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CN111689889A - 芳香胺化合物及其应用 - Google Patents

芳香胺化合物及其应用 Download PDF

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CN111689889A
CN111689889A CN202010704032.5A CN202010704032A CN111689889A CN 111689889 A CN111689889 A CN 111689889A CN 202010704032 A CN202010704032 A CN 202010704032A CN 111689889 A CN111689889 A CN 111689889A
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CN111689889B (zh
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范洪涛
王湘成
向传义
何为
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Shanghai Yaoyi Electronic Technology Co ltd
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Abstract

本发明公开了芳香胺化合物及其应用，属于有机电致发光技术领域。该芳香胺化合物具有下式所示的通式结构：
Figure DDA0002594015080000011
X选自O、S或‑NR‑，且R1、R2、R3、R4和R分别独立地选自氢、氘、取代或未取代的环形成碳数为6‑30的芳基、取代或未取代的环形成原子数为5‑30的杂芳基、取代或未取代的碳数为1‑30的烷基、取代或未取代的碳数为1‑30的氟烷基、取代或未取代的环形成碳数为3‑30的环烷基、取代或未取代的碳数为7‑30的芳烷基，其作为有机电致发光器件内空穴传输材料。本发明的芳香胺化合物由于萘并杂环结构的加入，能够有效提升OLED器件的空穴传输能力，从而提高器件的光效率和使用寿命。

Description

芳香胺化合物及其应用
技术领域
本发明属于有机电致发光领域，具体涉及芳香胺化合物及其在有机电致发光器件和显示中的应用。
背景技术
OLED可固态发光，广泛用于显示、照明等领域，OLED器件是由阳极、阴极以及之间的有机材料构成，空穴由阳极注入并向发光层传输、电子由阴极注入并向发光层传输，为了达到最好的发光性能，往往要平衡空穴和电子进入发光层的量。合适的空穴传输材料对OLED发光性能影响很大，而普通的含胺类空穴传输材料的空穴注入能力比较差，空穴注入量少，导致器件电压高、效率低，芳香胺化合物被广泛用作空穴传输材料，但空穴传输能力仍有待改善。
发明内容
为克服现有技术的上述不足，本发明提供一种具有萘并杂环的芳香胺化合物，用作OLED器件的空穴传输材料能够有效提升OLED器件的空穴传输能力，从而提升器件性能，所述芳香胺化合物具有如通式(Ⅰ)所示的化学结构：
Figure BDA0002594015060000011
其中，X选自O、S或-NR-；
R1、R2、R3、R4和R分别独立地选自氢、氘、取代或未取代的环形成碳数为6-30的芳基、取代或未取代的环形成原子数为5-30的杂芳基、取代或未取代的碳数为1-30的烷基、取代或未取代的碳数为1-30的氟烷基、取代或未取代的环形成碳数为3-30的环烷基、取代或未取代的碳数为7-30的芳烷基。
根据本发明的一些实施方式，所述芳香胺化合物选自如C1至C36任一所示化学结构：
Figure BDA0002594015060000021
Figure BDA0002594015060000031
本发明提供了上述任一所述芳香胺化合物作为有机电致发光器件内空穴传输材料的用途。
根据本发明的一些实施方式，所述有机电致发光器件为顶发射结构，依次包括第一电极、空穴注入层、第一空穴传输层、第二空穴传输层、发光层、空穴阻挡层、电子传输层、第二电极和盖帽层；其中，
如通式(Ⅰ)所示化学结构的任一所述芳香胺化合物作为第一空穴传输层和/或第二空穴传输层。
本发明还提供一种显示面板，包括任一所述有机电致发光器件。
本发明还提供了一种显示装置，包括上述任一所述的显示面板。
本发明包含所述有机电致发光器件的显示面板或显示装置具有如下优势：发光效率高，驱动电压低和使用寿命长。
与现有技术相比，本发明中作为空穴传输材料的芳香胺化合物由于萘并杂环结构的加入，能够有效提升OLED器件的空穴传输能力，从而提高器件的光效率和使用寿命。
附图说明
图1是OLED器件的结构示意图。
具体实施方式
下面通过实施例和对比例进一步说明本发明，这些实施例只是用于说明本发明，本发明不限于以下实施例。凡是对本发明技术方案进行修改或者等同替换，而不脱离本发明技术方案的范围，均应涵盖在本发明的保护范围中。
本发明提供的芳香胺化合物，具有如通式(Ⅰ)所示的化学结构：
Figure BDA0002594015060000041
其中，X选自O、S或-NR-；
R1、R2、R3、R4和R分别独立地选自氢、氘、取代或未取代的环形成碳数为6-30的芳基、取代或未取代的环形成原子数为5-30的杂芳基、取代或未取代的碳数为1-30的烷基、取代或未取代的碳数为1-30的氟烷基、取代或未取代的环形成碳数为3-30的环烷基、取代或未取代的碳数为7-30的芳烷基，上述芳香胺化合物在一些实施方式中可选自如C1至C36任一所示化学结构：
Figure BDA0002594015060000051
Figure BDA0002594015060000061
Figure BDA0002594015060000071
本发明还提供上述芳香胺化合物作为有机电致发光器件内空穴传输材料的用途；在一些实施方式，该有机电致发光器件可为顶发射结构，且依次包括第一电极、空穴注入层、第一空穴传输层、第二空穴传输层、发光层、空穴阻挡层、电子传输层、第二电极和盖帽层；其中，如上述通式(Ⅰ)所示化学结构的芳香胺化合物作为第一空穴传输层和/或第二空穴传输层。
本发明还提供一种包括上述有机电致发光器件的显示面板。
本发明还提供一种包括上述显示面板的显示装置。
以下合成实施例1-5示例性地描述了如上述化合物C1、C2、C7、C19和C28的合成，其中未注明制备方法的原料均为市售商品。
合成实施例1
本实施例合成化合物C1(1-1)，合成路线如下所示：
Figure BDA0002594015060000072
具体的制备步骤为：
M-1的合成:向三口瓶中依次加入M-1A(100g,553.6mmol),M-1B(102g,553.6mmol)和1,4-二氧六环(1.00L)，置换三次氮气，边搅拌边向三口瓶中滴加浓硫酸(33.8mL,609mmol)，完毕后开启加热，设置外温100℃，回流反应10hrs后冷却反应液体，倒入水(2.00L)中，并用甲苯(1.00L×2)萃取，有机相经饱和NaCl水溶液(1.00L×3)洗涤后过柱纯化，得M-1(155.2g,85％)，MS(70eV,EI+):m/z:329.10。
M-2的合成：向三口瓶中依次加入M-1(100g，303.2mmol)，甲苯(1.00L)和DDQ(77.1g，333.5mmol)，置换氮气三次，开启搅拌和加热，设置外温120℃，回流反应5hrs，向加入饱和NaOH水溶液(200mL)，继续反应1hr后，降温，过滤，滤液经饱和NaCl水溶液(300mL×3)洗涤后，过柱纯化，得M-2(79.5g，80％)，MS(70eV,EI+):m/z:327.08。
M-3的合成：边搅拌边向三口瓶中依次加入甲苯(800mL)，M-2(79.0g，241mmol)，溴苯(37.9g，241mmol)，叔丁醇钠(57.9g，602mmol)，Pd2dba3(2.20g，2.41mmol)和三叔丁基膦(15.0mL，10％甲苯溶液，6.02mmol)，置换氮气三次后，开启加热，设置外温120℃，回流反应3hrs后，降温，过滤，滤液经柱层析纯化，得M-3(87.6g，90％)，MS(70eV,EI+):m/z:403.11。
1-1的合成：边搅拌边向三口瓶中加入甲苯(100mL)，无水乙醇(50mL)，水(50mL)，M-3(20.0g，49.5mmol)，M-3A(14.3g，49.5mmol)，K2CO3(13.7g，99.0mmol)，Pd(PPh3)4(575mg，0.49mmol)，置换氮气三次，开启加热，设置外温100℃，回流反应3hrs后降温，分液，有机相经饱和NaCl水溶液(100mL×3)洗涤后，柱层析纯化，得1-1(25.8g，85％)，MS(70eV,EI+):m/z:612.26；1H NMR(CDCl3,400Hz):δ8.12-8.23(m,4H),7.89(s,1H),7.37-7.62(m,15H),7.01-7.24(m,12H)。
合成实施例2
采用如实施例1得到的M-3合成本实施例的化合物C2(1-2)，合成路线如下所示：
Figure BDA0002594015060000081
具体的制备步骤为：
1-2的合成：边搅拌边向三口瓶中加入甲苯(100mL)，无水乙醇(50mL)，水(50mL)，M-3(20.0g，49.5mmol)，M-3B(21.9g，49.5mmol)，K2CO3(13.7g，99.0mmol)，Pd(PPh3)4(575mg，0.49mmol)，置换氮气三次，开启加热，设置外温100℃，回流反应3hrs后降温，分液，有机相经饱和NaCl水溶液(100mL×3)洗涤后，柱层析纯化，得1-2(31.1g，82％)，MS(70eV,EI+):m/z:764.32；1H NMR(CDCl3,400Hz):δ8.12-8.30(m,4H),7.60-7.75(m,6H),7.31-7.58(m,30H)。
合成实施例3
采用实施例1得到的M-3合成本实施例的化合物C7(1-3)，合成路线如下所示：
Figure BDA0002594015060000091
具体的制备步骤为：
M-4的合成：边搅拌边向三口瓶中加入甲苯(100mL)，无水乙醇(50mL)，水(50mL)，M-3(20.0g，49.5mmol)，M-3C(7.74g，49.5mmol)，K2CO3(13.7g，99.0mmol)，Pd(PPh3)4(575mg，0.49mmol)，置换氮气三次，开启加热，设置外温100℃，回流反应3hrs后降温，分液，有机相经饱和NaCl水溶液(100mL×3)洗涤后，柱层析纯化，得M-4(19.7g，83％)，MS(70eV,EI+):m/z:479.14。
1-3的合成：边搅拌边向三口瓶中依次加入甲苯(190mL)，M-4(19.0g，39.58mmol)，M-4A(12.7g，39.58mmol)，叔丁醇钠(7.61g，79.17mmol)，Pd2dba3(365mg，0.40mmol)和三环己基膦(280mg，0.99mmol)，置换氮气三次后，开启加热，设置外温120℃，回流反应3hrs后，降温，过滤，滤液经柱层析纯化，得1-3(30.0g，90％)，MS(70eV,EI+):m/z:840.35；1H NMR(CDCl3,400Hz):δ8.12-8.30(m,4H),7.89(s,1H)7.34-7.75(m,35H),7.25(s,4H)。
合成实施例4
本实施例合成化合物C19(2-1)，合成路线如下所示：
Figure BDA0002594015060000101
具体的制备步骤为：
M-5的合成:边搅拌边向三口瓶中依次加入乙腈(500mL)，M-5A(50.0g，281.5mmol)，M-5B(70.7g，281.5mmol)，碳酸铯(183.5g，563mmol)，置换氮气三次后，开启加热，设置外温100℃，回流反应10hrs后，降温，反应液倒入水(500mL)中淬灭,用乙酸乙酯(200mL×2)萃取,有机相浓缩后经柱层析纯化，得M-5(99.2g，86％)，MS(70eV,EI+):m/z:407.99。
M-6的合成：边搅拌边向三口瓶中依次加入甲苯(200mL)，M-5(20.0g，48.82mmol)，叔丁醇钠(9.38g，97.63mmol)，Pa2(dba)3(447mg，0.488mmol)，P(t-Bu)3(2.0g，10％甲苯溶液，0.989mmol)，置换氮气三次后，开启加热，设置外温120℃，回流反应2hrs后，降温，过滤，滤液经柱层析纯化，得M-6(13.24g，82.5％)，MS(70eV,EI+):m/z:328.07。
2-1的合成：边搅拌边向三口瓶中加入甲苯(40mL)，无水乙醇(20mL)，水(20mL)，M-6(10.0g，30.41mmol)，M-6A(8.79g，30.41mmol)，K2CO3(6.31g，45.62mmol)，Pd(PPh3)4(351mg，0.3mmol)，置换氮气三次，开启加热，设置外温100℃，回流反应3hrs后降温，分液，有机相经饱和NaCl水溶液(50mL×3)洗涤后，柱层析纯化，得2-1(15.53g，95％)，MS(70eV,EI+):m/z:537.21；1H NMR(CDCl3,400Hz):δ8.23(d,1H),7.75-7.88(m,6H),7.37-7.55(m,10H),7.00-7.24(m,10H)。
合成实施例5
本实施例合成化合物C28(2-2)，合成路线如下所示：
Figure BDA0002594015060000111
具体的制备步骤为：
M-7的合成：边搅拌边向三口瓶中加入甲苯(200mL)，无水乙醇(100mL)，水(100mL)，M-7A(50.0g，194.62mmol)，M-7B(60.43g，194.62mmol)，K2CO3(40.35g，292mmol)，Pd(PPh3)4(2.25g，1.95mmol)，置换氮气三次，开启加热，设置外温100℃，回流反应3hrs后降温，分液，有机相经饱和NaCl水溶液(100mL×3)洗涤后，柱层析纯化，得M-7(70.1g，91％)，MS(70eV,EI+):m/z:393.94。
M-8的合成：向三口瓶中加入甲烷磺酸(350mL)和M-7(70.0g，176.9mmol)，置换氮气三次，开启加热，设置外温150℃，反应12hrs后，降温，反应液倒入始终水(1L)和甲苯(1L)混合液中，搅拌均匀，分液，有机相经饱和NaCl水溶液(300mL×3)洗涤后柱层析纯化，得M-8(59.8g，)，MS(70eV,EI+):m/z:361.92。
M-9的合成：向三口瓶中依次加入M-8(50.0g，137.49mmol)，甲苯(500mL)和DDQ(34.33g，151.24mmol)，置换氮气三次，开启搅拌和加热，设置外温120℃，回流反应5hrs，向加入饱和NaOH水溶液(200mL)，继续反应1hr后，降温，过滤，滤液经饱和NaCl水溶液(300mL×3)洗涤后，过柱纯化，得M-9(43.26g，90.5％)，MS(70eV,EI+):m/z:345.92。
M-10的合成：边搅拌边向三口瓶中加入甲苯(160mL)，无水乙醇(80mL)，水(80mL)，M-9(40.0g，115.06mmol)，苯硼酸(14.03g，115.06mmol)，K2CO3(23.85g，172.6mmol)，Pd(PPh3)4(1.33g，1.15mmol)，置换氮气三次，开启加热，设置外温100℃，回流反应3hrs后降温，分液，有机相经饱和NaCl水溶液(100mL×3)洗涤后，柱层析纯化，得M-10(37.7g，95％)，MS(70eV,EI+):m/z:344.04。
2-2的合成：边搅拌边向三口瓶中加入甲苯(120mL)，无水乙醇(60mL)，水(60mL)，M-10(30.0g，87.0mmol)，M-10A(25.15g，87.0mmol)，K2CO3(18.0g，130.4mmol)，Pd(PPh3)4(1.00g，0.87mmol)，置换氮气三次，开启加热，设置外温100℃，回流反应3hrs后降温，分液，有机相经饱和NaCl水溶液(100mL×3)洗涤后，柱层析纯化，得M-10(43.35g，90％)，MS(70eV,EI+):m/z:553.19；1H NMR(CDCl3,400Hz):δ7.99-8.23(m,5H),7.75-7.83(m,3H),7.38-7.55(m,6H),7.00-7.24(m,13H)。
以下通过器件实施例对本发明化合物的技术效果进行详细的解释说明。
对比例1
对比例1采用化合物
Figure BDA0002594015060000121
作为第一空穴传输层，按照如图1所示的结构制备顶发射结构的OLED显示面板，具体制备工艺为：
在玻璃材质的基底上，形成反射阳极Ag 100nm,在Ag上形成ITO膜层，膜厚15nm，得到第一电极作为阳极，之后蒸镀30nm HATCN(
Figure BDA0002594015060000122
)作为空穴注入层，之后蒸镀100nm厚度的HTL1
Figure BDA0002594015060000123
得到第一空穴传输层，之后蒸镀20nm厚度的
Figure BDA0002594015060000124
得到第二空穴传输层，然后以95％:5％的蒸镀速率蒸镀
Figure BDA0002594015060000125
与
Figure BDA0002594015060000126
30nm，制作蓝光发光单元，然后蒸镀10nm
Figure BDA0002594015060000131
形成空穴阻挡层，然后以50％:50％的蒸镀速率蒸镀30nm的
Figure BDA0002594015060000132
与
Figure BDA0002594015060000133
混合物作为电子传输层，之后以90％:10％的蒸镀速率形成厚度15nm的镁银，作为第二电极，然后形成700nm
Figure BDA0002594015060000134
作为盖帽层。
器件实施例1-5
与对比例1中采用HTL1(
Figure BDA0002594015060000135
)作为第一空穴传输层不同，实施例1至5分别采用上述合成实施例1至5制备的化合物C1、C2、C7、C19和C28作为第一空穴传输层，其他结构均相同。
对比例2
与对比例1中采用HTL1(
Figure BDA0002594015060000136
)作为第一空穴传输层不同，对比例2中采用HTL2(
Figure BDA0002594015060000137
)作为第一空穴传输层不同，其他结构均相同。
表1
Figure BDA0002594015060000141
上述对实施例的描述是为了便于该技术领域的普通技术人员能理解和使用本发明。熟悉本领域技术人员显然可以容易的对这些实施例做出各种修改，并把在此说明的一般原理应用到其他实施例中，而不必经过创造性的劳动。因此，本发明不限于上述实施例。本领域技术人员根据本发明的原理，不脱离本发明的范畴所做出的改进和修改都应该在本发明的保护范围之内。

Claims (6)

1.芳香胺化合物，具有如通式(Ⅰ)所示的化学结构：
Figure FDA0002594015050000011
其中，X选自O、S或-NR-；
R1、R2、R3、R4和R分别独立地选自氢、氘、取代或未取代的环形成碳数为6-30的芳基、取代或未取代的环形成原子数为5-30的杂芳基、取代或未取代的碳数为1-30的烷基、取代或未取代的碳数为1-30的氟烷基、取代或未取代的环形成碳数为3-30的环烷基、取代或未取代的碳数为7-30的芳烷基。
2.根据权利要求1所述的芳香胺化合物，其特征在于，所述芳香胺化合物选自如C1至C36任一所示化学结构：
Figure FDA0002594015050000012
Figure FDA0002594015050000021
Figure FDA0002594015050000031
3.权利要求1或2所述的芳香胺化合物作为有机电致发光器件内空穴传输材料的用途。
4.根据权利要求3所述的用途，其特征在于，所述有机电致发光器件为顶发射结构，依次包括第一电极、空穴注入层、第一空穴传输层、第二空穴传输层、发光层、空穴阻挡层、电子传输层、第二电极和盖帽层；其中，权利要求1或2所述的芳香胺化合物作为第一空穴传输层和/或第二空穴传输层。
5.一种显示面板，其特征在于，包括权利要求3或4所述的有机电致发光器件。
6.一种显示装置，其特征在于，包括权利要求5所述的显示面板。
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113851599A (zh) * 2021-09-13 2021-12-28 烟台显华光电材料研究院有限公司 一种有机电致发光器件及包含该器件的显示装置
CN115611884A (zh) * 2021-07-13 2023-01-17 江苏三月科技股份有限公司 一种含有萘并杂环基和苯并杂环基的单胺类有机化合物及包含其的有机电致发光器件
CN116120265A (zh) * 2021-11-12 2023-05-16 奥来德(上海)光电材料科技有限公司 一种含芳胺基团的发光辅助材料及其制备方法与应用
KR20230173767A (ko) * 2022-06-17 2023-12-27 엘티소재주식회사 헤테로고리 화합물, 이를 포함하는 유기 발광 소자

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017188655A1 (ko) * 2016-04-26 2017-11-02 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
WO2017191976A1 (ko) * 2016-05-04 2017-11-09 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
US20190185411A1 (en) * 2016-05-19 2019-06-20 Duk San Neolux Co., Ltd. Compound for organic electronic device, organic electronic device using same, and electronic apparatus thereof
CN110386894A (zh) * 2018-04-20 2019-10-29 北京鼎材科技有限公司 一种空穴传输材料及其应用

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017188655A1 (ko) * 2016-04-26 2017-11-02 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
WO2017191976A1 (ko) * 2016-05-04 2017-11-09 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
US20190185411A1 (en) * 2016-05-19 2019-06-20 Duk San Neolux Co., Ltd. Compound for organic electronic device, organic electronic device using same, and electronic apparatus thereof
CN110386894A (zh) * 2018-04-20 2019-10-29 北京鼎材科技有限公司 一种空穴传输材料及其应用

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115611884A (zh) * 2021-07-13 2023-01-17 江苏三月科技股份有限公司 一种含有萘并杂环基和苯并杂环基的单胺类有机化合物及包含其的有机电致发光器件
CN115611884B (zh) * 2021-07-13 2023-12-29 江苏三月科技股份有限公司 一种含有萘并杂环基和苯并杂环基的单胺类有机化合物及包含其的有机电致发光器件
CN113851599A (zh) * 2021-09-13 2021-12-28 烟台显华光电材料研究院有限公司 一种有机电致发光器件及包含该器件的显示装置
CN116120265A (zh) * 2021-11-12 2023-05-16 奥来德(上海)光电材料科技有限公司 一种含芳胺基团的发光辅助材料及其制备方法与应用
KR20230173767A (ko) * 2022-06-17 2023-12-27 엘티소재주식회사 헤테로고리 화합물, 이를 포함하는 유기 발광 소자
KR102878286B1 (ko) 2022-06-17 2025-10-30 엘티소재주식회사 헤테로고리 화합물, 이를 포함하는 유기 발광 소자

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