CN113912636B - 含硅杂环化合物和含有该化合物的有机电致发光元件 - Google Patents
含硅杂环化合物和含有该化合物的有机电致发光元件 Download PDFInfo
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- CN113912636B CN113912636B CN202111322300.8A CN202111322300A CN113912636B CN 113912636 B CN113912636 B CN 113912636B CN 202111322300 A CN202111322300 A CN 202111322300A CN 113912636 B CN113912636 B CN 113912636B
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- 239000010703 silicon Substances 0.000 title claims abstract description 30
- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 29
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- 239000010410 layer Substances 0.000 claims description 116
- 239000000463 material Substances 0.000 claims description 41
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- 238000002360 preparation method Methods 0.000 claims description 33
- 238000002347 injection Methods 0.000 claims description 26
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
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- 230000005525 hole transport Effects 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 239000012044 organic layer Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
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- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
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- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
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Abstract
本发明公开了一种含硅杂环化合物和含有该化合物的有机电致发光元件,其结构通式如式I所示。多元杂环的引入不仅增大分子的电子云密度,同时增大了分子共轭面积提高内量子效率,含硅基团的加入与以住的化合物相比具有更短的发光波长和更窄的峰宽。同时,该含硅杂环化合物阻碍有机分子间激‑激复合物的生成、增加内部电子密度和稳定性,由此得以提高包含该化合物的有机电致发光器件的效率和寿命。
Description
技术领域
本发明涉及有机电致发光技术领域,更具体地,涉及一种含硅杂环化合物,该含硅杂环化合物在制备有机电致发光元件中的应用,以及含有该化合物的有机电致发光元件。
背景技术
有机电致发光元件所使用的物质大部分为纯有机物,或者为有机物与金属形成的有机金属络合物,根据用途可区分为空穴注入物、空穴输送物、发光物、电子输送物、电子注入物等。在此,作为空穴注入物或空穴输送物主要使用离子化能相对较小的有机物,作为电子注入物或电子输送物主要使用电负性较大的有机物。此外,作为发光辅助层所使用的物质最好能满足如下特性:
第一、有机电致发光元件中所使用的物质需有较好的热稳定性,其原因是在有机电致发光元件内部因电荷的迁移而发生焦耳热。目前,作为空穴输送层通常所使用材料的玻璃化温度低,因此在低温下驱动时,材料易发生结晶化而引起发光效率降低的现象。第二、为了降低驱动电压,需要将与阴极和阳极邻接的有机物设计成电荷注入势垒较小,电荷迁移率高的类型。第三、电极和有机层的界面、有机层和有机层的界面上一直存在能量壁垒而不可避免地累积一些电荷,因此需要使用电化学稳定性优异的物质。
发光层由主发光体和掺杂物这两种物质构成,掺杂物需要量子效率高,与掺杂物相比主发光体需要能隙大而容易发生向掺杂物的能量转移。用于电视、移动设备等的显示器根据红色、绿色、蓝色这三原色实现全彩色,发光层分别由红色主发光体/掺杂物、绿色主发光体/掺杂物以及蓝色主发光体/掺杂物构成。目前蓝光材料仍然存在发光量子效率低、色纯度差的问题。造成这种状况的主要原因是因为蓝光来自于能隙较宽的能级间的跃迁,而宽禁带的有机化合物在进行分子设计时存在一定的困难,其次蓝光材料的体系中存在着较强的π-π键相互作用,有着很强的电荷转移特性,从而使宽带隙中存在更多的无辐射弛豫通道,加剧了分子之间的荧光淬灭,降低了蓝光体系的量子产率。因此设计合成综合性能优良的蓝光材料,将成为有机电致发光材料研究的重要课题。
发明内容
基于以上事实,本发明的第一个目的在于提供一种含硅杂环化合物,其发光为深蓝色至蓝色且发光效率高。
本发明的第二个目的在于提供如上第一个目的所述的含硅杂环化合物在制备有机电致发光材料中的应用。
本发明的第三个目的在于提供一种有机电致发光材料。
本发明的第四个目的在于提供一种有机电致发光元件。
为达到上述第一个目的,本发明采用下述技术方案:
一种含硅杂环化合物,其结构通式如式I所示:
其中:
X1、X2彼此相同或不同,各自独立地选自O、S、SO、SO2、Se或SiR15R16;具体可为O、 S或SO2;
R4、R5、R6在每次出现时相同或不同地选自由经取代或未经取代的C1~C30烷基、经取代或未经取代的C6~C50芳基、经取代或未经取代的C3~C30环烷基、经取代或未经取代的C2~C50杂芳基组成的群组,任意相邻的两个R4、R5、R6可以任选地彼此连接以形成脂族环或芳族环;具体可为甲基;
R1、R2、R3、R7~R16在每次出现时相同或不同地选自由氢原子、氘原子、C1~C40的直链烷基、C3~C40的支链或环状的烷基(具体可为环丙基、环丁基、环戊基、环己基)、C1~C40的烷硅基(具体可为三甲基硅基、三乙基硅基、三异丙基硅基、三叔丁基硅基、三丁基硅基、三异丁基硅基、叔丁基二甲基硅基、异丁基二甲基硅基、异丙基二甲基硅基)、具有5至80 个(优选5至60个)碳原子的芳基(具体可为取代或未取代的苯基、取代或未取代的二联苯基)、具有2至80个(优选2至60个)碳原子的杂芳基、及式(II)组成的群组,R1~R16在每种情况下可以被一个或多个基团R取代,或这些基团中的两个、三个、四个或五个的组合,R在每种情况下可以是相同的或不同的,其中两个或更多个相邻的取代基可以任选地接合或稠合形成单环或多环的脂族、芳族环或杂芳族环系,所述环系可被一个或多个基团R取代;并且R15和R16不是氢原子或氘原子;
式(II)中,Ar1、Ar2各自相同或者不同,选自由具有5至80个(优选5至60个)碳原子的芳基、具有2至80个(优选2至60个)碳原子的杂芳基组成的群组;Ar1和Ar2可以任选地接合或稠合形成单环或多环的芳族环系或杂芳族环系,所述形成的环中含有或不含有杂原子N、O或S;
L表示单键、具有5至80个(优选5至60个)碳原子的亚芳基、具有2至80个(优选2至60 个)碳原子的亚杂芳基中的一种或这些基团的组合;
n表示0~5的整数;指示连接的位置;
R在每次出现时相同或不同地选自由氢、氘、经取代或未经取代的C1~C30烷基、经取代或未经取代的C6~C50芳基、经取代或未经取代的C3~C30环烷基、经取代或未经取代的C2~C50杂芳基、经取代或未经取代的C1~C30烷氧基、经取代或未经取代的C6~C30芳氧基、经取代或未经取代的C1~C30烷基硫基、经取代或未经取代的C5~C30芳基硫基、经取代或未经取代的C1~C30烷基胺基、经取代或未经取代的C5~C30芳基胺基、经取代或未经取代的C1~C30烷基甲硅烷基、经取代或未经取代的C5~C30芳基甲硅烷基、硝基、氰基或卤素组成的群组,相邻的两个或两个以上的R可以任选地彼此连接以形成脂族环或芳族环。
进一步地,所述含硅杂环化合物选自式III、式IV、式V或式VI表示的化合物:
其中,X1、X2彼此相同或不同,各自独立地选自O、S或SO2;
R4、R5、R6在每次出现时相同或不同地选自由经取代或未经取代的C1~C30烷基、经取代或未经取代的C6~C50芳基组成的群组,任意相邻的两个R4、R5、R6可以任选地彼此连接以形成脂族环或芳族环;
R1、R2、R3、R7~R14在每次出现时相同或不同地选自由氢原子、氘原子、C1~C40的直链烷基、C3~C40的支链或环状的烷基、C1~C40的烷硅基、具有5至80个(优选5至60个碳原子)的芳基、具有2至80个(优选2至60个)碳原子的杂芳基组成的群组,并且R15和R16不为氢原子或氘原子;
Ar1、Ar2各自相同或者不同,选自由具有5至80个(优选5至60个)碳原子的芳基、具有2 至80个(优选2至60个)碳原子的杂芳基组成的群组;Ar1和Ar2可以任选地接合或稠合形成单环或多环的芳族环系或杂芳族环系,所述形成的环中含有或不含有杂原子N、O或S;
具体地,Ar1、Ar2各自独立地为取代或未取代的苯基、取代或未取代的萘基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的菲基、取代或未取代的二苯醚基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的芴基、取代或未取代的螺芴基、或者Ar1、Ar2接合形成取代或未取代的咔唑环、Ar1、Ar2与碳原子接合形成取代或未取代的吖啶环、Ar1、Ar2与氮原子接合形成取代或未取代的吩嗪环、Ar1、Ar2与氧原子接合形成取代或未取代的吩噁嗪环、Ar1、Ar2与硫原子接合形成取代或未取代的吩噻嗪环中的任一种;
本说明书中,“取代或未取代的”这一用语是指,被选自氢、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环烷基、C3-C40环烯基、C6-C60芳基、C6-C60芳氧基、C6-C60芳硫醚基和C2-C60杂环芳基中的1个以上的取代基取代或未取代,或者被上述例示的取代基中的2个以上的取代基连接而成的取代基取代或未取代。
L表示单键、具有5至80个(优选5至60个)碳原子的亚芳基、具有2至80个(优选2至60 个)碳原子的亚杂芳基中的一种或这些基团的组合;
n表示0~5的整数,进一步的,n选自0、1或2。
更进一步地,所述含硅杂环化合物选自式2至式13表示的化合物:
其中R1~R14、Ar1、Ar2、L和n如上述所定义。
本发明意义上的芳基含有6~60个碳原子,在本发明意义上的杂芳基含有2~60个碳原子和至少一个杂原子,其条件是碳原子和杂原子的总和至少是5;所述杂原子优选自N、O 或S。此处的芳基或杂芳基被认为是指简单的芳族环,即苯、萘等,或简单的杂芳族环,如吡啶、嘧啶、噻吩等,或稠合的芳基或杂芳基,如蒽、菲、喹啉、异喹啉等。通过单键彼此连接的芳族环,例如联苯,相反地不被称为芳基或杂芳基,而是称为芳族环系。
在本发明意义上的芳族或芳族环系、杂芳族或杂芳族环系旨在被认为是指不必仅含有芳基或杂芳基的体系,而是其中多个芳基或杂芳基还可以由非芳族单元例如C、N、O或S原子连接。因此,例如,和其中两个或更多个芳基被例如短的烷基连接的体系一样,诸如芴、9,9’-螺二芴、9,9-二芳基芴、三芳基胺、二芳基醚等的体系也被认为是指在本发明意义上的芳族环系。
对于本发明意义上的烷基含有1~40个碳原子,并且其中单独的氢原子或-CH2-基团还可被氘、卤素、腈基、双键取代的烷基被认为是指如下基团: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、环己烯基、庚烯基、环庚烯基、辛烯基或环辛烯基。烷氧基优选具有1~30个碳原子的烷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。杂烷基优选具有1~30个碳原子的烷基,是指其中单独的氢原子或-CH2-基团可被氧、硫、卤素原子取代的基团,被认为是指烷氧基、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,根据本发明的环烷基可为环丙基、环丁基、环戊基、环己基、环丁烯基、环戊烯基、环己烯基、环庚基、环庚烯基,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。
根据本发明的芳基或杂芳基,在每种情况下还可被上述烷基取代的芳族或芳族环系、杂芳族或杂芳族环系,特别是指衍生自如下物质的基团:苯、萘、蒽、苯并蒽、菲、芘、苝、荧蒽、并四苯、并五苯、苯并芘、联苯、偶苯、三联苯、三聚苯、芴、螺二芴、二氢菲、二氢芘、四氢芘、顺式或反式茚并芴、顺式或反式茚并咔唑、顺式或反式吲哚并咔唑、三聚茚、异三聚茚、螺三聚茚、螺异三聚茚、呋喃、苯并呋喃、异苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、异苯并噻吩、二苯并噻吩、吡咯、吲哚、异吲哚、咔唑、吡啶、喹啉、异喹啉、吖啶、菲啶、苯并[5,6]喹啉、苯并[6,7]喹啉、苯并[7,8]喹啉、吩噻嗪、吩噁嗪、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡嗪并咪唑、喹喔啉并咪唑、噁唑、苯并噁唑、萘并噁唑、蒽并噁唑、菲并噁唑、异噁唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、六氮杂苯并菲、苯并哒嗪、嘧啶、苯并嘧啶、喹喔啉、1,5-二氮杂蒽、2,7-二氮杂芘、 2,3-二氮杂芘、1,6-二氮杂芘、1,8-二氮杂芘、4,5-二氮杂芘,4,5,9,10-四氮杂苝、吡嗪、吩嗪、吩噁嗪、吩噻嗪、荧红环、萘啶、氮杂咔唑、苯并咔啉、咔啉、菲咯啉、1,2,3-三唑、1,2,4- 三唑、苯并三唑、1,2,3-噁二唑、1,2,4-噁二唑、1,2,5-噁二唑、1,3,4-噁二唑、1,2,3-噻二唑、 1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、四唑、1,2,4,5- 四嗪、1,2,3,4-四嗪、1,2,3,5-四嗪、嘌呤、蝶啶、喹唑啉、吲嗪和苯并噻二唑或者衍生自这些体系的组合的基团。
进一步地,所述式I所示的化合物选自式CJHB880~CJHB949所示的化合物:
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为达到上述第二个目的,本发明提供一种如上第一个目的所述的化合物在制备有机电致发光材料中的应用。
为达到上述第三个目的,本发明提供有机电致发光材料,所述材料由如上第一个目的所述的化合物制备得到。
有机电致发光材料可以单独使用本发明的化合物构成,也可以同时含有其他化合物。
本发明的有机电致发光材料中所含有的本发明的含硅化合物可以用作但不限于发光层材料、载流子传输层材料或光折射层材料。
为达到上述第四个目的,本发明提供一种有机电致发光元件,所述有机电致发光元件包括第一电极、第二电极和置于所述第一电极、所述第二电极之间的一个或多个有机层,所述一个或多个有机层包含如上第一个目的所述的化合物。
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。具有例如激子阻挡功能的中间层同样可引入两个发光层之间。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装置可包含一个发光层,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。
进一步地,根据本发明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,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元件的其它层中,特别是在空穴注入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元件,可在该元件中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,可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,并且因此是结构化的。
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修饰多环芳族化合物获得可溶性化合物。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,可借助于升华方法来施加至少一个层,和/或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多环芳香族化合物,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。
进一步地,所述有机层还包含一个或多个电子注入层、电子输送层、空穴阻挡层、电子阻挡层、空穴输送层、空穴注入层、发光层、光折射层。
进一步地,所述发光层包含主体材料和掺杂物,所述主体材料选自由萘、蒽、芘、苝、菲、二苯并呋喃、二苯并噻吩、芴、螺芴、荧蒽、苯并蒽和并五苯及其衍生物组成的群组的化合物,所述掺杂物包含一种及以上第一个目的所述的含硅化合物。
进一步地,所述主体材料选自以下式A1~A48所示的化合物:
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进一步地,所述掺杂物与主体材料的质量比为1:99~50:50,具体可为10:90。
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。
本发明的有益效果如下:
本发明提供的含硅杂环化合物是一系列多环结构的新型有机电致发光化合物,多元杂环的引入不仅增大分子的电子云密度,同时增大了分子共轭面积提高内量子效率,含硅基团的加入与以住的化合物相比具有更低的升华温度。同时,该含硅杂环化合物阻碍有机分子间激-激复合物的生成、增加内部电子密度和稳定性,由此得以提高包含该化合物的有机电致发光器件的效率和寿命;此外,该化合物改善对溶液的溶解度而解决以往蓝光材料所具有的工序的生产性以及费用问题,并且在原有的工序中不是其蒸镀工序而是在其溶液工序中也可以用于制备发光层。
附图说明
图1是本发明的有机电致发光装置的一个含有CPL层的示意图;
图2是本发明的有机电致发光装置的一个不含空穴阻挡层的示意图。
附图标记
图1中,101是基板,102是阳极层,103是空穴注入层,104是空穴传输层,105是电子阻挡层,106是发光层,107是空穴阻挡层,108是电子传输层,109是电子注入层,110 是阴极层,111是CPL层。
图2中,101是基板,102是阳极层,103是空穴注入层,104是空穴传输层,105是电子阻挡层,106是发光层,107是电子传输层,108是电子注入层,109是阴极层,110是 CPL层。
具体实施方式
下述实施例中所使用的实验方法如无特殊说明,均为常规方法。
下述实施例中所用的材料、试剂等,如无特殊说明,均可从商业途径得到。
为了更清楚地说明本发明,下面结合优选实施例和附图对本发明做进一步的说明。附图中相似的部件以相同的附图标记进行表示。本领域技术人员应当理解,下面所具体描述的内容是说明性的而非限制性的,不应以此限制本发明的保护范围。
本发明中,制备方法如无特殊说明则均为常规方法。所用的原料如无特别说明均可从公开的商业途径获得,所述百分比如无特殊说明均为质量百分比。本发明提供的一系列新型有机化合物,所有的反应都是在众所周知的适合条件下进行,有些涉及到简单的有机制备,例如苯硼酸衍生物的制备均能通过熟练的操作技能合成,在本发明中没有详细描述。
下述实施例对OLED材料及元件进行性能测试的测试仪器及方法如下:
OLED元件性能检测条件:
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;
寿命测试:使用LTS-1004AC寿命测试装置。
实施例1
化合物A1的制备方法,包括如下步骤:
第一步:化合物Int.-1的制备
在氮气保护下,75.0mmol的1,4-二碘-2,5-二甲氧基苯(CAS:51560-21-5)溶解在60mL 的THF和30mL的三乙胺中,加入150.0mmol的对甲氧基苯乙炔、7.5mmol的碘化亚铜、0.75mmol的PdCl2(PPh3)2催化剂,搅拌反应12小时,反应结束后,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到Int.-1,为黄色固体,收率96%。
第二步:化合物Int.-2的制备
50.0mmol第一步制备的Int.-1溶解在100mL干燥的二氯甲烷中,在氮气保护下,滴加入0.1mol的碘溶于二氯甲烷的溶液,搅拌反应3小时,加入50mL的10%硫代硫酸钠水溶液,搅拌至无色,分出有机相,干燥,减压浓缩干,用硅胶柱分离纯化,得到中间体Int.-2,收率65%。
第三步:化合物Int.-3的制备
20.0mmol第二步制备的中间体Int.-2与40mL的THF混合,在氮气保护下,加入40.0mmol的三甲基硅基乙炔和20mL的三乙胺,再加入4.0mmol的碘化亚铜、0.4mmol的 PdCl2(PPh3)2催化剂,搅拌反应12小时,反应结束后,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到Int.-3,为黄色固体,收率100%。
第四步:化合物Int.-4的制备
20.0mmol第三步制备的中间体Int.-3与60mL的硝基甲烷混合,加入60.0mmol的溴化铜、10.0mmol的无水磷酸钾,搅拌反应24小时,反应结束后,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到Int.-4,收率87%。
第五步:化合物Int.-5的制备
20.0mmol第四步制备的中间体Int.-4与50mL的THF和10mL的三乙胺混合,加入0.5g的10%钯/碳,常压通入氢气,室温搅拌反应5小时,反应结束后,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到Int.-5,收率100%。
第六步:化合物Int.-6的制备
10.0mmol第五步制备的中间体Int.-5溶于50mL干燥的二氯甲烷中,在氮气保护下,降温至-78℃,缓慢滴加入20.5mmol的三溴化硼溶于二氯甲烷的溶液,搅拌反应30分钟,升至室温搅拌反应15小时,加入100mL的冰水,分出有机相,用水洗,有机相干燥,减压浓缩干,得到化合物Int.-6,收率78%。
第七步:化合物A1的制备
10.0mmol第六步制备的中间体Int.-6溶于50mL干燥的二氯甲烷中,在氮气保护下,加入40.0mmol的吡啶和1.0mmol的DMAP,降温至0℃,缓慢滴加入20.5mmol的三氟甲磺酸酐溶于二氯甲烷的溶液,搅拌反应30分钟,升至室温搅拌反应15小时,加入100mL的冰水,分出有机相,用水洗,有机相干燥,减压浓缩干,用硅胶柱分离纯化,得到化合物A1,收率86%,MS(TOF):m/z 798.0659[M+]。
参照上述类似的合成方法,制备以下化合物:
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实施例2
化合物A2的制备方法,包括如下步骤:
第一步:化合物Int.-7的制备
20.0mmol的实施例1制备的Int.-4、48.0mmol的苯硼酸、80.0mmol的无水碳酸钠和0.2mmol的Pd(PPh3)4混合,再中入60mL的THF和20mL的水,搅拌升温回流反应12小时,冷却到室温,加入20mL的乙醇,过滤,滤饼用水洗,乙醇洗,用硅胶柱分离纯化,得到中间体Int.-7,收率82%。
第二步:化合物Int.-8的制备
参照实施例1第六步的合成方法,仅将实施例1第六步的Int.-5替换为Int.-7,制备得到Int.-8,收率84%。
第三步:化合物A2的制备
参照实施例1第七步的制备方法,仅将实施例1第七步的中间体Int.-6替换为上步制备的中间体Int.-8,用硅胶柱分离纯化,获得化合物A2,收率87%,MS(TOF):m/z950.1282[M+]。
参照上述类似的合成方法,制备以下化合物:
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实施例3
化合物A11的制备方法,包括如下步骤:
第一步:化合物Int.-9的制备
20.0mmol的实施例1制备的Int.-4溶解于40.0mL干燥的THF中,用液氮降温至-78℃,再滴加入17.6mL的2.5M正丁基锂正己烷溶液,搅拌反应1小时,滴加入48.0mmol的三甲基氯硅烷,搅拌反应1小时,升到室温,加入20mL的饱和氯化铵水溶液,用乙酸乙酯萃取,收集有机相,干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到中间体Int.-9,收率90%。
第二步:化合物Int.-10的制备
参照实施例1第六步的合成方法,仅将实施例1第六步的Int.-5替换为Int.-9,制备得到Int.-10,收率65%。
第三步:化合物A11的制备
参照实施例1第七步的制备方法,仅将实施例1第七步的中间体Int.-6替换为上步制备的中间体Int.-10,用硅胶柱分离纯化,获得化合物A11,收率86%,MS(TOF):m/z942.1441 [M+]。
参照上述类似的合成方法,制备以下化合物:
实施例4
化合物A17的制备方法,包括如下步骤:
第一步:化合物Int.-11的制备
20.0mmol的参照实施例1制备的Int.-5’溶解于100.0mL的二氯甲烷中,用冰浴降温至 0℃,分批加入0.1mol的间氯过氧苯甲酸,搅拌反应2小时,升到室温,搅拌反应12小时,过滤,滤液用20%的碳酸钠水溶液洗,水洗,收集有机相干燥,减压浓缩干,用硅胶柱分离纯化,得到中间体Int.-11,白色固体,收率87%。
第二步:化合物Int.-12的制备
参照实施例1第六步的合成方法,仅将实施例1第六步的Int.-5替换为Int.-11,制备得到Int.-12,收率85%。
第三步:化合物A17的制备
参照实施例1第七步的制备方法,仅将实施例1第七步的中间体Int.-6替换为上步制备的中间体Int.-12,用硅胶柱分离纯化,获得化合物A17,收率82%,MS(TOF):m/z893.9996 [M+]。
参照上述类似的合成方法,制备以下化合物:
实施例5
化合物CJHB881的制备:
20.0mmol的A1与80mL的甲苯混合,加入48.0mmol的二(对叔丁基苯基)胺、60.0mmol 的叔丁醇钠、0.2mmol的Pd2(dba)3催化剂和0.4mmol的Xanphos,升温至100℃搅拌反应 20小时,反应结束后,降到室温,加入50mL的水,过滤,滤饼用水洗,乙醇洗,真空升华纯化,得到化合物CJHB881,白色固体,HPLC:99.96%,收率78%,MS(TOF):m/z 1061.5822[M+H]+。
参照上述类似的合成方法,制备以下化合物:
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实施例6
一种OLED元件,如图2所示,该有机电致发光装置具有101是基板,102是阳极层,103是空穴注入层,104是空穴传输层,105是电子阻挡层,106是发光层,107是电子传输层,108是电子注入层,109是阴极层,110是CPL层。图2所示的OLED元件不包含CPL 层的制备方法包括如下步骤:
1)将涂布了ITO导电层的玻璃基板依次在清洗剂中超声处理30分钟,在去离子水中冲洗,在丙酮/乙醇混合溶剂中超声30分钟,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,并用低能阳离子束轰击表面,得到阳极。
2)把上述处理好的ITO玻璃基板置于真空腔内,抽真空至1×10-5~9×10-3Pa,在上述阳极层膜上继续分别蒸镀化合物DNTPD作为空穴注入层,蒸镀膜厚为在上述空穴注入层膜上继续蒸镀NPB为空穴传输层,蒸镀膜厚为/>/>
3)在空穴传输层上继续蒸镀一层化合物HT202作为电子阻挡层,蒸镀膜厚为
4)在电子阻挡层上继续蒸镀一层本发明的式I所示的含硅杂环化合物和BH011作为发光层,其中,BH011为主体材料,本发明的式I所示的含硅杂环化合物为掺杂材料,式I所示的含硅杂环化合物在BH011中的掺杂浓度为10%,蒸镀膜厚为
5)在上述发光层上再继续蒸镀一层化合物LiQ和ET205作为器件的电子传输层,其中, LiQ和ET205的质量比为1:1,蒸镀膜厚为
6)在上述电子传输层上再继续蒸镀一层化合物LiF作为器件的电子注入层,蒸镀膜厚为最后,在上述电子注入层之上蒸镀金属铝作为元件的阴极层,蒸镀膜厚为
上述实施例6中使用的化合物结构如下:
比较例1
参照实施例6相同的步骤,不同之处在于使用化合物BD010代替式I所示的化合物。
化合物BD010的结构为:
比较例2
参照实施例6相同的步骤,不同之处在于使用化合物BD020代替式I所示的化合物。
化合物BD020的结构为:
所得有机发光元件的性能检测结果示于下表2中:
表2性能检测结果
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上述表中,在电流密度为10mA/cm2条件下的驱动电压、效率、外量子效率EQE以及在亮度为1000cd/m2初始条件下的器件LT95%寿命的数据是针对比较例1归一化。
结论:从性能测试结果表2可以看到,本发明的含硅杂环化合物作为蓝光掺杂材料获得了有机电致发光元件,相较于采用BD010或BD020作为掺杂材料的有机电致发光元件,元件的效率和外量子效率提高,而驱动电压降低,而且器件初始亮度在1000cd/m2的条件下的LT95%寿命也有非常好的表现。
产业上的应用可能性
本发明的有机电致发光装置可以在壁挂电视、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。
显然,本发明的上述实施例仅仅是为清楚地说明本发明所作的举例,而并非是对本发明的实施方式的限定,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,这里无法对所有的实施方式予以穷举,凡是属于本发明的技术方案所引伸出的显而易见的变化或变动仍处于本发明的保护范围之列。
Claims (10)
1.一种含硅杂环化合物,其特征在于,所述化合物的结构通式如式I所示:
其中:
X1、X2彼此相同或不同,各自独立地选自O、S或SO2;
R4、R5、R6为甲基;
R1、R2、R3、R7~R14在每次出现时相同或不同地选自由氢原子、C1~C40的直链烷基、环丙基、环丁基、环戊基、环己基、三甲基硅基、三乙基硅基、三异丙基硅基、三叔丁基硅基、三丁基硅基、三异丁基硅基、叔丁基二甲基硅基、异丁基二甲基硅基、异丙基二甲基硅基、取代或未取代的苯基、取代或未取代的二联苯基组成的群组;
式(II)中,Ar1、Ar2各自相同或者不同,选自由由取代或未取代的苯基、取代或未取代的萘基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的菲基、取代或未取代的二苯醚基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的芴基、取代或未取代的螺芴基、或者Ar1、Ar2接合形成取代或未取代的咔唑环、Ar1、Ar2与碳原子接合形成取代或未取代的吖啶环、Ar1、Ar2与氮原子接合形成取代或未取代的吩嗪环、Ar1、Ar2与氧原子接合形成取代或未取代的吩噁嗪环、Ar1、Ar2与硫原子接合形成取代或未取代的吩噻嗪环中的任一种;
L表示单键;
n选自0或1;指示连接的位置。
2.根据权利要求1所述的含硅杂环化合物,其特征在于,所述化合物选自式III、式IV、式V或式VI表示的化合物:
其中,X1、X2彼此相同或不同,各自独立地选自O、S或SO2;
R4、R5、R6为甲基;
R1、R2、R3、R7~R14在每次出现时相同或不同地选自由氢原子、C1~C40的直链烷基、环丙基、环丁基、环戊基、环己基、三甲基硅基、三乙基硅基、三异丙基硅基、三叔丁基硅基、三丁基硅基、三异丁基硅基、叔丁基二甲基硅基、异丁基二甲基硅基、异丙基二甲基硅基、取代或未取代的苯基、取代或未取代的二联苯基组成的群组;
n选自0或1;
Ar1、Ar2、L如权利要求1中所定义。
3.根据权利要求1所述的含硅杂环化合物,其特征在于,所述化合物选自式2至式13表示的化合物:
其中,R4、R5、R6为甲基;
R1、R2、R3、R7~R14在每次出现时相同或不同地选自由氢原子、C1~C40的直链烷基、环丙基、环丁基、环戊基、环己基、三甲基硅基、三乙基硅基、三异丙基硅基、三叔丁基硅基、三丁基硅基、三异丁基硅基、叔丁基二甲基硅基、异丁基二甲基硅基、异丙基二甲基硅基、取代或未取代的苯基、取代或未取代的二联苯基;
Ar1、Ar2各自相同或者不同,选自由取代或未取代的苯基、取代或未取代的萘基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的菲基、取代或未取代的二苯醚基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的芴基、取代或未取代的螺芴基、或者Ar1、Ar2接合形成取代或未取代的咔唑环、Ar1、Ar2与碳原子接合形成取代或未取代的吖啶环、Ar1、Ar2与氮原子接合形成取代或未取代的吩嗪环、Ar1、Ar2与氧原子接合形成取代或未取代的吩噁嗪环、Ar1、Ar2与硫原子接合形成取代或未取代的吩噻嗪环中的任一种;
L表示单键;
n选自0或1。
4.根据权利要求1所述的含硅杂环化合物,其特征在于,所述化合物选自式CJHB880~CJHB949所示的化合物:
5.权利要求1-4中任一项所述的含硅杂环化合物作为有机电致发光材料在制备有机电致发光元件中的应用。
6.一种有机电致发光元件,包括第一电极、第二电极和置于所述第一电极与所述第二电极之间的一个或多个有机层,其特征在于,所述一个或多个有机层包含权利要求1-4任中一项所述的含硅杂环化合物。
7.根据权利要求6所述的有机电致发光元件,其特征在于,所述有机层包含一个或多个电子注入层、电子输送层、空穴注入层、空穴输送层、空穴阻挡层、电子阻挡层和发光层,并且所述有机层中的至少一种包含权利要求1~4中任一项所述的含硅杂环化合物。
8.根据权利要求7所述的有机电致发光元件,其特征在于,所述发光层包含主体材料和掺杂物,所述主体材料选自由萘、蒽、芘、苝、菲、二苯并呋喃、二苯并噻吩、芴、螺芴、荧蒽、苯并蒽和并五苯组成的群组的化合物,所述掺杂物包含如权利要求1-4中任一项所述的含硅杂环化合物。
9.根据权利要求8所述的有机电致发光元件,其特征在于,所述主体材料选自式A1~A48所示的化合物:
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10.根据权利要求8或9所述的有机电致发光元件,其特征在于,所述作为掺杂物的含硅杂环化合物与主体材料的质量比为1:99~50:50。
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