CN103180407B - 用于有机电致发光器件的基于苯并菲的材料 - Google Patents

用于有机电致发光器件的基于苯并菲的材料 Download PDF

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CN103180407B
CN103180407B CN201180049846.9A CN201180049846A CN103180407B CN 103180407 B CN103180407 B CN 103180407B CN 201180049846 A CN201180049846 A CN 201180049846A CN 103180407 B CN103180407 B CN 103180407B
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CN103180407A (zh
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菲利普·施特塞尔
多米尼克·约斯滕
阿尔内·比辛
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Merck Patent GmbH
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Abstract

本发明涉及式(1)和(2)的化合物,所述化合物适合用于电子器件中,特别是有机电致发光器件中。

Description

用于有机电致发光器件的基于苯并菲的材料
技术领域
本发明涉及用于电子器件中,特别是用于有机电致发光器件中的材料。
背景技术
在例如US4539507、US5151629、EP0676461和WO98/27136中,描述了其中将有机半导体用作功能材料的有机电致发光器件(OLED)的结构。在此处所使用的发光材料越来越多地为显示磷光而不是荧光的有机金属络合物(M.A.Baldo等人,Appl.Phys.Lett.1999,75,4-6)。由于量子力学原因,使用有机金属化合物作为磷光发光体可能实现最高达四倍的能量和功率效率。总的来说,在OLED的情况下,特别是还在显示三重态发光(磷光)的OLED的情况下,例如在效率、工作电压和寿命方面,仍然需要进行改进。对于在相对短波区域例如绿色区域发光的OLED而言,情况尤其如此。
磷光OLED的性质不仅取决于使用的三重态发光体。特别地,在此处,使用的其它材料例如基质材料、空穴阻挡材料、电子传输材料、空穴传输材料和电子或激子阻挡材料,也是特别重要的。因此,这些材料的改进也能够导致OLED性质的显著改进。在这些材料用于荧光OLED的情况下,也仍然需要改进。
根据现有技术,例如根据JP2005/071983或WO2006/038709,苯并菲衍生物用作磷光发光体的基质材料。然而,在使用这些基质材料时,特别是在器件的效率和寿命方面,还需要改进。
发明内容
本发明的目的是提供适合用于荧光或磷光OLED特别是磷光OLED中的化合物,该化合物例如用作基质材料和/或用作空穴传输/电子阻挡材料或激子阻挡材料和/或用作电子传输或空穴阻挡材料。特别地,本发明的目的是提供适合用于绿色和红色磷光OLED的基质材料。
令人惊讶地,已经发现,如下的苯并菲衍生物实现了该目的并且导致有机电致发光器件的改进,特别是在寿命、效率和工作电压方面的改进,所述苯并菲衍生物在1位和12位被芳族或杂芳族环系、羰基基团或氧化膦基团取代,或者在所述苯并菲衍生物中,1位和12位经由如下基团桥连,该基团选自在每种情况下任选取代的硼、碳、硅、锗、锡、氮、氧、硫或磷。这特别适用于红色和绿色磷光的电致发光器件,尤其是当本发明化合物用作基质材料时。本发明的材料能够以很少的步骤并且以高产率进行合成。因此,本发明涉及这些材料,并且涉及包含这种类型的化合物的有机电致发光器件。
为清楚起见,苯并菲的编号描述如下:
因此,本发明涉及下式(1)或式(2)的中性化合物,
其中以下适用于使用的符号和标记:
X在每次出现时相同或不同地优选相同地是BR2、C(R2)2、C=O、Si(R2)2、Ge(R2)2、Sn(R2)2、NR2、O、S、SO、SO2、PR2或P(=O)R2
或者,对于n=0,X是下式(3)的基团,
A是C、Si、Ge或Sn;此处A上的虚线键表示与苯并菲键合;
Y是BR2、O、S、NR2、PR2或P(=O)R2
Z在每次出现时相同或不同地是CR1或N,条件是每个环中最多两个基团Z代表N;
R在每次出现时相同或不同地选自N(Ar1)2,C(=O)Ar1,P(=O)(Ar1)2和具有5至60个芳族环原子的芳族或杂芳族环系,所述环系在每种情况下可以被一个或多个基团R1取代;
Ar1在每次出现时相同或不同地是具有5至60个芳族环原子的芳族或杂芳族环系,所述环系可以被一个或多个非芳族基团R3取代;在此处两个与同一N原子或P原子键合的基团Ar1还可以经由单键或选自N(R4),C(R4)2,O或S的桥连基彼此桥连;
R1在每次出现时相同或不同地选自H,D,F,Cl,Br,I,CN,NO2,N(Ar1)2,N(R3)2,C(=O)Ar1,C(=O)R3,P(=O)(Ar1)2,具有1至40个C原子的直链烷基、烷氧基或硫代烷基基团或者具有3至40个C原子的支链或环状的烷基、烷氧基或硫代烷基基团或者具有2至40个C原子的烯基或炔基基团,其中所述烷基、烷氧基、硫代烷基、烯基或炔基基团在每种情况下可以被一个或多个基团R3取代,并且其中一个或多个非相邻的CH2基团可以被R3C=CR3、C≡C、Si(R3)2、Ge(R3)2、Sn(R3)2、C=O、C=S、C=Se、C=NR3、P(=O)(R3)、SO、SO2、NR3、O、S或CONR3代替,并且其中一个或多个H原子可以被D、F、Cl、Br、I、CN或NO2代替,具有5至60个芳族环原子的芳族或杂芳族环系,所述环系在每种情况下可以被一个或多个基团R3取代,具有5至60个芳族环原子的芳氧基或杂芳氧基基团,所述基团可以被一个或多个基团R3取代,或这些体系的组合,其中两个或更多个与同一苯环键合的相邻取代基R1可以任选形成单环或多环的脂族、芳族或杂芳族环系;
R2在每次出现时相同或不同地选自具有1至20个C原子的直链烷基基团或者具有3至20个C原子的支链或环状的烷基基团,所述基团中的每个可以被一个或多个基团R3取代,其中一个或多个非相邻的CH2基团可以被R3C=CR3、C≡C、Si(R3)2、C=O、C=NR3、P(=O)(R3)、SO、SO2、NR3、O、S或CONR3代替,并且其中一个或多个H原子可以被D、F、Cl、Br、I、CN或NO2代替,或者具有5至60个芳族环原子的芳族或杂芳族环系,所述环系在每种情况下可以被一个或多个基团R3取代,其中两个与同一碳、硅、锗或锡原子键合的取代基R2可以任选彼此形成单环或多环的脂族、芳族或杂芳族环系,所述环系可以被一个或多个基团R3取代;
R3在每次出现时相同或不同地选自H,D,F,Cl,Br,I,CN,NO2,N(R4)2,C(=O)Ar1,C(=O)R4,P(=O)(Ar1)2,具有1至40个C原子的直链烷基、烷氧基或硫代烷基基团或者具有3至40个C原子的支链或环状的烷基、烷氧基或硫代烷基基团或者具有2至40个C原子的烯基或炔基基团,其中所述烷基、烷氧基、硫代烷基、烯基或炔基基团可以被一个或多个基团R4取代,并且其中一个或多个非相邻的CH2基团可以被R4C=CR4、C≡C、Si(R4)2、C=O、C=NR4、P(=O)(R4)、SO、SO2、NR4、O、S或CONR4代替,并且其中一个或多个H原子可以被D、F、Cl、Br、I、CN或NO2代替,具有5至60个芳族环原子的芳族或杂芳族环系,所述环系在每种情况下可以被一个或多个基团R4取代,具有5至60个芳族环原子的芳氧基或杂芳氧基基团,所述基团可以被一个或多个基团R4取代,或这些体系的组合,其中两个或更多个相邻的取代基R3可以任选形成单环或多环的脂族、芳族或杂芳族环系,所述环系可以被一个或多个基团R4取代;
R4选自H,D,F,CN,具有1至20个C原子的脂族烃基团,具有5至30个芳族环原子的芳族或杂芳族环系,其中一个或多个H原子可以被D、F、Cl、Br、I、CN或具有1至5个C原子的烷基基团代替,其中两个或更多个相邻的取代基R4可以彼此形成单环或多环的脂族、芳族或杂芳族环系;
n是0或1;
条件是,如果X代表C=O、O、S、SO或SO2并且n=0,则式(1)中至少一个基团R1代表芳族或杂芳族环系;
并且还有如下条件,即本发明不包括如下化合物:
在Ar1定义中所提及的“非芳族基团”R3是根据R3的定义的如下基团,该基团不含芳族或杂芳族基团,即,例如,也不含芳族羰基基团。
在本发明意义上的芳基基团包含6至60个C原子;在本发明意义上的杂芳基基团包含2至60个C原子和至少一个杂原子,条件是C原子和杂原子的总和至少为5。所述杂原子优选选自N、O和/或S。在此处芳基基团或杂芳基基团被认为是指简单的芳族环,即苯,或简单的杂芳族环,例如吡啶、嘧啶、噻吩等,或缩合(稠合)的芳基或杂芳基基团,例如萘、蒽、菲、喹啉、异喹啉等。与之相比,经由单键彼此连接的芳族基团,例如联苯或联吡啶,不被称为芳基或杂芳基基团,而是被称为芳族环系。
在本发明意义上的芳族环系在环系中包含6至60个C原子。在本发明意义上的杂芳族环系在环系中包含2至60个C原子和至少一个杂原子,条件是C原子和杂原子的总和至少为5。所述杂原子优选选自N、O和/或S。为了本发明的目的,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基团的体系,而是其中多个芳基或杂芳基基团还可以经由非芳族单元(优选小于非H原子的10%)连接,该非芳族单元例如为C、N、O或Si原子。因此,和其中两个或更多个芳基基团经由例如具有一至五个C原子的烷基基团或羰基基团连接的体系一样,例如,诸如芴、9,9'-螺二芴、9,9-二芳基芴、三芳基胺、二芳基醚、茋等的体系也旨在被认为是为了本发明目的的芳族环系。
为了本发明的目的,通常可以含有1至40个或也可以含有1至20个C原子并且其中单个H原子或CH2基团还可以被上述基团取代的脂族烃基团或烷基基团或烯基或炔基基团,优选被认为是指如下基团,即甲基、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、三氟甲基、五氟乙基、2,2,2-三氟乙基、乙烯基、丙烯基、丁烯基、戊烯基、环戊烯基、己烯基、环己烯基、庚烯基、环庚烯基、辛烯基、环辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基或辛炔基。具有1至40个C原子的烷氧基基团优选被认为是指甲氧基、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。具有1至40个C原子的硫代烷基基团特别是被认为是指甲硫基、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、正戊硫基、仲戊硫基、正己硫基、环己硫基、正庚硫基、环庚硫基、正辛硫基、环辛硫基、2-乙基己硫基、三氟甲硫基、五氟乙硫基、2,2,2-三氟乙硫基、乙烯硫基、丙烯硫基、丁烯硫基、戊烯硫基、环戊烯硫基、己烯硫基、环己烯硫基、庚烯硫基、环庚烯硫基、辛烯硫基、环辛烯硫基、乙炔硫基、丙炔硫基、丁炔硫基、戊炔硫基、己炔硫基、庚炔硫基或辛炔硫基。通常,根据本发明的烷基、烷氧基或硫代烷基基团可为直链、支链或环状的,其中一个或多个非相邻的CH2基团可以被上述基团代替;此外,一个或多个H原子还可以被D、F、Cl、Br、I、CN或NO2,优选被F、Cl或CN,进一步优选被F或CN,特别优选被CN所代替。
在每种情况下也可以被上述基团R2或烃基团取代并且可以经由芳族或杂芳族环系上任何希望的位置连接的具有5至60个芳族环原子的芳族或杂芳族环系,被认为特别是指来源于如下物质的基团或来源于这些体系的组合的基团: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、唑、苯并唑、萘并唑、蒽并唑、菲并唑、异唑、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、吩嗪、吩噻嗪、荧红环、萘啶、氮杂咔唑、苯并咔啉、菲咯啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-二唑、1,2,4-二唑、1,2,5-二唑、1,3,4-二唑、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、吲嗪和苯并噻二唑。
在本发明的优选实施方式中,每个环中最多一个基团Z代表N,而其它基团Z在每次出现时相同或不同地代表CR1。在本发明的特别优选的实施方式中,所有的基团Z在每次出现时相同或不同地代表CR1
因此,式(1)和(2)的化合物的优选实施方式是下式(4)至(7)的化合物,
其中使用的符号具有上文给出的含义。式(4)和(6)中的X不能是式(3)的基团。
式(4)至(7)的化合物的优选实施方式是下式(4a)至(7a)的化合物,
其中使用的符号具有上文给出的含义。
在其中n=0的式(1)的化合物中或者在式(4)或式(4a)的化合物中,X优选选自C(R2)2、Si(R2)2和N(R2),特别优选N(R2)。
R2优选在每次出现时相同或不同地代表具有5至40个芳族环原子,优选具有5至24个芳族环原子的芳族或杂芳族环系,其在每种情况下还可以被一个或多个基团R3取代,并且其中两个与同一碳、硅、锗或锡原子键合的基团R2还可以彼此形成芳族环系并且可以因此形成螺环系。在下文与R1的优选基团一起显示了特别优选的芳族或杂芳族环系R2
其中X代表式(3)基团的式(1)的化合物或者式(5)或式(5a)的化合物的优选实施方式中,所述两个与A键合的苯并菲部分在每种情况下被相同地取代。在这些化合物中,A还优选代表碳或硅,特别优选代表碳。
在其中n=1的式(1)的化合物中或者在式(6)或式(6a)的化合物中,基团X-Y-X优选选自C(R2)2-O-C(R2)2、Si(R2)2-O-Si(R2)2、O-BR2-O、O-PR2-O、O-P(=O)R2-O和C(=O)-NR2-C(=O)。
在式(2)或式(7)或式(7a)的化合物的优选实施方式中,相同地选择所述两个基团R。
在本发明的优选实施方式中,在上文所给出式中的R1在每次出现时相同或不同地选自H,D,F,Cl,Br,CN,N(Ar1)2,C(=O)Ar1,具有1至10个C原子的直链烷基或烷氧基基团或者具有3至10个C原子的支链或环状的烷基或烷氧基基团或者具有2至10个C原子的烯基或炔基基团,所述基团中的每个可以被一个或多个基团R3取代,其中一个或多个非相邻的CH2基团可以被O代替,并且其中一个或多个H原子可以被D或F代替,或者具有5至30个芳族环原子的芳族或杂芳族环系,该环系在每种情况下可以被一个或多个基团R3取代。
在本发明的特别优选的实施方式中,在上文所给出式中的R1在每次出现时相同或不同地选自H,D,F,CN,具有1至10个C原子的直链烷基基团或者具有3至10个C原子的支链或环状的烷基基团,所述基团中的每个可以被一个或多个基团R3取代,其中一个或多个H原子可以被D或F代替,或者具有5至18个芳族环原子的芳族或杂芳族环系,该环系在每种情况下可以被一个或多个基团R3取代。
在本发明的其它实施方式中,直接与苯并菲键合的基团R1等于H。
对于通过真空蒸镀进行处理的化合物,所述烷基基团优选具有不超过四个C原子,特别优选不超过1个C原子。对于从溶液处理的化合物,如下的化合物也是合适的,所述化合物被具有最多达10个C原子的烷基基团取代或者被低聚亚芳基基团例如邻位、间位、对位或支链的三联苯基团或四联苯基团取代。
根据本发明化合物的用途,选择不同的取代基R和R1
如果式(1)或(2)或(4)至(7)或(4a)至(7a)的化合物用作磷光发光体的基质材料,则至少一个基团R1优选代表N(Ar1)2、C(=O)Ar1、P(=O)(Ar1)2或者代表具有5至60个芳族环原子的芳族或杂芳族环系,该环系可以被一个或多个基团R3取代,其中所述基团Ar1或者在Ar1上的基团或者所述芳族或杂芳族环系或者在所述芳族或杂芳族环系上的基团R3不含具有超过10个C原子的稠合芳基基团,并且不含其中超过两个芳基或6元杂芳基基团直接稠合至彼此上的稠合杂芳基基团。
在本发明的特别优选的实施方式中,Ar1或者在Ar1上的基团或者所述芳族或杂芳族环系或者在所述芳族或杂芳族环系上的基团R3不含稠合芳基基团,并且不含其中两个或更多个芳基或6元杂芳基基团直接稠合至彼此上的稠合杂芳基基团。
特别优选的基团Ar1选自苯基,邻位、间位或对位的联苯,邻位、间位或对位的三联苯,邻位、间位、对位或支链的四联苯,芴或螺二芴,其中的每个可以被一个或多个非芳族基团R3取代但优选为未取代的。
特别优选的芳族环系R1和R2选自苯基,邻位、间位或对位的联苯,邻位、间位或对位的三联苯,邻位、间位、对位或支链的四联苯,芴或螺二芴,其中的每个可以被一个或多个基团R3取代但优选为未取代的。
特别优选的杂芳族环系R1和R2含有如下结构作为杂芳基基团,即三嗪、嘧啶、吡嗪、哒嗪、吡啶、苯并噻吩、苯并呋喃、吲哚、咔唑、氮杂咔唑、二氮杂咔唑、二苯并噻吩和/或二苯并呋喃。在此处所述杂芳族环系特别是选自下式(8)至(38)的结构,
其中R3具有上文所给出的含义,并且虚线键表示与所述苯并菲骨架或与X的键合。
式(8)至(38)的基团的优选实施方式是下式(8a)至(38a)的结构,
其中R3具有上文给出的含义,并且虚线键表示与所述苯并菲骨架或与X的键合。式(8a)中的R3优选相同或不同地代表具有5至24个芳族环原子的芳族或杂芳族环系,特别地,相同或不同地代表苯基、联苯、三联苯或四联苯。
如果R1或R代表基团N(Ar1)2,那么这种基团优选选自下式(39)或(41)的结构,并且,如果R1或R2或R代表是三芳基胺或三杂芳基胺基团的芳族或杂芳族环系,那么这种基团优选选自下式(40)的结构,
其中使用的符号具有上文所给出的含义,虚线键代表与所述苯并菲骨架的键合,或者在式(40)中还代表与X的键合,此外:
Ar2在每次出现时相同或不同地是具有5至24个芳族环原子的芳族或杂芳族环系,该环系可以被一个或多个基团R3取代;在此处,所有基团Ar2的芳族环原子在一起的总数不超过60;
E选自C(R4)2、NR4、O或S。
式(39)中的Ar1和式(40)中的Ar2优选在每次出现时相同或不同地代表苯基,1-萘基或2-萘基,邻位、间位或对位的联苯,邻位、间位、对位或支链的三联苯,邻位、间位、对位或支链的四联苯,2-芴基或2-螺二芴基,其中的每个可以被一个或多个基团R3取代。
如果式(2)或(7)或(7a)的化合物用作磷光发光体的基质材料,则R还优选在每次出现时相同或不同地代表N(Ar1)2、C(=O)Ar1、P(=O)(Ar1)2或者具有5至60个芳族环原子的芳族或杂芳族环系,所述环系可以被一个或多个基团R1取代,其中所述基团Ar1或者在Ar1上的基团或者所述芳族或杂芳族环系或者在所述芳族或杂芳族环系上的基团R1不含具有超过10个C原子的稠合芳基基团,并且不含其中超过两个芳基或6元杂芳基基团直接稠合至彼此上的稠合杂芳基基团。
在本发明的特别优选的实施方式中,Ar1或者在Ar1上的基团或者所述芳族或杂芳族环系或者在所述芳族或杂芳族环系上的基团R1不含稠合芳基基团,并且不含其中两个或更多个芳基或6元杂芳基基团直接稠合至彼此上的稠合杂芳基基团。
非常特别优选的基团Ar1选自苯基,邻位、间位或对位的联苯,邻位、间位或对位的三联苯,邻位、间位或对位或支链的四联苯,芴或螺二芴,其中的每个可以被一个或多个非芳族基团R3取代但优选为未取代的。
在式(2)中的非常特别优选的芳族或杂芳族环系R选自苯基,邻位、间位或对位的联苯,邻位、间位或对位的三联苯,邻位、间位、对位或支链的四联苯,芴,螺二芴,三嗪,吡啶,吡嗪,嘧啶,哒嗪或咔唑,其中的每个可以被一个或多个基团R1取代但优选为未取代的。
如果式(1)或(2)或(4)至(7)或(4a)至(7a)的化合物用作荧光发光体的基质材料,则在式(2)、(7)或(7a)中的至少一个基团R1和/或至少一个与X键合的基团R2和/或至少一个基团R优选代表含有至少一个如下芳基基团的芳族或杂芳族环系,该芳基基团具有至少三个稠合的六元环,优选蒽。在此处X优选代表N(R2)或代表C(R2)2
如果式(1)或(2)或(4)至(7)或(4a)至(7a)的化合物用作荧光发光体,则X优选代表N(R2),并且R2代表含有至少一个芳基基团的芳族或杂芳族环系或者具有至少两个稠合六元环的芳族环系,其优选与基团X的氮直接键合。在此处所述稠合芳基基团优选选自蒽、芘、菲、单苯并茚并芴或二苯并茚并芴。
如果式(1)或(2)或(4)至(7)或(4a)至(7a)的化合物用作电子传输材料,则在式(2)、(7)或(7a)中的至少一个基团R1和/或至少一个基团R优选代表C(=O)Ar1、P(=O)(Ar1)2或者代表具有5至40个芳族环原子、优选具有5至25个芳族环原子的缺电子杂芳族环系,其可以被一个或多个基团R3取代;和/或在其中n=0的式(1)化合物中的X优选代表BR2、C=O、SO、SO2或P(=O)(R2)2。在本发明意义上的缺电子杂芳族环系是含有至少一个缺电子杂芳基基团的杂芳族环系,该杂芳基基团是具有至少一个氮原子的6元杂芳基基团或具有至少两个杂原子的5元杂芳基基团。
特别优选的缺电子杂芳族环系R1含有至少一个如下的基团作为杂芳基基团,该基团选自三嗪、嘧啶、吡嗪、哒嗪、吡啶、咪唑、吡唑、唑、二唑、三唑、噻唑、噻二唑、苯并咪唑、喹啉、异喹啉和喹喔啉。在此处所述杂芳族环系特别是选自上文给出的式(8)至(11)和(8a)至(11a)的或选自下式(42)至(45)的结构,
其中R3具有上文给出的含义,并且虚线键表示与所述苯并菲骨架的键合。
式(42)至(45)的基团的优选实施方式是下式(42a)至(45a)的结构,
其中R3具有上文给出的含义,并且虚线键表示与所述苯并菲骨架的键合。在此处R3优选相同或不同地代表具有5至24个芳族环原子的芳族或杂芳族环系,特别地,相同或不同地代表苯基、联苯、三联苯或四联苯。
如果式(1)或(2)或(4)至(7)或(4a)至(7a)的化合物用作空穴传输材料或用作发光化合物,则至少一个基团R1和/或R优选代表N(Ar1)2,代表三芳基氨基基团,或者代表具有5至40个芳族环原子特别是5至25个芳族环原子的富电子杂芳族环系,该环系可以被一个或多个基团R3取代,特别是代表上文所给出式(39)至(41)之一的基团;和/或其中n=0的式(1)化合物中的X代表NR2或PR2。在本发明意义上的富电子杂芳族环系是含有至少一个富电子杂芳基基团的杂芳族环系,该杂芳基基团是具有确切地一个杂原子的5元杂芳基基团,其上还可以稠合一个或多个芳基基团。
特别优选的富电子杂芳族环系R1含有如下结构作为杂芳基基团,即吡咯、呋喃、噻吩、苯并噻吩、苯并呋喃、吲哚、咔唑、二苯并噻吩、二苯并呋喃和/或氮杂咔唑。在此处,所述富电子杂芳族环系特别地选自上文给出的式(12)至(38)的结构。
在本发明的实施方式中,上文给出的优选特征能够根据需要彼此组合。
上述实施方式的优选化合物或能够优选用于电子器件中的化合物的实例是如下结构(1)至(91)的化合物。
本发明化合物能够通过本领域普通技术人员已知的合成步骤来进行制备,如方案1至3中所示意性描绘的。
合适的合成方法是二(四甲基乙二胺)合1,12-二锂苯并菲(1,12-Dilithio-triphenylen×2TMEDA)(Chanda等人,Organometallics2007,26(7),1635-1642)与亲电子试剂反应以产生本发明式1至3的化合物,如方案1中所描绘的。
方案1:
此外,通过本领域普通技术人员熟悉的有机化学方法,例如通过Suzuki、Stille、Heck、Sonogashira、Yamamoto、Negishi、Ullmann或Buchwald偶联,如方案2中通过举例所显示的,能够将相应取代的苯并菲衍生物转化成芳族或杂芳族的烃、胺、醚、硫醚等。在此处<Pd>代表钯催化剂。
方案2:
C-C偶联,例如Suzuki偶联:
此外,如方案3中通过举例所显示的,能够在另外多个步骤中将相应取代的苯并菲衍生物(Saito等人,J.Organomet.Chem.2010,695(7),1035-1041)官能化。
因此,本发明还涉及用于制备式(1)或(2)的化合物的方法,该方法通过1,12-二锂苯并菲衍生物与亲电子试剂的反应或者通过在金属催化偶联反应中卤素或氨基取代的苯并菲衍生物的反应进行制备。
上述本发明化合物,特别是被反应性离去基团例如溴、碘、氯、硼酸或硼酸酯或者被反应性可聚合基团例如烯烃或氧杂环丁烷取代的化合物,能够用作用于生成相应低聚物、树枝状大分子或聚合物的单体。在此处优选经由卤素官能团或硼酸官能团或者经由可聚合基团进行低聚和聚合。还可以经由这种类型的基团进行聚合物的交联。本发明的化合物或聚合物能够用作交联的或未交联的层。
因此,本发明还涉及含有上文所指出本发明化合物中的一种或多种的低聚物、聚合物或树枝状大分子,其中存在一个或多个从本发明化合物至所述聚合物、低聚物或树枝状大分子的键。取决于本发明化合物的连接,这因此形成低聚物或聚合物的侧链或连接在主链中。所述聚合物、低聚物或树枝状大分子可以是共轭的、部分共轭的或非共轭的。所述低聚物或聚合物可以是直链的、支链的或树枝状的。如上文所述的相同的优选特征适用于本发明化合物在低聚物、树枝状大分子和聚合物中的重复单元。
为了制备所述低聚物或聚合物,可将本发明单体均聚或与其它单体共聚。优选如下的均聚或共聚,其中式(1)或(2)的单元或者上文指出的优选实施方式以0.01至99.9mol%、优选5至90mol%、特别优选20至80mol%的范围存在。合适并且优选的形成聚合物骨架的共聚单体选自芴(例如根据EP842208或WO2000/22026的),螺二芴(例如根据EP707020、EP894107或WO2006/061181的),对苯撑(例如根据WO92/18552的),咔唑(例如根据WO2004/070772或WO2004/113468的),噻吩(例如根据EP1028136的),二氢菲(例如根据WO2005/014689的),顺式-和反式-茚并芴(例如根据WO2004/041901或WO2004/113412的),酮(例如根据WO2005/040302的),菲(例如根据WO2005/104264或WO2007/017066的),或还有多个这些单元。所述聚合物、低聚物和树枝状大分子还可以包含其它单元,例如空穴传输单元,特别是基于三芳基胺的那些空穴传输单元,和/或电子传输单元。此外,所述聚合物可以含有共聚的或在掺合物中混合的磷光发光体。特别地,式(1)或(2)的单元或者上文指出的优选实施方式与磷光发光体的组合导致特别好的结果。
此外,式(1)或(2)的化合物或者上文指出的优选实施方式还可以进一步官能化并因此转化成扩展的结构。在此处作为实例可以提及的是通过Suzuki法与芳基硼酸的反应或通过Hartwig-Buchwald法与伯胺或仲胺的反应。因此,式(1)或(2)的化合物或者在此处提及的优选实施方式还可以与磷光金属络合物或以及其它金属络合物直接键合。
本发明化合物适合用于电子器件中。在此处电子器件被认为是指包括至少一个包含至少一种有机化合物的层的器件。然而,在此处所述组件还可以包含无机材料或者还可以包括完全由无机材料构成的层。
因此,本发明还涉及本发明上述化合物在电子器件中、特别是在有机电致发光器件中的用途。
此外,本发明还涉及包含本发明上述化合物中的至少一种的电子器件。上文所述的优选特征同样适用于该电子器件。
所述电子器件优选选自有机电致发光器件(OLED)、有机集成电路(O-IC)、有机场效应晶体管(O-FET)、有机薄膜晶体管(O-TFT)、有机发光晶体管(O-LET)、有机太阳能电池(O-SC)、有机光学检测器、有机光感受器、有机场猝熄器件(O-FQD)、发光电化学电池(LEC)、有机激光二极管(O-laser)和“有机等离子体发射器件”(D.M.Koller等人,NaturePhotonics2008,1-4),但是优选有机电致发光器件(OLED),特别优选磷光OLED。
所述有机电致发光器件包括阴极、阳极和至少一个发光层。除了这些层之外,它还可以包括其它层,例如在每种情况下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。同样可以在两个发光层之间引入具有例如激子阻挡功能的间层。然而,应该指出,这些层的每一个不必都存在。在此处所述有机电致发光器件可以包括一个发光层或多个发光层。如果存在多个发光层,则优选这些发光层总共具有多个在380nm和750nm之间的发光峰值,总体上导致白色发光,即,将多种能够发荧光或发磷光的发光化合物用于该发光层中。特别优选具有三个发光层的体系,其中所述三个层显示蓝色、绿色和橙色或红色发光(对于基本结构,例如见WO2005/011013)。
取决于确切的结构,根据上述实施方式的本发明化合物能够用于多个层中。优选如下的有机电致发光器件,其根据确切的取代,包含式(1)或(2)的化合物或者上文指出的优选实施方式用作荧光或磷光发光体特别是磷光发光体的基质材料,和/或用作荧光发光体和/或用于空穴阻挡层中和/或用于电子传输层中和/或用于电子阻挡或激子阻挡层中和/或用于空穴传输或空穴注入层中。上文指出的优选实施方式也适用于所述材料在有机电子器件中的用途。
在本发明的其它实施方式中,所述有机电致发光器件在光耦合输出层中包含式(1)或(2)的化合物或者上文指出的优选实施方式。在此处,光耦合输出层被认为是指为了改进光耦合输出的如下的层,该层不是位于阳极和阴极之间,而是被施加至实际器件外部的电极,例如位于电极和基底之间。
在本发明的优选实施方式中,式(1)或(2)的化合物或者上文指出的优选实施方式在发光层中用作荧光或磷光化合物特别是磷光化合物的基质材料。在此处所述有机电致发光器件可以包括一个发光层或多个发光层,其中至少一个发光层包含至少一种本发明化合物作为基质材料。
如果式(1)或(2)的化合物或者上文指出的优选实施方式在发光层中用作发光化合物的基质材料,则它优选与一种或多种磷光材料(三重态发光体)组合使用。在本发明意义上的磷光被认为是指来自相对高自旋多重度即自旋态>1的激发态,尤其来自激发三重态的发光。为了本申请的目的,所有的含有过渡金属或镧系元素的发光络合物,特别是所有的铱、铂和铜络合物,都将被视为磷光化合物。
式(1)或(2)的化合物或者上文指出的优选实施方式和发光化合物的混合物,基于包含发光体和基质材料的全部混合物,包含99至1vol%,优选98至10vol%,特别优选97至60vol%,特别是95至80vol%的式(1)或(2)的化合物或者上文指出的优选实施方式。相应地,基于包含发光体和基质材料的全部混合物,所述混合物包含1至99vol%,优选2至90vol%,特别优选3至40vol%,特别是5至20vol%的发光体。
本发明的另外的优选实施方式是,式(1)或(2)的化合物或者上文指出的优选实施方式与其它基质材料组合用作磷光发光体的基质材料。能够与式(1)或(2)的化合物或者上文指出的优选实施方式组合使用的特别合适的基质材料是芳族酮,芳族氧化膦或者芳族亚砜或砜,例如根据WO2004/013080、WO2004/093207、WO2006/005627或WO2010/006680的,三芳基胺,咔唑衍生物,例如CBP(N,N-二咔唑基联苯)或在WO2005/039246、US2005/0069729、JP2004/288381、EP1205527或WO2008/086851中公开的咔唑衍生物,吲哚并咔唑衍生物,例如根据WO2007/063754或WO2008/056746的,茚并咔唑衍生物,例如根据WO2010/136109或WO2011/000455的,氮杂咔唑衍生物,例如根据EP1617710、EP1617711、EP1731584、JP2005/347160的,双极性基质材料,例如根据WO2007/137725的,硅烷,例如根据WO2005/111172的,氮杂硼杂环戊二烯或硼酸酯,例如根据WO2006/117052的,三嗪衍生物,例如根据WO2007/063754、WO2008/056746、WO2010/015306、WO2011/057706、WO2011/060859或WO2011/060877的,锌络合物,例如根据EP652273或WO2009/062578的,二氮杂硅杂环戊二烯或四氮杂硅杂环戊二烯衍生物,例如根据WO2010/054729的,二氮杂磷杂环戊二烯衍生物,例如根据WO2010/054730的,桥连的咔唑衍生物,例如根据未公开申请WO2011/042107或WO2011/060867的。比现行发光体在较短波长处发光的其它磷光发光体同样可以在该混合物中作为共主体存在。
适合作为磷光化合物(=三重态发光体)的特别是如下的化合物,该化合物经适当激发时发光,优选在可见区发光,并且还含有至少一种原子序数大于20,优选大于38但小于84,特别优选大于56但小于80的原子,特别是具有这种原子序数的金属。使用的磷光发光体优选是含有铜、钼、钨、铼、钌、锇、铑、铱、钯、铂、银、金或铕的化合物,特别是含有铱或铂的化合物。
申请WO00/70655、WO01/41512、WO02/02714、WO02/15645、EP1191613、EP1191612、EP1191614、WO05/033244、WO05/019373和US2005/0258742公开了上述发光体的实例。通常,根据现有技术用于磷光OLED的和在有机电致发光领域普通技术人员所已知的所有磷光络合物都是合适的,并且本领域普通技术人员将能够在不需要付出创造性劳动的情况下使用其它磷光络合物。
在下表中示出了合适磷光化合物的实例。
在本发明的另外的实施方式中,所述有机电致发光器件不包括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,所述发光层与所述空穴注入层或所述阳极直接邻接,和/或所述发光层与所述电子传输层或所述电子注入层或所述阴极直接邻接,如在例如WO2005/053051中所述的。此外,可以使用与所述发光层中的金属络合物相同或相似的金属络合物作为与所述发光层直接邻接的空穴传输或空穴注入材料,如在例如WO2009/030981中所述的。
在本发明的另外优选的实施方式中,式(1)或(2)的化合物或者上文指出的优选实施方式将用作发光层中荧光发光体的基质材料。
合适的荧光掺杂剂例如选自单苯乙烯基胺、二苯乙烯基胺、三苯乙烯基胺、四苯乙烯基胺、苯乙烯基膦、苯乙烯基醚和芳基胺。单苯乙烯基胺被认为是指包含一个取代或未取代的苯乙烯基基团和至少一个胺优选芳族胺的化合物。二苯乙烯基胺被认为是指包含两个取代或未取代的苯乙烯基基团和至少一个胺优选芳族胺的化合物。三苯乙烯基胺被认为是指包含三个取代或未取代的苯乙烯基基团和至少一个胺优选芳族胺的化合物。四苯乙烯基胺被认为是指包含四个取代或未取代的苯乙烯基基团和至少一个胺优选芳族胺的化合物。所述苯乙烯基基团特别优选是茋,其也可以被进一步取代。以类似于胺的方式,定义相应的膦和醚。在本发明意义上的芳基胺或芳族胺被认为是指包含三个直接键合到氮上的取代或未取代的芳族或杂芳族环系的化合物。这些芳族或杂芳族环系中的至少一个优选是稠合环系,特别优选具有至少14个芳环原子的稠合环系。其优选的实例是芳族蒽胺、芳族芘胺、芳族芘二胺、芳族胺或芳族二胺。芳族蒽胺被认为是指其中二芳基氨基基团直接与蒽基团优选在9-位或在2-位键合的化合物。以与芳族蒽胺类似的方式定义芳族芘胺、芘二胺、胺和二胺,其中在芘上的二芳基氨基基团优选在1-位或在1,6-位键合。另外优选的掺杂剂选自茚并芴胺或茚并芴二胺,例如根据WO2006/108497或WO2006/122630的,苯并茚并芴胺或苯并茚并芴二胺,例如根据WO2008/006449的,和二苯并茚并芴胺或二苯并茚并芴二胺,例如根据WO2007/140847的。来自苯乙烯基胺类的掺杂剂的实例是取代或未取代的三茋胺,或描述于WO2006/000388、WO2006/058737、WO2006/000389、WO2007/065549和WO2007/115610中的掺杂剂。此外,合适的荧光掺杂剂是公开在WO2010/012328中的稠合烃。
在本发明的另外优选的实施方式中,式(1)或(2)的化合物或者上文指出的优选实施方式将用作发光层中的荧光发光体。
用于所述荧光掺杂剂,特别是用于上述掺杂剂的合适的主体材料(基质材料),例如选自以下的类别:低聚亚芳基(例如根据EP676461的2,2',7,7'-四苯基螺二芴,或二萘基蒽),特别是含有稠合芳族基团的低聚亚芳基,特别是蒽,低聚亚芳基亚乙烯基(例如根据EP676461的DPVBi或螺-DPVBi),多足金属络合物(例如根据WO2004/081017的),空穴传导化合物(例如根据WO2004/058911的),电子传导化合物,特别是酮、氧化膦、亚砜等(例如根据WO2005/084081和WO2005/084082的),阻转异构体(例如根据WO2006/048268的),硼酸衍生物(例如根据WO2006/117052的),苯并蒽衍生物(例如根据WO2008/145239或WO2011/012212的苯并[a]蒽衍生物)和苯并菲衍生物(例如根据WO2010/083869的苯并[c]菲衍生物)。特别优选的主体材料选自低聚亚芳基类,其含有萘,蒽,苯并蒽,特别是苯并[a]蒽,苯并菲,特别是苯并[c]菲,和/或芘,或这些化合物的阻转异构体。用于所述荧光发光体的非常特别优选的基质材料是蒽衍生物。在本发明意义上的低聚亚芳基旨在被认为是指其中至少三个芳基或亚芳基基团彼此键合的化合物。
在本发明的另外优选的实施方式中,式(1)或(2)的化合物或者上文指出的优选实施方式在电子传输或电子注入层中用作电子传输材料。在此处发光层可以是发荧光的或发磷光的。如果所述化合物用作电子传输材料,则可以优选它为掺杂的,例如掺杂有碱金属络合物,例如LiQ(羟基喹啉锂)。
在本发明又一另外优选的实施方式中,式(1)或(2)的化合物或者上文指出的优选实施方式用于特别是磷光OLED中的空穴阻挡层中。空穴阻挡层被认为是指与阴极侧的发光层直接邻接的层。
此外,式(1)或(2)的化合物或者上文指出的优选实施方式可以既在空穴阻挡层或电子传输层中使用,又在发光层中用作基质。
在本发明又一另外的实施方式中,式(1)或(2)的化合物或者上文指出的优选实施方式用于空穴传输层中或电子阻挡层中或激子阻挡层中。
在本发明有机电致发光器件的其它层中,可以使用根据现有技术通常使用的所有材料。因此,在不付出创造性劳动的情况下,本领域普通技术人员将能够与式(1)或(2)的本发明化合物或者上文指出的优选实施方式组合使用用于有机电致发光器件的所有已知材料。
此外,优选如下的有机电致发光器件,其特征在于,借助于升华方法涂覆一个或多个层,其中在真空升华装置中在低于10-5毫巴、优选低于10-6毫巴的初压下气相沉积所述材料。然而,该初压还可以甚至更低,例如低于10-7毫巴。
同样优选如下的有机电致发光器件,其特征在于,借助于OVPD(有机气相沉积)方法或借助于载气升华来涂覆一个或多个层,其中在10-5毫巴至1巴之间的压力下施加所述材料。该方法的一个特例是OVJP(有机蒸气喷印)方法,其中所述材料经由喷嘴直接施加并且因此是结构化的(例如,M.S.Arnold等人,Appl.Phys.Lett.2008,92,053301)。
此外,优选如下的有机电致发光器件,其特征在于,从溶液例如通过旋涂,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、LITI(光引发热成像、热转印)、喷墨印刷或喷嘴印刷,来制造一个或多个层。通过例如适当取代而获得的可溶性化合物对于此目的是必要的。这些方法也特别适合于低聚物、树枝状大分子和聚合物。
混合方法也是合适的,其中,例如,从溶液施加一个或多个层并且通过气相沉积施加一个或多个其它层。因此,例如,可从溶液施加发光层,而通过真空气相沉积将电子传输层施加至该层上。
这些方法通常为本领域普通技术人员所知,并且可由他在没有付出创造性劳动的情况下应用到包含本发明化合物的有机电致发光器件中。
为了从溶液中进行处理,需要本发明化合物的制剂,特别是溶液、悬浮液或微乳液。因此,本发明还涉及如下的制剂,特别是溶液、悬浮液或微乳液,其包含至少一种根据本发明的化合物和至少一种溶剂,特别是有机溶剂。
根据本发明的化合物和根据本发明的有机电致发光器件具有如下优于现有技术的令人惊讶的优点:
1.用作荧光或磷光发光体的基质材料的本发明的化合物或者式(1)或(2)的化合物或者上文指出的优选实施方式,导致非常高的效率和长寿命。特别是当所述化合物用作磷光发光体的基质材料时,情况如此。
2.本发明的化合物或者式(1)或(2)的化合物或者上文指出的优选实施方式,不仅适合用作红色磷光化合物的基质,而且还特别适合用作绿色磷光化合物的基质。
3.能够以简单方式以很少的反应步骤并且以高产率合成得到本发明的化合物。
4.用于有机电致发光器件中的本发明化合物,导致高效率,并且在低使用电压的情况下导致陡峭的电流/电压曲线。
5.还有,当用作电子传输材料或用作空穴传输材料时,本发明化合物导致在有机电致发光器件的效率、寿命和工作电压方面的非常好的性质。
上述这些优点并不伴有对其它电子性质的损害。
具体实施方式
通过如下实施例更详细地解释本发明,但并不希望由此限制本发明。在该说明书的基础上,本领域普通技术人员将能够在没有付出创造性劳动的情况下在所公开整个范围内实施本发明并且制备根据本发明的其它化合物,并且将它们用于电子器件中或使用根据本发明的方法。
实施例:
A)合成实施例:
除非另外指明,以下合成在干燥溶剂中在保护性气体气氛下进行。另外在避光条件下处理金属络合物。溶剂和试剂可从例如Sigma-ALDRICH或ABCR购得。在每种情况下在方括号中显示原料的CAS号。
实施例1:4-(2,4,6-三甲基苯基)-4H-4-环戊硼烷并[def]苯并菲
A:二(四甲基乙二胺)合1,12-二锂苯并菲
将58.1g(500mmol)N,N-四甲基乙二胺逐滴添加至312.5ml(500mmol)正丁基锂(1.6M,在正己烷中),并且将该混合物在室温下搅拌1小时。将22.8g(100mmol)苯并菲在150ml正己烷中的溶液逐滴添加至所述混合物,随后将其在回流下加热5小时。在已经蒸馏出约250ml正己烷后,使该反应混合物冷却,然后在-30℃下冷却24小时,在该冷却期间沉积出棕色固体。将该棕色固体用抽吸滤出,每次用100ml冰冷的正己烷洗涤三次,并且在真空下干燥。产率:134.7g(285mmol),57%。注意:二(四甲基乙二胺)合1,12-二锂苯并菲是自燃的。
B:4-(2,4,6-三甲基苯基)-4H-4-环戊硼烷并[def]苯并菲
将20.1g(100mmol)二氯-2,4,6-三甲基苯基硼烷[69464-76-2]在500ml THF中的溶液逐滴添加至47.2g(100mmol)二(四甲基乙二胺)合1,12-二锂苯并菲在1500ml THF中的溶液,并且将该混合物在室温下搅拌16小时。在真空下除去溶剂之后,将残余物溶于500ml二氯甲烷中,并且每次用200ml水洗涤三次。在经由硫酸钠干燥后,蒸发有机相,将残余物从二烷中重结晶五次,随后将其在真空中分级升华两次(p约10-6毫巴,T约300℃)。产率:13.2g(37mmol),37%。纯度:HPLC纯度99.9%。
相似地,通过二(四甲基乙二胺)合1,12-二锂苯并菲与相应亲电子试剂的反应,获得如下化合物:
实施例8:1,10-双-(N-苯基咔唑-2-基)-4H-4-硫杂环戊烷并[def]苯并菲
A)苯并菲并[1,12-bcd]噻吩-2,11-二硼酸
将48.8g(420mmol)N,N-四甲基乙二胺添加至25.8g(100mmol)苯并菲并[1,12-bcd]噻吩[68558-73-6]在2000ml正己烷的悬浮液中,然后逐滴添加250ml(400mmol)正丁基锂(1.6M,在正己烷中),随后将该混合物在60℃下搅拌4小时。在使该混合物冷却并且将其冷却至-60℃之后,在剧烈搅拌下以一份的方式添加46.8g(450mmol)硼酸三甲酯。将该混合物在-60℃下搅拌另外的30分钟,然后使其温热至室温,在真空下除去正己烷,将残余物溶于300ml的THF中,添加300ml水和30ml冰醋酸的混合物,将该混合物搅拌另外的2小时,将沉淀固体用抽吸过滤出,每次用200ml水洗涤两次,并在真空下干燥。产率:30.7g。纯度:根据NMR,约90.0%,粗产物在没有另外提纯的情况下用于随后的反应中。
B)1,10-双-(N-苯基咔唑-2-基)-4H-4-硫杂环戊烷并[def]苯并菲
将913mg(3mmol)三邻甲苯基膦并且然后将112mg(0.5mmol)乙酸钯(II)在搅拌下添加至17.3g(50mmol)苯并菲并[1,12-bcd]噻吩-2,11-二硼酸、41.9g(130mmol)2-溴-9-苯基咔唑[94994-62-4]和31.8g(150mmol)磷酸三钾在200ml甲苯、100ml乙醇和300ml水的混合物中的混合物,并且将该混合物在回流下加热16小时。冷却后,将沉淀的固体用抽吸过滤出,每次用100ml的水和乙醇(1:1,v:v)的混合物洗涤三次,然后每次用100ml乙醇洗涤三次,并在真空下干燥。将该固体用甲苯经由氧化铝(碱性,活性等级1)热蒸气提取五次,然后在真空下分级升华两次(p约10-6毫巴,T约350℃)。产率12.6g(34mmol),34%。纯度:HPLC纯度99.9%。
相似地,通过苯并菲并[1,12-bcd]噻吩-2,11-二硼酸与相应溴化物的反应,获得如下化合物:
实施例11:4-联苯-4-基-4H-4-氮杂环戊烷并[def]苯并菲
将235mg(1.3mmol)二叔丁基氯代膦并且然后将225g(1mmol)乙酸钯(II)添加至剧烈搅拌的12.1g(50mmol)4H-4-氮杂环戊烷并[def]苯并菲[109606-75-9]、14.0g(60mmol)4-溴联苯和9.0g(65mmol)碳酸钾在150ml甲苯的悬浮液中,并且将该混合物在回流下加热16小时。在冷却至60℃后,添加水,将该混合物搅拌另外的30分钟,然后将沉淀的固体用抽吸过滤出,每次用100ml的水和乙醇(1:1,v:v)的混合物洗涤三次,然后每次用100ml乙醇洗涤三次,并在真空下干燥。将该固体用甲苯经由氧化铝(碱性,活性等级1)热蒸气提取五次,然后在真空下分级升华两次(p约10-6毫巴,T约320℃)。产率7.3g(19mmol),37%。纯度:HPLC纯度99.9%。
相似地,通过4H-4-氮杂环戊烷并[def]苯并菲与相应溴化物反应,,获得如下化合物:
实施例14:1,12-(二苯并噻吩-2-基)苯并菲
将304mg(1mmol)三邻甲苯基膦并且然后将45mg(0.2mmol)乙酸钯(II)在搅拌下添加至9.6g(20mmol)1,12-二碘代苯并菲[130197-34-1]、11.4g(50mmol)2-二苯并噻吩硼酸[108847-24-1]和10.6g(50mmol)磷酸三钾在200ml甲苯、50ml二烷和200ml水的混合物中的混合物,并且将该混合物在回流下加热30小时。冷却之后,将沉淀的固体用抽吸过滤出,每次用50ml的水和乙醇(1:1,v:v)的混合物洗涤三次,然后每次用50ml乙醇洗涤三次,并在真空下干燥。将该固体用甲苯经由氧化铝(碱性,活性等级1)热蒸气提取四次,然后在真空下分级升华两次(p约10-6毫巴,T约310℃)。产率5.0g(8.4mmol),42%。纯度:HPLC纯度99.9%。
相似地,通过与相应硼酸的反应,获得如下的化合物:
实施例15:4,4-双[1,1',3',1'']三联苯-5'-基-4H-环戊烷并[def]苯并菲
将48.7g(100mmol)双[1,1',3',1'']三联苯-5'-基甲酮[1205748-29-3]在500mlTHF中的溶液逐滴添加至47.2g(100mmol)二(四甲基乙二胺)合1,12-二锂苯并菲在1500mlTHF中的溶液,然后将该混合物在回流下加热2小时。在使用50ml乙醇淬灭该反应混合物并在真空下除去溶剂后,将残余物溶于500ml冰醋酸中,将20ml浓盐酸和20ml乙酸酐添加至该悬浮液,并且将该混合物在回流下加热3小时。冷却之后,将沉淀的固体用抽吸过滤出,每次用100ml乙醇洗涤三次,并在真空下干燥。将该固体从DMF中重结晶五次,随后在真空下分级升华两次(p约10-6毫巴,T约350℃)。产率:38.3g(55mmol),55%。纯度:HPLC纯度99.9%。
实施例49:4,8,9,10-五苯基-4H-4-氮杂环戊烷并[def]苯并菲
A:8,9-二碘代-1,2,3,4-四苯基苯并菲
将7.6ml(50mmol)N,N-四甲基乙二胺逐滴添加至31.3ml(50mmol)正丁基锂(1.6M,在正己烷中),并且将该混合物在室温下搅拌1小时。将10.6g(20mmol)1,2,3,4-四苯基苯并菲[36262-81-4]在50ml正己烷中的溶液逐滴添加至所述混合物,随后将其在回流下加热5小时。在已蒸馏出约75ml正己烷之后,使该反应混合物冷却,并将其冷却至-100℃,添加50ml的THF,然后缓慢地逐滴添加7.0g(55mmol)碘在50ml THF中的溶液。当完成添加后,使该混合物缓慢温热至室温。将该反应混合物用200ml乙酸乙酯稀释,然后用100ml饱和亚硫酸钠溶液洗涤一次,每次用100ml水洗涤两次,并用100ml饱和氯化钠溶液洗涤一次。经由硫酸镁干燥并在真空下除去溶剂后,将该混合物用庚烷/乙酸乙酯(4:1,v/v)经由硅胶色谱分离。产率7.1g(9mmol),45%。纯度:HPLC纯度95%。
B:
将7.8g(10mmol)8,9-二碘代-1,2,3,4-四苯基苯并菲、1.0ml(11mmol)苯胺、2.4g(25mmol)叔丁醇钠、809mg(4mmol)三叔丁基膦、500mg(2mmol)乙酸钯(II)和100ml甲苯的混合物在回流下加热16小时。冷却之后,将100ml甲苯添加至该反应混合物,将该混合物每次用100ml水洗涤两次,经由硫酸镁干燥,然后在真空下除去溶剂。将以这种方式获得的固体用甲苯经由氧化铝(碱性,活性等级1)热蒸气提取四次,然后在真空下分级升华两次(p约10-6毫巴,T约370℃)。产率2.9g(4.6mmol),46%。纯度:HPLC纯度99.9%。
相似地,通过与相应的胺反应,获得如下的化合物:
B)器件实施例
实施例16:制造OLED
通过根据WO2004/058911的一般方法,制造根据本发明的OLED和根据现有技术的OLED,根据在此处描述的条件(层-厚度变化、使用的材料)对该方法进行了调整。
多种OLED的结果呈现于以下的实施例中(见表1、2、3、4)。对涂覆有150nm厚度的结构化ITO(氧化铟锡)的玻璃板,涂覆20nm的PEDOT(聚(3,4-亚乙二氧基-2,5-噻吩),通过自水中旋涂来施加;自德国,Goslar,H.C.Starck购得)以改善加工。这些涂覆的玻璃板形成对其施加OLED的基底。所述OLED基本上具有如下的层结构:基底/空穴注入层(HIL,使用HIL1,20nm)/空穴传输层(HTL,使用HTM1(参照)或根据本发明的HTM,20nm)/任选的电子阻挡层(EBL,10nm)/发光层(EML,使用根据本发明的单独的基质或混合基质M,40nm)/电子传输层(ETL,使用ETL1,20nm)/电子注入层(EIL,使用LiF,1nm)和最后的阴极。该阴极由厚度为100nm的铝层形成。所述OLED的确切结构,特别是空穴传导体或发光体层的结构,和在使用本发明化合物作为空穴传导体材料、磷光发光体基质材料,作为荧光发光体基质材料和作为荧光掺杂剂的这些OLED的情况下获得的结果,显示于表1、2、3和4中。
此处%数据涉及体积%。本发明化合物既用作磷光发光体基质材料又用作空穴传输材料的结果显示于表1、2、3和4中。本发明化合物既用作荧光发光体基质材料、用作蓝色荧光发光体又用作空穴传输材料的结果显示于表5中。
用于制造OLED的材料显示于表6中。
所有材料通过在真空室中热气相沉积来施加。在此处发光层总是由至少一种基质材料(主体材料)和与所述一种基质材料或多种基质材料以特定体积比例通过共蒸镀混合的发光掺杂剂(发光体)组成。
通过标准方法表征到此时为止仍未优化的OLED。为此目的,确定电致发光光谱、电流效率(以cd/A测量)和电压。在表中示出的效率和电压涉及在1000cd/m2的工作亮度下的相应值。
表1:发绿色光的OLED
表2:没有EBL的发绿色光的OLED
表3:发红色光的OLED
表4:没有EBL的发红色光的OLED
表5:发蓝色光的OLED
表6:所使用材料的结构式
如上文所给出实施例所清楚地表明的,根据本发明的材料特别适合于用作磷光发光体的基质材料和用作空穴传导体,其中它们导致了高效率和低工作电压。

Claims (16)

1.式(1)的中性化合物,
其中以下适用于使用的符号和标记:
X在每次出现时相同或不同地是BR2、C(R2)2、C=O、Si(R2)2、Sn(R2)2、NR2、O、S、SO、SO2、PR2或P(=O)R2
或者,X是下式(3)的基团,
A是C、Si或Sn;此处A上的虚线键表示与苯并菲键合;
Y是O;
Z在每次出现时相同或不同地是CR1
Ar1在每次出现时相同或不同地是具有5至60个环原子的芳族或杂芳族环系,所述环系可以被一个或多个非芳族基团R3取代;在此处两个与同一N原子或P原子键合的基团Ar1还可以经由单键或选自N(R4)、C(R4)2、O或S的桥连基彼此桥连;
R1在每次出现时相同或不同地选自H,D,F,CN,N(Ar1)2,N(R3)2,具有1至40个C原子的直链烷基或烷氧基基团或者具有3至40个C原子的支链或环状的烷基或烷氧基基团,其中所述烷基或烷氧基基团可以被一个或多个基团R3取代,并且其中一个或多个非相邻的CH2基团可以被R3C=CR3、C≡C、O或S代替,并且其中一个或多个H原子可以被D、F或CN代替,具有5至60个环原子的芳族或杂芳族环系,所述环系在每种情况下可以被一个或多个基团R3取代,其中两个或更多个与同一苯环键合的相邻取代基R1可以任选形成单环或多环的芳族或杂芳族环系,其中所述芳族环系在环系中包含6至60个C原子,所述杂芳族环系在环系中包含2至60个C原子和至少一个杂原子,条件是C原子和杂原子的总和至少为5;
R2在每次出现时相同或不同地选自具有1至20个C原子的直链烷基基团或者具有3至20个C原子的支链或环状的烷基基团,所述基团中的每个可以被一个或多个基团R3取代,其中一个或多个非相邻的CH2基团可以被R3C=CR3、C≡C、O或S代替,并且其中一个或多个H原子可以被D、F或CN代替,或者具有5至60个环原子的芳族或杂芳族环系,所述环系在每种情况下可以被一个或多个基团R3取代,其中两个与同一碳、硅、锗或锡原子键合的取代基R2可以任选彼此形成单环或多环的芳族或杂芳族环系,所述环系可以被一个或多个基团R3取代,其中所述芳族环系在环系中包含6至60个C原子,所述杂芳族环系在环系中包含2至60个C原子和至少一个杂原子,条件是C原子和杂原子的总和至少为5;
R3在每次出现时相同或不同地选自H,D,F,CN,N(R4)2,具有1至40个C原子的直链烷基或烷氧基基团或者具有3至40个C原子的支链或环状的烷基或烷氧基基团,其中所述烷基或烷氧基基团可以被一个或多个基团R4取代,其中一个或多个非相邻的CH2基团可以被R4C=CR4、C≡C、O或S代替,并且其中一个或多个H原子可以被D、F或CN代替,具有5至60个环原子的芳族或杂芳族环系,所述环系在每种情况下可以被一个或多个基团R4取代,其中两个或更多个相邻的取代基R3可以任选形成单环或多环的芳族或杂芳族环系,所述环系可以被一个或多个基团R4取代,其中所述芳族环系在环系中包含6至60个C原子,所述杂芳族环系在环系中包含2至60个C原子和至少一个杂原子,条件是C原子和杂原子的总和至少为5;
R4选自H,D,F,CN,具有1至20个C原子的脂族烃基团,具有5至30个环原子的芳族或杂芳族环系,其中一个或多个H原子可以被D、F、Cl、Br、I、CN或具有1至5个C原子的烷基基团代替,其中两个或更多个相邻的取代基R4可以彼此形成单环或多环的芳族或杂芳族环系,其中所述芳族环系在环系中包含6至60个C原子,所述杂芳族环系在环系中包含2至60个C原子和至少一个杂原子,条件是C原子和杂原子的总和至少为5;
n是0;
条件是,如果X代表C=O、O、S、SO或SO2,则式(1)中至少一个基团R1代表芳族或杂芳族环系。
2.根据权利要求1所述的化合物,其选自式(4)和(5)的化合物,
其中使用的符号具有在权利要求1中所给出的含义。
3.根据权利要求1或2所述的化合物,其选自式(4a)和(5a)的化合物,
其中使用的符号具有在权利要求1中所给出的含义。
4.根据权利要求3所述的化合物,其特征在于,在式(4a)的化合物中,X选自C(R2)2、Si(R2)2和N(R2),并且R2在每次出现时相同或不同地代表具有5至40个环原子的芳族或杂芳族环系,其在每种情况下还可以被一个或多个基团R3取代,并且其中两个基团R2还可以彼此形成芳族环系;
并且其特征在于,在式(5a)的化合物中,所述两个与A键合的苯并菲部分在每种情况下被相同地取代,并且A代表碳或硅。
5.用于制备根据权利要求1至4中的任一项所述的化合物的方法,所述方法通过1,12-二锂苯并菲衍生物与亲电子试剂的反应或者通过在金属催化偶联反应中卤素或氨基取代的苯并菲衍生物的反应进行制备。
6.一种低聚物或聚合物,其含有根据权利要求1至4中的任一项所述的化合物中的一种或多种,其中存在一个或多个从所述化合物至所述聚合物或低聚物的键。
7.根据权利要求1至4中的任一项所述的化合物或者根据权利要求6所述的低聚物或聚合物在电子器件中的用途。
8.包含至少一种根据权利要求1至4中的任一项所述的化合物或者根据权利要求6所述的低聚物或聚合物的电子器件,所述电子器件选自有机电致发光器件(OLED)、有机集成电路(O-IC)、有机场效应晶体管(O-FET)、有机薄膜晶体管(O-TFT)、有机发光晶体管(O-LET)、有机太阳能电池(O-SC)、有机光学检测器、有机光感受器、有机场猝熄器件(O-FQD)、发光电化学电池(LEC)、有机激光二极管(O-laser)和有机等离子体发射器件。
9.根据权利要求8所述的电子器件,其特征在于,它是有机电致发光器件,并且根据权利要求1至4中的任一项所述的化合物用作荧光发光体或磷光发光体的基质材料和/或用作荧光发光体和/或用于空穴阻挡层中和/或用于电子传输层中和/或用于电子阻挡或激子阻挡层中和/或用于空穴传输或空穴注入层中和/或用于光耦合输出层中。
10.根据权利要求9所述的有机电致发光器件,其特征在于,根据权利要求1至4中的任一项所述的化合物用作磷光发光体的基质材料,并且其特征在于,至少一个基团R1代表N(Ar1)2或者代表具有5至60个环原子的芳族或杂芳族环系,所述环系可以被一个或多个基团R3取代,其中所述基团Ar1或者在Ar1上的基团或者所述芳族或杂芳族环系或者在所述芳族或杂芳族环系上的基团R3不含具有超过10个C原子的稠合芳基基团,并且不含其中超过两个芳基或6元杂芳基基团直接稠合至彼此上的稠合杂芳基基团。
11.根据权利要求10所述的有机电致发光器件,其特征在于,至少一个基团R1和/或R2选自苯基,邻位、间位或对位的联苯,邻位、间位或对位的三联苯,邻位、间位、对位或支链的四联苯,芴或螺二芴,其中的每个可以被一个或多个基团R3取代,
和/或其特征在于,至少一个基团R1和/或R2选自式(8)至(38)的结构,
其中R3具有在权利要求1中所给出的含义,并且虚线键表示与所述苯并菲骨架或与X的键合;
和/或其特征在于,至少一个基团R1选自式(39)至(41)的结构,和/或其特征在于,至少一个基团R2选自式(40)的结构,
其中使用的符号具有在权利要求1中所给出的含义,并且,此外:
Ar2在每次出现时相同或不同地是具有5至24个环原子的芳族或杂芳族环系,其可以被一个或多个基团R3取代;在此处,所有基团Ar2的环原子在一起的总数不超过60;
E选自C(R4)2、NR4、O或S。
12.根据权利要求9至11中的任一项所述的有机电致发光器件,其特征在于,根据权利要求1至4中的任一项所述的化合物用作电子传输材料,并且至少一个基团R1代表具有5至40个环原子的缺电子杂芳族环系,其可以被一个或多个基团R3取代;和/或X代表BR2、C=O、SO、SO2或P(=O)(R2)2
13.根据权利要求12所述的有机电致发光器件,其特征在于,所述缺电子杂芳族环系R1和/或R2含有如下结构作为杂芳基基团:三嗪、嘧啶、吡嗪、哒嗪、吡啶、咪唑、吡唑、唑、二唑、三唑、噻唑、噻二唑、苯并咪唑、喹啉、异喹啉或喹喔啉。
14.根据权利要求12所述的有机电致发光器件,其特征在于,所述缺电子杂芳族环系R1和/或R2选自根据权利要求11所述的式(8)至(11)的结构或选自式(42)至(45)的结构,
其中R3具有在权利要求1中所给出的含义,并且虚线键表示与所述苯并菲骨架或与X的键合。
15.根据权利要求9至14中的任一项所述的有机电致发光器件,其特征在于,根据权利要求1至4中的任一项所述的化合物用作空穴传输材料或用作发光化合物,并且至少一个基团R1代表N(Ar1)2,代表二芳基氨基芳基基团,其中所述芳基基团包含6至60个C原子,或者代表具有5至40个环原子的富电子杂芳族环系,其可以被一个或多个基团R3取代;和/或X代表NR2或PR2
16.一种制剂,其包含至少一种根据权利要求1至4中的任一项所述的化合物或者一种或多种根据权利要求6所述的聚合物或低聚物和至少一种溶剂。
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CN103180407A (zh) 2013-06-26
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