CN112062772A - 一种有机化合物及其使用该化合物的有机光电元件与应用 - Google Patents

一种有机化合物及其使用该化合物的有机光电元件与应用 Download PDF

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CN112062772A
CN112062772A CN202010944153.7A CN202010944153A CN112062772A CN 112062772 A CN112062772 A CN 112062772A CN 202010944153 A CN202010944153 A CN 202010944153A CN 112062772 A CN112062772 A CN 112062772A
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高春吉
胡聪从
王朋超
张海龙
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Zhejiang Huadisplay Optoelectronics Co Ltd
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Abstract

本发明涉及一种有机化合物和使用该化合物的有机光电元件，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。本发明包含式1所示的化合物：

Description

一种有机化合物及其使用该化合物的有机光电元件与应用
技术领域
本发明涉及一种有机化合物和使用该化合物的有机光电元件，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。
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
本发明的目的是提供一种有机化合物及其使用该化合物的有机光电元件，应用本发明的有机化合物的OLED器件具有优异的纯色度、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化合物，其特征在于：其结构式如1所示，
Figure BDA0002674642070000031
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 BDA0002674642070000032
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(R3R4)、Si(R3R4)、NR3；
R3和R4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；
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。
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 BDA0002674642070000041
Figure BDA0002674642070000051
R5至R7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。
进一步的优选的方式是，所述的有机化合物独立地选自下列化合物：
Figure BDA0002674642070000061
Figure BDA0002674642070000071
Figure BDA0002674642070000081
Figure BDA0002674642070000091
Figure BDA0002674642070000101
Figure BDA0002674642070000111
Figure BDA0002674642070000121
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或结构式2所述的化合物。
进一步的，所述的有机电致发光器件按阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层和阴极顺序蒸镀或涂布，所述有机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或结构式2所示的化学式作为有机电致发光器件的发光层，具有优异的色纯度和亮度以及延长的耐久性效果。
Figure BDA0002674642070000131
其中，X选自O、S、Se、C(R1R2)、NR1、Si(R1R2)；
R1、R2独立的选自取代或未取代的C6-C30芳基、取代或未取代的C2-30杂芳基；
Ar1独立的选自取代或未取代的C6-C30芳基、取代或未取代的C2-30杂芳基。
式-1-4在氮气保护，三苯基膦、反-二(三苯基膦)二氯化钯、苯酚钾、溶剂为甲苯的条件下，与联硼酸频那醇酯偶联反应得到中间体式-1-3；
按照本发明，中间体式-1-2按照如下所示方法制备得到：
中间体式-1-3在氮气保护，四三苯基膦钯为催化剂，碳酸钾为碱，四氢呋喃为溶剂的条件下，与1,8-dibromonaphthalene通过C-C偶联反应得到中间体式-1-2；
按照本发明，中间体式-1-1按照如下所示方法制备得到：
中间体式-1-2在氮气保护，三(二亚苄基茚丙酮)二钯(0)、1,8-二氮杂二环十一碳-7-烯、三环己基膦，二甲基乙酰胺为溶剂的条件下，得到中间体式-1-1；
按照本发明，式-1化合物按照如下所示方法制备得到：
式-1-1在氮气保护，醋酸钯、三叔丁基膦为催化剂，叔丁基醇钠为碱，溶剂为甲苯的条件下，与ArBr反应经由C-N偶联反应，得到化合物式-1。
附图说明
图1为有机电致发光器件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和150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。
下式为在本发明的实施方案中使用的HIL-1、HI-2、HT-1、HT-2、RD-1、ET-1的结构式。
Figure BDA0002674642070000141
形成例
实施例1：化合物25的合成
(1)中间体25-1-3的合成
Figure BDA0002674642070000142
在氮气保护条件下,向三口瓶中加入25-1-4(53.13g,81.3mmol),联硼酸频那醇酯(24.8g,97.5mmol),三苯基膦(6mol％),反-二(三苯基膦)二氯化钯(II)(3mol％), 苯酚钾(16.1g,121.9mmol)和无水甲苯(300mL)。氮气置换后在50℃条件下搅拌反应5 小时，然后将体系冷却到室温并加水猝灭反应。反应混合物用苯溶剂和饱和食盐水萃取。取有机相用无水硫酸镁干燥。将干燥后混合物过滤并减压浓缩，可通过硅胶层析柱或者蒸馏法进行提纯得到中间体25-1-3(46.1g,yield 81％)。质谱m/z，理论值：700.63；实测值：700.29。
(2)中间体25-1-2的合成
Figure BDA0002674642070000151
在500mL反应瓶中加入中间体25-1-3(43.0g,61.4mmol),1,2-二溴苯 (14.5g,61.4mmol),四(三苯基膦)钯(5mol％),K2CO3(17.0g,122.8mmol),1,4-二氧六环(200mL)和水(50mL)。反应体系升温至80℃,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中间25-1-2(33.6g,yield 75％)。质谱m/z，理论值：729.66；实测值：728.15。
(3)中间体25-1-1的合成
Figure BDA0002674642070000152
在氮气条件下，铯碳酸(390mg，1.2mmol)，双(苄腈)二氯钯(9.6mg，0.025 mmol)和三{3,5-双(三氟甲基)苯基}-将膦(34mg，0.050mmol)放入20mL Schlenk 管。加入25-1-2(438mg，0.60mmol)的甲苯(2.0mL)溶液。将所得混合物在110℃下搅拌24小时。然后将混合物冷却至室温。盐酸加入(1M，6mL)，并将产物用乙酸乙酯萃取。醋酸盐(10毫升×3)。然后将有机层用盐水洗涤并用无水硫酸钠干燥。在挥发物被蒸发，硅胶柱纯化，以己烷为洗脱剂得到25*1-1(264mg，68％产率)。质谱m/z，理论值：648.75；实测值：648.22。
(4)化合物25的合成：
Figure BDA0002674642070000161
在250ml三口烧瓶中加入中间体Sub-1(3.2g，11.2mmol),中间体25-1-1(8.0g,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(8.0g,yield 80％)。质谱m/z，理论值： 893.00；实测值：892.28。
实施例2：化合物59的合成
Figure BDA0002674642070000162
将实施例1中化合物25的方法得到目标产物化合物59(1.7g,收率79.0％)。质谱m/z，理论值：859.05；实测值：858.28。
实施例3.化合物145的合成
Figure BDA0002674642070000171
将实施例1中化合物25的方法得到目标产物化合物145(3.2g,收率78.0％)。质谱m/z，理论值：895.13；实测值：894.32。
实施例4：化合物150的合成
Figure BDA0002674642070000172
将实施例1中化合物25的方法得到目标产物化合物150(2.7g,收率75.5％)。质谱m/z，理论值：928.09；实测值：927.34。
实施例5：化合物155的合成
Figure BDA0002674642070000173
将实施例1中化合物25的方法得到目标产物化合物1-155(1.9g,收率73.5％)。质谱m/z，理论值：965.99；实测值：966.23。
实施例6：化合物160的合成
Figure BDA0002674642070000174
将实施例1中化合物25的方法得到目标产物化合物1-160(2.0g,收率75.0％)。质谱m/z，理论值：945.19；实测值：944.33。
器件实施方案
1.第一实施方案
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HIL-1:HI-2
Figure BDA0002674642070000181
HT-1
Figure BDA0002674642070000182
HT2(800nm)化合25+RD-1(5％)
Figure BDA0002674642070000183
ET-1
Figure BDA0002674642070000184
EI-1
Figure BDA0002674642070000185
和Al
Figure BDA0002674642070000186
的顺序形成有机物质的层。
2.第二实施方案
采用上述第一实施方案同样的方法制备第二实施方案的有机电致发光器件，仅把有机电致发光器件的主体材料层由第一实施方案主体材料25替换为59。
3.第三实施方案
采用上述第一实施方案同样的方法制备第三实施方案的有机电致发光器件，仅把有机电致发光器件的主体材料层由第一实施方案主体材料25替换为145。
4.第四实施方案
采用上述第一实施方案同样的方法制备第四实施方案的有机电致发光器件，仅把有机电致发光器件的主体材料层由第一实施方案主体材料25替换为150。
5.第五实施方案
采用上述第一实施方案同样的方法制备第四实施方案的有机电致发光器件，仅把有机电致发光器件的主体材料层由第一实施方案主体材料25替换为155。
6.第六实施方案
采用上述第一实施方案同样的方法制备第四实施方案的有机电致发光器件，仅把有机电致发光器件的主体材料层由第一实施方案主体材料25替换为160。
对比例1
采用上述第一实施方案同样的方法制备对比例的有机电致发光器件，仅把有机电致发光器件的主体材料层由第一实施方案主体材料25替换为替换为化合物A。
对比例2
采用上述第一实施方案同样的方法制备对比例的有机电致发光器件，仅把有机电致发光器件的主体材料层由第一实施方案主体材料25替换为替换为化合物B。
Figure BDA0002674642070000191
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
序号 V mA/cm2 Cd/A EQE CIEx CIEY
第一实施例 3.57 10.00 46.61 41.40 0.6913 0.3086
第二实施例 4.09 10.00 45.92 38.81 0.6891 0.3108
第三实施例 4.06 10.00 46.41 41.22 0.6916 0.3083
第四实施例 4.24 10.00 45.68 38.98 0.6891 0.3108
第五实施例 4.00 10.00 47.43 35.12 0.6829 0.3169
第六实施例 4.14 10.00 46.66 36.95 0.6858 0.3141
对比例1 4.47 10.00 34.03 27.45 0.6878 0.3121
对比例2 4.98 10.00 34.63 34.37 0.6953 0.3046
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,第二实施方案的电流效率增加。
以上结果显示，在对比例结构上增加一个芳并环，可以显著降低器件的操作电压，提升器件的电流效率。
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)

1.一种有机化合物，其特征在于：其结构式如式1所示，
Figure FDA0002674642060000011
在上述化学式1中X选自O、S、Se、C(R1R2)、NR1、Si(R1R2)；
R1和R2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；
Ar1选自取代或未取代的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 FDA0002674642060000012
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(R3R4)、Si(R3R4)、NR3；
R3和R4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；
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选自取代或未取代的C6-C30芳基、取代或未取代的C2-30杂芳基。
2.根据权利要求1所述的有机化合物，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所述的有机化合物，其特征在于:所述的Ar1独立地选自以下：
Figure FDA0002674642060000021
Figure FDA0002674642060000031
R5至R7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。
5.根据权利要求1-4中任意一项所述的有机化合物，其特征在于：所述的有机化合物独立地选自下列化合物：
Figure FDA0002674642060000041
Figure FDA0002674642060000051
Figure FDA0002674642060000061
Figure FDA0002674642060000071
Figure FDA0002674642060000081
Figure FDA0002674642060000091
Figure FDA0002674642060000101
6.一种使用权利要求1-5中任意一项所述的有机化合物的有机发光器件，其特征在于：所述的有机发光器件按阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层和阴极顺序蒸镀或涂布，所述有机化合物作为发光层的主体材料。
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