CN114989815A - 主体化合物与掺杂剂化合物的组合以及有机电致发光装置 - Google Patents
主体化合物与掺杂剂化合物的组合以及有机电致发光装置 Download PDFInfo
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Abstract
主体化合物与掺杂剂化合物的组合以及有机电致发光装置。本文公开了一种或多种由下式1表示的掺杂剂化合物与一种或多种由下式2表示的主体化合物的一种组合:
Description
本发明专利申请是国际申请号为PCT/KR2015/011793,国际申请日为2015年11月4日,进入中国国家阶段的申请号为201580056542.3,名称为“主体化合物与掺杂剂化合物的新颖组合以及包含其的有机电致发光装置”的发明专利申请的分案申请。
技术领域
本发明涉及主体化合物与掺杂剂化合物的新颖组合以及包含其的有机电致发光装置。
背景技术
电致发光装置(EL装置)是一种自发光装置,其优点在于其提供较宽的视角、较大的对比率和较快的响应时间。第一有机EL装置由Eastman Kodak通过使用小芳香族二胺分子和铝络合物作为用于形成发光层的材料而加以开发[应用物理学报(Appl.Phys.Lett.)51,913,1987]。
决定有机EL装置中发光效率的最重要因素是发光材料。根据于其功能,发光材料可分类为主体材料和掺杂剂材料。一般来说,显示最好的电致发光特征的装置具有包含发光层的结构,在该发光层中掺杂剂掺杂于主体中。近来,开发具有高效率和长使用寿命的有机EL装置是十分紧迫的问题。具体来说,考虑OLED的中等或大尺寸面板的EL特征需求,必须迫切地开发比常规材料显示更好特征的材料。
迄今为止,已广泛使用荧光材料作为发光材料。然而,考虑到电致发光机制,磷光材料的开发是一种理论上使发光效率提高四(4)倍的最好方式。铱(III)络合物已广泛地被称为磷光掺杂剂化合物,包括分别作为红光、绿光和蓝光材料的双(2-(2'-苯并噻吩基)-吡啶根-N,C-3')(乙酰丙酮酸)铱((acac)Ir(btp)2)、三(2-苯基吡啶)铱(Ir(ppy)3)和双(4,6-二氟苯基吡啶根-N,C2)吡啶甲甲酰合铱(Firpic)。目前,4,4'-N,N'-二咔唑-联苯(CBP)是最广为人知的磷光主体化合物。公开了一种高性能有机EL装置,其使用浴铜灵(BCP)和双(2-甲基-8-喹啉)(4-苯基苯酚)铝(III)(BAlq)等的空穴阻挡层。然而,当应用包含常规掺杂剂和主体化合物的发光材料时,功率效率较差且使用寿命和发光效率不令人满意。
国际公开案第WO 2008/109824 A2号和第WO 2010/033550 A1号、美国申请公开案第US 2010/0090591 A1号和第US 2012/0181511 A1号,以及韩国专利申请公开第KR 2011-0086021 A号公开了具有苯基喹啉配位体的铱络合物作为有机EL装置的发光材料中含有的掺杂剂化合物。然而,它们未能具体公开包含作为掺杂剂化合物的具有苯基喹啉配位体的铱络合物,和作为主体化合物的经5到11元含氮杂芳基取代的咔唑衍生物的有机EL装置。
发明内容
待解决的问题
本发明的目的是提供具有优异发光效率和使用寿命的主体和掺杂剂的新颖组合,以及包含其的有机电致发光装置。
问题的解决方案
本发明人发现以上目标可通过一种或多种由下式1表示的掺杂剂化合物和一种或多种由下式2表示的主体化合物的组合,和包含其的有机电致发光装置实现。
其中
R1和R2各自独立地表示氢、氘、卤素、经取代或未经取代的(C1-C6)烷基,或经取代或未经取代的(C6-C30)芳基;且
a和b各自独立地表示1到4的整数;其中a或b为2或更大的整数,R1中的每个和R2中的每个可相同或不同。
其中
Ma表示经取代或未经取代的5到11元含氮杂芳基;
La表示单键、经取代或未经取代的(C6-C30)亚芳基,或经取代或未经取代的3到30元亚杂芳基;
Xa到Xh各自独立地表示氢、氘、卤素、氰基、经取代或未经取代的(C1-C30)烷基、经取代或未经取代的(C2-C30)烯基、经取代或未经取代的(C2-C30)炔基、经取代或未经取代的(C3-C30)环烷基、经取代或未经取代的(C6-C60)芳基、经取代或未经取代的3到30元杂芳基、经取代或未经取代的三(C1-C30)烷基硅烷基、经取代或未经取代的三(C6-C30)芳基硅烷基、经取代或未经取代的二(C1-C30)烷基(C6-C30)芳基硅烷基、经取代或未经取代的(C1-C30)烷基二(C6-C30)芳基硅烷基,或经取代或未经取代的单或二(C6-C30)芳氨基;或彼此键联以形成经取代或未经取代的单环或多环、(C3-C30)脂环族环或芳香族环,其(一个或多个)碳原子可由至少一个选自氮、氧和硫的杂原子替换;
(亚)杂芳基含有至少一个选自B、N、O、S、Si和P的杂原子。
本发明的有利作用
根据本发明,提供了一种具有优异发光效率和使用寿命的有机电致发光装置。
具体实施方式
在下文中,将对本发明进行详细描述。然而,以下描述旨在解释本发明,并且不打算以任何方式限制本发明的范围。
本发明涉及包含一种或多种由式1表示的掺杂剂化合物和一种或多种由式2表示的主体化合物的有机电致发光装置。
在以上式1中,R1和R2各自独立地表示氢、氘、卤素、经取代或未经取代的(C1-C6)烷基,或经取代或未经取代的(C6-C30)芳基;优选地各自独立地表示氢、卤素、经取代或未经取代的(C1-C6)烷基,或经取代或未经取代的(C6-C12)芳基;并且更优选地各自独立地表示氢、卤素、未经取代的(C1-C6)烷基,或未经取代或经卤素或(C1-C6)烷基取代的(C6-C12)芳基。
在以上式2中,La表示单键、经取代或未经取代的(C6-C30)亚芳基,或经取代或未经取代的3到30元亚杂芳基;优选地表示单键、经取代或未经取代的(C6-C12)亚芳基,或经取代或未经取代的5到15元亚杂芳基;并且更优选地表示单键、未经取代或经三(C6-C10)芳基硅烷基或(C6-C12)芳基取代的(C6-C12)亚芳基,或未经取代的6到15元亚杂芳基。
另外,La可表示单键、亚咔唑基,或以下式3到式15中的一者:
其中
Xi到Xp各自独立地表示氢、氘、卤素、氰基、经取代或未经取代的(C1-C30)烷基、经取代或未经取代的(C2-C30)烯基、经取代或未经取代的(C2-C30)炔基、经取代或未经取代的(C3-C30)环烷基、经取代或未经取代的(C6-C60)芳基、经取代或未经取代的3到30元杂芳基、经取代或未经取代的三(C1-C30)烷基硅烷基、经取代或未经取代的三(C6-C30)芳基硅烷基、经取代或未经取代的二(C1-C30)烷基(C6-C30)芳基硅烷基、经取代或未经取代的(C1-C30)烷基二(C6-C30)芳基硅烷基,或经取代或未经取代的单或二(C6-C30)芳氨基;或彼此键联以形成经取代或未经取代的单环或多环、(C3-C30)脂环族环或芳香族环,其(一个或多个)碳原子可由至少一个选自氮、氧和硫的杂原子替换;优选地,各自独立地表示氢、氰基、经取代或未经取代的(C6-C15)芳基、经取代或未经取代的10到20元杂芳基,或经取代或未经取代的三(C6-C10)芳基硅烷基;并且更优选地各自独立地表示氢、氰基、未经取代或经三(C6-C10)芳基硅烷基取代的(C6-C15)芳基,或未经取代或经(C6-C15)芳基取代的10到20元杂芳基。
在以上式2中,Ma表示经取代或未经取代的5到30元含氮杂芳基;优选地表示经取代或未经取代的6到10元含氮杂芳基;并且更优选地表示经选自由以下各者组成的群组的取代基取代的6到10元含氮杂芳基:未经取代的(C6-C25)芳基、经氰基取代的(C6-C12)芳基、经(C1-C6)烷基取代的(C6-C12)芳基、经三(C6-C12)芳基硅烷基取代的(C6-C12)芳基、未经取代的6到15元杂芳基和经(C6-C12)芳基取代的6到15元杂芳基。
另外,Ma可表示单环型杂芳基如经取代或未经取代的吡咯基、经取代或未经取代的咪唑基、经取代或未经取代的吡唑基、经取代或未经取代的三嗪基、经取代或未经取代的四嗪基、经取代或未经取代的三唑基、经取代或未经取代的四唑基、经取代或未经取代的吡啶基、经取代或未经取代的吡嗪基、经取代或未经取代的嘧啶基、经取代或未经取代的哒嗪基等,或稠环型杂芳基如经取代或未经取代的苯并咪唑基、经取代或未经取代的异吲哚基、经取代或未经取代的吲哚基、经取代或未经取代的吲唑基、经取代或未经取代的苯并噻二唑基、经取代或未经取代的喹啉基、经取代或未经取代的异喹啉基、经取代或未经取代的噌啉基、经取代或未经取代的喹唑啉基、经取代或未经取代的萘啶基、经取代或未经取代的喹喏啉基、经取代或未经取代的咔唑基、经取代或未经取代的啡啶基等。优选地,Ma可表示经取代或未经取代的三嗪基、经取代或未经取代的嘧啶基、经取代或未经取代的吡啶基、经取代或未经取代的喹啉基、经取代或未经取代的异喹啉基、经取代或未经取代的喹唑啉基、经取代或未经取代的萘啶基或经取代或未经取代的喹喏啉基。在Ma中,经取代的吡咯基等的取代基可为(C6-C25)芳基、经氰基取代的(C6-C12)芳基、经(C1-C6)烷基取代的(C6-C12)芳基、经三(C6-C12)芳基硅烷基的(C6-C12)芳基、氰基、(C1-C6)烷基、三(C6-C12)芳基硅烷基、6到15元杂芳基,或经(C6-C12)芳基取代的6到15元杂芳基;并且具体地说,可为氰基、(C1-C6)烷基、苯基、联苯基、联三苯基、萘基、苯基萘基、萘基苯基、二苯基芴、菲基、蒽基、二苯并噻吩基、二苯并呋喃基,或未经取代或经氰基、(C1-C6)烷基或三苯基硅烷基取代的苯基咔唑基。
在以上式2中,Xa到Xh各自独立地表示氢、氘、卤素、氰基、经取代或未经取代的(C1-C30)烷基、经取代或未经取代的(C2-C30)烯基、经取代或未经取代的(C2-C30)炔基、经取代或未经取代的(C3-C30)环烷基、经取代或未经取代的(C6-C60)芳基、经取代或未经取代的3到30元杂芳基、经取代或未经取代的三(C1-C30)烷基硅烷基、经取代或未经取代的三(C6-C30)芳基硅烷基、经取代或未经取代的二(C1-C30)烷基(C6-C30)芳基硅烷基、经取代或未经取代的(C1-C30)烷基二(C6-C30)芳基硅烷基,或经取代或未经取代的单或二(C6-C30)芳氨基;或彼此键联以形成经取代或未经取代的单环或多环、(C3-C30)脂环族环或芳香族环,其(一个或多个)碳原子可由至少一个选自氮、氧和硫的杂原子替换;且优选地,各自独立地表示氢、氰基、经取代或未经取代的(C6-C15)芳基、经取代或未经取代的10到20元杂芳基,或经取代或未经取代的三(C6-C10)芳基硅烷基;或彼此键联以形成经取代或未经取代的单环或多环、(C6-C20)芳香族环,其(一个或多个)碳原子可由至少一个选自氮、氧和硫的杂原子替换。更优选地,Xa到Xh各自独立地表示氢;氰基;未经取代或经10到20元杂芳基或三(C6-C10)芳基硅烷基取代的(C6-C15)芳基;未经取代或经(C6-C12)芳基或氰基(C6-C12)芳基取代的10到20元杂芳基;或未经取代的三(C6-C10)芳基硅烷基;或彼此键联以形成经取代或未经取代的苯、经取代或未经取代的吲哚、经取代或未经取代的苯并吲哚、经取代或未经取代的茚、经取代或未经取代的苯并呋喃或经取代或未经取代的苯并噻吩。
本文中,“(C1-C30)烷基”意指具有构成链的1到30个碳原子的直链或支链烷基,其中碳原子数目优选地为1到20个,更优选地1到10个,且包括甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基等;“(C2-C30)烯基”意指具有构成链的2到30个碳原子的直链或支链烯基,其中碳原子数目优选地为2到20个,更优选地2到10个,且包括乙烯基、1-丙烯基、2-丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、2-甲基丁-2-烯基等;“(C2-C30)炔基”意指具有构成链的2到30个碳原子的直链或支链炔基,其中碳原子数目优选地为2到20个,更优选地2到10个,且包括乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基戊-2-炔基等,“(C3-C30)环烷基”为具有3到30个环主链碳原子的单环或多环烃,其中碳原子数目优选地为3到20个,更优选地3到7个,且包括环丙基、环丁基、环戊基、环己基等;“3到7元杂环烷基”为具有3到7个(优选地5到7个)环主链原子的环烷基,其包括至少一个选自B、N、O、S、Si和P(优选地O、S和N)的杂原子,且包括四氢呋喃、吡咯啶、硫杂环戊烷、四氢吡喃等;“(C6-C30)(亚)芳基”为衍生自具有6到30个环主链碳原子的芳香族烃的单环或稠环,其中碳原子数目优选地为6到20个,更优选地6到15个,且包括苯基、联苯基、联三苯基、萘基、联萘基、苯基萘基、萘基苯基、茀基、苯基茀基、苯并茀基、二苯并茀基、菲基、苯基菲基、蒽基、茚基、联亚三苯基、芘基、并四苯基、苝基、屈基、稠四苯基、茀蒽基等;“3到30元杂芳基”为具有3到30个环主链原子,优选地3到20环主链原子,并且更优选地3到15个环主链原子的芳基,该杂芳基包括选自由以下各者组成的群组中的至少一个,优选地1到4个杂原子:B、N、O、S、Si和P;为单环或与至少一个苯环稠合的稠环;可为部分饱和的;可为通过经由(一个或多个)单键将至少一个杂芳基或芳基键联到杂芳基所形成的3到30元杂芳基;且包括单环型杂芳基和稠环型杂芳基,单环型杂芳基包括呋喃基、噻吩基、吡咯基、咪唑基、吡唑基、噻唑基、噻二唑基、异噻唑基、异噁唑基、噁唑基、噁二唑基、三嗪基、四嗪基、三唑基、四唑基、呋吖基、吡啶基、吡嗪基、嘧啶基、哒嗪基等,稠环型杂芳基包括苯并呋喃基、苯并噻吩基、异苯并呋喃基、二苯并呋喃基、二苯并噻吩基、苯并咪唑基、苯并噻唑基、苯并异噻唑基、苯并异噁唑基、苯并噁唑基、异吲哚基、吲哚基、苯并吲哚基、吲唑基、苯并噻二唑基、喹啉基、异喹啉基、噌啉基、喹唑啉基、喹喏啉基、咔唑基、啡噁嗪基、啡啶基、苯并间二氧杂环戊烯基等;“含氮5到30元杂芳基”为具有5到30个,优选地5到20个,并且更优选地5到15个环主链原子的包括至少一个杂原子N的芳基;为单环环或至少一个苯环稠合的稠环;可为部分饱和的;可为通过经由(一个或多个)单键将至少一个杂芳基或芳基键联到杂芳基所形成的含氮5到30元杂芳基;且包括单环型杂芳基和稠环型杂芳基,单环型杂芳基包括吡咯基、咪唑基、吡唑基、三嗪基、四嗪基、三唑基、四唑基、吡啶基、吡嗪基、嘧啶基、哒嗪基等,稠环型杂芳基包括苯并咪唑基、异吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、异喹啉基、噌啉基、喹唑啉基、喹喏啉基、咔唑基、啡啶基等。此外,“卤素”包括F、CL、Br和I。
在本文,表述“经取代或未经取代的”中的“经取代的”意指在某一官能团中的氢原子被另一个原子或基团(即取代基)替换。在式中的经取代的烷基、经取代的烯基、经取代的炔基、经取代的环烷基、经取代的(亚)芳基、经取代的(亚)杂芳基、经取代的三烷基硅烷基、经取代的三芳基硅烷基、经取代的二烷基芳基硅烷基、经取代的烷基二芳基硅烷基、经取代的单或二-芳氨基或经取代的单环或多环、(C3-C30)脂环族环或芳香族环的取代基各自独立地为选自由以下各者组成的群组中的至少一个:氘、卤基、氰基、羧基、硝基、羟基、(C1-C30)烷基、卤代(C1-C30)烷基、(C2-C30)烯基、(C2-C30)炔基、(C1-C30)烷氧基、(C1-C30)烷硫基、(C3-C30)环烷基、(C3-C30)环烯基、3到7元杂环烷基、(C6-C30)芳氧基、(C6-C30)芳基硫基、未经取代或经(C6-C30)芳基取代的3到30元杂芳基、未经取代或经氰基取代的(C6-C30)芳基、3到30元杂芳基或三(C6-C30)芳基硅烷基、三(C1-C30)烷基硅烷基、三(C6-C30)芳基硅烷基、二(C1-C30)烷基(C6-C30)芳基硅烷基、(C1-C30)烷基二(C6-C30)芳基硅烷基、氨基、单或二-(C1-C30)烷氨基、单或二(C6-C30)芳氨基、(C1-C30)烷基(C6-C30)芳氨基、(C1-C30)烷基羰基、(C1-C30)烷氧羰基、(C6-C30)芳基羰基、二(C6-C30)芳基硼基、二(C1-C30)烷基硼基、(C1-C30)烷基(C6-C30)芳基硼基、(C6-C30)芳基(C1-C30)烷基和(C1-C30)烷基(C6-C30)芳基,并且优选地为选自由以下各者组成的群组中的至少一个:卤素、氰基、(C1-C6)烷基、未经取代或经(C6-C12)芳基取代的5到15元杂芳基、未经取代或经氰基取代的(C6-C25)芳基、(C6-C12)芳基或三(C6-C12)芳基硅烷基、三(C6-C12)芳基硅烷基,以及(C1-C6)烷基(C6-C12)芳基。
由式1表示的化合物包括以下化合物,但不限于此:
由式2表示的化合物包括以下化合物,但不限于此:
由式1和式2表示的化合物可通过本领域技术人员已知的合成方法制备。举例来说,式1的化合物可根据以下反应流程制备。
[反应流程1]
其中R1到R2如以上式1中所定义。
具体来说,所述有机电致发光装置包含第一电极;第二电极;以及在所述第一与第二电极之间的至少一个有机层。所述有机层包含发光层,并且所述发光层包含一种或多种由式1表示的掺杂剂化合物与一种或多种由式2表示的主体化合物的组合。
第一电极和第二电极中的一个可为阳极,并且另一个可为阴极。有机层可进一步包含至少一个选自由空穴注入层、空穴传输层、电子传输层、电子注入层、夹层和空穴阻挡层组成的群组的层。
所述发光层是发射光的层,并且其可为单层,或其可为两层或更多层被层压的多层。发光层除发光以外还可注入/转移电子/空穴。以发光层的掺杂剂和主体的总量计,掺杂剂优选地以小于25wt%的量掺杂。
本发明的另一个实施例提供一种或多种由式1表示的掺杂剂化合物与一种或多种由式2表示的主体化合物的掺杂剂与主体组合,以及包含掺杂剂与主体组合的有机EL装置。
本发明的又一实施例提供包含一种或多种由式1表示的掺杂剂化合物与一种或多种由式2表示的主体化合物的组合的有机电致发光材料,以及包含该材料的有机EL装置。所述材料可单独包含由式1表示的化合物和由式2表示的化合物的组合,或可进一步包括通常用于有机电致发光材料的常规材料。
本发明的又一实施例提供含有一种或多种由式1表示的掺杂剂化合物与一种或多种由式2表示的主体化合物的组合的有机电致发光层。所述有机层包含多个层。所述掺杂剂化合物与主体化合物可包含于同一层中,或可包含于不同层中。另外,本发明提供包含该有机层的有机EL装置。
本发明的有机电致发光装置包含式1和式2的化合物,且可进一步包含至少一种选自由基于芳胺的化合物和基于苯乙烯基芳胺的化合物组成的群组的化合物。
另外,在根据本发明的有机电致发光装置中,有机层可进一步包含至少一种选自由以下各者组成的群组的金属:周期表的第1族金属、第2族金属、第4周期过渡金属、第5周期过渡金属、镧系元素和d-过渡元素的有机金属,或包含所述金属的至少一种络合化合物。此外,所述有机层可进一步包含发光层和电荷产生层。
另外,本发明的有机电致发光装置可通过进一步包含至少一个发光层而发射白光,该至少一个发光层包含在本领域中已知的蓝色电致发光化合物、红色电致发光化合物或绿色电致发光化合物。此外,必要时,装置中可包含发黄光或橙光层。
根据本发明,至少一层(下文中,“表面层”)优选地放置在一个或两个电极的(一个或多个)内表面上;选自硫族化物层、金属卤化物层和金属氧化物层。具体来说,硅或铝的硫族化物(包括氧化物)层优选地放置在电致发光介质层的阳极表面上,并且金属卤化物层或金属氧化物层优选地放置在电致发光介质层的阴极表面上。此类表面层为有机电致发光装置提供操作稳定性。优选地,所述硫族化物包括SiOX(1≤X≤2)、AlOX(1≤X≤1.5)、SiON、SiAlON等;所述金属卤化物包括LiF、MgF2、CaF2、稀土金属氟化物等;且所述金属氧化物包括Cs2O、Li2O、MgO、SrO、BaO、CaO等。
在根据本发明的有机电致发光装置中,电子传输化合物和还原性掺杂剂的混合区、或空穴传输化合物和氧化性掺杂剂的混合区优选地放置在一对电极的至少一个表面上。在这种情况下,电子传输化合物被还原为阴离子,并且因此注入电子并将其从混合区传输到电致发光介质中变得更加容易。此外,空穴传输化合物被氧化为阳离子,并且因此变注入电子并且将其从混合区传输空穴到电致发光介质得更容易。优选地,氧化性掺杂剂包括各种路易斯酸(Lewis acid)和受体化合物;并且还原性掺杂剂包括碱金属、碱金属化合物、碱土金属、稀土金属以及其混合物。还原性掺杂剂层可用作电荷产生层以制备具有两个或更多个电致发光层并且发射白光的电致发光装置。
为了形成本发明的有机电致发光装置的每一层,可使用干式成膜方法,如真空蒸发、溅镀、等离子体以及离子电镀方法;或湿式成膜方法,如喷墨印刷、喷嘴印刷、狭缝涂布、旋转涂布、浸渍涂布以及流动涂布方法。本发明的掺杂剂和主体化合物可经共-蒸发或混合物蒸发。
当使用湿法成膜方法时,可通过将形成每一层的材料溶解或扩散到任何合适的溶剂中来形成薄膜,所述溶剂如乙醇、氯仿、四氢呋喃、二噁烷等。所述溶剂可以是形成每一层的材料可溶解或扩散于其中并且不存在成膜能力问题的任何溶剂。
在本文中,共蒸发指示用于使两种或更多种材料以混合物形式沉积的方法,通过将该两种或更多种材料中的每一种引入到相应坩埚单元中,且向该单元施加电流用以蒸发材料中的每一种材料来进行。在本文中,混合物蒸发指示用于使两种或更多种材料以混合物形式沉积的方法,通过将该两种或更多种材料在一个坩埚单元中混合,随后沉积,且向该单元施加电流用以蒸发混合物来进行。
通过使用本发明的有机电致发光装置,可制造显示系统或照明系统。
在下文中,将参考以下实例详细说明包含本发明的掺杂剂化合物和主体化合物的装置的发光特性。
装置实例1:制备包含本发明的掺杂剂和主体的OLED装置
使用根据本发明的掺杂剂和主体化合物制造OLED装置。依次用三氯乙烯、丙酮、乙醇及蒸馏水对有机发光二极管(OLED)装置(Geomatec)的玻璃衬底上的透明电极氧化铟锡(ITO)薄膜(10Ω/sq)进行超声波洗涤,且然后储存于异丙醇中。然后将ITO衬底安装在真空气相沉积设备的衬底固持器上。将N4,N4'-二苯基-N4,N4'-双(9-苯基-9H-咔唑-3-基)-[1,1'-联苯]-4,4'-二胺(化合物HI-1)引入到所述真空气相沉积设备的单元中,并且然后将所述设备的腔室中的压力控制为10-6托。此后,向该单元施加电流以蒸发以上引入的材料,从而在ITO衬底上形成厚度为80nm的第一空穴注入层。接着,将1,4,5,8,9,12-六氮杂三亚苯六甲腈(化合物HI-2)引入到所述真空气相沉积设备的另一单元中,并且通过向该单元施加电流而蒸发,从而在第一空穴注入层上形成厚度为5nm的第二空穴注入层。然后,将N-([1,1'-联苯基]-4-基)-9,9-二甲基-N-(4-(9-苯基-9H-咔唑-3-基)苯基)-9H-芴-2-胺(化合物HT-1)引入到所述真空气相沉积设备的另一单元中,并且通过向单元施加电流而蒸发,从而在第二空穴注入层上形成厚度为10nm的第一空穴传输层。然后,然后将N-(4-(9,9-二苯基-9H,9'H-[2,9'-二茀-9'-基)苯基)-9,9-二甲基-N-苯基-9H-芴-2-胺(化合物HT-2)引入到所述真空气相沉积设备的另一个单元中,并且通过向所述单元施加电流而蒸发,从而在第一空穴传输层上形成厚度为60nm的第二空穴传输层。将在表1中列出的主体化合物引入到所述真空气相沉积设备的一个单元中作为主体,并且将掺杂剂化合物引入另一个单元中。主体材料蒸发,而掺杂剂以与主体材料不同的速率蒸发,使得掺杂剂以主体及掺杂剂的总量计以3wt%的掺杂量沉积,以在第二空穴传输层上形成厚度为40nm的发光层。然后,向真空气相沉积设备的两个单元中分别引入2,4-双(9,9-二甲基-9H-茀-2-基)-6-(萘-2-基)-1,3,5-三嗪(化合物ET-1)和喹啉锂(化合物EI-1),并且以1:1的速率蒸发以在发光层上形成厚度为30nm的电子传输层。在电子传输层上将喹啉锂(化合物EI-1)沉积为厚度为2nm的电子注入层之后,通过另一个真空气相沉积设备沉积厚度为80nm的Al阴极。因此,制造OLED装置。
比较实例1:制备包含本发明的主体化合物和常规掺杂剂化合物的OLED装置
以与在装置实例1中相同方式制造OLED装置,不同之处在于使用化合物RD-1作为发光层的掺杂剂。
在装置实例1和比较实例1中制造的OLED装置的评估结果在下表1中示出。
[表1]
当使用根据本发明的掺杂剂和主体化合物时,提供一种相较于常规装置具有较高发光效率和更长使用寿命的有机EL装置。
Claims (4)
1.一种或多种由下式1表示的掺杂剂化合物与一种或多种由下式2表示的主体化合物的一种组合:
其中
R1和R2各自独立地表示氢、氘、甲基、乙基、正丙基、异丙基、叔丁基或异丁基;且
a和b各自独立地表示1到4的整数;其中a或b为2或更大的整数,R1中的每个和R2中的每个可相同或不同,
其中
Ma表示选自由以下各者组成的群组的单环型杂芳基:经取代或未经取代的喹唑啉基以及经取代或未经取代的喹喏啉基,其中经取代的喹唑啉基以及经取代的喹喏啉基的取代基选自氘、或未经取代的(C6-C60)芳基;
La表示单键;
Xa,Xb,Xd到Xh各自独立地表示氢或氘;
Xc表示取代或未取代的咔唑基,其中取代的咔唑基的取代基选自氘、或未经取代的(C6-C60)芳基。
4.一种有机电致发光装置,所述有机电致发光装置包含根据权利要求1所述的组合。
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US20190157575A1 (en) * | 2017-11-17 | 2019-05-23 | Chuanjun Xia | Metal complex containing azabenzothiazole |
US20190194234A1 (en) * | 2017-12-25 | 2019-06-27 | Chuanjun Xia | Metal complexes containing heterocycle substituted ligands, and electroluminescent devices and formulations containing the complexes |
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