CN116462592A - 一种化合物及其在有机光电器件中的应用 - Google Patents
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Classifications
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- C07D209/80—[b, c]- or [b, d]-condensed
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- C07D209/82—Carbazoles; Hydrogenated carbazoles
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
本发明公开了一种化合物及其在有机光电器件中的应用,该化合物的化学结构如式(Ⅰ)所示:X选自C(R9R10)、N(R11)、Si(R12R13)、B(R14)、O或S;Ar1和Ar2独立选自取代或未取代的C6‑C30的芳基、取代或未取代的C5‑C30的杂芳基。本发明的化合物应用到有机光电器件能使器件具有较高的空穴迁移率,并且能够有效的阻挡电子、激子进入到空穴传输层中,从而提高器件的效率,同时分子具有高的稳定性,能进一步提升器件的发光效率和使用寿命。
Description
技术领域
本发明属于有机电致发光材料领域,特别涉及一种化合物及其在有机光电器件中的应用。
背景技术
有机电致发光(OLED)器件是一类具有类三明治结构的器件,包括正负电极膜层及夹在电极膜层之间的有机功能材料层。目前,该技术已被广泛应用于新型照明灯具、智能手机及平板电脑等产品的显示面板,进一步还将向电视等大尺寸显示产品应用领域扩展,是一种发展快、技术要求高的新型显示技术。常见的应用于OLED器件的功能化有机材料有:空穴注入材料、空穴传输材料、空穴阻挡材料、电子注入材料、电子传输材料、电子阻挡材料以及发光主体材料和发光客体(染料)等。基于此,OLED材料界一直致力于开发新的有机电致发光材料以实现器件低启动电压、高发光效率和更优的使用寿命。到目前为止,现有的OLED光电功能材料的发展还远远落后于面板制造企业对OLED材料的要求,开发性能更好的有机功能材料满足当前产业发展需求显得尤为紧迫。
目前,空穴传输材料主要采用具有良好的空穴传输特性的芳香胺化合物,N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺(NPB)具有适中的最高已占据轨道能级和良好的空穴迁移率,从而被广泛应用于多种色光的有机电致发光器件。然而,该分子的玻璃化转化温度较低(98℃),器件在长时间工作时累积焦耳热的作用下容易发生相变,从而对器件的寿命造成较大的影响。因此,设计同时具有较高迁移率和玻璃化转变温度的空穴传输材料十分有必要。
发明内容
鉴于以上所述现有技术的缺点,本发明的目的在于提供一种化合物及其在有机光电器件中的应用,用于解决现有技术中的问题。
为实现上述目的及其他相关目的,本发明一方面提供一种化合物,所述化合物的化学结构如式(Ⅰ)所示:
式(Ⅰ)中,A选自如下基团中至少一种:
Z1-Z75各自独立选自C(R3R4)、N(R5)、Si(R6R7)、B(R8)、O或S;
X选自C(R9R10)、N(R11)、Si(R12R13)、B(R14)、O或S;
R1-R14相同或不同,各自独立地选自氢、氘、取代或未取代的直链或支链的C1-C30的烷基、取代或未取代的C1-C30的杂烷基、取代或未取代的C3-C30的环烷基、取代或未取代的C3-C30的杂环烷基、取代或未取代的C6-C30的芳基、或取代或未取代的C6-C30的杂芳基;
L1-L3相同或不同,各自独立地选自单键、取代或未取代的C6-C30的亚芳基、取代或未取代的C3-C30的亚杂芳基;
Ar1和Ar2相同或不同,各自独立选自取代或未取代的C6-C30的芳基、取代或未取代的C5-C30的杂芳基。
本发明另一方面提供一种有机层,包括本发明前述的化合物。
本发明另一方面提供本发明前述的化合物和/或前述的有机层在有机光电器件中的应用。
本发明另一方面提供一种有机光电器件,其包括第一电极、第二电极和本发明前述的有机层,其中,所述有机层为空穴注入层、空穴传输层、发光层、电子注入层或电子传输层中至少一层。
本发明另一方面提供一种显示或照明装置,包括本发明前述的有机光电器件。
与现有技术相比,本发明的有益效果为:
本发明提供的化合物因为基团连接的位置在芴衍生物的1或4位,使分子的空间构型可以固定,减少不必要的旋转,从而可以使分子更加稳定。另外,和现有的化合物相比,因为空间位阻的关系,本发明的化合物分子更加稳定。本发明的化合物应用到有机光电器件能使器件具有更高的空穴迁移率,并且能够有效的阻挡电子、激子进入到空穴传输层中,器件具有更高的发光效率和使用寿命。
具体实施方式
本发明提供一种化合物,将苯并烷烃衍生物引入到三芳胺类体系获得一系列性能优良的空穴传输材料。苯并烷烃衍生物的引入,不仅有利于提高分子片段稳定性,同时也增加分子量,进而提高分子的玻璃化转变温度。此外,脂肪环相对于芳基具有更好的给电子能力,使得化合物具有良好的空穴传输性能和热稳定性。因此,这类化合物能够为有机光电器件提供较长的使用寿命。
本发明中前述化合物的化学结构如式(Ⅰ)所示:
式(Ⅰ)中,A选自如下基团中至少一种:
Z1-Z75各自独立选自C(R3R4)、N(R5)、Si(R6R7)、B(R8)、O或S;
X选自C(R9R10)、N(R11)、Si(R12R13)、B(R14)、O或S;
R1-R14相同或不同,各自独立地选自氢、氘、取代或未取代的直链或支链的C1-C30的烷基、取代或未取代的C1-C30的杂烷基、取代或未取代的C3-C30的环烷基、取代或未取代的C3-C30的杂环烷基、取代或未取代的C6-C30的芳基、或取代或未取代的C6-C30的杂芳基;
L1-L3相同或不同,各自独立地选自单键、取代或未取代的C6-C30的亚芳基、取代或未取代的C3-C30的亚杂芳基;
Ar1和Ar2相同或不同,各自独立选自取代或未取代的C6-C30的芳基、取代或未取代的C5-C30的杂芳基。
本发明中取代基的实例描述如下,但取代基并不限于此:
【取代或未取代】是指经选自以下的一个或更多个取代基取代:氘、卤素基团、腈基、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、杂芳基、苊基或未取代;或者经连接以上示例的取代基中的两个或多个取代基的取代基取代,或未取代。例如,“连接两个或更多个取代基的取代基”可包括联苯基,即联苯基可为芳基,或者为连接两个苯基的取代基。
【烷基】可为直链或支链的,并且碳原子数没有特别限制。在一些实施例中,烷基包括但不限于甲基、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、4-甲基己基、5-甲基己基。
以上对烷基的描述也可用于芳烷基、芳烷基胺基、烷基芳基和烷基胺基中的烷基。
【杂烷基】可为含杂原子的直链或支链的烷基,并且碳原子数没有特别限制。在一些实施例中,杂烷基包括但不限于烷氧基、烷硫基、烷基磺酰基。烷氧基包括但不限于甲氧基、乙氧基、正丙氧基、异丙氧基(isopropoxy)、异丙氧基(i-propyloxy)、正丁氧基、异丁氧基、叔丁氧基、仲丁氧基、正戊氧基、新戊氧基、异戊氧基、正己氧基、3,3-二甲基丁氧基、2-乙基丁氧基、正辛氧基、正壬氧基、正癸氧基、苄氧基、对甲基苄氧基;烷硫基包括但不限于甲硫基、乙硫基、正丙硫基、异丙硫基、异丙硫基、正丁硫基、异丁硫基、叔丁硫基、仲丁硫基、正戊硫基、新戊硫基、异戊硫基、正己硫基、3,3-二甲基丁硫基、2-乙基丁硫基、正辛硫基、正壬硫基、正癸硫基、苄硫基等。
【环烷基】可为环状的,并且碳原子数没有特别限制。在一些实施例中,环烷基包括但不限于环丙基、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。
【杂环烷基】可为含杂原子的环烷基,并且碳原子数没有特别限制。在一些实施例中,杂环烷基包括但不限于等。
【芳基】没有特别限定,芳基可为单环芳基或多环芳基。在一些实施例中,单环芳基包括但不限于苯基、联苯基、三联苯基、四联苯基、五联苯基等;多环芳基包括但不限于萘基、蒽基、菲基、芘基、苝基、芴基等;芴基可为经取代的,例如9,9’-二甲基芴基、9,9’-二苯并芴基等。此外,取代基中的两个可彼此结合形成螺环结构,例如9,9’-螺二芴基等。
以上对芳基的描述可用于亚芳基,不同之处在于亚芳基为二价。
以上对芳基的描述可用于芳氧基、芳基硫基、芳基磺酰基、芳基膦基、芳烷基、芳烷基胺基、芳烯基、烷基芳基、芳基胺基和芳基杂芳基胺基中的芳基。
【杂芳基】包含N、O、P、S、Si和Se中的一个或多个作为杂原子,杂芳基包括但不限于吡啶基、吡咯基、嘧啶基、哒嗪基、呋喃基、噻吩基、咪唑基、吡唑基、唑基、异唑基、噻唑基、异噻唑基、三唑基、二唑基、噻二唑基、二噻唑基、四唑基、吡喃基、噻喃基、吡嗪基、嗪基、噻嗪基、二氧杂环己烯基、三嗪基、四嗪基、喹啉基、异喹啉基、喹啉基、喹唑啉基、喹喔啉基、萘啶基、吖啶基、呫吨基、菲啶基、二氮杂萘基、三氮杂茚基、吲哚基、二氢吲哚基、中氮茚基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、苯并噻唑基、苯并噁唑基、苯并咪唑基、苯并噻吩基、苯并呋喃基、二苯并噻吩基、二苯并呋喃基、咔唑基、苯并咔唑基、二苯并咔唑基、吲哚并咔唑基、茚并咔唑基、吩嗪基、咪唑并吡啶基、吩嗪基、菲啶基、菲咯啉基、吩噻嗪基、咪唑并吡啶基、咪唑并菲啶基、苯并咪唑并喹唑啉基、苯并咪唑并菲啶基、螺[芴-9,9'-氧杂蒽]、苯联萘基、二萘并呋喃基、萘苯并呋喃基、二萘并噻吩基、萘苯并噻吩基、三苯基氧化膦、三苯基硼烷等。
以上对杂芳基的描述可用于杂芳基胺基和芳基杂芳基胺基中的杂芳基。
以上对杂芳基的描述可用于亚杂芳基,不同之处在于亚杂芳基为二价的。
在一些实施例中,式(Ⅰ)中,前述提到的烷基的碳原子个数也可以为1-10、1-20、或20-30等。前述提到的环烷基的碳原子个数也可以为3-10、3-20、或3-30等。前述提到的杂烷基的碳原子个数也可以是3-10、1-20、或20-30等。前述提到的杂环烷基的碳原子个数也可以为3-10、3-20、或20-30等。前述提到的芳基的碳原子个数也可以为6-10、6-20、或20-30等。前述提到的杂芳基的碳原子个数也可以为6-10、6-20、或20-30等。
上述对于芳基和杂芳基的碳原子个数的描述适用于本发明中提到的亚芳基和亚杂芳基。
在一些实施例中,式(Ⅰ)中,基团A选自如下所示基团中至少一种:
其中,R16-R23各自独立选自选自氢、氘、取代或未取代的C1-C60的烷基、取代或未取代的C1-C60的环烷基、取代或未取代的C1-C60的杂烷基、取代或未取代的C1-C60的杂环烷基、取代或未取代的C1-C60的芳基或取代或未取代的C1-C60的杂芳基;
其中,*为连接位点,不局限于单个链接,也可以代表多个链接;链接点位不仅仅局限于前述基团A的环中,也代表在所示基团的任意位置;也可以代表和临近的原子键合成环。
在一些实施例中,式(Ⅰ)中,基团A选自如下所示基团中至少一种:
Ar3选自取代或未取代的C6-C30的芳基、取代或未取代的C5-C30的杂芳基。更优选地,基团A中与Ar3形成并环的烷基选自如下结构中至少一种:
其中,RC选自C6-C30芳基、C5-C30杂芳基。
在一些实施例中,式(Ⅰ)中,基团A选自如下所示基团中的一种:
在一些实施例中,式(Ⅰ)中,R1、R2各自独立选自氢、氘;
和/或,R3-R13相同或不同,各自独立地选自氢、氘、取代或未取代的直链或支链的C1-C30的烷基、取代或未取代的C1-C12的烷氧基、取代或未取代的C1-C12的烷硫基、取代或未取代的C3-C30的环烷基、取代或未取代的C3-C30的杂环烷基、取代或未取代的C6-C30的芳基、或取代或未取代的C6-C30的杂芳基。
在一些实施例中,式(Ⅰ)中,L1-L3各自独立选自单键、取代或未取代的亚苯基、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚三联苯基、取代或未取代的亚蒽基、取代或未取代的亚菲基,或者选自如下取代基:
在一些实施例中,式(Ⅰ)中,Ar1、Ar2各自独立选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的三联苯基,或者选自如下取代基:
在一些实施例中,式(Ⅰ)中,X1、X2各自独立选自O、S或如下结构中的一种:
其中,Y1-Y23选自N(R24)、C(R25R26)、或Si(R27R28)、O或S;
Ar4和Ar5选自取代或未取代的C6-C30的芳基、取代或未取代的C5-C30的杂芳基;
R24-R28各自独立选自选自氢、氘、取代或未取代的C1-C60的烷基、取代或未取代的C1-C60的环烷基、取代或未取代的C1-C60的杂烷基、取代或未取代的C1-C60的杂环烷基、取代或未取代的C1-C60的芳基、或取代或未取代的C1-C60的杂芳基;*为原子的连接位点。
具体的,前述任一化学结构或基团中可为未取代或者选自以下的一个或多个取代基取代:例如可以是氘、卤素基团、腈基、硝基、羟基、羰基、酯基、酰亚胺基、胺基、氧化膦基团、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、芳基杂芳基胺基、芳基膦基和杂芳基等。
在一些实施例中,式(Ⅰ)所示的化合物选自以下化学结构中至少一种:
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本发明另一方面提供一种有机层,包括本发明前述的化合物。
本发明另一方面提供如本发明前述的化合物和/或前述的有机层在有机光电器件中的应用。
本发明所提供的有机光电器件中,包括第一电极、第二电极、以及设置在第一电极和第二电极之间的一个或多个有机层,为底部或顶部发光器件结构,其有机层可为单层结构,也可为层合有两个或多个有机层的多层串联结构,所述有机层如具有包括空穴注入层、空穴传输层、发光层、电子注入层或电子传输层中至少一层。可使用制备有机光电器件的常见方法和材料来制备。本发明的有机光电器件采用化合物作为有机光电器件的有机层。
本发明所提供的有机光电器件中,第一电极作为阳极层,阳极材料例如可以是具有大功函数的材料,使得空穴顺利地注入有机层。更例如可以是金属、金属氧化物、金属和氧化物的组合、导电聚合物等。金属氧化物例如可以是氧化铟锡(ITO)、氧化锌、氧化铟、和氧化铟锌(IZO)等。
本发明所提供的有机光电器件中,第二电极作为阴极层,阴极材料例如可以是具有小功函数的材料,使得电子顺利地注入有机层。阴极材料例如可以是金属或多层结构材料。金属例如可以是镁、银、钙、钠、钾、钛、铟、钇、锂、钆、铝、锡和铅、或其合金。阴极材料优选选自镁和银。
本发明所提供的有机光电器件中,空穴注入层的材料,优选最高占据分子轨道(HOMO)介于阳极材料的功函数与周围有机层的HOMO之间的材料作为在低电压下有利地从阳极接收空穴的材料。
本发明所提供的有机光电器件中,空穴传输层的材料是对空穴具有高迁移率的材料适合作为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的材料。空穴传输层的材料包括但不限于芳基胺的有机材料、导电聚合物、同时具有共轭部分和非共轭部分的嵌段共聚物等。
本发明所提供的有机光电器件中,发光层的材料通常可以选自对荧光或磷光具有良好量子效率的材料作为能够通过接收分别来自空穴传输层和来自电子传输层的空穴和电子并使空穴与电子结合而在可见光区域内发光的材料。
本发明所提供的有机光电器件中,电子传输层的材料是对电子具有高迁移率的材料适合作为有利地接收来自阴极的电子并将电子传输至发光层的材料。
本发明所提供的有机光电器件中,覆盖层的材料通常具有高折射率,因此可有助于有机发光器件的光效率提高,尤其是有助于外部发光效率提高。
本发明所提供的有机光电器件中,所述有机光电器件为有机光伏器件、有机发光器件、有机太阳电池、电子纸、有机感光体、有机薄膜晶体管等。
本发明另一方面提供一种显示或照明装置,包括本发明所述的有机光电器件。
以下通过特定的具体实例说明本发明的实施方式。
合成实施例:
上述式(Ⅰ)所示的化合物的合成可以使用已知的方法进行。例如,使用镍、钯等过渡金属的交叉偶合反应,其他合成方法是使用镁或锌等过渡金属的C-C、C-N偶联生成反应。上述反应,限于反应条件温和、各种官能团的选择性优越等特点,优选Suzuki、Buchwald反应。本发明的化合物用以下实施例举例说明,但并不限于这些实施例举例的化合物和合成方法。本发明的初始原料和溶剂和一些常用的OLED中间体类等产品购于国内的OLED中间体厂商,各种钯催化剂、配体等购于sigma-Aldrich公司。1H-NMR数据使用JEOL(400MHz)核磁共振仪来测定;HPLC数据使用岛津LC-20AD高效液相仪来测定。
实施例中使用化合物为:
实施例1
化合物1的合成
1)中间体1-1的合成
在氩气氛围下,向反应容器中加入化合物1-A 31.0克(100mmol),化合物1-B 16.9克(100mmol),叔丁醇钠23.4克(240mmol),双二亚苄基丙酮钯575毫克(1mmol%),2-双环己基膦-2',4',6'-三异丙基联苯953毫克(2mmol%)和1000mL二甲苯(xylene),在140℃加热搅拌15小时。反应混合物冷却到室温,加入1000ml水,过滤,滤饼用大量水洗涤,真空干燥,粗品通过硅胶柱层析法精制(洗脱液:乙酸乙酯/己烷),得到29.8克化合物1-1,HPLC纯度99.1%,收率75%。LC MS:M/Z 397.16(M+)。
1H NMR(400MHz,DMSO-d6)δ1.69(s,6H),7.08(d,1H),7.14(m,1H),7.17–7.34(m,6H),7.34–7.43(m,1H),7.43–7.54(m,4H),7.57–7.65(m,2H),7.69–7.76(m,2H),7.78(d,1H).
2)中间体1-2的合成
在氩气氛围下,向反应容器中加入化合物1-1 39.8克(100mmol),化合物1-C 23.3克(100mmol),叔丁醇钠23.4克(240mmol),双二亚苄基丙酮钯575毫克(1mmol%),2-双环己基膦-2',4',6'-三异丙基联苯953毫克(2mmol%)和1000mL二甲苯(xylene),在140℃加热搅拌15小时。反应混合物冷却到室温,加入1000ml水,过滤,滤饼用大量水洗涤,真空干燥,粗品通过硅胶柱层析法精制(洗脱液:乙酸乙酯/己烷),得到43.5克化合物1,HPLC纯度99.5%,收率79%。LC MS:M/Z 549.22(M+)。
1H NMR(400MHz,DMSO-d6)δ1.69(s,6H),7.08(d,1H),7.14(m,1H),7.17–7.43(m,11H),7.43–7.58(m,8H),7.69–7.76(m,4H),7.78(d,1H).
3)化合物1的合成
在氩气氛围下,向反应容器中加入化合物1-2 76.0克(100mmol),化合物1-D23.3克(100mmol),XPhos Pd G3 787毫克(1mmol%),1.5M磷酸钾50ml(300mmol)和四氢呋喃1000ml(THF),回流加热搅拌一晚。冷却至室温,加入800ml水,大量固体析出,过滤,滤饼用水搅洗3次,真空干燥。粗品通过硅胶柱层析法精制(洗脱液:乙酸乙酯/己烷),得到41.1克化合物1,收率65%,HPLC纯度99.9%。LC-MS:M/Z 631.32(M+)。
1H NMR(400MHz,DMSO-d6)δ1.69(s,6H),2.07(m,2H),2.77–2.99(m,4H),7.15–
7.58(m,24H),7.68–7.77(m,5H).
实施例2
化合物4的合成
除了起始原料更换为4-A、4-B、4-C和4-D以外,其他与实施例1相同。LC MS:M/Z843.35(M+)。合成总收率:37%;HPLC纯度:99.9%。
1H NMR(400MHz,DMSO-d6)δ1.93–2.08(m,2H),2.63–2.74(m,1H),2.70–2.80(m,1H),2.80–2.89(m,2H),7.01–7.11(m,3H),7.13–7.59(m,26H),7.64–7.80(m,6H),7.91(m,3H),7.94–8.02(m,1H).
实施例3
化合物5的合成
除了起始原料更换为5-A、5-B、5-C和5-D以外,其他与实施例1相同。LC MS:M/Z837.34(M+)。合成总收率:38%;HPLC纯度:99.9%。
1H NMR(400MHz,DMSO-d6)δ2.07(m,2H),2.77–2.99(m,4H),6.00(d,1H),6.93(d,1H),7.03–7.11(m,6H),7.13–7.22(m,3H),7.22–7.30(m,7H),7.30–7.38(m,4H),7.34–7.44(m,2H),7.44–7.53(m,6H),7.50–7.59(m,6H),7.69–7.77(m,2H),7.77–7.87(m,2H),7.94(d,1H).
实施例4
化合物8的合成
除了起始原料更换为8-A、8-B、8-C和8-D以外,其他与实施例1相同。LC MS:M/Z711.31(M+)。合成总收率:36%;HPLC纯度:99.9%。
1H NMR(400MHz,DMSO-d6)δ1.93–2.08(m,2H),2.63–2.74(m,1H),2.70–2.80(m,1H),2.80–2.89(m,2H),4.10–4.21(m,2H),4.21–4.32(m,2H),7.07–7.14(m,1H),7.14–7.20(m,1H),7.26–7.39(m,8H),7.34–7.46(m,5H),7.41–7.53(m,5H),7.49–7.60(m,4H),7.65(d,1H),7.68–7.77(m,5H),7.80–7.88(m,1H).
实施例5
化合物13的合成
除了起始原料更换为13-A、13-B、13-C和13-D以外,其他与实施例1相同。LC MS:M/Z876.44(M+)。合成总收率:38%;HPLC纯度:99.9%。
1H NMR(400MHz,DMSO-d6)δ1.11–1.23(m,1H),1.28–1.38(m,1H),1.33–1.47(m,2H),1.47–1.56(m,1H),1.51–1.64(m,2H),1.60–1.76(m,1H),1.79–1.96(m,2H),1.91–2.12(m,3H),2.07–2.15(m,1H),2.25–2.35(m,2H),2.63–2.74(m,1H),2.70–2.80(m,1H),2.80–2.89(m,2H),6.68(s,2H),7.00(m,1H),7.04–7.12(m,2H),7.15–
7.59(m,21H),7.63(m,2H),7.87–7.97(m,2H),8.26(m,5H).
实施例6
化合物15的合成
除了起始原料更换为15-A、15-B、15-C和15-D以外,其他与实施例1相同。LC MS:M/Z778.43(M+)。合成总收率:37%;HPLC纯度:99.9%。
1H NMR(400MHz,DMSO-d6)δ1.22(d,12H),1.69(s,6H),1.80(s,2H),7.00(m,2H),7.04–7.14(m,8H),7.14–7.34(m,12H),7.34–7.53(m,8H),7.48–7.58(m,2H),7.67(t,1H),7.77(t,1H).
实施例7
化合物30的合成
除了起始原料更换为30-A、30-B、30-C和30-D以外,其他与实施例1相同。LC MS:M/Z764.41(M+)。合成总收率:38%;HPLC纯度:99.9%。
1H NMR(400MHz,DMSO-d6)δ1.22(d,12H),1.48(s,4H),1.69(s,6H),6.67(m,1H),7.04(m,1H),7.08–7.50(m,19H),7.50–7.58(m,1H),7.58–7.68(m,2H),7.64–7.76(m,3H),7.73–7.83(m,1H),8.15–8.25(m,2H).
实施例8
化合物43的合成
除了起始原料更换为43-A、43-B、43-C和43-D以外,其他与实施例1相同。LC MS:M/Z820.29(M+)。合成总收率:38%;HPLC纯度:99.9%。
1H NMR(400MHz,DMSO-d6)δ1.68–1.91(m,6H),2.83(m,4H),5.75(d,1H),6.54(d,1H),7.05(m,1H),7.30–7.39(m,2H),7.35–7.62(m,19H),7.62(m,2H),7.69–7.80(m,3H),7.88–7.95(m,2H),8.17–8.25(m,2H),8.45(m,1H).
实施例9
化合物59的合成
除了起始原料更换为59-A、59-B、59-C和59-D以外,其他与实施例1相同。LC MS:M/Z689.24(M+)。合成总收率:37%;HPLC纯度:99.9%。
1H NMR(400MHz,DMSO-d6)δ3.23(m,2H),4.53–4.69(m,2H),6.00(d,1H),6.93(d,1H),6.99–7.07(m,2H),7.09–7.22(m,2H),7.23(m,1H),7.29(d,2H),7.31–7.44(m,7H),7.44–7.53(m,5H),7.50–7.57(m,2H),7.57–7.66(m,2H),7.69–7.80(m,3H),7.77–7.87(m,2H),8.42(t,1H).
实施例10
化合物68的合成
除了起始原料更换为68-A、68-B、68-C和68-D以外,其他与实施例1相同。LC MS:M/Z665.28(M+)。合成总收率:39%;HPLC纯度:99.9%。
1H NMR(400MHz,DMSO-d6)δ0.34(s,6H),3.23(m,2H),4.53–4.69(m,2H),6.44(m,1H),6.80(m,1H),6.87(t,1H),6.99–7.07(m,2H),7.09–7.27(m,4H),7.32–7.53(m,15H),7.56–7.68(m,3H),7.77(t,1H),7.84(d,1H).
实施例11
化合物93的合成
除了起始原料更换为93-A、93-B、93-C和93-D以外,其他与实施例1相同。LC MS:M/Z762.27(M+)。合成总收率:39%;HPLC纯度:99.9%。
1H NMR(400MHz,DMSO-d6)δ2.95(m,2H),3.12(t,2H),7.03–7.11(m,2H),7.08–
7.18(m,2H),7.19(m,1H),7.23–7.76(m,25H),7.73–7.82(m,1H),8.17–8.27(m,2H),8.66(d,1H).
实施例12
化合物108的合成
除了起始原料更换为108-A、108-B、108-C和108-D以外,其他与实施例1相同。LCMS:M/Z 925.34(M+)。合成总收率:39%;HPLC纯度:99.9%。
1H NMR(400MHz,DMSO-d6)δ1.69(s,6H),3.70(d,4H),6.95–7.11(m,6H),7.13–7.42(m,15H),7.42–7.51(m,5H),7.51–7.56(m,1H),7.60–7.71(m,4H),7.78(t,1H),7.82–7.91(m,2H),8.17–8.24(m,3H).
实施例13
化合物112的合成
除了起始原料更换为112-A、112-B、112-C和112-D以外,其他与实施例1相同。LCMS:M/Z 937.39(M+)。合成总收率:38%;HPLC纯度:99.9%。
1H NMR(400MHz,DMSO-d6)δ2.72(m,2H),3.70(m,2H),4.59(d,2H),7.03–7.10(m,6H),7.10–7.61(m,28H),7.66–7.80(m,7H),7.82–7.94(m,2H),7.94–8.02(m,1H),8.69(d,1H).
实施例14
化合物117的合成
除了起始原料更换为117-A、117-B、117-C和117-D以外,其他与实施例1相同。LCMS:M/Z 779.41(M+)。合成总收率:38%;HPLC纯度:99.9%。
1H NMR(400MHz,DMSO-d6)δ1.15–1.25(m,4H),1.27–1.55(m,10H),1.90(m,2H),2.15(m,2H),2.72(m,2H),3.70(m,2H),4.59(d,2H),7.05(m,1H),7.14(m,1H),7.17–
7.28(m,3H),7.24–7.43(m,6H),7.43–7.79(m,12H),7.80–7.94(m,3H),7.99–8.07(m,1H),8.27(d,1H),8.73–8.81(m,1H).
实施例15
化合物129的合成
除了起始原料更换为129-A、129-B、129-C和129-D以外,其他与实施例1相同。LCMS:M/Z 890.46(M+)。合成总收率:37%;HPLC纯度:99.9%。
1H NMR(400MHz,DMSO-d6)δ1.22(d,12H),1.48(s,4H),1.69(s,6H),6.67(m,1H),7.07–7.66(m,29H),7.66–7.76(m,1H),7.73–7.82(m,1H),7.78–7.88(m,1H),7.94(d,1H),8.16–8.28(m,2H).
实施例16
化合物130的合成
除了起始原料更换为130-A、130-B、130-C和130-D以外,其他与实施例1相同。LCMS:M/Z 867.44(M+)。合成总收率:39%;HPLC纯度:99.9%。
1H NMR(400MHz,DMSO-d6)δ1.22(d,12H),1.48(s,4H),1.69(s,6H),6.67(m,1H),7.14–7.58(m,24H),7.66–7.80(m,6H),7.87–7.99(m,3H),7.94–8.02(m,1H).
实施例17
化合物138的合成
除了起始原料更换为138-A、138-B、138-C和138-D以外,其他与实施例1相同。LCMS:M/Z 744.35(M+)。合成总收率:39%;HPLC纯度:99.9%。
1H NMR(400MHz,DMSO-d6)δ1.22(d,12H),6.34(d,1H),6.67(m,1H),7.04(m,1H),7.08–7.18(m,2H),7.18–7.27(m,2H),7.31–7.50(m,19H),7.50–7.58(m,1H),7.58–7.71(m,3H),7.67–7.79(m,2H),7.74–7.83(m,1H),7.95–8.03(m,1H),8.08–8.16(m,2H),8.16–8.25(m,2H).
实施例18
化合物140的合成
除了起始原料更换为140-A、140-B、140-C和140-D以外,其他与实施例1相同。LCMS:M/Z 793.43(M+)。合成总收率:40%;HPLC纯度:99.9%。
1H NMR(400MHz,DMSO-d6)δ1.22(d,12H),1.48(s,6H),1.69(s,6H),6.44(m,1H),6.67(m,1H),6.80(m,1H),6.87(t,1H),6.99–7.07(m,2H),7.08–7.53(m,19H),7.48–7.58(m,2H),7.77(t,1H),7.85(d,2H),8.60(t,1H).
实施例19
化合物164的合成
除了起始原料更换为164-A、164-B、164-C和164-D以外,其他与实施例1相同。LCMS:M/Z 941.43(M+)。合成总收率:39%;HPLC纯度:99.9%。
1H NMR(400MHz,DMSO-d6)δ1.48–1.67(m,4H),1.69(s,6H),1.90–2.02(m,2H),2.14–2.28(m,2H),4.83(s,2H),6.91(m,1H),6.95–7.01(m,1H),7.06(m,2H),7.16–7.58(m,27H),7.68(m,1H),7.73(d,1H),7.82–7.96(m,4H),7.96–8.01(m,1H),8.03(m,1H).
实施例20
化合物217的合成
除了起始原料更换为217-A、217-B、217-C和217-D以外,其他与实施例1相同。LCMS:M/Z 559.25(M+)。合成总收率:38%;HPLC纯度:99.9%。
1H NMR(400MHz,DMSO-d6)δ1.62–1.83(m,4H),2.78–2.88(m,2H),4.14–4.22(m,2H),7.00(m,2H),7.08(m,6H),7.10–7.24(m,2H),7.20–7.29(m,5H),7.32–7.45(m,5H),7.57–7.66(m,2H),7.69(m,1H),7.77(t,1H),8.66(d,1H).
实施例21
化合物271的合成
除了起始原料更换为271-A、271-B、271-C和271-D以外,其他与实施例1相同。LCMS:M/Z 695.36(M+)。合成总收率:38%;HPLC纯度:99.9%。
1H NMR(400MHz,DMSO-d6)δ1.69(s,6H),1.87–2.08(m,4H),2.63–2.89(m,9H),7.00(m,2H),7.04–7.12(m,4H),7.15–7.34(m,8H),7.43–7.53(m,3H),7.56(t,2H),7.66(m,1H),7.87–7.97(m,2H),8.07(m,1H),8.80–8.88(m,1H),8.95(m,1H),9.07(d,1H).
实施例22
化合物286的合成
除了起始原料更换为286-A、286-B、286-C和286-D以外,其他与实施例1相同。LCMS:M/Z 799.35(M+)。合成总收率:39%;HPLC纯度:99.9%。
1H NMR(400MHz,DMSO-d6)δ1.93–2.08(m,4H),2.63–2.74(m,2H),2.70–2.80(m,2H),2.84(m,4H),4.10–4.21(m,2H),4.21–4.32(m,2H),7.05–7.14(m,2H),7.26–
7.39(m,7H),7.39–7.50(m,5H),7.50–7.62(m,5H),7.67–7.83(m,78H),8.19(d,1H),8.26(m,2H).
实施例23
化合物293的合成
除了起始原料更换为293-A、293-B、293-C和293-D以外,其他与实施例1相同。LCMS:M/Z 619.24(M+)。合成总收率:39%;HPLC纯度:99.9%。
1H NMR(400MHz,DMSO-d6)δ1.40–1.56(m,4H),1.66–1.82(m,4H),2.41(d,4H),2.70(m,4H),6.00(d,1H),6.93(d,1H),7.00(m,1H),7.04–7.11(m,2H),7.14(d,1H),7.18–7.33(m,3H),7.34–7.54(m,10H),7.76–7.88(m,2H).
实施例24
化合物418的合成
除了起始原料更换为418-A、418-B、418-C和418-D以外,其他与实施例1相同。LCMS:M/Z 635.21(M+)。合成总收率:39%;HPLC纯度:99.9%。
1H NMR(400MHz,DMSO-d6)δ5.12(d,2H),6.91(m,1H),7.00(m,1H),7.04–7.11(m,2H),7.14(d,1H),7.20–7.60(m,16H),7.65–7.76(m,2H),7.72–7.79(m,2H),7.92–
8.01(m,2H),8.01–8.06(m,1H).
实施例25
化合物428的合成
除了起始原料更换为428-A、428-B、428-C和428-D以外,其他与实施例1相同。LCMS:M/Z 739.31(M+)。合成总收率:38%;HPLC纯度:99.9%。
1H NMR(400MHz,DMSO-d6)δ0.34(s,6H),5.12(s,2H),6.44(m,1H),6.80(m,1H),6.87(t,1H),6.99–7.07(m,2H),7.09–7.27(m,4H),7.30–7.61(m,18H),7.64(m,1H),7.71–7.80(m,3H),7.77–7.86(m,2H),7.88(m,1H).
器件实施例1:有机电致发光器件的制备
制备工艺为:在玻璃材质的基底上,形成透明阳极ITO膜层(厚度150nm),得到第一电极作为阳极。随后通过真空蒸镀的方法,在阳极表面蒸镀化合物T-1与化合物T-2的混合材料作为空穴注入层,混合比例为3:97(质量比),厚度为10nm。随后在空穴注入层上蒸镀100nm厚度的化合物T-2,得到第一层空穴传输层。随后在第一空穴传输层上蒸镀10nm厚度的本发明化合物1,得到第二层空穴传输层。在第二空穴传输层上,将化合物T-3和化合物T-4以95:5的质量比进行共蒸镀,形成厚度为40nm的有机发光层。然后,在有机发光层上,依次蒸镀化合物T-5形成空穴阻挡层(厚度10nm),以及混合比例为4:6(质量比)的化合物T-6和LiQ形成电子传输层(厚度30nm)。最后将镁(Mg)和银(Ag)以1∶9的蒸镀速率混合,真空蒸镀在电子注入层层上,作为第二电极109,完成有机发光器件的制造。
器件实施例2-20
除了在形成第二空穴传输层时,分别以化合物4、5、8、13、15、30、43、59、68、93、108、112、117、129、130、138、140、164、217、271、286、293、418和428替代化合物1外,采用与器件实施例1相同的方法制作有机电致发光器件。
器件对比例1-2
除了在形成第二空穴传输层时,分别以化合物HT-1、化合物HT-2替代化合物1外,采用与器件实施例1相同的方法制作有机电致发光器件。
对以上制得的有机电致发光器件,通过计算机控制的Keithley 2400测试系统计算得到工作电压和效率。使用配备电源和光电二极管作为检测单元的Polaronix(McScience Co.)寿命测量系统得到黑暗条件下的器件寿命。每一组器件实施例和器件对比例1均与器件对比例2的器件在同一批次中产出并测试,将器件对比例1的器件的工作电压、效率和寿命均分别记为1,并分别计算器件实施例1-25、器件对比例的与器件对比例1相应指标的比值,如表1所示。
表1:器件实施例1-25及器件对比例1-2的测试结果
根据表1的结果可知,作发光器件的第二空穴传输层时,器件实施例1-25所使用的化合物与器件对比例1-2中使用的化合物形成的器件相比,电压均有所降低,发光效率均有所提高(最高达到20%),寿命提高显著。
据此,本发明的化合物应用到有机光电器件能使器件具有较高的空穴迁移率,并且能够有效的阻挡电子、激子进入到空穴传输层中,从而提高器件的效率,同时分子具有高的稳定性,能进一步提升器件的发光效率和使用寿命。
综上所述,本发明的化合物在有机光电器件中具有较大的应用价值。
以上所述,仅为本发明较佳的具体实施方式,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,根据本发明的技术方案及其发明构思加以等同替换或改变,都应涵盖在本发明的保护范围之内。
Claims (14)
1.一种化合物,其化学结构如式(Ⅰ)所示:
式(Ⅰ)中,A选自如下基团中至少一种:
Z1-Z75各自独立选自C(R3R4)、N(R5)、Si(R6R7)、B(R8)、O或S;
X选自C(R9R10)、N(R11)、Si(R12R13)、B(R14)、O或S;
R1-R14相同或不同,各自独立地选自氢、氘、取代或未取代的直链或支链的C1-C30的烷基、取代或未取代的C1-C30的杂烷基、取代或未取代的C3-C30的环烷基、取代或未取代的C3-C30的杂环烷基、取代或未取代的C6-C30的芳基、或取代或未取代的C6-C30的杂芳基;
L1-L3相同或不同,各自独立地选自单键、取代或未取代的C6-C30的亚芳基、取代或未取代的C3-C30的亚杂芳基;
Ar1和Ar2相同或不同,各自独立选自取代或未取代的C6-C30的芳基、取代或未取代的C5-C30的杂芳基。
2.根据权利要求1所述的化合物,其特征在于,基团A选自如下所示基团中至少一种:
其中,R16-R23各自独立选自选自氢、氘、取代或未取代的C1-C60的烷基、取代或未取代的C1-C60的环烷基、取代或未取代的C1-C60的杂烷基、取代或未取代的C1-C60的杂环烷基、取代或未取代的C1-C60的芳基或取代或未取代的C1-C60的杂芳基;*为连接位点。
3.根据权利要求1所述的化合物,其特征在于,基团A选自如下所示基团中至少一种:
Ar3选自取代或未取代的C6-C30的芳基、取代或未取代的C5-C30的杂芳基。
4.根据权利要求3所述的化合物,其特征在于,基团A中与Ar3形成并环的烷基选自如下结构中至少一种:
其中,RC选自C6-C30芳基、C5-C30杂芳基。
5.根据权利要求1所述的化合物,其特征在于,R1、R2各自独立选自氢、氘;
和/或,R3-R13相同或不同,各自独立地选自氢、氘、取代或未取代的直链或支链的C1-C30的烷基、取代或未取代的C1-C12的烷氧基、取代或未取代的C1-C12的烷硫基、取代或未取代的C3-C30的环烷基、取代或未取代的C3-C30的杂环烷基、取代或未取代的C6-C30的芳基、或取代或未取代的C6-C30的杂芳基。
6.根据权利要求1所述的化合物,其特征在于,L1-L3各自独立选自单键、取代或未取代的亚苯基、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚三联苯基、取代或未取代的亚蒽基、取代或未取代的亚菲基,或者选自如下取代基:
7.根据权利要求1所述的化合物,其特征在于,Ar1、Ar2各自独立选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的三联苯基,或者选自如下取代基:
8.根据权利要求1所述的化合物,其特征在于,X1、X2各自独立选自O、S或如下结构中的一种:
其中,Y1-Y23选自N(R24)、C(R25R26)、或Si(R27R28)、O或S;
Ar4和Ar5选自取代或未取代的C6-C30的芳基、取代或未取代的C5-C30的杂芳基;
R24-R28各自独立选自选自氢、氘、取代或未取代的C1-C60的烷基、取代或未取代的C1-C60的环烷基、取代或未取代的C1-C60的杂烷基、取代或未取代的C1-C60的杂环烷基、取代或未取代的C1-C60的芳基、或取代或未取代的C1-C60的杂芳基;*为原子的连接位点。
9.根据权利要求1所述的化合物,其特征在于,所述化合物选自以下化学结构中至少一种:
10.权利要求1-9任一项所述化合物在有机光电器件中的应用。
11.一种有机层,包括权利要求1-9任一项所述化合物中的一种或多种。
12.一种有机光电器件,其包括第一电极、第二电极和权利要求11所述的有机层,其中,所述有机层为空穴注入层、空穴传输层、发光层、电子注入层或电子传输层中至少一层。
13.根据权利要求12所述的有机光电器件,其特征在于,所述有机光电器件为有机光伏器件、有机发光器件、有机太阳电池、电子纸、有机感光体、有机薄膜晶体管中至少一种。
14.一种显示或照明装置,其包括权利要求12或13所述的有机光电器件。
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