CN112110900A - 一种有机电致化合物及其使用该化合物的有机发光器件 - Google Patents

一种有机电致化合物及其使用该化合物的有机发光器件 Download PDF

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CN112110900A
CN112110900A CN202010939958.2A CN202010939958A CN112110900A CN 112110900 A CN112110900 A CN 112110900A CN 202010939958 A CN202010939958 A CN 202010939958A CN 112110900 A CN112110900 A CN 112110900A
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organic electroluminescent
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郑贤哲
张海龙
高春吉
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Zhejiang Huadisplay Optoelectronics Co Ltd
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Abstract

本发明涉及一种有机电致化合物和使用该化合物的有机发光管器件，更具体而言，涉及一种具有优异的色纯度和高亮度及发光效率的可溶性磷光主体化合物以及使用该化合物的OLED器件。本发明提供下式1之一的有机电致化合物：

Description

一种有机电致化合物及其使用该化合物的有机发光器件
技术领域
本发明属于有机电致发光领域，尤其涉及一种有机电致化合物和使用该化合物的有机发光管器件。
背景技术
随着多媒体技术的发展及信息化要求的提高，对面板显示器性能的要求越来越高。其中，OLED具有自主发光、低电压直流驱动、全固化、视角宽、颜色丰富等一系列的优点，在新一代显示器和照明技术中的潜在应用而引起广泛注意，应用前景十分广阔。
有机电致发光器件技术既可以用来制造新型显示产品，也可以用于制作新型照明产品，也可以应用于液晶显示和荧光灯照明，应用前景十分广泛。有机电致发光器件是自发的发光器件，OLED发光的机理是在外加电场作用下，电子和空穴分别从正负两极注入后在有机材料中迁移、复合并衰减而产生发光。OLED的典型结构包括阴极层、阳极层、电子注入层、电子传输层、空穴阻挡层、空穴传输层、空穴注入层和有机发光层中的一种或几种功能层。
尽管有机电致发光的研究进展非常迅速，但仍有很多亟待解决的问题，比如外量子效率(EQE)的提高，色纯度更高的新材料的设计与合成、高效电子传输/空穴阻挡新材料的设计与合成等。对于有机电致发光器件来说，器件的发光量子效率是各种因素的综合反映，也是衡量器件品质的一个重要指标。
发光原理可以分为荧光发光和磷光发光。在荧光发光中，单线态激发状态的有机分子跃迁至基态，由此发出光。另一方面，在磷光发光中，三线态激发状态的有机分子跃迁至基态，由此发出光。
当发光材料层发射对应于能带隙的光时，具有0自旋的单线态激子和具有1自旋的三线态激子以1:3的比例产生。有机材料的基态为单线态，这使单线态激子可以跃迁至基态并伴随发光。但是，由于三线态激子不能发生伴随发光的跃迁，因此使用荧光材料的OLED器件的内量子效率被限制在25％以内。
另一方面，如果自旋轨道耦合动量很高，则单线态和三线态混合以使得在单线态和三线态之间产生系间跨越，并且三线态激子也可以跃迁至基态并伴随发光。磷光材料可以使用三线态激子和单线态激子，以使得使用磷光材料的OLED器件可以具有100％的内量子效率。
近来，已将铱络合物，例如双(2-苯基喹啉)(乙酰丙酮)铱(Ⅲ)(Ir(2-phq)2(acac))、双(2-苯并[b]噻吩-2-基吡啶)(乙酰丙酮)铱(Ⅲ)(Ir(btp)2(acac))和三(2-苯基喹啉)铱(Ⅲ)Ir(2-phq)3掺杂剂引入。
为了利用磷光材料获得高电流发光效率(Cd/A),需要优异的内部量子效率、高的色纯度和长寿命。特别是，参照图1，色纯度越高，即，CIE(X)越高，颜色灵敏度越差。结果，在高内量子效率下，非常难获得发光效率。因此，需要具有优异色纯度(CIE(X)≥0.65)和高发光效率的新型有机电致化合物。
另一方面，除了上述的铱络合物之外，例如，4,4-N,N咔唑联苯(CBP)或其他金属络合物用作有机电致化合物。然而，这些化合物在溶剂中不具有理想的溶解度，因而不能通过溶液工艺来形成发光层。发光层应当通过沉积工艺形成，因此，制造过程极为复杂，工艺效率也极低。另外，沉积工艺中的废料非常多，导致生产成本增大。
发明内容
本发明的目的一个方面是提供一种有机电致化合物及其使用该化合物的有机发光器件，本发明的磷光化合物具有优异的纯色度、高亮度和优异的发光效率
本发明的另一个目的是提供适于溶液工艺的有机电致化合物。
本发明的另一个目的是提供具有改进的发光效率的OLED。
下文将说明本发明的其他特征和优点，部分特征和优点将从描述中变得明显易懂，或者可以通过实施本发明而获知。本发明的目的和其他优点将凭借说明书和其权利要求及附图中所特别指出的结构来实现或达到。
为了实现这些及其他优点以及本发明的目的，如本文所具体表达和概括描述的，本发明提供一种有机电致化合物，其特征在于：其结构式如1所示，
Figure BDA0002673296570000031
在上述化学式1中X选自O、S、Se、C(R1R2)、NR1、Si(R1R2)；
Ar1取代或未取代的C6-C30芳基、取代或未取代的C2-30杂芳基或Z结构；
Z独立地选自以下结构：
Figure BDA0002673296570000032
A和B各自独立地选自取代或未取代的C6-C30芳基、取代或未取代的C2-C30杂芳基；
Y选自O、S、Se、C(R1R2)、Si(R1R2)、NR1；
X1至X2独立的选自N原子或C原子,其中X1至X2中的至少一个为N；
Y1至Y4独立的选自N原子或C原子；
Ar2取代或未取代的C6-C30芳基、取代或未取代的C2-30杂芳基；
R1和R2各自独立地选自取代或未取代的C6-C30烷基、取代或未取代的C6-C30芳基、取代或未取代的C2-C30杂芳基；
进一步的，所述的C6-C30芳基选自苯基、萘基、联苯基、三联苯基和菲基中的一种。
进一步的，所述的C2-C30杂芳基选自吡啶基、联吡啶基、喹啉基、异喹啉基、菲咯啉基和三嗪基中的一种。
优选的，所述的Ar1独立地选自以下结构：
Figure BDA0002673296570000041
进一步的优选的方式是，所述的有机电致化合物独立地选自下列化合物：
Figure BDA0002673296570000051
Figure BDA0002673296570000061
Figure BDA0002673296570000071
Figure BDA0002673296570000081
Figure BDA0002673296570000091
Figure BDA0002673296570000101
Figure BDA0002673296570000111
Figure BDA0002673296570000121
。
本发明还提供了一种有机电致发光器件，该器件包括阴极层、阳极层和有机层，该有机层包括空穴注入层、空穴传输层、发光层、空穴阻挡层、电子注入层或电子传输层的一层或一层以上，其中有机层中至少有一层含有如结构式1所述的化合物。
进一步的，所述的有机电致发光器件顺次包括沉积的阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层和阴极，所述磷光化合物作为发光层的主体材料。
本发明的优点在于：本发明使用结构式1所示的化学式作为有机发光二极管器件的发光层，具有优异的色纯度和亮度以及延长的耐久性效果。
附图说明
图1为有机电发光二极管发光色度和可见度关系图。表示随有机电致发光器件的色纯度增加(即随色度坐标的X值变得更大)可见度降低。
具体实施方式
为了使本发明实现的技术手段、创作特征、达成目的与功效易于明白了解，下面结合图示与具体实施例，进一步阐述本发明。
现以化合物25、59、145、150、155、160和177制备方法和测试结果为例，证明本发明提供的技术方案和达到的技术效果。LC-MS:液相色谱-质谱联用仪，M/Z：质子数/电荷数的比值。
实施例1：化合物25的合成
(1)中间体25的合成
Figure BDA0002673296570000131
在250ml三口烧瓶中加入中间体Sub-1(3.2g，11.2mmol),中间体25-1-1(4.7g,12.3mmol),三(二亚苄基丙酮)二钯(4mol％),三叔丁基膦(8mol％),叔丁醇钾(3.8g,33.6mmol)和邻二甲苯(80mL)。反应体系升温至120℃,氮气保护下反应12小时。反应完成后,将反应液冷却至室温,用邻二氯苯和水萃取。有机层用无水硫酸镁干燥,浓缩,重结晶所得粗品过硅胶柱得到化合物25(5.6g,yield 80％)。质谱m/z，理论值：501.53；实测值：501.15。
实施例2：化合物59的合成
Figure BDA0002673296570000141
将实施例1中化合物25的方法得到目标产物化合物59(1.56g,收率80.0％)。质谱m/z，理论值：543.68；实测值：543.18。
实施例3.化合物145的合成
Figure BDA0002673296570000142
将实施例1中化合物25的方法得到目标产物化合物145(1.56g,收率80.0％)。质谱m/z，理论值：579.76；实测值：579.21。
实施例4：化合物150的合成
Figure BDA0002673296570000151
将实施例1中化合物25的方法得到目标产物化合物150(1.56g,收率80.0％)。质谱m/z，理论值：612.72；实测值：612.23。
实施例5：化合物155的合成
Figure BDA0002673296570000152
将实施例1中化合物25的方法得到目标产物化合物155(1.9g,收率73.5％)。质谱m/z，理论值：650.63；实测值：651.12。
实施例6：化合物160的合成
Figure BDA0002673296570000153
将实施例1中化合物25的方法得到目标产物化合物160(2.0g,收率75.0％)。质谱m/z，理论值：629.82；实测值：629.23。
实施例7：化合物177的合成
Figure BDA0002673296570000161
将实施例1中化合物25的方法得到目标产物化合物177(2.0g,收率78.0％)。质谱m/z，理论值：742.84；实测值：742.25。
器件实施方案
器件实施方案一:
使ITO玻璃基板图案化,以具有3mm×3mm的发光区域。然后,洗涤图案化的ITO玻璃基板。
随后将该基板安放在真空室。标准压力设定为1×10-6托。此后,在ITO基板上以CuPc
Figure BDA0002673296570000162
NPB
Figure BDA0002673296570000163
RH-001+(mxmq)2Ir(acac)((5％)
Figure BDA0002673296570000164
Alq3
Figure BDA0002673296570000165
LiF
Figure BDA0002673296570000166
和Al
Figure BDA0002673296570000167
的顺序形成有机物质的层。
在0.9mA下,亮度等于1284cd/m2(5.7V)。此时,CIEx＝0.658,y＝0.330。
器件实施方案二：
同器件实施方案一，仅把器件中的化合物177替换为化合物25。
在0.9mA下,亮度等于1251cd/m2(5.4V)。此时,CIEx＝0.658 y＝0.332。
器件实施方案三：
同器件实施方案一，仅把器件中的化合物177替换为化合物59。
在0.9mA下,亮度等于1280cd/m2(5.3V)。此时,CIEx＝0.657,y＝0.331。
器件实施方案四：
同器件实施方案一，仅把器件中的化合物177替换为化合物145。
在0.9mA下,亮度等于1281cd/m2(5.3V)。此时,CIEx＝0.657,y＝0.330。
器件实施方案五：
同器件实施方案一，仅把器件中的化合物177替换为化合物150。
在0.9mA下,亮度等于1282cd/m2(5.4V)。此时,CIEx＝0.658,y＝0.330
器件实施方案六：
同器件实施方案一，仅把器件中的化合物177替换为化合物155。
在0.9mA下,亮度等于1289cd/m2(5.3V)。此时,CIEx＝0.657,y＝0.330。
器件实施方案七：
同器件实施方案一，仅把器件中的化合物177替换为化合物160。
在0.9mA下,亮度等于1287cd/m2(5.3V)。此时,CIEx＝0.657,y＝0.330。
对比例:
使ITO玻璃基板图案化,以具有3mm×3mm的发光区域。然后,洗涤图案化的ITO玻璃基板。
随后将该基板安放在真空室。标准压力设定为1×10-6托。在ITO基板上以CuPc
Figure BDA0002673296570000172
NPB
Figure BDA0002673296570000173
CPB+(mxmq)2Ir(acac)(5％)
Figure BDA0002673296570000174
Alq3
Figure BDA0002673296570000175
LiF
Figure BDA0002673296570000176
和Al
Figure BDA0002673296570000177
的顺序形成有机物质的层。
在0.9mA下,亮度等于1289cd/m2(7.5V)。此时,CIEx＝0.659,y＝0.329。
如图1所示显示有机电致发光器件的色纯度增加(即随色度坐标的X值变得更大)可见度降低。
依据上述实施方案和对比例,效率,色度坐标,和亮度的特性显示在下表1中。
表1
Figure BDA0002673296570000171
Figure BDA0002673296570000181
如表1所示,甚至当色纯度高时,该器件在低电压下也高效率地运行。实施方案的外量子效率(EQE)8％以上。器件实验所用化合物结构如下：
Figure BDA0002673296570000182
如表1所示,该器件在低电压下也高效率地运行。并且,与对比例相比,实施方案的电流效率明显增加。
以上显示和描述了本发明的基本原理、主要特征和本发明的优点。本行业的技术人员应该了解，本发明不受上述实施例的限制，上述实施例和说明书中描述的只是说明本发明的原理，在不脱离本发明精神和范围的前提下本发明还会有各种变化和改进，这些变化和改进都落入要求保护的本发明范围内。本发明要求保护范围由所附的权利要求书及其等同物界定。

Claims (6)

1.一种有机电致化合物，其特征在于：其结构式1所示，
Figure FDA0002673296560000011
在上述化学式1中X选自O、S、Se、C(R1R2)、NR1、Si(R1R2)；
Ar1取代或未取代的C6-C30芳基、取代或未取代的C2-30杂芳基或Z结构；
Z独立地选自以下结构：
Figure FDA0002673296560000012
A和B各自独立地选自取代或未取代的C6-C30芳基、取代或未取代的C2-C30杂芳基；
Y选自O、S、Se、C(R1R2)、Si(R1R2)、NR1；
X1至X2独立的选自N原子或C原子,其中X1至X2中的至少一个为N；
Y1至Y4独立的选自N原子或C原子；
Ar2取代或未取代的C6-C30芳基、取代或未取代的C2-30杂芳基；
R1和R2各自独立地选自取代或未取代的C1-C15烷基、取代或未取代的C6-C30芳基、取代或未取代的C2-C30杂芳基。
2.根据权利要求1所述的有机电致化合物，其特征在于：所述的C6-C30芳基选自苯基、萘基、联苯基、三联苯基和菲基中的一种。
3.根据权利要求1所述的有机电致化合物，其特征在于：所述的C2-C30杂芳基选自吡啶基、联吡啶基、喹啉基、异喹啉基、菲咯啉基和三嗪基中的一种。
4.根据权利要求1所述的有机电致化合物，其特征在于:所述的Ar1、Ar2独立地选自以下：
Figure FDA0002673296560000021
。
5.根据权利要求1-4中任意一项所述的有机电致化合物，其特征在于：所述的有机电致化合物独立地选自下列化合物：
Figure FDA0002673296560000031
Figure FDA0002673296560000041
Figure FDA0002673296560000051
Figure FDA0002673296560000061
Figure FDA0002673296560000071
Figure FDA0002673296560000081
Figure FDA0002673296560000091
Figure FDA0002673296560000101
。
6.一种使用权利要求1-5中任意一项所述的有机电致化合物的有机电致发光二极管器件，其特征在于：所述的有机电致发光器件顺次包括沉积的阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层和阴极，所述有机电致化合物作为发光层的主体材料。
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