CN112174969A - 一种有机化合物、有机电致发光材料及有机电致发光元件 - Google Patents
一种有机化合物、有机电致发光材料及有机电致发光元件 Download PDFInfo
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- CN112174969A CN112174969A CN202011195763.8A CN202011195763A CN112174969A CN 112174969 A CN112174969 A CN 112174969A CN 202011195763 A CN202011195763 A CN 202011195763A CN 112174969 A CN112174969 A CN 112174969A
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- RMNIZOOYFMNEJJ-UHFFFAOYSA-K tripotassium;phosphate;hydrate Chemical compound O.[K+].[K+].[K+].[O-]P([O-])([O-])=O RMNIZOOYFMNEJJ-UHFFFAOYSA-K 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 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
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Abstract
Description
技术领域
本发明属于有机电致发光材料技术领域,具体涉及一种有机化合物、有机电致发光材料及有机电致发光元件。
背景技术
一般而言,有机发光现象是指在对有机物质施加电能时发出光的现象。即在阳极与阴极之间配置有机层时,如果在两个电极之间施加电压,则空穴会从阳极注入至有机层,电子会从阴极注入至有机层。当所注入的空穴和电子相遇时,会形成激子,当该激子跃迁至基态时,会发出光和热。
作为有效制造有机电致发光元件的一种方法,一直以来进行了以多层结构来代替单层制造元件内的有机层的研究,1987年唐提出了空穴层和发光层的功能层的层叠结构的有机电致发光元件,目前使用的大部分的有机电致发光元件包括:基板、阳极、从阳极接收空穴的空穴注入层、传输空穴的空穴传输层、空穴与电子进行再结合而发出光的发光层、传输电子的电子传输层、从阴极接收电子的电子注入层和阴极。这样以多层制作有机电致发光元件的理由是,由于空穴与电子的移动速度不同,因此如果制造适当的空穴注入层和传输层、电子传输层和电子注入层,则能够有效传输空穴和电子,元件内实现空穴与电子的均衡,能够提高激子利用率。
此外,作为以往的可应用于电子注入层和传输层的物质,报告了很多具有咪唑基、唑基、噻唑基、螺芴基的有机单分子物质。例如,中国专利CN103833507B、CN107573328B、CN107556310B以及由柯达公司于1996年发表的美国专利US5,645,948中记载的TPBI为具有咪唑基的电子传输层用物质,其结构中,在苯的1,3,5取代位置上含有三个N-苯基苯并咪唑基,就功能而言,不仅具有传输电子的能力,而且具有阻断从发光层跨越来的空穴的功能,但在实际应用在元件时存在热稳定性低的问题。
鉴于以上原因,特提出本发明。
发明内容
为了解决现有技术存在的以上问题,本发明提供了一种有机化合物、有机电致发光材料及有机电致发光元件,本发明所述的有机化合物作为发光材料可以提高发光元件的稳定性,出光效率和提高寿命等优点。
本发明的第一目的,提供了一种有机化合物,所述的化合物的结构式如式(I)所示:
其中,W1~W4彼此相同或不同,各自独立的选自CR1或N;
所述的R1选自氢、氘、卤素、氰基、硝基、C1-C40的烷基、C2-C40的烯基、C2-C40的炔基、C3-C40的环烷基、原子核数3至40的杂环烷基、C6-C60的芳基、C2-C60的杂芳基、C1-C40的烷氧基、C6-C60的芳氧基、C1-C40的烷基甲硅烷基、C6-C60的芳基甲硅烷基、C1-C40的烷基硼基、C6-C60的芳基硼基、C6-C60的芳基磷基、C6-C60的芳基氧化磷基、C6-C60的芳基胺基中的一种,当取代基R1为多个时,任意两个或多个相邻的取代基可以任选地接合或稠合、或键合至同一氮原子、磷原子、硼原子、氧或硫的桥连基彼此桥连,形成单环或稠环;
Ar1、Ar2、Ar3为单键、C6-C60的亚芳基或C2-C60的亚杂芳基;
Cy1、Cy2、Cy3各自独立地选C6-C60芳基或C2-C60杂芳基;
m、n、t表示0~5的整数;
Ar1、Ar2、Ar3中的亚芳基、亚杂芳基、Cy1、Cy2、Cy3中的芳基、杂芳基、以及R1中的烷基、烯基、炔基、环烷基、杂环烷基、芳基、杂芳基、烷氧基、芳氧基、烷基甲硅烷基、芳基甲硅烷基、烷基硼基、芳基硼基、芳基磷基、芳基氧化磷基和芳基胺基各自独立地被选自氘、卤原子、氰基、硝基、C1-C40的烷基、C2-C40的烯基、C2-C40的炔基、C3-C40的环烷基、C3-C40的杂环烷基、C6-C60的芳基、C2-C60的杂芳基、C1-C40的烷氧基、C6-C60的芳氧基、C1-C40的烷基甲硅烷基、C6-C60的芳基甲硅烷基、C1-C40的烷基硼基、C6-C60的芳基硼基、C6-C60的芳基磷基、C6-C60的芳基氧化磷基和C6-C60的芳基胺基中的一种,此时,当取代基为多个时,多个取代基可彼此相同或不同。
进一步的,所述的C2-C60的杂芳基为以下结构中的一种:
其中,Z1、Z2各自独立地选自氢、氘、卤原子、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C40烷基、C2-C40烯基、C2-C40炔基、C1-C40烷氧基、C3-C40环烷烃基、C3-C40环烯基、C6-C60芳基、C6-C60芳氧基、C6-C60的芳基硼基、C6-C60的芳基磷基、C6-C60的芳基氧化磷基、C6-C60的芳基胺基或C2-C60的杂芳基中的一种;
x1表示1-4的整数;x2表示1-3的整数;x3表示1或2;x4表示1-6的整数;x5表示1-5的整数;
T1表示氧、硫、CR2R3或NCy1;
所述R2和R3各自独立地选自氢、氘、C1-C40的烷基、C2-C40的烯基、C2-C40的炔基、C3-C40的环烷基、原子核数3至40的杂环烷基、C6-C60的芳基、C2-C60的杂芳基中的一种;
进一步的,Ar1、Ar2、Ar3为以下结构中的一种:
其中,Z11和Z12各自独立地选自氢、氘氢、卤原子、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C40烷基、C2-C40烯基、C2-C40炔基、C1-C40烷氧基、C3-C40环烷基、C3-C40环烯基、C6-C60芳基、C6-C60芳氧基、C6-C60的芳基硼基、C6-C60的芳基磷基、C6-C60的芳基氧化磷基、C6-C60的芳基胺基或C2-C60的杂芳基中的一种;
y1表示1-4的整数;y2表示1-6的整数;y3表示1-3的整数;y4表示1-5的整数;
T2表示氧、硫、CR2R3或NCy1;
所述R2和R3各自独立地选自氢、氘、C1-C40的烷基、C2-C40的烯基、C2-C40的炔基、C3-C40的环烷基、原子核数3至40的杂环烷基、C6-C60的芳基、C2-C60的杂芳基中的一种;
进一步的,W1~W4彼此相同或不同,各自独立地选自CR1或N,所述R1选自氢、氘、C1-C40的烷基、C6-C60的芳基、C2-C60的杂芳基中的一种。
进一步的,所述Cy1、Cy2、Cy3选自嘧啶、吡嗪、三嗪、咪唑、苯并咪唑、菲并咪唑、咪唑并吡啶、三唑并吡啶和喹唑啉中的一种;
所述嘧啶、吡嗪、三嗪、咪唑、苯并咪唑、菲并咪唑、咪唑并吡啶、三唑并吡啶和喹唑啉可各自独立地被氘、卤原子、氰基、硝基、C1-C40的烷基、C2-C40的烯基、C2-C40的炔基、C3-C40的环烷基、C3-C40的杂环烷基、C6-C60的芳基、C2-C60的杂芳基、C1-C40的烷氧基、C6-C60的芳氧基、C1-C40的烷基甲硅烷基、C6-C60的芳基甲硅烷基、C1-C40的烷基硼基、C6-C60的芳基硼基、C6-C60的芳基磷基、C6-C60的芳基氧化磷基和C6-C60的芳基胺基中的一种取代,此时,当取代基为多个时,多个取代基可彼此相同或不同。
根据本发明所述的有机化合物通过导入多种取代基R1、Cy1至Cy3、尤其是芳基和/或杂芳基,化合物的分子量显著增加,从而使玻璃化转变温度提高,由此与以往的发光材料相比能够具有更高的热稳定性。因此,能够使包含根据本发明的化合物的有机电致发光元件的性能和寿命特性大提高。如此性能和寿命特性提高的有机电致发光元件最终能够使全彩有机发光面板的性能最大化。
进一步的,所述的有机化合物为CJHP01~CJHP252中的一种,具体的结构式如下所示:
其中,T3为*—O—*、*—S—*或下述结构中的一种:
*—和—*表示连接键。
对于本发明意义上的烷基是指碳原子数从1至40的直链或带有支链的饱和烃去除氢原子而得到的一价官能团,作为其非限制性例子,如有甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-甲基丁基、正戊基、仲戊基、新戊基、环戊基、正己基、新己基、环己基、正庚基、环庚基、正辛基、环辛基、2-乙基己基等。
对于本发明意义上的烷氧基优选具有1至40个碳原子数的烷基氧基被认为是指甲氧基、三氟甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正戊氧基、仲戊氧基、2-甲基丁氧基、正己氧基、环己氧基、正庚氧基、环庚氧基、正辛氧基、环辛氧基、2-乙基己氧基、五氟乙氧基和2,2,2-三氟乙氧基等。
对于本发明意义上的杂烷基优选具有1至40个碳原子数的杂烷基,作为其非限制性例子,如有烷氧基、烷硫基、氟代的烷氧基、氟代的烷硫基,特别是指甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基、叔丁硫基、三氟甲硫基、三氟甲氧基、五氟乙氧基、五氟乙硫基、2,2,2-三氟乙氧基、2,2,2-三氟乙硫基、乙烯氧基、乙烯硫基、丙烯氧基、丙烯硫基、丁烯硫基、丁烯氧基、戊烯氧基、戊烯硫基、环戊烯氧基、环戊烯硫基、己烯氧基、己烯硫基、环己烯氧基、环己烯硫基、乙炔氧基、乙炔硫基、丙炔氧基、丙炔硫基、丁炔氧基、丁炔硫基、戊炔氧基、戊炔硫基、己炔氧基、己炔硫基。
一般来说,本发明的环烷基、环烯基优选具有3至40个碳原子数的环烷基、环烯基,作为其非限制性例子,如环丙基、环丁基、环戊基、环己基、降冰片基、金刚烷基、环丁烯基、环戊烯基、环己烯基、环庚基、环庚烯基、环辛烯基,其中一个或多个-CH2-基团可被上述基团代替;此外,一个或多个氢原子还可被氘原子、卤素原子或腈基代替。
根据本发明的杂环烷基是指从碳原子数3至40的非芳族烃去除氢原子而得到的一价官能团。此时,环中一个以上的碳、优选为1至3个碳被诸如氮、氧、或硫等杂原子取代,作为其非限制性例子,有吗啉、吡喃、哌嗪等。
根据本发明的烯基可为具有一个以上碳碳双键的碳原子数2至40的直链或支链的不饱和烃去除氢原子而得到的一价官能团。作为其非限制性例子,有乙烯基、烯丙基、异丙烯基、2-丁烯基、庚烯基、辛烯基等。
根据本发明的炔基是指具有一个以上碳碳三键的碳原子数2至40的直链或支链的不饱和烃去除氢原子而得到的一价官能团。作为其非限制性例子,有乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基或辛炔基等。
根据本发明的芳基是指从单环或组合了两个以上的碳原子数6至60的芳香烃去除氢原子而得到的一价官能团。此时,两个以上的环可以彼此附着或以缩合的形式附着。作为其非限制性的例子,有苯基、萘基、蒽基、苯并蒽基、菲基、芘基、基、苝基、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、三聚苯基、芴基、螺二芴基、二氢菲基、二氢芘基、四氢芘基、茚基、顺式或反式茚并芴基、顺式或反式茚并咔唑基、顺式或反式吲哚并咔唑基、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、吡咯基、吲哚基、异吲哚基、咔唑基、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、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、萘并噁唑基、蒽并噁唑基、菲并噁唑基、异噁唑基、1,2-噻唑基、1,3-噻唑基、苯并噻唑基、哒嗪基、六氮杂苯并菲基、苯并哒嗪基、嘧啶基、苯并嘧啶基、喹喔啉基、1,5-二氮杂蒽基、2,7-二氮杂芘基、2,3-二氮杂芘基、1,6-二氮杂芘基、1,8-二氮杂芘基、4,5-二氮杂芘基,4,5,9,10-四氮杂苝基、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、咔啉基、菲咯啉基、1,2,3-三唑基、1,2,4-三唑基、苯并三唑基、1,2,3-噁二唑基、1,2,4-噁二唑基、1,2,5-噁二唑基、1,3,4-噁二唑基、1,2,3-噻二唑基、1,2,4-噻二唑基、1,2,5-噻二唑基、1,3,4-噻二唑基、1,3,5-三嗪基、1,2,4-三嗪基、1,2,3-三嗪基、四唑基、1,2,4,5-四嗪基、1,2,3,4-四嗪基、1,2,3,5-四嗪基、嘌呤基、蝶啶基、吲嗪基和苯并噻二唑基或者衍生自这些体系的组合的基团。
本发明的芳氧基、芳基硼基、芳基磷基和芳基氧化磷基是指碳原子数6至60的芳基与氧原子、硼原子、磷原子、氧化磷、氮原子连接的一价官能团。作为非限制性例子,有苯氧基、萘氧基、二苯氧基、二苯硼基、二苯磷基、二苯氧化磷基、二苯胺基等。
本发明的烷基甲硅烷基是指被碳原子数1至40的烷基取代的甲硅烷基,芳基甲硅烷基是指被碳原子数6至60的芳基取代的甲硅烷基,芳基胺是指被碳原子数6至60的芳基取代的胺。
本发明的亚芳基、亚杂芳基是指上述的碳原子数6至60的芳基、碳原子数2至60的杂芳基去除氢原子而得到的二价官能团。此时,作为其非限制性例子,如有亚苯基、亚萘基、亚联苯基、亚吡啶基等。
本发明的第二目的,提供了一种有机电致发光材料,所述的材料包含所述的有机化合物。
本发明的第三目的,提供了一种有机电致发光元件,包括第一电极、第二电极和置于所述的第一电极和所述的第二电极之间的一层以上的有机层,所述的有机层包含所述的有机化合物。
所述有机电致发光元件包含阴极、阳极和至少一个发光层。除了这些层之外,它还可以包含其它的层,例如在每种情况下,包含一个或多个空穴注入层、空穴传输层、空穴阻挡层、电子传输层、电子注入层、激子阻挡层、电子阻挡层和/或电荷产生层。其中,包含上述式I所示化合物的有机层优选为发光层、电子传输层和在电子传输层上进一步层叠的电子传输辅助层。此时,上述化学式I所示的化合物可用作上述发光层的主体物质或电子传输层和电子传输辅助层物质。然而,应当指出,这些层中的每个并非必须都存在。此处所述有机电致发光元件可包含一个发光层,或者它可包含多个发光层。即,将能够发光的多种发光化合物用于所述发光层中。特别优选具有三个发光层的体系,其中所述三个层可显示蓝色、绿色和红色发光。如果存在多于一个的发光层,则根据本发明,这些层中的至少一个层包含本发明的化合物。
本发明提供包含上述式(I)所示的化合物的有机电致发光元件。具体而言,根据本发明的有机电致发光元件包含第一电极、第二电极以及介于所述第一电极、所述第二电极之间的一层以上的有机层,上述一层以上的有机层中,至少一层包含上述式I所示的化合物。此时,上述化合物可以单独使用、或者两种以上混合使用。上述一层以上的有机层可以为空穴注入层、空穴传输层、发光层、电子传输层和电子注入层中的任意一种以上。优选地,包含上述化学式I的化合物的有机层可以为发光层、电子传输层和在电子传输层上进一步层叠的电子辅助层,更优选地,可以为电子传输层和电子传输辅助层。
根据本发明的有机电致发光元件的发光层可以包含主体材料,此时,作为主体材料,可以包含上述式(I)的化合物。这样的发光层包含上述式(I)所示的化合物的情况下,空穴传输能力增加,在发光层中空穴与电子的结合机会变高,因此能够提供效率、寿命、亮度和驱动电压优异的有机电致发光元件。此外,本发明的有机电致发光元件的发光层可以包含上述式(I)所示的化合物之外的化合物作为主体。
本发明的有机电致发光元件的电子传输层可以包含电子传输材料,此时,可以包含上述式(I)所示的化合物。电子传输层在包含上述式(I)所示的化合物的情况下,因两个吸电子基团而使电子传输能力增强,能够顺利地将所注入的电子输送于发光层,因此能够提供效率、寿命、亮度和驱动电压等优异的有机电致发光元件。其中,在上述电子传输层上可以进一步层叠电子传输辅助层。这样在传输辅助层中包含上述式I所示的化合物的情况下,因高的三重态能级而防止激子从发光层和电子传输层跃迁的效果,因此尤其能够改善蓝色有机电致发光元件的效率、寿命和驱动电压等。
本发明的有机电致发光元件的结构没有特别限定,作为非限制性例子,如附图1、图2,可以为依次层叠有基板、阳极、空穴注入层、空穴传输层、电子阻挡层、发光层、电子传输层和阴极的结构。其中,在上述电子传输层上可以进一步层叠有电子注入层,在上述发光层上还可以层叠空穴阻挡层。此外,本发明的有机电致发光元件的结构可以为电极与有机层之间插入有绝缘层或粘接层的结构。
在本发明的描述中,除非另有说明,“多个”的含义是两个或两个以上;术语“上”、“下”等指示的方位或位置关系为基于附图所示的方位或位置关系,仅是为了便于描述本发明和简化描述,而不是指示或暗示所指的装置或元件必须具有特定的方位、以特定的方位构造和操作,因此不能理解为对本发明的限制。
进一步的,所述的有机层为发光层、电子传输层、电子注入层、电子传输辅助层或电子阻挡层。
进一步的,所述的有机化合物为发光层的主体物质。
本发明中的有机电致发光元件不包含单独的空穴注入层和/或空穴传输层和/或空穴阻挡层和/或电子传输层和/或电子注入层,即发光层与空穴注入层或阳极直接相邻,和/或发光层与电子传输层或电子注入层或阴极直接相邻。
在根据本发明的有机电致发光器件的其它层中,特别是在空穴注入层和空穴传输层中以及在电子注入和电子传输层中,所有材料可以按照根据现有技术通常所使用的方式来使用。本领域普通技术人员因此将能够在不付出创造性劳动的情况下与根据本发明的发光层组合使用关于有机电致发光元件所知的所有材料。
此外优选如下的有机电致发光装置,其特征在于借助于升华方法施加一个或多个层,其中在真空升华装置中在低于10-5Pa、优选低于10-6Pa的初压下通过气相沉积来施加所述材料。然而,所述初压还可能甚至更低,例如低于10-7Pa。
同样优选如下的有机电致发光元件,借助于有机气相沉积方法或借助于载气升华来施加一个或多个层,其中,在10-5Pa至1Pa之间的压力下施加所述材料。该方法的特别的例子是有机蒸气喷印方法,其中所述材料通过喷嘴直接施加,因此是结构化的。
此外优选如下的有机电致发光元件,从溶液中,例如通过旋涂,或借助于任何所希望的印刷方法例如丝网印刷、柔性版印刷、平版印刷、光引发热成像、热转印、喷墨印刷或喷嘴印刷,来产生一个或多个层。可溶性化合物,例如通过适当的取代获得可溶性化合物。这些方法也特别适于低聚物、树枝状大分子和聚合物。此外可行的是混合方法,其中例如从溶液中施加一个或多个层并且通过气相沉积施加一个或多个另外的层。
这些方法是本领域普通技术人员通常已知的,并且他们可以在不付出创造性劳动的情况下将其应用于包含根据本发明的化合物的有机电致发光元件。
因此,本发明还涉及制造根据本发明的有机电致发光元件的方法,借助于升华方法来施加至少一个层,和/或特征在于借助于有机气相沉积方法或借助于载气升华来施加至少一个层,和/或特征在于从溶液中通过旋涂或借助于印刷方法来施加至少一个层。
此外,本发明涉及包含至少一种上文指出的本发明的化合物。如上文关于有机电致发光元件指出的相同优选情况适用于所述本发明的化合物。特别是,所述化合物此外还可优选包含其它化合物。从液相处理根据本发明的化合物,例如通过旋涂或通过印刷方法进行处理,需要根据本发明的化合物的制剂。这些制剂可以例如是溶液、分散体或乳液。出于这个目的,可优选使用两种或更多种溶剂的混合物。合适并且优选的溶剂例如是甲苯,苯甲醚,邻二甲苯、间二甲苯或对二甲苯,苯甲酸甲酯,均三甲苯,萘满,邻二甲氧基苯,四氢呋喃,甲基四氢呋喃,四氢吡喃,氯苯,二噁烷,苯氧基甲苯,特别是3-苯氧基甲苯,(-)-葑酮,1,2,3,5-四甲基苯,1,2,4,5-四甲基苯,1-甲基萘,2-甲基苯并噻唑,2-苯氧基乙醇,2-吡咯烷酮,3-甲基苯甲醚,4-甲基苯甲醚,3,4-二甲基苯甲醚,3,5-二甲基苯甲醚,苯乙酮,α-萜品醇,苯并噻唑,苯甲酸丁酯,异丙苯,环己醇,环己酮,环己基苯,十氢化萘,十二烷基苯,苯甲酸乙酯,茚满,苯甲酸甲酯,1-甲基吡咯烷酮,对甲基异丙基苯,苯乙醚,1,4-二异丙基苯,二苄醚,二乙二醇丁基甲基醚,三乙二醇丁基甲基醚,二乙二醇二丁基醚,三乙二醇二甲基醚,二乙二醇单丁基醚,三丙二醇二甲基醚,四乙二醇二甲基醚,2-异丙基萘,戊苯,己苯,庚苯,辛苯,1,1-双(3,4-二甲基苯基)乙烷,或这些溶剂的混合物。
另外,如无特殊说明,本发明中所用原料均可通过市售商购获得,本发明所记载的任何范围包括端值以及端值之间的任何数值以及端值或者端值之间的任意数值所构成的任意子范围。
与现有技术相比,本发明的有益效果为:
本发明所述的有机化合物用于制备有机电致发光元件时,电子移动性、热稳定性和发光特性优异,可以应用于有机电致发光元件的有机层,本发明所述的有机化合物具有较好的成膜性,其应用于电子传输层和电子传输辅助层时,能够制造与以往的电子传输材料相比具有更低的驱动电压、更高的出光效率以及更长寿命的有机电致发光元件,进而还能够制造性能和寿命提高的全彩显示器面板。
附图说明
为了更清楚地说明本发明实施例或现有技术中的技术方案,下面将对实施例或现有技术描述中所需要使用的附图作简单地介绍,显而易见地,下面描述中的附图仅仅是本发明的一些实施例,对于本领域普通技术人员来讲,在不付出创造性劳动的前提下,还可以根据这些附图获得其他的附图。
图1是本发明的有机电致发光装置的一个底部发光例子的示意图;
图2是本发明的有机电致发光装置的一个顶部发光例子的示意图。
附图标记
1-基板、2-阳极、3-空穴注入层、4-空穴传输层/电子阻挡层、5-发光层、6-空穴阻挡/电子传输层、7-电子注入层、8-阴极。
具体实施方式
为使本发明的目的、技术方案和优点更加清楚,下面将对本发明的技术方案进行详细的描述。显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动的前提下所得到的所有其它实施方式,都属于本发明所保护的范围。
以下实施例对OLED材料及器件进行性能测试,测试的仪器和方法如下:
OLED器件性能检测条件:
亮度和色度坐标:使用光谱扫描仪PhotoResearch PR-715测试;
电流密度和起亮电压:使用数字源表Keithley 2420测试;
功率效率:使用NEWPORT 1931-C测试。
实施例1
化合物CJHP07的制备方法,包括如下步骤:
第一步:中间体Int-1的制备
10.0mmol的邻苯二甲醛、10.0mmol的苯甘氨醇和20.0mmol的苯并三氮唑,再加入50mL的二氯甲烷,再加入10.0g的分子筛,于室温搅拌反应10小时,过滤,滤液用2mol/L的氢氧化钠水溶液洗、饱和食盐水洗,收集有机相,干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得深褐色固体Int-1,收率59%。
59%。
第二步:中间体Int-2的制备
15.0mmol的中间体Int-1溶解在100mL甲醇中,加入0.1mol的甲酸铵和0.1g的钯/炭,室温搅拌反应8小时,过滤,滤液减压浓缩干,加入100mL二氯甲烷溶解,用水洗两次,收集有机相干燥,过滤,向滤液内加入2.5g的三乙胺,缓慢滴加16.5mmol的苯甲酰氯,搅拌反应2小时,加入20mL的10%氢氧化钠水溶液,分出有机相,再用饱和食盐水洗、水洗,有机相干燥,过滤,减压浓缩干,用硅胶柱分离纯化,得到黄色固体Int-2,收率:78%。
第三步:中间体Int-3的制备
10.0mmol的中间体Int-2与35.0g的尿素混合,升温到150℃搅拌反应2小时,冷却到80℃时,加入100mL的10%氢氧化钠水溶液,搅拌30分钟,过滤,滤饼用水洗,得黄色固体Int-3,收率83%。
第四步:中间体Int-4的制备
10.0mmol的中间体Int-3溶解于40mL的三氯氧磷中,升温至回流搅拌反应8小时,冷却到室温,将反应液倒入200mL的冰/水中,过滤,滤饼用水洗,用硅胶柱分离纯化,得黄色固体Int-4,收率76%。
第五步:中间体Int-5的制备
9.5mmol的苯硼酸、8.6mmol的中间体Int-4、3.7g(34.9mmol)的碳酸钠和5mg的Pd(PPh3)4催化剂,加入40mL的甲苯和10mL的乙醇以及5mL的水,升温回流搅拌反应12小时,冷却到室温,用乙酸乙酯萃取,有机相干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得黄色固体Int-5,收率84%。
第六步:中间体Int-6的制备
10.0mmol的中间体Int-5溶解于80mL的二氯甲烷中,用冰水浴降温至10℃,分批加入11.0mmol的NBS,搅拌反应2小时,加入80mL的水,分出有机相,干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得黄色固体Int-6,收率96%。
第七步:化合物CJHP07的制备
10.2mmol的(4’-(4,6-二苯基-1,3,5-三嗪-2-基)-[1,1’-联苯]-4-基)硼酸、8.5mmol的中间体Int-6、3.6g(34.0mmol)的碳酸钠和5mg的Pd(PPh3)4催化剂,加入40mL的甲苯和10mL的乙醇以及10mL的水,升温回流搅拌反应12小时,冷却到室温,用乙酸乙酯萃取,有机相干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,再用乙醇加热至沸腾,趁热过滤,得4.9g的产物CJHP07,收率82.4%。
MS(MALDI-TOF):m/z 705.2782[M+H]+;1HNMR(δ、CDCl3):8.77~8.75(4H,m);8.51~8.48(7H,m);8.03~8.01(4H,m);7.92~7.90(2H,m);7.72~7.70(3H,m);7.56~7.45(10H,m);7.38~7.35(2H,m)。
实施例2
化合物CJHP01~CJHP06、CJHP08~CJHP48、CJHP103~CJHP107的制备参照实施例1中化合物CJHP07的合成方法,不同之处在于,根据实际需要采用不同的化合物替换实施例1第七步中的(4’-(4,6-二苯基-1,3,5-三嗪-2-基)-[1,1’-联苯]-4-基)硼酸,并根据摩尔量更改该化合物的质量用量,其他实验参数根据实际需要进行相应的调整。
实施例3
化合物CJHP63的制备,包括如下步骤:
第一步:中间体Int-7的制备
10.0mmol实施例1第四步制备的中间体Int-4溶解于80mL的二氯甲烷中,用冰水浴降温至0℃,分批加入11.0mmol的NBS,搅拌反应2小时,加入80mL的水,分出有机相,干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得黄色固体Int-7,收率94%。
第二步:中间体Int-8的制备
11.0mmol的苯硼酸、10.0mmol的中间体Int-7、2.4g(22.0mmol)的碳酸钠和5mg的Pd(PPh3)4催化剂,加入50mL的甲苯和20mL的乙醇以及20mL的水,升温回流搅拌反应12小时,冷却到室温,用乙酸乙酯萃取,有机相干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得黄色固体Int-8,收率75%。
第三步:化合物CJHP63的制备
9.5mmol的(4’-(4,6-二苯基-1,3,5-三嗪-2-基)-[1,1’-联苯]-4-基)硼酸、8.6mmol的中间体Int-8、3.7g(34.9mmol)的碳酸钠和5mg的Pd(PPh3)4催化剂,加入40mL的甲苯和10mL的乙醇以及5mL的水,升温回流搅拌反应12小时,冷却到室温,用乙酸乙酯萃取,有机相干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,再用乙醇加热至沸腾,趁热过滤,得4.4g的产物CJHP63,收率72.5%。
MS(MALDI-TOF):m/z 705.2786[M+H]+;1HNMR(δ、CDCl3):8.82~8.80(4H,m);8.51~8.48(5H,m);8.37~8.35(2H,m);7.92~7.88(6H,m);7.73~7.68(5H,m);7.53~7.45(8H,m);7.36~7.34(2H,m)。
实施例4
化合物CJHP49~CJHP62、CJHP64~CJHP102的制备,制备方法同实施例3化合物CJHP6,不同之处在于,根据实际需要采用不同的化合物替换实施例3第三步中的(4’-(4,6-二苯基-1,3,5-三嗪-2-基)-[1,1’-联苯]-4-基)硼酸,并根据摩尔量更改该化合物的质量用量,其他实验参数根据实际需要进行相应的调整。
实施例5
化合物CJHP133的制备,包括如下步骤:
第一步:中间体Int-11的制备
11.0mmol的五溴化磷、10.0mmol的中间体Int-10(参照实施例1的第一至第三步,仅将第二步中的苯甲酰氯替换为对氯苯甲酰氯制备获得)和60mL的甲苯,升温回流搅拌反应6小时,冷却到室温,减压浓缩干,向残余物内加入碎冰,搅拌过滤,滤饼用水洗,得中间体Int-11,黄色固体,收率85%。
第二步:中间体Int-12的制备
10.0mmol的中间体Int-11溶解于100mL的二氯甲烷中,分批加入11.0mmol的NBS,搅拌反应5小时,加入80mL的水,分出有机相,干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得黄色固体Int-12,收率93%。
第三步:中间体Int-13的制备
17.6mmol的苯硼酸、8.0mmol的中间体Int-12、3.8g(36.0mmol)的碳酸钠和138.6mg的Pd(PPh3)4催化剂,加入80mL的甲苯和40mL的乙醇以及40mL的水,升温回流搅拌反应12小时,冷却到室温,加入20mL的水稀释,用乙酸乙酯萃取,有机相干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得化合物Int-13,收率79%。
第四步:化合物CJHP133的制备
9.6mmol的(4-(2,6-二苯基嘧啶-4-基)苯基)硼酸、8.0mmol的中间体Int-13、5.5g(16.0mmol)的水合磷酸钾和185.0mg的Pd(PPh3)4催化剂,加入80mL的甲苯和40mL的乙醇以及40mL的水,升温回流搅拌反应12小时,冷却到室温,加入20mL的水稀释,用二氯甲烷萃取,有机相干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得化合物CJHP133,收率83%。
MS(MALDI-TOF):m/z 704.2832[M+H]+;1HNMR(δ、CDCl3):8.33~8.26(7H,m);8.24~8.20(4H,m);8.03~8.02(2H,m);7.94~7.90(2H,m);7.76~7.65(9H,m);7.57~7.32(18H,m)。
实施例6
化合物CJHP108~CJHP132、CJHP134~CJHP163的制备同实施例5中化合物CJHP133的方法,不同之处在于,根据实际需要采用不同的化合物替换实施例5第四步中的(4-(2,6-二苯基嘧啶-4-基)苯基)硼酸,并根据摩尔量更改该化合物的质量用量,其他实验参数根据实际需要进行相应的调整。
实施例7
化合物CJHP167的制备,包括如下步骤:
第一步:中间体Int-14的制备
在氮气保护下,15.0mmol的中间体Int-6溶解于80mL的干燥四氢呋喃中,用液氮降温至-80℃,滴加入7.2mL的2.5M正丁基锂正己烷溶液,搅拌反应30分钟,滴加入20.0mmol硼酸三甲酯溶于无水四氢呋喃的溶液,搅拌反应1小时,升至室温,加入20mL的2N稀盐酸,搅拌反应1小时,用乙酸乙酯萃取,收集有机相,干燥,过滤,滤液减压浓缩干,加入石油醚分散过滤,得到中间体Int-14,收率80%。
第二步:化合物CJHP167的制备
10.0mmol的2-([1,1'-联苯]-4-基)-4-氯-6-苯基-1,3,5-三嗪、12.0mmol的中间体Int-14、3.2g(30.0mmol)的碳酸钠和11.5mg的Pd(PPh3)4催化剂,加入40mL的甲苯和10mL的乙醇以及10mL的水,升温回流搅拌反应12小时,冷却到室温,用乙酸乙酯萃取,有机相干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,再用二氯甲烷-乙醇重结晶,得到产物CJHP167,收率76%。
MS(MALDI-TOF):m/z 629.2472[M+H]+;1HNMR(δ、CDCl3):8.84~8.82(2H,d);8.62~8.59(3H,m);8.43~8.41(4H,m);7.92~7.89(3H,m);7.72~7.69(2H,m);7.58~7.52(6H,m);7.42~7.23(8H,m)。
实施例8
化合物CJHP164~CJHP166、CJHP168~CJHP173的制备,制备方法同实施例7中化合物CJHP167,不同之处在于,根据实际需要采用不同的化合物替换实施例7中第二步中的2-([1,1'-联苯]-4-基)-4-氯-6-苯基-1,3,5-三嗪,并根据摩尔量更改该化合物的质量用量,其他实验参数根据实际需要进行相应的调整。
实施例9
化合物CJHP176(T3=O)的制备:
在氮气保护下,11.0mmol的中间体Int-6、10.0mmol的苯并[c]苯并呋喃[2,3-a]咔唑、1.5g的叔丁醇钠和0.21g的碘化亚铜、0.7mg的Pd2(dba)3CHCl3以及0.1mL的10%三叔丁基磷甲苯溶液,再加入60mL干燥的甲苯,升温至100℃搅拌反应12小时,冷却到室温,加入20mL水稀释,用乙酸乙酯萃取,有机相干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,再用二氯甲烷-四氢呋喃重结晶,得到产物CJHP176,收率86%。
MS(MALDI-TOF):m/z 627.2171[M+H]+;1HNMR(δ、CDCl3):8.59~8.57(2H,d);8.52~8.45(6H,m);8.30~8.28(3H,m);7.89~7.88(1H,m);7.74~7.72(2H,m);7.64~7.58(4H,m);7.56~7.54(3H,m);7.52~7.47(3H,m);7.42~7.39(1H,m);7.35~7.33(1H,m)。
实施例10
化合物CJHP174、CJHP175、CJHP177~CJHP189、CJHP209~CJHP243的制备,制备方法同实施例9中化合物CJHP176,不同之处在于,根据实际需要采用不同的化合物替换实施例9中的中间体中间体Int-6和苯并[c]苯并呋喃[2,3-a]咔唑,并根据摩尔量更改该化合物的质量用量,其他实验参数根据实际需要进行相应的调整。
实施例11
化合物CJHP204的制备:
在氮气保护下,10.0mmol的二苯并[c,g]咔唑溶解于60mL的N,N-二甲基甲酰胺中,用冰水浴降温至0℃,分批加入11.0mmol的65%氢化钠油分散固体,搅拌反应1小时,加入12.0mmol的中间体Int-8固体,搅拌反应2小时,升到室温搅拌反应12小时,将反应液倒入200mL的冰水中,过滤,滤饼用水洗,用硅胶柱分离纯化,得到产物CJHP204,收率87%。
MS(MALDI-TOF):m/z 587.2251[M+H]+;1HNMR(δ、CDCl3):8.49~8.46(5H,m);8.15~8.13(4H,d);7.98~7.97(2H,m);7.92~7.90(2H,m);7.68~7.59(9H,m);7.48~7.44(2H,m);7.35~7.33(2H,m)。
实施例12
化合物CJHP190~CJHP203、CJHP205~CJHP208的制备,制备方法同实施例11中化合物CJHP204,不同之处在于,根据实际需要采用不同的化合物替换实施例11中的二苯并[c,g]咔唑,并根据摩尔量更改该化合物的质量用量,其他实验参数根据实际需要进行相应的调整。
实施例13
化合物CJHP244的制备:
9.6mmol的2-苯并菲基硼酸、8.0mmol的中间体Int-15(参照实施例5中第一至第三的合成方法制备)、2.2g(20.0mmol)的碳酸钠和92.4mg的Pd(PPh3)4催化剂,加入60mL的甲苯和30mL的乙醇以及20mL的水,升温回流搅拌反应12小时,冷却到室温,加入20mL的水稀释,用二氯甲烷萃取,有机相干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得化合物CJHP244,收率78%。
MS(MALDI-TOF):m/z 624.2425[M+H]+;1HNMR(δ、CDCl3):9.21(1H,s);8.75~8.69(4H,m);8.35~8.31(5H,m);8.26~8.25(1H,d);7.96~7.95(1H,d);7.83~7.79(3H,m);7.70~7.63(7H,m);7.59~7.55(3H,m);7.51~7.48(2H,m);7.44~7.38(2H,m)。
实施例14
化合物CJHP245~CJHP252制备,制备方法同实施例13中化合物CJHP244,不同之处在于,根据实际需要采用不同的化合物替换实施例13中的2-苯并菲基硼酸,并根据摩尔量更改该化合物的质量用量,其他实验参数根据实际需要进行相应的调整。
试验例1
将实施例1-14制备的化合物进行升华精制后,制成有机电致发光元件,具体制备方法如下:
(1)将涂布有ITO的玻璃基片用蒸馏水超声波洗涤,用异丙醇、丙酮/乙醇混合溶剂超声波洗涤,在洁净的环境下烘烤至完全干燥,用紫外光清洗机照射10分钟,然后利用UV将上述的基片清洗5分钟,将基片转移至真空蒸镀机。
(2)把上述处理好的ITO电极上,依次层叠HT002(八亿时空,/HT022(八亿时空,/HT001(八亿时空,/ADN+5%DA021(八亿时空,/CJHP01~CJHP252各个化合物制作有机电致发光元件。
对比例1
作为电子传输层物质,使用Alq3(8-羟基喹啉铝)代替化合物CJHP01~CJHP252,除比之外,与试验例1相同地操作,制备有机电致发光元件。
对比例2
作为电子传输层物质,不使用化合物CJHP01~CJHP252,除比之外,与试验例1相同地操作,制备有机电致发光元件。
其中,AND和Alq3的结构式如下所示:
对于试验例1和对比例1-2制备的有机电致发光元件,测定测定电流密度10mA/cm2时的驱动电压、电流效率、发光峰,部分化合物及对比例1-2制备的有机电致发光元件的测试结果示如表1所示。
表1
从表1中可以看出,将本发明制备的化合物用于电子传输层的有机电致发光元件与Alq3用于电子传输层的有机电致发光元件和没有电子传输层的有机电致发光元件相比,在驱动电压、电流效率和发光最强峰方面显示优异的性能。
其他化合物的测试结果与表1数据基本一致,由于篇幅有限,不再一一列举。
试验例2
分别将实施例1-14制备的化合物进行升华精制,制作如下有机电致发光元件。
(1)将涂布有ITO的玻璃基片用蒸馏水超声波洗涤,用异丙醇、丙酮/乙醇混合溶剂超声波洗涤,在洁净的环境下烘烤至完全干燥,用紫外光清洗机照射10分钟,然后利用UV将上述的基片清洗5分钟,将基片转移至真空蒸镀机。
(2)把上述处理好的ITO电极上,依次层叠HT002(八亿时空,/HT022(八亿时空,/HT001(八亿时空,/CJHP01~CJHP252各个化合物+2%RD018(八亿时空, 制作有机电致发光元件。
对比例3
作为发光层的主体物质,使用RH03代替化合物CJHP01~CJHP252,除比之外,与试验例2同样地操作,制备有机电致发光元件。
所述RH03的结构如下:
对于试验例2和对比例3分别制作的有机电致发光元件,测定电流密度10mA/cm2时的驱动电压、电流效率、发光峰,部分化合物与对比例3的结果如表2所示。
表2
从表2可以看出,将本发明的化合物用于发光层主体的有机电致发光元件与RH03用于发光层主体的有机电致发光元件相比,在驱动电压、电流效率和发光最强峰方面显示优异的性能。
其他化合物的测试结果与表2数据基本一致,由于篇幅有限,不再一一列举。
综上分析,利用本发明的化合物制备的有机电致发光元件可以在手机、壁挂电视、平板显示器、照明等的平面发光体、复印机、打印机、液晶显示器的背光源或计量仪器类等的光源,显示板、标识灯等中应用。
以上所述,仅为本发明的具体实施方式,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,可轻易想到变化或替换,都应涵盖在本发明的保护范围之内。因此,本发明的保护范围应以所述权利要求的保护范围为准。
Claims (10)
1.一种有机化合物,其特征在于,所述的化合物的结构式如式(I)所示:
其中,W1~W4彼此相同或不同,各自独立的选自CR1或N;
所述的R1选自氢、氘、卤素、氰基、硝基、C1-C40的烷基、C2-C40的烯基、C2-C40的炔基、C3-C40的环烷基、原子核数3至40的杂环烷基、C6-C60的芳基、C2-C60的杂芳基、C1-C40的烷氧基、C6-C60的芳氧基、C1-C40的烷基甲硅烷基、C6-C60的芳基甲硅烷基、C1-C40的烷基硼基、C6-C60的芳基硼基、C6-C60的芳基磷基、C6-C60的芳基氧化磷基、C6-C60的芳基胺基中的一种,当取代基R1为多个时,任意两个或多个相邻的取代基可以任选地接合或稠合、或键合至同一氮原子、磷原子、硼原子、氧或硫的桥连基彼此桥连,形成单环或稠环;
Ar1、Ar2、Ar3为单键、C6-C60的亚芳基或C2-C60的亚杂芳基;
Cy1、Cy2、Cy3各自独立地选C6-C60芳基或C2-C60杂芳基;
m、n、t表示0~5的整数;
Ar1、Ar2、Ar3中的亚芳基、亚杂芳基、Cy1、Cy2、Cy3中的芳基、杂芳基、以及R1中的烷基、烯基、炔基、环烷基、杂环烷基、芳基、杂芳基、烷氧基、芳氧基、烷基甲硅烷基、芳基甲硅烷基、烷基硼基、芳基硼基、芳基磷基、芳基氧化磷基和芳基胺基各自独立地被选自氘、卤原子、氰基、硝基、C1-C40的烷基、C2-C40的烯基、C2-C40的炔基、C3-C40的环烷基、C3-C40的杂环烷基、C6-C60的芳基、C2-C60的杂芳基、C1-C40的烷氧基、C6-C60的芳氧基、C1-C40的烷基甲硅烷基、C6-C60的芳基甲硅烷基、C1-C40的烷基硼基、C6-C60的芳基硼基、C6-C60的芳基磷基、C6-C60的芳基氧化磷基和C6-C60的芳基胺基中的一种,此时,当取代基为多个时,多个取代基可彼此相同或不同。
2.根据权利要求1所述的有机化合物,其特征在于,所述的C2-C60的杂芳基为以下结构中的一种:
其中,Z1、Z2各自独立地选自氢、氘、卤原子、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C40烷基、C2-C40烯基、C2-C40炔基、C1-C40烷氧基、C3-C40环烷烃基、C3-C40环烯基、C6-C60芳基、C6-C60芳氧基、C6-C60的芳基硼基、C6-C60的芳基磷基、C6-C60的芳基氧化磷基、C6-C60的芳基胺基或C2-C60的杂芳基中的一种;
x1表示1-4的整数;x2表示1-3的整数;x3表示1或2;x4表示1-6的整数;x5表示1-5的整数;
T1表示氧、硫、CR2R3或NCy1;
所述R2和R3各自独立地选自氢、氘、C1-C40的烷基、C2-C40的烯基、C2-C40的炔基、C3-C40的环烷基、原子核数3至40的杂环烷基、C6-C60的芳基、C2-C60的杂芳基中的一种;
3.根据权利要求1所述的有机化合物,其特征在于,Ar1、Ar2、Ar3为以下结构中的一种:
其中,Z11和Z12各自独立地选自氢、氘氢、卤原子、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C40烷基、C2-C40烯基、C2-C40炔基、C1-C40烷氧基、C3-C40环烷基、C3-C40环烯基、C6-C60芳基、C6-C60芳氧基、C6-C60的芳基硼基、C6-C60的芳基磷基、C6-C60的芳基氧化磷基、C6-C60的芳基胺基或C2-C60的杂芳基中的一种;
y1表示1-4的整数;y2表示1-6的整数;y3表示1-3的整数;y4表示1-5的整数;
T2表示氧、硫、CR2R3或NCy1;
所述R2和R3各自独立地选自氢、氘、C1-C40的烷基、C2-C40的烯基、C2-C40的炔基、C3-C40的环烷基、原子核数3至40的杂环烷基、C6-C60的芳基、C2-C60的杂芳基中的一种;
4.根据权利要求1所述的有机化合物,其特征在于,W1~W4彼此相同或不同,各自独立地选自CR1或N,所述R1选自氢、氘、C1-C40的烷基、C6-C60的芳基、C2-C60的杂芳基中的一种。
5.根据权利要求1-4任意一项所述的有机化合物,其特征在于,所述Cy1、Cy2、Cy3选自嘧啶、吡嗪、三嗪、咪唑、苯并咪唑、菲并咪唑、咪唑并吡啶、三唑并吡啶和喹唑啉中的一种;
优选的,所述嘧啶、吡嗪、三嗪、咪唑、苯并咪唑、菲并咪唑、咪唑并吡啶、三唑并吡啶和喹唑啉可各自独立地被氘、卤原子、氰基、硝基、C1-C40的烷基、C2-C40的烯基、C2-C40的炔基、C3-C40的环烷基、C3-C40的杂环烷基、C6-C60的芳基、C2-C60的杂芳基、C1-C40的烷氧基、C6-C60的芳氧基、C1-C40的烷基甲硅烷基、C6-C60的芳基甲硅烷基、C1-C40的烷基硼基、C6-C60的芳基硼基、C6-C60的芳基磷基、C6-C60的芳基氧化磷基和C6-C60的芳基胺基中的一种取代,此时,当取代基为多个时,多个取代基可彼此相同或不同。
7.一种有机电致发光材料,其特征在于,所述的材料包含权利要求1-6任意一项所述的有机化合物。
8.一种有机电致发光元件,包括第一电极、第二电极和置于所述的第一电极和所述的第二电极之间的一层以上的有机层,其特征在于,所述的有机层包含权利要求1-6任意一项所述的有机化合物。
9.根据权利要求8所述的有机电致发光元件,其特征在于,所述的有机层为发光层、电子传输层、电子注入层、电子传输辅助层或电子阻挡层。
10.根据权利要求9所述的有机电致发光元件,其特征在于,所述的有机化合物为发光层的主体物质。
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