CN101932581B - 具有通过亚苯基连接的取代的吡啶基和吡啶并吲哚环结构的化合物及有机电致发光器件 - Google Patents
具有通过亚苯基连接的取代的吡啶基和吡啶并吲哚环结构的化合物及有机电致发光器件 Download PDFInfo
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- CN101932581B CN101932581B CN200980103718.0A CN200980103718A CN101932581B CN 101932581 B CN101932581 B CN 101932581B CN 200980103718 A CN200980103718 A CN 200980103718A CN 101932581 B CN101932581 B CN 101932581B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 121
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- 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
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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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
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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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
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
Abstract
本发明公开一种由通式(1)表示的化合物,该化合物具有通过亚苯基连接的取代的吡啶基和吡啶并吲哚环结构。还公开具有一对电极和夹置于所述电极之间的至少一层有机层的有机电致发光器件,其中所述至少一层有机层包含所述化合物。(在所述式中,Ar表示取代或未取代的芳族烃基、芳族杂环基或稠合多环芳基;R1至R14可以相同或不同,并且各自表示氢原子、氟原子、氯原子、氰基、三氟甲基、具有1至6个碳原子的线性或支化烷基,或者取代或未取代的芳族烃基、芳族杂环基或稠合多环芳基;n表示1至3的整数;W、X、Y和Z分别表示碳原子或氮原子。在此方面,W、X、Y和Z中仅之一表示氮原子时,所述氮原子不具有取代基R7、R8、R9或R10)。
Description
技术领域
本发明涉及适用于有机电致发光(EL)器件的化合物和器件,该有机电致发光(EL)器件为适用于各种显示器件的自发光器件。更具体地,本发明涉及具有通过亚苯基连接的取代的吡啶基和吡啶并吲哚环结构的化合物及涉及使用该化合物的有机电致发光器件。
背景技术
由于有机EL器件是自发光器件,与液晶器件相比它们明亮并且可视性优异而且能够赋予清楚的显示,以致有机EL器件已经得到积极地研究。
1987年,Eastman Kodak公司的C.W.Tang等人通过研发具有多层结构的器件将使用有机材料的有机EL器件投入实际使用,在所述多层结构中将各种职能分配至各材料。他们形成了能够输送电子的荧光材料和能够输送空穴的有机材料的层压体,以致将两种电荷注入荧光材料层中而发光,从而在10V以下的电压下得到1000cd/m2的高亮度(参见例如专利文献1和2)。
专利文献1:JP-A-8-48656
专利文献2:日本专利3194657
至今为止,已经对实际利用有机EL器件进行了许多改进,并且通过下述电致发光器件已经实现高效率和耐久性,在该电致发光器件中将阳极、空穴注入层、空穴输送层、发光层、电子输送层、电子注入层和阴极依次设置在基板上,以进一步划分各种职能(参见例如非专利文献1)。
非专利文献1:Japan Society of Applied Physics Ninth Workshop Preprint,pp.55-61(2001)
此外,为了进一步改进发光效率,已经尝试利用三重态激子(triplet exciton)并且已经研究了利用磷光材料(参见例如非专利文献2)。
非专利文献2:Japan Society of Applied Physics Ninth Workshop Preprint,pp.23-31(2001)
所述发光层也可以通过用荧光材料或磷光材料掺杂通常称作基质材料(host material)的电荷输送化合物来制备。如在上述Workshop Preprints中所述,在有机EL器件中有机材料的选择显著地影响各种性能如器件的效率和耐久性。
在有机EL器件中,从两个电极注入的电荷在发光层中再结合以实现发光。然而,由于空穴的迁移率高于电子的迁移率,产生由于部分空穴经过发光层而导致的效率降低的问题。因此,需要开发电子迁移率高的电子输送材料。
通常将代表性的发光材料三(8-羟基喹啉)铝(下文中称作Alq3)也用作电子输送材料。然而,由于其具有5.8eV的功函数,认为该材料不具有空穴阻挡能力。
作为防止部分空穴通过发光层和改进电荷在发光层中再结合的概率的技术,存在插入空穴阻挡层的方法。作为空穴阻挡材料,迄今为止已经提出了三唑衍生物(参见例如专利文献3)、浴铜灵(下文中称作BCP)和铝的混合配体配合物(BAlq)(参见例如非专利文献2)等。
例如,作为空穴阻挡能力优异的电子输送材料,提出了3-(4-联苯基)-4-苯基-5-(4-叔丁基苯基)-1,2,4-三唑(下文中称作TAZ)(参见例如专利文献3)。
专利文献3:日本专利2734341
由于TAZ具有高达6.6eV的功函数并且由此显示出高空穴阻挡能力,因此将其用作要层压在通过真空沉积或涂覆等制备的荧光发光层或磷光发光层的阴极侧上的电子输送空穴阻挡层,并且有助于增加有机EL器件的效率(参见例如非专利文献3)。
非专利文献3:Fiftieth Meeting of Japan Society of Applied Physics and Related Societies,28p-A-6 Lecture Preprint,p.1413(2003)
然而,TAZ带有具有低电子输送性的大问题,需要制备与具有较高电子输送性的电子输送材料组合的有机EL器件(参见例如非专利文献4)。
非专利文献4:Japan Society of Applied Physics,Journal of Organic Molecules/Bioelectronics Section,Vol.11,No.1,pp.13-19(2000)
此外,BCP具有高达6.7eV的功函数和高空穴阻挡能力,但是具有83℃的低玻璃化转变温度(Tg),以致其薄膜稳定性不良并且因此认为其不能充分地起到空穴阻挡层的功能。
所有材料的薄膜稳定性不足或者阻挡空穴功能不足。为了改进有机EL器件的特性,期望开发电子注入/输送性能和空穴阻挡能力优异并且薄膜状态高度稳定的有机化合物。
发明内容
发明要解决的问题
本发明的目的是提供具有优异性能的有机化合物,作为用于具有高效率和高耐久性的有机电致发光器件的材料,所述有机化合物的电子注入/输送性能优异、具有空穴阻挡能力并且薄膜状态高度稳定,还提供使用该化合物的具有高效率和高耐久 性的有机电致发光器件。
作为通过本发明提供的有机化合物的物理性质,可以提及(1)良好的电子注入特性,(2)高电子迁移率,(3)优异的空穴阻挡能力,(4)良好的薄膜状态稳定性和(5)优异的耐热性。此外,作为通过本发明提供的有机EL器件的物理性质,可以提及(1)高发光效率,(2)低发光开始电压(emission initiation voltage)和(3)低实际驱动电压。
用于解决问题的方案
因此,为了达到以上目的,在注意到显示出对电子的亲和性的吡啶环的氮原子具有与金属配位的能力和耐热性优异的事实的情况下,本发明人已经设计和化学合成了具有通过亚苯基连接的取代的吡啶基和吡啶并吲哚环结构的化合物。本发明人已经使用该化合物实验性地生产出各种有机EL器件,并且已经深入地进行了器件性能的评价。结果,他们已经完成本发明。
即,本发明提供了:具有通过亚苯基连接的取代的吡啶基和吡啶并吲哚环结构的化合物,该化合物由通式(1)表示;包括一对电极和插置于所述电极之间的至少一层有机层的有机EL器件,其中所述至少一层有机层包含该化合物:
[化学式1]
其中Ar表示取代或未取代的芳族烃基、取代或未取代的芳族杂环基或者取代或未取代的稠合多环芳基;R1至R14可以彼此相同或不同并且各自表示氢原子、氟原子、氯原子、氰基、三氟甲基、具有1至6个碳原子的线性或支化烷基、取代或未取代的芳族烃基、取代或未取代的芳族杂环基或者取代或未取代的稠合多环芳基;n表示1至3的整数;W、X、Y和Z分别表示碳原子或氮原子,条件是W、X、Y和Z中仅之一表示氮原子时,所述氮原子不具有取代基R7、R8、R9或R10。
在通式(1)中由Ar表示的取代或未取代的芳族烃基、取代或未取代的芳族杂环基或者取代或未取代的稠合多环芳基中的“芳族烃基”、“芳族杂环基”或“稠合多环芳基”的具体实例包括:苯基、联苯基、三联苯基、四联苯基(tetrakisphenyl group)、苯乙烯基、萘基、蒽基、苊基、芴基、菲基、茚基、芘基、嘧啶基、呋喃基、吡喃酮基(pyronyl group)、噻吩基、喹啉基、异喹啉基、苯并呋喃基、苯并噻吩基、吲哚基、咔唑基、苯并噁唑基、苯并噻唑基、喹喔啉基、苯并咪唑基、吡唑基、二苯并呋喃基、二苯并噻吩基、萘啶基、菲咯啉基(phenanthrolinyl group)和吖啶基。
在通式(1)中由Ar表示的取代的芳族烃基、取代的芳族杂环基或取代的稠合多环芳基中的“取代基”具体包括基团如氟原子、氯原子、氰基、羟基、硝基、烷基、环烷基、烷氧基、氨基、苯基、萘基、蒽基、苯乙烯基、吡啶基、吡啶并吲哚基、喹啉基和苯并噻唑基。这些取代基可以进一步被取代。
在通式(1)中由R1至R14表示的取代或未取代的芳族烃基、取代或未取代的芳族杂环基或者取代或未取代的稠合多环芳基中的“芳族烃基”、“芳族杂环基”或“稠合多环芳基”的具体实例包括:苯基、联苯基、三联苯基、四联苯基、苯乙烯基、萘基、 蒽基、苊基、芴基、菲基、茚基、芘基、吡啶基、嘧啶基、呋喃基、吡喃酮基、噻吩基、喹啉基、异喹啉基、苯并呋喃基、苯并噻吩基、吲哚基、咔唑基、苯并噁唑基、苯并噻唑基、喹喔啉基、苯并咪唑基、吡唑基、二苯并呋喃基、二苯并噻吩基、萘啶基、菲咯啉基和吖啶基。
在通式(1)中由R1至R14表示的取代的芳族烃基、取代的芳族杂环基或取代的稠合多环芳基中的“取代基”具体包括氟原子、氯原子、三氟甲基、具有1至6个碳原子的线性或支化烷基、苯基、联苯基、三联苯基、四联苯基、苯乙烯基、萘基、芴基、菲基、茚基和芘基。这些取代基可以进一步被取代。
本发明的由通式(1)表示的具有通过亚苯基连接的取代的吡啶基和吡啶并吲哚环结构的化合物是新型化合物,与常规电子输送材料比较,所述化合物提供了高电子迁移率,具有优异的空穴阻挡能力并且薄膜状态稳定。
能够将本发明的由通式(1)表示的具有通过亚苯基连接的取代的吡啶基和吡啶并吲哚环结构的化合物用作用于有机EL器件的电子输送层的组成材料。与常规材料相比显示出较高电子注入/迁移率的材料的使用,提供了改进从电子输送层到发光层的电子输送效率以提高发光效率以及降低驱动电压以提高有机EL器件的耐久性的效果。
还能够将本发明的由通式(1)表示的具有通过亚苯基连接的取代的吡啶基和吡啶并吲哚环结构的化合物用作用于有机EL器件的空穴阻挡层的组成材料。与常规材料相比空穴阻挡能力优异和电子输送性也优异并且具有高的薄膜状态稳定性的材料的使用,提供了降低驱动电压、改进电流电阻(current resistance)并且提高有机EL器件的最大发光亮度的效果,同时显示高发光效率。
还能够将本发明的由通式(1)表示的具有通过亚苯基连接的取代的吡啶基和吡啶并吲哚环结构的化合物用作用于有机EL器件的发光层的组成材料。下述发光层的使用提供了使有机EL器件实现显示降低的驱动电压和具有改进的发光效率的效果,所述发光层通过使用与常规材料相比电子输送性优异并且具有宽带隙的本发明的材料作为发光层用的基质材料,并且使称作掺杂剂的荧光材料或磷光材料承载其上来制备。
本发明的有机EL器件是通过使用具有通过亚苯基连接的取代的吡啶基和吡啶并吲哚环结构的化合物制备的,与常规电子输送材料相比该化合物示出高电子迁移率、具有优异的空穴阻挡能力并且薄膜状态稳定。因此,变得可以实现高效率和高耐久性。
发明的效果
本发明的具有通过亚苯基连接的取代的吡啶基和吡啶并吲哚环结构的化合物用作有机EL器件的电子输送层、空穴阻挡层或发光层的组成材料,并且该化合物具有优异的空穴阻挡能力、薄膜状态稳定并且具有优异的耐热性。本发明的有机EL器件具有高发光效率,从而能够降低器件的实际驱动电压。通过降低发光开始电压,能够改进耐久性。
附图说明
图1是本发明实施例1的化合物(化合物99)的1H-NMR图。
图2是本发明实施例2的化合物(化合物126)的1H-NMR图。
图3是示出实施例5至7的EL器件的构造的图。
图4是示出比较例1和2的EL器件的构造的图。
附图标记说明
1:玻璃基板
2:透明阳极
3:空穴注入层
4:空穴输送层
5:发光层
6:空穴阻挡层
7:电子输送层
8:电子注入层
9:阴极
具体实施方式
本发明的具有通过亚苯基连接的取代的吡啶基和吡啶并吲哚环结构的化合物是新型化合物,并且该化合物可以通过例如以下方法合成。可以通过首先由钯催化剂将相应的卤代苯胺基吡啶进行环化反应从而合成吡啶并吲哚环(参见例如非专利文献5),接着将该吡啶并吲哚环与各种卤代亚苯基缩合来合成卤代亚苯基吡啶并吲哚环结构。此外,可以通过借助钯催化剂将相应的卤代亚苯基吡啶并吲哚环结构进行硼酸酯化反应来合成硼酸酯。此外,可以通过用锡试剂将相应的二卤代联吡啶进行缩合反应从而合成二卤代联吡啶基(参见例如非专利文献6),接着将该二卤代联吡啶基与硼酸酯缩合来合成具有通过亚苯基连接的取代的吡啶基和吡啶并吲哚环结构的化合物。
非专利文献5:J.Chem.Soc,Perkin Trans.1,p.1505(1999)
非专利文献6:J.Org.Chem.,67,p.443(2002)
在由通式(1)表示的具有通过亚苯基连接的取代的吡啶基和吡啶并吲哚环结构的化合物中,优选的化合物的具体实例示于以下,但是本发明不限于这些化合物。
[化学式2]
(化合物2)
[化学式3]
[化学式4]
[化学式5]
[化学式6]
[化学式7]
(化合物7)
[化学式8]
[化学式9]
[化学式10]
[化学式11]
[化学式12]
[化学式13]
[化学式14]
[化学式15]
[化学式16]
[化学式17]
[化学式18]
(化合物18)
[化学式19]
[化学式20]
(化合物20)
[化学式21]
[化学式22]
(化合物22)
[化学式23]
[化学式24]
[化学式25]
(化合物25)
[化学式26]
[化学式27]
[化学式28]
[化学式29]
[化学式30]
[化学式31]
[化学式32]
[化学式33]
[化学式34]
[化学式35]
[化学式36]
[化学式37]
(化合物37)
[化学式38]
[化学式39]
[化学式40]
[化学式41]
[化学式42]
[化学式43]
[化学式44]
[化学式45]
[化学式46]
[化学式47]
[化学式48]
[化学式49]
[化学式50]
[化学式51]
[化学式52]
[化学式53]
[化学式54]
(化合物54)
[化学式55]
[化学式56]
[化学式57]
[化学式58]
[化学式59]
[化学式60]
[化学式61]
[化学式62]
[化学式63]
[化学式64]
[化学式65]
[化学式66]
[化学式67]
[化学式68]
(化合物68)
[化学式69]
[化学式71] (化合物71)
[化学式74]
[化学式75]
[化学式76]
[化学式77]
[化学式78]
[化学式79]
[化学式80]
[化学式81]
[化学式82]
[化学式83]
[化学式84]
(化合物84)
[化学式85]
[化学式86]
(化合物86)
[化学式87]
[化学式88]
[化学式89]
(化合物89)
[化学式90]
[化学式91]
[化学式92]
[化学式93]
[化学式94]
[化学式95]
[化学式96]
[化学式97]
[化学式98]
[化学式99]
[化学式100]
[化学式101]
(化合物101)
[化学式102]
[化学式103]
(化合物103)
[化学式104]
[化学式105]
[化学式106]
[化学式107]
[化学式108]
[化学式109]
[化学式110]
[化学式111]
[化学式112]
(化合物112)
[化学式113]
(化合物113)
[化学式114]
[化学式115]
[化学式116]
[化学式117]
[化学式118]
[化学式119]
[化学式120]
[化学式121]
[化学式122]
[化学式123]
[化学式124]
[化学式125]
[化学式126]
[化学式127]
[化学式128]
这些化合物的纯化通过以下进行:通过柱色谱法的纯化,使用活性炭或活性粘土等的吸附纯化或者使用溶剂的重结晶或结晶法等。化合物的鉴定通过NMR分析进行。作为物理性能,进行DSC测量(Tg)和熔点测量。熔点作为气相沉积性的指标和 玻璃化转变温度(Tg)作为薄膜状态稳定性的指标。
熔点和玻璃化转变温度借助由Bruker AXS制造的高灵敏差示扫描量热仪DSC 3100S使用粉末材料来测量。
此外,功函数通过在ITO基板上制备100nm的薄膜和在空气中使用光电子能谱仪(型号AC-3,由Riken Keiki Co.,Ltd.制造)来测量。将功函数作为空穴阻挡能力的指标。
本发明的有机EL器件的结构的实例包括在基板上依次具有阳极、空穴注入层、空穴输送层、发光层、空穴阻挡层、电子输送层和阴极的结构,和进一步具有在电子输送层和阴极之间的电子注入层的结构。在这些多层结构中,可以省略几层有机层并且,例如,所述结构可以具有在基板上依次具有阳极、空穴输送层、发光层、电子输送层和阴极的构造。
作为有机EL器件的阳极,使用具有大的功函数的电极材料如ITO或金。作为空穴注入层,除了铜酞菁(下文中称作CuPc)以外,可以使用材料如星形放射型(star-burst type)三苯胺衍生物和湿法型材料。
对于空穴输送层,可以使用N,N′-二苯基-N,N′-二(间-甲苯基)-联苯胺(下文中称作TPD)和N,N′-二苯基-N,N′-二(α-萘基)-联苯胺(下文中称作NPD),它们是联苯胺衍生物和各种三苯胺四聚体等之一。此外,作为空穴注入/输送层,可以使用湿法型聚合物材料如PEDOT/PSS。
作为本发明的有机EL器件的发光层、空穴阻挡层和电子输送层,除了具有通过亚苯基连接的取代的吡啶基和吡啶并吲哚环结构的化合物以外,可以使用铝配合物、噻唑衍生物和噁唑衍生物、咔唑衍生物和聚二烷基芴(polydialkylfluorene)衍生物等。
通过使用用于发光层的常规发光材料如铝配合物或苯乙烯 基衍生物和使用具有通过亚苯基连接的取代的吡啶基和吡啶并吲哚环结构的化合物作为空穴阻挡层和电子输送层,可以制备高性能有机EL器件。此外,高性能有机EL器件也可以通过对发光层的基质材料添加掺杂剂例如荧光材料如喹吖啶酮、香豆素或红荧烯,或者磷光材料如苯基吡啶的铱配合物来制备。
此外,通过与常规电子输送材料形成多层或共沉积可以将具有通过亚苯基连接的取代的吡啶基和吡啶并吲哚环结构的化合物用作电子输送层。
本发明的有机EL器件可以具有电子注入层。作为电子注入层,可以使用氟化锂等。对于阴极,将具有低功函数的电极材料如铝或具有低功函数的合金如铝镁用作电极材料。
参考以下实施例,将更详细地描述本发明的实施方案,但本发明不应该解释为限于此,只要不超出本发明的要旨即可。
实施例1
(5,5′-双[3-(5H-吡啶并[4,3-b])吲哚-5-基]苯基]-[2,2′]联吡啶(化合物99)的合成)
将6.0g 2,5-二溴吡啶、7.0ml双三丁基锡和120ml二甲苯装入反应容器,接着在60℃下加热和搅拌15分钟。此外,向其中添加700mg四(三苯基膦)钯,接着在120℃下搅拌8小时。冷却至室温后,通过过滤移除不溶性物质,将滤液用150ml乙二胺四乙酸酯水溶液洗涤。将有机层用无水硫酸钠脱水并且在减压下浓缩以获得粗产品。将粗产品通过柱色谱(载体:硅胶,洗脱液:环己烷/甲苯)纯化以获得1.7g(产率42%)黄色粉末形式的5,5′-二溴-[2,2′]联吡啶。
将17.2ml 1,3-二溴苯、6.0g 5H-吡啶并[4,3-b])吲哚、1.1g铜粉末、9.9g碳酸钾和0.6ml二甲亚砜装入另一个反应容器,接着在180℃下加热和搅拌4小时。冷却至室温后,向其中添加50ml 氯仿,通过过滤移除不溶性物质,将滤液在减压下浓缩以获得粗产品。将粗产品通过柱色谱(载体:硅胶,洗脱液:己烷/氯仿)纯化以获得7.1g(产率62%)白色粉末形式的5-(3-溴苯基)-5H-吡啶并[4,3-b]吲哚。
向7.1g所得的5-(3-溴苯基)-5H-吡啶并[4,3-b]吲哚添加6.7g联硼酸频那醇酯(bis(pinacolato)diboron)、6.7g乙酸钾、540mg双(二苯基膦二茂铁)二钯和100ml二甲亚砜,接着在80℃下加热和搅拌5小时。冷却至室温后,向其中添加200ml乙酸乙酯和100ml水以分离液体,并且进一步将水性层用100ml乙酸乙酯萃取。合并有机层、用无水硫酸镁脱水并且接着在减压下浓缩以获得粗产品。将粗产品通过柱色谱(载体:NH硅胶,洗脱液:氯仿)纯化以获得4.4g(产率53%)黄色粉末形式的5-[3-(4,4,5,5-四甲基-[1,3,2]二氧硼戊环-2-基)苯基]-5H-吡啶并[4,3-b]吲哚。
向2.8g所得的5-[3-(4,4,5,5-四甲基-[1,3,2]二氧硼戊环-2-基)苯基]-5H-吡啶并[4,3-b]吲哚添加1.2g已经预先合成的5,5′-二溴[2,2′]联吡啶、440mg四(三苯基膦)钯、9.4ml 2M碳酸钾水溶液、32ml甲苯和8ml乙醇,接着在回流下加热同时搅拌8小时。冷却至室温后,通过过滤分离沉淀物。将沉淀物溶解在氯仿/甲醇的混合溶剂中,通过过滤移除不溶性物质,将滤液在减压下浓缩以获得粗产品。将粗产品通过柱色谱(载体:NH硅胶,洗脱液:氯仿)纯化以获得1.7g(产率71%)淡黄色粉末形式的5,5′-双[3-(5H-吡啶并[4,3-b])吲哚-5-基]苯基]-[2,2′]联吡啶(化合物99)。
使用NMR来鉴定所得的淡黄色粉末的结构。1H-NMR测量的结果示于图1。
在1H-NMR(CDCl3)上检测到如下28个氢信号。δ(ppm)=9.42(2H),9.01(2H),8.57(4H),8.25(2H),8.11(2H),7.78-7.86(6H),7.63(2H),7.52(4H),7.42(2H),7.38(2H)。
实施例2
(2,6-双[4-(5H-吡啶并[4,3-b])吲哚-5-基]苯基]吡啶(化合物126)的合成)
与实施例1中相同,由1,4-二溴苯和5H-吡啶并[4,3-b])吲哚合成5-(4-溴苯基)-5H-吡啶并[4,3-b]吲哚,并且进一步与联硼酸频那醇酯进行反应以合成5-[4-(4,4,5,5-四甲基-[1,3,2]二氧硼戊环-2-基)苯基]-5H-吡啶并[4,3-b]吲哚。向5.0g所得的5-[4-(4,4,5,5-四甲基-[1,3,2]二氧硼戊环-2-基)苯基]-5H-吡啶并[4,3-b]吲哚中添加1.6g 2,6-二溴吡啶、0.39g四(三苯基膦)钯、16.9ml 2M碳酸钾水溶液、56ml甲苯和14ml乙醇,接着在回流下加热同时搅拌8.5小时。冷却至室温后,向其中添加50ml甲苯和100ml水以分离液体并且收集有机层。接着,将水性层用70ml甲苯萃取。合并有机层、用无水硫酸镁脱水并且接着在减压下浓缩以获得粗产品。将粗产品通过柱色谱(载体:NH硅胶,洗脱液:甲苯)纯化以获得2.3g(产率60%)白色粉末形式的2,6-双[4-(5H-吡啶并[4,3-b])吲哚-5-基]苯基]吡啶(化合物126)。
使用NMR鉴定所得的白色粉末的结构。1H-NMR测量的结果示于图2。
在1H-NMR(CDCl3)上检测到如下25个氢信号。δ(ppm)=9.40(2H),8.55(2H),8.43(4H),8.22(2H),7.95(1H),7.84(2H),7.69(4H),7.46-7.54(4H),7.34-7.41(4H)。
实施例3
对于本发明的化合物,借助高灵敏差示扫描量热仪(D SC3100S,由Bruker AXS制造)测定熔点和玻璃化转变温度。
熔点 玻璃化转变温度
发明实施例1的化合物 352℃ 138℃
发明实施例2的化合物 283℃ 134℃
本发明的化合物示出100℃以上的玻璃化转变温度,因此其薄膜状态稳定。
实施例4
使用本发明的各化合物,在ITO基板上制备膜厚度为100nm的沉积膜,并且在空气中在光电子能谱仪(型号AC-3,由Riken Keiki Co.,Ltd.制造)上测量功函数。
功函数
发明实施例1的化合物 6.28eV
发明实施例2的化合物 6.28eV
因此,本发明的化合物比常规空穴输送材料如NPD和TPD所具有的5.4eV的功函数具有更深的值并且具有大的空穴阻挡能力。
实施例5
如图3中所示,有机EL器件具有在玻璃基板1上依次由空穴注入层3、空穴输送层4、发光层5、空穴阻挡层6、电子输送层7、电子注入层8和阴极(铝电极)9构成的层状结构,在所述玻璃基板1上已经预先形成ITO电极作为透明电极2。
具体地,将在其上已经形成膜厚度为150nm ITO的玻璃基板1用有机溶剂洗涤后,将所述玻璃基板1表面通过UV臭氧处理清洗。将其固定于真空沉积机内,接着将该真空沉积机抽空至0.001Pa以下。接着,以3.6nm/分钟的沉积速率将铜酞菁在其上形成至约20nm的厚度作为空穴注入层3。以3.6nm/分钟的沉积速率将NPD在空穴注入层3上形成至约40nm的厚度作为空穴输送层4。作为发光层5,以3.6nm/分钟的沉积速率将Alq3在空穴输送层4上形成至约30nm的厚度。在发光层5上,以3.6nm/分钟的沉积速率将发明实施例1的化合物(化合物99)形成至约30nm的厚度作为空穴阻挡层6兼电子输送层7。在空穴阻挡层兼电子输 送层6和7上,以3.6nm/分钟的沉积速率将氟化锂形成至约0.5nm的厚度作为电子注入层8。最后,沉积铝至约200nm的厚度以形成阴极9。将由此制备的器件贮存于真空干燥器中,并且在常温下的气氛中测量特性。
当电流以20mA/cm2的电流密度流向通过使用发明实施例1的化合物(化合物99)制备的有机EL器件时,发光性的测量结果归纳于表1中。
[比较例1]
为了比较,除了在实施例5中的空穴阻挡层6兼电子输送层7的材料用Alq3代替作为电子输送层7以外,在与实施例5相同的条件下制备有机EL器件。当电流以20mA/cm2的电流密度流向该制备的有机EL器件时,测量发光性的结果归纳于表1中。
[表1]
此外,与Alq3的发光开始电压4.0V相比,实施例5的发光开始电压低至3.8V。
因此,本发明的有机EL器件具有优异的发光效率并且与使用Alq3作为常规电子输送材料的器件相比还实现了实际驱动电压的显著降低。由此,还可以发现发光开始电压也得到降低。
实施例6
以与实施例5相同的方式,将在其上已经形成膜厚度为150nm的ITO的玻璃基板1用有机溶剂洗涤后,将其表面通过氧等离子体处理清洗。将所述玻璃基板1固定于真空沉积机中,接着将该真空沉积机抽空至0.001Pa以下。其后,以6.0nm/分钟的 气相沉积速率将如下所示的化合物129在该玻璃基板1上形成至约20nm的厚度作为空穴注入层3以覆盖透明阳极2。在空穴注入层3上,以6.0nm/分钟的气相沉积速率将如下所示的化合物130形成至约40nm的厚度作为空穴输送层4。在空穴输送层4上,通过以使得化合物131∶化合物132的气相沉积速率比为5∶95(化合物131为0.48nm/分钟和化合物132为9.12nm/分钟)的气相沉积速率双重气相沉积(dual vapor deposition),将如下所示的化合物131和如下所示的化合物132形成至约30nm的厚度作为发光层5。在发光层5上,以6.0nm/分钟的气相沉积速率将本发明实施例1的化合物(化合物99)形成至约30nm的厚度作为空穴阻挡层6兼电子输送层7。在空穴阻挡层兼电子输送层6和7上,以0.6nm/分钟的气相沉积速率将氟化锂形成至约0.5nm的厚度作为电子注入层8。最后,气相沉积铝至约150nm的厚度以形成阴极9。将制备的器件在周围温度的气氛中通过施加直流电压进行特性测量。
当电流以10mA/cm2的电流密度流过使用发明实施例1的化合物(化合物99)制备的有机EL器件时,发光性的测量结果归纳于表2中。
[化学式129]
[化学式130]
[化学式131]
[化学式132]
实施例7
除了将本发明实施例2的化合物(化合物126)用作空穴阻挡层6兼电子输送层7以外,以与实施例6相同的方式制备有机EL器件。当电流以10mA/cm2的电流密度流过该制备的有机EL器件时,发光性的测量结果归纳于表2中。
[比较例2]
为了比较,除了将实施例6中所用的空穴阻挡层6兼电子输送层7的材料用Alq3代替作为电子输送层7以外,在与实施例6相同的条件下制备有机EL器件,并且研究了其特性。测量结果归纳于表2中。
[表2]
如表2中所示,当电流以10mA/cm2的电流密度流过时,与Alq3的驱动电压为5.80V相比,发明实施例1和实施例2的化合物(化合物99和化合物126)的驱动电压都低(化合物99:5.00V,化合物126:4.25V)。此外,当电流以10mA/cm2的电流密度流过时,亮度、发光效率和电力效率均得到极大地改进。
因此,可以发现本发明的有机EL器件具有优异的发光效率和电力效率,并且与使用Alq3作为一般性电子输送材料的器件相比还实现了实际驱动电压的显著降低。
已经参考具体实施方案详细地描述了本发明,对于本领域熟练人员显而易见的是在不偏离其精神和范围的情况下可以做出各种改变和改进。
本申请是基于2008年1月31日提交的日本专利申请2008-020110,在此将其内容引入以作参考。
产业上的可利用性
由于根据本发明的具有通过亚苯基连接的取代的吡啶基和吡啶并吲哚环结构的化合物显示良好的电子注入性和优异的空穴阻挡能力,并且薄膜状态稳定,所述化合物作为用于有机EL器件的化合物是优异的。通过使用该化合物制备有机EL器件, 可以降低驱动电压并且能够改进耐久性。例如,可以将该化合物扩展至家用电器和照明的应用。
Claims (6)
1.一种具有通过亚苯基连接的取代的吡啶基和吡啶并吲哚环结构的化合物,该化合物由以下通式(1)表示:
其中Ar表示取代或未取代的芳族烃基、取代或未取代的芳族杂环基或者取代或未取代的稠合多环芳基;R1至R14可以彼此相同或不同,并且各自表示氢原子、氟原子、氯原子、氰基、三氟甲基、或者具有1至6个碳原子的线性或支化烷基;n表示2;W、X、Y和Z分别表示碳原子或氮原子,条件是W、X、Y和Z中仅之一表示氮原子时,所述氮原子不具有取代基R7、R8、R9或R10,
其中,Ar表示的取代或未取代的芳族烃基、取代或未取代的芳族杂环基或者取代或未取代的稠合多环芳基中的芳族烃基、芳族杂环基或稠合多环芳基为:苯基、联苯基、萘基、蒽基、芴基、菲基或芘基,
由Ar表示的取代的芳族烃基、取代的芳族杂环基或取代的稠合多环芳基中的取代基为氟原子、氯原子、氰基、吡啶基、吡啶并吲哚基或喹啉基。
2.一种有机电致发光器件,该有机电致发光器件包括一对电极和插置于所述电极之间的至少一层有机层,其中所述至少一层有机层包含根据权利要求1所述的化合物。
3.根据权利要求2所述的有机电致发光器件,其中所述至少一层有机层包括电子输送层,并且所述电子输送层包含由所述通式(1)表示的化合物。
4.根据权利要求2所述的有机电致发光器件,其中所述至少一层有机层包括空穴阻挡层,并且所述空穴阻挡层包含由所述通式(1)表示的化合物。
5.根据权利要求2所述的有机电致发光器件,其中所述至少一层有机层包括发光层,并且所述发光层包含由所述通式(1)表示的化合物。
6.根据权利要求2所述的有机电致发光器件,其中所述至少一层有机层包括电子注入层,并且所述电子注入层包含由所述通式(1)表示的化合物。
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US8927119B2 (en) | 2009-08-05 | 2015-01-06 | Hodogaya Chemical Co., Ltd. | Compound having substituted anthracene ring structure and pyridoindole ring structure, and organic electroluminescent device |
US9196839B2 (en) * | 2010-01-26 | 2015-11-24 | Hodogaya Chemical Co., Ltd. | Compound having triphenylamine structure, and organic electroluminescent device |
JP4958995B2 (ja) | 2010-08-27 | 2012-06-20 | キヤノン株式会社 | 電子写真感光体、プロセスカートリッジ及び電子写真装置 |
WO2012037269A1 (en) | 2010-09-16 | 2012-03-22 | Nitto Denko Corporation | Substituted bipyridines for use in organic light-emitting devices |
US9324950B2 (en) | 2010-11-22 | 2016-04-26 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device |
US8883323B2 (en) | 2010-11-22 | 2014-11-11 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device |
CN103328475A (zh) | 2011-01-18 | 2013-09-25 | 保土谷化学工业株式会社 | 具有被取代的联吡啶基和吡啶并吲哚环结构的化合物以及有机电致发光器件 |
US8585926B2 (en) | 2011-03-03 | 2013-11-19 | Nitto Denko Corporation | Substituted bipyridines for use in light-emitting devices |
TWI469986B (zh) * | 2013-06-20 | 2015-01-21 | Nat Univ Tsing Hua | 應用於高效率染料敏化太陽能電池的新型釕金屬錯合物 |
US9328094B2 (en) | 2011-09-19 | 2016-05-03 | Nitto Denko Corporation | Substituted biaryl compounds for light-emitting devices |
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JP2006120906A (ja) | 2004-10-22 | 2006-05-11 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
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JP5200320B2 (ja) * | 2005-09-14 | 2013-06-05 | コニカミノルタホールディングス株式会社 | 非水分散液、有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の製造方法、表示装置及び照明装置 |
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KR101030021B1 (ko) * | 2007-04-13 | 2011-04-20 | 제일모직주식회사 | 분자 내에 정공 수송기와 전자 수송기를 동시에 가지는바이폴라 특성의 유기화합물을 포함하는 유기광전소자용재료 및 이를 이용한 유기광전소자 |
JP5832746B2 (ja) * | 2008-09-24 | 2015-12-16 | 保土谷化学工業株式会社 | 置換されたアントラセン環構造とピリドインドール環構造を有する化合物および有機エレクトロルミネッセンス素子 |
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Publication number | Publication date |
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TWI464167B (zh) | 2014-12-11 |
TW200938543A (en) | 2009-09-16 |
KR20100110851A (ko) | 2010-10-13 |
KR101567112B1 (ko) | 2015-11-06 |
EP2241568A4 (en) | 2011-11-16 |
US20110006291A1 (en) | 2011-01-13 |
CN101932581A (zh) | 2010-12-29 |
EP2463288A1 (en) | 2012-06-13 |
EP2241568A1 (en) | 2010-10-20 |
JPWO2009096549A1 (ja) | 2011-05-26 |
EP2241568B1 (en) | 2014-09-10 |
EP2463288B1 (en) | 2014-09-10 |
US8377573B2 (en) | 2013-02-19 |
WO2009096549A1 (ja) | 2009-08-06 |
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