CN110156740B - 杂螺二芴类有机电致发光化合物及其制备方法和有机电致发光装置 - Google Patents

杂螺二芴类有机电致发光化合物及其制备方法和有机电致发光装置 Download PDF

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CN110156740B
CN110156740B CN201910451142.2A CN201910451142A CN110156740B CN 110156740 B CN110156740 B CN 110156740B CN 201910451142 A CN201910451142 A CN 201910451142A CN 110156740 B CN110156740 B CN 110156740B
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compound
substituted
organic electroluminescent
unsubstituted
aromatic ring
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CN110156740A (zh
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马晓宇
汪康
陈明
王辉
王永光
王士凯
王进政
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

本发明涉及一种杂螺二芴类有机电致发光化合物及其制备方法和有机电致发光装置，所述杂螺二芴类有机电致发光化合物由以下化学式1表示：

Description

杂螺二芴类有机电致发光化合物及其制备方法和有机电致发 光装置
技术领域
本发明涉及有机发光材料技术领域，具体涉及一种杂螺二芴类有机电致发光化合物及其制备方法和有机电致发光装置。
背景技术
电致发光装置(EL装置)为自动发光装置，其优点在于其提供较宽的视角、较大的对比率和较快的响应时间。
在这种有机发光二极管中，当在阳极和阴极之间施加电压时，来自阳极的空穴和来自阴极的电子注入有机材料层。产生的激子在迁移至基态时产生具有特定波长的光。它具有如下结构：阳极、阴极以及介于两者之间的有机材料层。为了提高有机EL元件的效率和稳定性，有机材料层包括具有不同材料的多层，例如空穴注入层(HIL)、空穴传输层(HTL)、发光层、电子传输层(ETL)和电子注入层(EIL)。其中，具有传输空穴功能的层例如空穴注入层、空穴传输层、电子阻挡层等可改变空穴到发光层的空穴传输效率、发光效率、寿命等，对电子器件的性能数据具有巨大影响。
现有技术中使用芳基胺作为具有空穴传输性能的材料。有些为单芳基胺，如WO2016/006709公开的含有螺二芴结构的单三芳胺化合物，还有些为二胺或其它多胺，如JP2000200685和EP0779765中分别公开的星状芳胺。目前已经实际用于OLED的具有空穴传输性质的材料为三芳基胺化合物三-对联苯胺、N,N'-二-1-萘基-N,N'-二苯基-1,1'-联苯-4,4'-二胺(NPB)和4,4',4”-三-(3-甲基苯基-苯基氨基)-三苯基胺(MTDATA)。上述材料的使用可以改善有机EL器件的性能数据，如寿命、效率和工作电压等。但是由上述材料制备的有机EL器件的性能仍存在较大的改进空间，更好的满足实际应用的需求。因此需要不断探索具有相应性质的新型材料。
发明内容
本发明要解决现有技术中的技术问题，提供一种杂螺二芴类有机电致发光化合物及其制备方法和有机电致发光装置，本发明的杂螺二芴类有机电致发光化合物非常适用于OLED中，其特别适用于空穴传输层中。所述的杂螺二芴类有机电致发光化合物具有非常好的空穴传输性质、非常好的电子阻挡性质、以及良好的热稳定性。在用于OLED中时，其导致OLED具有长的寿命、高的量子效率和低的工作电压。
为了解决上述技术问题，本发明的技术方案具体如下：
本发明提供一种杂螺二芴类有机电致发光化合物，其结构式如化学式1所示：
Figure BDA0002075182960000021
其中：
Ar1和Ar2各自独立地表示经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C60芳基、或经取代或未经取代的1到30元杂芳基；或与相邻取代基连接形成单环或多环、具体为C3-C60脂肪族环或芳香族环，其碳原子可置换为至少一个选自氮、氧和硫的杂原子；并且当Ar1、Ar2有取代基时，可被一个或多个R6取代；
R1表示经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C60芳基、或经取代或未经取代的1到30元杂芳基；或与相邻取代基连接形成单环或多环、具体为C3-C60脂肪族环或芳香族环，其碳原子可置换为至少一个选自氮、氧和硫的杂原子；并且当R1上有取代基时，可被一个或多个R7取代；
R2、R3、R4和R5各自独立地表示氢、氘、卤素、氰基、羧基、硝基、羟基、胺基、经取代或未经取代的C1-C30烃基、经取代或未经取代的C1-C30烷氧基、经取代或未经取代的C3-C30环烷基、经取代或未经取代的C3-C30环烯基、经取代或未经取代的1到30元杂环烷基、经取代或未经取代的C6-C60芳基、或经取代或未经取代的1到30元杂芳基；或与相邻取代基连接形成经取代或未经取代的单环或多环、具体为C3-C60脂肪族环或芳香族环，其碳原子可置换成至少一个选自氮、氧和硫的杂原子；并且当R2、R3、R4和R5上有取代基时，均可被一个或多个R8取代；
R6、R7和R8各自独立地选自氢、氘、卤素、氰基、羧基、硝基、羟基、胺基、C(＝O)R9、CF3、OCF3、Si(R9)3、N(R9)2、P(＝O)(R9)2、S(＝O)R9、S(＝O)2R9、C1-C20的直链烷基、C1-C20的直链烷氧基、C3-C20的支链烷基、C3-C20的环状烷基、C3-C20的支链烷氧基、C3-C20的环状烷氧基、C3-C20的烯基、C3-C20的炔基、具有1～40个芳族环原子的芳族环系、或具有1～40个芳族环原子的杂芳族环系；其中R6、R7和R8中的两个或更多个基团可彼此连接并可形成环；
R9选自H、D、C1-C20的烷基、具有1～40个芳族环原子的芳族环系、或具有1～40个芳族环原子的杂芳族环系；
A是C或Si；
Y选自NR10、O、SiR11R12、S、SO2、CO或CR13R14；
R10到R14各自独立地表示经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C60芳基、或经取代或未经取代的1到30元杂芳基；或与相邻取代基连接形成经取代或未经取代的单环或多环、具体为C3-C60脂肪族环或芳香族环；并且当R10到R14上有取代基时，可被一个或多个R15取代；
R15选自氢、氘、卤素、氰基、羧基、硝基、羟基、胺基、C(＝O)R9、CF3、OCF3、Si(R9)3、N(R9)2、P(＝O)(R9)2、S(＝O)R9、S(＝O)2R9、C1-C20的直链烷基、C1-C20的直链烷氧基、C3-C20的支链烷基、C3-C20的环状烷基、C3-C20的支链烷氧基、C3-C20的环状烷氧基、C3-C20的烯基、C3-C20的炔基、具有1～40个芳族环原子的芳族环系、或具有1～40个芳族环原子的杂芳族环系；
a、b、c和d均为0～4的整数。
在上述技术方案中，优选A为C，Y为NR10、O或S，Ar1和Ar2独立地选自经取代或未经取代的有1～10个芳族环原子的芳族环系、或经取代或未经取代的具有1～10个芳族环原子的杂芳族环系，R1选自经取代或未经取代的C1-C10烷基、经取代或未经取代的C6-C30芳基、或经取代或未经取代的1到10元杂芳基；a、b、c和d均为0、1或2。
在上述技术方案中，进一步优选所述杂螺二芴类有机电致发光化合物为式1-a、1-b和1-c中的一个：
Figure BDA0002075182960000041
在上述技术方案中，再进一步优选Ar1、Ar2、R1选自以下基团中的任意一个：
Figure BDA0002075182960000051
其中，R选自氢、氘、卤素、氰基、羧基、硝基、羟基、胺基、C(＝O)R9、CF3、OCF3、Si(R9)3、N(R9)2、P(＝O)(R9)2、S(＝O)R9、S(＝O)2R9、C1-C20的直链烷基、C1-C20的直链烷氧基、C3-C20的支链烷基、C3-C20的环状烷基、C3-C20的支链烷氧基、C3-C20的环状烷氧基、C3-C20的烯基、C3-C20的炔基、具有1～40个芳族环原子的芳族环系、或具有1～40个芳族环原子的杂芳族环系；且所述—R表示在其所在苯环的任意位置，R9与前述限定一致，不再赘述。
在上述技术方案中，最优选所述杂螺二芴类有机电致发光化合物选自以下结构中的任意一个：
Figure BDA0002075182960000061
Figure BDA0002075182960000071
Figure BDA0002075182960000081
Figure BDA0002075182960000091
Figure BDA0002075182960000101
Figure BDA0002075182960000111
本发明的杂螺二芴类有机电致发光化合物可通过所属领域的技术人员已知的合成方法制备。优选本发明的一种杂螺二芴类有机电致发光化合物由下述反应流程制备：
将化合物A与化合物B反应生成化合物C，接着将化合物C与化合物D反应，制备得到化学式1所示的化合物；
其合成路线如下：
Figure BDA0002075182960000121
其中：Hal为卤素，其余取代基团与化学式1中的限定一致，这里不再赘述。
在上述技术方案中，化合物A与化合物B反应生成化合物C具体包括以下步骤：
在反应容器中将化合物B溶于四氢呋喃之后，在氮气气氛下使所述容器冷却到-78℃；接着将正丁基锂逐滴添加到混合物中；在-78℃下搅拌混合物1小时后，在室温下搅拌3小时，并且冷却到-78℃；此后，将溶解于四氢呋喃中的化合物A逐滴添加到混合物中；添加后，使反应温度升温到室温，并且搅拌混合物12小时；接着将氯化铵水溶液添加到反应溶液中以完成反应，并且用乙酸乙酯萃取反应溶液；接着使用硫酸镁干燥萃取的有机层，并且使用旋转式蒸发器去除溶剂，用管柱色谱法纯化剩余物质获得化合物C。
在上述技术方案中，化合物C与化合物D反应制备得到化学式1所示的化合物具体包括以下步骤：
将化合物C、化合物D和二氯甲烷加入反应容器中之后，用氮气充分置换空气三次；将溶解于二氯甲烷中的三氟化硼乙醚逐滴添加到混合物中；在室温下搅拌混合物3小时后，用蒸馏水淬灭，并且用二氯甲烷萃取混合物；接着使用硫酸钠干燥萃取的有机层，并且使用旋转式蒸发器去除溶剂；用柱色谱法纯化剩余物质获得化学式1所示的化合物。
本发明还提供一种含有本发明所述的杂螺二芴类有机电致发光化合物的有机电致发光装置。
在上述技术方案中，所述有机电致发光装置的空穴传输层材料为杂螺二芴类有机电致发光化合物。
本发明具有以下的有益效果：
本发明提供的杂螺二芴类有机电致发光化合物非常适用于OLED中，其特别适用于空穴传输层中。所述的杂螺二芴类有机电致发光化合物具有非常好的空穴传输性质、非常好的电子阻挡性质、以及良好的热稳定性。在用于OLED中时，其导致OLED具有长的寿命、高的量子效率和低的工作电压。
本发明提供的杂螺二芴类有机电致发光化合物的制备方法简单，产率高，适合工业化生产。
具体实施方式
实施例1：中间体制备
制备中间体C-1
Figure BDA0002075182960000131
在反应容器中加入溴苯(60mmol)和200mL四氢呋喃之后，在氮气气氛下使所述容器冷却到-78℃。接着将正丁基锂(2.5M，60mmol)缓慢逐滴添加到混合物中。在-78℃下搅拌混合物1小时后，在室温下搅拌3小时，并且冷却到-78℃。此后，将溶解于200mL四氢呋喃中的原料A-1(60mmol)缓慢逐滴添加到混合物中。添加后，使反应温度缓慢升温到室温，并且搅拌混合物12小时。接着将氯化铵水溶液添加到反应溶液中以完成反应，并且用乙酸乙酯萃取反应溶液。接着使用硫酸镁干燥萃取的有机层，并且使用旋转式蒸发器去除溶剂。用管柱色谱法纯化剩余物质获得中间体C-1(19.98g，76％，MW:438.17)。
按照中间体C-1的制备方法制备表1所示中间体。
表1实施例1反应原料以及产物结构及表征汇总。
Figure BDA0002075182960000141
Figure BDA0002075182960000151
Figure BDA0002075182960000161
实施例2目标化合物的合成
化合物H-1的合成
Figure BDA0002075182960000162
将中间体C-1(45mmol)、三苯基胺(46mmol)和500L二氯甲烷加入反应容器中之后，用氮气充分置换空气三次。将溶解于100mL二氯甲烷中的三氟化硼乙醚(46mmol)缓慢逐滴添加到混合物中。在室温下搅拌混合物3小时后，用蒸馏水淬灭，并且用二氯甲烷萃取混合物。接着使用硫酸钠干燥萃取的有机层，并且使用旋转式蒸发器去除溶剂。用柱色谱法纯化剩余物质获得化合物H-1(26.54g，90％，MW:655.39)。
表2实施例2反应原料以及产物结构及表征汇总。
Figure BDA0002075182960000171
Figure BDA0002075182960000181
Figure BDA0002075182960000191
实施例3：
由本发明的杂螺二芴类有机电致发光化合物作为空穴传输层材料用于制备绿光有机电致发光器件，具体制备方法为：
首先在ITO(阳极)上面蒸镀N1-(2-萘基)-N4,N4-二(4-(2-萘基(苯基)氨基)苯基)-N1-苯基苯-1,4-二胺("2-TNATA")60nm，紧接着蒸镀空穴传输层本发明合成的化合物H-1 60nm、主体物质4,4'-N,N'-联苯二咔唑("CBP")和掺杂物质三(2-苯基吡啶)铱("Ir(ppy)3")90:10重量比混合蒸镀30nm、蒸镀空穴阻挡层("BAlq")10nm厚度、蒸镀"Alq3"40nm厚度、蒸镀电子注入层LiF 0.2nm、蒸镀阴极Al为150nm形式制备得到有机电致发光器件。
实施例4～16：
将实施例3中的化合物H-1分别置换为化合物H-16、H-27、H-39、H-48、H-56、H-71、H-72、H-83、H-101、H-105、H-109、H-113、H-121，其他方法与实施例3相同，制备得到相应物质作为空穴传输层的有机电致发光器件。
对比例1～3
用与实施例3同样方法制备有机电致发光器件，将化合物H-1替代成比较化合物1、比较化合物2、比较化合物3，得到对应的有机电致发光器件。
Figure BDA0002075182960000201
将本发明的实施例2中的化合物制备的有机电致发光器件，对比例1-对比例3制备的有机电致发光器件加偏压(bias voltage)，用(photoresearch)公司的PR-650测试电致发光特性(EL)，5000cd/m2基准亮度下，mcscience制备的寿命装备测试T95，测定结果见表3。
表3
Figure BDA0002075182960000211
从上表可看出，由本发明提供的杂螺二芴类有机电致发光化合物作为空穴传输层制备的有机电致发光器件相对于由比较化合物作为空穴传输层制备的有机电致发光器件的发光效率及寿命有显著的提高，驱动电压显著降低。
显然，上述实施例仅仅是为清楚地说明所作的举例，而并非对实施方式的限定。对于所属领域的普通技术人员来说，在上述说明的基础上还可以做出其它不同形式的变化或变动。这里无需也无法对所有的实施方式予以穷举。而由此所引伸出的显而易见的变化或变动仍处于本发明创造的保护范围之中。

Claims (8)

1.一种杂螺二芴类有机电致发光化合物，其特征在于，其为式1-a、1-b和1-c中的一个：
Figure FDA0003321360370000011
其中：
Ar1和Ar2各自独立地表示经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C60芳基、或经取代或未经取代的1到30元杂芳基；或与相邻取代基连接形成C3-C60脂肪族环或芳香族环，其碳原子可置换为至少一个选自氮、氧和硫的杂原子；并且当Ar1、Ar2有取代基时，可被一个或多个R6取代；
R1表示经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C60芳基、或经取代或未经取代的1到30元杂芳基；或与相邻取代基连接形成C3-C60脂肪族环或芳香族环，其碳原子可置换为至少一个选自氮、氧和硫的杂原子；并且当R1上有取代基时，可被一个或多个R7取代；
R2、R3、R4和R5各自独立地表示氢、氘、卤素、氰基、羧基、硝基、羟基、胺基、经取代或未经取代的C1-C30烃基、经取代或未经取代的C1-C30烷氧基、经取代或未经取代的C3-C30环烷基、经取代或未经取代的C3-C30环烯基、经取代或未经取代的1到30元杂环烷基、经取代或未经取代的C6-C60芳基、或经取代或未经取代的1到30元杂芳基；或与相邻取代基连接形成C3-C60脂肪族环或芳香族环，其碳原子可置换成至少一个选自氮、氧和硫的杂原子；并且当R2、R3、R4和R5上有取代基时，均可被一个或多个R8取代；
R6、R7和R8各自独立地选自氢、氘、卤素、氰基、羧基、硝基、羟基、胺基、C(＝O)R9、CF3、OCF3、Si(R9)3、N(R9)2、P(＝O)(R9)2、S(＝O)R9、S(＝O)2R9、C1-C20的直链烷基、C1-C20的直链烷氧基、C3-C20的支链烷基、C3-C20的环状烷基、C3-C20的支链烷氧基、C3-C20的环状烷氧基、C3-C20的烯基、C3-C20的炔基、具有1～40个芳族环原子的芳族环系、或具有1～40个芳族环原子的杂芳族环系；其中R6、R7和R8中的两个或更多个基团可彼此连接并可形成环；
R9选自H、D、C1-C20的烷基、具有1～40个芳族环原子的芳族环系、或具有1～40个芳族环原子的杂芳族环系；
R10表示经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C60芳基、或经取代或未经取代的1到30元杂芳基；或与相邻取代基连接形成C3-C60脂肪族环或芳香族环；并且当R10上有取代基时，可被一个或多个R15取代；
R15选自氢、氘、卤素、氰基、羧基、硝基、羟基、胺基、C(＝O)R9、CF3、OCF3、Si(R9)3、N(R9)2、P(＝O)(R9)2、S(＝O)R9、S(＝O)2R9、C1-C20的直链烷基、C1-C20的直链烷氧基、C3-C20的支链烷基、C3-C20的环状烷基、C3-C20的支链烷氧基、C3-C20的环状烷氧基、C3-C20的烯基、C3-C20的炔基、具有1～40个芳族环原子的芳族环系、或具有1～40个芳族环原子的杂芳族环系；
a、b、c和d均为0～4的整数。
2.根据权利要求1所述的杂螺二芴类有机电致发光化合物，其特征在于，Ar1、Ar2、R1选自以下基团中的任意一个：
Figure FDA0003321360370000021
Figure FDA0003321360370000031
其中，R选自氢、氘、卤素、氰基、羧基、硝基、羟基、胺基、C(＝O)R9、CF3、OCF3、Si(R9)3、N(R9)2、P(＝O)(R9)2、S(＝O)R9、S(＝O)2R9、C1-C20的直链烷基、C1-C20的直链烷氧基、C3-C20的支链烷基、C3-C20的环状烷基、C3-C20的支链烷氧基、C3-C20的环状烷氧基、C3-C20的烯基、C3-C20的炔基、具有1～40个芳族环原子的芳族环系、或具有1～40个芳族环原子的杂芳族环系。
3.一种杂螺二芴类有机电致发光化合物，其特征在于，其选自以下结构中的任意一个：
Figure FDA0003321360370000041
Figure FDA0003321360370000051
Figure FDA0003321360370000061
Figure FDA0003321360370000071
Figure FDA0003321360370000081
Figure FDA0003321360370000091
4.一种权利要求1-3任意一项所述的杂螺二芴类有机电致发光化合物的制备方法，其特征在于，包括以下步骤：
将化合物A与化合物B反应生成化合物C，接着将化合物C与化合物D反应，制备得到化学式1所示的化合物；
其合成路线如下：
Figure FDA0003321360370000101
其中：Hal为卤素；
其中化学式1具体为式1-a、1-b和1-c中的一个或H-1～H-123中的一个。
5.根据权利要求4所述的杂螺二芴类有机电致发光化合物的制备方法，其特征在于，化合物A与化合物B反应生成化合物C具体包括以下步骤：
在反应容器中将化合物B溶于四氢呋喃之后，在氮气气氛下使所述容器冷却到-78℃；接着将正丁基锂逐滴添加到混合物中；在-78℃下搅拌混合物1小时后，在室温下搅拌3小时，并且冷却到-78℃；此后，将溶解于四氢呋喃中的化合物A逐滴添加到混合物中；添加后，使反应温度升温到室温，并且搅拌混合物12小时；接着将氯化铵水溶液添加到反应溶液中以完成反应，并且用乙酸乙酯萃取反应溶液；接着使用硫酸镁干燥萃取的有机层，并且使用旋转式蒸发器去除溶剂，用管柱色谱法纯化剩余物质获得化合物C。
6.根据权利要求4所述的杂螺二芴类有机电致发光化合物的制备方法，其特征在于，化合物C与化合物D反应制备得到化学式1所示的化合物具体包括以下步骤：
将化合物C、化合物D和二氯甲烷加入反应容器中之后，用氮气充分置换空气三次；将溶解于二氯甲烷中的三氟化硼乙醚逐滴添加到混合物中；在室温下搅拌混合物3小时后，用蒸馏水淬灭，并且用二氯甲烷萃取混合物；接着使用硫酸钠干燥萃取的有机层，并且使用旋转式蒸发器去除溶剂；用柱色谱法纯化剩余物质获得化学式1所示的化合物。
7.一种含有权利要求1-3任意一项所述的杂螺二芴类有机电致发光化合物的有机电致发光装置。
8.根据权利要求7所述的有机电致发光装置，其特征在于，所述有机电致发光装置的空穴传输层材料为杂螺二芴类有机电致发光化合物。
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