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CN114591301A - 一种有机化合物及其电致发光的应用 - Google Patents

一种有机化合物及其电致发光的应用 Download PDF

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CN114591301A
CN114591301A CN202210331129.5A CN202210331129A CN114591301A CN 114591301 A CN114591301 A CN 114591301A CN 202210331129 A CN202210331129 A CN 202210331129A CN 114591301 A CN114591301 A CN 114591301A
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independently selected
organic compound
substituted
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monocyclic
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邓东阳
刘营
高威
匡立莲
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Wuhan Tianma Microelectronics Co Ltd
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Wuhan Tianma Microelectronics Co Ltd
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Abstract

本发明提供了一种有机化合物，具有式Ⅰ所示结构。本发明提供的一系列化合物可以降低驱动电压，提高器件的发光效率和寿命，在电致发光技术领域中可得到较好的应用。

Description

一种有机化合物及其电致发光的应用
技术领域
本发明涉及有机电致发光材料技术领域，尤其涉及一种有机化合物及其电致发光的应用。
背景技术
有机电致发光材料(OLED)作为新一代显示技术，具有超薄、自发光、视角宽、响应快、发光效率高、温度适应性好、生产工艺简单、驱动电压低、能耗低等优点，已广泛应用于平板显示、柔性显示、固态照明和车载显示等行业。
有机电致发光材料按发光机理可分为电致荧光和电致磷光两种，荧光是单重态激子的辐射衰减跃迁，磷光则是三重态激子辐射衰减到基态所发射的光。根据自旋量子统计理论，单重态激子和三重态激子的形成概率比例是1:3。荧光材料内量子效率不超过25％的限制，外量子效率普遍低于5％；电致磷光材料的内量子效率理论上达到100％，外量子效率可达20％。1998年，我国吉林大学的马於光教授和美国普林斯顿大学的Forrest教授分别报道了采用锇配合物和铂配合物作为染料掺杂入发光层，第一次成功得到并解释了磷光电致发光现象，并开创性的将所制备磷光材料应用于电致发光器件。
由于磷光重金属材料有较长的寿命(μs)，在高电流密度下，可能导致三线态-三线态湮灭和浓度淬灭，造成器件性能衰减，因此通常将重金属磷光材料掺杂到合适的主体材料中，形成一种主客体掺杂体系，使得能量传递最优化，发光效率和寿命最大化。在目前的研究现状中，重金属掺杂材料商业化已成熟，很难开发可替代的掺杂材料。因此，把重心放在研发磷光主体材料是研究者们共通的思路。现在使用的磷光材料存在寿命不够长，效率不够高及驱动电压比较高的问题。
发明内容
有鉴于此，本发明要解决的技术问题在于提供一种有机化合物及其电致发光的应用，制备的有机化合物作为磷光主体材料，可以提升OLED器件效率、寿命，降低驱动电压。
本发明提供了一种有机化合物，具有式Ⅰ所示结构：
Figure BDA0003575231080000021
其中，L1、L2、L3独立的选自单键、取代或非取代的亚芳基或亚杂芳基；
R1、R2、X独立的选自H、取代或非取代的芳基、杂芳基、芳胺基；
所述m、n独立的选自0～4的任意整数。
本发明提供了一种有机发光器件，所述有机发光器件包括阳极、阴极，以及位于所述阳极和阴极之间的有机薄膜层，所述有机薄膜层包括发光层，所述发光层中含有至少一种上述有机化合物。
本发明提供了一种显示面板，包括上述有机发光器件。
与现有技术相比，本发明提供了一种有机化合物，具有式Ⅰ所示结构。本发明提供的一系列化合物可以降低驱动电压，提高器件的发光效率和寿命，在电致发光技术领域中可得到较好的应用。
附图说明
图1为本发明制备的有机发光器件的结构示意图。
具体实施方式
本发明提供了一种有机化合物，具有式Ⅰ所示结构：
Figure BDA0003575231080000031
其中，L1、L2、L3独立的选自单键、取代或非取代的亚芳基或亚杂芳基；
R1、R2、X独立的选自H、取代或非取代的芳基、杂芳基、芳胺基；
所述m、n独立的选自0～4的任意整数。
可选的，所述m、n独立的选自1～4的任意整数。
可选的，当L1、L2、L3同时为单键时，R1、R2、X不同时为H。
可选的，所述m、n独立的选自0、1或2。
可选的，所述m、n独立的选自0或1。
可选的，当m、n同时为0时，L3不为单键，或X不为H。
可选的，所述L1、L2、L3独立的选自单键、取代或非取代的单环亚芳基或单环亚杂芳基；
所述单环亚芳基或单环亚杂芳基的取代基独立的选自氘、C1～C10烷基、芳基或杂芳基。
可选的，所述L1、L2、L3独立的选自单键、取代或非取代的亚苯基或亚吡啶基；
所述亚苯基或亚吡啶基的取代基独立的选自氘、C1～C3烷基、苯基或吡啶基。
可选的，所述R1、R2、X独立的选自H、取代或非取代的单环芳基、单环杂芳基、稠环芳基、稠环杂芳基、稠环芳胺基或N-取代芳胺基；
所述单环芳基、单环杂芳基、稠环芳基、稠环杂芳基、稠环芳胺基、N-取代芳胺基的取代基独立的选自氘、C1～C10烷基、芳基或杂芳基。
可选的，所述R1、R2、X独立的选自H、取代或非取代的苯基、吡啶基、嘧啶基、哒嗪基、吡嗪基、1,2,3-三嗪基，1,3,5-三嗪基、1,3,4-三嗪基、萘基、喹啉基、异喹啉基、喹喔啉基、喹唑啉基、蒽基、菲基、芘基、芴基、咔唑基、二苯并呋喃基、二苯并噻吩基、吖啶基、菲罗啉基、吩噻嗪基、吩噁嗪基、吩嗪基、氧杂蒽基、氮硅杂蒽基、三芳胺基、苯胺基、-N(R3R4)或吲哚并咔唑基；
所述R3、R4独立的选自取代或非取代的芳基或杂芳基。
可选的，所述R3、R4独立的选自取代或非取代的苯基、萘基、吡啶基、联苯基、咔唑基、喹啉基、异喹啉基、喹喔啉基、喹唑啉基、二苯并呋喃基或二苯并噻吩基。
可选的，所述R3、R4独立的选自取代或非取代的苯基、萘基、联苯基或二苯并呋喃基。
可选的，所述R3、R4中的取代基独立的选自氘、C1～C5烷基、单环芳基、稠环芳基或单环杂芳基。
可选的，所述R3、R4中的取代基独立的选自氘、甲基、乙基、正丙基、异丙基、苯基或吡啶基。
可选的，所述氮硅杂蒽基具有以下式a所示结构：
Figure BDA0003575231080000041
可选的，所述吲哚并咔唑基具有式b～式e所示结构：
Figure BDA0003575231080000042
Figure BDA0003575231080000051
上述R1、R2、X与母核的连接位置可以是碳原子或氮原子。
可选的，上述基团的取代基独立的选自氘、C1～C5烷基、单环芳基、稠环芳基或单环杂芳基。
可选的，所述取代基独立的选自氘、甲基、乙基、正丙基、异丙基、苯基、吡啶基、联苯基或萘基。
上述取代基的取代位置可以是R1、R2、X中的任意芳基氢、碳原子连接的氢、硅原子连接的氢或氮原子连接的氢。
可选的，所述有机化合物具有以下任一结构：
Figure BDA0003575231080000061
Figure BDA0003575231080000071
Figure BDA0003575231080000081
Figure BDA0003575231080000091
Figure BDA0003575231080000101
Figure BDA0003575231080000111
Figure BDA0003575231080000121
Figure BDA0003575231080000131
Figure BDA0003575231080000141
Figure BDA0003575231080000151
Figure BDA0003575231080000161
Figure BDA0003575231080000171
Figure BDA0003575231080000181
Figure BDA0003575231080000191
Figure BDA0003575231080000201
Figure BDA0003575231080000211
本发明提供了上述有机化合物的制备方法，包括以下步骤：
Figure BDA0003575231080000221
将化合物A1-a、碘和环氧丙烷加入到装有苯和氮的石英烧瓶中，在UV灯的照射下反应。反应完成后，使用苯/己烷溶液重结晶提纯产物，得到中间体A1-b。将得到的A1-b和NBS溶于THF中进行反应，然后加入100mL水，使反应停止，然后进行萃取，得到中间体A1。
将中间体A1进行取代反应，即可制备得到式Ⅰ所示化合物。
本发明提供的上述有机化合物可以作为性能优良的磷光HOST材料，具有良好的热稳定性和成膜性，适宜的玻璃化温度Tg，利于在热真空蒸镀过程中形成稳定、均一的薄膜，同时减少相分离，保持器件的稳定性。具有较高的载流子传输速率以及平衡的载流子传输性能，以利于器件中空穴和电子传输的平衡同时获得较宽的载流子复合区域，提高发光效率，可用于量产品使用，提升OLED器件效率、寿命，降低驱动电压。
本发明提供了一种有机发光器件，所述有机发光器件包括阳极、阴极，以及位于所述阳极和阴极之间的有机薄膜层，所述有机薄膜层包括发光层，所述发光层中含有至少一种上述有机化合物。
本发明提供了一种显示面板，包括上述有机发光器件。
本发明提供的有机发光器件可以为本领域技术人员熟知的有机发光器件，本发明可选的，所述有机发光器件包括基板、ITO阳极、第一空穴传输层、第二空穴传输层、电子阻挡层、发光层、第一电子传输层、第二电子传输层、阴极(镁银电极，镁银质量比为1:9)和盖帽层(CPL)。
本发明可选的，所述有机发光器件的阳极材料可选自金属-铜、金、银、铁、铬、镍、锰、钯、铂等及它们的合金；如金属氧化物-氧化铟、氧化锌、氧化铟锡(ITO)、氧化铟锌(IZO)等；如导电性聚合物-聚苯胺、聚吡咯、聚(3-甲基噻吩)等，除以上有助于空穴注入材料及其组合，还包括已知的适合做阳极的材料。
本发明可选的，所述有机发光器件的阴极材料可选自金属-铝、镁、银、铟、锡、钛等及它们的合金；如多层金属材料-LiF/Al、LiO2/Al、BaF2/Al等；除以上有助于电子注入的材料及其组合，还包括已知的适合做阴极的材料。
本发明可选的，所述有机光电装置，如有机发光器件中的有机薄膜层至少有一层发光层(EML)，还可以包含其他功能层，包括空穴注入层(HIL)、空穴传输层(HTL)、电子阻挡层(EBL)、空穴阻挡层(HBL)、电子传输层(ETL)、电子注入层(EIL)。
本发明可选的，所述有机发光器件按照以下方法制备：
在透明或不透明的光滑的基板上形成阳极，在阳极上形成有机薄层，在有机薄层上形成阴极。
本发明可选的，形成有机薄层可采用如蒸镀、溅射、旋涂、浸渍、离子镀等已知的成膜方法。
本发明提供了一种显示装置，包括上述显示面板。
在本发明中，有机发光器件(OLED器件)可以用在显示装置中，其中有机发光显示装置可以是手机显示屏、电脑显示屏、电视显示屏、智能手表显示屏、智能汽车显示面板、VR或AR头盔显示屏、各种智能设备的显示屏等。
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，本领域普通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，都属于本发明保护的范围。
核心结构合成：
Figure BDA0003575231080000231
将16mmol化合物A1-2、13mmol碘和40mL环氧丙烷加入到装有550mL苯和氮的石英烧瓶中，在450-W中压汞UV灯的照射下反应12小时左右。反应完成后，使用苯/己烷溶液重结晶提纯产物，得到中间体A1-1。将得到的A1-1和NBS溶于烧瓶中的THF中，持续搅拌1小时左右，加入100mL水，使反应停止，然后进行萃取，得到中间体A1。
可以通过控制NBS与A1-1的摩尔比例，进而控制取代反应是一取代或二取代。
实施例1
Figure BDA0003575231080000241
在氩气气氛下，将10mmol的P1-1和12mmol的反应物b1溶解于60mL甲苯后，加入2M碳酸钠水溶液40mL，加热搅拌。回流状态下，加入0.2mmol催化剂Pd(PPh3)4，加热搅拌8小时。反应结束后，将温度降至室温后，用甲苯萃取有机相，分别用水、饱和食盐水水洗分离有机相和水相，之后用硫酸镁干燥，使用硅胶柱色谱分离并提纯残余物，从而获得化合物P1。
MALDI-TOF(m/z)：C52H31N5:计算值：725.26,实测值：725.38。
元素分析(％)：C52H31N5:计算值：C,86.05；H,4.30；N,9.65。测试值：C,86.07；H,4.29；N,9.64。
实施例2
Figure BDA0003575231080000242
化合物P40的合成方法与P1的合成方法相似，区别在于，将反应中的P1-1和b1分别替换为等摩尔量的P40-1和b40。
MALDI-TOF(m/z)：C59H38N6:计算值：830.32,实测值：830.47。
元素分析(％)：C59H38N6:计算值：C,85.28；H,4.61；N,10.11。测试值：C,85.26；H,4.62；N,10.12。
实施例3
Figure BDA0003575231080000251
化合物P79的合成方法与P1的合成方法相似，区别在于，将反应中的P1-1和b1分别替换为等摩尔量的P79-1和b79。
MALDI-TOF(m/z)：C41H24N4S:计算值：604.17,实测值：604.38。
元素分析(％)：C41H24N4S:计算值：C,81.43；H,4.00；N,9.26；S,5.30。测试值：C,81.43；H,4.01；N,9.25；S,5.31。
实施例4
Figure BDA0003575231080000252
将10mmol反应物P95-1、11mmol反应物b95、15mmol t-BuONa、0.2mmol Pd2(dba)3和0.1mmol P(t-Bu)3溶于60mL甲苯中，并在90℃条件下将混合物搅拌3小时左右。在反应完成后，将反应物冷却到室温，并使用蒸馏水和30mL二乙醚萃取三次。收集有机相，并使用硫酸镁进行干燥，一直到蒸发掉溶剂。使用硅胶柱色谱分离并提纯残余物，从而获得化合物P95
MALDI-TOF(m/z)：C47H28N6O:计算值：692.23,实测值：692.44。
元素分析(％)：C47H28N6O:计算值：C,81.49；H,4.07；N,12.13；O,2.31。测试值：C,81.51；H,4.06；N,12.14；O,2.30。
实施例5
Figure BDA0003575231080000253
化合物P101的合成方法与P1的合成方法相似，区别在于，将反应中的P1-1和b1分别替换为等摩尔量的P101-1和b101。
MALDI-TOF(m/z)：C49H30N4:计算值：674.25,实测值：674.39。
元素分析(％)：C49H30N4:计算值：C,87.22；H,4.48；N,8.30。测试值：C,87.20；H,4.49；N,8.31。
实施例6
Figure BDA0003575231080000261
化合物P111的合成方法与P1的合成方法相似，区别在于，将反应中的P1-1替换为等摩尔量的P111-1。
MALDI-TOF(m/z)：C48H29N3:计算值：647.24,实测值：647.31。
元素分析(％)：C48H29N3:计算值：C,89.00；H,4.51；N,6.49。测试值：C,89.02；H,4.50；N,6.48。
实施例7
Figure BDA0003575231080000262
化合物P113的合成方法与P1的合成方法相似，区别在于，将反应中的P1-1和b1分别替换为等摩尔量的P113-1和b113。
MALDI-TOF(m/z)：C43H26N4:计算值：598.22,实测值：598.30。
元素分析(％)：C43H26N4:计算值：C,86.26；H,4.38；N,9.36。测试值：C,86.24；H,4.39；N,9.37。
实施例8
Figure BDA0003575231080000263
化合物P151的合成方法与P1的合成方法相似，区别在于，将反应中的P1-1和b1分别替换为等摩尔量的P151-1和b151。
MALDI-TOF(m/z)：C47H28N4O:计算值：664.23,实测值：664.35。
元素分析(％)：C47H28N4O:计算值：C,84.92；H,4.25；N,8.43；O,2.41。测试值：C,84.90；H,4.26；N,8.42；O,2.42。
器件实施例1
本应用例提供一种OLED器件，如图1所示，图1为本发明提供的有机发光器件的结构示意图，包括依次层叠的基板1，阳极2、第一空穴传输层3、第二空穴传输层4、发光层5、第一电子传输层6、第二电子传输层7、阴极8与盖帽层9。其中氧化铟锡(ITO)阳极15nm、第一空穴传输层10nm、第二空穴传输层95nm、发光层30nm、第一电子传输层35nm、第二电子传输层5nm、阴极15nm(镁银电极，镁银质量比为1:9)、盖帽层(CPL)100nm。
OLED器件的制备步骤如下：
(1)将玻璃基板1切成50mm×50mm×0.7mm的大小，分别在异丙醇和去离子水中超声处理30min，然后暴露在臭氧下清洁10min；将通过磁控溅射所得的具有ITO阳极2的玻璃基板安装到真空沉积设备上；
(2)在真空度为2×10-6Pa下，在ITO阳极层2上真空蒸镀化合物HAT-CN，厚度为10nm，作为第一空穴传输层3；
(3)在第一空穴传输层3上真空蒸镀化合物TAPC作为第二空穴传输层4，厚度为95nm；
(4)在第二空穴传输层4上真空蒸镀发光层5，采用本发明提供的有机化合物P1作为主体材料，Ir(piq)2(acac)作为掺杂材料，P1和Ir(piq)2(acac)的质量比为97:3，厚度为30nm；
(5)在发光层5上真空蒸镀化合物BCP作为第一电子传输层6，厚度为35nm；
(6)在第一电子传输层6上真空蒸镀化合物Alq3作为第二电子传输层7，厚度为5nm；
(7)在第二电子传输层7上真空蒸镀镁银电极作为阴极8，Mg和Ag质量比为1:9，厚度为15nm；
(8)在阴极8上真空蒸镀高折射率的化合物CBP，厚度为100nm，作为阴极覆盖层(盖帽层)9使用。
所述OLED器件中用到的化合物结构如下：
Figure BDA0003575231080000281
器件实施例2～12
将器件实施例1中步骤(4)中的有机化合物P1分别替换为等量的化合物P40、P79、P95、P101、P111、P113、P151、P161、P163、P165或P167，其他制备步骤同器件实施例1。
器件对比例
一种OLED器件，其与器件实施例1的区别仅在于，将步骤(4)中的有机化合物P1用等量的对比化合物
Figure BDA0003575231080000282
替换；其它原料及制备步骤均相同。
OLED器件的性能评价：
用Keithley 2365A数字纳伏表测试OLED器件在不同电压下的电流，然后用电流除以发光面积得到OLED器件在不同电压下的电流密度；用Konicaminolta CS-2000分光辐射亮度计测试OLED器件在不同电压下的亮度和辐射能流密度；根据OLED器件在不同电压下的电流密度和亮度，得到在相同电流密度下(10mA/cm2)的工作启亮电压和电流效率(Cd/A)，Von为亮度1Cd/m2下的启亮电压；通过测量OLED器件的亮度达到初始亮度的95％时的时间而获得寿命LT95；具体数据如表1所示。
表1OLED器件的性能评价结果
Figure BDA0003575231080000291
从表1可以看出，本发明提供的OLED器件具有较低的工作电压、较高的发光效率以及较长的寿命。相对于器件对比例，采用本发明化合物的OLED器件的工作电压得到降低，发光效率明显提升，寿命明显延长。这可能得益于本发明化合物特殊的结构，可实现HOMO、LUMO能级的较小重叠，实现较小的ΔEST，从而实现比较高效的RISC(反系间窜越)过程，达到较高的发光效率。本发明化合物具有优异的热稳定性和薄膜稳定性，在OLED器件工作时更加稳定，有利于OLED器件的制备和获得更长寿命，是一种性能优异的发光材料。
以上所述，仅为本发明的具体实施方式，但本发明的保护范围并不局限于此，任何熟悉本技术领域的技术人员在本发明揭露的技术范围内，可轻易想到各种等效的修改或替换，这些修改或替换都应涵盖在本发明的保护范围之内。因此，本发明的保护范围应以权利要求的保护范围为准。

Claims (11)

1.一种有机化合物，具有式Ⅰ所示结构：
Figure FDA0003575231070000011
其中，L1、L2、L3独立的选自单键、取代或非取代的亚芳基或亚杂芳基；
R1、R2、X独立的选自H、取代或非取代的芳基、杂芳基、芳胺基；
所述m、n独立的选自0～4的任意整数。
2.根据权利要求1所述的有机化合物，其特征在于，所述m、n独立的选自0、1或2。
3.根据权利要求1所述的有机化合物，其特征在于，所述L1、L2、L3独立的选自单键、取代或非取代的单环亚芳基或单环亚杂芳基；
所述单环亚芳基或单环亚杂芳基的取代基独立的选自氘、C1～C10烷基、芳基或杂芳基。
4.根据权利要求3所述的有机化合物，其特征在于，所述L1、L2、L3独立的选自单键、取代或非取代的亚苯基或亚吡啶基；
所述亚苯基或亚吡啶基的取代基独立的选自氘、C1～C3烷基、苯基或吡啶基。
5.根据权利要求1所述的有机化合物，其特征在于，所述R1、R2、X独立的选自H、取代或非取代的单环芳基、单环杂芳基、稠环芳基、稠环杂芳基、稠环芳胺基或N-取代芳胺基；
所述单环芳基、单环杂芳基、稠环芳基、稠环杂芳基、稠环芳胺基、N-取代芳胺基的取代基独立的选自氘、C1～C10烷基、芳基或杂芳基。
6.根据权利要求5所述的有机化合物，其特征在于，所述R1、R2、X独立的选自H、取代或非取代的苯基、吡啶基、嘧啶基、哒嗪基、吡嗪基、1,2,3-三嗪基，1,3,5-三嗪基、1,3,4-三嗪基、萘基、喹啉基、异喹啉基、喹喔啉基、喹唑啉基、蒽基、菲基、芘基、芴基、咔唑基、二苯并呋喃基、二苯并噻吩基、吖啶基、菲罗啉基、吩噻嗪基、吩噁嗪基、吩嗪基、氧杂蒽基、氮硅杂蒽基、三芳胺基、苯胺基、-N(R3R4)或吲哚并咔唑基；
所述R3、R4独立的选自取代或非取代的芳基或杂芳基；
上述基团的取代基独立的选自氘、C1～C5烷基、单环芳基、稠环芳基或单环杂芳基。
7.根据权利要求6所述的有机化合物，其特征在于，所述R3、R4独立的选自取代或非取代的苯基、萘基、吡啶基、联苯基、咔唑基、喹啉基、异喹啉基、喹喔啉基、喹唑啉基、二苯并呋喃基或二苯并噻吩基。
8.根据权利要求6所述的有机化合物，其特征在于，所述取代基独立的选自氘、甲基、乙基、正丙基、异丙基、苯基、吡啶基、联苯基或萘基。
9.根据权利要求1所述的有机化合物，其特征在于，具有以下任一结构：
Figure FDA0003575231070000021
Figure FDA0003575231070000031
Figure FDA0003575231070000041
Figure FDA0003575231070000051
Figure FDA0003575231070000061
Figure FDA0003575231070000071
Figure FDA0003575231070000081
Figure FDA0003575231070000091
Figure FDA0003575231070000101
Figure FDA0003575231070000111
Figure FDA0003575231070000121
Figure FDA0003575231070000131
Figure FDA0003575231070000141
Figure FDA0003575231070000151
Figure FDA0003575231070000161
Figure FDA0003575231070000171
10.一种有机发光器件，所述有机发光器件包括阳极、阴极，以及位于所述阳极和阴极之间的有机薄膜层，所述有机薄膜层包括发光层，所述发光层中含有至少一种如权利要求1-9任一项所述的有机化合物。
11.一种显示面板，包括权利要求10所述的有机发光器件。
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