CN100374526C - 环戊菲基化合物和使用该化合物的有机电致发光装置 - Google Patents

环戊菲基化合物和使用该化合物的有机电致发光装置 Download PDF

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CN100374526C
CN100374526C CNB2004100995020A CN200410099502A CN100374526C CN 100374526 C CN100374526 C CN 100374526C CN B2004100995020 A CNB2004100995020 A CN B2004100995020A CN 200410099502 A CN200410099502 A CN 200410099502A CN 100374526 C CN100374526 C CN 100374526C
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金奎植
孙炳熙
夫龙淳
孙准模
朴商勋
李志勋
白云仲
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Samsung Display Co Ltd
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Abstract

本发明提供了一种环戊菲基化合物和使用该化合物的有机电致发光装置。由于环戊菲基化合物具有多种优点，例如易加工性，高溶解性、杰出的色纯度、色稳定性、热稳定性等等，它不仅能方便地用于作为有机电致发光装置的有机层，特别是发光层的成型材料，而且也可以作为有机颜料和非线性光学基材的材料。

Description

环戊菲基化合物和使用该化合物的有机电致发光装置
技术领域
本发明涉及一种环戊菲基化合物和一种使用该化合物的有机电致发光装置，特别是涉及一种环戊菲基化合物和一种使用该化合物作为有机层的有机电致发光装置。
背景技术
有机电致发光装置通常包括阳极、有机发光层和阴极。在有机发光层中，阴极的电子和阳极的空穴再结合形成激子，当激子变成基态时，产生电致发光。
Eastman Kodak公司开发了具有多层结构的电致发光装置，这种多层结构包括喹啉铝复合层和三苯胺衍生物层。这种多层结构装置的开发使选用低分子量分子形成有机发光层成为可能，并能使发光具有从UV区到IR区的宽波长范围。
基于共轭聚合物聚亚苯基亚乙烯(下文中，简称PPV)的EL装置的开发最初是由英国剑桥大学通过湿法涂膜工艺(Nature，vol 347,539，1990)实现。后来，Covion Co.开发了一种新的PPV型聚合物，它溶于有机溶剂并且具有高的化学稳定性和发光效率。同样，Dow Chemical Co.开发了一种比PPV型化合物具有更好性能的发光层成型材料聚芴化合物。特别地，聚芴化合物作为蓝色发光聚合物是一种有前途的材料。由于激基缔合物(excimer)是由聚芴结构的侧链产生的，因此聚芴化合物仍然需要进行更多改进，特别是色纯度。(见美国专利号5,900,327)。为了改进聚芴的色纯度，开发了多种发光材料，其中包括美国专利号5,621,131中公开的聚螺芴和美国专利号5,763,636中公开的螺二芴或含有杂原子的螺芴。
然而，采用现有发光材料制造的有机电致发光装置仍然需要进一步的改进，特别是在效率、色纯度等方面。
发明内容
本发明提供了具有环戊菲结构的环戊菲基化合物和使用该化合物的有机电致发光装置，这种化合物具有改进的发光效率、热稳定性和色纯度。
一方面，本发明提供了一种用式1表示的环戊菲基化合物：
[式1]
     
Figure C20041009950200101
其中X是碳、氮、氧或硫，当X是碳时，a和b都是1；当X是氮时，a和b中的一个是0；当X是氧或硫时，a和b都是0。
R1和R2各自独立地选自：氢、取代或未取代的C1-C30烷基、取代或未取代的C3-C30环烷基、取代或未取代的C1-C30烷氧基、取代或未取代的C6-C30芳基、取代或未取代的C6-C30芳氧基、取代或未取代的C6-C30芳烷基、取代或未取代的C2-C30杂芳基、取代或未取代的C6-C30杂芳氧基、取代或未取代的C2-C30杂芳氧基、或者R1和R2互相连接形成饱和或不饱和的C3-C30环状体系。
R3、R3′、R4、R4′、R5和R5′各自独立地选自：氢、羟基、取代或未取代的氨基、氰基、卤素原子、取代或未取代的C1-C30烷基、取代或未取代的C3-C30环烷基、取代或未取代的C1-C30烷氧基、取代或未取代的C6-C30芳基、取代或未取代的C6-C30芳烷基、取代或未取代的C2-C30杂芳基；和
m是2-5000的实数。
环戊菲基化合物还可以含有亚芳基(Ar)重复单元，并且用式2表示：
[式2]
    
其中
Ar是取代或未取代的C6-C30亚芳基、取代或未取代的C2-C30杂亚芳基；
R1、R2、R3、R3′、R4、R4′、R5、R5′、X、a和b同上定义；
m是2-5000的实数；和
n是0.01-1的实数。
本发明实施方案的另一个方面是提供一种在两个电极间含有有机层的有机电致发光装置，其中该有机层包含环戊菲基化合物。
附图说明
参照附图通过对示例性实施例的详细描述，本发明的上述和其他特性以及优点变得更加显而易见，其中：
图1是本发明实施例4所述的二辛基环戊菲-吩嗪共聚物的光致发光(PL)光谱。
图2说明了本发明实施例4所述的二辛基环戊菲-吩嗪共聚物的色纯度特性。
具体实施方式
本发明提供了用式1表示的环戊菲基化合物。本发明还提供了一种含有亚芳基重复单元的用式2表示的环戊菲基化合物。在式2中，n定义为在整个聚合物中所含环戊菲重复单元的混合比例，1-n定义为在整个聚合物中所含亚芳基重复单元的混合比例。
在式1中，n是0.01-1的实数，优选为0.5-1。在式1中，当R1和R2相互连接形成环时，形成了取代或未取代的C3-C30环。在这种情况下，该环可含有杂原子，例如氮、氧或硫。
在式1中，一种或多种取代烷基、环烷基、烷氧基、芳基、芳烷基、杂芳基、氨基和/或相应的环的实例包括C1-C12烷基、C1-C12烷氧基、卤素原子、C1-C12低级烷基氨基、羟基、硝基、氰基、取代或未取代氨基(-NH2，-NH(R)，-N(R′)(R″)，其中R′和R″各自独立地为C1-C12烷基、羧基、磺酸、磷酸、C1-C20卤代烷基、C2-C20链烯基、C2-C20炔基、C1-C20杂烷基、C6-C30芳基、C6-C20芳烷基、C2-C20杂芳基或C2-C20杂芳烷基。
在式1中，亚芳基(Ar)单元具有例如式3的结构，优选吩嗪：
[式3]
Figure C20041009950200121
其中Y是氧或硫；R6、R7、R8和R9各自独立地选自：氢、羟基、取代或未取代的氨基、氰基、卤素原子、取代或未取代的C1-C30烷基、取代或未取代的C3-C30环烷基、取代或未取代的C1-C30烷氧基、取代或未取代的C6-C30芳基和取代或未取代的C2-C30杂芳基。
式1的环戊菲基化合物的实例包括式6代表的化合物：
[式6]
    
Figure C20041009950200122
其中R1和R2各自独立地为取代或未取代的C1-C12烷基；m是2-5000的实数。
在式1代表的环戊菲基化合物中，通过R1和R2相互连接形成环的化合物的实例包括式5的化合物：
[式5]
    
Figure C20041009950200131
其中R3、R4、R5、R3′、R4′、R5′、R10、R11、R12、R13、R14、R15、R16和R17同上定义，m也同上定义。
式6的化合物的实例包括式7的化合物：
[式7]
    
Figure C20041009950200132
在式2的环戊菲基化合物中，通过R1和R2相互连接形成环的化合物的实例包括式4的化合物：
[式4]
    
Figure C20041009950200133
其中Ar、R3、R3′、R4、R4′、R5、R5′、X、n和m同上定义；并且R10、R11、R12、R13、R14、R15、R16和R17各自独立地选自：氢、羟基、取代或未取代的氨基、氰基、卤素原子、取代或未取代的C1-C30烷基、取代或未取代的C3-C30环烷基、取代或未取代的C1-C30烷氧基、取代或未取代的C6-C30芳基、取代或未取代的C6-C30芳氧基、取代或未取代的C6-C30芳烷基、取代或未取代的C2-C30杂芳基和取代或未取代的C2-C30杂芳氧基。
式4的化合物的实例包括式8的化合物：
[式8]
    
Figure C20041009950200141
其中R1、R2和R6各自独立地为取代或未取代的C1-C12烷基；n是0.01-0.99的实数，m是2-5000的实数。
式8的化合物的实例包括式9的化合物：
[式9]
    
Figure C20041009950200142
其中n是0.01-0.99的实数，m是2-5000的实数。
通过将由新的环戊菲基化合物或螺环戊菲基化合物制成的单一物质进行聚合反应或将该化合物与含有卤化物的亚芳基(Ar)单体进行共聚反应，能够得到本发明的环戊菲基化合物。
如上所述，环戊菲基化合物提供了多种加工优点，包括易加工性、高稳定性、较高的色纯度、色稳定性和热稳定性，并且它不仅仅是能方便地用于作为有机电致发光装置的有机层的成型材料。
根据本发明，含有式1重复单元的环戊菲基化合物的聚合度优选为15或更高，特别优选为15-350。优选地，该化合物的数均分子量不能低于10000，更优选地，该化合物的数均分子量为10000-200000。在这种情况下，化合物具有良好的成膜性。
通过用式1的环戊菲基化合物形成有机层，特别是发光层，可以制造本发明所述的有机电致发光装置。式1的环戊菲基化合物能够作为发光层的成型材料来使用，特别是蓝色发光材料。而且，环戊菲基化合物能够用作有机层例如空穴传输层(hole transport layer)的成型材料。
优选地，式1的环戊菲基化合物在发光层形成材料总重量中占约1-30重量份。适用于在发光层中导入环戊菲基化合物的方法的实例包括真空沉积、溅射、涂膜、喷墨印刷、电子束放射(electron-beam radiation)等。
有机层的厚度优选的范围为约50-100nm。在本文中所用的术语“有机层”的意思是在有机电致发光装置中在一对电极间由有机化合物形成的层，例如，发光层、电子传输层(electron transport layer)，空穴传输层等。
该有机电致发光装置具有已知的结构，包括：阳极/发光层/阴极、阳极/缓冲层/发光层/阴极、阳极/空穴传输层/发光层/阴极、阳极/缓冲层/空穴传输层/发光层/阴极、阳极/缓冲层/空穴传输层/发光层/电子传输层/阴极和阳极/缓冲层/空穴传输层/发光层/空穴阻挡层/阴极，但是并不局限于这些结构。
缓冲层的实例包括在本领域中通常使用的任何材料，并且优选的是铜酞菁、聚噻吩、聚苯胺、聚乙炔、聚吡咯、聚亚苯基亚乙烯和其衍生物，但又不仅限于这些。
空穴传输层的实例包括在本领域中通常所使用的任何材料，优选的是聚三苯胺，但又不仅限于这些。
电子传输层的实例包括在本领域中通常所使用的任何材料，优选的是聚二唑，但又不仅限于这些。
空穴阻挡层的实例包括在本领域中通常所使用的任何材料，优选的是LiF、BaF2或MgF2，但又不仅限于这些。
在下文中，通过下面的实施例对本发明进行更加详细的说明。然而，所给出的这些实施例是以说明为目的，并没有局限性。
实施例1
4，4-二辛基-环戊[def]菲的合成
将3g(15.76mmol)的环戊[def]菲和7.74mL(44.80mmol)的辛基溴溶于300mL的四氢呋喃中，将94.68mL的1M的叔丁基氧化钾缓慢的滴加到溶液中，搅拌下于50℃加热一小时，然后通过减压浓缩除去四氢呋喃。向反应混合物中加入300mL的乙酸乙酯进行提纯，然后用盐水清洗。得到的产品用蒸馏水洗一次，用硫酸镁将乙酸乙酯脱水干燥，随后过滤并减压浓缩。将所得的混合物用硅胶柱色谱法(洗脱液：己烷)进行分离，得到4.68g的目标产物4，4-二辛基-环戊[def]菲，产率为71.67％。
1H-NMR(CDCl3)：ppm，0.80(m，10H，辛基)，1.07-1.25(m，20H，辛基)，2.10-2.17(m，4H，辛基)，7.49(m，2H，芳香族)，7.60(m，2H，芳香族)，7.79(m，4H，芳香族)
质谱：414(M+)，301，189
实施例2
4，4-二辛基-2，6-二溴环戊[def]菲的合成
向反应烧瓶中加入3g(7.2mmol)实施例1中制备的4，4-二辛基-环戊[def]菲，将混合物溶于50mL二氯甲烷中。然后将反应在黑暗条件下进行，然后用37ml二氯甲烷稀释0.74mL溴所得到的溶液在室温下缓慢地滴入反应混合物中，滴加结束后，将反应混合物搅拌约30分钟，然后在减压的条件下进行浓缩。所得的混合物用硅胶柱色谱法(洗脱液：己烷)进行分离，得到2.17g的目标产品4，4-二辛基-2，6-二溴环戊[def]菲，产率为52.5％。
1H-NMR(CDCl3)：ppm，0.80(m，10H，辛基)，1.07-1.21(m，20H，辛基)，2.10-2.14(m，4H，辛基)，7.35(d，1H，芳香族)，7.53(d，1H，芳香族)，7.65(t，H，芳香族)，7.79(d，1H，芳香族)，7.82，7.93(dd，2H，芳香族)
质谱：572(M+)，494，381，300，215，201
实施例3
聚二辛基环戊菲的合成
首先，将Schlenk烧瓶抽真空，然后用氮气回流(reflux)几次使其完全干燥。然后在手套式操作箱中，将480mg(1.7mmol)的双(1，5-环辛二烯)镍(O)和273mg(1.7mmol)的2，2′-二吡啶加入Schlenk烧瓶中，接着再将烧瓶抽真空和用氮气回流几次。在氮气条件下，向烧瓶中加入4mL无水二甲基甲酰胺(DMF)、0.2mL的1，5-环辛二烯(cyclooctadie)(COD)和5mL的无水甲苯。混合物在70℃条件下搅拌30分钟后，将用8mL甲苯稀释500mg(0.873mmol)实施例2中制备的4，4-二辛基-2，6-二溴环戊[def]菲所得的溶液加入混合物中。反应混合物在70℃条件下回流24小时，然后冷却至室温。
反应物用酸性溶液进行处理得到沉淀，该酸性溶液例如，包括体积比为1∶1∶2的盐酸、丙酮和甲醇的混合溶液。沉淀物用甲苯和甲醇纯化，随后通过用soxhlet萃取器处理，得到产率为70％的最终产物。
由凝胶渗透色谱法分析结果可以看出，最终产物的数均分子量(Mn)约为50000。
实施例4
二辛基环戊菲-吩嗪共聚物(摩尔比为90∶10)的合成
[反应方案1]
    
首先，将Schlenk烧瓶抽真空，然后用氮气回流几次使其完全干燥。然后在手套式操作箱中，将534mg(1.9mmol)的双(1，5-环辛二稀)镍(O)和300mg(1.9mmol)的2，2′-二吡啶加入到Schlenk烧瓶中，然后将烧瓶抽真空并再用氮气回流几次。在氮气条件下，向烧瓶中加入4mL无水二甲基甲酰胺(DMF)、0.2mL的1，5-环辛二烯(COD)和8mL的无水甲苯。将反应混合物在70℃条件下搅拌30分钟。将用8mL无水甲苯稀释500mg(0.9mmol)实施例2中制备的4，4-二辛基-2，6-二溴环戊[def]菲和53mg(0.1mmol)的二溴吩嗪衍生物3，7-二溴-10-[4-(2-乙基-己氧基)-苯基]-10，10a-二氢-4aH-吩嗪所得的溶液加入混合物中。反应混合物在70℃条件下回流24小时，然后冷却至室温。反应物用酸性溶液进行处理得到沉淀，该酸性溶液例如，包括体积比为1∶1∶2的盐酸、丙酮和甲醇的混合溶液。沉淀物用甲苯和甲醇纯化，随后使用soxhlet萃取器处理，得到产率为65％的最终产物。
从GPC分析结果可以看出，最终产物的数均分子量(Mn)约为56000。
图1和图2中给出了二辛基环戊菲-吩嗪共聚物的PL和色纯度特性。参考图1可以看出，二辛基环戊菲-吩嗪共聚物的最大发射峰在365nm处。在这一波长条件下，在NTSC色度坐标系中二辛基环戊菲-吩嗪共聚物的色纯度是CIE(x，y)：0.16，0.25。
环戊菲基化合物表现出明显的加工优点，例如易加工性，高溶解性、杰出的色纯度、色稳定性、热稳定性等等，它不仅能方便地用于作为有机电致发光装置的有机层，特别是发光层的成型材料，而且也可以作为有机颜料或非线性光学基材的材料。

Claims (13)

1.式2所代表的环戊菲基化合物：
[式2]
Figure C2004100995020002C1
其中
Ar单元选自下面式3所代表的结构：
[式3]
Figure C2004100995020002C2
Y是氧或硫；
R6、R7、R8和R9各自独立地选自：氢、羟基、氨基、氰基、卤素原子、C1-C30烷基、C3-C30环烷基、C1-C30烷氧基、C6-C30芳基和C2-C30杂芳基；
X是碳，当X是碳时，a和b都为1；
R1和R2各自独立地选自：氢、C1-C30烷基、C3-C30环烷基、C1-C30烷氧基、C6-C30芳基、C6-C30芳氧基、C6-C30芳烷基、C2-C30杂芳基、和C2-C30杂芳氧基、或者R1和R2互相连接形成饱和或不饱和的C3-C30环状体系；
R3、R3′、R4、R4′、R5和R5′各自独立地选自：氢、羟基、氨基、氰基、卤素原子、C1-C30烷基、C3-C30环烷基、C1-C30烷氧基、C6-C30芳基、C6-C30芳烷基、和C2-C30杂芳基；和
m是2-5000的实数；
n是0.01-1的实数。
2.权利要求1的环戊菲基化合物，其为式4所代表的化合物：
[式4]
Figure C2004100995020003C1
其中
Ar、R3、R3′、R4、R4′、R5、R5′、X、n和m同权利要求1所定义；和
R10、R11、R12、R13、R14、R15、R16和R17各自独立地选自：氢、羟基、氨基、氰基、卤素原子、C1-C30烷基、C3-C30环烷基、C1-C30烷氧基、C6-C30芳基、C6-C30芳氧基、C6-C30芳烷基、C2-C30杂芳基和C2-C30杂芳氧基。
3.权利要求1或2的环戊菲基化合物，其为式5或式6所代表的化合物：
[式5]
Figure C2004100995020004C1
[式6]
Figure C2004100995020004C2
其中
R3、R4、R5、R3′、R4′、R5′、R10、R11、R12、R13、R14、R15、R16、R17、X和m同权利要求2所定义；
R1和R2各自独立地为C1-C12烷基。
4.权利要求3的环戊菲基化合物，其为式7所代表的化合物：
[式7]
Figure C2004100995020004C3
其中m是2-5000的实数。
5.权利要求1的环戊菲基化合物，其为式8所代表的化合物：
[式8]
Figure C2004100995020004C4
其中
R1、R2和R6各自独立地为C1-C12烷基；
n是0.01-0.99的实数；和
m是2-5000的实数。
6.权利要求5的环戊菲基化合物，其为式9所代表的化合物：
[式9]
Figure C2004100995020005C1
其中n是0.01-0.99的实数；和m是2-5000的实数。
7.在一对电极间含有有机层的有机电致发光装置，其中所述有机层包括
式2代表的环戊菲基化合物：
[式2]
Figure C2004100995020005C2
其中
Ar单元选自下面式3所代表的结构：
[式3]
Figure C2004100995020006C1
Y是氧或硫；
R6、R7、R8和R9各自独立地选自：氢、羟基、氨基、氰基、卤素原子、C1-C30烷基、C3-C30环烷基、C1-C30烷氧基、C6-C30芳基和C2-C30杂芳基；
X是碳，当X是碳时，a和b都为1；
R1和R2各自独立地选自：氢、C1-C30烷基、C3-C30环烷基、C1-C30烷氧基、C6-C30的芳基、C6-C30芳氧基、C6-C30芳烷基、C2-C30杂芳基、和C2-C30杂芳氧基、或者R1和R2互相连接形成饱和或不饱和的C3-C30环状体系；
R3、R3′、R4、R4′、R5和R5′各自独立地选自：氢、羟基、氨基、氰基、卤素原子、C1-C30烷基、C3-C30环烷基、C1-C30烷氧基、C6-C30芳基、C6-C30芳烷基、和C2-C30杂芳基；和
m是2-5000的实数；
n是0.01-1的实数。
8.权利要求7的有机电致发光装置，其中所述有机层是发光层或空穴传输层。
9.权利要求7的有机电致发光装置，所述环戊菲基化合物为式4所代表的化合物：
[式4]
Figure C2004100995020007C1
其中
Ar、R3、R3′、R4、R4′、R5、R5′、X、n和m同权利要求7所定义；和
R10、R11、R12、R13、R14、R15、R16和R17各自独立地选自：氢、羟基、氨基、氰基、卤素原子、C1-C30烷基、C3-C30环烷基、C1-C30烷氧基、C6-C30芳基、C6-C30芳氧基、C6-C30芳烷基、C2-C30杂芳基和C2-C30杂芳氧基。
10.权利要求7或9的有机电致发光装置，所述环戊菲基化合物为式5或式6所代表的化合物：
[式5]
Figure C2004100995020007C2
[式6]
Figure C2004100995020007C3
其中
R3、R4、R5、R3′、R4′、R5′、R10、R11、R12、R13、R14、R15、R16、R17、X和m同权利要求9所定义；
R1和R2各自独立地为C1-C12烷基。
11.权利要求10的有机电致发光装置，其为式7所代表的化合物：
[式7]
Figure C2004100995020008C1
其中m是2-5000的实数。
12.权利要求9的有机电致发光装置，其为式8所代表的化合物：
[式8]
Figure C2004100995020008C2
其中
R1、R2和R6各自独立地为C1-C12烷基；
n是0.01-0.99的实数；和
m是2-5000的实数。
13.权利要求12的有机电致发光装置，其为式9所代表的化合物：
[式9]
Figure C2004100995020008C3
其中n是0.01-0.99的实数；和m是2-5000的实数。
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JP4898106B2 (ja) 2012-03-14
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