CN1625552B - 电子传输新材料和使用该材料的有机电致发光显示器 - Google Patents

电子传输新材料和使用该材料的有机电致发光显示器 Download PDF

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CN1625552B
CN1625552B CN038001551A CN03800155A CN1625552B CN 1625552 B CN1625552 B CN 1625552B CN 038001551 A CN038001551 A CN 038001551A CN 03800155 A CN03800155 A CN 03800155A CN 1625552 B CN1625552 B CN 1625552B
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尹锡喜
裴在顺
李允九
任城甲
李载澈
金芝垠
金公谦
孙世焕
韩荣圭
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Abstract

用于电子注入/传输和发射层的新材料可大大改进有机电致发光显示器的稳定性。包括这些材料的电致发光显示器在低电压水平下产生蓝色光。这些新的有机材料包括在9、10取代蒽的2或2，6-位置引入1至2个咪唑官能团的化合物。包含这些材料的有机化合物层的有机电致发光显示器具有高效率、热稳定性、操作稳定性和在操作前后保持驱动电压的特点。

Description

电子传输新材料和使用该材料的有机电致发光显示器
技术领域
本发明涉及用于电子传输和发射层的新材料，以及使用该材料的有机电致发光显示器。
背景技术
电致发光显示器是使用固体荧光材料的发光器件。现在所用的技术是用无机材料作为发光体的无机电致发光显示器。然而，常规无机电致发光显示器发光时要求100V或更高的高电压，并且其发蓝色光困难。其结果是通过RGB(红、绿、蓝)三色的全彩色显示困难。
尽管研究使用有机材料的电致发光器件已引起关注很长时间了，但与常规显示器，如：液晶显示器和阴极射线管相比，因其缺乏稳定性且效率低，仅有很少量的器件实现了商品化。有机电致发光显示器依据的理论是：借助阳极和阴极向小分子(可升华的分子)或聚合物的有机薄膜内注入电子和空穴，形成激子，当高能量激子回到其基态时产生具有特定波长的光。这种效应首先由Pope等人在1965通过蒽单晶发现(M.Pope et al.，J.Chem.Phys.，42，2540，1965)。1987年，柯达公司的Tang提出具有将有机材料分为空穴传输层和发射层的功能分离型叠层结构的有机电致发光显示器，已证实，可获得10V或更低的低电压以及高亮度(Tang，C.W.；VanSlyke，S.A.Appl.Phys.Lett.1987，51，913)。从此，有机电致发光显示器开始引起人们的注意。目前，具有这种相同的功能分离型叠层结构的有机电致发光显示器的研究正在进展。
如图1所示，常规有机电致发光显示器包括：基材(1)、阳极(2)、用于从阳极接受空穴的空穴注入层(3)、用于传输空穴的空穴传输层(4)、发射层(5)(在此空穴和电子结合而发光)、用于从阴极接受电子并传输到发射层的电子传输层(6)和阳极(7)。发射层(5)可由两种或多种不同分子构成，分别承担发光、传输电子和空穴的功能，以进一步提高器件的效率。通常，将即可传输空穴也可传输电子的分子称为主体分子，并将其它的发光分子称为掺杂分子。通常，发射层(5)由大量的主体分子和少量(1～20％)掺杂分子组成。对掺杂分子的要求包括高荧光或磷光效率以及相对于主体分子的合适带结构。根据情况，在电子传输层(6)或空穴传输层(4)上掺杂少量荧光或磷光染料，以将发射层包括在其中，而无单独的发射层(5)。还可以对多层如电子传输层、发射层和空穴传输层进行掺杂，以改进操作稳定性或具有多发射。两个电极之间的有机薄膜通过真空沉积、旋涂、喷墨印刷、辊涂等方法形成。为从阴极有效注入电子，常常插入单独的电子注入层。
制造具有多层薄膜结构的有机电致发光显示器的原因包括使电极与有机层之间的界面稳定。此外，在有机材料中，电子和空穴的移动性明显不同，因此，若使用合适的电子传输和空穴传输层，则空穴和电子可有效转移至发光层。此外，若在发射层中具有平衡的空穴和电子的密度，则发光效率将被提高。
上述有机层的适当组合可增强器件的效率，延长寿命。然而，难以找到满足用于实际器件中的所有要求的有机材料。例如，三-(8-羟基喹啉)铝(Alq3)用作电子传输材料已十五年以上了，并且有很多文献和专利声称它们具有优异的性能。因此，找到在所有实用性的方面，如：高效、热稳定性、操作稳定性和在操作前后保持驱动电压稳定性，均具有比常规材料性能优异的分子是至关重要的。
发明内容
本发明基于上述考虑提出，并且旨在克服现有电致发光显示器存在的问题。本发明的一个目的是提供一种用于电子传输和发射层的新材料，可大大改进使用该材料的有机电致发光显示器的发光效率、稳定性和显示寿命。
本发明同时提供如下化学式1表示的化合物、化学式2表示的化合物、化学式3表示的化合物、化学式4表示的化合物和化学式5表示的化合物：
(化学式1)
Figure S03800155119950507D000031
(化学式2)
Figure S03800155119950507D000032
(化学式3)
(化学式4)
Figure S03800155119950507D000041
(化学式5)
Figure S03800155119950507D000042
其中：
R1和R2各自独立地或同时为氢原子、C1-20脂肪族烃、苯、萘、联苯、蒽或衍生自芳族杂环或芳环的基团，且R1和R2不能同时为氢原子；
Ar为苯、萘、联苯、蒽或衍生自芳族杂环或芳环的基团；
R3为氢原子、C1-20烷基或脂肪族烃、取代或未取代的苯、萘、联苯、蒽或芳族杂环或芳环；
R4为氢原子、C1-12烷基或脂肪族烃、苯、萘、联苯、蒽或衍生自芳族杂环或芳环的基团。
本发明还提供一种具有一个有机层的有机电致发光器件，该有机层含有选自上述化学式1、化学式2、化学式3、化学式4或化学式5或其混合物的有机化合物。
在本发明的电致发光显示器中，至少一层有机层可处于注入空穴的阳极和注入电子的阴极之间。此外，至少一层有机层可为完成电子注入和传输功能的电子注入/传输层。进一步，至少一层有机层可为完成电子注入和发光功能的电子注入/传输和发射层。更进一步，至少一层有机层可为完成电子传输和光发射功能的电子传输和发射层。此外，其中一层有机层可为完成光发射功能的发射层。
本发明还涉及一种有机电致发光显示器，该显示器具有基材、在基材上的阳极、在阳极上的空穴注入层、在空穴注入层上的空穴传输层、在传输层上的发射层、在发射层上的电子传输层和在电子传输层上的阴极；并且至少在发射层中包含有机化合物。或者，该有机电致发光显示器具有基材、在基材上的阳极、在阳极上的空穴注入层、在空穴注入层上的空穴传输层、在空穴传输层上的发射层、在发射层上的电子注入/传输层、在电子传输层上的阴极；并且至少在电子注入/传输层之一中包含有机化合物。
应理解，前面的描述和下面的详细描述都是示例性和解释性的，并且将提供对要求保护的本发明的进一步解释。
附图说明
附图以提供对本发明的进一步理解。附图说明本发明的实施方案并与说明书一起解释本发明实施方案的原理。
图1为说明有机电致发光显示器的一个例子的横截面图。
图2给出实施例6中的器件的亮度与驱动时间的函数图。
图3给出对比例1中的器件的亮度与驱动时间的函数图。
图4给出对比例1中的器件的亮度与驱动时间的函数图。
图5给出实施例6、对比例1和对比例2中电压与驱动时间的函数图。
图6给出实施例7中的器件的亮度与驱动时间的函数图。
图7给出实施例7和对比例3中的电压与驱动时间的函数图。
具体实施方式
本发明的优点从下面给出的详细描述中将变得更为显而易见。然而，应理解，这些详细描述和具体的实施例，尽管给出了本发明的优选实施方案，但仅以说明方式给出，因为从该详细描述中对本发明精神和范围内的各种变化和改进对于本领域熟练技术人员来说是显而易见。
本发明提供一种新材料，其中将含1至2个咪唑基的基团在9，10取代蒽的2或2，6-位置引入。将该材料包含在有机电致发光(EL)器件的有机化合物层中，以提高发光效率和延长寿命，还提供在有机化合物层中包括该材料的有机电致发光器件。
下面解释应用本发明新材料的有机电致发光器件的结构。
图1为有机电致发光显示器适用结构的一个例子的横截面图。图标1表示基材，2表示阳极，3表示空穴注入层，4表示空穴传输层，5表示发射层，6表示电子传输层，7表示阴极。
基材(1)用于支撑有机电致发光器件，可使用硅片、石英或玻璃板、金属板、塑料膜或片等。此外，当器件制造工艺由阴极一侧开始时，基材层可为阳极上薄薄的一层保护层。
在基材(1)上，设置阳极(2)。阳极(2)将空穴注入处于其上的空穴注入层(3)。为此，可使用金属，如：铝、金、银、镍、钯、铂等；或具有大的工函数的材料，如：氧化铟-锡(ITO)、氧化铟-锌(IZO)等；还可以使用导电聚合物，如：炭黑、聚噻酚、聚吡咯烷酮或聚苯胺等。
在阳极(2)上，可设置空穴注入层(3)。用于空穴注入层的材料应自阳极具有高空穴注入效率，并能有效的传输注入的空穴。为此，该材料应具有低离子化势、对可见光的高透明性并对空穴具有优异的稳定性。
在空穴注入层(3)上，设置空穴传输层(4)。空穴传输层(4)自空穴注入层(3)接受空穴，并传输至位于其上的发射层(5)，并且它具有高空穴传输度、对空穴良好的稳定性并能很好地阻塞电子。除了这些要求外，若施用于车辆的显示器，则还要求显示器的耐热性，因此优选具有玻璃化温度(Tg)超过70℃的材料。  满足这些要求的材料包括NPD(或NPB)(N′，N-二(1-萘基)-N，N′-二苯基-1，1′-二苯基-4，4′-二胺)，螺-芳胺化合物、苝-芳胺化合物、  氮杂环庚三烯化合物、双(二苯基乙烯基苯基)蒽，氧化硅-锗化合物、硅芳胺化合物等。
在空穴传输层(4)上，设置发射层(5)。在发射层(5)中，分别自阳极(2)和阴极(7)注入的空穴和电子再结合以发射光，发射层(5)由具有高量子效率的材料形成。为制备稳定的器件，重要的是，具有对空穴和电子都稳定的发射材料。若发射材料对其中一种载流子(空穴或电子)缺乏稳定性，则必须对发射材料提供特殊环境以使其不暴露在能破坏发射材料的载流子下。回避这种条件的一种方法是掺杂可代替主体材料接受和传输问题载流子的荧光或磷光材料。另一种方法是引入过量的另一载流子使问题载流子进攻中性主体材料的的机会降至最低。因此，在保持两种载流子平衡并引入合适量的掺杂物质以使量子效率最大化的同时产生这种条件是非常困难的。此外，选择能够产生这种条件的掺杂剂受到限制。为此，具有对两种载流子都稳定的发射材料是至关重要的。
用于发射层的材料包括，绿光材料，Alq3；和蓝光材料，Balq(8-羟基喹啉铍盐)，DPVBi(4，4′-双(2，2-二苯基乙烯基)-1，1′-联苯)，螺-DPVBi(螺-4，4′-双(2，2-二苯基乙烯基)1，1′-联苯)，LiPBO(2-2(-苯并恶唑基)-苯酚锂盐)，铝-喹啉金属配合物，咪唑、  噻唑和恶唑的衍生物及其金属配合物等等。为提高蓝色发光效率，可在其中掺杂少量苝和BczVBi(3，3′[(1，1′-联苯)]-4，4′-二基二-2，1-乙烯二基)双(9-乙基)-9H-咔唑)，或可在其中掺杂DSA(二苯乙烯基胺)。红光材料，可在绿色发射材料中掺杂少量材料如DCJTB([2-(1，1-二甲基乙基)-6-[2-(2，3，6，7-四氢-1，1，7，7-四甲基-1H，5H-苯并(1，j)喹啉-9-基)乙烯基]4H-吡喃-4-亚基)-丙烷二腈)。若发射层通过诸如喷墨印刷、辊涂、旋涂等形成，则聚对苯乙炔(PPV)聚合物或聚芴等可用于发射层(5)。
电子传输层(6)处于发射层(5)上。电子传输层(6)要求材料具有自位于其上的阴极(7)的高电子注入效率，并且可有效传输注入的电子。为此，应制备具有高电子亲和性和移动性以及对电子的优异稳定性的材料。此外，电子传输层(6)应与阴极材料形成稳定的界面，否则在运行期间发生阴极层脱层和电子注入无效，将导致电压明显升高。因电子注入无效导致的电压升高使显示器器件效率降低并且能耗增加。此外，已经知道，用具有低工函数的导电金属掺杂到电子传输层，可增强自阴极的电子注入并与金属阴极层形成稳定界面。用于电子传输层的材料包括：芳族化合物如四苯基丁二烯等(日本特开专利公开昭57-51781)；金属配合物如8-羟基喹啉等(日本特开专利公开昭59-194393)；10-羟基苯并[h]喹啉的金属配合物(日本特开专利公开平6-322362)；环戊二烯衍生物(日本特开专利公开平2-289675)；双苯乙烯基苯衍生物(日本特开专利公开平1-245087和日本特开专利公开平2-222484)；苝衍生物(日本特开专利公开平2-189890和日本特开专利公开平3-791)；对亚苯基衍生物(日本特开专利公开平3-33183)；咪唑衍生物(美国专利5,766,779)；和恶唑衍生物(日本特开专利公开平11-345686)等。
阴极(7)位于电子传输层(6)上。阴极(7)  将电子注入电子传输层(6)中。对于用于阴极的材料，优选具有低工函数的金属。特别适用的金属如：锡、镁、铟、钙、钠、锂、铝、银等或其合适的合金。此外，可使用具有双层结构的材料如：氟化锂和铝、氧化锂和铝、氧化锶和铝等。尽管已知铝具有4.2eV的工函数，该电压对于有效电子注入仍不够低，但一薄层绝缘材料通过隧道效应可增强电子注入。此外，可将阴极金属与电子传输层共沉积，由此增强界面强度和电子注入。
位于相反电极之间的四层有机结构，如上所例举的，也可进行变化。加入更多有机层如空穴阻塞层或电子阻塞层可改进有机电致发光器件的性能。此外，使用少于四层的结构可简化器件的结构。
因此，包括本发明上述化学式1至5的有机化合物的至少一层有机化合物层位于阳极和阴极之间。如上所述，在位于阳极和阴极之间的有机化合物层中包含本发明的新材料，优选在电子传输层和发射层中，由此可大大改进有机电致发光器件的效率和器件寿命。此外，提供一种降低操作电压并具有优异稳定性的有机电致发光器件。可将合适的掺杂剂加入本发明使用的材料中，以同时完成电子传输层和发射层的功能，而无单独的发射层。
迄今，具有咪唑基，恶唑基和噻唑基的小分子有机物已频繁报道作为电子注射和传输层的材料。然而，在报道这些材料作为电子传输的材料之前，在EP 0700917 A2(摩托罗拉公司)中已报道了这些材料的金属配合物用于有机电致发光显示器的蓝色发光或蓝-绿色发光层。此外，美国专利5,766,779和5,645,948讨论了有机电致发光显示器，其中将具有咪唑，噻唑或恶唑基的有机材料用于电子传输层和发光层。根据美国专利5,766,779，在用于有机电致发光器件的电子传输层的一个分子中包含2至8个这种杂环官能团。此外，美国专利5,645,948将在一个分子中包含3至8个相同杂环基团的有机材料用于发射层。相反，本发明在9，10-取代蒽部分的2-或2，6-位引入1至2个杂环官能团，用作电子注射、传输和光发射层的材料。
已知由柯达公司在1996引入并在美国专利5,645,948和5,766,779中讨论的TPBI(化学式6)，已用作电子传输和蓝色发射的代表性材料。TPBI具有咪唑基，并且如下面的化学式6所示，它在苯的1，3，5-取代位含三个N-苯基苯并咪唑基，并且完成传输电子或作为发射层的功能。然而，在用于显示器的实际应用中，与本发明要求保护的材料相比，TPBI作为电子传输材料以及发射材料具有较低的操作稳定性，如在本说明书实施例部分中所证明的。
(化学式6)
此外，日本特开专利公开平11-345686讨论了一种用于电子传输的材料，如下化学式7至10所示，其含有恶唑基和噻唑基，并且已报道可用于电致发光层。然而，若付诸实际使用，就显示器的操作电压、亮度和寿命而言并不令人满意。
(化学式7)
Figure S03800155119950507D000102
(化学式8)
(化学式9)
(化学式10)
从现有技术来看，已知除有机金属配合物如Alq3之外的任何有机材料难以实际应用于显示器中。因此，本发明人合成如上化学式1至5所示的新有机材料，选取合适的空穴注入和空穴传输层，以及发射层，然后将其用于电子注入和传输层。因此，在显示器的操作电压、效率和寿命方面可获得更优异的结果。此外，当上述化学式1至5所示的有机材料被用作发射层，与合适选取的空穴注入和空穴传输层以及电子传输层一起，可获得具有显示器优异操作电压和寿命的有机电致发光器件。
本发明人用于新发射层的蒽部分已由美国的柯达公司、TDK公司等进行了研究并在多个专利中进行了揭示，但这种蒽技术的历史起源在二十世纪六十年代早期就已经开始了。Helfrich和Pope首先宣布使用蒽单晶的有机电致发光现象，但在实际使用中，因为发光效率低并且需要高电压，而存在大量问题(W.Helfrich，W.G.Schneider，Phys.Rev.Lett.14，229，1965。M.Pope，H.Kallmann，J.Giachino，J.Chem.Phys.，42，2540，1965)。
因此，为开发具有优异性能的有机电致发光显示器，非常重要的是，在蒽的10个反应/取代位置中的哪个位置引入哪种官能团。柯达公司和TDK公司宣布的大多数蒽衍生物的特征在于仅用于有机电致发光器件的发光层。尽管在日本特开专利公开平11-345686中公开的蒽衍生物声称可用于发光层和电子传输材料，但仅包括在专利的宽权利要求中，而在合成例或实施例中并未提及，并且迄今还没有将其实际用于电子注入和传输材料的例子。
为克服这些问题，本发明人使用蒽的2、6、9、10取代位，而日本特开专利公开平11-345686的特征在于，使用两个取代位置：1和5、1和8、或2和6，而9，10位置为氢原子。
本发明人合成的上述化学式1至5表示的化合物的结构特征如下。蒽具有10个取代位置，本发明人关注的是同时改变蒽的2、6、9、10这四个取代位置，来发现一个最佳的化合物，这是本发明的最重要的特征。具体地，在蒽的9、10位置，用芳烃如：苯基、萘基、联苯基等独立地或同时取代。在2或2、6位置，用咪唑基独立地或同时取代，或先用芳烃如苯基等取代，再由咪唑基独立地或同时取代，由此合成该材料。
当该材料在有机电致发光显示器中用于具有电子传输性能的层时，可同时改进显示器的操作电压和寿命。代表性材料将在下面的实施例中更详细地解释。本发明具有电子传输和发射性能的代表性材料为具有如下化学式1-1至1-10，化学式2-1至2-5，化学式3-1至3-5，化学式4-1至4-5和化学式5-1至5-5的化合物。
(化学式1-1)                                    (化学式1-2)
Figure S03800155119950507D000121
(化学式1-3)                                             (化学式1-4)
(化学式1-5)
Figure S03800155119950507D000132
(化学式1-6)
(化学式1-7)
Figure S03800155119950507D000141
(化学式1-8)
(化学式1-9)
Figure S03800155119950507D000143
(化学式1-10)
Figure S03800155119950507D000151
(化学式2-1)
Figure S03800155119950507D000152
(化学式2-2)
(化学式2-3)
(化学式2-4)
(化学式2-5)
(化学式3-1)                                     (化学式3-2)
Figure S03800155119950507D000172
(化学式3-3)                                      (化学式3-4)
Figure S03800155119950507D000173
(化学式3-5)
(化学式4-1)
(化学式4-2)
Figure S03800155119950507D000183
(化学式4-3)
(化学式4-4)
Figure S03800155119950507D000192
(化学式4-5)
Figure S03800155119950507D000193
(化学式5-1)
Figure S03800155119950507D000201
(化学式5-2)
(化学式5-3)
(化学式5-4)
Figure S03800155119950507D000211
(化学式5-5)
给出上述化合物以有助于理解本发明，但本发明提供的化合物不限于这些。例如咪唑基的芳烃部分可被基团，如：C1-C20烷基，烷氧基或芳烃，取代或未取代的杂环或芳基，或卤素如：Cl、Br、F或I所取代。此外，咪唑基可在苯环上具有一个以上的取代，并且此取代可具有邻位、间位或对位取代。即咪唑基可按照下式取代：
其中R5可为C1-C20烷基，烷氧基或芳烃，芳基取代的硅基，芳基取代的硼基，取代或未取代的杂环或芳基，或卤素如：Cl、Br、F或I。
此外，蒽部分可进一步被其他的基团取代，如下所示：
其中R6可为C1-C20烷基，烷氧基或芳烃，取代或未取代的杂环或芳基，或卤素如：Cl、Br、F或I。
下面参考实施例和对比例更为详细地说明合成满足上述化学式1、2、3、4和5的化合物和使用这些化合物的有机电致发光显示器。然而，这些是用于说明本发明的，本发明不受它们限制，实施例中未描述的但满足上述化学式1、2、3、4和5的化合物也在本发明范围内，它们可用作有机电致发光显示器的有机化合物层。
实施例：
为合成上述化学式1至5表示的化合物，原料选自如下化学式a至i的化合物，其制备描述于下面的制备例1至9中。
(化学式a)                                  (化学式b)                              (化学式c)
(化学式d)                                  (化学式e)                               (化学式f)
Figure S03800155119950507D000232
(化学式g)                                   (化学式h)                               (化学式i)
Figure S03800155119950507D000233
(化学式j)                                                            (化学式k)
Figure S03800155119950507D000241
(化学式1)
制备例1
(制备化学式a表示的原料)
将2，6-二氨基蒽醌(23.8g，100mmol)分散于48wt％溴化氢水溶液中，然后在20℃下慢慢加入亚硝酸钠(NaNO2，14.1g，204mmol)。气体完全放出后，将溴化铜(CuBr，29.5g，206mmol)溶于48wt％溴化氢水溶液中(63mL)，将该溶液与少量乙醇(50mL)一起慢慢加入。将反应混合物的温度慢慢升高，使该混合物慢慢回流。冷却至室温后，加入水稀释该混合物，并抽滤得到沉淀物，用水洗涤，并真空干燥。然后将其溶于氯仿中，通过一个短的硅胶柱子过滤，并在减压下浓缩。通过柱色谱纯化并用氯仿重结晶，得到化学式a的化合物(10.0g，27％)。
该化合物的分析结果如下。
1H NMR(300MHz，CDCl3)，8.44(d，J＝2.1Hz，2H)，8.18(d，J＝8.0Hz，2H)，7.95(dd，J＝2.1，8.0Hz，2H)
制备例2
(制备化学式b表示的原料)
将2-溴联苯(8.83mL，51.2mmol)在氮气气氛下溶于干燥的THF(200mL)中并冷却至-78℃，然后慢慢加入叔丁基锂(60mL，1.7M戊烷溶液)。在相同温度下搅拌40分钟后，加入制备例1中制备的化学式a的化合物(7.50g，20.5mmol)。除去冷却浴，并将混合物在室温下搅拌15小时。然后将其用乙醚(200mL)和2N盐酸(200mL)骤冷，并在室温下搅拌40分钟。抽滤出沉淀物，并用水和乙醚洗涤。将获得的物质干燥，由此获得化学式b的化合物(11.8g，85％)。
制备例3
(制备化学式表示的原料c)
将制备例2中制备的化学式b的化合物(4.00g，5.93mmol)，碘化钾(9.85g，59.3mmol)和次磷酸钠水合物(10.4g，98.0mmol)的混合物在乙酸(80mL)和邻-二氯苯(600mL)的混合物中回流。冷却至室温后，将该反应混合物用氯仿萃取，在硫酸镁上干燥，并在减压下浓缩。将获得的固体溶于氯仿中，通过一个短的硅胶柱，并在减压下浓缩。将固体分散于正己烷中，搅动并过滤，然后真空干燥，获得化学式c的浅黄色化合物(3.30g，87％)。
该化合物的分析结果如下：
m.p.478.1℃；1H NMR(300MHz，CDCl3)7.92(d，J＝7.6Hz，4H)，7.46(t，J＝8.0Hz，4H)，7.33(t，J＝7.4Hz，4H)，7.21(d，J＝7.6Hz，4H)，6.88(dd，J＝2.1，8.6Hz，2H)，6.47(d，J＝2.1Hz，2H)，6.22(d，J＝8.6Hz，2H)；MS(M+)636；分析计算为C38H22Br2：C，71.50；H，3.47；Br，25.03。测定值：C，71.90；H，3.40；Br，25.7。
制备例4
(制备化学式d表示的原料)
将溴化铜(CuBr2，17.9g，80.0mmol)和叔丁腈(12mL，101mmol)在65℃下分散于乙腈(250mL)中并搅拌，然后在5分钟内慢慢滴加入2-氨基蒽醌(15.0g，67.2mmol)。气体完全放出后，将该混合物冷却至室温，用20％盐酸(1,000mL)骤冷，并用二氯甲烷萃取。将该有机萃取物在硫酸镁上干燥并在减压下浓缩。通过柱色谱纯化(二氯甲烷/正己烷＝4/1)，得到化学式d的化合物(14.5g，75％)。
该化合物的分析结果如下：
m.p.207.5C；1H NMR(500MHz，CDCl3)，8.43(d，J＝1.8Hz，1H)，8.30(m，2H)，8.17(d，J＝8.3Hz，1H)，7.91(dd，J＝1.8，8.3Hz，1H)，7.82(m，2H)；MS(M+)286；分析计算为C14H7BrO2：C，58.57；H，2.46；Br，27.83；O，11.14。测定值：C，58.88；H，2.39；Br，27.80；O，10.93。
制备例5
(制备化学式e表示的原料)
将2-溴联苯(9.0mL，52mmol)在氮气气氛下溶于干燥的四氢呋喃(100mL)中，并在-78℃下慢慢加入叔丁基锂(40mL，1.7M戊烷溶液)。在相同温度下搅拌1小时后，加入制备例4中制备的化学式d的化合物(4.9g，17mmol)。将氯化铵水溶液加入该混合物中，然后将其用二氯甲烷萃取。将该有机萃取物在硫酸镁上干燥，并在减压下浓缩。将获得的固体分散于乙醇中，搅拌1小时，抽滤，并用乙醇洗涤。干燥后，获得化学式e的化合物(9.50g，94％)。
制备例6
(制备化学式表示的原料f)
将制备例5中制备的化学式e的化合物(6.00g，10.1mmol)在氮气气氛下分散于300mL乙酸中，然后加入碘化钾(16.8g，101mmol)和次磷酸钠水合物(17.7g，167mmol)，并将该混合物在沸腾状态下搅拌3小时。冷却至室温后，将该混合物过滤并用水和甲醇洗涤，然后真空干燥，获得化学式f的浅黄色化合物(5.0g，88％)。
制备例7
(制备化学式表示的原料g)
将制备例5中制备的化学式e的化合物(9.5g，16mmol)在分散于100mL乙酸中，并向其中滴加入5滴浓硫酸，然后将该混合物回流3小时。将该混合物冷却至室温，并将沉淀物过滤，用乙酸洗涤，然后用水和乙醇顺序洗涤。干燥后，将固体通过升华纯，获得化学式g的白色固体化合物(8.0g，89％)。
制备例8
(制备化学式表示的原料h)
将制备例7中制备的化学式g的化合物(10.0g，17.9mmol)在氮气气氛下彻底溶于150mL干燥THF中，然后在-78℃下慢慢加入叔丁基锂(31.5mL，1.7M戊烷溶液)。在相同温度下搅拌1小时后，加入硼酸三甲酯(8mL，71.5mmol)。除去冷却浴，并将反应混合物在室温下搅拌3小时。然后将其用2N盐酸溶液(100mL)骤冷，并在室温下搅拌1.5小时。将沉淀物过滤，并用水和乙醚顺序洗涤，真空干燥。干燥后，将粗产品分散于乙醚中，搅拌2小时，过滤，并干燥获得化学式h的白色化合物(7.6g，81％)。
制备例9
(制备化学式表示的原料i)
将2-溴萘(11.0g，53.1mmol)在氮气气氛下溶于干燥的四氢呋喃(100mL)中，然后在-78℃下慢慢加入叔丁基锂(47.0mL，1.7M戊烷溶液)。在相同温度下搅拌1小时后，加入制备例4中制备的化学式d的化合物(6.31g，22.0mmol)。除去冷却浴，并将反应混合物在室温下搅拌3小时。将氯化铵水溶液加入该混合物中后，将反应混合物用二氯甲烷萃取。将该有机萃取物在硫酸镁上干燥，并在减压下浓缩。将获得的粗产品分散于乙醚中，然后加入石油醚，并将该混合物搅拌数小时获得固体化合物。将该固体过滤并真空干燥，获得二萘基二醇(11.2g，94％)。将上面合成的二萘基二醇(11.2g，20.6mmol)在氮气气氛下分散于600mL乙酸中，然后加入碘化钾(34.2g，206mmol)和次磷酸钠水合物(36.0g，340mmol)。并将该混合物在沸腾状态下搅拌3小时。冷却至室温后，将该混合物过滤并用水和甲醇洗涤，然后真空干燥，获得化学式i的浅黄色化合物(10.1g，96％)。
实施例1
(制备化学式2-2表示的化合物)
将4-溴苯甲醛(41.6g，225mmol)和1，3-丙二醇(16.3mL，225mmol)溶于500mL甲苯中，然后加入1g对甲苯磺酸，并将该混合物回流2天，同时除去水。将100mL乙醚加入该混合物中将其稀释，并将其用100mL水骤冷。将该有机萃取物在硫酸镁上干燥，并在减压下浓缩。通过柱色谱纯化，并用石油醚结晶，得到4-溴苯乙醛(45.0g，82％)，为白色固体。
向4-溴苯乙醛(5.00g，20.6mmol)在干燥THF(100mL)中的溶液中在-78℃下滴加入叔丁基锂(24.2mL，1.7M戊烷溶液)。将该混合物搅拌1小时后，在-78℃下慢慢加入硼酸三甲酯(trimethylborate)(7mL，62.4mmol)，然后将反应温度慢慢升高并将该混合物在室温下搅拌3小时。
将该反应混合物倒入200mL，2N盐酸中，搅拌1小时，过滤，用水和乙醚洗涤，并干燥获得白色4-甲酰基苯基硼酸(4-formylphenylboronic)(2.50g，81％)。
然后将制备例3中制备的化学式c的化合物(0.40g，0.62mmol)和4-甲酰基苯基硼酸(1.10g，7.34mmol)加入到含有10mL 2N碳酸钾溶液和30mL甲苯的溶液中，并在搅拌下加入Pd(PPh3)4(0.16g，0.14mmol)，将该混合物回流3天。将有机层分离，用水洗涤，在硫酸镁上干燥，通过一个硅胶柱，并在减压下浓缩。将粗产品分散于40mL乙醇中，过滤，并用氯仿重结晶，获得二醛(155mg，36％)。
将二醛(120mg，0.17mmol)和N-苯基-1，2-苯二胺(83mg，0.45mmol)加入含有20ml甲苯和10ml乙酸的溶液中。将该混合物回流2天，冷却至室温，抽滤，并用乙醇洗涤。将获得的固体用100ml氯仿洗涤，并干燥，获得化学式2-2表示的纯化合物(120mg，68％)。
该化合物的分析结果如下：
m.p.395.0℃；1H NMR(300MHz，CDCl3)7.88(2H)，7.62(2H)，7.66-7.60(10H)，7.55-7.44(15H)，7.40(2H)，7.38-30(9H)，6.95(6H)，6.83(4H)；MS[M+H]1019。
实施例2
(制备化学式1-2表示的化合物)
将制备例6中制备的化学式f表示的化合物(1.00g，1.80mmol)和4-甲酰基苯基硼酸(0.74g，4.93mmol)加入含有20mL 2N碳酸钾溶液和40mL甲苯的溶液中，并在搅拌下加入Pd(PPh3)4(0.20g，0.17mmol)，将该混合物回流3天。将有机层分离，用水洗涤，在硫酸镁上干燥，通过一个硅胶层，并在减压下浓缩，获得固体化合物。将该固分散于100mL乙醇中，过滤，并用乙酸乙酯重结晶，获得蒽苯甲醛(330mg，31％)。
将蒽苯甲醛(0.33g，0.56mmol)和N-苯基-1，2-苯二胺(0.11g，0.60mmol)的混合物在40mL甲苯和10mL乙酸的混合溶液中回流2天。冷却至室温后，将沉淀物过滤，用乙醇和氯仿洗涤，并干燥，获得化学式1-2的化合物(120mg，28％)。
该化合物的分析结果如下：
1H NMR(300MHz，CDCl3)7.89(1H)，7.75(1H)，7.62-7.29(24H)，6.98-6.76(12H)；MS[M+H]751。
实施例3
(制备化学式1-4表示的化合物)
将制备例9中制备的化学式i表示的化合物(4.00g，7.85mmol)和4-甲酰基苯基硼酸(3.53g，23.5mmol)加入20mL 2N碳酸钾溶液和60mL甲苯的溶液中，并在搅拌下加入Pd(PPh3)4(0.27g，0.23mmol)，将该混合物回流3天。将有机层分离，用水洗涤，在硫酸镁上干燥，通过硅胶层，并浓缩获得固体化合物。将该固分散于100mL乙醇中，过滤，并用乙酸乙酯重结晶，获得蒽苯甲醛(2.00g，47.6％)。
将蒽苯甲醛(2.00g，3.74mmol)和N-苯基-1，2-苯二胺(0.69g，3.74mmol)的混合物在40mL甲苯和10mL乙酸的混合物中回流2天。冷却至室温后，将形成的固体过滤，用乙醇和氯仿洗涤，并干燥获得化学式1-4的化合物(1.30g，49.7％)。
该化合物的分析结果如下：
m.p.352.0℃；1H NMR(300MHz，CDCl3)8.28(s，2H)，8.14(d，2H)，7.99(t，4H)，7.81(t，4H)，7.62(m，4H)，7.53(d，2H)，7.45(m，4H)，7.32-7.26(m，6H)，7.22(s，6H)；MS[M+H]699。
实施例4
(制备化学式2-4表示的化合物)
将2-溴萘(5.78g，28.0mmol)溶于干燥的THF(40mL)中，在-78℃，氮气气氛下向溶液中滴加冷的叔丁基锂(21mL，1.7M戊烷溶液)。在相同温度下搅拌40分钟后，在该温度下加入制备例1中制备的化学式a的化合物(2.93g，8.00mmol)。移去冷却浴，并将混合物在室温下搅拌3小时。将氯化铵溶液(40mL)慢慢加入该反应混合物中，并将该混合物在室温下搅拌40min。将沉淀物抽滤、用水和石油醚洗涤、并干燥获得二醇(4.10g，82％)。
将该二醇(4.10g，6.59mmol)，碘化钾(10.9g，65.9mmol)，和次磷酸钠水合物(11.6g，109mmol)的混合物在乙酸(200mL)中回流24小时。将该混合物冷却至室温，过滤，用水和石油醚顺序洗涤，并干燥获得2，6-二溴-9，10-二萘-2-基-蒽(3.15g，81％)。
将2，6-二溴-9，10-二萘-2-基-蒽(3.15g，5.35mmol)和4-甲酰基苯基硼酸(2.81g，18.7mmol)加入含有20mL 2N碳酸钾溶液和100mL甲苯的溶液中，并在搅拌下加入Pd(PPh3)4(0.25g，0.22mmol)，将该混合物回流15小时。将有机层分离，用水洗涤，在硫酸镁上干燥，通过柱色谱纯化，得到二萘基蒽苯二醛(2.77g，81％)。
将二萘基蒽苯二醛(2.77g，4.34mmol)和N-苯基-1，2-苯二胺(2.00g，10.9mmol)的混合物在120mL甲苯和60mL乙酸的混合物中回流15小时，加入氧化锰(1.51g，17.4mmol)，并将该混合物进一步反应2小时。冷却至室温后，将形成的固体过滤，用乙醇和氯仿洗涤，并干燥获得化学式2-4的化合物(1.52g，36％)。
实施例5
(制备化学式3-2表示的化合物)
将9，10-二氧代-9，10-二氢-蒽-2-甲醛(carbaldehyde)(1.63g，6.9mmol)和N-苯基-1，2-苯二胺(1.27g，6.90mmol)的混合物加入80mL甲苯和10mL乙酸的混合物中，并将该混合物回流12小时，除去溶剂，并将乙醇倒入其中使其结晶，然后将沉淀物过滤获得苯并咪唑化合物([2-(1-苯基-1H-苯并咪唑-2-基)-蒽醌]，1.14g，41％)。
在78℃下，向2-溴联苯(1.1mL，6.25mmol)在干燥四氢呋喃(50mL)的溶液中滴加入叔丁基锂(8.3mL，1.5M戊烷溶液)。在相同温度下搅拌30分钟后，将上面合成的2-(1-苯基-1H-苯并咪唑-2-基)-蒽醌(1.00g，2.50mmol)慢慢加入该混合物中，然后将该混合物在室温下搅4小时。接着将其倒入2N盐酸和乙醚的混合物中，并搅拌1小时。将沉淀物过滤并干燥获得9，10-双[联苯-2-基-(1-苯基-1H-苯并咪唑-2-基)]-9，10-二氢-蒽-9，10-二醇(1.00g，57％)。
将该二醇(0.70g，1.00mmol)在氮气气氛下分散于60mL乙酸中，并加入碘化钾(1.66g，10mmol)和次磷酸钠水合物(1.66g，15.7mmol)，然后将该混合物在沸腾状态下搅拌。将该混合物冷却至室温，过滤，用水和甲醇洗涤，并干燥获得化学式3-2的浅黄色化合物(0.45g，67％)。
该化合物的分析结果如下：
m.p.270.0℃；1H NMR(300MHz，CDCl3)7.86(d，1H)，7.75(dd，1H)，7.70(s，1H)，7.63-7.48(m，8H)，7.42-7.0(m，12H)，6.92-6.81(m，9H)，6.63(d，2H)；MS[M+H]675。
实施例6
(制造有机电致发光器件)
在玻璃基材上涂布厚度为1,500
Figure S03800155119950507D000321
的ITO(氧化铟锡)薄膜，将其放入溶有洗涤剂的蒸馏水中，并用超声波洗涤。其中洗涤剂，使用Fischer公司的产品，并将该蒸馏水用购自Millipore公司的过滤器过滤两次。将ITO洗涤30分钟，然后在蒸馏水中相继进行两次超声洗涤，每次10分钟。用蒸馏水洗涤后，用溶剂如：异丙醇、丙酮、甲醇等进行超声洗涤，将该基材干燥并转移入等离子体清洗仪器中。然后将该甲醇用等离子体清洗5分钟，并转移到等离体清洗仪器中。然后将该基材用氧等离子体清洗5分钟，并转移到真空沉积仪器中。
在制备的ITO透明电极上，真空热沉积厚度为500
Figure S03800155119950507D000331
的己腈六氮杂三亚苯基(hexanitrile hexaazatriphenylene)以形成空隙注入层。将传输空穴的NPB真空沉积于其上(600)，并真空沉积厚度为300
Figure S03800155119950507D000333
的Alq3作为发射层。将完成注入和传输电子功能的化学式1-4的化合物以200
Figure S03800155119950507D000334
的厚度真空沉积在该发射层上，形成有机材料层薄膜。在电子注入和传输层上，用遮光板加工6mm2的试验像素顺序沉积厚度5
Figure S03800155119950507D000335
的氟化锂和厚度为2500的铝形成阴极。有机材料的沉积速率保持1
Figure S03800155119950507D000337
/sec，氟化锂的沉积速率为0.2/sec，铝的沉积速率为3-7/sec。
在该制备的有机电致发光器件上，加上一前向的5.4V电场，结果在电流密度50mA/cm2下观察到具有亮度1,656nit的绿色光谱，基于1,931CIE色品坐标，相当于x＝0.34，y＝0.55。
通过施加200mA/cm2恒定DC电流密度测量器件的半衰期。监测亮度和驱动电压的变化，对比已有的化合物以评估要求保护的化合物的性能。如图2所示，驱动40小时后，器件的亮度降至53％，驱动电压升至6.4V，相当于初始驱动电压的102％(参见图5)。
对比例1
(制造有机电致发光器件)
在实施例6制备的ITO透明电极上，真空热沉积厚度为500
Figure S03800155119950507D0003310
的己腈六氮杂三亚苯基以形成空穴注入层。将传输空穴的NPB真空沉积于其上(600
Figure S03800155119950507D0003311
)，并真空沉积厚度500
Figure S03800155119950507D0003312
的同时完成发射和电子传输功能的Alq3。在Alq3层上，用遮光板加工6mm2的试验像素顺序沉积厚度5的氟化锂(LiF)和厚度为2500的铝形成阴极。有机材料的沉积速率保持在1
Figure S03800155119950507D000343
/sec，即氟化锂的沉积速率为0.2
Figure S03800155119950507D000344
/sec，铝的沉积速率为3-7/sec。
在制备的有机电致发光器件上，加上一前向的6.4V电场，结果在电流密度50mA/cm2下观察到具有亮度1,774nit的绿色光谱，基于1,931CIE色品坐标，相当于x＝0.34，y＝0.56。此结果说明，加入本发明的电子传输层可降低驱动电压，如实施例6所示。
通过施加200mA/cm2恒定DC电流密度测量器件的半衰期。如图3所示，驱动38小时后，器件的亮度降至50％，驱动电压升至7.7V，相当于初始驱动电压的102％(参见图5)。
对比例2
(制造有机电致发光器件)
在实施例6制备的ITO透明电极上，真空热沉积厚度500
Figure S03800155119950507D000347
的己腈六氮杂三亚苯基以形成空隙注入层。将传输空穴的NPB真空沉积于其上(600)，并真空沉积厚度300的完成发射层功能的Alq3。在该发射层上，真空沉积厚度200的完成注入和传输电子功能的TPBI，由此形成有机材料层薄薄膜。在该电子传输层上，用遮光板加工6mm2的试验像素顺序沉积厚度5
Figure S03800155119950507D0003411
的氟化锂(LiF)和厚度2500A的铝形成阴极。有机材料的沉积速率保持1/sec，即氟化锂的速率为0.2/sec，铝的速率为3-7
Figure S03800155119950507D000353
/sec。
在制备的有机电致发光器件上，加上一前向的5.5V电场，结果在电流密度50mA/cm2下观察到具有亮度1,665nit的绿色光谱，基于1,931CIE色品坐标，相当于x＝0.34，y＝0.56。
通过施加200mA/cm2恒定DC电流密度测量器件的半衰期。如图4所示，驱动40小时后，器件的亮度降至50％水平，驱动电压升至7.2V，相当于初始驱动电压的113％(参见图5)。此对比结果说明，本发明的电子传输材料提供在操作期间可将驱动电压的升高最小化的有机电致发光器件。
实施例7
(制造有机电致发光器件)
进行下面的实验以测试本发明化合物作为发射材料对空穴载流子的稳定性，在该材料中，空穴和电子再结合而发光。在发射层中使用p-型发射材料(空穴迁移性能＞电子迁移性能)或合适量的p-型掺杂剂时，空穴载流子可转移入电子传输层中。因此，若包括电子传输层的材料对空穴不稳定，则器件容易被破坏，不是因为发射材料而是因为电子传输材料的不稳定性。
在实施例6中制备的ITO透明电极上，真空热沉积厚度为500
Figure S03800155119950507D000354
的己腈六氮杂三亚苯基以形成空隙注入层。将用于传输空穴的NPB真空沉积于其上(600)，并真空沉积厚度为400的作为发射层的化学式1-4的化合物。在该发射层上，真空沉积厚度为200
Figure S03800155119950507D000357
的用作电子注入和传输功能的Alq3，由此形成一薄层有机材料层。在该电子传输层上，用遮光板加工6mm2的试验像素顺序沉积厚度5
Figure S03800155119950507D000358
的氟化锂和厚度为2500的铝形成阴极。有机材料的沉积速率保持1
Figure S03800155119950507D0003510
/sec，氟化锂的沉积速率为0.2
Figure S03800155119950507D0003511
/sec，铝的沉积速率为3-7/sec。
在制备的有机电致发光器件上，加上一前向的6.6V电场，结果在电流密度50mA/cm2下观察到具有亮度733nit(最大峰位于460nm处)的蓝色光。
通过施加50mA/cm2恒定DC电流密度测量器件的半衰期。如图6所示，驱动140小时后，器件的亮度降至67％，驱动电压升至6.5V，相当于初始驱动电压的103％(参见图7)。此结果说明，本专利申请要求保护的材料对空穴载流子稳定，并且可用作具有增强器件寿命的蓝色发射源。
对比例3
(制备有机电致发光器件)
按与实施例6相同的方式制备电致发光器件，不同的是，将TPBI用作发射材料代替化学式1-4的化合物。
在制备的有机电致发光器件上，加上一向前的6.9V电场，结果在电流密度50mA/cm2下观察到具有亮度354nit(最大峰位于440nm处)的蓝色光。
通过施加50mA/cm2恒定DC电流密度测量器件的半衰期。如图6所示，驱动20小时后，器件的亮度降至20％水平，驱动电压升至8.2V，相当于初始驱动电压的124％(参见图7)。此对比结果说明，本发明的材料对空穴载流子稳定，并且可用作具有增强器件寿命的蓝色发射源。
实施例8
(制造有机电致发光器件)
在实施例6中制备的ITO透明电极上，真空热沉积厚度500
Figure S03800155119950507D000361
的己腈六氮杂三亚苯基以形成空隙注入层。将用于传输空穴的NPB真空沉积于其上(600
Figure S03800155119950507D000362
)，并真空沉积厚度为100的作为发射层的化学式j表示的化合物。在该发射层上，真空沉积厚度200的用作注入和传输电子功能的化学式1-2表示的化合物，由此形成一薄层有机材料层。在该电子注入和传输层上，用遮光板加工6mm2的试验像素顺序沉积厚度为5
Figure S03800155119950507D000365
的氟化锂(LiF)和厚度为2,500的铝形成阴极。有机材料的沉积速率保持1/sec，氟化锂的沉积速率为0.2/sec，铝的沉积速率为3-7
Figure S03800155119950507D000374
/sec。
在制备的有机电致发光器件上，加上一前向的4.04V电场，结果在电流密度10mA/cm2下观察到具有亮度184nit的蓝色光谱，基于1,931CIE色品坐标，相当于x＝0.16，y＝0.11。
实施例9
(制造有机电致发光器件)
在实施例6中制备的ITO透明电极上，真空热沉积厚度为500
Figure S03800155119950507D000375
的己腈六氮杂三亚苯基以形成空隙注入层。将用于传输空穴的NPB真空沉积于其上(600
Figure S03800155119950507D000376
)，然后真空沉积厚度为200
Figure S03800155119950507D000377
的用作发射层的化学式1表示的化合物。在该发射层上，真空沉积厚度200
Figure S03800155119950507D000378
的用作注入和传输电子功能的化学式2-2表示的化合物，由此形成一薄层有机材料层。在该电子注入和传输层上，用遮光板加工6mm2的试验像素顺序沉积厚度为5
Figure S03800155119950507D000379
的氟化锂(LiF)和厚度为2,500
Figure S03800155119950507D0003710
的铝形成阴极。有机材料的沉积速率保持在1
Figure S03800155119950507D0003711
/sec，氟化锂的沉积速率为0.2/sec，铝的沉积速率为3-7
Figure S03800155119950507D0003713
/sec。
在制备的有机电致发光器件上，加上一前向的4.63V电场，结果在电流密度10mA/cm2下观察到具有亮度226nit的蓝色光谱，基于1,931CIE色品坐标，相当于x＝0.16，y＝0.19。
实施例10
(制备有机电致发光器件)
在实施例6中制备的ITO透明电极上，真空热沉积厚度为500的己腈六氮杂三亚苯基以形成空隙注入层。将用于传输空穴的NPB真空沉积于其上(600)，然后真空沉积厚度为200的作为发射层的化学式k表示的化合物。在该发射层上，真空沉积厚度200的用作注入和传输电子功能的化学式3-2表示的化合物。在该电子注入和传输层上，用遮光板加工6mm2的试验像素顺序沉积厚度为5的氟化锂(LiF)和厚度为2,500的铝形成阴极。有机材料的沉积速率保持1/sec，氟化锂的沉积速率为0.2
Figure S03800155119950507D000384
/sec，铝的沉积速率为3-7/sec。
在制备的有机电致发光器件上，加上一前向的5.17V电场，结果在电流密度10mA/cm2下观察到具有亮度124nit的蓝色光谱，基于1,931CIE色品坐标，相当于x＝0.16，y＝0.12。
本发明的新材料可包含于有机电致发光显示器的有机化合物层中以实现对发光、效率和寿命以及低操作电压的改进。
应理解上面的描述和这里给出的具体实施方案仅用于说明本发明的最佳实施方式和其原理，本领域熟练技术人员可容易地在不离开本发明精神和范围下进行改性和添加，因此应理解本发明的精神和范围仅受所附权利要求的限制。

Claims (17)

1.化学式1表示的化合物：
Figure FFW00000041592800011
其中：
R1和R2各自独立地或同时为苯基、萘基、联苯基或蒽基；
Ar为苯环；
R3为氢原子；
R4为氢原子、苯基、萘基、联苯基或蒽基；和
R5为氢原子。
2.化学式2表示的化合物：
Figure FFW00000041592800012
其中：
R1和R2各自独立地或同时为苯基、萘基、联苯基或蒽基；
Ar为苯环；
R4为氢原子、苯基、萘基、联苯基或蒽基；和
R5为氢原子。
3.化学式3表示的化合物：
其中：
R1和R2各自独立地或同时为苯基、萘基、联苯基或蒽基；
R3为氢原子；
R4为氢原子、苯基、萘基、联苯基或蒽基；和
R5为氢原子。
4.化学式4表示的化合物：
Figure FFW00000041592800022
其中：
R1和R2各自独立地或同时为苯基、萘基、联苯基或蒽基；
R4为氢原子、苯基、萘基、联苯基或蒽基；和
R5为氢原子。
5.化学式5表示的化合物：
其中：
R1和R2各自独立地或同时为苯基、萘基、联苯基或蒽基；
Ar为苯环；
R4为氢原子、苯基、萘基、联苯基、蒽基；和
R5为氢原子。
6.一种有机电致发光显示器，包括：
至少一层有机层，该层包括选自由化学式1表示的化合物、化学式2表示的化合物、化学式3表示的化合物、化学式4表示的化合物和化学式5表示的化合物所组成的组中至少一种化合物： 
Figure FFW00000041592800041
Figure FFW00000041592800051
其中在上面的化学式1、2、3、4和5中，
R1和R2各自独立地或同时为苯基、萘基、联苯基或蒽基；
Ar为苯环；
R3为氢原子；
R4为氢原子、苯基、萘基、联苯基或蒽基；和
R5为氢原子。
7.根据权利要求6的有机电致发光显示器，其中至少一层有机层处于注入空穴的阳极与注入电子的阴极之间。
8.根据权利要求6的有机电致发光显示器，其中至少一层有机层为完成电子注入和传输功能的电子注入/传输层。
9.根据权利要求6的有机电致发光显示器，其中至少一层有机层为完成电子注入和发光功能的电子注入/传输和发射层。
10.根据权利要求6的有机电致发光显示器，其中至少一层有机层为完成光发射功能的发射层。
11.根据权利要求6的有机电致发光显示器，其中至少一层有机层为完成电子传输和光发射功能的电子传输和发射层。 
12.根据权利要求6的有机电致发光显示器，其中有机电致发光显示器包括基材、在基材上的阳极、在阳极上的空穴注入层、在空穴注入层上的空穴传输层、在空穴传输层上的发射层、在发射层上的电子传输层和在电子传输层上的阴极；并且有机化合物至少包含在发射层中。
13.根据权利要求6的有机电致发光显示器，其中有机电致发光显示器包括基材、在基材上的阳极、在阳极上的空穴注入层、在空穴注入层上的空穴传输层、在空穴传输层上的发射层、在发射层上的电子注入/传输层和在电子注入/传输层上的阴极；并且有机化合物至少包含在电子注入/传输层中。
14.根据权利要求6的有机电致发光显示器，其中有机化合物层包括化学式1或化学式3的化合物。
15.根据权利要求6的有机电致发光显示器，其中化学式1表示的化合物为选自如下化学式1-2和1-4中的至少一种化合物：
Figure FFW00000041592800061
。
16.根据权利要求6的有机电致发光显示器，其中化学式2表示的化合物由如下化学式2-2表示：
17.根据权利要求6的有机电致发光显示器，其中化学式3表示的化合物为化学式3-2表示的化合物：
Figure FFW00000041592800072
。
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US6878469B2 (en) 2005-04-12
AU2003215914A8 (en) 2003-07-30
CN1625552A (zh) 2005-06-08
EP1465874A2 (en) 2004-10-13
KR20030067773A (ko) 2003-08-19
EP1465874B1 (en) 2013-06-19
JP2005515233A (ja) 2005-05-26
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