CN108727358A - 一种杂环化合物及其有机电致发光器件 - Google Patents

一种杂环化合物及其有机电致发光器件 Download PDF

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CN108727358A
CN108727358A CN201810884499.5A CN201810884499A CN108727358A CN 108727358 A CN108727358 A CN 108727358A CN 201810884499 A CN201810884499 A CN 201810884499A CN 108727358 A CN108727358 A CN 108727358A
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heterocyclic compound
aryl
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张弘
蔡辉
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Changchun Haipurunsi Technology Co Ltd
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Abstract

本发明提供一种杂环化合物及其有机电致发光器件，属于有机光电材料技术领域。该化合物具有式(Ⅰ)所示结构，本发明中的A部分具有容易接受空穴的能力，引入桥连结构，一方面可以增大化合物分子量，使得到的材料具有高玻璃化转变温度并且能够防止结晶的作用，另一方面使得这类化合物在空间立体结构上有一定的扭曲，提高其成膜性。另一端在特定位置引入B类容易接受电子的结构，增加载流子的传输性。将该化合物作为发光层中的主体材料或空穴阻挡层材料使用而制成的有机电致发光器件，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。

Description

一种杂环化合物及其有机电致发光器件
技术领域
本发明涉及有机光电材料技术领域，具体涉及一种杂环化合物及其有机电致发光器件。
背景技术
随着信息产业的进步，传统的显示器已不能满足人们的要求，如：阴极射线管(cathode ray tube,CRT)显示器体积大、驱动电压高；液晶显示器(liquid crystaldisplay,LCD)亮度低、视角窄、工作温度范围小；等离子显示器(plasma display panel,PDP)造价昂贵、分辨率不高、耗电量大。
有机电致发光二极管(organic light-emitting diodes,OLEDs)是以有机物为发光材料的新型电致发光器件，作为一种全新的显示技术在各种性能上拥有现有显示技术无以伦比的优势，凭借着其制备工艺简单、具有全固态、自主发光、亮度高、高分辨率、视角宽(170度以上)、响应速度快、厚度薄、体积小、重量轻、可使用柔性基板、低电压直流驱动(3-10V)、功耗低、工作温度范围宽等，使得它的应用市场十分广泛，如照明系统、通讯系统、车载显示、便携式电子设备、高清晰度显示甚至是军事领域。
有机电致发光材料在近些年内不断实现突破，取得了令人瞩目的进展，对传统的显示材料构成了强有力的挑战。柔性OLED商业化以后，目前世界上与之相关的科研及商业力量都在不遗余力的开展这方面的工作。虽然有机电致发光材料研究已经取得巨大的成果，但是OLED在商业化的过程中还有一些亟待解决的问题。
OLED材料是一种电致发光材料，它的结构是在阴极和阳极之间放入有机物层，有机物层包括发光层和可选的辅助层，辅助层包括：空穴注入层、空穴传输层、空穴阻挡层、电子阻挡层、电子传输层、电子注入层，其中空穴阻挡层可以改进OLED器件的效率和稳定性，因此引起本领域技术人员的极大关注。
发明内容
本发明的目的是提供一种杂环化合物及其有机电致发光器件，本发明中的杂环化合物可以有效的接受空穴，而引入桥连结构，增大化合物分子量，使得到的材料具有高玻璃化转变温度并且能够防止结晶的作用；在侨联结构旁边引入三嗪类结构，增加载流子传输能力，增大三线态能级，能隙差变大。将该化合物作为发光层中的主体材料或者空穴阻挡层使用而制成的有机电致发光器件，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。
本发明首先提供一种杂环化合物，具有如下通式(Ⅰ)所示结构：
A由通式(Ⅱ)表示：
其中R1、R2独立地选自取代或未取代的C1-C30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；X相同或者不同的选自CR3或者N，其中R3选自氢、取代或未取代的C1-C30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，并且至少一个为N。
L选自单键、取代或未取代的C6-C30的二价芳基、取代或未取代的C3～C30的二价杂芳基中的一种。
B由通式(Ⅲ)表示：
其中X1、X2独立地选自CR5R6、NR7、S、O或单键，其中R5、R6、R7独立地选自氢、取代或未取代的C1-C30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；环F为苯环或萘环；R4为环F上的取代基，选自取代或未取代的C1-C30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。
优选的，所述A选自如下所示通式中的任意一种：
其中R1、R2、R3独立地选自氢、取代或未取代的C1-C15烷基、取代或未取代的C6-C15的芳基、取代或未取代的C3～C15的杂芳基中的一种。
优选的，所述L选自单键或者如下所示结构中的任意一种：
优选的，所述的B选自如下所示通式中的任意一种：
其中R5、R6、R7独立地选自氢、取代或未取代的C1-C15的烷基、取代或未取代的C6-C15的芳基、取代或未取代的C3～C15的杂芳基中的一种；环F为苯环或萘环；R4为环F上的取代基，选自取代或未取代的C1-C15烷基、取代或未取代的C6-C15的芳基、取代或未取代的C3～C15的杂芳基中的一种。
优选的，所述的杂环化合物选自如下所示结构中的任意一种：
。
本发明还提供一种有机电致发光器件，所述有机电致发光器件包括阳极、阴极以及位于所述阳极与所述阴极之间的若干个有机功能层，所述的有机功能层含有所述的杂环化合物任意一种或至少两种的组合。
优选的，所述有机功能层包括发空穴阻挡层，所述空穴阻挡层包括权利要求中任一项所述的杂环化合物的任意一种或至少两种的组合。
优选的，所述有机功能层包括发光层，所述发光层包括所述的杂环化合物的任意一种或至少两种的组合。
优选的，所述杂环化合物在发光层中用作主体材料。
本发明的有益效果：
为了改善现有技术中OLED器件的效率和稳定性，使用寿命短等问题，本发明首先提供一种杂环结构的化合物，该化合物具有式(Ⅰ)所示结构。本发明中的结构B具有容易接受空穴的能力，引入桥连结构，一方面可以增大化合物分子量，使得到的材料具有高玻璃化转变温度并且能够防止结晶的作用，另一方面使得这类化合物在空间立体结构上有一定的扭曲，提高其成膜性。另一端在特定位置引入吡啶、嘧啶和三嗪类容易接受电子的结构，增加载流子的传输性。此外，L打断了两部分相互作用，使两个吸电子和拉电子部分局部化，并且控制共轭体系的流动，使得化合物具有两极性，使得激子向相邻的其他有机物层扩散的最小化，将该化合物作为发光层中的空穴阻挡层或主体材料使用而制成的有机电致发光器件，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。
具体实施方式
为了进一步理解本发明，下面结合实施例对本发明优选实施方案进行描述，但是应当理解，这些描述只是为进一步说明本发明的特征和优点，而不是对本发明权利要求的限制。
需要说明的是，除非另有规定，本发明所使用的科技术语的含义与本领域技术人员通常所理解的含义相同。
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、支链烷基或环烷基，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、氮或硅原子，所述杂芳基可以为单环或稠环，实例可包括吡啶基、吩噻嗪基、吩恶嗪基、嘧啶基、苯并嘧啶基、咔唑基、三嗪基、苯并噻唑基、苯并咪唑基、吖啶基等，但不限于此。
本发明所述的二价芳基是指芳烃分子的两个芳核碳上各去掉一个氢原子后，剩下的二价基团的总称，其可以为二价单环芳基或二价稠环芳基，例如可选自亚苯基、亚联苯基、亚三联苯基、亚萘基、亚蒽基、亚菲基、亚芘基、亚芴基或亚苯并菲基等，但不限于此。
本发明所述二价杂芳基是指二价芳基中的一个或多个芳核碳被杂原子替换得到的基团的总称，所述杂原子包括但不限于氧、硫或氮原子，所述二价杂芳基可以为二价单环杂芳基或二价稠环杂芳基，例如可以选自亚吡啶基、亚喹啉基、亚咔唑基、亚噻吩基、亚苯并噻吩基、亚呋喃基、亚苯并呋喃基、亚嘧啶基、亚苯并嘧啶基、亚咪唑基或亚苯并咪唑基等，但不限于此。
本发明所述取代的烷基、取代的芳基、取代的杂芳基等中，所述取代基可以独立的选自氘原子、氰基、硝基、卤素原子、C1-C10的烷基、C1-C10的烷氧基、C1-C10的烷硫基、C1-C30的芳基、C1-C30的芳氧基、C1-C30的芳硫基、C3-C30的杂芳基，C1～C30的硅烷基、C2～C10的烷胺基、C6～C30的芳胺基等，例如氘原子、氰基、硝基、卤素、甲基、乙基、丙基、异丙基、叔丁基、甲氧基、甲硫基、苯基、联苯基、三联苯基、萘基、蒽基、菲基、苯并菲基、苝基、芘基、芴基、9,9-二甲基芴基、苯甲基、苯氧基、苯硫基、二苯胺基、二甲胺基、咔唑基、9-苯基咔唑基、呋喃基、噻吩基、三苯基硅基、三甲基硅基、三氟甲基、吩噻嗪基、吩噁嗪基、吖啶基、哌啶基、吡啶基、吡嗪基、三嗪基、嘧啶基等，但不限于此。
本发明首先提供一种杂环化合物，具有如式(I)所示的结构式：
A由通式(Ⅱ)表示：
其中R1、R2独立地选自取代或未取代的C1-C30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；X相同或者不同的选自CR3或者N，其中R3选自氢、取代或未取代的C1-C30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，并且至少一个为N。
L选自单键、取代或未取代的C6-C30的二价芳基、取代或未取代的C3～C30的二价杂芳基中的一种；
B由通式(Ⅲ)表示：
其中X1、X2独立地选自CR5R6、NR7、S、O或单键，其中R5、R6、R7独立地选自氢、取代或未取代的C1-C30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；环F为苯环或萘环；R4为环F上的取代基，选自取代或未取代的C1-C30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。
优选的，所述A选自如下所示通式中的任意一种：
其中R1、R2、R3独立地选自氢、取代或未取代的C1-C15烷基、取代或未取代的C6-C15的芳基、取代或未取代的C3～C15的杂芳基中的一种。
优选的，所述L选自单键或者如下所示结构中的任意一种：
优选的，所述的B选自如下所示通式中的任意一种：
其中R5、R6、R7独立地选自氢、取代或未取代的C1-C15的烷基、取代或未取代的C6-C15的芳基、取代或未取代的C3～C15的杂芳基中的一种；环F为苯环或萘环；R4为环F上的取代基，选自取代或未取代的C1-C15烷基、取代或未取代的C6-C15的芳基、取代或未取代的C3～C15的杂芳基中的一种。
优选的，所述的杂环化合物选自如下所示结构中的任意一种：
。
以上列举了本发明所述杂环化合物的一些具体的结构形式，但本发明并不局限于所列的这些化学结构，凡是以式(I)所示结构为基础，各种取代基为如上所限定的基团都应该包含在内。
本发明所述杂环化合物，其制备方法如下：
含有A的二溴化物和含有L的硼酸酯化合物偶联，将所得化合物与B的溴化物偶联得到所述杂环化合物。
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。
本发明还提供一种有机电致发光器件，所述有机电致发光器件为本领域技术人员所熟知的有机电致发光器件即可，本发明所述有机电致发光器件包括阳极、阴极以及位于所述阳极与阴极之间的若干个有机功能层，所述有机功能层中包括所述的杂环化合物任意一种或至少两种的组合。所述有机功能层可以包括空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层与电子注入层中的至少一层，优选所述有机功能层包括空穴阻挡层，所述空穴阻挡层包括所述的杂环化合物的任意一种或至少两种的组合，优选所述有机功能层包括发光层，所述发光层包括所述的杂环化合物的任意一种或至少两种的组合，更优选所述杂环化合物在发光层中用作主体材料。
本发明对以下实施例中所采用的原料的来源没有特别的限制，可以为市售产品或采用本领域技术人员所熟知的制备方法制备得到。
实施例1：
化合物1的制备
化合物1-3的制备
在氮气的保护下，向2L反应釜中加入1-1(35.92g，100.08mmol)，1-2(28.19g，100.08mmol)，碳酸钾(1.24g，9.00mmol)，甲苯200mL搅拌。反应釜内温度升到70℃，加入Pd(PPh3)4(1.04g，0.90mmol)，蒸馏水100mL搅拌，搅拌回流11h，充分反应。加入70mL蒸馏水终止反应后，减压过滤，用蒸馏水洗涤固体，然后用丙酮，甲苯，THF来重结晶，得到固体后再升华，甲苯重结晶，得到中间体1-3 31.13g，产率为80.44％。
化合物1的制备
与化合物1-3的制备方法相同，得到化合物1 38.03g，产率75％。质谱m/z：507.14(计算值：507.15)。理论元素含量(％)C33H21N3OS：C，78.08；H，4.17；N，8.28；O，3.15；S，6.32实测元素含量(％)：C，78.07；H，4.16；N，8.27；O，3.14；S，6.33上述证实获得产物为目标产物1。
实施例2:
化合物11的制备
化合物11的制备
将实施例1中的1-4替换为如上所示11-4，得到化合物11。质谱m/z：501.22(计算值：501.23)。理论元素含量(％)C36H27N3：C，86.20；H，5.43；N，8.38实测元素含量(％)：C，90.42；H，5.28；N，4.31上述证实获得产物为目标产物11。
实施例3:
化合物20的制备
化合物20的制备
将实施例1中的1-4替换为如上所示20-4，得到化合物20。质谱m/z：623.24(计算值：623.25)。理论元素含量(％)C46H29N3：C，88.58；H，4.69；N，6.74实测元素含量(％)：C，88.57；H，4.68；N，6.75。上述证实获得产物为目标产物20。
实施例4:
化合物38的制备
化合物38的制备
将实施例1中的1-1替换为如上所示38-1，1-4替换为如上所示38-4，得到化合物38。质谱m/z：576.26(计算值：576.27)。理论元素含量(％)C43H32N2：C，89.55；H，5.59；N，4.86实测元素含量(％)：C，89.56；H，5.58；N，4.85。上述证实获得产物为目标产物38。
实施例5:
化合物52的制备
化合物52的制备
将实施例1中的1-2替换为如上所示52-2，1-4替换为如上所示52-4，得到化合物52。质谱m/z：620.29(计算值：620.28)。理论元素含量(％)C44H36N4：C，85.13；H，5.85；N，9.03实测元素含量(％)：C，85.14；H，5.86；N，9.02。上述证实获得产物为目标产物52。
实施例6:
化合物68的制备
化合物68的制备
将实施例1中的1-1替换为如上所示68-1，1-2替换为如上所示68-2，1-4替换为如上所示68-4，得到化合物68。质谱m/z：621.25(计算值：621.26)。理论元素含量(％)C48H31N：C，92.72；H，5.03；N，2.25实测元素含量(％)：C，92.72；H，5.03；N，2.25。上述证实获得产物为目标产物68。
实施例7:
化合物79的制备
化合物79的制备
将实施例1中的1-2替换为如上所示79-2，1-4替换为如上所示79-4，得到化合物79。质谱m/z：591.23(计算值：591.24)。理论元素含量(％)C42H29N3O：C，85.25；H，4.94；N，7.10；O，2.70实测元素含量(％)：C，85.26；H，4.95；N，7.11；O，2.71。上述证实获得产物为目标产物79。
实施例8:
化合物98的制备
化合物98的制备
将实施例1中的1-2替换为如上所示98-2，1-4替换为如上所示98-4，得到化合物98。质谱m/z：577.25(计算值：577.26)。理论元素含量(％)C42H31N3：C，87.32；H，5.41；N，7.27实测元素含量(％)：C，87.33；H，5.42；N，7.28。上述证实获得产物为目标产物98。
实施例9:
化合物110的制备
化合物110的制备
将实施例1中的1-2替换为如上所示110-2，1-4替换为如上所示110-4，得到化合物110。质谱m/z：537.20(计算值：537.21)。理论元素含量(％)C36H25F2N3：C，80.43；H，4.69；F，7.07；N，7.82实测元素含量(％)：C，80.42；H，4.68；F，7.06；N，7.83。上述证实获得产物为目标产物110。
实施例10:
化合物121的制备
化合物121的制备
将实施例1中的1-1替换为如上所示121-1，1-2替换为如上所示121-2，1-4替换为如上所示121-4，得到化合物121。质谱m/z：673.28(计算值：673.29)。理论元素含量(％)C52H35N：C，92.69；H，5.24；N，2.08实测元素含量(％)：C，92.68；H，5.23；N，2.07。上述证实获得产物为目标产物121。
实施例11:
化合物129的制备
化合物129的制备
将实施例1中的1-1替换为如上所示129-1，1-2替换为如上所示129-2，1-4替换为如上所示129-4，得到化合物129。质谱m/z：606.21(计算值：606.22)。理论元素含量(％)C43H30N2S：C，85.12；H，4.98；N，4.62；S，5.28实测元素含量(％)：C，85.13；H，4.97；N，4.63；S，5.29。上述证实获得产物为目标产物129。
实施例12:
化合物150的制备
化合物150的制备
将实施例1中的1-1替换为如上所示150-1，1-2替换为如上所示150-2，1-4替换为如上所示150-4，得到化合物150。质谱m/z：625.25(计算值：625.26)。理论元素含量(％)C46H31N3：C，88.29；H，4.99；N，6.72实测元素含量(％)：C，88.28；H，4.98；N，6.73。上述证实获得产物为目标产物150。
[对比应用实施例]
将透明阳极电极ITO基板分别用去离子水、丙酮、乙醇超声清洗各15分钟，然后在等离子清洗器中清洗2分钟，干燥并且抽真空至5×10-5Pa。随后将处理后的ITO基板进行蒸镀。逐层蒸镀空穴注入层HAT-CN/50nm、蒸镀空穴传输层NPB/30nm、蒸镀主体CBP：掺杂Ir(ppy)3 10％混合/30nm、然后蒸镀电子传输层TPBi/30nm、电子注入层LiF/0.5nm、阴极Al/200nm。
[应用实施例1-12]
将对比应用实施例中的CBP换成实施例1-12中的所示化合物1、11、20、38、52、68、79、98、110、121、129、150。
表1为本发明实施例制备的化合物以及比较物质制备的发光器件的发光特性测试结果。
[表1]发光器件的发光特性测试
[应用实施例13-24]
将对比应用实施例的发光层和电子传输层中增加空穴阻挡层，蒸镀厚度为10nm，使用的化合物为实施例1-12中的所示化合物1、11、20、38、52、68、79、98、110、121、129、150。
表2为本发明实施例制备的化合物以及比较物质制备的发光器件的发光特性测试结果。
[表2]发光器件的发光特性测试
以上结果表明，本发明的化合物作为绿光主体材料或者空穴阻挡材料，应用于有机电致发光器件中，发光效率高，是性能良好的有机发光材料。
虽然本发明用示范性实施方案进行了特别的描述，但应该理解在不偏离权利要求所限定的本发明的精神与范围的情况下，本领域普通技术人员可对其进行各种形式和细节上的改变。

Claims (9)

1.一种杂环化合物，其特征在于，具有如下通式(Ⅰ)所示结构：
A由通式(Ⅱ)表示：
其中R1、R2独立地选自取代或未取代的C1-C30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；X相同或者不同的选自CR3或者N，其中R3选自氢、取代或未取代的C1-C30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，并且至少一个为N；
L选自单键、取代或未取代的C6-C30的二价芳基、取代或未取代的C3～C30的二价杂芳基中的一种；
B由通式(Ⅲ)表示：
其中X1、X2独立地选自CR5R6、NR7、S、O或单键，其中R5、R6、R7独立地选自氢、取代或未取代的C1-C30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；环F为苯环或萘环；R4为环F上的取代基，选自取代或未取代的C1-C30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。
2.根据权利要求1所述杂环化合物，其特征在于，所述的A选自如下所示通式中的任意一种：
其中R1、R2、R3独立地选自氢、取代或未取代的C1-C15烷基、取代或未取代的C6-C15的芳基、取代或未取代的C3～C15的杂芳基中的一种。
3.根据权利要求1所述杂环化合物，其特征在于，所述的L选自单键或者如下所示结构中的任意一种：
4.根据权利要求1所述杂环化合物，其特征在于，所述的B选自如下所示通式中的任意一种：
其中R5、R6、R7独立地选自氢、取代或未取代的C1-C15的烷基、取代或未取代的C6-C15的芳基、取代或未取代的C3～C15的杂芳基中的一种；环F为苯环或萘环；R4为环F上的取代基，选自取代或未取代的C1-C15烷基、取代或未取代的C6-C15的芳基、取代或未取代的C3～C15的杂芳基中的一种。
5.根据权利要求1所述杂环化合物，其特征在于所述的杂环化合物选自如下所示结构中的任意一种：
6.一种有机电致发光器件，包括阳极、阴极以及位于所述阳极与所述阴极之间的若干个有机功能层，其特征在于,所述有机功能层中包括权利要求1～5任一项所述的杂环化合物任意一种或至少两种的组合。
7.根据权利要求6所述的一种有机电致发光器件，其特征在于，所述有机功能层包括发空穴阻挡层，所述空穴阻挡层包括权利要求1～5任一项所述的杂环化合物的任意一种或至少两种的组合。
8.根据权利要求5所述的一种有机电致发光器件，其特征在于，所述有机功能层包括发光层，所述发光层包括权利要求1～5任一项所述的杂环化合物的任意一种或至少两种的组合。
9.根据权利要求7所述的一种有机电致发光器件，其特征在于，所述杂环化合物在发光层中用作主体材料。
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CN111620853A (zh) * 2019-02-28 2020-09-04 北京夏禾科技有限公司 有机电致发光材料及其器件
CN114685427A (zh) * 2020-12-28 2022-07-01 常州强力昱镭光电材料有限公司 一种喹啉联吡啶化合物及其在有机电致发光元件中的应用

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CN111620853A (zh) * 2019-02-28 2020-09-04 北京夏禾科技有限公司 有机电致发光材料及其器件
US11708356B2 (en) 2019-02-28 2023-07-25 Beijing Summer Sprout Technology Co., Ltd. Organic electroluminescent materials and devices
CN111620853B (zh) * 2019-02-28 2023-07-28 北京夏禾科技有限公司 有机电致发光材料及其器件
CN114685427A (zh) * 2020-12-28 2022-07-01 常州强力昱镭光电材料有限公司 一种喹啉联吡啶化合物及其在有机电致发光元件中的应用
CN114685427B (zh) * 2020-12-28 2023-12-22 常州强力昱镭光电材料有限公司 一种喹啉联吡啶化合物及其在有机电致发光元件中的应用

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