CN113582925B - 含氰基取代荧蒽衍生物的化合物和包含其的有机电致发光器件 - Google Patents
含氰基取代荧蒽衍生物的化合物和包含其的有机电致发光器件 Download PDFInfo
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- CN113582925B CN113582925B CN202111059982.8A CN202111059982A CN113582925B CN 113582925 B CN113582925 B CN 113582925B CN 202111059982 A CN202111059982 A CN 202111059982A CN 113582925 B CN113582925 B CN 113582925B
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- C07D213/02—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
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- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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Abstract
本发明公开了含氰基取代荧蒽衍生物的化合物和包含其的有机电致发光器件，具有如下化学结构：
R1–R10各自独立为氢、氘、取代或未取代的碳原子数为1–20的烷基或烷氧基、取代或未取代的成环碳原子数为6–30的芳基、取代或未取代的成环碳原子数为5–30的杂芳基，或与相邻基团结合形成取代或未取代的环；L为单键、取代或未取代的成环碳原子数为6–30的亚芳基或成环碳原子数为5–30的亚杂芳基，Ar1为取代或未取代的芳基或杂芳基。本发明的化合物通过氰基取代荧蒽衍生物，同时连接芳香或杂芳基“吸电子”基团，具有较好的稳定性、抗结晶性和较高迁移率，作为电子传输材料可以提高有机电致发光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，具体涉及含氰基取代荧蒽衍生物的化合物和包含其的有机电致发光器件。
背景技术
目前，有机电致发光器件(OLED)的电子传输材料要求具有快速的电子传输能力、合适的能级以及较好的抗结晶性。为了获得这些性能，往往会加入一些“吸电子”基团，比如三嗪、吡啶、苯并咪唑、菲咯啉或者嘧啶等杂芳基。但是，上述杂芳基对能级的调控和传输能力非常有限，为了获得更好的电子传输能力，加入更强的吸电子基团如氰基，而氰基的强吸电子性能使得分子偶极矩过大，分子的稳定性变差。基于此，本发明提出一种含氰基取代荧蒽衍生物的化合物，具体如下所述。
发明内容
本发明提供一种含氰基取代荧蒽衍生物的化合物，具有如化学式1所示的化学结构：
在化学式1中，n＝1或2；
R1–R10各自独立为氢、氘、取代或未取代的碳原子数为1–20的烷基或烷氧基、取代或未取代的成环碳原子数为6–30的芳基、取代或未取代的成环碳原子数为5–30的杂芳基，或者与相邻基团结合形成取代或未取代的环；
L为单键、取代或未取代的成环碳原子数为6–30的亚芳基、取代或未取代的成环碳原子数为5–30的亚杂芳基；
Ar1为取代或未取代的成环碳原子数为6–30的芳基、取代或未取代的成环碳原子数为5–30的杂芳基。
与现有技术相比，本发明的有益效果在于：本发明中含氰基取代荧蒽衍生物的化合物通过氰基取代荧蒽衍生物，同时连接芳香或杂芳基类“吸电子”基团，具有较好的稳定性、抗结晶性和较高迁移率，作为电子传输材料可以提升OLED的发光效率和稳定性。
附图说明
图1是实施例中底部发光有机电致发光器件的结构示意图。
图2是实施例中顶部发光有机电致发光器件的结构示意图。
图3是本发明中含氰基取代荧蒽衍生物的化合物作为电子传输材料用于串联有机电致发光器件的结构示意图。
具体实施方式
为使本发明实施例的目的、技术方案和优点更加清楚，下面将结合本发明实施例的附图，对本发明实施例的技术方案进行清楚、完整地描述。显然，所描述的实施例是本发明的一部分实施例，而不是全部的实施例。基于所描述的本发明的实施例，本领域普通技术人员在无需创造性劳动的前提下所获得的所有其它实施例，都属于本发明保护的范围。
本发明提供的一种含氰基取代荧蒽衍生物的化合物，具有如化学式1所示的化学结构：
在化学式1中，n＝1或2；
R1–R10各自独立为氢、氘、取代或未取代的碳原子数为1–20的烷基或烷氧基、取代或未取代的成环碳原子数为6–30的芳基、取代或未取代的成环碳原子数为5–30的杂芳基，或者与相邻基团结合形成取代或未取代的环；
L为单键、取代或未取代的成环碳原子数为6–30的亚芳基、取代或未取代的成环碳原子数为5–30的亚杂芳基；
Ar1为取代或未取代的成环碳原子数为6–30的芳基、取代或未取代的成环碳原子数为5–30的杂芳基。
化学式1所示的含氰基取代荧蒽衍生物的化合物中取代基的描述如下，当不限于此。
“取代或未取代的”指选自以下一个或多个取代基取代：氢、氘、卤素基、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、芳基胺基和杂环基，或未取代；或者连接以上取代基中的两个或多个取代基的取代基取代，或未取代，如“连接两个或多个取代基的取代基”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。
“芳基”可为单环芳基或多环芳基，单环芳基包括苯基、联苯基、三联苯基、四联苯基、五联苯基，多环芳基包括萘基、蒽基、菲基、芘基、苝基、芴基，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。
根据一些实施方式，在化学式1中，Ar1选自以下任一个基团：吡啶基、联吡啶基、三联吡啶基、嘧啶基、三嗪基、哒嗪基、吡嗪基、苯并哒嗪基、苯并吡嗪基、苯并嘧啶基、吡啶并嘧啶基、吡啶并吡嗪基、唑基、二唑基、三唑基、噻吩基、呋喃基、苯并呋喃基、苯并噻吩基、二苯并呋喃基、二萘并呋喃基、二苯并噻吩基、氧化膦基、吡咯基、咪唑基、噻唑基、吖啶基、喹啉基、苯并喹啉基、喹唑啉基、喹喔啉基、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、苯并喹唑啉基、吡啶并喹唑啉基、嘧啶并喹唑啉基、菲咯啉基、苯并噻唑基、异恶唑基、噻二唑基、吩噻嗪基、氮丙啶基、氮杂吲哚基、异吲哚基、吲唑基、吡唑基、嘌呤基、蝶啶基、β-咔啉基、萘啶基、吩嗪基、咪唑并吡啶基、氮杂基、硼烷基。
根据一些实施方式，化学式1所示的含氰基取代荧蒽衍生物的化合物选自以下任一个化学结构：
以下合成实施例1至8详细描述了含氰基取代荧蒽衍生物的化合物A1、A8、A15、A23、A24、A28、A39、A52的制备方法，未注明制备方法的原料均为市售商品，本发明中其他化合物的合成与合成实施例1至8类似。
合成实施例1
本合成实施例中合成化合物A1，技术路线如下所示：
A1-3的合成：在500mL三口烧瓶，依次加入A1-1(15g，47.2mmol)、A1-2(12.8g，47.2mmol)、K2CO3(13g，94.4mmol)、四(三苯基膦)钯(Pd(PPh3)4)(1.1g，0.94mmol)，再加入150mL甲苯、30mL乙醇和30mL水，体系氮气置换3次，反应液升温至回流，继续搅拌反应4小时。反应液冷却至70℃，静置分液，上层有机相加60mL水洗涤，分液，上层有机相过硅胶柱。有机相浓缩至甲苯约50mL，逐渐加入150mL石油醚，有固体析出，搅拌2小时，抽滤，用少量石油醚洗涤滤饼，用50mL甲苯与120mL乙醇的混合溶液加热40℃搅拌2小时，固体进行过滤，烘干，获得A1-3化合物17g，收率77％。
A1的合成：在500mL三口烧瓶，依次加入A1-3(15g，32.3mmol)、A1-4(8.9g，32.3mmol)、K2CO3(8.9g，64.6mmol)、四(三苯基膦)钯(Pd(PPh3)4)(0.75g，0.65mmol)，再加入120mL甲苯、24mL乙醇和24mL水，体系氮气置换3次，反应液升温至回流，继续搅拌反应4小时。反应液冷却至70℃，静置分液，上层有机相加50mL水洗涤，分液，上层有机相过硅胶柱，有机相浓缩至甲苯约40mL，逐渐加入120mL石油醚，有固体析出，搅拌2小时，抽滤，用少量石油醚洗涤滤饼，用60mL甲苯与120mL乙醇的混合溶液进行加热40℃搅拌2小时，固体进行过滤，烘干，获得A1化合物16g，收率74％。
合成实施例2
本合成实施例中合成化合物A8，技术路线如下所示：
A8-3的合成：以与合成实施例1中的化合物A1-3相同的方式获得化合物A8-3(19g，产率73％)，不同之处在于使用化合物A8-1替代化合物A1-1，将化合物A8-2替代化合物A1-2。
A8的合成：以与合成实施例1中的化合物A1相同的方式获得化合物A8(15g，产率72％)，不同之处在于使用化合物A8-3替代化合物A1-3。
合成实施例3
本合成实施例中合成化合物A15，技术路线如下所示：
A15-3的合成：以与合成实施例1中的化合物A1-3相同的方式获得化合物A15-3(17g，产率73％)，不同之处在于使用化合物A15-1替代化合物A1-1，将化合物A15-2替代化合物A1-2。
A15的合成：以与合成实施例1中的化合物A1相同的方式获得化合物A15(14g，产率66％)，不同之处在于使用化合物A15-3替代化合物A1-3，使用化合物A15-4替代化合物A1-4。
合成实施例4
本合成实施例中合成化合物A23，技术路线如下所示：
A23-3的合成：以与合成实施例1中的化合物A1-3相同的方式获得化合物A23-3(18g，产率74％)，不同之处在于使用化合物A23-1替代化合物A1-1。
A23的合成：以与合成实施例1中的化合物A1相同的方式获得化合物A23(18g，产率73％)，不同之处在于使用化合物A23-3替代化合物A1-3，使用化合物A23-4替代化合物A1-4。
合成实施例5
本合成实施例中合成化合物A24，技术路线如下所示：
A24-3的合成：以与合成实施例1中的化合物A1-3相同的方式获得化合物A24-3(17g，产率69％)，不同之处在于使用化合物A24-1替代化合物A1-1。
A24的合成：以与合成实施例1中的化合物A1相同的方式获得化合物A24(14g，产率70％)，不同之处在于使用化合物A24-3替代化合物A1-3，使用化合物A24-4替代化合物A1-4。
合成实施例6
本合成实施例中合成化合物A28，技术路线如下所示：
A28-3的合成：以与合成实施例1中的化合物A1-3相同的方式获得化合物A28-3(16g，产率75％)，不同之处在于使用化合物A28-1替代化合物A1-1。
A28的合成：以与合成实施例1中的化合物A1相同的方式获得化合物A28(16g，产率73％)，不同之处在于使用化合物A28-3替代化合物A1-3，使用化合物A28-4替代化合物A1-4。
合成实施例7
本合成实施例中合成化合物A39，技术路线如下所示：
A39的合成：以与合成实施例1中的化合物A1相同的方式获得化合物A39(16g，产率76％)，不同之处在于使用化合物A39-1替代化合物A1-3，使用化合物A39-2替代化合物A1-4。
合成实施例8
本合成实施例中合成化合物A52，技术路线如下所示：
A52-3的合成：以与合成实施例1中的化合物A1-3相同的方式获得化合物A52-3(18g，产率73％)，不同之处在于使用化合物A52-1替代化合物A1-1，使用化合物A52-2替代化合物A1-2。
A52的合成：以与合成实施例1中的化合物A1相同的方式获得化合物A52(17g，产率73％)，不同之处在于使用化合物A52-3替代化合物A1-3，使用化合物A52-4替代化合物A1-4。
本发明还提供上述含氰基取代荧蒽衍生物的化合物在有机电致发光器件中的应用，具体是该化合物作为有机电致发光器件的电子传输材料。以下器件实施例制备的有机电致发光器件，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材料层，为底部或顶部发光器件结构(如图1或2所示)，其有机材料层可为单层结构，也可为层合有两个或多个有机材料层的多层串联结构(如图3所示)，如具有包括空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等作为有机材料层的结构，可使用制备有机电致发光器件的常见方法和材料来制备。本发明中上述含氰基取代荧蒽衍生物的化合物可以在红光、绿光、蓝光、白光等各种光色中使用，以下器件实施例1至8分别采用上述化合物A1、A8、A15、A23、A24、A28、A39和A52作为电子传输材料。
器件实施例1
按照如图1所示的结构制作单蓝色底部发光非串联有机电致发光器件，制备工艺为：在玻璃材质的基底101上，形成透明阳极ITO膜层，膜厚150nm，得到第一电极102作为阳极，之后蒸镀
与化合物/>
的混合材料作为空穴注入层103，混合比例为3:97(质量比)，之后蒸镀100nm厚度的化合物/>
得到第一层空穴传输层104，然后蒸镀20nm厚度化合物/>
得到第二层空穴传输层105，然后以95:5的蒸镀速率蒸镀/>
与/>
30nm，制作蓝光发光单元106，然后蒸镀10nm/>
形成电子阻挡层107，然后蒸镀本发明的化合物A1与/>
混合比例为4:6(质量比)形成厚度30nm的电子传输层108，之后蒸镀形成厚度1nm的金属镱，再形成100nm的金属银作为双层镱/银金属作为第二电极109。
器件实施例2至8中分别采用上述化合物A8、A15、A23、A24、A28、A39、A52以及对比例1和2中分别采用化合物
替代器件实施例1中化合物A1作为电子传输层108来制作蓝光有机电致发光器件，得到的有机电致发光器件进行发光效率性能测试，如表1所示。
表1
从表1可以看出，本发明中含氰基取代荧蒽衍生物的化合物作为蓝色底部发光的非串联有机电致发光器件的电子传输层材料，得到的器件驱动电压低、发光效率高且使用寿命长。
此外，本发明中含氰基取代荧蒽衍生物的化合物还可以作为如图2所示的顶部发光器件的电子传输层108，或者作为如图3所示的串联有机电致发光器件的第一电子传输层108、第二电子传输层114……，得到的器件效果同样显著。
另外，本发明还提供包含上述任一有机电致发光器件的显示装置。
Claims (3)
1.含氰基取代荧蒽衍生物的化合物，其特征在于，选自以下任一个化学结构：
2.一种有机电致发光器件，包含权利要求1所述含氰基取代荧蒽衍生物的化合物，所述含氰基取代荧蒽衍生物的化合物作为有机电致发光器件的电子传输材料。
3.一种显示装置，其特征在于，包含权利要求2所述有机电致发光器件。
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