CN108558768A - 一种含咪唑结构的屈类化合物及其有机发光器件 - Google Patents

一种含咪唑结构的屈类化合物及其有机发光器件 Download PDF

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CN108558768A
CN108558768A CN201810297267.XA CN201810297267A CN108558768A CN 108558768 A CN108558768 A CN 108558768A CN 201810297267 A CN201810297267 A CN 201810297267A CN 108558768 A CN108558768 A CN 108558768A
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刘喜庆
蔡辉
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Changchun Haipurunsi Technology Co Ltd
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Abstract

本发明公开了一种含咪唑结构的屈类化合物及其有机发光器件,涉及有机光电材料技术领域。一方面,屈结构因其较高的三线态能级和较宽的能隙,表现出性能优异的蓝光性能;另一方面,分子中通过连接苯并咪唑、萘并咪唑、菲并咪唑或吡啶咪唑基团,增加了结构的电子传输能力,通过连接三芳胺、咔唑、吖啶结构,增强了结构的空穴传输能力,二者的结合使得载流子传输平衡。将其应用于有机发光器件,特别是作为发光层中的蓝色掺杂材料使用,器件表现出驱动电压低、发光效率高的优点,优于现有常用OLED器件。在OLED发光器件中表现出的良好的应用效果,这一点表明其具有良好的产业化前景。

Description

一种含咪唑结构的屈类化合物及其有机发光器件
技术领域
本发明涉及有机光电材料技术领域,尤其涉及一种含咪唑结构的屈类化合物及其有机发光器件。
背景技术
有机电致发光二极管(Organic Light Emitting Diode,OLED)是利用电子和空穴在有机薄膜中复合发光而制备的发光器件,具有以下优点:(1)自主发光,不需要背光源;(2)亮度高,有高的对比度,色彩纯真,几乎没有可视角度的问题;(3)超薄,由非常薄的有机材料涂层和基体材料构成,体积小适用于便携式产品;(4)耗电量非常小,环保节能;(5)响应速度快,是LCD的千分之一;(6)使用温度范围广,在-40℃时仍能正常显示。
一般的有机发光器件(OLED)是由阴极、阳极及阴极和阳极之间插入的有机物层构成的,器件的组成是透明ITO阳极、空穴注入层(TIL)、空穴传输层(HTL)、发光层(EL)、空穴阻挡层(HBL)、电子传输层(ETL)、电子注入层(EIL)、LiAl、阴极等形成。
发光材料是OLED技术的核心,作为三基色之一的蓝色材料尤为关键,这是因为不仅材料本身可以作为发光层得到蓝光器件,还可以向其中掺杂其他发光颜色的材料得到白光发光器件。到目前为止,蓝光材料相对于绿光和红光材料而言发展较为缓慢,这主要由于蓝光有机半导体材料禁带较宽,其电子能级与器件电机能级匹配性较差,影响了载流子的有效注入,使得该类材料很难兼顾效率、稳定性以及色纯度等问题。因此,发展性能优良的蓝光材料,对于有机电致发光器件的发展十分重要。
近几年,咪唑作为一类新型的蓝光材料的构筑单元,引起研究人员的广泛关注,如何设计新的性能更好的含咪唑结构的发光材料进行调节,一直是本领域技术人员亟待解决的问题。
发明内容
本发明的目的是提供一种含咪唑结构的屈类化合物及其有机发光器件。本发明提供的含咪唑结构的屈类化合物热稳定性能高、玻璃化温度高,将该化合物用于发光层中而制成的有机发光器件,表现出驱动电压低、发光效率高的优点,是性能优良的有机发光材料。
本发明提供了一种含咪唑结构的屈类化合物,其分子结构通式如I所示:
其中,A为取代或未取代的C6~C30的芳基、取代或未取代的C2~C30的氨基、取代或未取代的C3~C30的杂芳基中的一种;R选自取代或未取代的C1~C10的烷基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C50的杂芳基中的一种;CY为取代或未取代的C6~C30的芳基。
优选的,所述的A为取代的C2~C30的氨基、取代或未取代的C3~C30的杂芳基中的一种;R选自取代或未取代的C1~C10的烷基、取代或未取代的C6~C30的芳基中的一种。
优选的,所述CY选自苯基、萘基、蒽基、菲基或芘基。
优选的,所述的一种含咪唑结构的屈类化合物,其分子结构通式如II、Ⅲ或Ⅳ所示:
其中,Ar1、Ar2独立地选自取代或未取代的C1~C10的烷基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种;Ra~Rd独立地选自取代或未取代的C1~C10的烷基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种;R选自取代或未取代的C1~C10的烷基、取代或未取代的C6~C30的芳基中的一种;CY选自苯基、萘基、蒽基、菲基或芘基。
优选的,所述的Ar1、Ar2独立地选自以下结构中的一种:
其中,R1~R7独立地选自氢、取代或未取代的C1~C10的烷基、取代或未取代的C1~C10的烷氧基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种;更优选的,R1~R7独立地选自氢、甲基、甲氧基、乙基、异丙基、叔丁基、环己基、苯基、萘基、菲基、蒽基、芘基、苝基、茚基、三亚苯基、呋喃基、噻吩基、吡咯基、二苯并呋喃、二苯并噻吩、咔唑基、芴基、螺二芴基、吖啶基、吩噻嗪基、吩噁嗪基或吲哚基;R8~R11独立地选自取代或未取代的C1~C10的烷基、取代或未取代的C1~C10的烷氧基、取代或未取代的C6~C30的芳基中的一种;更优选的,R8~R11独立地选自甲基、甲氧基、乙基、异丙基、叔丁基、环己基、苯基或萘基;a选自0~3的整数。
再优选,所述的一种含咪唑结构的屈类化合物选自如下所示化学结构中的任意一种:
本发明还提供了一种有机发光器件,包括第一电极、第二电极和置于所述两电极之间的一个或多个有机化合物层,所述的有机化合物层含有任一项所述的一种含咪唑结构的屈类化合物。
优选的,有机化合物层包含发光层,发光层中含有任一项所述的一种含咪唑结构的屈类化合物。
本发明的有益效果:
本发明提供了一种含咪唑结构的屈类化合物,一方面,屈结构因其较高的三线态能级和较宽的能隙,表现出性能优异的蓝光性能;另一方面,分子中通过连接苯并咪唑、萘并咪唑、菲并咪唑或吡啶咪唑基团,增加了结构的电子传输能力,通过连接三芳胺、咔唑、吖啶结构,增强了结构的空穴传输能力,二者的结合使得载流子传输平衡。将其应用于有机发光器件,特别是作为发光层中的蓝色掺杂材料使用,器件表现出驱动电压低、发光效率高的优点,优于现有常用OLED器件。在OLED发光器件中表现出的良好的应用效果,这一点表明其具有良好的产业化前景。
具体实施方式:
下面将结合本发明实施例的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明的保护范围。
本发明所述烷基是指烷烃分子中少掉一个氢原子而成的烃基,其可以为直链烷基、支链烷基、环烷基,实例可包括甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、戊基、异戊基、环戊基、环己基等,但不限于此。
本发明所述芳基是指芳烃分子的芳核碳上去掉一个氢原子后,剩下一价基团的总称,其可以为单环芳基或稠环芳基,实例可包括苯基、联苯基、萘基、蒽基、菲基或芘基等,但不限于此。
本发明所述杂芳基是指芳基中的一个或多个芳核碳被杂原子替代得到的基团的总称,所述杂原子包括但不限于氧、硫或氮原子,所述杂芳基可以为单环杂芳基或稠环杂芳基,实例可包括吡啶基、吡咯基、吡啶基、噻吩基、呋喃基、吲哚基、喹啉基、异喹啉基、苯并噻吩基、苯并呋喃基、二苯并呋喃基、二苯并噻吩基、咔唑基等,但不限于此。
本发明所述氨基是指由一个氮原子和两个氢原子组成,化学式-NH2,其可以为烷氨基或芳胺基,实例可包括-N(CH3)2、-N(CH2CH3)2和如下结构,但不限于此
本发明提供了一种含咪唑结构的屈类化合物,其分子结构通式如I所示:
其中,A为取代或未取代的C6~C30的芳基、取代或未取代的C2~C30的氨基、取代或未取代的C3~C30的杂芳基中的一种;R选自取代或未取代的C1~C10的烷基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C50的杂芳基中的一种;CY为取代或未取代的C6~C30的芳基。
按照本发明,所述取代的烷基、取代的芳基、取代的杂环基,所述取代基独立的选自甲基、乙基、异丙基、叔丁基、苯基、萘基、蒽基、菲基、苯并菲基、苝基、芘基、苯甲基、甲氧基、甲硫基、苯氧基、苯硫基、芴基、9,9-二甲基芴基、二苯胺基、二甲胺基、咔唑基、9-苯基咔唑基、呋喃基、噻吩基、氰基、氟基、氘基、三苯基硅基、三甲基硅基、吩噻嗪基、吩噁嗪基、吖啶基、哌啶基、吡啶基、嘧啶基、联苯基、三联苯基、硝基等,但不限于此。
优选的,所述A为取代的C2~C30的氨基、取代或未取代的C3~C30的杂芳基中的一种;R选自取代或未取代的C1~C10的烷基、取代或未取代的C6~C30的芳基中的一种。
优选的,CY选自苯基、萘基、蒽基、菲基或芘基。
优选的,所述的一种含咪唑结构的屈类化合物,其分子结构通式如II、Ⅲ或Ⅳ所示:
其中,Ar1、Ar2独立地选自取代或未取代的C1~C10的烷基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种;Ra~Rd独立地选自取代或未取代的C1~C10的烷基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种;R选自取代或未取代的C1~C10的烷基、取代或未取代的C6~C30的芳基中的一种;CY选自苯基、萘基、蒽基、菲基或芘基。
优选的,所述的Ar1、Ar2独立地选自以下结构中的一种:
其中,R1~R7独立地选自氢、取代或未取代的C1~C10的烷基、取代或未取代的C1~C10的烷氧基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种;更优选的,R1~R7独立地选自氢、甲基、甲氧基、乙基、异丙基、叔丁基、环己基、苯基、萘基、菲基、蒽基、芘基、苝基、茚基、三亚苯基、呋喃基、噻吩基、吡咯基、二苯并呋喃、二苯并噻吩、咔唑基、芴基、螺二芴基、吖啶基、吩噻嗪基、吩噁嗪基或吲哚基;R8~R11独立地选自取代或未取代的C1~C10的烷基、取代或未取代的C1~C10的烷氧基、取代或未取代的C6~C30的芳基中的一种;更优选的,R8~R11独立地选自甲基、甲氧基、乙基、异丙基、叔丁基、环己基、苯基或萘基;a选自0~3的整数。
再优选,所述的一种含咪唑结构的屈类化合物,选自如下所示化学结构中的任意一种:
本发明的一种含咪唑结构的屈类化合物,其制备路线以6,12-二溴屈开始,与咪唑类结构经由C-C偶联反应得到中间体1,中间1与三芳胺结构、9H-咔唑结构或吖啶结构反应得到目标产物化合物I,涉及的主要化合物如下所示:
本发明对上述反应没有特殊的限制,采用本领域技术人员所熟知的常规反应即可,该制备方法操作简单,易于生产。
本发明还提供了一种有机发光器件,包括第一电极、第二电极和置于所述两电极之间的一个或多个有机化合物层,有机化合物层包含空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层的至少一层;所述有机化合物层中至少一层包含本发明所述的一种含咪唑结构的屈类化合物。
优选的,所述的一种含咪唑结构的屈类化合物可作为有机发光器件中的发光层材料。采用的器件结构优选具体为:NPB用作空穴传输层物质,AND用作主体物质,所述的一种含咪唑结构的屈类化合物用作掺杂物质,TPBi用作电子传输物质,用以制造有以下相同构造的有机发光器件:ITO/NPB/AND:本发明一种含咪唑结构的屈类化合物(掺杂浓度为5wt%)/TPBi/LiF/Al。所述有机电致发光器件可用于平板显示器、照明光源、指示牌、信号灯等应用领域。
[实施例1]化合物A2的合成
化合物a的合成
向装有6,12-二溴屈(16.1g,42.4mmol)的三口瓶中加入100mL THF,氮气保护,-78℃搅拌30分钟,然后加入21mL正丁基锂(2.5M),反应1小时,再加入硼酸三异丙酯14g,低温反应1小时,逐渐恢复室温。后处理过程,体系中加入2M盐酸使溶液PH值为4-5,静置分液,水层用乙酸乙酯萃取,合并有机层,旋干,得化合物a(11.7g,产率80%)。
化合物b的合成
将三叔丁基膦(4.4mL的1.0M的甲苯溶液,1.48g,0.05mmol)、醋酸钯(0.4g,1.83mmol)和叔丁醇钠(22.8g,238mmol)添加至2-溴-1H-苯并咪唑(36.0g,183mmol)和溴苯(29.0g,187mmol)在脱气甲苯(1L)中的溶液,并且将该混合物在回流下加热2小时。将该反应混合物冷却至室温,用甲苯稀释并且经由硅藻土过滤。将该滤液用水稀释,并用甲苯提取,并且合并有机相,将其在真空下进行蒸发。将该残余物经由硅胶进行过滤,并重结晶。得到化合物b(37.3g,产率为75%)。
质谱m/z:271.96(计算值:271.99)。理论元素含量(%)C13H9BrN2:C,57.17;H,3.32;Br,29.26;N,10.26实测元素含量(%):C,57.16;H,3.35;Br,29.26;N,10.24。上述结果证实获得产物为目标产品。
中间体1的合成
将四三苯基膦钯(2.1g,1.83mmol)和碳酸钾(75.7g,549mmol)添加至化合物b(49.8g,183mmol)和化合物a(64.0g,183mmol)在脱气四氢呋喃(500mL)中的溶液,并且将该混合物在回流下加热4小时。将该反应混合物冷却至室温,之后旋除溶剂。经由硅胶柱层析得到中间体1(83.0g,理论值70%)。
质谱m/z:498.05(计算值:498.07)。理论元素含量(%)C31H19BrN2:C,74.56;H,3.83;Br,16.00;N,5.61实测元素含量(%):C,74.54;H,3.83;Br,16.02;N,5.61。上述结果证实获得产物为目标产品。
化合物A2的合成
将三叔丁基膦(4.4mL的1.0M的甲苯溶液,1.48g,0.05mmol)、醋酸钯(0.4g,1.83mmol)和叔丁醇钠(22.8g,238mmol)添加至中间体1(91.1g,183mmol)和二苯胺(31.6g,187mmol)在脱气甲苯(1L)中的溶液,并且将该混合物在回流下加热2小时。将该反应混合物冷却至室温,用甲苯稀释并且经由硅藻土过滤。将该滤液用水稀释,并用甲苯提取,并且合并有机相,将其在真空下进行蒸发。将该残余物经由硅胶进行过滤,并重结晶。得到化合物A2(86.0g,产率为80%)。
质谱m/z:587.26(计算值:587.24)。理论元素含量(%)C43H29N3:C,87.88;H,4.97;N,7.15实测元素含量(%):C,87.88;H,4.98;N,7.13。上述结果证实获得产物为目标产品。
[实施例2]化合物A15的合成
将实施例1中的溴苯换成等摩尔的2-溴-9,9-二甲基芴,其他步骤均与实施例1的合成相同,得到目标产物化合物A15。质谱m/z:703.23(计算值:703.32)。理论元素含量(%)C52H37N3:C,88.73;H,5.30;N,5.97实测元素含量(%):C,88.72;H,5.32;N,5.96。上述结果证实获得产物为目标产品。
[实施例3]化合物A24的合成
将实施例1中的二苯胺换成等摩尔的9H-咔唑,其他步骤均与实施例1的合成相同,得到目标产物化合物A24。质谱m/z:585.27(计算值:585.22)。理论元素含量(%)C43H27N3:C,88.18;H,4.65;N,7.17实测元素含量(%):C,88.19;H,4.65;N,7.16。上述结果证实获得产物为目标产品。
[实施例4]化合物A28的合成
将实施例1中的二苯胺换成等摩尔的吩噁嗪,其他步骤均与实施例1的合成相同,得到目标产物化合物A28。质谱m/z:601.26(计算值:601.22)。理论元素含量(%)C43H27N3O:C,85.83;H,4.52;N,6.98;O,2.66实测元素含量(%):C,85.83;H,4.51;N,6.98;O,2.67。上述结果证实获得产物为目标产品。
[实施例5]化合物B2的合成
中间体2的合成
在氮气的保护下,向三口瓶中加入无水的THF溶液15mL,镁条(1.44g,0.06mol),碘1粒,格式试剂引发后,加入6,12-二溴屈(19.2g,0.05mol)的无水THF溶液50mL,在冰水浴下反应3小时,然后向反应液中滴加4.2mL无水N,N-二甲基甲酰胺后,慢慢升温至室温,继续反应3小时后反应停止。加入1M盐酸,100mL乙酸乙酯萃取,依次用蒸馏水、饱和食盐水清洗有机层,合并有机相并干燥,浓缩柱层析得到12-溴屈-6-甲醛(13.4g,产率为80%)。
在氮气的保护下,向12-溴屈-6-甲醛(2.9g,8.6mmol)、芘-4,5-二酮(2.3g,9.9mmol)、苯胺(3.4g,42.9mmol)的混合物中加入乙酸铵(2.59g,33.6mmol)和乙酸(60mL),加热至回流。2小时后,混合物冷却并过滤。滤饼用氯仿溶解,然后浓缩柱层析得到中间体2(4.0g,产率为75%)。
质谱m/z:622.08(计算值:622.10)。理论元素含量(%)C41H23BrN2:C,78.97;H,3.72;Br,12.81;N,4.49实测元素含量(%):C,78.98;H,3.72;Br,12.83;N,4.47。上述结果证实获得产物为目标产品。
化合物B2的合成
将三叔丁基膦(4.4mL的1.0M的甲苯溶液,1.48g,0.05mmol)、醋酸钯(0.4g,1.83mmol)和叔丁醇钠(22.8g,238mmol)添加至二苯胺(31.6g,187mmol)和中间体2(113.8g,183mmol)在脱气甲苯(1L)中的溶液,并且将该混合物在回流下加热2小时。将该反应混合物冷却至室温,用甲苯稀释并且经由硅藻土过滤。将该滤液用水稀释,并用甲苯提取,并且合并有机相,将其在真空下进行蒸发。将该残余物经由硅胶进行过滤,并重结晶。得到化合物A2(104.1g,产率为80%)。
质谱m/z:711.23(计算值:711.27)。理论元素含量(%)C53H33N3:C,89.42;H,4.67;N,5.90实测元素含量(%):C,89.43;H,4.66;N,5.91。上述结果证实获得产物为目标产品。
[实施例6]化合物B9的合成
将实施例5中的苯胺换成等摩尔的4-氨基联苯,其他步骤均与实施例1的合成相同,得到目标产物化合物B9。质谱m/z:787.23(计算值:787.30)。理论元素含量(%)C59H37N3:C,89.93;H,4.73;N,5.33实测元素含量(%):C,89.96;H,4.73;N,5.31。上述结果证实获得产物为目标产品。
[实施例7]化合物B26的合成
将实施例5中的二苯胺换成等摩尔的9,10-二氢-9,9-二甲基吖啶,其他步骤均与实施例1的合成相同,得到目标产物化合物B26。质谱m/z:751.23(计算值:751.30)。理论元素含量(%)C56H37N3:C,89.45;H,4.96;N,5.59实测元素含量(%):C,89.45;H,4.97;N,5.58。上述结果证实获得产物为目标产品。
[实施例8]化合物C24的合成
将实施例1中的二苯胺换成等摩尔的N-苯基-9H-咔唑,芘-4,5-二酮换成等摩尔的菲醌,其他步骤均与实施例1的合成相同,得到目标产物化合物C24。质谱m/z:685.33(计算值:685.25)。理论元素含量(%)C51H33N3:C,89.32;H,4.56;N,6.13实测元素含量(%):C,89.31;H,4.55;N,6.14。上述结果证实获得产物为目标产品。
[实施例9]化合物D24的合成
将实施例1中的二苯胺换成等摩尔的N-苯基-9H-咔唑,芘-4,5-二酮换成等摩尔的β-萘醌,其他步骤均与实施例1的合成相同,得到目标产物化合物D24。质谱m/z:635.33(计算值:635.24)。理论元素含量(%)C47H29N3:C,88.79;H,4.60;N,6.61实测元素含量(%):C,88.77;H,4.62;N,6.61。上述结果证实获得产物为目标产品。
[实施例10]化合物E3的合成
将实施例1中的二苯胺换成等摩尔的N-苯基-4-联苯胺,其他步骤均与实施例1的合成相同,得到目标产物化合物E3。质谱m/z:635.33(计算值:635.24)。理论元素含量(%)C49H33N3:C,88.66;H,5.01;N,6.33实测元素含量(%):C,88.64;H,5.03;N,6.33。上述结果证实获得产物为目标产品。
[对比应用实施例]
将透明阳极电极ITO基板在异丙醇中超声清洗15分钟,并暴露在紫外光下30分钟,随后用plasma处理10分钟。随后将处理后的ITO基板放入蒸镀设备。首先蒸镀一层70nm的NPB作为空穴传输层,蒸镀速率为0.1nm/s,然后是发光层的蒸镀,混合蒸镀ADN/DPVBi,掺杂浓度为5wt%,蒸镀速率为0.005nm/s,蒸镀厚度为30nm,随后蒸镀50nm的TPBi作为电子传输层,蒸镀速率为0.1nm/s,在电子传输层上依次真空蒸镀LiF和Al作为阴极,厚度为200nm。
[应用实施例]
将透明阳极电极ITO基板在异丙醇中超声清洗15分钟,并暴露在紫外光下30分钟,随后用plasma处理10分钟。随后将处理后的ITO基板放入蒸镀设备。首先蒸镀一层70nm的NPB作为空穴传输层,蒸镀速率为0.1nm/s,然后是发光层的蒸镀,混合蒸镀ADN/本发明的芘类化合物,掺杂浓度为5wt%,蒸镀速率为0.005nm/s,蒸镀厚度为30nm,随后蒸镀50nm的TPBi作为电子传输层,蒸镀速率为0.1nm/s,在电子传输层上依次真空蒸镀LiF和Al作为阴极,厚度为200nm。
上述方法制造的有机发光器件的电子发光特性在下表中表示:
以上结果表明,本发明的一种含咪唑结构的屈类化合物应用于有机发光器件中,尤其是作为发光材料,表现出驱动电压低、发光效率高的优点,是性能良好的有机发光材料。
显然,以上实施例的说明只是用于帮助理解本发明的方法及其核心思想。应当指出,对于所述技术领域的普通技术人员来说,在不脱离本发明原理的前提下,还可以对本发明进行若干改进和修饰,这些改进和修饰也落入本发明权利要求的保护范围内。

Claims (8)

1.一种含咪唑结构的屈类化合物,其特征在于,其分子结构通式如I所示:
其中,A为取代或未取代的C6~C30的芳基、取代或未取代的C2~C30的氨基、取代或未取代的C3~C30的杂芳基中的一种;R选自取代或未取代的C1~C10的烷基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C50的杂芳基中的一种;CY为取代或未取代的C6~C30的芳基。
2.根据权利要求1所述的一种含咪唑结构的屈类化合物,其特征在于,A为取代的C2~C30的氨基、取代或未取代的C3~C30的杂芳基中的一种;R选自取代或未取代的C1~C10的烷基、取代或未取代的C6~C30的芳基中的一种。
3.根据权利要求1所述的一种含咪唑结构的屈类化合物,其特征在于,CY选自苯基、萘基、蒽基、菲基或芘基。
4.根据权利要求1所述的一种含咪唑结构的屈类化合物,其特征在于,其分子结构通式如II、Ⅲ或Ⅳ所示:
其中,Ar1、Ar2独立地选自取代或未取代的C1~C10的烷基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种;Ra~Rd独立地选自取代或未取代的C1~C10的烷基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种;R选自取代或未取代的C1~C10的烷基、取代或未取代的C6~C30的芳基中的一种;CY选自苯基、萘基、蒽基、菲基或芘基。
5.根据权利要求1所述的一种含咪唑结构的屈类化合物,其特征在于,Ar1、Ar2独立地选自以下结构中的一种:
其中,R1~R7独立地选自氢、取代或未取代的C1~C10的烷基、取代或未取代的C1~C10的烷氧基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种;R8~R11独立地选自取代或未取代的C1~C10的烷基、取代或未取代的C1~C10的烷氧基、取代或未取代的C6~C30的芳基中的一种;a选自0~3的整数。
6.根据权利要求1所述的一种含咪唑结构的屈类化合物,其特征在于,选自如下所示化学结构中的任意一种:
7.一种有机发光器件,其特征在于,所述有机发光器件包括阴极、阳极和置于所述两电极之间的一个或多个有机化合物层,所述的有机化合物层含有权利要求1~6任一项所述的一种含咪唑结构的屈类化合物。
8.根据权利要求7中所述的一种有机发光器件,其特征在于,所述有机化合物层包括发光层,发光层中含有权利要求1~6任一项所述的一种含咪唑结构的屈类化合物。
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Publication number Priority date Publication date Assignee Title
CN109761967A (zh) * 2019-03-12 2019-05-17 江苏三月光电科技有限公司 一种基于杂芳基胺类结构的有机化合物及其在oled上的应用
CN109860425A (zh) * 2019-03-12 2019-06-07 江苏三月光电科技有限公司 一种含有覆盖层的有机电致发光装置及用途
CN111675693A (zh) * 2020-05-20 2020-09-18 华南理工大学 一类含吖啶和菲并咪唑的d-a型发光小分子及其在电致发光器件中的应用
CN113801066A (zh) * 2020-08-25 2021-12-17 北京八亿时空液晶科技股份有限公司 咪唑衍生物及其应用

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109761967A (zh) * 2019-03-12 2019-05-17 江苏三月光电科技有限公司 一种基于杂芳基胺类结构的有机化合物及其在oled上的应用
CN109860425A (zh) * 2019-03-12 2019-06-07 江苏三月光电科技有限公司 一种含有覆盖层的有机电致发光装置及用途
CN109860425B (zh) * 2019-03-12 2021-07-13 江苏三月科技股份有限公司 一种含有覆盖层的有机电致发光装置及用途
CN111675693A (zh) * 2020-05-20 2020-09-18 华南理工大学 一类含吖啶和菲并咪唑的d-a型发光小分子及其在电致发光器件中的应用
CN113801066A (zh) * 2020-08-25 2021-12-17 北京八亿时空液晶科技股份有限公司 咪唑衍生物及其应用
CN113801066B (zh) * 2020-08-25 2023-06-23 北京八亿时空液晶科技股份有限公司 咪唑衍生物及其应用

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