环。
34.具有配体的发射材料，该配体具有下列结构：
其中，该配体连接于原子量大于40的金属，并且A和B为杂环，且R″选自H和任意的取代基。
35.具有下列结构的发射材料：
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- 2003-11-07 WO PCT/US2003/035535 patent/WO2004045002A1/en active Application Filing
- 2003-11-07 AT AT03768762T patent/ATE508473T1/de not_active IP Right Cessation
- 2003-11-07 CN CN2003801061055A patent/CN1726606B/zh not_active Expired - Lifetime
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Also Published As
| Publication number | Publication date |
|---|---|
| DE60337024D1 (de) | 2011-06-16 |
| WO2004045002A1 (en) | 2004-05-27 |
| ATE542252T1 (de) | 2012-02-15 |
| EP2259361B1 (en) | 2012-01-18 |
| US6687266B1 (en) | 2004-02-03 |
| EP1561240B1 (en) | 2011-05-04 |
| KR20050086462A (ko) | 2005-08-30 |
| EP2259361A1 (en) | 2010-12-08 |
| ATE508473T1 (de) | 2011-05-15 |
| JP4656944B2 (ja) | 2011-03-23 |
| AU2003291370A8 (en) | 2004-06-03 |
| AU2003291370A1 (en) | 2004-06-03 |
| JP2006505956A (ja) | 2006-02-16 |
| KR101074445B1 (ko) | 2011-10-17 |
| EP1561240A1 (en) | 2005-08-10 |
| CN1726606B (zh) | 2010-09-22 |
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