CN103554011B - 一种含蒽类衍生物、制备方法及其应用 - Google Patents

一种含蒽类衍生物、制备方法及其应用 Download PDF

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CN103554011B
CN103554011B CN201310528288.5A CN201310528288A CN103554011B CN 103554011 B CN103554011 B CN 103554011B CN 201310528288 A CN201310528288 A CN 201310528288A CN 103554011 B CN103554011 B CN 103554011B
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anthracene derivative
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electrode
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CN103554011A (zh
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马晓宇
王辉
高春吉
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

本发明公开了一种含蒽类衍生物、制备方法及其应用，所述蒽类衍生物的分子通式为：

Description

一种含蒽类衍生物、制备方法及其应用
技术领域
本发明涉及有机光电材料领域，尤其涉及一种含蒽类衍生物、制备方法及其应用。
背景技术
有机电致发光一般由两个对置的电极和插入在该两个电极之间的至少一层有机发光化合物组成。电荷被注入到在阳极和阴极之间形成的有机层中，以形成电子和空穴对，使具有荧光或磷光特性的有机化合物产生了光发射。
对于有机电致发光材料的研究是从1950年Bernose对含有有机色素的高分子薄膜施加高电流电压观测到的。1965年，Pope等人首次发现了蒽单晶的电致发光性质，这是有机化合物的首例电致发光现象。
为了制作高效率的有机发光器件，研究者逐渐把器件内有机物层的结构从单层变为多层结构。把有机电致发光器件设计为多层结构是由于空穴和电子的移动速度不同，适当的设计出空穴注入层，空穴传输层，电子传输层及电子注入层，提高了空穴和电子的传输效率，使器件中空穴和电子达到均衡，从而提高发光效率。已知激发子具有将其能量转移给重新组合部位附近的材料中具有更小带隙的材料的倾向。因此，掺杂剂选自于比主材料具有更高的量子产量和更小的带隙（更大的波长）的材料；否则，激发子的能量将转移至具有更低量子产量的主材料，并因此产生弱的发射或者不发射。但是至今没有理想的稳定高效率的有机发光材料用于有机物层。因此，现有技术还有待于更进一步的改进和发展。
发明内容
鉴于上述现有技术的不足，本发明的目的在于提供一种含蒽类衍生物、制备方法及其应用，旨在提供一种新的高效的有机电致发光材料。
本发明的技术方案如下：
一种含蒽类衍生物，其中，所述蒽类衍生物的分子通式为：
其中，R为碳原子数为5～32的芳族杂环基或杂原子化合物取代基。
所述的含蒽类衍生物，其中，所述含蒽类衍生物至少为
中的一种。
一种所述含蒽类衍生物的制备方法，其包括以下步骤：
步骤S1：向反应体系中加入蒽类溴取代化合物、含取代基R的硼酸化合物；
步骤S2：对所述反应体系进行脱气，然后加入催化剂；
步骤S3：升高所述反应体系的反应温度并回流，充分反应，得到所述含蒽类衍生物。
一种采用所述含蒽类衍生物制成的有机发光器件，其包括第一电极、第二电极以及置于所述第一电极、所述第二电极之间的一个或多个有机化合物层，其中，至少一个所述有机化合物层由如权利要求1所述含蒽类衍生物制成。
一种所述含蒽类衍生物的应用，其中，所述含蒽类衍生物在所述有机电致发光器件中用作磷光绿色主体材料、荧光绿色主体材料、空穴注入材料或者空穴传输材料。
本发明提供了一种含蒽类衍生物、制备方法及其应用，采含蒽类衍生物具有高的发光效率，高的发光效率表明该化合物可作为发光材料或发光主体材料，尤其是可以作为磷光绿色主体材料，应用在有机电致发光器件中，其制造成本较低，延长了有机电致发光器件的寿命，降低了有机电致发光器件的制造成本；用于有机电致发光器件中表现出高效率、高亮度、长寿命且更好的电荷传输能力，高的玻璃化温度并且不结晶。
具体实施方式
本发明提供了一种含蒽类衍生物、制备方法及其应用，为使本发明的目的、技术方案及效果更加清楚、明确，以下对本发明进一步详细说明。应当理解，此处所描述的具体实施例仅仅用以解释本发明，并不用于限定本发明。
本发明提供了一种含蒽类衍生物，所述蒽类衍生物的分子通式为：
其中，R为碳原子数为5～32的芳族杂环基或杂原子化合物取代基。
为了更具体的描述本发明中所述含蒽类衍生物，其具体的表现形式至少为表1中标号1-48中的一种。
表1
本发明还提供了一种所述含蒽类衍生物的制备方法，其包括以下步骤：
步骤S1：向反应体系中加入蒽类溴取代化合物、含取代基R的硼酸化合物；
步骤S2：对所述反应体系进行脱气，然后加入催化剂；
步骤S3：升高所述反应体系的反应温度并回流，充分反应，得到所述含蒽类衍生物。
实施例1
为了更详尽的说明本发明中的制备方法，以下以标号为31的含蒽类衍生物为例进行描述。其具体的反应方程式如式1所示的。
式1
在氮气保护下，向2L反应釜中加入式1中化合物[31-1]50g(103.00mmol),化合物[31-2]41.79g(133.90mmol),K2CO322.77g(164.80mmol),甲苯500mL搅拌。并将反应釜内温度升高到70℃时，加入催化剂四(三苯基膦)钯3.57g(3.09mmol)，加入蒸馏水75mL搅拌11小时。加70mL水结束反应，减压过滤得到目标衍生物的粗产品，用蒸馏水洗涤三次，然后用丙酮，甲苯，四氢呋喃溶液重结晶得到固体再升华精制处理，甲苯重结晶，得到淡绿色固体目标衍生物31.25g，产率为36%。
其中表1中标号1-48含蒽类衍生物的制备过程基本相同，在此不再一一赘述，仅将其具体结果列于表2中。并且在制备本发明含蒽类衍生物过程中，添加各个物质的量，可以根据上述实施例中各个物质的比例进行确定，本发明重点是描述工艺过程，对添加各个物质的量不再作一一阐述。
表2
本发明还提供了一种有机发光器件，其包括第一电极、第二电极以及置于所述第一电极、所述第二电极之间的一个或多个有机化合物层，其特征在于，至少一个所述有机化合物层由所述含蒽类衍生物制成。
以及所述含蒽类衍生物的应用，所述含蒽类衍生物在所述有机电致发光器件中用作磷光绿色主体材料、荧光绿色主体材料、空穴注入材料或者空穴传输材料。
对比样品1
下面化合物a用作荧光绿色主体材料，c作为荧光绿色掺杂材料，2-TNATA作为空穴注入层材料，α-NPD(N,N’-二萘基-N,N’-二苯基联苯胺)作为空穴传输层材料使用，制作下面结构的有机发光器件。
ITO/2-TNATA(80nm)/α-NPD(30nm)/化合物a+化合物c(30nm)/Alq3(30nm)/LiF(0.5nm)/Al(60nm)。
阳极是15Ω/cm2 ITO玻璃基板，按照50mmx50mmx0.7mm大小切割，然后在异丙醇和纯净水中超声波15分钟清洗，30分钟UV臭氧洗净使用。在基板上面真空镀膜2-TANATA形成80nm厚度的空穴注入层。在空穴注入层上真空镀膜α-NPD30nm厚度形成空穴传输层。在空穴传输层上真空镀膜化合物a及化合物c（3%涂料），形成30nm厚度的发光层。之后，在发光层上真空镀膜Alq330nm厚度形成电子传输层。在电子传输层上面，在依次真空镀膜LiF0.5nm(电子注入层）和Al60nm(阴极）。
实施例2
将对比样品1中的荧光绿色主体材料采用表1中表示1-48的衍生物替代原化合物a，其余的处理工艺以及条件均相同，制得有机发光器件。
测量对比样品1以及实施例2所得有机发光器件的发光性能，采用KeithleySMU235,评价发光亮度，发光效率，发光颜色。对比样品1以及实施例2进行同样的试验，结果列于表3中。
表3
根据表3所表示，上述的样品在514～524nm波长范围内显示发光颜色为绿色。所述蒽类衍生物发光效率得到了明显的提高。
应当理解的是，本发明的应用不限于上述的举例，对本领域普通技术人员来说，可以根据上述说明加以改进或变换，所有这些改进和变换都应属于本发明所附权利要求的保护范围。

Claims (4)

1.一种含蒽类衍生物，其特征在于，所述含蒽类衍生物为：
、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、或中的一种。
2.一种如权利要求1所述含蒽类衍生物的制备方法，其包括以下步骤：
步骤S1：向反应体系中加入蒽类溴取代化合物、含取代基R的硼酸化合物；
步骤S2：对所述反应体系进行脱气，然后加入催化剂；
步骤S3：升高所述反应体系的反应温度并回流，充分反应，得到所述含蒽类衍生物；
所述蒽类溴取代化合物指的是；
所述取代基R指的是、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、。
3.一种采用如权利要求1所述含蒽类衍生物制成的有机发光器件，其包括第一电极、第二电极以及置于所述第一电极、所述第二电极之间的一个或多个有机化合物层，其特征在于，至少一个所述有机化合物层由如权利要求1所述含蒽类衍生物制成。
4.一种如权利要求1所述含蒽类衍生物的应用，其特征在于，所述含蒽类衍生物在所述有机电致发光器件中用作磷光绿色主体材料、荧光绿色主体材料、空穴注入材料或者空穴传输材料。
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW201024392A (en) * 2008-11-06 2010-07-01 Idemitsu Kosan Co Organic electroluminescence element
US20110065924A1 (en) * 2008-05-14 2011-03-17 Doosan Corporation Preparation of asymmetric anthracene derivatives and organic electroluminescent device using same
CN103022365A (zh) * 2012-12-18 2013-04-03 中国科学院长春应用化学研究所 白色有机电致发光器件及其制备方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110065924A1 (en) * 2008-05-14 2011-03-17 Doosan Corporation Preparation of asymmetric anthracene derivatives and organic electroluminescent device using same
TW201024392A (en) * 2008-11-06 2010-07-01 Idemitsu Kosan Co Organic electroluminescence element
CN103022365A (zh) * 2012-12-18 2013-04-03 中国科学院长春应用化学研究所 白色有机电致发光器件及其制备方法

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