CN115304498A - 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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CN115304498A
CN115304498A CN202211070569.6A CN202211070569A CN115304498A CN 115304498 A CN115304498 A CN 115304498A CN 202211070569 A CN202211070569 A CN 202211070569A CN 115304498 A CN115304498 A CN 115304498A
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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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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，该化合物的化学结构如式(Ⅰ)所示，其中A选自
Figure DDA0003829961780000011
或
Figure DDA0003829961780000012
X1、Z1和Z2分别选自‑CR17R18‑、‑NR19‑、S或O，X1还选自单键，R1～R22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。本发明的化合物通过引入苊基和七元螺环结构，具有较大的三线态能级和良好的热稳定性，用于有机电致发光器件可以降低驱动电压，提高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
本发明属于有机光电材料领域，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(OLED:Organic Light Emission Diodes)器件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，该技术已被广泛应用于新型照明灯具、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。有机电致发光(OLED)材料在信息显示材料、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、场发射显示器件和有机电致发光显示器件(OLED)。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，OLED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，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的不断提升，为应对这类需求，除了在OLED面板制程工艺上的精益求精，能够满足更高器件指标的OLED材料的开发尤为重要。
目前，OLED光电功能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显得尤为紧迫。例如，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，从而被广泛应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，从而对器件的寿命造成较大的影响，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有必要。另外，主体材料作为器件的关键发光物质，对其性能要求更为苛刻，例如热稳定性、电学稳定性、高的发光效率和使用寿命。因此，开发稳定高效的主体材料降低驱动电压，提高器件发光效率，延长器件寿命，具有重要的实际应用价值。
发明内容
本发明提供一种可用于有机光电器件的化合物，其化学结构如式(Ⅰ)所示：
Figure BDA0003829961770000021
式(Ⅰ)中，A选自
Figure BDA0003829961770000022
Z1和Z2分别选自-CR17R18-、-NR19-、S或O；
X1选自单键、-CR20R21-、-NR22-、S或O；
R1～R22相同或不相同，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。
与现有技术相比，本发明的有益效果为：本发明的化合物采用螺环结构，分子结构共轭较小，从而具有较大的三线态能级。另外，通过引入苊基和七元螺环基团使化合物的刚性增强，从而化合物具有良好的热稳定性。并且，分子间的堆积更加松散，蒸镀温度能降低，作为空穴传输材料、电子传输材料或发光材料用于红色和绿色磷光有机电致发光器件，具有较高的三线态能级、较好的载流子迁移率且能与相邻能级匹配、较高的热稳定性和成膜稳定性，能够降低驱动电压，提高器件的发光效率和使用寿命。
具体实施方式
以下详细说明具体公开的化合物及其在有机光电器件中的应用的实施方式。本领域技术人员可由本说明书所揭露的内容轻易地了解本发明的其他优点与功效。本发明还可以通过另外不同的具体实施方式加以实施或应用，本说明书中的各项细节也可以基于不同观点与应用，在没有背离本发明的精神下进行各种修饰或改变。
在进一步描述本发明具体实施方式之前，应理解，本发明的保护范围不局限于下述特定的具体实施方案；还应当理解，本发明实施例中使用的术语是为了描述特定的具体实施方案，而不是为了限制本发明的保护范围；在本发明说明书和权利要求书中，除非文中另外明确指出，单数形式“一个”、“一”和“这个”包括复数形式。
当实施例给出数值范围时，应理解，除非本发明另有说明，每个数值范围的两个端点以及两个端点之间任何一个数值均可选用。除非另外定义，本发明中使用的所有技术和科学术语与本技术领域技术人员通常理解的意义相同。除实施例中使用的具体方法、设备、材料外，根据本技术领域的技术人员对现有技术的掌握及本发明的记载，还可以使用与本发明实施例中方法、设备、材料相似或等同的现有技术中任何方法、设备和材料来实现本发明。
本发明经过大量探索研究提供一种基于芴衍生基团的螺环化合物，应用于有机光电器件具有较高的器件效率，同时分子具有高稳定性，提升器件的发光效率和使用寿命，在此基础上完成本发明。
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、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】可为直链或支链的烷基，并且碳原子数没有特别限制。在一些实施例中，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。在一些实施例中，杂烷基包括但不限于烷氧基、烷硫基、烷基磺酰基等；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、对甲基苄氧基等；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、苄硫基等。
【环烷基】可为环状的环烷基，且碳原子数没有特别限制。在一些实施例中，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、环辛基等。
【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。在一些实施例中，杂环烷基包括但不限于
Figure BDA0003829961770000041
等。
【芳基】没有特别限定，可为单环芳基或多环芳基。在一些实施例中，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、三苯基硼烷等。
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。
本发明提供一种化合物，其化学结构如式(Ⅰ)所示：
Figure BDA0003829961770000051
式(Ⅰ)中，A选自
Figure BDA0003829961770000052
Z1和Z2分别选自-CR17R18-、-NR19-、S或O；
X1选自单键、-CR20R21-、-NR22-、S或O；
R1～R22相同或不相同，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。
具体地，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、腈基、硝基、羟基、羰基、酯基、酰亚胺基、胺基、氧化膦、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。
上述化合物以芴的衍生物为母体，该母体结构具有良好的热稳定性，同时具有合适的HOMO、LUMO能级和Eg，具有较高的三线态能级、较好的载流子迁移率且能与相邻能级匹配，具有较高的热稳定性和成膜稳定性，是一种新型OLED材料，可以作为空穴传输材料或电子传输材料及主体材料应用于OLED器件，有效地提升器件的效率和寿命。
一些实施例中，式(Ⅰ)中，R1～R8至少一个选自如下任一个结构：
Figure BDA0003829961770000053
其中，B和C独立选自取代或未取代的C6～C60芳基、取代或未取代的C5～C60杂芳基、或选自如下任一个结构：
Figure BDA0003829961770000061
E选自含氟原子的吸电子基团、含氮原子的吸电子基团或含氧的吸电子基团；
Ar1～Ar8相同或不同，独立选自取代或未取代的C6～C60芳基、取代或未取代的C5～C60杂芳基；
X1～X13相同或不同，独立选自O、S、-CR25R26-、-NR27-或-SiR28R29-；
L1～L9相同或不同，独立选自不存在、单键、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～C60芳基、取代或未取代的C5～C60杂芳基；
R23～R29相同或不同，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～C60芳基、取代或未取代的C5～C60杂芳基；
*为连接位点。
一些实施例中，式(Ⅰ)所示的化合物选自以下化学结构中的一种或多种：
Figure BDA0003829961770000062
Figure BDA0003829961770000071
Figure BDA0003829961770000081
Figure BDA0003829961770000091
Figure BDA0003829961770000101
Figure BDA0003829961770000111
Figure BDA0003829961770000121
Figure BDA0003829961770000131
Figure BDA0003829961770000141
Figure BDA0003829961770000151
Figure BDA0003829961770000161
Figure BDA0003829961770000171
本发明还提供一种有机层，包括本发明前述的化合物。
本发明还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。
本发明所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，所述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，采用本发明前述的化合物作为有机光电器件的有机层。
本发明所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；例如还可以是金属、金属氧化物、金属和氧化物的组合、导电聚合物等，金属氧化物例如可以是氧化铟锡(ITO)、氧化锌、氧化铟、和氧化铟锌(IZO)等。
本发明所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，阴极材料例如可以是金属或多层结构材料，金属例如可以是镁、银、钙、钠、钾、钛、铟、钇、锂、钆、铝、锡、铅或其合金，阴极材料优选镁和银。
本发明所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。
本发明所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，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，本发明如式(Ⅰ)所示的化合物可以应用于器件的空穴传输层。
本发明所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，本发明如式(Ⅰ)所示的化合物可以应用于器件的电子传输层。
本发明所提供的有机光电器件中，如式(Ⅰ)所示的化合物可以应用于器件的发光层。
本发明所提供的有机光电器件中，覆盖层的材料通常具有高折射率，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。
本发明所提供的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。
本发明一方面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。
以下通过具体实例进一步解释说明本发明的技术方案。
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 BDA0003829961770000191
Figure BDA0003829961770000201
实施例1
化合物D-3的合成
Figure BDA0003829961770000202
1)中间体D-3-1的合成
在氩气氛围下，向反应容器中加入化合物D-3-A 42.3g(100mmol)、化合物D-3-B20.9g(100mmol)、叔丁醇钠23.1g(240mmol)、双二亚苄基丙酮钯575毫g(1mmol％)、2-双环己基膦-2',4',6'-三异丙基联苯953毫g(2mmol％)和1000mL二甲苯(xylene)，在140℃加热搅拌20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/己烷)，得到41.4g化合物D-3-1，HPLC纯度99.5％，收率75％.LC MS：M/Z 551.26(M+)。1H NMR(400MHz,DMSO-d6)δ1.69(s,6H),3.52(s,4H),3.67(d,2H),6.98(d,2H),7.02(s,1H),7.30–7.50(m,9H),7.50–7.61(m,4H),7.81–7.92(m,5H).
2)化合物D-3的合成
在氩气氛围下，向反应容器中加入化合物D-3-1 55.1g(100mmol),化合物D-3-C23.2g(100mmol),叔丁醇钠23.1g(240mmol)，双二亚苄基丙酮钯575毫g(1mmol％),2-双环己基膦-2',4',6'-三异丙基联苯953毫g(2mmol％)和1000mL二甲苯(xylene),在140℃加热搅拌20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/己烷)，得到54.9g化合物D-3，HPLC纯度99.9％，收率78％.LC MS：M/Z 703.32(M+)。1H NMR(400MHz,DMSO-d6)δ1.69(s,6H),3.52(s,4H),3.67(d,2H),6.98(d,2H),7.30–7.61(m,21H),7.69–7.77(m,2H),7.81–7.92(m,4H).
实施例2
化合物D-22的合成
Figure BDA0003829961770000211
除了起始原料更换为D-22-B以外，其他与实施例1相同。LC MS:M/Z 729.30(M+)。HPLC纯度：99.9％，总收率：53％；1H NMR(400MHz,DMSO-d6)δ3.42(d,2H),3.52(s,3H),3.67(d,2H),7.08(s,2H),7.18(m,1H),7.27(m,1H),7.30–7.61(m,18H),7.65–7.84(m,6H),7.84–7.93(m,4H).
实施例3
化合物D-30的合成
Figure BDA0003829961770000212
除了起始原料更换为D-30-A、D-30-B和D-30-C以外，其他与实施例1相同。LC MS:M/Z 744.31(M+)。合成总收率：55％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ3.42(d,2H),3.52(s,4H),3.67(s,2H),6.54(s,2H),6.95–7.05(m,3H),7.05–7.12(m,2H),7.12–7.28(m,6H),7.28–7.37(m,3H),7.37–7.48(m,3H),7.48(m,4H),7.53–7.67(m,5H),7.70–7.78(m,2H),7.96–8.04(m,2H).
实施例4
化合物D-39的合成
Figure BDA0003829961770000213
除了起始原料更换为D-39-A和D-39-C以外，其他与实施例1相同。LC MS:M/Z775.33(M+)。合成总收率：55％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ1.69(s,12H),3.52(d,4H),3.67(d,2H),6.73(m,2H),6.93–7.12(m,8H),7.30–7.61(m,10H),7.61–7.67(m,1H),7.81–7.95(m,3H),7.99(m,1H),8.45(m,2H).
实施例5
化合物D-48的合成
Figure BDA0003829961770000221
除了起始原料更换为D-48-A和D-48-B以外，其他与实施例1相同。LC MS:M/Z677.27(M+)。合成总收率：53％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ3.42(d,2H),3.52(s,4H),3.67(d,2H),6.91(m,1H),7.19(m,1H),7.26–7.61(m,19H),7.68(m,1H),7.70–7.77(m,2H),7.84–7.92(m,1H),7.94–8.06(m,2H).
实施例6
化合物D-55的合成
Figure BDA0003829961770000222
除了起始原料更换为D-48-A和D-55-B以外，其他与实施例1相同。LC MS:M/Z693.27(M+)。合成总收率：48％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ3.42(d,2H),3.52(s,4H),3.67(d,2H),6.48(m,1H),6.77–6.90(m,4H),6.94(m,2H),7.19(m,1H),7.28–7.61(m,16H),7.69–7.77(m,2H),7.84–7.92(m,1H).
实施例7
化合物D-68的合成
Figure BDA0003829961770000223
除了起始原料更换为D-68-A以外，其他与实施例1相同，LC MS:M/Z 856.38(M+)；合成总收率：50％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ1.69(s,6H),3.52(s,4H),3.80(s,2H),6.95–7.01(m,1H),7.10(d,1H),7.20(m,2H),7.30–7.60(m,25H),7.69–7.80(m,3H),7.81–7.92(m,4H).
实施例8
化合物D-78的合成
Figure BDA0003829961770000231
除了起始原料更换为D-68-A和D-78-B以外，其他与实施例1相同。LC MS:M/Z921.37(M+)。合成总收率：51％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ3.52(s,4H),3.80(s,2H),6.65(m,1H),6.77(d,2H),6.94–7.05(m,3H),7.02–7.14(m,5H),7.18(m,1H),7.19–7.29(m,3H),7.30–7.60(m,21H),7.69–7.80(m,3H),7.88(m,2H).
实施例9
化合物D-85的合成
Figure BDA0003829961770000232
除了起始原料更换为D-85-A和D-85-B以外，其他与实施例1相同。LC MS:M/Z850.43(M+)。合成总收率：51％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ1.22(d,12H),1.48(s,4H),3.52(s,4H),3.80(s,2H),6.45(m,1H),6.70(m,1H),7.10(d,1H),7.24(m,1H),7.30–7.60(m,24H),7.69–7.77(m,2H),7.88(m,2H).
实施例10
化合物D-98的合成
Figure BDA0003829961770000233
除了起始原料更换为D-98-A和D-98-B以外，其他与实施例1相同。LC MS:M/Z806.33(M+)。合成总收率：51％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ3.52(s,4H),3.80(s,2H),7.10(d,7H),7.30–7.61(m,21H),7.69–7.76(m,2H),7.76–7.85(m,2H),7.85–7.93(m,4H).
实施例11
化合物D-130的合成
Figure BDA0003829961770000241
除了起始原料更换为D-98-A和D-85-B以外，其他与实施例1相同。LC MS:M/Z806.37(M+)。合成总收率：54％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ1.22(d,12H),1.48(s,4H),3.52(s,4H),3.80(s,2H),6.45(m,1H),6.66–6.78(m,2H),6.99(m,1H),7.03–7.16(m,6H),7.20–7.30(m,2H),7.30–7.60(m,12H),7.69–7.77(m,4H).
实施例12
化合物D-138的合成
Figure BDA0003829961770000242
除了起始原料更换为D-138-A、D-78-B和D-138-C以外，其他与实施例1相同。LCMS:M/Z 928.41(M+)。合成总收率：51％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ1.68–1.92(m,6H),2.71(m,2H),2.83(m,2H),3.52(s,4H),3.80(s,2H),6.65(m,1H),6.70–6.81(m,3H),6.94–7.15(m,17H),7.15–7.25(m,2H),7.20–7.31(m,10H),7.40(d,1H),7.45(d,1H),7.56(d,1H).
实施例13
化合物D-143的合成
Figure BDA0003829961770000243
除了起始原料更换为D-143-A和D-143-B以外，其他与实施例1相同。LC MS:M/Z1042.34(M+)。合成总收率：55％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ3.52(s,4H),3.55(s,4H),6.95–7.00(m,2H),7.03(m,2H),7.30–7.44(m,11H),7.44–7.61(m,13H),7.61–7.67(m,2H),7.69–7.77(m,4H),7.85(d,2H),7.91(m,2H),7.99(m,2H),8.45(m,2H)
实施例14
化合物D-155的合成
Figure BDA0003829961770000251
除了起始原料更换为D-143-A和D-155-C以外，其他与实施例1相同。LC MS:M/Z940.39(M+)。合成总收率：54％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ1.69(s,12H),3.52(s,4H),3.55(s,4H),6.95–7.00(m,4H),7.03(m,2H),7.30–7.61(m,18H),7.61–7.67(m,2H),7.81–7.95(m,8H),7.99(m,2H),8.41–8.49(m,2H)
实施例15
化合物D-164的合成
Figure BDA0003829961770000252
除了起始原料更换为D-164-A和D-48-B以外，其他与实施例1相同。LC MS:M/Z1052.43(M+)。合成总收率：56％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ1.69(s,6H),3.52(s,4H),3.54(s,4H),6.91(m,2H),6.94–7.06(m,4H),7.09(d,2H),7.26–7.61(m,24H),7.64–7.77(m,6H),7.94–8.06(m,4H).
实施例16
化合物D-177的合成
Figure BDA0003829961770000253
除了起始原料更换为D-164-A、D-143-B和D-177-C以外，其他与实施例1相同。LCMS:M/Z 1164.45(M+)。合成总收率：53％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ1.69(s,18H),3.52(s,4H),3.55(s,4H),6.93–7.00(m,4H),7.00–7.06(m,4H),7.09(d,2H),7.30–7.61(m,16H),7.61–7.67(m,2H),7.81–7.95(m,6H),7.99(m,2H),8.45(m,2H).
实施例17
化合物D-219的合成
Figure BDA0003829961770000261
除了起始原料更换为D-219-A和D-48-B以外，其他与实施例1相同。LC MS:M/Z677.27(M+)。合成总收率：53％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ3.11(s,4H),6.91(m,1H),6.95–7.01(m,1H),7.20–7.58(m,20H),7.68(m,1H),7.69–7.82(m,4H),7.82–7.92(m,2H),7.94–8.06(m,2H).
实施例18
化合物D-237的合成
Figure BDA0003829961770000262
除了起始原料更换为D-237-A和D-48-B以外，其他与实施例1相同。LC MS:M/Z754.30(M+)。合成总收率：52％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ3.36(s,4H),6.74(m,1H),6.91(m,1H),6.99(m,1H),7.13(t,1H,),7.19–7.37(m,5H),7.32–7.41(m,5H),7.37–7.44(m,1H),7.41–7.49(m,3H),7.44–7.53(m,2H),7.49–7.58(m,5H),7.64–7.82(m,4H),7.88(m,2H),7.94–8.06(m,2H),8.24(m,1H).
实施例19
化合物D-251的合成
Figure BDA0003829961770000263
除了起始原料更换为D-251-A、D-48-B和D-177-C以外，其他与实施例1相同。LCMS:M/Z 733.30(M+)。合成总收率：55％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ1.69(s,6H),2.98(m,2H),3.23(m,2H),6.91(m,1H),6.95–7.06(m,3H),7.12–7.23(m,4H),7.20–7.33(m,3H),7.28–7.41(m,7H),7.41–7.50(m,2H),7.50–7.58(m,2H),7.68(m,1H),7.78(m,2H),7.82–7.92(m,2H),7.94–8.06(m,2H).
实施例20
化合物D-273的合成
Figure BDA0003829961770000271
除了起始原料更换为D-273-A和D-273-B以外，其他与实施例1相同。LC MS:M/Z851.42(M+)。合成总收率：55％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ1.22(s,12H),1.48(s,4H),6.45(m,1H),7.00(d,1H),7.02–7.13(m,6H),7.24(m,2H),7.29–7.36(m,4H),7.32–7.42(m,8H),7.38–7.55(m,7H),7.51–7.58(m,2H),7.69–7.77(m,2H),7.88(m,2H),8.24(m,2H).
实施例21
化合物E-2的合成
Figure BDA0003829961770000272
1)中间体E-2-1的合成
氩气氛围下，反应器中加入E-2-B 39.1g(100mmol)、E-2-A 38.8g(100mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME)，80℃加热搅拌一晚。冷却至室温，加入500ml水，固体析出，过滤，得到的固体用乙醇洗涤，得到41.2g的化合物E-4-1,收率63％，HPLC纯度99.1％。LC MS:M/Z 653.15(M+)；1HNMR(400MHz,DMSO-d6)δ3.42(s,4H),3.67(s,4H),7.30–7.62(m,13H),7.69–7.81(m,3H),7.84–7.96(m,3H),8.08(m,1H).
2)化合物E-2的合成
氩气氛围下，反应器中加入E-2-1 65.5g(100mmol)、E-2-C 17.2g(100mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME)，80℃加热搅拌一晚。冷却至室温，加入500ml水，固体析出，过滤，得到的固体用乙醇洗涤，得到55.4g的化合物E-2,收率79％，HPLC纯度99.9％。LC MS:M/Z 701.28(M+)；1H NMR(400MHz,DMSO-d6)δ3.42(s,4H),3.67(s,4H),7.30–7.50(m,6H),7.46–7.55(m,1H),7.50–7.59(m,3H),7.55–7.68(m,5H),7.69–7.81(m,3H),7.84–7.96(m,3H),7.96–8.05(m,1H),8.08(m,2H),8.11–8.20(m,1H),8.45–8.53(m,1H),9.06–9.12(m,1H).
实施例22
化合物E-13的合成
Figure BDA0003829961770000281
除了起始原料更换为E-13-A、E-13-B和E-13-C以外，其他与实施例21相同。LC MS:M/Z 666.21(M+)。合成总收率：48％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ3.52(s,4H),6.34(d,2H),7.14(d,2H),7.26–7.39(m,2H),7.40–7.58(m,7H),7.63–7.76(m,3H),7.76(m,1H),7.84–7.95(m,2H),7.95–8.02(m,1H),8.15–8.21(m,1H),8.30–8.40(m,2H)
实施例23
化合物E-26的合成
Figure BDA0003829961770000282
除了起始原料更换为E-26-A、E-13-B和E-13-C以外，其他与实施例21相同。LC MS:M/Z 685.20(M+)。合成总收率：47％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ3.52(s,4H),6.34(d,2H),7.05(m,1H),7.14(d,2H),7.18–7.26(m,2H),7.31(m,1H),7.37–7.64(m,8H),7.70(m,1H),7.76(m,1H),7.91(m,1H),7.99(m,2H),8.30–8.40(m,2H).
实施例24
化合物E-37的合成
Figure BDA0003829961770000283
除了起始原料更换为E-37-A、E-37-B和E-37-C以外，其他与实施例21相同。LC MS:M/Z 670.24(M+)。合成总收率：45％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ3.52(s,4H),6.34(d,2H),6.94–7.04(m,2H),7.04–7.11(m,2H),7.11–7.20(m,3H),7.20–7.29(m,2H),7.29(m,1H),7.41(m,1H),7.44–7.55(m,6H),7.60(d,1H),7.80(d,1H),7.93(m,1H),8.30–8.40(m,4H).
实施例25
化合物E-47的合成
Figure BDA0003829961770000291
除了起始原料更换为E-47-A、E-37-B和E-37-C以外，其他与实施例21相同。LC MS:M/Z 697.27(M+)。合成总收率：40％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ1.69(s,6H),3.52(s,4H),6.34(d,2H),6.73(m,2H),7.02–7.10(m,2H),7.14(d,2H),7.25(d,1H),7.44–7.62(m,9H),7.65(d,1H),7.88–7.96(m,2H),8.30–8.40(m,4H).
实施例26
化合物E-56的合成
Figure BDA0003829961770000292
除了起始原料更换为E-56-A、E-37-B和E-56-C以外，其他与实施例21相同。LC MS:M/Z 665.25(M+)。合成总收率：44％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ3.11(d,4H),7.20–7.40(m,8H),7.40–7.60(m,8H),7.70(m,1H),7.73–7.82(m,4H),7.84–7.95(m,2H),7.98(m,1H),8.08(m,1H),8.29–8.41(m,2H).
实施例27
化合物E-70的合成
Figure BDA0003829961770000293
除了起始原料更换为E-70-A、E-70-B和E-70-C以外，其他与实施例21相同。LC MS:M/Z 747.23(M+)。合成总收率：42％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ2.98(m,2H),3.23(m,2H),7.01(m,1H),7.12–7.40(m,10H),7.48(m,1H),7.56(m,1H),7.56–7.68(m,2H),7.71(d,1H),7.78(m,2H),7.87–7.96(m,3H),7.96–8.05(m,1H),8.08(d,1H),8.12–8.20(m,1H),8.17–8.26(m,2H),8.41–8.53(m,2H),9.09(t,1H).
实施例28
化合物E-79的合成
Figure BDA0003829961770000301
除了起始原料更换为E-79-A、E-37-B和E-37-C以外，其他与实施例21相同。LC MS:M/Z 617.28(M+)。合成总收率：45％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ1.69(s,6H),2.98(m,2H),3.23(m,2H),6.73(m,2H),7.06(m,2H),7.20–7.33(m,3H),7.29–7.40(m,4H),7.44–7.57(m,7H),7.65(d,1H),7.78(m,2H),8.29–8.41(m,4H).
实施例29
化合物E-92的合成
Figure BDA0003829961770000302
除了起始原料更换为E-92-B以外，其他与实施例21相同。LC MS:M/Z 536.23(M+)。合成收率：73％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ3.42(s,4H),3.67(s,4H),7.28(m,1H),7.35(m,3H),7.41(d,2H),7.41–7.56(m,4H),7.52–7.60(m,3H),7.56–7.66(m,2H),7.73–7.84(m,2H),7.84–7.92(m,1H),8.04–8.12(m,1H),8.52–8.60(m,1H).
实施例30
化合物E-109的合成
Figure BDA0003829961770000303
除了起始原料更换为E-109-A、E-109-B和E-70-C以外，其他与实施例21相同。LCMS:M/Z 610.17(M+)。合成总收率：43％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ3.42(s,4H),3.67(s,4H),7.01(m,1H),7.12–7.24(m,3H),7.32(m,1H),7.37–7.52(m,4H),7.56(t,3H),7.71(d,1H),7.86–7.95(m,2H),7.99(m,1H),8.12(d,1H),8.41–8.49(m,1H)。
实施例31
化合物E-133的合成
Figure BDA0003829961770000311
除了起始原料更换为E-109-A、E-109-B和E-70-C以外，其他与实施例21相同。LCMS:M/Z 610.17(M+)。合成总收率：43％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ1.69(s,6H),3.42(s,4H),3.67(s,4H),6.73(m,2H),7.02–7.11(m,2H),7.25–7.45(m,5H),7.47–7.61(m,3H),7.78(m,2H),7.82–7.92(m,2H),8.04–8.13(m,3H),8.21(d,1H).
实施例32
化合物E-144的合成
Figure BDA0003829961770000312
除了起始原料更换为E-56-A以外，其他与实施例21相同。LC MS:M/Z 701.28(M+)。合成总收率：43％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ3.11(s,4H),7.20–7.68(m,17H),7.69–7.82(m,5H),7.84–7.96(m,3H),7.96–8.05(m,1H),8.08(d,2H),8.11–8.20(m,1H),8.45–8.53(m,1H),9.09(t,1H).
实施例33
化合物E-153的合成
Figure BDA0003829961770000313
除了起始原料更换为E-153-A和E-153-B以外，其他与实施例21相同。LC MS:M/Z694.26(M+)。合成收率：65％；HPLC纯度：99.9％。
实施例34
化合物E-163的合成
Figure BDA0003829961770000321
除了起始原料更换为E-163-A和E-163-B以外，其他与实施例21相同。LC MS:M/Z556.18(M+)。合成收率：68％；HPLC纯度：99.9％。
实施例35
化合物H-1的合成
Figure BDA0003829961770000322
除了起始原料更换为H-1-B和H-1-C以外，其他与实施例1相同。LC MS:M/Z 829.32(M+)。合成收率：41％；HPLC纯度：99.9％。1H NMR(400MHz,DMSO-d6)δ3.42(s,4H),3.67(s,4H),7.19(m,1H),7.30–7.37(m,1H),7.32–7.39(m,1H),7.34–7.48(m,5H),7.44–7.52(m,1H),7.48–7.58(m,9H),7.57(d,2H),7.60–7.70(m,3H),7.84–7.92(m,1H),7.99–8.07(m,1H),8.16–8.24(m,2H),8.30–8.40(m,4H).
实施例36
化合物H-12的合成
Figure BDA0003829961770000323
1)中间体H-12-1的合成
氩气氛围下，反应器中加入H-12-B 41.1g(100mmol)、H-12-A 38.8g(100mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME)，80℃加热搅拌一晚。冷却至室温，加入500ml水，固体析出，过滤，得到的固体用乙醇洗涤，得到53.3g的化合物H-12-1，收率79％，HPLC纯度99.1％。LC MS:M/Z 674.27(M+)；1HNMR(400MHz,DMSO-d6)δ3.42(s,4H),3.67(s,4H),7.24–7.76(m,22H),7.84–7.92(m,1H),8.15–8.21(m,1H),8.24(m,1H),8.32–8.40(m,1H),8.64(d,1H).
2)H-12的合成
在氩气氛围下，向反应容器中加入化合物H-12-1 67.5g(100mmol),化合物H-12-C28.5g(100mmol),叔丁醇钠23.1g(240mmol)，双二亚苄基丙酮钯575毫g(1mmol％),2-双环己基膦-2',4',6'-三异丙基联苯953毫g(2mmol％)和1000mL二甲苯(xylene),在140℃加热搅拌20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/己烷)，得到71.2g化合物H-12，HPLC纯度99.9％，收率81％.LC MS：M/Z 878.34(M+)。1H NMR(400MHz,DMSO-d6)δ3.42(s,4H),3.67(s,4H),7.30–7.84(m,27H),7.84–7.92(m,1H),8.15–8.28(m,3H),8.27(m,1H),8.64(m,1H),9.03(d,1H).
实施例37
化合物H-26的合成
Figure BDA0003829961770000331
除了起始原料更换为D-143-A、H-26-B和H-26-C以外，其他与实施例36相同。LCMS:M/Z 744.25(M+)。合成总收率：38％；HPLC纯度：99.9％。
实施例38
化合物H-37的合成
Figure BDA0003829961770000332
除了起始原料更换为D-143-A、H-37-B和H-37-C以外，其他与实施例36相同。LCMS:M/Z 769.27(M+)。合成总收率：38％；HPLC纯度：99.9％。
实施例39
化合物H-48的合成
Figure BDA0003829961770000341
1)中间体H-48-1的合成
在氩气氛围下，向反应容器中加入化合物H-48-A 42.3g(100mmol),化合物H-48-B19.1g(100mmol),叔丁醇钠23.1g(240mmol)，双二亚苄基丙酮钯575毫g(1mmol％),2-双环己基膦-2',4',6'-三异丙基联苯953毫g(2mmol％)和1000mL二甲苯(xylene),在140℃加热搅拌20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/己烷)，得到29.9g化合物H-48-1，HPLC纯度99.9％，收率56％.LC MS：M/Z 532.17(M+)。1H NMR(400MHz,DMSO-d6)δ3.52(s,4H),7.01–7.13(m,5H),7.20–7.28(m,2H),7.29–7.50(m,10H),7.50–7.57(m,2H),7.88(m,2H).
2)化合物H-48的合成
氩气氛围下，反应器中加入H-48-1 53.3g(100mmol)、H-48-C 27.7g(100mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME)，80℃加热搅拌一晚。冷却至室温，加入500ml水，固体析出，过滤，得到的固体用乙醇洗涤，得到54.7g的化合物H-48,收率75％，HPLC纯度99.9％。LC MS:M/Z 729.29(M+)；1HNMR(400MHz,DMSO-d6)δ3.52(s,4H),7.01–7.13(m,3H),7.29–7.57(m,21H),7.88(m,2H),8.00–8.08(m,2H),8.30–8.40(m,4H).
实施例40
化合物H-60的合成
Figure BDA0003829961770000342
除了起始原料更换为H-60-A以外，其他与实施例35相同。LC MS:M/Z 829.32(M+)。合成总收率：39％；HPLC纯度：99.9％。
实施例41
化合物H-69的合成
Figure BDA0003829961770000351
除了起始原料更换为D-219-A、H-69-B和H-69-C以外，其他与实施例36相同。LCMS:M/Z 878.34(M+)。合成总收率：40％；HPLC纯度：99.9％。
实施例42
化合物H-76的合成
Figure BDA0003829961770000352
除了起始原料更换为H-76-A、H-76-B和H-26-C以外，其他与实施例36相同。LC MS:M/Z 713.28(M+)。合成总收率：41％；HPLC纯度：99.9％。
实施例43
化合物H-90的合成
Figure BDA0003829961770000353
除了起始原料更换为H-90-A、H-76-B和H-26-C以外，其他与实施例36相同。LC MS:M/Z 713.28(M+)。合成总收率：41％；HPLC纯度：99.9％。
实施例44
化合物H-107的合成
Figure BDA0003829961770000354
除了起始原料更换为H-90-A、H-76-B和H-26-C以外，其他与实施例36相同。LC MS:M/Z 713.28(M+)。合成总收率：41％；HPLC纯度：99.9％。
器件实施例1：有机电致发光器件的制备
Figure BDA0003829961770000361
制备过程如下：
1)在玻璃基板上形成透明阳极ITO膜层(厚度150nm)，得到第一电极作为阳极。
2)通过真空蒸发，在阳极表面上蒸发化合物T-1和化合物T-2的混合材料作为空穴注入层，混合比(质量比)为3：97，厚度为10nm。
3)在空穴注入层上蒸发厚度为100nm的化合物T-2以获得第一空穴传输层。然后，在第一空穴传输层上蒸发厚度为10nm的本发明的化合物D-3，以获得第二空穴传输层。
4)在第二空穴传输层上，化合物T-3和化合物T-4以95：5的质量比共蒸发，形成厚度为40nm的有机发光层。
5)在有机发光层上，依次蒸发化合物T-5以形成空穴阻挡层(厚度10nm)，混合比为4：6(质量比)的化合物T-6和LiQ形成电子传输层(厚度30nm)。
6)将镁(Mg)和银(Ag)以1：9的蒸发速率混合，真空蒸发在作为第二电极的电子注入层上，完成有机发光器件的制作。
器件实施例2～20
除了在形成第二空穴传输层时，分别以化合物D-22、D-30、D-39、D-48、D-55、D-68、D-78、D-85、D-98、D-130、D-138、D-143、D-155、D-164、D-177、D-219、D-237、D-251和D-273替代化合物D-3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1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。
以上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1-20、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
第二空穴传输层 相对工作电压 相对效率 相对寿命
器件对比例1 HT-1 1 1 1
器件对比例2 HT-2 1.07 1.03 1.43
器件实施例1 D-3 0.96 1.12 1.34
器件实施例2 D-22 0.95 1.13 1.32
器件实施例3 D-30 0.96 1.13 1.10
器件实施例4 D-39 0.95 1.15 1.22
器件实施例5 D-48 0.94 1.11 1.36
器件实施例6 D-55 0.94 1.13 1.27
器件实施例7 D-68 0.95 1.16 1.18
器件实施例8 D-78 0.95 1.10 1.29
器件实施例9 D-85 0.96 1.17 1.38
器件实施例10 D-98 0.96 1.16 1.29
器件实施例11 D-130 0.97 1.16 1.18
器件实施例12 D-138 0.98 1.16 1.25
器件实施例13 D-143 0.94 1.17 1.23
器件实施例14 D-155 0.96 1.19 1.18
器件实施例15 D-164 0.97 1.18 1.36
器件实施例16 D-177 0.99 1.17 1.29
器件实施例17 D-219 0.94 1.10 1.16
器件实施例18 D-237 0.98 1.15 1.28
器件实施例19 D-251 0.99 1.10 1.34
器件实施例20 D-273 0.96 1.17 1.39
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1～20所使用的化合物与器件对比例1和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(最高达到19％)，寿命提高高达40％以上。
器件实施例21：有机电致发光器件的制备
Figure BDA0003829961770000371
将涂有厚度为100nm的氧化铟锡(ITO)作为薄膜的玻璃基板放入溶解有清洁剂的蒸馏水中，并进行超声波清洗。清洗ITO 20分钟后，用蒸馏水重复超声波清洗两次，每次10分钟。用蒸馏水洗涤后，用异丙醇、丙酮和甲醇通过超声波清洗基底，然后干燥并转移到等离子体清洁器中。此外，用氧等离子体清洗衬底5分钟，然后转移到真空中沉积器。在如上制备的透明ITO电极上，通过以0.04至0.09nm/s的沉积速率和60nm的总膜厚度热真空沉积化合物HI来形成空穴注入层，然后依次进行如下操作：
1)在空穴注入层上真空蒸镀化合物HAT作为第一空穴传输层，蒸镀速度0.04～0.09nm/s，蒸镀总膜厚为5nm。
2)在第一空穴传输层上真空蒸镀HT作为第二空穴传输层.蒸镀率为0.04～0.09nm/s，蒸镀总膜厚为50nm。
3)通过以重量比25:1真空蒸镀化合物BH和化合物BD而在第2层空穴输送层上形成发光层，蒸镀率为0.04～0.09nm/s，蒸镀总膜厚为20nm。
4)在发光层上，通过以重量比1:1真空蒸镀化合物E-2和化合物LiQ而形成电子输送层和注入层，蒸镀速率为0.1nm/s，蒸镀总膜厚为35nm。
5)在电子注入及输送层上，以蒸镀速度0.03nm/s、总膜厚1nm的厚度蒸镀氟化锂(LiF)后，以蒸镀速度0.2nm/s、总膜厚100nm堆积铝，形成阴极。
在这个过程中真空度保持在1×10-7到5×10-5托。
器件实施例22～34
除了在形成电子传输层时，分别以化合物E-13、E-26、E-37、E-47、E-56、E-70、E-79、E-92、E-109、E-133、E-144、E-153和E-163替代化合物E-2外，采用与器件实施例21相同的方法制作有机电致发光器件。
器件对比例3～4
Figure BDA0003829961770000381
除了在形成发光层时，以化合物ET1和ET2替代化合物E-2外，采用与器件实施例21相同的方法制作有机电致发光器件。
表2
Figure BDA0003829961770000382
Figure BDA0003829961770000391
根据表2的结果可知，本发明系列化合物代替器件对比例3和4中已商品化的电子传输材料ET1和ET2作发光器件的电子传输层时，实现了电压降低，提升了电流效率的技术效果。以上结果表明，本发明的新型有机材料作为有机电致发光器件的电子传输材料，是性能良好的有机发光功能材料，有望推广商业化应用。
器件实施例35：有机电致发光器件的制备
Figure BDA0003829961770000392
有机光电器件的基本结构模型为：ITO/HAT-CN(10nm)/TAPC(40nm)/TCTA(10nm)/EML(本发明的化合物):RD(Ir配合物)＝94:6(40nm)/ETL(30nm)/LiF(1nm)/Al(80nm)。
本发明有机光电器件的制造方法：
(1)依次用丙酮、乙醇和蒸馏水对透明阳极氧化铟锡(ITO)20(10Ω/sq)玻璃基板进行超声清洗,再用臭氧等离子处理15分钟。
(2)在真空气相蒸镀设备的衬底固定器上安装ITO衬底后，控制体系压力在10-6托，接着向ITO衬底上依次蒸镀厚度为10nm的HAT-CN，40nm的TAPC和10nm的TCTA。
(3)在上述TCTA上蒸镀厚度为40nm的发光层(EML)，其中本发明化合物H-1与RD的质量比为94：6。
(4)在上述发光层上蒸镀厚度为30nm的电子传输层(ETL)材料。
(5)在上述电子传输层上蒸镀厚度为1nm的LiF作为电子注入层。
(6)最后在上述电子注入层上蒸镀厚度为80nm的Al作为阴极，且利用玻璃封装盖对器件进行封装。
器件实施例36～44
除了在形成发光层时，分别以化合物H-12、H-26、H-37、H-48、H-60、H-69、H-76、H-90、和H-107替代化合物H-1外，采用与器件实施例35相同的方法制作有机电致发光器件。
器件对比例5～6
除了在形成发光层时，分别以化合物RH-01、化合物RH-02替代化合物1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。
表3
Figure BDA0003829961770000401
根据表3的结果可知，作发光器件的发光层时，器件实施例35～44所使用的化合物与器件对比例5～6中使用的化合物形成的器件相比，发光效率均有所提高(最高达到20％)，寿命提高高达40％以上。
据此，上述实施例和对比例中的器件结构除了对应的功能层不同外，其它均一致，基于对比材料的器件性能为参考，包含本发明的化合物的器件电流效率有显著提升，同时其寿命也有所提升。以上结果表明，本发明的化合物作为有机电致发光器件的电子传输材料、空穴传输材料和主体材料是性能良好的有机发光功能材料，有望推广商业化应用。
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，其化学结构如式(Ⅰ)所示：
Figure FDA0003829961760000011
式(Ⅰ)中，A选自
Figure FDA0003829961760000012
或
Figure FDA0003829961760000013
Z1和Z2分别选自-CR17R18-、-NR19-、S或O；
X选自单键、-CR20R21-、-NR22-、S或O；
R1～R22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。
2.根据权利要求1所述的化合物，其特征在于，式(Ⅰ)中，R1～R8至少一个选自如下任一个结构：
Figure FDA0003829961760000014
其中，B和C独立选自取代或未取代的C6～C60芳基、取代或未取代的C5～C60杂芳基、或选自如下任一个结构：
Figure FDA0003829961760000015
E选自含氟原子的吸电子基团、含氮原子的吸电子基团或含氧的吸电子基团；
Ar1～Ar8相同或不同，独立选自取代或未取代的C6～C60芳基、取代或未取代的C5～C60杂芳基；
X1～X13相同或不同，独立选自O、S、-CR25R26-、-NR27-或-SiR28R29-；
L1～L9相同或不同，独立选自不存在、单键、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～C60芳基、取代或未取代的C5～C60杂芳基；
R23～R29相同或不同，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～C60芳基、取代或未取代的C5～C60杂芳基；
*为连接位点。
3.根据权利要求1所述的化合物，其特征在于，所述化合物选自以下化学结构中的一种或多种：
Figure FDA0003829961760000021
Figure FDA0003829961760000031
Figure FDA0003829961760000041
Figure FDA0003829961760000051
Figure FDA0003829961760000061
Figure FDA0003829961760000071
Figure FDA0003829961760000081
Figure FDA0003829961760000091
Figure FDA0003829961760000101
Figure FDA0003829961760000111
Figure FDA0003829961760000121
Figure FDA0003829961760000131
4.一种有机层，包括权利要求1～3中任一项所述的化合物。
5.权利要求1～3中任一项所述的化合物和/或权利要求4所述的有机层在有机光电器件中的应用。
6.一种有机光电器件，其包括第一电极、第二电极和权利要求4所述的有机层，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。
7.根据权利要求6所述的有机光电器件，其特征在于，所述有机层的电子传输层材料包含权利要求1～3任一项所述化合物中的一种或多种。
8.根据权利要求6所述的有机光电器件，其特征在于，所述有机层的发光层材料包含权利要求1～3任一项所述化合物中的一种或多种。
9.根据权利要求6所述的有机光电器件，其特征在于，所述有机层的空穴传输层材料包含权利要求1～3任一项所述化合物中的一种或多种。
10.根据权利要求6～9任一项所述的有机光电器件，其特征在于，所述有机光电器件选自有机光伏器件、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，其包括权利要求6～9任一项所述的有机光电器件。
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