CN104205390B - 电子器件 - Google Patents
电子器件 Download PDFInfo
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- CN104205390B CN104205390B CN201380013586.9A CN201380013586A CN104205390B CN 104205390 B CN104205390 B CN 104205390B CN 201380013586 A CN201380013586 A CN 201380013586A CN 104205390 B CN104205390 B CN 104205390B
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Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B19/00—Oxazine dyes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B21/00—Thiazine dyes
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/14—Styryl dyes
- C09B23/141—Bis styryl dyes containing two radicals C6H5-CH=CH-
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/008—Triarylamine dyes containing no other chromophores
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
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Abstract
本申请涉及一种电子器件,其含有阳极,阴极,在阳极和阴极之间的至少一个发光层,至少一个包含单三芳基胺作为主体材料的p掺杂层A,和至少一个包含单三芳基胺的层B。本发明还涉及一种p掺杂混合物,其包含式(II)、(III)或(IV)的单三芳基胺作为主体材料和电子受体化合物作为掺杂剂,还涉及该混合物在电子器件中的用途。
Description
技术领域
本发明涉及一种如下的电子器件,其包括阳极,阴极,在阳极和阴极之间的至少一个发光层,至少一个包含单三芳基胺作为主体的p掺杂层A,和至少一个包含单三芳基胺的层B。特别是,本发明涉及一种包含上述层结构的有机电致发光器件(OLED)。本发明还涉及一种p掺杂混合物,其包含式(II)、(III)或(IV)的单三芳基胺作为主体和电子受体化合物作为掺杂剂,还涉及该混合物在电子器件中的用途。
背景技术
包含有机层的电子器件是目前大力研究的课题。尤其感兴趣的是有机电致发光器件,它们例如被用于移动电子设备的显示器中或用作照明元件。
现有技术,例如EP 1463 130 A2和DE 10200703 1220 A1,公开了包括一个或多个包含掺杂剂和主体材料的p掺杂层的电子器件,其中该主体材料可以是有机氮化合物。
另外例如从US 5093698 A已知,在电子器件中掺杂空穴或电子传输层,可以显著提高其电导率。
现有技术,例如在EP 1885008 A1和JP 1995053955 A中,还公开了包含单三芳基胺作为空穴传输或发光层材料的电子器件。
开发新型电子器件极为重要的因素是器件的长期稳定性和它们的性能数据,特别是工作电压和效率。虽然已经取得了进展,但是与现有技术已知的实施方式相比,在所有这些方面仍然有改进的需求。
发明内容
本发明的技术目的是提供一种如下的电子器件,其与现有技术中已知的器件相比,在一个或多个上述长期稳定性和性能数据方面,具有更好的性能。
通过下文示出的本发明主题实现所述技术目的。
一种电子器件,包含:
-阳极,
-阴极,
-至少一个设置在阳极和阴极之间的发光层,
-至少一个包含单三芳基胺作为主体的p掺杂层A,和
-至少一个包含单三芳基胺的层B。
p掺杂层在此处是指其中已产生自由空穴并且已由此提高其电导率的层。可以在Chem.Rev.(化学综述)2007,107,1233中找到OLED或有机太阳能电池中掺杂传输层的综合讨论。
单三芳基胺是指如下的化合物,其包含单个三芳基胺基团。三芳基胺基团是如下的基团,其中三个芳基或杂芳基基团键合到氮原子上。该单三芳基胺优选不包含另外的芳基氨基基团。该单三芳基胺特别优选不包含另外的氨基基团。
所述电子器件优选具有如下的层结构,其中在阳极和发光层之间设置层A和层B。
层A优选设置在层B的阳极侧上。
层A、层B和所述发光层还优选是有机层,即,基本由一种或多种有机化合物组成的层。
另外优选在阳极和发光层之间具有如下层序列的器件,其中所述层彼此直接相邻:
-阳极
-层A
-层B
-发光层。
这种实施方式对应于在图1中描绘的电子器件(1)的结构,其中阳极(2)、层A(3)、层B(4)、发光层(5)、电子传输层(6)和阴极(7)一个接一个地设置并彼此直接相邻。
如图2中所示的,另外优选电子注入层(6a)存在于电子传输层(6)和阴极(7)之间。
在本发明的另一优选实施方式中,另外的层C存在于层B和发光层之间。对应于本实施方式的电子器件(1)的可能的层布置示于图3中,其具有层C(4a)。
层C优选包含一种有机胺,特别优选三芳基胺,非常特别优选单三芳基胺,如上文所限定的。
层C优选和发光层直接相邻。
还优选含单三芳基胺的层B或其它层与发光层直接相邻。
根据另一个可行的实施方式,层A’存在于阳极和层A之间,从而在阳极和发光层之间产生以下层结构,其中所述层彼此直接相邻:
-阳极
-层A’
-层A
-层B
-发光层。
对应于这种实施方式的电子器件(1)的一种可能的层布置示于图4中,其具有层A’(2a)。
层A’优选包含一种具有空穴传输性能的有机化合物,特别优选有机胺。层A’非常特别优选包含三芳基胺,例如单三芳基胺、双三芳基胺或含超过两个三芳基胺基团的化合物。层A’可以是p掺杂的。在这种情况下,优选含有有机电子受体化合物作为掺杂剂。在以下部分中示出这样的掺杂剂的优选实施方式。
通常,所述电子器件还可以包括另外的层,例如另外的空穴传输层、电子传输层、耦合输出层、中间层、空穴阻挡层、电子阻挡层、激子阻挡层、电荷产生层和/或有机或无机p/n结。这些层的优选布置和功能和组合是本领域普通技术人员所已知的。
通常优选的是,阳极和发光层之间的层都包含至少一种单三芳基胺。特别优选地,其除了单三芳基胺之外不包含其它三芳基胺化合物。非常特别优选地,一种或多种相同的单三芳基胺存在于阳极和发光层之间的所有层中。
所述p掺杂层A的厚度优选为1到500nm,特别优选5到300nm,非常特别优选8到250nm。
所述p掺杂层A优选包含一种是电子受体化合物的掺杂剂。该掺杂剂特别优选地能够氧化所述单三芳基胺,即具有足够高的氧化还原电位,特别是比所述单三芳基胺的氧化还原电位要高的氧化还原电位。
根据一个优选实施方式,所述掺杂剂具有如下的LUMO,其比所述单三芳基胺的HOMO高不超过0.3eV,优选高不超过0.2eV,特别优选高不超过0.1eV。所述掺杂剂最优选具有如下的LUMO,其等于或低于所述单三芳基胺的HOMO。
对本发明应用的目的,HOMO和LUMO的位置是通过使用“Gaussian03W”(高斯公司)进行量子化学计算而确定的,如实施例中所明确示出的。
所述掺杂剂的LUMO优选地小于-4.6eV,特别优选小于-4.8eV,非常特别优选小于-5.0eV。所述掺杂剂最优选具有小于-5.1eV的LUMO。
适当的掺杂剂原则上是如下的所有的化合物,其是电子受体化合物和能够通过氧化主体而增加有机层的电导率。本领域普通技术人员在其普通专业常识的范围里不需太大的努力就能够确定适合的化合物。
特别适合的掺杂剂是在WO 2011/073149、EP 1968131、EP 2276085、EP 2213662、EP 1722602、EP 2045848、DE 102007031220、US 8044390、US 8057712、WO 2009/003455、WO2010/094378、WO 2011/120709、US 2010/0096600和WO 2012/095143中公开的化合物。
所述p掺杂层A的掺杂剂优选地选自醌二甲烷化合物,氮杂茚并芴二酮,氮杂萘并苯,氮杂苯并菲,I2,金属卤化物,优选过渡金属的卤化物,金属氧化物,优选含至少一种过渡金属或第3主族金属的金属氧化物,和过渡金属络合物,优选Cu、Co、Ni、Pd和Pt与含至少一个氧原子作为键合点的配体的络合物。
此外,所述掺杂剂优选是过渡金属氧化物,优选铼、钼和钨的氧化物,特别优选Re2O7、MoO3、WO3和ReO3。
此外,所述掺杂剂优选是具有电子受体性质的有机化合物,特别是下列化合物:
所述掺杂剂优选以如下的浓度存在于层A中:0.1至20体积%,优选0.5至12体积%,特别优选1至8体积%,非常特别优选2至6体积%。
除了所述掺杂剂和单三芳基胺外,所述p掺杂层A还可包含另外的化合物,例如具有空穴传输性能的另外的掺杂剂和/或另外的化合物。
根据一种优选实施方式,所述p掺杂层具有如下的电导率,其大于10-8S/cm,特别优选大于10-7S/cm,非常优选大于10-6S/cm,最优选大于10-5S/cm。
薄层的电导率可以利用两点法进行测量,其中将包括导电材料例如金或氧化铟锡的触头施加至基底。然后将待检查的薄层施加到整个基底区域,使触头被该层覆盖。施加电压到触头后,则测量产生的电流。从以这种方式测定的电阻,触头的几何形状和试样厚度给出层的电导率。在掺杂有机层上的这种测量,例如,在EP 1786050 A1中有描述。可选地,四点法可用于测定电导率,如在van der Pauw等人,Philips Technical Review(飞利浦技术综述)1959/1960,第20卷,220,和van der Pauw等人,Philips Research Reports(飞利浦研究报告)1958,第13卷,1中所描述的。
根据一个优选的实施方式,相同的单三芳基胺存在于层A和层B中。
根据另一个优选的实施方式,相同的单三芳基胺存在于层B和层C中。
根据另一个优选的实施方式,相同的单三芳基胺存在于层A和层C中。
根据另一个优选的实施方式,相同的单三芳基胺存在于层A、层B和层C中。
优选地,所述单三芳基胺,尤其是层A和层B中的单三芳基胺,是式(I)的化合物:
式(I)
其中:
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,其可由一个或多个基团R1取代;
R1在每次出现时相同或不同地是H,D,F,Cl,Br,I,CHO,C(=O)R2,P(=O)(R2)2,S(=O)R2,S(=O)2R2,CR2=CR2R2,CN,NO2,Si(R2)3,OSO2R2,具有1至40个C原子的直链烷基、烷氧基或硫代烷氧基基团或者具有2至40个C原子的直链烯基或炔基基团或者具有3至40个C原子的支链或环状的烷基、烯基、炔基、烷氧基或硫代烷氧基基团,所述基团中的每个可被一个或多个基团R2取代,其中一个或多个非相邻的CH2基团可被R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、S或CONR2代替,和其中一个或多个H原子可被D、F、Cl、Br、I、CN或NO2代替,或具有5至60个芳族环原子的芳族或杂芳族环系,其在每种情况下可由一个或多个基团R2取代,或具有5至60个芳族环原子的芳氧基或杂芳氧基基团,其可由一个或多个基团R2取代,或这些体系的组合;两个或更多个相邻取代基R1此处还可彼此形成单环或多环的脂族或芳族环系;和
R2在每次出现时相同或不同地是H,D,CN或具有1至20个C原子的脂族、芳族和/或杂芳族的烃基团,其中,H原子还可被D或F代替;两个或更多个相邻的取代基R2此处还可彼此形成单环或多环的脂族或芳族环系。
在本发明意义上的芳族环系在环系中含有6至60个C原子。在本发明意义上的杂芳族环系含有5至60个芳族环原子,其中的至少一个是杂原子。所述杂原子优选选自N、O和/或S。在本发明意义上的芳族或杂芳族环系旨在被认为是指不必仅包含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通过非芳族单元(优选小于非H原子的10%)而连接,该非芳族单元例如为sp3-杂化的C、Si、N、O或Si原子,sp2-杂化的C或N原子,或sp-杂化的C原子。因此,例如,和其中两个或更多个芳基基团例如通过直链或环状的烷基、烯基或炔基基团或通过甲硅烷基基团而连接的体系一样,诸如芴、9,9′-螺二芴、9,9′-二芳基芴、三芳基胺、二芳基醚、茋等的体系同样旨在被认为是在本发明意义上的芳族环系。此外,其中两个或更多个芳基或杂芳基通过单键彼此连接的体系,例如,诸如联苯、三联苯或二苯基三嗪的体系,也被认为是在本发明的意义上的芳族或杂芳族环系。
在每种情况下还可以被上文所限定基团取代并可以经由任何希望的位置与所述芳族或杂芳族基团连接的具有5-60个芳族环原子的芳族或杂芳族环系,特别被认为是指衍生于如下物质的基团或这些基团的组合:苯、萘、蒽、苯并蒽、菲、苯并菲、芘、苝、荧蒽、并四苯、并五苯、苯并芘、联苯、偶苯、三联苯、三聚苯、四联苯、芴、螺二芴、二氢菲、二氢芘、四氢芘、顺式或反式茚并芴、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、吲哚并咔唑、茚并咔唑、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、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。
为了本发明的目的,其中单独的H原子或CH2基团还可以被所述基团定义下的上述基团取代的具有1至40个C原子的直链烷基基团或具有3至40个C原子的支链或环状的烷基基团或具有2至40个C原子的烯基或炔基基团,优选被认为是指如下的基团: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、环戊基、新戊基、正己基、环己基、新己基、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、己炔基或辛炔基。具有1至40个C原子的烷氧基或硫代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、2,2,2-三氟乙氧基、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、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。
Ar1优选是具有6至40个芳族环原子的芳族或杂芳族环系,特别优选具有6至30个芳族环原子的芳族环系,非常特别优选具有12至30个芳族环原子的芳族环系。
优选至少一个基团Ar1代表有12至30个芳族环原子的芳族环系,和优选地选自联苯、三联苯、四联苯、螺二芴、芴和茚并芴,其中的每个可以由一个或多个基团R1取代。
通常,R1优选在每次出现时相同或不同地是H,D,F,CN,Si(R2)3,N(R2)2,具有1至20个C原子的直链烷基或烷氧基基团或具有3至20个C原子的支链或环状的烷基或烷氧基基团,其中上述基团中的每个可以被一个或多个基团R2取代和其中上述基团中的一个或多个CH2基团可以被-C≡C-、-R2C=CR2-、Si(R2)2、C=O、C=NR2、-NR2-、-O-、-S-、-C(=O)O-或-C(=O)NR2-代替,或具有5至20个芳族环原子的芳族或杂芳环系,其在每种情况下可以由一个或多个基团R2取代,其中两个或更多个基团R1可以彼此连接和可形成环。
所述单三芳基胺优选符合式(II)、(III)或(IV)中的一个:
式(II)
式(III)
式(IV)
其中:
Z在每次出现时相同或不同地是N或CR1,其中如果键合取代基,则Z等于C;
Ar2是具有5至20个芳族环原子的芳族或杂芳族环系,其可被一个或多个基团R1取代;
Ar3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,其可被一个或多个基团R1取代;
R1在每次出现时相同或不同地是H,D,F,Cl,Br,I,CHO,C(=O)R2,P(=O)(R2)2,S(=O)R2,S(=O)2R2,CR2=CR2R2,CN,NO2,Si(R2)3,OSO2R2,具有1至40个C原子的直链烷基、烷氧基或硫代烷氧基基团或者具有2至40个C原子的直链烯基或炔基基团或者具有3至40个C原子的支链或环状的烷基、烯基、炔基、烷氧基或硫代烷氧基基团,所述基团中的每个可被一个或多个基团R2取代,其中一个或多个非相邻的CH2基团可被R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、S或CONR2代替,和其中一个或多个H原子可被D、F、Cl、Br、I、CN或NO2代替,或具有5至60个芳族环原子的芳族或杂芳族环系,其在每种情况下可由一个或多个基团R2取代,或具有5至60个芳族环原子的芳氧基或杂芳氧基基团,其可由一个或多个基团R2取代,或这些体系的组合;两个或更多个相邻取代基R1此处还可彼此形成单环或多环的脂族或芳族环系;
R2在每次出现时相同或不同地是H,D,CN或具有1至20个C原子的脂族、芳族和/或杂芳族的烃基团,其中,H原子还可被D或F代替;两个或更多个相邻的取代基R2此处还可彼此形成单环或多环的脂族或芳族环系;和
n是0或1。
在式(II)、(III)和(IV)中,优选每个芳族环中不超过三个基团Z等于N。特别优选每个芳族环中0、1或2个基团Z等于N。非常特别优选地,所有基团Z等于CR1,或者如果键合取代基,则所有基团Z等于C。
在式(II)、(III)和(IV)中的Ar2优选是具有6到18个芳族环原子的芳族或杂芳族环系,特别优选具有6至18个芳族环原子的芳族环系,其可以由一个或多个基团R1取代。
在根据本发明的器件中使用的单三芳基胺的实例是下文示出的:
本发明还涉及一种包含单三芳基胺的p掺杂混合物。
该混合物优选包含至少一种上文限定的式(II)、(III)或(IV)的单三芳基胺。对于式(II)、(III)或(IV)的化合物,上文示出的优选实施方式适用于此处。
所述p掺杂混合物优选包含一种是电子受体化合物的掺杂剂。适用上文示出的掺杂剂的优选实施方式。特别地,所述掺杂剂优选地选自醌二甲烷化合物,氮杂茚并芴二酮,氮杂萘并苯,氮杂苯并菲,I2,金属卤化物,优选过渡金属的卤化物,金属氧化物,优选含至少一种过渡金属或第3主族金属的金属氧化物,和过渡金属络合物,优选Cu、Co、Ni、Pd和Pt与含至少一个氧原子作为键合点的配体的络合物。
此外,所述掺杂剂优选是过渡金属氧化物,优选铼、钼和钨的氧化物,特别优选Re2O7、MoO3、WO3和ReO3。
此外优选如上文所示出的式(D-1)至(D-12)的掺杂剂化合物。
优选所述p掺杂混合物以如下的浓度包含所述掺杂剂:0.1至20体积%,优选0.5至12体积%,特别优选1至8体积%,非常特别优选2至6体积%。
根据本发明的电子器件优选地选自有机集成电路(OIC)、有机场效应晶体管(OFET)、有机薄膜晶体管(OTFT)、有机发光晶体管(OLET)、有机太阳能电池(OSC)、有机光检测器、有机光感受器、有机场猝熄器件(OFQD)、有机发光电化学电池(OLEC)、有机激光二极管(O-laser)和有机电致发光器件(OLED)。该电子器件特别优选是有机电致发光器件。
所述电子器件的发光层可以是荧光或磷光发光层。所述器件中可存在一个或多个发光层。
本发明电子器件可以包括多个发光层。在这种情况下,特别优选这些发光层总共具有多个在380nm和750nm之间的发光峰值,导致总体上白色发光,即,将能够发荧光或发磷光且发蓝色或黄色或橙色或红色光的多种发光化合物用于所述发光层中。特别优选三层体系,即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WO 2005/011013)。应该指出的是,为了产生白光,在宽波长范围中发光的单独使用的发光体化合物,代替多种发特定颜色的发光体化合物,同样可能是适当的。
所述一个或多个发光层各自包含一种或多种发光体化合物,其可以是发磷光或发荧光的。
所述术语磷光掺杂剂通常包括如下的化合物:其中,通过自旋禁阻的跃迁而发光,所述自旋禁阻的跃迁例如是从激发三重态或自旋量子数比较高的态例如五重态的跃迁。
适当的磷光发光体特别是如下的化合物,其经适当激发时发光,优选在可见区发光,并且另外包含至少一种如下原子序数的原子,该原子序数大于20,优选大于38但小于84,特别优选大于56但小于80。使用的磷光掺杂剂优选是包含铜、钼、钨、铼、钌、锇、铑、铱、钯、铂、银、金或铕的化合物,特别是包含铱、铂或铜的化合物。
为了本发明的目的,所有发光的铱、铂或铜络合物都被认为是磷光化合物。
申请WO 2000/70655,WO 2001/41512,WO 2002/02714,WO 2002/15645,EP1191613,EP 1191612,EP 1191614,WO 2005/033244,2005/019373,和US 2005/0258742公开了磷光发光体的实例。一般地,根据现有技术用于磷光OLED的和在有机电致发光器件领域普通技术人员所已知的所有磷光络合物,都适用于根据本发明的器件中。本领域普通技术人员还将能够在不付出创造性劳动的情况下将其它磷光络合物与本发明化合物组合用于OLED中。
下文示出可在根据本发明的电子器件中使用的磷光发光体的特定实例:
优选的荧光掺杂剂选自如下类的芳基胺。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至氮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个芳族环原子。其优选的实例是芳族蒽胺、芳族蒽二胺、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一个二芳基氨基基团直接与蒽基团优选在9-位键合的化合物。芳族蒽二胺被认为是指其中两个二芳基氨基基团直接与蒽基团优选在9,10-位键合的化合物。以与此类似的方式,定义芳族的芘胺、芘二胺、胺和二胺,其中所述二芳基氨基基团优选与芘在1-位或在1,6-位键合。
除了一种或多种发光化合物外,所述发光层优选还包含一种或多种基质材料。
合适的基质材料,优选用于荧光发光体的合适的基质材料,是来自多种类别的物质的材料。优选的基质材料选自如下的类:低聚亚芳基(例如,根据EP 676461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,低聚亚芳基亚乙烯基(例如根据EP 676461的DPVBi或螺-DPVBi),多足金属络合物(例如根据WO 2004/081017的),空穴传导化合物(例如根据WO 2004/058911的),电子传导化合物,特别是酮、氧化膦、亚砜等(例如根据WO 2005/084081和WO 2005/084082的),阻转异构体(例如根据WO 2006/048268的),硼酸衍生物(例如根据WO 2006/117052的),或苯并蒽(例如根据WO 2008/145239的)。特别优选的基质材料选自如下的类别:含萘、蒽、苯并蒽和/或芘的低聚亚芳基或这些化合物的阻转异构体,低聚亚芳基亚乙烯基,酮,氧化膦和亚砜。非常特别优选的基质材料选自如下的类别:含蒽、苯并蒽、苯并菲和/或芘的低聚亚芳基或这些化合物的阻转异构体。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。
用于磷光发光体的优选基质材料是芳族胺,特别是三芳基胺,例如根据US 2005/0069729的,咔唑衍生物(例如CBP,N,N-双咔唑基联苯)或根据WO 2005/039246、US 2005/0069729、JP 2004/288381、EP 1205527或WO 2008/086851的化合物,桥连咔唑衍生物,例如根据WO 2011/088877和WO 2011/128017的,茚并咔唑衍生物,例如根据WO 2010/136109和WO 2011/000455的,氮杂咔唑衍生物,例如根据EP 1617710、EP 1617711、EP 1731584、JP2005/347160的,吲哚并咔唑衍生物,例如根据WO 2007/063754或WO 2008/056746的,酮,例如根据WO 2004/093207或WO 2010/006680的,氧化膦,亚砜和砜,例如根据WO 2005/003253的,低聚亚苯基,双极性基质材料,例如根据WO 2007/137725的,硅烷,例如根据WO 2005/111172的,氮杂硼杂环戊二烯或硼酸酯,例如根据WO 2006/117052的,三嗪衍生物,例如根据WO 2010/015306、WO 2007/063754或WO 2008/056746的,锌络合物,例如根据EP 652273或WO 2009/062578的,铝络合物,例如BAlq,二氮杂硅杂环戊二烯和四氮杂硅杂环戊二烯衍生物,例如根据WO 2010/054729的,二氮杂磷杂环戊二烯衍生物,例如根据WO 2010/054730的,和铝络合物,例如BAlQ。
可在本发明电子器件的空穴注入或空穴传输层中或电子阻挡层中或电子传输层中使用的合适的电荷传输材料,例如是在Y.Shirota等人,Chem.Rev.(化学综述)2007,107(4),953-1010中公开的化合物,或根据现有技术用于这些层中的其它材料。
可用于电子传输层的材料是根据现有技术在电子传输层中用作电子传输材料的所有材料。特别适当的是铝络合物,例如Alq3,锆络合物,例如Zrq4,苯并咪唑衍生物,三嗪衍生物,嘧啶衍生物,吡啶衍生物,吡嗪衍生物,喹喔啉衍生物,喹啉衍生物,二唑衍生物,芳族酮,内酰胺,硼烷,二氮杂磷杂环戊二烯衍生物和氧化膦衍生物。另外合适的材料为上述化合物的衍生物,如在JP 2000/053957、WO 2003/060956、WO 2004/028217、WO 2004/080975和WO 2010/072300中所公开的。
可用于根据本发明的电致发光器件中的空穴传输、空穴注入或电子阻挡层中的优选空穴传输材料,通常是茚并芴胺衍生物(例如根据WO 06/122630或WO 06/100896的),公开在EP 1661888中的胺衍生物,六氮杂苯并菲衍生物(例如根据WO 01/049806的),具有稠合芳族环的胺衍生物(例如根据US 5,061,569的),公开在WO 95/09147中的胺衍生物,单苯并茚并芴胺(例如根据WO 08/006449的),二苯并茚并芴胺(例如根据WO 07/140847的),螺二芴胺(例如根据WO 2012/034627或尚未公开的EP 12000929.5的),芴胺(例如根据尚未公开的申请EP 12005369.9、EP 12005370.7和EP 12005371.5的),螺二苯并吡喃胺(例如根据尚未公开的申请EP 11009127.9的)和二氢吖啶衍生物(例如根据尚未公开的EP11007067.9的)。
所述电子器件的阴极优选包含具有低逸出功的金属、金属合金或多层结构,其包含不同金属例如碱土金属、碱金属、主族金属或镧系元素(例如Ca、Ba、Mg、Al、In、Mg、Yb、Sm等)。同样合适的是包含碱金属或碱土金属和银的合金,例如包含镁和银的合金。在多层结构情况下,除所述金属之外,也可使用具有相对高逸出功的其它金属例如Ag或Al,在这种情况下,通常使用金属的组合,例如Ca/Ag、Mg/Ag或Ba/Ag。也可以优选在金属阴极和有机半导体之间引入具有高介电常数的材料的薄中间层。适合于该目的的例如是碱金属氟化物或碱土金属氟化物,但也可以是相应的氧化物或碳酸盐(例如LiF、Li2O、BaF2、MgO、NaF、CsF、Cs2CO3等)。此外,羟基喹啉锂(LiQ)可用于该目的。该层的层厚度优选为0.5至5nm。
所述阳极优选包含具有高逸出功的材料。所述阳极优选具有相对于真空大于4.5eV的逸出功。适于该目的的一方面是具有高氧化还原电势的金属,例如Ag、Pt或Au。另一方面,也可以优选金属/金属氧化物电极(例如Al/Ni/NiOx、Al/PtOx)。对于一些应用,至少一个电极必须是透明的或部分透明的,以利于有机材料辐射(有机太阳能电池),或耦合输出光(OLED、O-laser)。此处优选的阳极材料是导电的混合金属氧化物。特别优选氧化铟锡(ITO)或氧化铟锌(IZO)。此外优选导电的掺杂有机材料,特别是导电的掺杂聚合物。
优选地通过升华产生一个或多个层来制造所述电子器件。在这种方法中,在真空升华设备中,在小于10-5毫巴、优选小于10-6毫巴的初压下通过气相沉积施加所述材料。然而,所述初压在此处也可以甚至更低,例如小于10-7毫巴。
特别地,优选通过共升华掺杂剂和单三芳基胺来生产所述p掺杂层A。在例如SolarEnergy Materials&Solar Cells(太阳能材料和太阳能电池),2000,63,83-99中描述了用于此目的的方法。
同样优选通过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巴的压力下施加所述材料。该方法中的特别的例子是OVJP(有机蒸气喷印)方法,其中所述材料通过喷管直接施加,并且因此是结构化的(例如M.S.Arnold等人,Appl.Phys.Lett.(应用物理快报)2008,92,053301)。
此外优选从溶液中例如通过旋涂,或借助于任何希望的印刷方法例如丝网印刷、柔性版印刷、喷嘴印刷或平版印刷,但是特别优选LITI(光引发热成像,热转印)或喷墨印刷,来产生一个或多个层。对于这种目的,可溶性的化合物是必要的。可通过适当取代所述化合物实现足够的溶解性。
为制造本发明的电子器件,此外优选从溶液产生一个或多个层并通过升华方法产生一个或多个层。
所述器件在制造期间被(取决于应用)结构化,提供以接触并最后被密封,因为本发明器件的寿命在水和/或空气存在下会缩短。
附图说明
下图解释了本发明:
图1示出一种电子器件(1),其包括阳极(2)、层A(3)、层B(4)、发光层(5)、电子传输层(6)和阴极(7)。
图2示出一种电子器件(1),其包括阳极(2)、层A(3)、层B(4)、发光层(5)、电子传输层(6)、电子注入层(6a)和阴极(7)。
图3示出一种电子器件(1),其包括阳极(2)、层A(3)、层B(4)、层C(4a)、发光层(5)、电子传输层(6)、电子注入层(6a)和阴极(7)。
图4示出一种电子器件(1),其包括阳极(2)、层A’(2a)、层A(3)、层B(4)、发光层(5)、电子传输层(6)、电子注入层(6a)和阴极(7)。
具体实施方式
实施例
A)确定化合物的HOMO/LUMO位置
经由量子化学计算确定所述材料的HOMO位置和LUMO位置。为此,使用“Gaussian03W”软件包(Gaussian公司)。为了计算没有金属的有机物质,首先使用“GroundState/Semi-empirical/Default Spin/AM1/Charge 0/Spin Singlet”方法进行几何结构优化。然后,基于优化的几何结构进行能量计算。在这种情况下,使用具有“6-31G(d)”基集(电荷0,自旋单重态)的“TD-SFC/DFT/Default Spin/B3PW91”方法。对于有机金属化合物,经由“Ground State/Hartree-Fock/Default Spin/LanL2MB/Charge 0/Spin Singlet”方法优化几何结构。类似于如上所述的有机物质进行能量计算,区别在于对于金属原子使用“LanL2DZ”基集,而对于配体使用“6-31G(d)”基集。该能量计算给出以哈特里单位计量的HOMO HEh或LUMO LEh。由此,由此如下确定HOMO和LUMO值,其单位为电子伏特,其参照循环伏安法测量进行校准:
HOMO(eV)=((HEh*27.212)-0.9899)/1.1206
LUMO(eV)=((LEh*27.212)-2.0041)/1.385
为了本申请的目的,这些值被认为是材料的HOMO或LUMO。在表1中总结在实施例中采用的材料的值:
表1:材料的HOMO/LUMO值
B)化合物的制备
可根据普通专业知识制备使用的化合物。在例如JP 1995-053955中公开MA1的制备。在例如WO 2012/034672中公开MA2、MA6、MA7、MA11、MA20、MA25和MA27的制备。
C)OLED的制造
通过按照WO 2004/058911的一般方法制造本发明的OLED和现有技术的OLED,将该方法调整以适应此处所述的环境(层厚度的改变,材料)。
在下文实施例V1至E46中示出多种OLED的数据(见表2和表3)。涂有结构化ITO(氧化铟锡)的厚度50nm的玻璃板形成OLED的基底。湿洗(洗碟机,默克EXTRAN清洗剂)基底,随后通过在250℃加热15分钟进行干燥,和在涂覆前用氧等离子体处理。
将多个层施加到预处理的基底:第一空穴传输层(HTL1)/任选的第二空穴传输层(HTL2)/与EML直接相邻的空穴传输层(HTL3)/发光层(EML)/电子传输层(ETL)/任选的电子注入层(EIL)和最后的厚度100nm的铝阴极。所述OLED的确切结构如表2所示。用于生产所述OLED所需的材料示于表4中。
在实施例E16、E44中,在EML和ETL之间另外存在材料IC1的10nm厚的层。
在实施例E42、E43中,在EML和ETL之间另外存在材料IC2层的10nm厚的层。
在实施例E15和E16中,在ITO和HTL1之间另外存在PEDOT:PSS(聚(3,4-亚乙基二氧噻吩)聚(磺化苯乙烯),作为CLEVIOSTM P VP AI 4083购自德国贺利氏贵金属股份有限公司(Heraeus Precious Metals GmbH Deutschland),从水溶液中通过旋涂施加)的20nm厚的层。
在真空室中通过热蒸汽沉积施加其它材料。此处发光层总是由至少一种基质材料(主体材料)和发光掺杂剂(发光体)组成,以特定体积比例通过共蒸发将发光掺杂剂与一种或多种基质材料混合。此处诸如M1:D1(95%:5%)的表达是指,材料M1以95体积%的比例存在于该层中,和D1以5体积%的比例存在于该层中。类似地,电子传输层也可由两种材料的混合物组成。
通过标准的方法表征OLED。为此目的,确定电致发光光谱,电流效率(测量为cd/A),功率效率(测量为lm/W)和外量子效率(EQE,测定为百分比),其作为发光密度的函数,从显示朗伯发射特性的电流/电压/发光密度特性线(IUL特征线)计算,和寿命。在1000cd/m2的发光密度下测定电致发光光谱,且由此计算CIE 1931 x和y颜色坐标。表3中的术语U1000表示1000cd/m2的发光密度需要的电压。CE1000和PE1000分别表示在1000cd/m2实现的的电流和功率效率。最后,EQE1000表示在工作发光密度为1000cd/m2时外部量子效率。寿命LT被定义为在恒定电流密度情况下工作时,发光密度从初始光密度下降到特定比例A之后经历的时间(显示在表3的“JLT”列中)。
将多种OLED的数据总结于表3中。实施例V1-V16是根据现有技术的对比例,实施例E1-E46显示了本发明OLED的数据。
下文更详细地解释一些实施例,以示例根据本发明的OLED的优点。然而,应该指出的是,这仅仅代表了对表3所示数据的一种选择。
与包含p掺杂单胺作为HTL1和二胺NPB作为与EML相邻的HTL3的OLED相比,包含相同HTL1和单胺MA2作为HTL3的OLED显示出明显更好的效率和寿命,和稍微更好的电压(实施例V1和E9)。
具有蓝色荧光掺杂剂D2的实施例(V2-V7,V10,E5-E11,E14)显示,作为HTL1的p掺杂单胺和与EML相邻的单胺的组合具有最好的结果。如果根据现有技术的二胺、胺-咔唑或四胺用作HTL1、HTL2或作为与EML直接相邻的HTL3,则性能数据没那么好。在使用单胺MA2的p掺杂层与和EML直接相邻的p掺杂四胺SPA1和MA2的组合时,同样获得了很好的性能数据(实施例E14)。
如果咔唑-胺CbzA1用于HTL3中(即与EML直接接触)和p掺杂单胺MA1与蓝色掺杂剂D1组合使用,则与在HTL3中使用单胺MA1或MA2的情况下相比,获得更高的电压和更差的效率和寿命(实施例E1、E2和E12)。如果使用绿色磷光掺杂剂TEG1代替蓝色荧光掺杂剂D1,则同样适用(实施例E3、E4和E13)。
如果在其它空穴传输层中也使用p掺杂的单胺,则得到特别好的寿命(对比例E1和E2和E3和E4)。
此外,在电子注入非常好的情况下,与单胺MA2相比,使用仅苯基取代的单胺MA1是有利的(对比例E10和E11)。虽然所示OLED显示较短的寿命,然而与具有较低电子注入的类似OLED相比,它们显示出比较低的电压,这可能有利于一些应用。
实施例E18至E46显示,多种不同的化合物可用作根据本发明的单三芳基胺,而不会改变本发明的基本技术效果。化合物MA1至MA29特别是包括芴基单三芳基胺,氧杂蒽单三芳基胺,螺二芴单三芳基胺,茚并芴单三芳基胺和另外种类的物质。
表2:OLED的结构
表3:OLED的数据
表4:OLED的材料的结构式
Claims (16)
1.一种电子器件,其包含:
-阳极,
-阴极,
-至少一个设置在阳极和阴极之间的发光层,
-至少一个包含单三芳基胺作为主体的p掺杂层A,和
-至少一个包含单三芳基胺的层B,
其中所述单三芳基胺符合式(III)和(IV)中的一个,并且所述单三芳基胺不包含另外的氨基基团:
其中:
Z在每次出现时相同或不同地是N或CR1,其中如果键合取代基,则Z等于C;
Ar2是具有5至20个芳族环原子的芳族或杂芳族环系,其可被一个或多个基团R1取代;
Ar3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,其可被一个或多个基团R1取代;
R1在每次出现时相同或不同地是H,D,F,Cl,Br,I,CHO,C(=O)R2,P(=O)(R2)2,S(=O)R2,S(=O)2R2,CR2=CR2R2,CN,NO2,Si(R2)3,OSO2R2,具有1至40个C原子的直链烷基、烷氧基或硫代烷氧基基团或者具有2至40个C原子的直链烯基或炔基基团或者具有3至40个C原子的支链或环状的烷基、烯基、炔基、烷氧基或硫代烷氧基基团,所述基团中的每个可被一个或多个基团R2取代,其中一个或多个非相邻的CH2基团可被R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、O或S代替,和其中一个或多个H原子可被D、F、Cl、Br、I、CN或NO2代替,或具有5至60个芳族环原子的芳族或杂芳族环系,其在每种情况下可由一个或多个基团R2取代,或具有5至60个芳族环原子的芳氧基或杂芳氧基基团,其可由一个或多个基团R2取代,或这些体系的组合;两个或更多个相邻取代基R1此处还可彼此形成单环或多环的脂族或芳族环系;
R2在每次出现时相同或不同地是H,D,CN或具有1至20个C原子的脂族、芳族和/或杂芳族的烃基团,其中,H原子还可被D或F代替;两个或更多个相邻的取代基R2此处还可彼此形成单环或多环的脂族或芳族环系;和
n是0或1。
2.根据权利要求1所述的电子器件,其特征在于层A和层B设置在阳极和发光层之间。
3.根据权利要求1或2所述的电子器件,其特征在于层A设置在层B的阳极侧上。
4.根据权利要求1或2所述的电子器件,其特征在于包含单三芳基胺的层B或其它层与发光层直接相邻。
5.根据权利要求1或2所述的电子器件,其特征在于在阳极和发光层之间的所有层中存在一种或多种相同的单三芳基胺。
6.根据权利要求1或2所述的电子器件,其特征在于所述p掺杂层A包含是电子受体化合物的掺杂剂。
7.根据权利要求1或2所述的电子器件,其特征在于层A的掺杂剂选自如下的化合物,其LUMO比所述单三芳基胺的HOMO高不超过0.3eV。
8.根据权利要求1或2所述的电子器件,其特征在于层A的掺杂剂选自醌二甲烷化合物,氮杂茚并芴二酮,氮杂萘并苯,氮杂苯并菲,I2,金属卤化物,金属氧化物,和过渡金属络合物。
9.根据权利要求8所述的电子器件,其中所述金属卤化物是过渡金属的卤化物。
10.根据权利要求8所述的电子器件,其中所述金属氧化物是含至少一种过渡金属或第3主族金属的金属氧化物。
11.根据权利要求8所述的电子器件,其中所述过渡金属络合物是Cu、Co、Ni、Pd和Pt与含至少一个氧原子作为键合点的配体的络合物。
12.根据权利要求1或2所述的电子器件,其特征在于层A的掺杂剂以如下的浓度存在:0.1至20体积%。
13.根据权利要求12所述的电子器件,其中所述浓度为0.5至12体积%。
14.根据权利要求12所述的电子器件,其中所述浓度为1至8体积%。
15.根据权利要求12所述的电子器件,其中所述浓度为2至6体积%。
16.根据权利要求1或2所述的电子器件,其选自有机集成电路(OIC)、有机场效应晶体管(OFET)、有机薄膜晶体管(OTFT)、有机发光晶体管(OLET)、有机太阳能电池(OSC)、有机光检测器、有机光感受器、有机场猝熄器件(OFQD)、有机发光电化学电池(OLEC)、有机激光二极管(O-laser)和有机电致发光器件(OLED)。
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- 2013-03-05 KR KR1020217016629A patent/KR20210068605A/ko not_active Application Discontinuation
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KR102268695B1 (ko) | 2021-06-23 |
JP6254107B2 (ja) | 2017-12-27 |
KR20180133545A (ko) | 2018-12-14 |
KR20190136129A (ko) | 2019-12-09 |
EP4369378A2 (de) | 2024-05-15 |
KR20190003789A (ko) | 2019-01-09 |
EP2826079A1 (de) | 2015-01-21 |
TW201348403A (zh) | 2013-12-01 |
KR20140146103A (ko) | 2014-12-24 |
US20150115239A1 (en) | 2015-04-30 |
JP2015516674A (ja) | 2015-06-11 |
KR20210068605A (ko) | 2021-06-09 |
US9871201B2 (en) | 2018-01-16 |
EP4369378A3 (de) | 2024-08-14 |
WO2013135352A1 (de) | 2013-09-19 |
KR102268696B1 (ko) | 2021-06-23 |
TWI620810B (zh) | 2018-04-11 |
EP3460864A1 (de) | 2019-03-27 |
EP2826079B1 (de) | 2021-01-20 |
CN104205390A (zh) | 2014-12-10 |
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