CN110373183A - 有机电致发光化合物和包含该化合物的有机电致发光装置 - Google Patents

有机电致发光化合物和包含该化合物的有机电致发光装置 Download PDF

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CN110373183A
CN110373183A CN201910619458.8A CN201910619458A CN110373183A CN 110373183 A CN110373183 A CN 110373183A CN 201910619458 A CN201910619458 A CN 201910619458A CN 110373183 A CN110373183 A CN 110373183A
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organic electroluminescent
electroluminescent compounds
aryl
aromatic ring
organic
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马晓宇
金成寿
金虎勇
金成国
王进政
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Jilin Optical and Electronic Materials Co Ltd
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

本发明涉及一种有机电致发光化合物和包含该化合物的有机电致发光装置，所述有机电致发光化合物结构式如化学式1所示：

Description

有机电致发光化合物和包含该化合物的有机电致发光装置
技术领域
本发明涉及有机发光化合物技术领域，具体涉及一种具有极佳电流效率以及长寿命的有机电致发光化合物和包含该化合物的有机电致发光装置。
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。
有机EL元件是利用了如下原理的自发光元件：通过施加电场，利用由阳极注入的空穴与由阴极注入的电子的复合能使荧光性物质发光。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)。
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。
决定有机EL装置中的发光效率的最重要因素是发光材料。到目前为止，荧光材料已经广泛用作发光材料。然而，鉴于电致发光机制，由于磷光材料在理论上与荧光材料相比使发光效率增强四(4)倍，因此磷光发光材料的开发得到广泛研究。铱(III)络合物已广泛地被称为磷光掺杂材料。目前，4,4′-N,N′-二咔唑-联苯(CBP)、9,10-二(2-萘基)蒽(ADN)等作为已知的磷光主体材料得到广泛的应用。尽管这些材料提供良好发光特征，但其具有以下缺点：(1)由于其较低玻璃态转变温度和不良热稳定性，导致装置的寿命降低。(2)包含磷光主体材料的有机EL装置需要较高的驱动电压。同时，为了提高有机EL装置的效率和稳定性，需要其具有包含空穴注入层、空穴传输层、发光层、电子传输层和电子注入层的多层结构。其中空穴传输层可改变空穴到发光层的空穴传输效率、发光效率、寿命等。因此，使用铜酞菁(CuPc)、4，4′-双[N-(1-萘基)-N-苯基氨基]联苯(NPB)、N，N′-二苯基-N，N′-双(3-甲基苯基)-(1，1′-联苯)-4，4′-二胺(TPD)等作为空穴传输材料。然而，使用这些材料的有机EL装置在量子效率和使用寿命方面有问题。
发明内容
本发明要解决现有空穴传输材料制备的有机EL装置在量子效率和使用寿命不高的技术问题，提供一种具有极佳电流效率以及长寿命的有机电致发光化合物和包含该化合物的有机电致发光装置。
为了解决上述技术问题，本发明的技术方案具体如下：
本发明提供一种有机电致发光化合物，其结构式如化学式1所示：
其中：
L为连接集团，表示C6-C60芳基或C3-C30杂芳基；进一步优选为C6-C30芳基或C5-C10杂芳基；再进一步优选为被一个或多个基团R3取代的苯、联苯、萘、蒽、菲、芘、芴、吡啶、咪唑或喹啉；
Ar1表示经取代或未经取代的C1-C30脂肪烃、经取代或未经取代的C6-C60芳基或经取代或未经取代的C3-C30杂芳基，或与相邻取代基连接形成单环或多环C3-C60脂环族环或C6-C60芳香族环；进一步优选为经取代或未经取代的C6-C30芳基、经取代或未经取代的C5-C10杂芳基、或与相邻取代基连接形成单环或多环C6-C30芳香族环；再进一步优选为被一个或多个基团R3取代的苯、萘、菲、芴、螺二芴、二苯并呋喃、二苯并噻吩，二苯并咔唑、吡啶、菲啶、喹喔啉、喹唑啉、嘧啶或哒嗪；
环A表示C3-C30环烷基、C3-C30环烯基、C6-C60杂环烷基、C6-C60芳基、或C6-C60杂芳基；
R、R1、R2为相同或不同的取代基，各自独立地选自H、D、卤素、CN、硝基、羧基、羰基、氨基或Si(R3)3；
或者各自独立地选自C1-C40直链烷基、C1-C40烷氧基、C3-C40支链或环状的烷基、或C3-C40支链或环状的烷氧基；前述取代基团可以被一个或多个基团R3取代，其中一个或多个H原子可以被D或F代替；
或者各自独立地选自C6-C60芳基、或C6-C60杂芳基；
或与相邻取代基连接形成单环或多环C6-C30芳香族环或C3-C30脂肪族环；
优选R、R1、R2各自独立地选自被一个或多个基团R3取代的苯、萘、菲、芴、螺二芴、二苯并呋喃或二苯并噻吩；
其中R3相同或不同，选自H、D、F、Cl、Br、I或者Si(R4)3；
或者选自C1-C40直链烷基、C1-C40烷氧基、C1-C40硫代烷基、C3-C40支链烷基、C3-C40环状烷基、C3-C40烷氧基、或C3-C40硫代烷基基团；前述取代基团可以被一个或多个基团R3取代，其中一个或多个非相邻的CH2基团可以被Si(R4)2、C＝NR4、P(＝O)(R4)、SO、SO2、NR4、O、S或CONR4代替，并且其中一个或多个H原子可以被D、F、Cl、Br或I代替；
或者选自C6-C60芳基、具有C5-C60芳族环原子的芳烷基、或具有C5-C60芳族环原子的芳氧基；所述芳基选自苯、萘、菲、芴、螺二芴或者这些基团中的两个、三个、四个或五个的组合，其在每种情况下可以是相同的或不同的，其在每种情况下可以被一个或多个基团R4取代；所述芳氧基基团可以被一个或多个基团R4取代；所述芳烷基基团可以被一个或多个基团R4取代，其中两个或更多个相邻的取代基R2可以任选形成单环或多环的脂族环系，其可以被一个或多个基团R4取代；
R4选自H、D、F、C1-C20的脂族烃基、C6-C30的芳基、或者两个或更多个相邻的取代基R4可以彼此形成单环或多环的脂族环系或芳香族环系；其中脂族烃基或芳基中的一个或多个H原子可以被D或F代替；
n为0到4的整数；优选n为1或2；
m是0、1、2或3。
在上述技术方案中，优选当Ar1与相邻取代基连接形成单环或多环C3-C60脂环族环或C6-C60芳香族环时，其碳原子置换为至少一个选自氮、氧和硫的杂原子；当R、R1、R2分别相邻取代基连接形成单环或多环C6-C30芳香族环和C3-C30脂肪族环，其碳原子置换为至少一个选自氮、氧和硫的杂原子。
在上述技术方案中，优选Ar1选自以下结构中的一种：
其中，R3与上述限定范围相同；且所述—R3表示在其所在环的任意位置，其中*为连接位置。
在上述技术方案中，最优选所述有机电致发光化合物选自以下结构中的任意一个：
本发明还提供一种含有本发明化学式1所示的化合物的有机电致发光器件。
在上述技术方案中，优选所述有机电致发光器件包括：
第一电极、第二电极和置于所述两电极之间的有机物层，其中，所述有机物层中包含有本发明化学式1所示的化合物；化学式1所示的化合物是单一形态或与其它物质混合存在于有机物层中。
在上述技术方案中，优选本发明化学式1所示的有机电致发光化合物作为空穴传输层材料。
其中，所述有机物层至少包括空穴注入层、空穴传输层、既具备空穴注入又具备空穴传输技能层，电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层和既具备电子传输又具备电子注入技能层中的一种或几种。
本发明中“有机物层”指的是有机电致发光器件第一电极和第二电极之间部署的全部层的术语。
当化学式1所示结构的化合物存在于所述有机物层中的发光层时，化学式1所示结构的化合物可以作为发光主体或者掺杂在其它荧光主体中；
当化学式1所示结构的化合物存在于所述有机物层中的空穴传输层或者空穴注入层时，化学式1所示结构的化合物可以作为空穴传输层、空穴注入层以及既具备空穴注入又具备空穴传输功能层。
本发明所提供的器件可以用于有机发光器件(OLED)、有机太阳电池(OSC)、电子纸(e-Paper)、有机感光体(OPC)或有机薄膜晶体管(OTFT)。
本发明所述的器件可以通过薄膜蒸镀、电子束蒸发、物理气相沉积等方法在基板上蒸镀金属以及具有导电性的氧化物及他们的合金形成阳极，也可以采用旋转涂膜(spin-coating)或薄带带头蒸镀；还可以采用成型(tape-casting)、刮片法(doctor-blading)、丝网印刷(Screen-Printing)、喷墨印刷或热成像(Thermal-Imaging)等方法减少层数制造。
本发明的有益效果是：
本发明提供了一种新型结构的有机电致发光化合物，其具有适合的玻璃态转变温度，使用该化合物制备的有机电致发光器件的发光效率及寿命相对于NPD有显著的提高。
具体实施方式
下文中，将对本发明进行详细描述。然而，以下描述旨在解释本发明，并且不打算以任何方式限制本发明的范围。
本发明涉及化学式1的有机电致发光化合物、包含所述化合物的有机电致发光器件。
本发明的特定化合物包括以下化合物，但不限于此：
合成实施例1
反应过程：将原料A-21[2-氨基联苯(16.93g，100mmol)]、叔丁醇钠(19.23g，200mmol)加入到500mL甲苯中。使用氮气置换空气三次，加入B-21[(9,9-二甲基-2-溴芴27.32g，100mmol)]、三(二亚苄基丙酮)二钯(1.1g，1mmol)，三叔丁基膦(1.62g，8mmol)再次用氮气置换空气三次，在氮气保护下加热到100℃。
处理过程：TLC监测。待反应结束后，在氮气保护下冷却至室温。使用分液漏斗进行分液，保留有机相。使用硅藻土除去催化剂，用DCM洗硅藻土至无产品。浓缩滤液至少量，硅胶拌样，使用硅胶漏斗进行分离得到中间体C-21(30.73g，收率85％)。
按照上述方法制备得到表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
合成实施例2
反应过程：将中间体C-21(28.9g，80mmol)、叔丁醇钠(23.04g，240mmol)加入到500mL甲苯中。使用氮气置换空气三次，加入原料D-21(36.25g，80mmol)、Pd2(dba)3(0.73g，0.8mmol)，三叔丁基膦(0.32g，1.6mmol)再次用氮气置换空气三次，在氮气保护下加热到100℃。
处理过程：TLC监测。待反应结束后，在氮气保护下冷却至室温。使用分液漏斗进行分液，保留有机相。使用硅藻土除去催化剂，用THF洗硅藻土至无产品。浓缩滤液至少量，硅胶拌样，使用硅胶漏斗进行分离得化合物21(46.68g，收率75％)。
表2实施例2反应原料以及产物结构及表征汇总
器件实施例1：制造含有化合物21的有机电致发光器件
将涂层厚度为的ITO玻璃基板放在蒸馏水中清洗2次，超声波洗涤30分钟，用蒸馏水反复清洗2次，超声波洗涤10分钟，蒸馏水清洗结束后，异丙醇、丙酮、甲醇等溶剂按顺序超声波洗涤以后干燥，转移到等离子体清洗机里，将上述基板洗涤5分钟，送到蒸镀机里。将已经准备好的ITO透明电极上蒸镀厚度为50nm的4,4',4”-三[2-萘基苯基氨基]三苯基胺(2-TNATA)作为空穴注入层。然后将化合物21在形成的空穴注入层上面真空蒸镀厚度为30nm的空穴传输层。然后在上述空穴传输层上蒸镀厚度为30nm的蓝色主体材料9，10-二(2-萘基)蒽(ADN)和掺杂材料双(4,6-二氟苯基吡啶-N,C2)吡啶甲酰合铱(FIrpic)。主体材料和掺杂材料的重量比为95:5。接着在上述发光层上真空蒸镀厚度为40nm的TPBi作为空穴阻挡层及电子传输层。在上述电子传输层上真空蒸镀厚度为0.5nm氟化锂(LiF)，作为电子注入层。最后蒸镀厚度为150nm的铝作为阴极，以此完成了有机电致发光器件的制备。对得到的器件的性能发光特性测试，测量采用KEITHLEY 2400型源测量单元，CS-2000分光辐射亮度计，以评价驱动电压，发光亮度，发光效率。
器件实施例2～器件实施例10：
器件实施例1中的化合物21分别置换为化合物41、66、67、68、75、76、77、78、80，其他方法相同，制作含有相应化合物的有机电致发光器件。
器件对照例1：器件实施例1中的化合物21置换为NPD，制作器件对照例1。
用热重分析法测量上述实施例合成的化合物的热分解温度Td。应用差示扫描量热法测量上述化合物的玻璃化转变温度Tg。结果如表3所示
表3
化合物 Td(℃) Tg(℃)
21 535 140
41 520 131
66 530 137
67 500 130
68 515 133
75 525 135
76 530 138
77 550 145
78 541 139
80 520 135
表4为本发明实施例制备的化合物以及NPD制备的发光器件的发光特性测试结果。
表4
从上表3和4可看出，本发明提供的化合物有适合的玻璃态转变温度，由本发明的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相对于由NPD作为空穴传输层制备的有机电致发光器件有显著的提高。
以上实施例的说明只是用于帮助理解本发明的方法及其核心思想。应当指出，对于本技术领域的普通技术人员来说，在不脱离本发明原理的前提下，还可以对本发明进行若干改进和修饰，这些改进和修饰也落入本发明权利要求的保护范围内。

Claims (10)

1.一种有机电致发光化合物，其特征在于，其结构式如化学式1所示：
其中：
L为连接集团，表示C6-C60芳基或C3-C30杂芳基；
Ar1表示经取代或未经取代的C1-C30脂肪烃、经取代或未经取代的C6-C60芳基、或经取代或未经取代的C3-C30杂芳基，或与相邻取代基连接形成单环或多环C3-C60脂环族环或C6-C60芳香族环；
环A表示C3-C30环烷基、C3-C30环烯基、C6-C60杂环烷基、C6-C60芳基、或C6-C60杂芳基；
R、R1、R2为相同或不同的取代基，各自独立地选自H、D、卤素、CN、硝基、羧基、羰基、氨基或Si(R3)3；
或者各自独立地选自C1-C40直链烷基、C1-C40烷氧基、C3-C40支链或环状的烷基、或C3-C40支链或环状的烷氧基；
或者各自独立地选自C6-C60芳基、或C6-C60杂芳基；
或与相邻取代基连接形成单环或多环C6-C30芳香族环或C3-C30脂肪族环；
其中Si(R3)3取代基中的R3相同或不同，选自H、D、F、Cl、Br、I、Si(R4)3、C1-C40直链烷基、C1-C40烷氧基、C1-C40硫代烷基、C3-C40支链烷基、C3-C40环状烷基、C3-C40烷氧基、C3-C40硫代烷基基团、C6-C60芳基、具有C5-C60芳族环原子的芳烷基、或具有C5-C60芳族环原子的芳氧基；
R4选自H、D、F、C1-C20的脂族烃基、C6-C30的芳基、或者两个或更多个相邻的取代基R4彼此形成单环或多环的脂族环系或芳香族环系；
n为0到4的整数；
m是0、1、2或3。
2.根据权利要求1所述的有机电致发光化合物，其特征在于，L选自被一个或多个基团R3取代的苯、联苯、萘、蒽、菲、芘、芴、吡啶、咪唑或喹啉。
3.根据权利要求1所述的有机电致发光化合物，其特征在于，当Ar1与相邻取代基连接形成单环或多环C3-C60脂环族环或C6-C60芳香族环时，其碳原子置换为至少一个选自氮、氧和硫的杂原子；当R、R1、R2分别相邻取代基连接形成单环或多环C6-C30芳香族环或C3-C30脂肪族环，其碳原子置换为至少一个选自氮、氧和硫的杂原子。
4.根据权利要求3所述的有机电致发光化合物，其特征在于，Ar1为经取代或未经取代的C6-C30芳基、经取代或未经取代的C5-C10杂芳基、或与相邻取代基连接形成单环或多环C6-C30芳香族环。
5.根据权利要求4所述的有机电致发光化合物，其特征在于，Ar1为被一个或多个基团R3取代的苯、萘、菲、芴、螺二芴、二苯并呋喃、二苯并噻吩、二苯并咔唑、吡啶、菲啶、喹喔啉、喹唑啉、嘧啶或哒嗪。
6.根据权利要求3所述的有机电致发光化合物，其特征在于，R、R1、R2各自独立地选自被一个或多个基团R3取代的苯、萘、菲、芴、螺二芴、二苯并呋喃或二苯并噻吩。
7.根据权利要求1所述的有机电致发光化合物，其特征在于，Ar1选自以下结构中的一种：
8.根据权利要求1所述的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：
9.一种含有权利要求1-8任意一项所述的有机电致发光化合物的有机电致发光器件。
10.根据权利要求9所述的有机电致发光器件，权利要求1-8任意一项所述的有机电致发光化合物作为空穴传输层材料。
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