CN116063191A - 一种化合物及其在有机光电器件中的应用 - Google Patents

一种化合物及其在有机光电器件中的应用 Download PDF

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CN116063191A
CN116063191A CN202211333257.XA CN202211333257A CN116063191A CN 116063191 A CN116063191 A CN 116063191A CN 202211333257 A CN202211333257 A CN 202211333257A CN 116063191 A CN116063191 A CN 116063191A
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王鹏
王湘成
何睦
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Shanghai Yaoyi Electronic Technology Co ltd
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Shanghai Yaoyi Electronic Technology Co ltd
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Abstract

本发明公开了一种化合物及其在有机光电器件中的应用，该化合物具有如式(1)所示的结构，L1‑L3独立选自单键、取代或未取代的C6‑C30亚芳基、取代或未取代的C3‑C30亚杂芳基；Ar1选自如式(2)所示的基团，Ar2和Ar3独立选自取代或未取代的C6‑C30芳基、取代或未取代的C5‑C30杂芳基，且至少一个选自如式(3)所示的基团。本发明将苯并烷烃衍生物引入到三芳胺类体系中获得一系列性能优良的化合物，作为有机光电器件特别是OLED器件的空穴传输材料可以有效提升器件的发光效率和使用寿命。

Description

一种化合物及其在有机光电器件中的应用
技术领域
本发明涉及有机光电材料领域，特别涉及一种化合物及其在有机光电器件中的应用。
背景技术
有机电致发光器件(OLED)是一类具有类三明治结构的器件，包括正负电极膜层及夹在电极膜层之间的有机功能材料层，已被广泛用于新型照明灯具、智能手机及平板电脑等产品的显示面板，进一步还将向电视等大尺寸显示产品应用领域扩展，是一种发展快、技术要求高的新型显示技术，在信息显示材料、有机光电子材料等领域具有极大的研究价值和应用前景。
随着多媒体信息技术的发展，对平板显示器件性能的要求越来越高。目前主要的显示技术有等离子显示器件、场发射显示器件和OLED显示器件，其中OLED具有自身发光、低电压直流驱动、全固化、视角宽、颜色丰富等一系列优点，与液晶显示器件相比其不需要背光源，视角更宽，功耗低，其响应速度是液晶显示器件的1000倍，具有更广阔的应用前景。自OLED第一次被报道以来，许多学者致力于研究如何提高器件效率和稳定性。目前OLED显示和照明得到广泛的商业化应用，客户终端对OLED屏体光电及寿命要求不断提升，为了应对这类需求，除了在OLED面板制程工艺上精益求精，能够满足更高器件指标的OLED材料开发尤为重要。到目前为止，现有的OLED材料的发展还远远落后于面板制造企业对OLED材料的要求，开发性能更好的有机功能材料满足当前产业发展需求尤为紧迫。
目前，空穴传输材料主要采用具有良好的空穴传输特性的芳香胺化合物，N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺(NPB)由于具有适中的最高已占据轨道能级和良好的空穴迁移率，被广泛用于多种色光的有机电致发光器件，然而该分子的玻璃化转化温度较低(98℃)，器件在长时间工作时累积焦耳热的作用下容易发生相变，对器件寿命造成较大影响，设计同时具有较高迁移率和玻璃化转变温度的空穴传输材料十分必要。
发明内容
基于此，本发明提供一种化合物，其具有如式(1)所示的化学结构：
Figure BDA0003914410150000021
式(1)中，L1-L3彼此相同或不同，各自独立选自单键、取代或未取代的C6-C30亚芳基、取代或未取代的C3-C30亚杂芳基；
Ar1选自如式(2)所示的基团：
Figure BDA0003914410150000022
Z1-Z12彼此相同或不同，各自独立选自C(R5R6)、N(R7)、Si(R8R9)、B(R10)、O或S；R1-R10彼此相同或不同，各自独立选自氢、氘、取代或未取代的直链或支链的C1-C30烷基、取代或未取代的C1-C30杂烷基、取代或未取代的C3-C30环烷基、取代或未取代的C3-C30杂环烷基、取代或未取代的C6-C30芳基、取代或未取代的C5-C30杂芳基或与相邻的原子键合成环；Ar4选自取代或未取代的C6-C30芳基、取代或未取代的C5-C30杂芳基；*为Ar1的连接位点；
Ar2和Ar3相同或不同，各自独立选自取代或未取代的C6-C30芳基、取代或未取代的C5-C30杂芳基，且至少一个选自如式(3)所示的基团：
Figure BDA0003914410150000023
Z13-Z24彼此相同或不同，各自独立选自C(R11R12)、N(R13)、Si(R14R15)、B(R16)、O或S，R11-R16彼此相同或不同，各自独立选自氢、氘、取代或未取代的直链或支链的C1-C30烷基、取代或未取代的C1-C30杂烷基、取代或未取代的C3-C30环烷基、取代或未取代的C3-C30杂环烷基、取代或未取代的C6-C30芳基、取代或未取代的C5-C30杂芳基或与相邻的原子键合成环，*为Ar2或Ar3的连接位点。
本发明将苯并烷烃衍生物引入到三芳胺类体系中获得一系列性能优良的有机化合物，可以作为OLED器件的空穴传输材料，其中：①苯并烷烃衍生物的引入不仅有利于提高分子片段稳定性，同时增加分子量进而提高分子的玻璃化转变温度；②直接将环状烷基引入到分子体系内，使分子的共轭变小，得到高三线态能级的化合物；③烷基的供电子特性使电子的传输能力增强，这类化合物能够为有机电致发光器件提供较强的发光效率和使用寿命。
本发明还提供一种有机光电器件，包括本发明前述的化合物。
本发明还提供一种显示或照明装置，包括本发明前述的有机光电器件。
与现有技术相比，本发明的有益效果为：本发明的化合物因为苯并烷烃及芳基并烷烃基团的引入，使之结构更加稳定的同时，化合物的三线态能级得以提高。另外，脂肪基相对于芳基具有更好的电子传输能力，从而整体化合物具有良好的空穴传输性能以及热稳定性。同时，本发明的化合物应用到有机光电器件上，能使器件具备有较高的空穴迁移率，并且能够有效阻挡电子、激子进入到空穴传输层中，从而提高器件的发光效率，分子高的稳定性也能进一步提升器件的发光效率和使用寿命。
具体实施方式
本发明提供一种苯并烷基芴系列的化合物，应用到有机器件上能使器件具备有较高的空穴迁移率，并且能够有效的阻挡电子、激子进入到空穴传输层中，从而提高器件的效率，同时分子具有高的稳定性也能进一步提升器件的发光效率和使用寿命。在此基础上，完成了本发明。
本发明提供的化合物具有如式(1)所示的化学结构：
Figure BDA0003914410150000031
式(1)中，L1-L3彼此相同或不同，各自独立选自单键、取代或未取代的C6-C30亚芳基、取代或未取代的C3-C30亚杂芳基；
Ar1选自如式(2)所示的基团：
Figure BDA0003914410150000032
Z1-Z12彼此相同或不同，各自独立选自C(R5R6)、N(R7)、Si(R8R9)、B(R10)、O或S；R1-R10彼此相同或不同，各自独立选自氢、氘、取代或未取代的直链或支链的C1-C30烷基、取代或未取代的C1-C30杂烷基、取代或未取代的C3-C30环烷基、取代或未取代的C3-C30杂环烷基、取代或未取代的C6-C30芳基、取代或未取代的C5-C30杂芳基或与相邻的原子键合成环；Ar4选自取代或未取代的C6-C30芳基、取代或未取代的C5-C30杂芳基；*为Ar1的连接位点；
Ar2和Ar3相同或不同，各自独立选自取代或未取代的C6-C30芳基、取代或未取代的C5-C30杂芳基，且至少一个选自如式(3)所示的基团：
Figure BDA0003914410150000041
Z13-Z24彼此相同或不同，各自独立选自C(R11R12)、N(R13)、Si(R14R15)、B(R16)、O或S，R11-R16彼此相同或不同，各自独立选自氢、氘、取代或未取代的直链或支链的C1-C30烷基、取代或未取代的C1-C30杂烷基、取代或未取代的C3-C30环烷基、取代或未取代的C3-C30杂环烷基、取代或未取代的C6-C30芳基、取代或未取代的C5-C30杂芳基或与相邻的原子键合成环，*为Ar2或Ar3的连接位点。
本发明中取代基的实例描述如下，但取代基并不限于此：
【取代或未取代】是指经选自以下的一个或更多个取代基取代：氘、卤素、腈基、硝基、羟基、羰基、酯基、酰亚胺基、氨基、氧化膦基、烷氧基、芳氧基、烷基硫基、芳基硫基、烷基磺酰基、芳基磺酰基、甲硅烷基、硼基、烷基、环烷基、烯基、芳基、芳烷基、芳烯基、烷基芳基、烷基胺基、芳烷基胺基、杂芳基胺基、芳基胺基、芳基膦基和杂芳基、苊基，或未取代；或者经连接以上示例的取代基中的两个或更多个取代基的取代基取代，或未取代；例如，“连接两个或更多个取代基的取代基”可包括联苯基，即联苯基可为芳基，或者为连接两个苯基的取代基。
【烷基】可为直链或支链的，并且碳原子数没有特别限制。一些实施例中，烷基包括但不限于甲基、乙基、丙基、正丙基、异丙基、丁基、正丁基、异丁基、叔丁基、仲丁基、1-甲基-丁基、1-乙基-丁基、戊基、正戊基、异戊基、新戊基、叔戊基、己基、正己基、1-甲基戊基、2-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、庚基、正庚基、1-甲基己基、环戊基甲基、环己基甲基、辛基、正辛基、叔辛基、1-甲基庚基、2-乙基己基、2-丙基戊基、正壬基、2,2-二甲基庚基、1-乙基-丙基、1,1-二甲基-丙基、异己基、4-甲基己基、5-甲基己基。
以上对烷基的描述也可用于芳烷基、芳烷基胺基、烷基芳基和烷基胺基中的烷基。
【杂烷基】可为含杂原子的直链或支链的烷基，并且碳原子数没有特别限制。一些实施例中，杂烷基包括但不限于烷氧基、烷硫基、烷基磺酰基，烷氧基包括但不限于甲氧基、乙氧基、正丙氧基、异丙氧基(isopropoxy)、异丙氧基(i-propyloxy)、正丁氧基、异丁氧基、叔丁氧基、仲丁氧基、正戊氧基、新戊氧基、异戊氧基、正己氧基、3,3-二甲基丁氧基、2-乙基丁氧基、正辛氧基、正壬氧基、正癸氧基、苄氧基、对甲基苄氧基；烷硫基包括但不限于甲硫基、乙硫基、正丙硫基、异丙硫基、异丙硫基、正丁硫基、异丁硫基、叔丁硫基、仲丁硫基、正戊硫基、新戊硫基、异戊硫基、正己硫基、3,3-二甲基丁硫基、2-乙基丁硫基、正辛硫基、正壬硫基、正癸硫基、苄硫基。
【环烷基】可为环状的，并且碳原子数没有特别限制。一些实施例中，环烷基包括但不限于环丙基、环丁基、环戊基、3-甲基环戊基、2,3-二甲基环戊基、环己基、3-甲基环己基、4-甲基环己基、2,3-二甲基环己基、3,4,5-三甲基环己基、4-叔丁基环己基、环庚基、环辛基。
【杂环烷基】可为含杂原子的环烷基，并且碳原子数没有特别限制。一些实施例中，杂环烷基包括但不限于
Figure BDA0003914410150000051
等。
【芳基】没有特别限定，芳基可为单环芳基或多环芳基。一些实施例中，单环芳基包括但不限于苯基、联苯基、三联苯基、四联苯基、五联苯基等。多环芳基包括但不限于萘基、蒽基、菲基、芘基、苝基、芴基等。芴基可为经取代的，例如9,9’-二甲基芴基、9,9’-二苯并芴基等。此外，取代基中的两个可彼此结合形成螺环结构，例如9，9’-螺二芴基等。
以上对芳基的描述可用于亚芳基，不同之处在于亚芳基为二价。
以上对芳基的描述可用于芳氧基、芳基硫基、芳基磺酰基、芳基膦基、芳烷基、芳烷基胺基、芳烯基、烷基芳基、芳基胺基和芳基杂芳基胺基中的芳基。
【杂芳基】包含N、O、P、S、Si和Se中的一个或多个作为杂原子。杂芳基包括但不限于吡啶基、吡咯基、嘧啶基、哒嗪基、呋喃基、噻吩基、咪唑基、吡唑基、唑基、异唑基、噻唑基、异噻唑基、三唑基、二唑基、噻二唑基、二噻唑基、四唑基、吡喃基、噻喃基、吡嗪基、嗪基、噻嗪基、二氧杂环己烯基、三嗪基、四嗪基、喹啉基、异喹啉基、喹啉基、喹唑啉基、喹喔啉基、萘啶基、吖啶基、呫吨基、菲啶基、二氮杂萘基、三氮杂茚基、吲哚基、二氢吲哚基、中氮茚基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、苯并噻唑基、苯并噁唑基、苯并咪唑基、苯并噻吩基、苯并呋喃基、二苯并噻吩基、二苯并呋喃基、咔唑基、苯并咔唑基、二苯并咔唑基、吲哚并咔唑基、茚并咔唑基、吩嗪基、咪唑并吡啶基、吩嗪基、菲啶基、菲咯啉基、吩噻嗪基、咪唑并吡啶基、咪唑并菲啶基、苯并咪唑并喹唑啉基、苯并咪唑并菲啶基、螺[芴-9，9'-氧杂蒽]、苯联萘基、二萘并呋喃基、萘苯并呋喃基、二萘并噻吩基、萘苯并噻吩基、三苯基氧化膦、三苯基硼烷。
以上对杂芳基的描述可用于杂芳基胺基和芳基杂芳基胺基中的杂芳基。
以上对杂芳基的描述可用于亚杂芳基，不同之处在于亚杂芳基为二价的。
具体的，本发明前述的化合物可为未取代或者选自以下的一个或多个取代基取代。例如可以是氘、卤素、腈基、硝基、羟基、羰基、酯基、酰亚胺基、胺基、氧化膦基、烷氧基、芳氧基、烷基硫基、芳基硫基、烷基磺酰基、芳基磺酰基、甲硅烷基、硼基、烷基、环烷基、烯基、芳基、芳烷基、芳烯基、烷基芳基、烷基胺基、芳烷基胺基、杂芳基胺基、芳基胺基、芳基杂芳基胺基、芳基膦基和杂芳基等。
一些实施例中，式(1)中，Ar1选自如式(4)所示任意一个结构的基团：
Figure BDA0003914410150000061
其中，R19-R28彼此相同或不同，各自独立选自氢、氘、取代或未取代的C1-C60烷基、取代或未取代的C1-C60环烷基、取代或未取代的C1-C60杂烷基、取代或未取代的C1-C60杂环烷基、取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基；
Ar4如前所述，*为原子的连接位点。
一些实施例中，式(1)中，Ar2和Ar3选自如式(5)所示任意一个结构的基团：
Figure BDA0003914410150000071
一些实施例中，式(1)中，L1-L3各自独立选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚三联苯基、取代或未取代的亚蒽基、取代或未取代的亚菲基、
Figure BDA0003914410150000081
一些实施例中，式(1)中，Ar1和Ar2各自独立选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的三联苯基、
Figure BDA0003914410150000082
Figure BDA0003914410150000083
具体的，上述结构可为未取代或者选自以下的一个或多个取代基取代，例如可以是氘、卤素基团、腈基、硝基、羟基、羰基、酯基、酰亚胺基、胺基、氧化膦基团、烷氧基、芳氧基、烷基硫基、芳基硫基、烷基磺酰基、芳基磺酰基、甲硅烷基、硼基、烷基、环烷基、烯基、芳基、芳烷基、芳烯、烷基芳基、烷基胺基、芳烷基胺基、杂芳基胺基、芳基胺基、芳基杂芳基胺基、芳基膦基和杂芳基等。
一些实施例中，式(1)所示的化合物选自以下化学结构：
Figure BDA0003914410150000084
Figure BDA0003914410150000091
Figure BDA0003914410150000101
Figure BDA0003914410150000111
Figure BDA0003914410150000121
本发明另一方面提供一种有机层，包括本发明前述的化合物。
本发明另一方面提供如本发明前述的化合物和/或前述的有机层在有机光电器件中的应用。
本发明提供的有机光电器件中，包括第一电极、第二电极、以及设置在第一电极和第二电极之间的一个或多个有机层，为底部或顶部发光器件结构，其有机层可为单层结构，也可为层合有两个或多个有机层的多层串联结构，有机层如具有包括空穴注入层、空穴传输层、发光层、电子注入层或电子传输层中至少一层，可使用制备有机光电器件的常见方法和材料来制备，本发明的有机光电器件采用化合物作为有机光电器件的有机层。
本发明提供的有机光电器件中，第一电极作为阳极层，阳极材料例如可以是具有大功函数的材料，使得空穴顺利地注入有机层，例如金属、金属氧化物、金属和氧化物的组合、导电聚合物等，金属氧化物例如氧化铟锡(ITO)、氧化锌、氧化铟、和氧化铟锌(IZO)等。
本发明提供的有机光电器件中，第二电极作为阴极层，阴极材料例如可以是具有小功函数的材料，使得电子顺利地注入有机层，阴极材料例如金属或多层结构材料，金属例如是镁、银、钙、钠、钾、钛、铟、钇、锂、钆、铝、锡和铅或其合金，阴极材料优选镁和银。
本发明提供的有机光电器件中，空穴注入层的材料，优选最高占据分子轨道(HOMO)介于阳极材料的功函数与周围有机层的HOMO之间的材料作为在低电压下有利地从阳极接收空穴的材料。
本发明提供的有机光电器件中，空穴传输层的材料是对空穴具有高迁移率的材料适合作为接收来自阳极或空穴注入层的空穴并将空穴传输至发光层的材料。空穴传输层的材料包括但不限于芳基胺的有机材料、导电聚合物、同时具有共轭部分和非共轭部分的嵌段共聚物等。
本发明提供的有机光电器件中，本发明提供的化合物可以应用于器件的发光层。
本发明提供的有机光电器件中，电子传输层的材料是对电子具有高迁移率的材料适合作为有利地接收来自阴极的电子并将电子传输至发光层的材料。
本发明提供的有机光电器件中，覆盖层的材料通常具有高折射率，因此可有助于有机发光器件的光效率提高，尤其是有助于外部发光效率提高。
本发明提供的有机光电器件中，有机光电器件为有机光伏器件、有机发光器件、有机太阳电池、电子纸、有机感光体、有机薄膜晶体管等。
本发明另一方面提供一种显示或照明装置，包括本发明所述的有机光电器件。
合成实施例：
上述式(Ⅰ)所示的化合物的合成可以使用已知的方法进行，例如使用镍、钯等过渡金属的交叉偶合反应。其他合成方法是使用镁或锌等过渡金属的C-C，C-N偶联生成反应。上述反应，限于反应条件温和、各种官能团的选择性优越等特点，优选Suzuki、Buchwald反应。本发明的化合物用以下实施例举例说明，但并不限于这些实施例举例的化合物和合成方法。本发明的初始原料和溶剂和一些常用的OLED中间体类等产品购于国内的OLED中间体厂商；各种钯催化剂，配体等购于sigma-Aldrich公司，1H NMR数据使用JEOL(400MHz)核磁共振仪来测定，HPLC数据使用岛津LC-20AD高效液相仪来测定。
实施例中使用物质为：
Figure BDA0003914410150000131
实施例1
化合物2的合成
Figure BDA0003914410150000132
中间体2-1的合成：
在氩气氛围下，向反应容器中加入化合物2-A 27.5克(100mmol)，化合物2-B 18.3克(100mmol)，叔丁醇钠23.4克(240mmol)，双二亚苄基丙酮钯575毫克(1mmol％)，四氟硼酸三叔丁基膦348毫克(1.2mmol％)和1000mL二甲苯(xylene)，在140℃加热搅拌15小时。反应混合物冷却到室温，加入1000ml水，过滤，滤饼用大量水洗涤，真空干燥，粗品通过硅胶柱层析法精制(洗脱液：乙酸乙酯/正己烷)，得到30.6克化合物2-1，HPLC纯度99.6％，收率81％。LC MS：M/Z 377.18(M+)。1H NMR(400MHz,DMSO-d6)δ1.72(s,6H),7.02(s,1H),7.12–7.41(m,11H),7.45(m,1H),7.51–7.57(m,1H),7.65–7.71(m,1H),7.95–8.01(m,1H),8.03(m,1H).
化合物2的合成：
在氩气氛围下，向反应容器中加入化合物2-1 37.7克(100mmol)，化合物2-C 26.7克(100mmol)，叔丁醇钠23.4克(240mmol)，双二亚苄基丙酮钯575毫克(1mmol％)，四氟硼酸三叔丁基膦348毫克(1.2mmol％)和1000mL二甲苯(xylene)，在140℃加热搅拌15小时。反应混合物冷却到室温，加入1000ml水，过滤，滤饼用大量水洗涤，真空干燥，粗品通过硅胶柱层析法精制(洗脱液：乙酸乙酯/正己烷)，得到39.5克化合物2，HPLC纯度99.9％，收率70％。LCMS：M/Z 563.32(M+)。1H NMR(400MHz,DMSO-d6)δ0.91(s,12H),1.48(s,4H),1.72(s,6H),6.45(m,1H),6.91(m,1H),7.00(d,1H),7.08(d,1H),7.10–7.36(m,10H),7.45(m,1H),7.50–7.58(m,1H),7.68(m,1H),7.94–8.06(m,2H).
实施例2
化合物9的合成
Figure BDA0003914410150000141
除了起始原料更换为9-A以外，其他与实施例1相同。LC MS:M/Z 687.35(M+)。HPLC纯度：99.9％，总收率：51％；1H NMR(400MHz,DMSO-d6)δ0.91(s,12H),1.48(s,4H),6.45(m,1H),6.91(m,1H),6.92–7.04(m,3H),7.08(d,1H),7.06–7.14(m,6H),7.10–7.22(m,5H),7.22–7.31(m,6H),7.26–7.36(m,1H),7.45(m,1H),7.50–7.58(m,1H),7.68(m,1H),7.94–8.06(m,2H).
实施例3
化合物15的合成
Figure BDA0003914410150000142
除了起始原料更换为15-A、15-B和15-C以外，其他与实施例1相同。LC MS:M/Z603.29(M+)。合成总收率：50％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ2.07(m,2H),2.85–2.99(m,4H),6.92–7.02(m,4H),7.06–7.22(m,12H),7.22–7.30(m,6H),7.30–7.38(m,2H),7.34–7.43(m,1H),7.43–7.53(m,2H),7.50–7.58(m,2H),7.69–7.77(m,2H).
实施例4
化合物29的合成
Figure BDA0003914410150000151
除了起始原料更换为29-A和15-B以外，其他与实施例1相同。LC MS:M/Z 671.36(M+)。合成总收率：49％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ0.91(s,12H),1.48(s,4H),6.45(m,1H),6.92–7.03(m,3H),7.03–7.10(m,3H),7.10–7.22(m,3H),7.22–7.43(m,9H),7.43–7.58(m,6H),7.69–7.77(m,2H),7.86–7.94(m,2H).
实施例5
化合物40的合成
Figure BDA0003914410150000152
除了起始原料更换为29-A、40-B和40-C以外，其他与实施例1相同。LC MS:M/Z718.33(M+)。合成总收率：48％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ1.68–1.91(m,6H),2.71(m,2H),2.83(m,2H),6.92–7.00(m,2H),7.01(m,1H),7.02–7.10(m,3H),7.10–7.42(m,16H),7.48(m,2H),7.63(m,2H),7.79–7.87(m,2H),7.90(m,2H),8.16–8.24(m,2H).
实施例6
化合物54的合成
Figure BDA0003914410150000161
除了起始原料更换为54-A、40-B和54-C以外，其他与实施例1相同。LC MS:M/Z696.28(M+)。合成总收率：49％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ5.97(s,2H),6.75(d,1H),6.83(m,2H),6.92–7.00(m,2H),7.06–7.22(m,11H),7.22–7.32(m,8H),7.32–7.40(m,4H),7.63(m,2H),7.79–7.87(m,2H),8.16–8.24(m,2H).
实施例7
化合物70的合成
Figure BDA0003914410150000162
除了起始原料更换为29-A、15-B和70-C以外，其他与实施例1相同。LC MS:M/Z619.23(M+)。合成总收率：51％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ2.83(m,2H),3.12(t,2H),6.91(m,1H),6.93–7.00(m,2H),7.03–7.11(m,3H),7.11–7.18(m,2H),7.13–7.22(m,1H),7.22–7.43(m,9H),7.43–7.49(m,1H),7.45–7.55(m,3H),7.51–7.58(m,2H),7.60(d,1H),7.69–7.77(m,2H),7.90(m,2H).
实施例8
化合物79的合成
Figure BDA0003914410150000163
除了起始原料更换为29-A、79-B和79-C以外，其他与实施例1相同。LC MS:M/Z689.28(M+)。合成总收率：50％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ1.48(s,12H),6.92–7.00(m,2H),7.03(m,1H),7.03–7.11(m,2H),7.13(s,1H),7.12–7.22(m,3H),7.22–7.42(m,8H),7.48(m,3H),7.56(m,1H),7.64(m,1H),7.87–7.94(m,3H),7.99(m,1H),8.45(m,1H).
实施例9
化合物93的合成
Figure BDA0003914410150000171
除了起始原料更换为93-A、93-B和93-C以外，其他与实施例1相同。LC MS:M/Z830.37(M+)。合成总收率：49％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ1.22(s,12H),1.80(s,2H),6.00(d,1H),6.93(d,1H),6.98(d,2H),7.06–7.13(m,6H),7.13–7.22(m,5H),7.22–7.31(m,8H),7.31–7.43(m,3H),7.48(m,2H),7.52–7.61(m,1H),7.56–7.67(m,3H),7.68–7.76(m,2H),8.16–8.27(m,2H).
实施例10
化合物98的合成
Figure BDA0003914410150000172
除了起始原料更换为98-A、15-B和98-C以外，其他与实施例1相同。LC MS:M/Z783.35(M+)。合成总收率：50％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ1.67–1.82(m,4H),2.63–2.78(m,4H),6.45(m,1H),6.83(m,1H),6.97(m,1H),7.09(m,7H),7.13–7.22(m,3H),7.22–7.30(m,6H),7.30–7.43(m,5H),7.43–7.53(m,2H),7.50–7.59(m,4H),7.59–7.66(m,2H),7.69–7.80(m,3H),7.83(d,1H),8.19–8.25(m,1H).
实施例11
化合物102的合成
Figure BDA0003914410150000173
除了起始原料更换为102-A、102-B和102-C以外，其他与实施例1相同。LC MS:M/Z709.35(M+)。合成总收率：59％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ0.91(s,12H),1.48(s,4H),1.76–2.06(m,4H),2.65–2.84(m,2H),3.93–4.03(m,1H),6.45(m,1H),6.91(m,1H),7.00(d,1H),7.05–7.18(m,3H),7.19–7.29(m,1H),7.31(m,1H),7.45(m,1H),7.50–7.59(m,2H),7.68(m,1H),7.94–8.06(m,2H).
实施例12
化合物110的合成
Figure BDA0003914410150000181
除了起始原料更换为110-A和110-B以外，其他与实施例1相同。LC MS:M/Z 551.26(M+)。合成总收率：51％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ0.91(s,12H),1.48(s,4H),2.06(m,1H),2.31(m,1H),3.14(t,2H),3.81(m,1H),6.45(m,1H),6.96–7.05(m,2H),7.08(d,1H),7.32(m,1H),7.42–7.52(m,3H),7.52–7.63(m,3H),7.66–7.78(m,2H),7.81(m,1H),7.87–7.95(m,1H),8.45(m,1H).
实施例13
化合物116的合成
Figure BDA0003914410150000182
除了起始原料更换为116-A、116-B和116-C以外，其他与实施例1相同。LC MS:M/Z541.24(M+)。合成总收率：50％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ2.07(m,2H),2.77–2.99(m,4H),3.01–3.17(m,2H),3.24–3.41(m,3H),6.91(m,1H),6.98(d,2H),7.11–7.22(m,3H),7.22–7.36(m,4H),7.40–7.53(m,3H),7.49–7.59(m,2H),7.68(m,1H),7.74–7.84(m,1H),7.94–8.06(m,3H).
实施例14
化合物124的合成
Figure BDA0003914410150000183
除了起始原料更换为124-A和124-B以外，其他与实施例1相同。LC MS:M/Z 513.27(M+)。合成总收率：50％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ0.91(s,12H),1.48(s,4H),4.42(m,1H),4.67(m,1H),5.33(t,1H),6.45(m,1H),6.86–6.98(m,3H),6.93–7.03(m,2H),7.03–7.11(m,2H),7.56–7.73(m,4H),7.98–8.11(m,2H),8.73–8.81(m,1H),8.94–9.02(m,1H).
实施例15
化合物139的合成
Figure BDA0003914410150000191
除了起始原料更换为139-A、139-B和139-C以外，其他与实施例1相同。LC MS:M/Z690.31(M+)。合成总收率：51％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ0.91(s,12H),1.80(s,2H),3.04(m,1H),3.29(m,1H),4.44(m,1H),5.97(d,1H),6.41(m,1H),6.98(d,2H),7.14–7.44(m,10H),7.48(m,2H),7.52–7.61(m,1H),7.56–7.67(m,3H),7.73–7.82(m,2H),8.16–8.27(m,2H).
实施例16
化合物145的合成
Figure BDA0003914410150000192
除了起始原料更换为145-A、110-B和145-C以外，其他与实施例1相同。LC MS:M/Z623.23(M+)。合成总收率：50％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ1.96–2.10(m,2H),2.10–2.24(m,1H),2.35–2.49(m,1H),2.66–2.76(m,2H),3.14(t,2H),4.06–4.16(m,1H),4.22–4.30(m,2H),6.79–6.87(m,2H),7.03(m,1H),7.14–7.22(m,1H),7.28–7.40(m,3H),7.42–7.61(m,7H),7.64(m,1H),7.74–7.84(m,3H),7.87–7.95(m,1H),8.00(m,2H),8.45(m,1H).
实施例17
化合物161的合成
Figure BDA0003914410150000193
除了起始原料更换为161-A、40-B和40-C以外，其他与实施例1相同。LC MS:M/Z658.33(M+)。合成总收率：51％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ1.68–1.91(m,8H),2.01(m,1H),2.71(m,2H),2.83(m,2H),2.96(m,1H),3.03(t,2H),3.21(m,1H),3.28–3.42(m,1H),6.87(m,1H),6.94–7.05(m,2H),7.05(m,1H),7.19–7.26(m,2H),7.26–7.32(m,2H),7.32–7.41(m,4H),7.46–7.60(m,4H),7.63(m,2H),7.71(d,2H),7.79–7.87(m,2H),8.15–8.25(m,2H).
实施例18
化合物174的合成
Figure BDA0003914410150000201
除了起始原料更换为174-A、174-B和174-C以外，其他与实施例1相同。LC MS:M/Z755.40(M+)。合成总收率：50％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ1.69(s,6H),2.02(m,1H),2.27(m,1H),2.89(s,9H),3.05(m,2H),3.59(s,4H),4.11(m,1H),6.31(m,1H),6.40(m,1H),6.45–6.53(m,2H),6.66(m,1H),6.78(m,1H),7.05–7.16(m,2H),7.27(m,1H),7.30–7.39(m,3H),7.42–7.67(m,9H),7.79–7.86(m,1H),7.83–7.92(m,2H),8.11–8.17(m,1H).
实施例19
化合物186的合成
Figure BDA0003914410150000202
除了起始原料更换为186-A和110-B以外，其他与实施例1相同。LC MS:M/Z 749.41(M+)。合成总收率：51％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ0.91(s,12H),1.48(s,4H),1.69(s,12H),1.77–2.10(m,3H),2.15–2.30(m,1H),2.68–2.81(m,2H),4.05(m,1H),6.45(m,1H),6.84(m,1H),6.85–6.93(m,1H),6.93–7.24(m,11H),7.48(m,1H),7.52–7.63(m,3H),7.87–7.95(m,1H),8.45(m,1H).
实施例20
化合物198的合成
Figure BDA0003914410150000211
除了起始原料更换为198-A、15-B和98-C以外，其他与实施例1相同。LC MS:M/Z657.34(M+)。合成总收率：50％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ1.69(s,6H),1.69–1.82(m,4H),2.63–2.78(m,3H),3.11(m,2H),3.30–3.42(m,2H),3.46–3.63(m,1H),6.45(m,1H),6.83(m,1H),6.95–7.01(m,1H),7.08(m,1H),7.28–7.43(m,8H),7.43–7.58(m,7H),7.63–7.70(m,1H),7.70–7.77(m,2H),7.80(m,2H),7.85(d,1H).
实施例21
化合物205的合成
Figure BDA0003914410150000212
除了起始原料更换为205-A、15-B和205-C以外，其他与实施例1相同。LC MS:M/Z607.29(M+)。合成总收率：50％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ2.00–2.19(m,4H),2.16–2.28(m,1H),2.39–2.53(m,1H),2.66(m,4H),2.76–2.87(m,5H),2.92(m,1H),4.19(m,1H),6.74(m,1H),6.97(m,1H),7.10–7.31(m,5H),7.31–7.38(m,2H),7.34–7.48(m,2H),7.43–7.53(m,2H),7.50–7.60(m,4H),7.69–7.77(m,2H),8.19–8.25(m,1H).
器件实施例1：有机电致发光器件的制备
Figure BDA0003914410150000213
制备工艺为：在玻璃材质的基底上，形成透明阳极ITO膜层(厚度150nm)，得到第一电极作为阳极。随后通过真空蒸镀的方法，在阳极表面蒸镀化合物T-1与化合物T-2的混合材料作为空穴注入层，混合比例为3:97(质量比)，厚度为10nm。随后在空穴注入层上蒸镀100nm厚度的化合物T-2，得到第一层空穴传输层。随后在第一空穴传输层上蒸镀10nm厚度的本发明化合物2，得到第二层空穴传输层。在第二空穴传输层上，将化合物T-3和化合物T-4以95:5的质量比进行共蒸镀，形成厚度为40nm的有机发光层。然后，在有机发光层上，依次蒸镀化合物T-5形成空穴阻挡层(厚度10nm)，以及混合比例为4:6(质量比)的化合物T-6和LiQ形成电子传输层(厚度30nm)。最后将镁(Mg)和银(Ag)以1∶9的蒸镀速率混合，真空蒸镀在电子注入层层上，作为第二电极109，完成有机发光器件的制造。
器件实施例2-21
除了在形成第二空穴传输层时，分别以化合物9、15、29、40、54、70、79、93、98、102、110、116、124、139、145、161、174、186、198和205替代化合物2外，采用与器件实施例1相同的方法制作有机电致发光器件。
器件对比例1-2
除了在形成第二空穴传输层时，分别以化合物HT-1、化合物HT-2替代化合物2外，采用与器件实施例1相同的方法制作有机电致发光器件。
对以上制得的有机电致发光器件，通过计算机控制的Keithley 2400测试系统计算得到工作电压和效率。使用配备电源和光电二极管作为检测单元的Polaronix(McScience Co.)寿命测量系统得到黑暗条件下的器件寿命。每一组器件实施例和器件对比例1均与器件对比例2的器件在同一批次中产出并测试，将器件对比例1的器件的工作电压、效率和寿命均分别记为1，并分别计算器件实施例1-21、器件对比例的与器件对比例1相应指标的比值，如表1所示。
表1
Figure BDA0003914410150000221
Figure BDA0003914410150000231
根据表1的结果可知，作发光器件的第二空穴传输层时，器件实施例1-21所使用的化合物与器件对比例1-2中使用的化合物形成的器件相比，电压均有所降低，发光效率均有所提高，寿命提高显著。
据此，本发明的化合物应用到有机器件上，能使器件具备有较高的空穴迁移率，并且能够有效的阻挡电子、激子进入到空穴传输层中，从而提高器件的效率，同时分子具有高的稳定性，能进一步提升器件的发光效率和使用寿命，在有机光电器件产品领域具有较大的应用价值。
以上所述，仅为本发明较佳的具体实施方式，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，根据本发明的技术方案及其发明构思加以等同替换或改变，都应涵盖在本发明的保护范围之内。

Claims (11)

1.一种化合物，其具有如式(1)所示的化学结构：
Figure FDA0003914410140000011
式(1)中，L1-L3彼此相同或不同，各自独立选自单键、取代或未取代的C6-C30亚芳基、取代或未取代的C3-C30亚杂芳基；
Ar1选自如式(2)所示的基团：
Figure FDA0003914410140000012
Z1-Z12彼此相同或不同，各自独立选自C(R5R6)、N(R7)、Si(R8R9)、B(R10)、O或S；
R1-R10彼此相同或不同，各自独立选自氢、氘、取代或未取代的直链或支链的C1-C30烷基、取代或未取代的C1-C30杂烷基、取代或未取代的C3-C30环烷基、取代或未取代的C3-C30杂环烷基、取代或未取代的C6-C30芳基、取代或未取代的C5-C30杂芳基或与相邻的原子键合成环；
Ar4选自取代或未取代的C6-C30芳基、取代或未取代的C5-C30杂芳基；
*为Ar1的连接位点；
Ar2和Ar3相同或不同，各自独立选自取代或未取代的C6-C30芳基、取代或未取代的C5-C30杂芳基，且至少一个选自如式(3)所示的基团：
Figure FDA0003914410140000013
Z13-Z24彼此相同或不同，各自独立选自C(R11R12)、N(R13)、Si(R14R15)、B(R16)、O或S；
R11-R16彼此相同或不同，各自独立选自氢、氘、取代或未取代的直链或支链的C1-C30烷基、取代或未取代的C1-C30杂烷基、取代或未取代的C3-C30环烷基、取代或未取代的C3-C30杂环烷基、取代或未取代的C6-C30芳基、取代或未取代的C5-C30杂芳基或与相邻的原子键合成环；
*为Ar2或Ar3的连接位点。
2.根据权利要求1所述的化合物，其特征在于，式(1)中，Ar1选自如式(4)所示任意一个结构的基团：
Figure FDA0003914410140000021
其中，R19-R28彼此相同或不同，各自独立选自氢、氘、取代或未取代的C1-C60烷基、取代或未取代的C1-C60环烷基、取代或未取代的C1-C60杂烷基、取代或未取代的C1-C60杂环烷基、取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基；
Ar4如权利要求1所述，*为原子的连接位点。
3.根据权利要求1所述的化合物，其特征在于，式(1)中，Ar2和Ar3选自如式(5)所示任意一个结构的基团：
Figure FDA0003914410140000022
Figure FDA0003914410140000031
4.根据权利要求1所述的化合物，其特征在于，式(1)中，L1-L3各自独立选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚三联苯基、取代或未取代的亚蒽基、取代或未取代的亚菲基、
Figure FDA0003914410140000032
Figure FDA0003914410140000041
5.根据权利要求1所述的化合物，其特征在于，式(1)中，Ar1和Ar2各自独立选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的三联苯基、
Figure FDA0003914410140000042
Figure FDA0003914410140000043
6.根据权利要求1所述的化合物，其特征在于，式(1)所示的化合物选自以下化学结构：
Figure FDA0003914410140000044
Figure FDA0003914410140000051
Figure FDA0003914410140000061
Figure FDA0003914410140000071
7.权利要求1至6任一项所述化合物在有机光电器件中的应用。
8.一种有机光电器件，包括权利要求1至6任一项所述化合物中的一种或多种。
9.根据权利要求8所述的有机光电器件，其特征在于，包括基板、第一电极、有机层和第二电极，其中所述有机层为空穴注入层、空穴传输层、发光层、电子注入层或电子传输层中的至少一层，其材料包括权利要求1至6任一项所述化合物中的一种或多种。
10.根据权利要求8所述的有机光电器件，其特征在于，所述有机光电器件为有机光伏器件、有机发光器件、有机太阳电池、电子纸、有机感光体、有机薄膜晶体管中的至少一种。
11.一种显示或照明装置，其特征在于，包括权利要求8至10所述有机光电器件。
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