CN111393424B - 芴螺三苯胺化合物、有机电子器件及显示器件或照明器件 - Google Patents
芴螺三苯胺化合物、有机电子器件及显示器件或照明器件 Download PDFInfo
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- CN111393424B CN111393424B CN202010366067.2A CN202010366067A CN111393424B CN 111393424 B CN111393424 B CN 111393424B CN 202010366067 A CN202010366067 A CN 202010366067A CN 111393424 B CN111393424 B CN 111393424B
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Abstract
本发明提供一种芴螺三苯胺化合物、有机电子器件及显示器件或电子器件,该芴螺三苯胺化合物通过引入芴螺三苯胺刚性结构,使其成膜性和热稳定性优异,可用于制备有机电致发光器件、有机场效应晶体管和有机太阳能电池。另外,本发明的芴螺三苯胺化合物可以作为空穴注入层、空穴传输层、发光层、电子阻挡层、空穴阻挡层或电子传输层的构成材料,能够降低驱动电压,提高效率、亮度和寿命等。更为重要的是,本发明的芴螺三苯胺化合物能有效地隔离给体和受体基团,从而是构建热激活延迟荧光材料的理想骨架。本发明的芴螺三苯胺化合物的制备方法简单,原料易得,能够满足工业化的发展需求。
Description
技术领域
本发明涉及一种芴螺三苯胺化合物、有机电子器件及显示器件或照片器件,属于有机光电材料技术领域。
背景技术
有机发光二极管(OLED)是一种自发光器件,通过施加电压,从阴极注入的电子和阳极注入的空穴在发光中心复合形成分子激子,并且该分子激子在回到基态时释放能量来发光。有机电致发光器件具有开启电压低、亮度高、色域广、色纯度高、视角宽、响应快、温度适应性好等特性,可以广泛应用于手机、电脑、MP3、电视等电子产品显示器。
目前商业化的有机电致发光材料分为传统荧光材料和磷光材料,其中荧光材料只能利用25%的单线态激子,剩余的75%三线态激子通过热或者其他无辐射方式损失,而磷光材料由于重原子效应可以利用100%的激子,虽然使其发光效率远高于传统荧光材料,但是大部分磷光器件大都具有较为严重的效率滚降,即在较低亮度或较低电流密度下具有最大效率,随着亮度或电流密度的增大,器件的外量子效率普遍出现严重的降低并且受到贵重金属价格的制约。这无疑增加了器件的成本,影响了有机电致磷光器件在照明和全彩显示上的应用。
通过设计新型热激活延迟荧光客体材料改善有机电致磷光器件的器件效率与降低成本是一种简单且实际的方法。目前报道过的芴螺三苯胺类化合物、氧杂芴螺三苯胺类化合物作为客体材料可以提高有机电致磷光器件的器件效率并改善器件的效率滚降,但是仍有进一步提升的空间。
发明内容
本发明的目的在于提供一种芴螺三苯胺化合物、有机电子器件及显示器件或照片器件,能有效提高三线态能级,减小单线态与三线态能隙差和提高荧光量子产率以及热稳定性,从而改善有机电致发光器件的发光效率、效率滚降和工作电压等性能。
为达到上述目的,本发明提供如下技术方案:一种芴螺三苯胺化合物,其特征在于,其由下述通式(1)表示:
其中,R1~R3各自独立地表示氰基或任选被一个或多个R1取代的、具有6 至30个碳原子的芳香族烃基或任选被一个或多个R1取代的、具有5至30个碳原子的芳香族杂环基中的一个或多个;
Z表示CR1或者N;
R1表示氢原子、氘原子、氟原子、氯原子、溴原子、碘原子、氰基、 NO2、N(R2)2、OR2、SR2、C(=O)R2、P(=O)R2、Si(R2)3、取代或未取代的具有1 至20个碳原子的烷基、取代或未取代的具有2至20个碳原子的烯基、取代或未取代的具有2至20个碳原子的炔基、取代或未取代的具有6至40个碳原子的芳香族烃基、或取代或未取代的具有5至40个碳原子的芳香族杂环基中的一个或多个;
R2表示氢原子、氘原子、氟原子、氰基、取代或未取代的具有1至20个碳原子的烷基、取代或未取代的具有6至30个碳原子的芳香族烃基或取代或未取代的具有5至30个碳原子的芳香族杂环基中的一个或多个。
进一步地,所述R1、R2和R3各自独立地选自氰基或者以下通式Ar-1至 Ar-39中的任一种:
其中,波浪线表示与芴螺三苯胺母核键合的键,
R1具有根据权利要求1所定义的含义。
进一步地,R1和R2表示苯基、联苯基、三联苯基、四联苯基、五联苯基、苯并噻吩并咔唑、苯并呋喃并咔唑、苯并芴并咔唑、苯并蒽、苯并菲、芴基、螺双芴基、三嗪基、二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基、茚并咔唑基、苯并咪唑基、二苯基-苯并咪唑基、二苯基-噁二唑基、二苯基硼基、三苯基磷氧基、二苯基磷氧基、三苯基硅基或四苯基硅基中的一个或多个。
进一步地,所述芴螺三苯胺化合物选自以下通式1-1至1-40中的任一种:
本发明还提供一种根据所述的芴螺三苯胺化合物的制备方法,包括以下步骤:
通过2,4和7位官能化的芴螺三苯胺进行金属催化偶联反应或者锂试剂亲核反应引入所述R1、R2和R3基团。
本发明还提供根据所述的芴螺三苯胺化合物在用于制备电子器件中的应用,所述电子器件选自有机电致发光器件、有机场效应晶体管或有机太阳能电池,尤其是在用于制备有机电致发光器件中的发光客体材料、发光主体材料、激子阻挡材料或电子传输材料的应用。
本发明还提供一种电子器件,其具有所述的芴螺三苯胺化合物。
进一步地,所述电子器件为有机电致发光器件,所述有机电致发光器件包括有机发光层、激子阻挡层以及电子传输层,所述有机电致发光器件中具有所述芴螺三苯胺化合物。
与现有技术相比,本发明的有益效果在于:本发明的芴螺三苯胺化合物通过引入芴螺三苯胺刚性结构,其的成膜性和热稳定性优异,可用于制备有机电致发光器件、有机场效应晶体管和有机太阳能电池。另外,本发明的芴螺三苯胺化合物可以作为空穴注入层、空穴传输层、发光层、电子阻挡层、空穴阻挡层或电子传输层的构成材料,能够降低驱动电压,提高效率、亮度和寿命等。更为重要的是,本发明的芴螺三苯胺化合物能有效地隔离给体和受体基团,从而是构建热激活延迟荧光材料的理想骨架。本发明的芴螺三苯胺化合物的制备方法简单,原料易得,能够满足工业化的发展需求。
上述说明仅是本发明技术方案的概述,为了能够更清楚了解本发明的技术手段,并可依照说明书的内容予以实施,以下以本发明的较佳实施例并配合附图详细说明如后。
附图说明
图1为本发明实施例5中化合物1-25的紫外吸收光谱(UV-Vis)、室温荧光光谱(PL)以及低温磷光光谱(Phos);
图2为本发明实施例7中OLED器件的有机电致发光光谱图。
具体实施方式
下面结合附图和实施例,对本发明的具体实施方式作进一步详细描述。以下实施例用于说明本发明,但不用来限制本发明的范围。
本发明提供了一种芴螺三苯胺化合物,为包含以下通式(1)表示的化合物:
其中,R1~R3各自独立地表示氢原子、氰基或任选被一个或多个R1取代的、具有6至30个碳原子的芳香族烃基或任选被一个或多个R1取代的、具有 5至30个碳原子的芳香族杂环基中的一个或多个;
Z表示CR1或者N;
R1表示氢原子、氘原子、氟原子、氯原子、溴原子、碘原子、氰基、 NO2、N(R2)2、OR2、SR2、C(=O)R2、P(=O)R2、Si(R2)3、取代或未取代的具有1 至20个碳原子的烷基、取代或未取代的具有2至20个碳原子的烯基、取代或未取代的具有2至20个碳原子的炔基、取代或未取代的具有6至40个碳原子的芳香族烃基、或取代或未取代的具有5至40个碳原子的芳香族杂环基中的一个或多个;
R2表示氢原子、氘原子、氟原子、氰基、取代或未取代的具有1至20个碳原子的烷基、取代或未取代的具有6至30个碳原子的芳香族烃基或取代或未取代的具有5至30个碳原子的芳香族杂环基中的一个或多个。
<R1和R3>
R1~R3各自独立地表示氢原子、氰基或任选被一个或多个R1取代的、具有6至 30个碳原子的芳香族烃基或任选被一个或多个R1取代的、具有5至30个碳原子的芳香族杂环基中的一个或多个。
由R1~R3表示的具有6至30个碳原子的芳香族烃基或具有5至30个碳原子的芳香族杂环基可以例示出:苯基、萘基、蒽基、苯并蒽基、菲基、苯并菲基、芘基、苝基、荧蒽基、苯并荧蒽基、并四苯基、并五苯基、苯并芘基、联苯基、偶苯基、三联苯基、四联苯基、五联苯基、三聚苯基、芴基、螺双芴基、二氢菲基、二氢芘基、四氢芘基、顺式或反式茚并芴基、顺式或反式单苯并茚并芴基、顺式或反式二苯并茚并芴基、三聚茚基、异三聚茚基、螺三聚茚基、螺异三聚茚基、呋喃基、苯并呋喃基、异苯并呋喃基、二苯并呋喃基、噻吩基、苯并噻吩基、异苯并噻吩基、二苯并噻吩基、苯并噻吩并咔唑基、吡咯基、吲哚基、异吲哚基、咔唑基、吲哚并咔唑基、茚并咔唑基、吡啶基、联吡啶基、三联吡啶基、喹啉基、异喹啉基、吖啶基、菲啶基、苯并-5,6-喹啉基、苯并-6,7-喹啉基、苯并-7,8-喹啉基、吩噻嗪基、吩噁嗪基、吡唑基、吲唑基、咪唑基、苯并咪唑基、萘并咪唑基、菲并咪唑基、吡啶并咪唑基、吡嗪并咪唑基、喹喔啉并咪唑基、噁唑基、苯并噁唑基、苯并噁二唑基、萘并噁唑基、蒽并噁唑基、菲并噁唑基、异噁唑基、噻唑基、异噻唑基、苯并噻唑基、苯并噻二唑基、哒嗪基、苯并哒嗪基、嘧啶基、苯并嘧啶基、喹喔啉基、喹唑啉基、氮杂芴基、二氮杂蒽基、二氮杂芘基、四氮杂苝基、二氮杂萘基、吡嗪基、吩嗪基、吩噁嗪基、吩噻嗪基、荧红环基、萘啶基、氮杂咔唑基、苯并咔啉基、菲咯啉基、***基、苯并***基、噁二唑基、噻二唑基、三嗪基、四唑基、四嗪基、嘌呤基、蝶啶基、吲嗪基、苯并噻二唑基、吡啶并吡咯基、吡啶并***基、呫吨基、苯并呋喃并咔唑基、苯并芴并咔唑基、N-苯基咔唑基、二苯基-苯并咪唑基、二苯基-噁二唑基、二苯基硼基、三苯基磷氧基、二苯基磷氧基、三苯基硅基、四苯基硅基等。
在本发明中,优选地,R1~R3各自独立地选自氢原子、氰基或下述基团:
其中,波浪线表示与母核键合的键,R1具有上述所定义的含义。
由R1~R3表示的具有6至30个碳原子的芳香族烃基或具有5至30个碳原子的芳香族杂环基可以是未取代的,但也可以具有取代基。优选地,由Ar1~Ar6表示的具有6至30个碳原子的芳香族烃基或具有5至30个碳原子的芳香族杂环基是被一个或多个R1取代的、具有5至30个碳原子的芳香族烃基或被一个或多个R1取代的、具有5至30个碳原子的芳香族杂环基。
<R1>
R1表示氢原子、氘原子、氟原子、氯原子、溴原子、碘原子、氰基、NO2、 N(R2)、OR2、SR2、C(=O)R2、P(=O)R2、Si(R2)3、取代或未取代的具有1至20个碳原子的烷基、取代或未取代的具有2至20个碳原子的烯基、取代或未取代的具有 2至20个碳原子的炔基、取代或未取代的具有6至40个碳原子的芳香族烃基、或取代或未取代的具有5至40个碳原子的芳香族杂环基中的一个或多个。
由R1表示的具有1至20个碳原子的烷基可以例示出:甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、新戊基、正己基、正庚基、 2-甲基己基、正辛基、异辛基、叔辛基、2-乙基己基、3-甲基庚基、正壬基、正癸基、十六烷基、十八烷基、二十烷基、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。具有1至20个碳原子的烷基可以是直链、支链或环状的。
由R1表示的具有1至20个碳原子的烷基可以是未取代的,但也可具有取代基。优选地,由R1表示的具有1至20个碳原子的烷基被一个或多个下述R2取代。另外,所述烷基中的一个或多个非相邻的CH2基团可以被R2C=CR2、C≡C、Si(R2)3、C=O、 C=NR2、P(=O)R2、SO、SO2、NR2、O、S或CONR2代替,并且其中一个或者多个氢原子可以被氘原子、氟原子、氯原子、溴原子、碘原子、氰基、硝基代替。
由R1表示的具有2至20个碳原子的烯基可以例示出:乙烯基、丙烯基、丁烯基、戊烯基、己烯基、庚烯基、辛烯基、壬烯基、癸烯基、十一烯基、十二烯基、十三烯基、十四烯基、十五烯基、十六烯基、十七烯基、十八烯基、十九烯基、二十烯基、2-乙基己烯基、烯丙基或环己烯基等。具有2至20个碳原子的烯基可以是直链、支链或环状的。
由R1表示的具有2至20个碳原子的烯基可以是未取代的,或可以具有取代基。取代基可以例示为与由R1表示的具有1至20个碳原子的烷基任选地具有的取代基所示的相同的取代基。取代基可以采用的模式与示例性取代基的模式相同。
由R1表示的具有2至20个碳原子的炔基可以例示出:乙炔基、异丙炔基、丁炔基、戊炔基、己炔基、庚炔基、辛炔基、壬炔基、癸炔基等。
由R1表示的具有2至20个碳原子的炔基可以是未取代的,或可以具有取代基。取代基可以例示为与由R1表示的具有1至20个碳原子的烷基任选地具有的取代基所示的相同的取代基。取代基可以采用的模式与示例性取代基的模式相同。
由R1表示的具有6至40个碳原子的芳香族烃基或具有5至40个碳原子的芳香族杂环基可以列举出于前述由Ar1~Ar6表示的具有6至30个碳原子的芳香族烃基或具有5至30个碳原子的芳香族杂环基示出的基团相同的基团。
由R1表示的具有6至40个碳原子的芳香族烃基或具有5至40个碳原子的芳香族杂环基可以是未取代的,或可以具有取代基。取代基可以例示为与由R1表示的具有1至20个碳原子的烷基任选地具有的取代基所示的相同的取代基。取代基可以采用的模式与示例性取代基的模式相同。此外,两个相邻的R1取代基或两个相邻的R2取代基任选可形成单环或多环的脂肪族、芳香族或者杂芳香族的环系,所述环系可以被一个或多个R2取代;在此处两个或多个取代基R1可以彼此连接并可以形成环。
作为优选的由R1表示的具有6至40个碳原子的芳香族烃基或具有5至40个碳原子的芳香族杂环基,可以列举:苯基、联苯基、三联苯基、四联苯基、五联苯基、苯并噻吩并咔唑基、苯并呋喃并咔唑基、苯并芴并咔唑基、苯并蒽基、苯并菲基、芴基、螺双芴基、三嗪基、二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基、茚并咔唑基、苯并咪唑基、二苯基-苯并咪唑基、二苯基-噁二唑基、二苯基硼基、三苯基磷氧基、二苯基磷氧基、三苯基硅基、四苯基硅基等。所述具有6至40个碳原子的芳香族烃基或具有5至40个碳原子的芳香族杂环基可以被一个或多个R2取代。
<R2>
R2表示氢原子、氘原子、氟原子、氰基、取代或未取代的具有1至20个碳原子的烷基、取代或未取代的具有6至30个碳原子的芳香族烃基或取代或未取代的具有5至30个碳原子的芳香族杂环基中的一个或多个。
由R2表示的具有1至20个碳原子的烷基可以列举出与前述由R1表示的具有1 至20个碳原子的烷基示出的基团相同的基团。
由R2表示的具有6至30个碳原子的芳香族烃基或取代或未取代的具有5至30 个碳原子的芳香族杂环基可以列举出与前述由R1表示的具有6至30个碳原子的芳香族烃基或取代或未取代的具有5至30个碳原子的芳香族杂环基示出的基团相同的基团。
由R2表示的具有1至20个碳原子的烷基、具有6至30个碳原子的芳香族烃基或取代或未取代的具有5至30个碳原子的芳香族杂环基可以是未取代的,或也可以具有取代基。取代基可以例示出:氘原子;卤素原子,例如氟原子、氯原子、溴原子或碘原子;氰基等。
<Z>
Z表示CR1或者N,例如N、C-H、C-F、C-Cl、C-Br、C-I、C-CN、C-NO2、碳-苯基、碳-联苯基等。
R1具有如上所定义的含义。
在本发明的一种特别优选的实施方式中:
其中,R1、R2和R3各自独立地选自氰基或者以下芳族或杂芳族环系:吡啶基、二苯胺基、二甲基硼烷基、二苯基三嗪基;所述芳族或杂芳族环系可被一个或多个R1取代;
各位点的R1基团独立地选自:氢、具有1至5个C原子的直链烷基。
优选的,所述芴螺三苯胺化合物选自以下通式1-1至1-40中的任一种:
本发明还提供一种根据所述的芴螺三苯胺化合物的制备方法,包括以下步骤:
可通过本领域普通技术人员已知的合成步骤,例如溴化、铃木(Suzuki)偶联、布赫瓦尔德-哈特维希(Hartwig-Buchwald)偶联等,来制备根据本发明的化合物。
本发明的化合物合成通常从2,4和7位官能化的芴螺三苯胺化合物开始,然后通过锂试剂亲核反应或者金属催化偶联反应如铃木(Suzuki)偶联或者布赫瓦尔德-哈特维希(Hartwig-Buchwald)偶联而引入R1、R2和R3基团。
在本发明的一种优选实施方式中,所述芴螺三苯胺化合物是利用硼酸化合物官能化的化合物,且R1、R2和R3基团源自卤素官能化的化合物。在本发明的另一种优选的实施方式中,所述芴螺三苯胺化合物是卤素官能化的化合物,且R R1、R2和R3基团源自硼酸化合物官能化的化合物。
在本发明的第三种优选实施方式中,所述芴螺三苯胺化合物是卤素官能化的化合物,在钯类催化剂的作用下与胺类化合物的化合物反应而引入R1、R2和 R3基团。其中,卤素官能化优选溴化、氯化、碘化,特别是溴化。
在本发明的第四种优选实施方式中,所述芴螺三苯胺化合物是卤素官能化的化合物,在锂试剂的作用下与磷基化或者硅基化或者硼基化的化合物反应而引入R1、R2和R3基团。其中,卤素官能化优选溴化、氯化、碘化,特别是溴化。
具体而言,如上所述的第一种优选实施方式,需先制备硼酸官能化的芴螺三苯胺化合物(中间体M3),优选的制备步骤示例如下:
通过控制反应条件,M1的收率可达到80-92%,M2的收率可达到60-80%, M3的收率可到70-85%。得到中间体M3后,在体系中加入可引入R1、R2和R3基团的卤素官能化化合物如2,4-二氯-6-苯基-1,3,5-三嗪或三聚氰胺,以及一定量的钯类催化剂如四(三苯基磷钯)、无水碳酸钾、四氢呋喃和水,在氮气保护下 50-80℃下反应30-35小时,反应完毕。蒸去溶剂,用二氯甲烷和水溶解残留物,水洗,分出有机层,水层用二氯甲烷萃取,合并有机层,用水洗两次至中性,蒸去溶剂后,柱层析分离,干燥得到产物。中间体M3与四(三苯基磷钯)的摩尔比在15-20:1,优选18:1;通过调节反应条件,收率在65-85%。
如上所述的第二种优选实施方式,优选利用M2和硼酸化合物官能化的化合物吡啶-3-硼酸反应,在体系中加入四(三苯基膦)钯、无水碳酸钾、四氢呋喃和水,在氩气保护下50-80℃下反应30-35小时,反应完毕。后处理同第一种优选实施方式。最终产品收率可达到79%。
如上所述的第三种优选实施方式,优选利用M2和胺类化合物官能化的化合物二苯胺反应,在体系中加入三(二亚苄基丙酮)二钯、叔丁醇钠、四氟硼酸三叔丁基膦、甲苯,在氩气保护下90-120℃下反应10-30小时,反应完毕。抽滤,减压蒸去溶剂,柱层析分离,干燥得到产物。中间体M2与三(二亚苄基丙酮)二钯的摩尔比在15-20:1,优选18:1;通过调节反应条件,收率可达78%。
如上所述的第四种优选实施方式,优选利用M2在四氢呋喃中溶解,低温下滴加正丁基锂,在-78℃搅拌1小时,然后,将溶解在四氢呋喃中的硼基官能化的化合物如二(三甲苯基)氟化硼慢慢滴加到反应瓶中,1小时后自动升温,反应过夜。在反应瓶中加入少量水淬灭反应,减压蒸去溶剂,柱层析分离,干燥得到产物,收率可达78%。
本发明还提供根据所述的芴螺三苯胺化合物在用于制备电子器件中的应用,所述电子器件选自有机电致发光器件、有机场效应晶体管或有机太阳能电池,尤其是在用于制备有机电致发光器件中的发光主体材料、激子阻挡材料或电子传输材料的应用。
本发明另外还涉及包含至少一种本发明化合物的电子器件。所述电子器件优选地选自有机电致发光器件(有机发光二极管、OLED)、有机场效应晶体管 (O-FET)、有机太阳能电池(O-SC)、有机薄膜晶体管(O-TFT)、有机发光晶体管(O-LET)、有机集成电路(O-IC)、有机染料敏化太阳能电池(ODSSC)、有机光学检测器、有机光感受器、有机场猝熄器件(O-FQD)、发光电化学电池 (LEC)、有机激光二极管(O-laser)和有机等离子体发射器件等,优选有机电致发光器件(OLED)。
一个OLED总体上包括:基板,例如(但不限于)玻璃、塑料、金属;阳极,例如氧化铟锡(ITO)阳极;空穴注入层(HIL);空穴传输层(HTL);电子阻挡层(EBL);有机发光层(EML);激子阻挡层(EBL);电子传输层(ETL);电子注入层(EIL),例如Liq、Cs2CO3;阴极,例如Al。然而,应该指出,中间每层可以有一层或多层并且每层并非必须存在。
本发明的化合物可以用于该器件的任意一层或多层,但优选用于发光层 (EML),更优选为发光层的主体材料,因为其具有高的三线态能级,稳定性好。本发明的化合物也可以用于作为激子阻挡材料或者电子传输材料用于激子阻挡层(EBL)和电子传输层(ETL)中,因其载流子传输能力好。
本发明的有机发光层掺杂剂并无特别限定,优选为发光金属配合物和发光有机分子,发光金属配合物优选为铱和铂的配合物,发光有机分子优选荧光化合物和热激发延迟荧光化合物。为了提高器件效能,掺杂剂质量比例在6%-30%,优选6%-20%,进一步优选6%-15%。
在本发明的优选实施方式中,OLED包括:基片/阳极/空穴注入材料(HIL) /空穴传输材料(HIL)/电子阻挡层(EBL)/有机发光层(EML)/电子传输层(ETL) /阴极。其中,基片使用玻璃基板,ITO作阳极材料。空穴注入材料使用现有技术中常用的2,3,6,7,10,11-六氰基-1,4,5,8,9,12-六氮杂苯并菲(HAT-CN),空穴传输材料使用现有技术中常用的4,4'-(环己烷-1,1-二基)双(N,N-二对甲苯基苯胺) (TAPC);电子阻挡层使用现有技术中常用的三(4-(9H-咔唑-9-基)苯基)胺 (TCTA);有机发光层使用本发明所述化合物掺杂于现有技术中常用的主体材料9,9'-(1,3-苯基)二-9H-咔唑(mCP)和4,4'-二(9-咔唑)联苯(CBP)。另外,本发明所述化合物掺杂8-羟基喹啉-锂或者金属锂也可用作电子传输层,部分器件也使用现有技术中常用的双(10-羟基苯并[H]喹啉)铍(Be(bq)2)和三(8-羟基喹啉)铝 (Alq3)。阴极采用金属及其混合物结构,如Mg:Ag、Ca:Ag等,也可以是电子注入层/金属层结构,如LiF/Al、Liq/Al和Li2O/Al。本发明优选电子注入材料为Liq,阴极材料为Al。
以下列举实施例来说明本发明,本领域技术人员能够理解,该例子仅是示例性的说明,并非穷尽性的说明。制备例为化合物合成例,所涉及的化学原料和试剂均为市售或按公开文献合成,实施例为发光器件OLED的制备。
制备实施例
中间体M3的合成
中间体M3的结构式和合成路线如下式所示:
式M1化合物的制备方法为:在100mL两口烧瓶中,1.6g(6.2mmol)4- 溴-芴酮溶解在50mL二氯甲烷,置于冰浴中搅拌。用恒压滴液漏斗滴加0.67mL (12.8mmol)液溴。加毕,逐渐将体系升温到室温,反应6小时。反应完全后,将反应液倒入饱和亚硫酸氢钠溶液中,用二氯甲烷萃取3次,有机相用无水硫酸钠干燥后,旋干除去溶剂得粗产物。粗产物用二氯甲烷:石油醚=1:5(体积比)的洗脱剂在硅胶柱上进行分离提纯,得到2.3g M1,产率为90%。MS(EI): m/z 417.05[M+]。元素分析计算值C13H5Br3O(%):C 37.45,H 1.21;实测值:C 37.411.20
式M2化合物的制备方法为:在氮气保护下,在100mL两口烧瓶中将1.6 (4.9mmol)2-溴-三苯胺溶解在30mL无水四氢呋喃中,搅拌,冷却到-78℃。将2.3mL(5.5mmol)2.4M正丁基锂通过恒压滴液漏斗滴加到溶液中,加毕,在-78℃下继续搅拌1小时。然后将2.0g(4.9mmol)M1在氮气保护下分散到 30mL的无水四氢呋喃中并在滴加到反应液中。加毕,逐渐升至室温,反应12 小时。反应完全后,加入5mL水猝灭反应,并旋干除去四氢呋喃。将粗产物溶于150mL二氯甲烷并用60mL水洗3次。有机相用无水硫酸钠干燥后旋干除去溶剂得粗产物。粗产物用二氯甲烷:石油醚=3:1(体积比)的洗脱剂在硅胶柱上进行分离提纯,得到中间产物3.0g。在50mL两口瓶中将所得中间产物溶解在25mL醋酸中并加入2.5mL盐酸,搅拌加热至回流,反应6小时。反应完全后,将反应体系冷却至室温,倒入300mL冰水中,减压抽滤,水洗滤渣三次。将滤渣用二氯甲烷:石油醚=1:4(体积比)的洗脱剂在硅胶柱上进行分离提纯,得到2.2g M2,产率为70%。MS(EI):m/z 644.54[M+]。元素分析计算值C31H18Br3N (%):C57.80,H 2.82,N 2.17;实测值:C 57.60,H 2.80,N 2.15。
所述中间体M3的制备方法为:在100mL施兰克反应瓶中,在氩气保护下,投入2.0gM2(3.05mmol)及50mL四氢呋喃,溶解后冷却,在-78℃下滴加2.4 M正丁基锂1.3mL(3.2mmol),滴加完毕搅拌1小时,滴加硼酸三异丙酯0.8 g(4.5mmol),搅拌1小时后,自动升温,反应过夜。加入10mL氯化铵水溶液,淬灭反应。将反应物料转移到单口瓶中,减压蒸出溶剂后,在瓶中加入80 mL二氯甲烷和80mL水,溶解,水洗,分层,水层用15mL二氯甲烷萃取两次,合并有机相,再用80mL水水洗两次,至中性。分去水层,有机层加15g 无水硫酸钠,干燥3小时。减压蒸去溶剂,得白色固体1.3g,收率80%。MS (EI):m/z 539.19[M+]。元素分析计算值C31H24B3NO6(%):C 69.08,H 4.49,N 2.60;实测值:C 68.95,H 4.40,N 2.58。
实施例1
化合物1-27的结构式及合成路线如下式所示:
在氮气保护下,在100mL两口烧瓶中依次加入1.6g(2.5mmol)M2、1.11 g(9mmol)吡啶-3-硼酸、甲苯50mL、乙醇10mL、2M碳酸钠水溶液10mL、四三苯基膦钯0.15g(1.25mmol),搅拌加热至106℃反应24小时。反应完全后,将反应体系冷却至室温。用二氯甲烷萃取三次,有机相经无水碳酸钠干燥后旋干除去溶剂,得到粗产物,粗产物用二氯甲烷:石油醚=7:3(体积比)的洗脱剂在经三乙胺碱化的硅胶柱上进行分离提纯,得到1.3g 1-27,产率为79%。MS(EI):m/z 638.52[M+]。元素分析计算值C46H30N4(%):C 86.49,H 4.73,N 8.77;实测值:C86.39,H 4.70,N 8.72。
实施例2
化合物1-28的结构式及合成路线如下式所示:
在氮气保护下,在100mL两口烧瓶中依次加入1.6g(2.5mmol)M2、1.11 g(3mmol)吡啶-4-硼酸、甲苯50mL、乙醇10mL、2M碳酸钠水溶液10mL、四三苯基膦钯0.15g(1.25mmol),搅拌加热至106℃反应24小时。反应完全后,将反应体系冷却至室温。用二氯甲烷萃取三次,有机相经无水碳酸钠干燥后旋干除去溶剂,得到粗产物,粗产物用二氯甲烷:石油醚=7:3(体积比)的洗脱剂在经三乙胺碱化的硅胶柱上进行分离提纯,得到1.3g 1-28,产率为79%。MS(EI):m/z 638.52[M+]。元素分析计算值C46H30N4(%):C 86.49,H 4.73,N 8.77;实测值:C86.38,H 4.68,N 8.70。
实施例3
化合物1-6的结构式及合成路线如下式所示:
在氮气保护下,在100mL两口瓶中依次加入1.4g(2.5mmol)M3、2.4g (7.8mmol)2-氯-4,6-二苯基-1,3,5-三嗪、甲苯50mL、乙醇10mL、2M碳酸钠水溶液10mL、四三苯基膦钯0.15g(1.25mmol),搅拌加热至106℃反应24小时。反应完全后,将反应体系冷却至室温。用二氯甲烷萃取三次,有机相经无水碳酸钠干燥后旋干除去溶剂,得到粗产物,粗产物用二氯甲烷:石油醚=7:3(体积比)的洗脱剂在硅胶柱上进行分离提纯,得到2.2g 1-6,产率79%。MS(EI): m/z 1100.25[M+]。元素分析计算值C76H48N10(%):C 82.89,H 4.39,N 12.72;实测值:C 82.80,H 4.37,N 12.74。
实施例4
化合物1-10的结构式及合成路线如下式所示:
在氮气保护下,在100mL两口瓶中将3.1g(4.9mmol)M2溶解在30mL 无水四氢呋喃中,搅拌,冷却到-78℃。将2.3mL(5.5mmol)2.4M正丁基锂通过恒压滴液漏斗滴加到溶液中,加毕,在-78℃下继续搅拌1小时。然后将3.9g (14.7mmol)二(三甲苯基)氟化硼在氮气保护下分散到30mL的无水四氢呋喃中并在滴加到反应液中。加毕,逐渐升至室温,反应12小时。反应完全后,加入5mL水猝灭反应,并旋干除去四氢呋喃。将粗产物溶于150mL二氯甲烷并用60mL水洗3次。有机相用无水硫酸钠干燥后旋干除去溶剂得粗产物。粗产物用二氯甲烷:石油醚=3:1(体积比)的洗脱剂在硅胶柱上进行分离提纯,得到4.2g 1-10,产率为75%。MS(EI):m/z 1151.69[M+]。元素分析计算值 C85H84B3N(%):C 88.62,H 7.35,N 1.22;实测值:C 88.50,H 7.30,N 1.20。
实施例5
化合物1-25的结构式及合成路线如下式所示:
在氮气保护下,在100mL两口烧瓶中将3.1g(4.9mmol)M2,1.5g(15.3 mmol)氰化亚铜溶解在40mL N,N-二甲基甲酰胺中,搅拌,加热到150℃反应 24个小时。反应完全后,将反应液倒入加入50mL饱和氢氧化钠溶液中,并抽滤得到粗产物。将粗产物溶于150mL二氯甲烷并用60mL水洗3次。有机相用无水硫酸钠干燥后旋干除去溶剂得粗产物。粗产物用二氯甲烷:石油醚=3:2(体积比)的洗脱剂在硅胶柱上进行分离提纯,得到1.8g 1-25,产率为77%。MS(EI): m/z 482.36[M+]。元素分析计算值C34H18N4(%):C 84.63,H 3.76,N 11.61;实测值:C 84.47,H 3.71,N 11.50。
请参见图1,图1是产物1-25的紫外吸收光谱、紫外吸收光谱(UV-Vis)、室温荧光光谱(PL)以及低温磷光光谱(Phos)。紫外吸收光谱和室温荧光光谱分别在二氯甲烷和甲苯的稀溶液(1×10-5mol/L)中测得;低温磷光光谱在甲苯溶液(1×10-3mol/L)中测得。
实施例6
化合物1-32的结构式及合成路线如下式所示:
在250mL两口烧瓶中依次加入1.5g(2.3mmol)M2、1.5g(8.9mmol)二苯胺、0.3g(2.9mmol)叔丁醇钠、0.1g(0.3mmol)四氟硼酸三叔丁基膦、0.27 g(0.3mmol)三(二亚苄基丙酮)二钯,将反应体系除气后在氮气保护下,加入150 mL甲苯,搅拌加热至106℃反应12小时。反应完全后,将体系冷却至室温,减压抽滤,并用大量二氯甲烷洗涤滤渣,将滤液浓缩得到粗产物,粗产物用石油醚:二氯甲烷=2:3(体积比)的洗脱剂在硅胶柱上进行分离提纯,得到目标产物1.9g 1-32,产率为92%。MS(EI):m/z 908.30[M+]。元素分析计算值C67H48N4(%):C 88.52,H 5.32,N 6.16;实测值:C 88.45,H 5.30,N 6.13。
器件实施例
实施例7-15
器件制备:将涂布ITO透明导电层的玻璃板在商用清洗剂中超声处理,去离子水中冲洗,在丙酮和乙醇中各清洗三次,在洁净的环境下烘烤至完全除去水分,用紫外光和臭氧清洗,并用低能阳离子束轰击表面。把ITO导电玻璃置入真空腔内,抽真空至2×10-5-2×10-5Pa。然后在上述ITO导电玻璃上依次蒸镀空穴注入材料(HIL)、空穴传输材料(HIL)、电子阻挡层(EBL)、有机发光层(EML)、电子传输层(ETL)以及阴极;其中,有机材料的蒸镀速率为0.2nm/s,金属电极的蒸镀速率为0.5nm/s以上,发光层以双源共蒸的方法,主体材料蒸镀速率为0.2nm/s,掺杂材料的蒸镀速率为0.03nm/s。
器件性能测试:器件的电流-亮度-电压特性是由带有校正过的硅光电二极管的Keithley源测量系(Keithley 2400Sourcemeter、Keithley 2000Currentmeter) 完成的,电致发光光谱是由Photo research公司PR655光谱仪测量的,器件的外部量子效率通过文献Adv.Mater.,2003,15,1043-1048的方法计算可得。所有器件均在氮气环境中封装。
实施例涉及的化合物结构如下:
实施例7-12(分别为器件OLED1-6)的结构和各层的膜厚厚度如下:
OLED1:
ITO/HAT-CN(10nm)/TAPC(40nm)/TCTA(10nm)/2wt%1-25:CBP(15 nm)/TmPyPB(50nm)/Liq(2nm)/Al(120nm)。
OLED2:
ITO/HAT-CN(10nm)/TAPC(40nm)/TCTA(10nm)/2wt%1-10:CBP(15 nm)/TmPyPB(50nm)/Liq(2nm)/Al(120nm)。
OLED3:
ITO/HAT-CN(10nm)/TAPC(40nm)/TCTA(10nm)/2wt%1-27:CBP(15 nm)/TmPyPB(50nm)/Liq(2nm)/Al(120nm)。
OLED4:
ITO/HAT-CN(10nm)/TAPC(40nm)/TCTA(10nm)/2wt%1-28:CBP(15 nm)/TmPyPB(15nm)/Liq(2nm)/Al(120nm)。
OLED5:
ITO/HAT-CN(10nm)/TAPC(40nm)/TCTA(10nm)/2wt%1-32:CBP(15 nm)/TmPyPB(50nm)/Liq(2nm)/Al(120nm)。
OLED6:
ITO/HAT-CN(10nm)/TAPC(40nm)/TCTA(10nm)/2wt%1-6:CBP(15 nm)/TmPyPB(50nm)/Liq(2nm)/Al(120nm)。
比较例
比较例1的制备方法与实施例相同,仅是改变客体材料,其比较例1的器件结构如下:
ITO/HAT-CN(10nm)/TAPC(40nm)/TCTA(10nm)/2wt%ACRFLCN:CBP(15 nm)/TmPyPB(50nm)/Liq(2nm)/Al(120nm)。
器件的性能数据如表1所示:
表1:器件性能数据
由表1可见,本发明的化合物获得非常好的性能数据。比较例1和实施例 7采用CBP作为主体材料,区别仅在于实施例7的客体材料为本发明的化合物 1-25,通过器件性能数据的对比可见,实施例7具有更低的工作电压和更高的外量子效率,器件衰减有显著提升。请参见图2,图示为实施例7的有机电致发光光谱,由图可知其具有很强的发光强度,能量从主体材料充分转移到了客体材料中。由此可见,本发明的化合物相对于现有技术常用的材料可以有效降低工作电压、提高外量子效率和改善器件效率衰减问题。
综上所述:本发明的芴螺三苯胺化合物通过引入芴螺三苯胺刚性结构,其的成膜性和热稳定性优异,可用于制备有机电致发光器件、有机场效应晶体管和有机太阳能电池。另外,本发明的芴螺三苯胺化合物可以作为空穴注入层、空穴传输层、发光层、电子阻挡层、空穴阻挡层或电子传输层的构成材料,能够降低驱动电压,提高效率、亮度和寿命等。更为重要的是,本发明的芴螺三苯胺化合物能有效地隔离给体和受体基团,从而是构建热激活延迟荧光材料的理想骨架。本发明的芴螺三苯胺化合物的制备方法简单,原料易得,能够满足工业化的发展需求。
以上所述实施例的各技术特征可以进行任意的组合,为使描述简洁,未对上述实施例中的各个技术特征所有可能的组合都进行描述,然而,只要这些技术特征的组合不存在矛盾,都应当认为是本说明书记载的范围。
以上所述实施例仅表达了本发明的几种实施方式,其描述较为具体和详细,但并不能因此而理解为对发明专利范围的限制。应当指出的是,对于本领域的普通技术人员来说,在不脱离本发明构思的前提下,还可以做出若干变形和改进,这些都属于本发明的保护范围。因此,本发明专利的保护范围应以所附权利要求为准。
Claims (5)
2.一种有机电子器件,其特征在于,其包括:第一电极、与所述第一电极对置而具备的第二电极、以及夹在所述第一电极与所述第二电极之间的至少一个有机层,所述至少一个有机层包含权利要求1所述的化合物。
3.如权利要求2所述的有机电子器件,其特征在于,所述有机层由发光材料、敏化材料和主体材料一个或多个组成,所述化合物作为所述发光材料或敏化材料或主体材料中的任一种或多种。
4.如权利要求2所述的有机电子器件,其特征在于,在所述有机层包括空穴注入层、空穴传输层、电子阻挡层、电子传输层以及电子注入层中的一层或多层,在所述空穴注入层、空穴传输层、电子阻挡层、电子传输层以及电子注入层中的一层或多层结构中含有所述化合物。
5.一种显示器件或照明器件,其特征在于,包括如权利要求2至4中任一项所述的有机电子器件。
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