CN111655683A - 新的杂环化合物和包含其的有机发光器件 - Google Patents
新的杂环化合物和包含其的有机发光器件 Download PDFInfo
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- CN111655683A CN111655683A CN201980009436.8A CN201980009436A CN111655683A CN 111655683 A CN111655683 A CN 111655683A CN 201980009436 A CN201980009436 A CN 201980009436A CN 111655683 A CN111655683 A CN 111655683A
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- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明提供了新的杂环化合物和包含其的有机发光器件。
Description
技术领域
相关申请的交叉引用
本申请要求于2018年4月24日向韩国知识产权局提交的韩国专利申请第10-2018-0047306号和于2019年4月23日向韩国知识产权局提交的韩国专利申请第10-2019-0047557号的申请日的权益,其全部内容通过引用并入本文。
本发明涉及新的杂环化合物和包含其的有机发光器件。
背景技术
通常,有机发光现象是指通过使用有机材料将电能转换成光能的现象。利用有机发光现象的有机发光器件具有以下特性:例如,宽视角,优异的对比度,快速的响应时间,以及优异的亮度、驱动电压和响应速度,并因此已经对其进行了许多研究。
有机发光器件通常具有包括阳极、阴极和插入阳极与阴极之间的有机材料层的结构。为了提高有机发光器件的效率和稳定性,有机材料层常常具有包含不同材料的多层结构,并且例如,有机材料层可以由空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等形成。在有机发光器件的结构中,如果在两个电极之间施加电压,则空穴从阳极注入有机材料层并且电子从阴极注入有机材料层,当注入的空穴和电子彼此相遇时,形成激子,并且当激子落至基态时发光。
持续需要开发这些有机发光器件中使用的有机材料用新材料。
现有技术文献
专利文献
(专利文献0001)韩国专利特许公开第10-2000-0051826号
发明内容
技术问题
本发明的目的是提供新的杂环化合物和包含其的有机发光器件。
技术方案
在本发明的一个方面中,提供了由以下化学式1表示的化合物:
[化学式1]
其中,在化学式1中,
Y1为O或S,
Ar1为经取代的C6-60芳基;或者经取代或未经取代的包含选自O、N、Si和S中的一个或更多个杂原子的C1-60杂芳基,
L为单键;经取代或未经取代的C6-60亚芳基;或者经取代或未经取代的包含选自O、N、Si和S中的一个或更多个杂原子的C1-60亚杂芳基,
R1至R5各自独立地为氢;氘;卤素;氰基;硝基;氨基;经取代或未经取代的C1-60烷基;经取代或未经取代的C1-60卤代烷基;经取代或未经取代的C1-60烷氧基;经取代或未经取代的C1-60卤代烷氧基;经取代或未经取代的C3-60环烷基;经取代或未经取代的C2-60烯基;经取代或未经取代的C6-60芳基;经取代或未经取代的C6-60芳氧基;或者经取代或未经取代的包含选自N、O和S中的一个或更多个杂原子的C1-60杂芳基,以及
n1至n3各自独立地为1至5的整数。
在本发明的另一个方面中,提供了有机发光器件,其包括:第一电极;与第一电极相对设置的第二电极;以及设置在第一电极与第二电极之间的一个或更多个有机材料层,其中所述有机材料层的一个或更多个层包含由化学式1表示的化合物。
有益效果
上述由化学式1表示的化合物可以用作有机发光器件的有机材料层的材料,并且可以在有机发光器件中改善效率,实现低驱动电压,和/或改善寿命特性。
附图说明
图1示出了包括基底1、阳极2、发光层3和阴极4的有机发光器件的一个实例。
图2示出了包括基底1、阳极2、空穴注入层5、空穴传输层6、电子阻挡层7、发光层3、电子传输层8、电子注入层9和阴极4的有机发光器件的一个实例。
具体实施方式
在下文中,将更详细地描述本发明以帮助理解本发明。
在本发明的一个实施方案中,提供了由化学式1表示的化合物。
如本文所使用的,术语“经取代或未经取代的”意指未经取代或经选自以下的一个或更多个取代基取代:氘;卤素基团;氰基;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;和包含N、O和S原子中的至少一者的杂芳基,或者未经取代或经以上例示的取代基中的两个或更多个取代基相连接的取代基取代。例如,当“两个或更多个取代基相连接的取代基”为联苯基时,联苯基可以被解释为经一个苯基取代的芳基、或两个苯基相连接的取代基。
在本说明书中,羰基的碳原子数没有特别限制,但优选为1至40。具体地,羰基可以为具有以下结构式的化合物,但不限于此。
在本说明书中,酯基可以具有其中酯基的氧可以被具有1至25个碳原子的直链、支链或环状烷基或者具有6至25个碳原子的芳基取代的结构。具体地,酯基可以为具有以下结构式的化合物,但不限于此。
在本说明书中,酰亚胺基的碳原子数没有特别限制,但优选为1至25。具体地,酰亚胺基可以为具有以下结构式的化合物,但不限于此。
在本说明书中,甲硅烷基具体地包括三甲基甲硅烷基、三乙基甲硅烷基、叔丁基二甲基甲硅烷基、乙烯基二甲基甲硅烷基、丙基二甲基甲硅烷基、三苯基甲硅烷基、二苯基甲硅烷基、苯基甲硅烷基等,但不限于此。
在本说明书中,硼基具体地包括三甲基硼基、三乙基硼基、叔丁基二甲基硼基、三苯基硼基、和苯基硼基,但不限于此。
在本说明书中,卤素基团的实例包括氟、氯、溴和碘。
在本说明书中,烷基可以为直链或支链的,并且其碳原子数没有特别限制,但优选为1至40。根据一个实施方案,烷基的碳原子数为1至20。根据另一个实施方案,烷基的碳原子数为1至10。根据另一个实施方案,烷基的碳原子数为1至6。烷基的具体实例包括甲基、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、2-甲基戊基、4-甲基己基、5-甲基己基等,但不限于此。
在本说明书中,烯基可以为直链或支链的,并且其碳原子数没有特别限制,但优选为2至40。根据一个实施方案,烯基的碳原子数为2至20。根据另一个实施方案,烯基的碳原子数为2至10。根据又一个实施方案,烯基的碳原子数为2至6。其具体实例包括乙烯基、1-丙烯基、异丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-戊烯基、2-戊烯基、3-戊烯基、3-甲基-1-丁烯基、1,3-丁二烯基、烯丙基、1-苯基乙烯基-1-基、2-苯基乙烯基-1-基、2,2-二苯基乙烯基-1-基、2-苯基-2-(萘基-1-基)乙烯基-1-基、2,2-双(二苯基-1-基)乙烯基-1-基、茋基、苯乙烯基等,但不限于此。
在本说明书中,环烷基没有特别限制,但其碳原子数优选为3至60。根据一个实施方案,环烷基的碳原子数为3至30。根据另一个实施方案,环烷基的碳原子数为3至20。根据又一个实施方案,环烷基的碳原子数为3至6。其具体实例包括环丙基、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,但不限于此。
在本说明书中,芳基没有特别限制,但优选具有6至60个碳原子,并且可以为单环芳基或多环芳基。根据一个实施方案,芳基的碳原子数为6至30。根据一个实施方案,芳基的碳原子数为6至20。作为单环芳基,芳基可以为苯基、联苯基、三联苯基等,但不限于此。多环芳基的实例包括萘基、蒽基、菲基、芘基、苝基、基等,但不限于此。
在本说明书中,杂芳基为包含O、N、Si和S中的一者或更多者作为杂原子的杂芳基,并且其碳原子数没有特别限制,但优选为2至60。杂芳基的实例包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、唑基、二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、苯并呋喃基、菲咯啉基、异唑基、噻二唑基、吩噻嗪基、二苯并呋喃基等,但不限于此。
在本说明书中,芳烷基、芳烯基、烷基芳基和芳基胺基中的芳基与上述芳基的实例相同。在本说明书中,芳烷基、烷基芳基和烷基胺基中的烷基与上述烷基的实例相同。在本说明书中,杂芳基胺中的杂芳基可以适用于上述杂芳基的描述。在本说明书中,芳烯基中的烯基与上述烯基的实例相同。在本说明书中,可以适用上述芳基的描述,不同之处在于亚芳基是二价基团。在本说明书中,可以适用上述杂芳基的描述,不同之处在于亚杂芳基是二价基团。在本说明书中,可以适用上述芳基或环烷基的描述,不同之处在于烃环不是一价基团而是通过两个取代基结合形成的。在本说明书中,可以适用上述杂芳基的描述,不同之处在于杂环不是一价基团而是通过两个取代基结合形成的。
同时,在化学式1中,Ar1可以为选自以下的任一者:
其中,
X1至X3各自独立地为N或CR’3,条件是X1至X3中的至少两者为N,
Y2和Y3各自独立地为O、S或NR’,
Ar2至Ar5各自独立地为经取代或未经取代的C6-60芳基;或者经取代或未经取代的包含选自O、N、Si和S中的一个或更多个杂原子的C1-60杂芳基,
每个R’独立地为氢;氘;卤素;氰基;硝基;氨基;经取代或未经取代的C1-60烷基;经取代或未经取代的C1-60卤代烷基;经取代或未经取代的C1-60烷氧基;经取代或未经取代的C1-60卤代烷氧基;经取代或未经取代的C3-60环烷基;经取代或未经取代的C2-60烯基;经取代或未经取代的C6-60芳基;经取代或未经取代的C6-60芳氧基;或者经取代或未经取代的包含选自N、O和S中的一个或更多个杂原子的C1-60杂芳基,以及
n4至n11可以各自独立地为1至5的整数。
优选地,Ar1可以为选自以下的任一者:
其中,
Ar2和Ar5如以上所限定。
优选地,在化学式1中,L可以为单键、或选自以下的任一者:
优选地,在化学式1中,R1至R3可以各自独立地为氢;氘;氰基;或者经取代或未经取代的C1-10烷基。
例如,R1至R3可以为氢。
例如,上述化合物可以选自以下化合物:
同时,由化学式1表示的化合物可以例如根据以下反应方案1中所示的制备方法来制备。
[反应方案1]
在反应方案1中,Y1、Ar1、L、R1至R3、和n1至n3与化学式1中所限定的相同。
上述反应为Suzuki偶联反应,其优选在钯催化剂和碱的存在下进行,并且可以如本领域已知的那样对用于Suzuki偶联反应的反应性基团进行改变。以上制备方法可以在下文所述的制备例中进一步说明。
在本发明的另一个实施方案中,提供了包含由上述化学式1表示的化合物的有机发光器件。作为实例,提供了这样的有机发光器件,其包括:第一电极;与第一电极相对设置的第二电极;以及设置在第一电极与第二电极之间的一个或更多个有机材料层,其中有机材料层中的一个或更多个层包含由化学式1表示的化合物。
本发明的有机发光器件的有机材料层可以具有单层结构,或者其可以具有其中堆叠有两个或更多个有机材料层的多层结构。例如,本公开内容的有机发光器件可以具有包括空穴注入层、空穴传输层、电子阻挡层、发光层、电子传输层、电子注入层等作为有机材料层的结构。然而,有机发光器件的结构不限于此,并且其可以包括更少数量的有机层。
具体地,有机材料层可以包括发光层,其中发光层可以包含由化学式1表示的化合物。
在这种情况下,由化学式1表示的化合物可以用作发光层中的主体。
此外,发光层可以包含两种或更多种主体。此外,以上主体的一者可以为由化学式1表示的化合物。
此外,根据本发明的有机发光器件可以为其中阳极、一个或更多个有机材料层和阴极顺序地堆叠在基底上的正常型有机发光器件。此外,根据本公开内容的有机发光器件可以为其中阴极、一个或更多个有机材料层和阳极顺序地堆叠在基底上的倒置型有机发光器件。例如,图1和图2中示出了根据本公开内容的一个实施方案的有机发光器件的结构。
图1示出了包括基底1、阳极2、发光层3和阴极4的有机发光器件的一个实例。在这样的结构中,由化学式1表示的化合物可以包含在发光层中。
图2示出了包括基底1、阳极2、空穴注入层5、空穴传输层6、电子阻挡层7、发光层3、电子传输层8、电子注入层9和阴极4的有机发光器件的一个实例。在这样的结构中,由化学式1表示的化合物可以包含在空穴注入层、空穴传输层、发光层和电子传输层中的一个或更多个层中。
根据本发明的有机发光器件可以通过本领域已知的材料和方法来制造,不同之处在于有机材料层的一个或更多个层包含由化学式1表示的化合物。此外,当有机发光器件包括复数个有机材料层时,有机材料层可以由相同材料或不同材料形成。
例如,根据本发明的有机发光器件可以通过在基底上顺序地堆叠第一电极、有机材料层和第二电极来制造。在这种情况下,有机发光器件可以通过如下来制造:通过使用PVD(物理气相沉积)法(例如溅射法或电子束蒸镀法)在基底上沉积金属、具有导电性的金属氧化物、或其合金以形成阳极,在阳极上形成包括空穴注入层、空穴传输层、发光层和电子传输层的有机材料层,然后在有机材料层上沉积可以用作阴极的材料。除了这样的方法之外,有机发光器件可以通过在基底上顺序地沉积阴极材料、有机材料层和阳极材料来制造。
此外,在制造有机发光器件时,由化学式1表示的化合物可以通过溶液涂覆法以及真空沉积法形成为有机层。在本文中,溶液涂覆法意指旋涂、浸涂、刮涂、喷墨印刷、丝网印刷、喷洒、辊涂等,但不限于此。
除了这样的方法之外,有机发光器件可以通过在基底上顺序地沉积阴极材料、有机材料层和阳极材料来制造(国际公开WO 2003/012890)。然而,制造方法不限于此。
作为实例,第一电极为阳极,并且第二电极为阴极,或者可选地,第一电极为阴极,并且第二电极为阳极。
作为阳极材料,通常,优选使用具有大功函数的材料使得空穴可以顺利地注入有机材料层。阳极材料的具体实例包括:金属,例如钒、铬、铜、锌、和金、或其合金;金属氧化物,例如锌氧化物、铟氧化物、铟锡氧化物(ITO)、和铟锌氧化物(IZO);金属和氧化物的组合,例如ZnO:Al或SnO2:Sb;导电聚合物,例如聚(3-甲基噻吩)、聚[3,4-(乙烯-1,2-二氧基)噻吩](PEDOT)、聚吡咯、聚苯胺等,但不限于此。
作为阴极材料,通常,优选使用具有小功函数的材料以使电子可以容易地注入有机材料层。阴极材料的具体实例包括:金属,例如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅,或其合金;多层结构材料,例如LiF/Al、或LiO2/Al等,但不限于此。
空穴注入层是用于注入来自电极的空穴的层,并且空穴注入材料优选为这样的化合物:其具有传输空穴的能力,因此具有在阳极中的空穴注入效应以及对于发光层或发光材料的优异的空穴注入效应,防止发光层中产生的激子移动至空穴注入层或电子注入材料,并且形成薄膜的能力优异。优选空穴注入材料的HOMO(最高占据分子轨道)在阳极材料的功函数与周围有机材料层的HOMO之间。空穴注入材料的具体实例包括金属卟啉、低聚噻吩、基于芳基胺的有机材料、基于六腈六氮杂苯并菲的有机材料、基于喹吖啶酮的有机材料、基于苝的有机材料、蒽醌、基于聚苯胺和基于聚噻吩的导电聚合物等,但不限于此。
空穴传输层是接收来自空穴注入层的空穴并将空穴传输至发光层的层,并且其适当地为对空穴具有大迁移率的材料,并且可以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。其具体实例包括基于芳基胺的有机材料、导电聚合物、同时存在共轭部分和非共轭部分的嵌段共聚物等,但不限于此。
发光材料优选为这样的材料:其可以接收分别从空穴传输层和电子传输层传输的空穴和电子,并且使空穴和电子结合以发出可见光区域内的光,并且对荧光或磷光具有良好的量子效率。发光材料的具体实例包括:8-羟基-喹啉铝配合物(Alq3);基于咔唑的化合物;二聚苯乙烯基化合物;BAlq;10-羟基苯并喹啉-金属化合物;基于苯并唑、基于苯并噻唑和基于苯并咪唑的化合物;基于聚(对亚苯基亚乙烯基)(PPV)的聚合物;螺环化合物;聚芴;红荧烯等,但不限于此。发光层可以包含主体材料和掺杂剂材料。
主体材料可以为稠合芳族环衍生物、含杂环的化合物等。稠合芳族环衍生物的具体实例包括蒽衍生物、芘衍生物、萘衍生物、并五苯衍生物、菲化合物、荧蒽化合物等。含杂环的化合物的实例包括咔唑衍生物、二苯并呋喃衍生物、梯子型呋喃化合物、嘧啶衍生物等,但不限于此。
掺杂剂材料的实例包括芳族胺衍生物、苯乙烯胺化合物、硼配合物、荧蒽化合物、金属配合物等。具体地,芳族胺衍生物为经取代或未经取代的具有芳基氨基的稠合芳族环衍生物,并且其实例包括具有芳基氨基的芘、蒽、二茚并芘(periflanthene)等。苯乙烯胺化合物是其中经取代或未经取代的芳基胺中取代有至少一个芳基乙烯基的化合物,其中选自芳基、甲硅烷基、烷基、环烷基和芳基氨基中的一个或两个或更多个取代基是经取代或未经取代的。其具体实例包括苯乙烯胺、苯乙烯二胺、苯乙烯三胺、苯乙烯四胺等,但不限于此。此外,金属配合物包括铱配合物、铂配合物等,但不限于此。
电子传输层是接收来自电子注入层的电子并将电子传输至发光层的层,并且电子传输材料适当地为可以很好地接收来自阴极的电子并将电子传输至发光层以及对电子具有大迁移率的材料。电子传输材料的具体实例包括:8-羟基喹啉的Al配合物;包含Alq3的配合物;有机自由基化合物;羟基黄酮-金属配合物等,但不限于此。电子传输层可以与如根据相关技术所使用的任何期望的阴极材料一起使用。特别地,合适的阴极材料的实例为后接铝层或银层的具有低功函数的典型材料。其具体实例包括铯、钡、钙、镱、和钐,在每种情况下后接铝层或银层。
电子注入层是注入来自电极的电子的层,并且优选这样的化合物:其具有传输电子的能力、具有注入来自阴极的电子的效应以及将电子注入到发光层或发光材料中的优异效应,防止由发光层产生的激子移动至空穴注入层,并且形成薄膜的能力也优异。电子注入层的具体实例包含芴酮、蒽醌二甲烷、二苯醌、噻喃二氧化物、唑、二唑、三唑、咪唑、苝四羧酸、亚芴基甲烷、蒽酮等、及其衍生物,金属配合物化合物,含氮5元环衍生物等,但不限于此。
金属配合物化合物的实例包括8-羟基喹啉锂、双(8-羟基喹啉)锌、双(8-羟基喹啉)铜、双(8-羟基喹啉)锰、三(8-羟基喹啉)铝、三(2-甲基-8-羟基喹啉)铝、三(8-羟基喹啉)镓、双(10-羟基苯并[h]喹啉)铍、双(10-羟基苯并[h]喹啉)锌、双(2-甲基-8-喹啉)氯镓、双(2-甲基-8-喹啉)(邻甲酚)镓、双(2-甲基-8-喹啉)(1-萘酚)铝、双(2-甲基-8-喹啉)(2-萘酚)镓等,但不限于此。
根据使用的材料,根据本发明的有机发光器件可以为前发射型、后发射型、或双侧发射型。
此外,除了有机发光器件之外,由化学式1表示的化合物可以包含在有机太阳能电池或有机晶体管中。
由化学式1表示的化合物和包含其的有机发光器件的制备将在以下实施例中详细描述。然而,这些实施例仅为了说明性目的而提出,并不旨在限制本发明的范围。
制备例1:中间体A-5的制备
1)化合物A-1的合成
将2-溴苯酚(49.4g,287.3mmol)和2-氯-6-氟苯基硼酸(50.0g,287.3mmol)溶解在500ml四氢呋喃(THF)中。向其中添加2M碳酸钠(Na2CO3)水溶液(430mL)和四(三苯基膦)钯(0)[Pd(PPh3)4](10.0g,8.6mmol),并回流12小时。在反应完成之后,使反应混合物冷却至室温,并用水和甲苯萃取所得混合物三次。分离甲苯层,用硫酸镁干燥,过滤,并将滤液在减压下蒸馏。通过柱色谱法使用氯仿和己烷对所得混合物进行纯化以获得化合物A-1(34.4g,产率:54%)。
MS:[M+H]+=223
2)化合物A-2的合成
将化合物A-1(30g,135.1mmol)溶解在300ml氯仿中。向其中添加N-溴代琥珀酰亚胺(160.3g,270.25mmol)并在室温下搅拌4小时。在反应完成之后,添加水。在层分离之后,将混合物与硫代硫酸钠溶液搅拌两次,并分离层。然后,进行蒸馏以获得化合物A-2(51.1g,产率:100%)。
MS:[M+H]+=379
3)化合物A-3的合成
将化合物A-2(51.1g,135.1mmol)溶解在经蒸馏的二甲基甲酰胺(DMF)(400ml)中。将其冷却至0℃,并向其中缓慢逐滴添加氢化钠(3.5g,145.9mmol)。将混合物搅拌20分钟,然后在100℃下搅拌1小时。在反应完成之后,使反应混合物冷却至室温,并缓慢添加100ml乙醇。将混合物在减压下蒸馏,并将所得混合物从氯仿和乙酸乙酯中重结晶以获得化合物A-3(32.9g,产率:68%)。
MS:[M+H]+=359
4)化合物A-4的合成
将化合物A-3(32.9g,91.9mmol)和苯基硼酸(24.7g,202.3mmol)溶解在300ml四氢呋喃(THF)中。向其中添加2M碳酸钾水溶液(K2CO3)(140ml)和四(三苯基膦)钯(0)[Pd(PPh3)4](2.1g,2mmol%),并回流6小时。在反应完成之后,使反应混合物冷却至室温,并用水和甲苯萃取所得混合物三次。分离甲苯层,用硫酸镁干燥,过滤,并将滤液在减压下蒸馏。通过柱色谱法使用氯仿和乙酸乙酯对所得混合物进行纯化以获得化合物A-4(20.8g,产率:64%)。
MS:[M+H]+=355
5)化合物A-5的合成
将化合物A-4(20.8g,58.7mmol)、双(频哪醇)二硼(25.0g,70.6mmol)、乙酸钾(16.9g,176.2mmol)、双(二亚苄基丙酮)钯(1.0g,1.8mmol)和三环己基膦(1.0g,3.5mmol)添加到二烷(300ml)中并回流12小时。在反应完成之后,使反应混合物冷却至室温并使用在减压下的蒸馏来除去溶剂。将其溶解在氯仿中并用水洗涤3次。分离有机层并用硫酸镁干燥。将其在减压下蒸馏以获得化合物A-5(25.0g,产率:77%)。
MS:[M+H]+=447
[实施例]
实施例1:化合物1的制备
在氮气氛下将化合物A-5(10g,22.4mmol)和2-氯-4,6-二苯基-1,3,5-三嗪(6.0g,22.4mmol)添加到100ml四氢呋喃中,将混合物搅拌并回流。然后,将碳酸钾(9.3g,67mmol)添加并溶解在30ml水中并充分搅拌,并向其中添加四(三苯基膦)钯(0)[Pd(PPh3)4](0.5g,2.2mmol)。在反应4小时之后,使反应混合物冷却至室温并过滤。滤液用氯仿和水萃取,用硫酸镁干燥有机层。随后,将有机层在减压下蒸馏,然后用乙酸乙酯重结晶。将所得固体过滤,然后干燥以制备化合物1(8.7g,71%)。
MS:[M+H]+=552
实施例2:化合物2的制备
以与实施例1中相同的方式制备化合物2(10.8g,77%),不同之处在于在以上反应方案所示的反应中,使用2-([1,1’-联苯基]-4-基)-4-氯-6-苯基-1,3,5-三嗪代替2-氯-4,6-二苯基-1,3,5-三嗪。
MS:[M+H]+=628
实施例3:化合物3的制备
以与实施例1中相同的方式制备化合物3(9.5g,66%),不同之处在于在以上反应方案所示的反应中,使用9-(4-氯-6-苯基-1,3,5-三嗪-2-基)-9H-咔唑代替2-氯-4,6-二苯基-1,3,5-三嗪。
MS:[M+H]+=628
实施例4:化合物4的制备
以与实施例1中相同的方式制备化合物4(7.4g,51%),不同之处在于在以上反应方案所示的反应中,使用2-氯-4-(二苯并[b,d]呋喃-4-基)-6-苯基-1,3,5-三嗪代替2-氯-4,6-二苯基-1,3,5-三嗪。
MS:[M+H]+=642
实施例5:化合物5的制备
以与实施例1中相同的方式制备化合物5(9.3g,63%),不同之处在于在以上反应方案所示的反应中,使用2-氯-4-(二苯并[b,d]噻吩-4-基)-6-苯基-1,3,5-三嗪代替2-氯-4,6-二苯基-1,3,5-三嗪。
MS:[M+H]+=658
实施例6:化合物6的制备
以与实施例1中相同的方式制备化合物6(13.0g,81%),不同之处在于在以上反应方案所示的反应中,使用9-(4-(4-氯-6-苯基-1,3,5-三嗪-2-基)苯基)-9H-咔唑代替2-氯-4,6-二苯基-1,3,5-三嗪。
MS:[M+H]+=717
实施例7:化合物7的制备
以与实施例1中相同的方式制备化合物7(8.5g,53%),不同之处在于在以上反应方案所示的反应中,使用9-(3-(4-氯-6-苯基-1,3,5-三嗪-2-基)苯基)-9H-咔唑代替2-氯-4,6-二苯基-1,3,5-三嗪。
MS:[M+H]+=717
实施例8:化合物8的制备
以与实施例1中相同的方式制备化合物8(9.5g,59%),不同之处在于在以上反应方案所示的反应中,使用2-(4-氯-6-苯基-1,3,5-三嗪-2-基)-9-苯基-9H-咔唑代替2-氯-4,6-二苯基-1,3,5-三嗪。
MS:[M+H]+=717
实施例9:化合物9的制备
以与实施例1中相同的方式制备化合物9(11.9g,74%),不同之处在于在以上反应方案所示的反应中,使用3-(4-氯-6-苯基-1,3,5-三嗪-2-基)-9-苯基-9H-咔唑代替2-氯-4,6-二苯基-1,3,5-三嗪。
MS:[M+H]+=717
[实验例]
实验例1
将其上涂覆有作为薄膜的厚度为的ITO(氧化铟锡)的玻璃基底放入其中溶解有清洁剂的蒸馏水中,并进行超声清洗。在这种情况下,使用由Fischer Co.制造的产品作为清洁剂,以及作为蒸馏水,使用利用由Millipore Co.制造的过滤器过滤两次的蒸馏水。在将ITO清洗30分钟之后,使用蒸馏水重复两次超声清洗10分钟。在用蒸馏水清洗完成之后,用异丙醇、丙酮和甲醇溶剂对基底进行超声清洗,然后干燥,然后转移至等离子体清洗器。此外,使用氧等离子体将基底清洗5分钟,然后转移至真空沉积器。
在由此制备的ITO透明电极上,热真空沉积以下化合物HI-1至的厚度以形成空穴注入层。在空穴注入层上真空沉积以下化合物HT-1至的厚度以形成空穴传输层,并在空穴传输层上真空沉积以下化合物HT-2至的厚度以形成电子阻挡层。然后,在电子阻挡层上以44:44:12的重量比共沉积在先前实施例1中制备的化合物1、以下化合物YGH-1、和磷光掺杂剂YGD-1以形成厚度为的发光层。在发光层上真空沉积以下化合物ET-1至的厚度以形成电子传输层,并以98:2的重量比真空沉积以下化合物ET-2和Li以形成厚度为的电子注入层。在电子注入层上沉积铝至的厚度以形成阴极。
实验例2至9和比较实验例1至3
以与实验例1中相同的方式制造有机发光器件,不同之处在于使用下表1所示的化合物代替实施例1中制备的化合物1。
然而,下表1中的CE1、CE12和CE3的化合物如下:
对于以上实验例和比较实验例中制造的有机发光器件,在10mA/cm2的电流密度下测量电压和效率,并且在50mA/cm2的电流密度下测量寿命。结果示于下表1中。此时,LT95意指亮度降低到初始亮度的95%所需的时间。
[表1]
参照上表1,确定与比较实验例相比,使用本发明的化合物作为发光层材料的实验例具有明显降低的电压、以及优异的效率和寿命特性。具体地,实施例1至9中制备的化合物1至9具有其中二苯并呋喃取代基的2位和4位经苯基取代的结构,因此,当用作有机发光器件的主体时,预测有机发光器件的电子稳定性优异。
附图标记说明
1:基底 2:阳极
3:发光层 4:阴极
5:空穴注入层 6:空穴传输层
7:电子阻挡层 8:电子传输层
9:电子注入层
Claims (9)
1.一种由以下化学式1表示的化合物:
[化学式1]
其中,在化学式1中,
Y1为O或S,
Ar1为经取代的C6-60芳基;或者经取代或未经取代的包含选自O、N、Si和S中的一个或更多个杂原子的C1-60杂芳基,
L为单键;经取代或未经取代的C6-60亚芳基;或者经取代或未经取代的包含选自O、N、Si和S中的一个或更多个杂原子的C1-60亚杂芳基,
R1至R5各自独立地为氢;氘;卤素;氰基;硝基;氨基;经取代或未经取代的C1-60烷基;经取代或未经取代的C1-60卤代烷基;经取代或未经取代的C1-60烷氧基;经取代或未经取代的C1-60卤代烷氧基;经取代或未经取代的C3-60环烷基;经取代或未经取代的C2-60烯基;经取代或未经取代的C6-60芳基;经取代或未经取代的C6-60芳氧基;或者经取代或未经取代的包含选自N、O和S中的一个或更多个杂原子的C1-60杂芳基,以及
n1至n3各自独立地为1至5的整数。
2.根据权利要求1所述的化合物,其中Ar1为选自以下的任一者:
其中,
X1至X3各自独立地为N或CR’3,条件是X1至X3中的至少两者为N,
Y2和Y3各自独立地为O、S或NR’,
Ar2至Ar5各自独立地为经取代或未经取代的C6-60芳基;或者经取代或未经取代的包含选自O、N、Si和S中的一个或更多个杂原子的C1-60杂芳基,
每个R’独立地为氢;氘;卤素;氰基;硝基;氨基;经取代或未经取代的C1-60烷基;经取代或未经取代的C1-60卤代烷基;经取代或未经取代的C1-60烷氧基;经取代或未经取代的C1-60卤代烷氧基;经取代或未经取代的C3-60环烷基;经取代或未经取代的C2-60烯基;经取代或未经取代的C6-60芳基;经取代或未经取代的C6-60芳氧基;或者经取代或未经取代的包含选自N、O和S中的一个或更多个杂原子的C1-60杂芳基,以及
n4至n11可以各自独立地为1至5的整数。
5.根据权利要求1所述的化合物,其中R1至R3各自独立地为氢;氘;氰基;或者经取代或未经取代的C1-10烷基。
7.一种有机发光器件,包括:第一电极;与所述第一电极相对设置的第二电极;以及设置在所述第一电极与所述第二电极之间的一个或更多个有机材料层,其中所述有机材料层的一个或更多个层包含根据权利要求1至6中任一项所述的化合物。
8.根据权利要求7所述的有机发光器件,其中包含所述化合物的所述有机材料层包括空穴注入层、空穴传输层、电子阻挡层、发光层、电子传输层、或电子注入层。
9.根据权利要求7所述的有机发光器件,其中所述发光层包含两种或更多种主体,并且所述主体中的一者为所述化合物。
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