CN110845421A - 一种电子传输化合物、其合成方法及有机电致发光器件 - Google Patents

一种电子传输化合物、其合成方法及有机电致发光器件 Download PDF

Info

Publication number
CN110845421A
CN110845421A CN201911192497.0A CN201911192497A CN110845421A CN 110845421 A CN110845421 A CN 110845421A CN 201911192497 A CN201911192497 A CN 201911192497A CN 110845421 A CN110845421 A CN 110845421A
Authority
CN
China
Prior art keywords
electron transport
substituted
transport compound
unsubstituted
organic electroluminescent
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN201911192497.0A
Other languages
English (en)
Inventor
马晓宇
汪康
王铁
姚明明
邱镇
陈振生
刘昌�
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Jilin Optical and Electronic Materials Co Ltd
Original Assignee
Jilin Optical and Electronic Materials Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Jilin Optical and Electronic Materials Co Ltd filed Critical Jilin Optical and Electronic Materials Co Ltd
Priority to CN201911192497.0A priority Critical patent/CN110845421A/zh
Publication of CN110845421A publication Critical patent/CN110845421A/zh
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • 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
    • 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
    • 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
    • H10K50/16—Electron transporting layers
    • 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
    • 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
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • 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
    • 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
    • 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
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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
    • C09K2211/1011—Condensed systems
    • 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
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • 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
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • 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
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
    • 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
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • 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
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • 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
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

本发明公开了一种电子传输化合物、其合成方法及有机电致发光器件，属于化学合成及光电材料领域。该电子传输化合物的结构通式为：
Figure DDA0002293919700000011
或
Figure DDA0002293919700000012
式中，R1、R2分别独立地为氢、氘原子、卤素、氰基、硝基、羟基、氨基、取代或非取代的C1～C60的烷基、C3～C60的环烷基、C1～C60的杂环基、C1～C60烷氧基、C1～C60的烷胺基、C3～C60烯烷基、C3～C60炔烷基、C6～C60芳基、C6～C60的杂芳基、C10～C60的稠环基、C10～C60的螺环基中的一种；R3独立地为氢、取代或非取代的C1～C30烷基、取代或非取代的C6～C30芳基、取代或非取代的C3～C30杂环基中的一种。将该电子传输化合物作为有机电致发光器件的发光层或电子传输层的材料，可以显著地降低有机电致发光器件的驱动电压以及提高有机电致发光器件的发光效率和使用寿命。

Description

一种电子传输化合物、其合成方法及有机电致发光器件
技术领域
本发明涉及化学合成及光电材料领域，具体是一种电子传输化合物、其合成方法及有机电致发光器件。
背景技术
有机电致发光是指有机材料在电场作用下，将电能直接转化为光能的一种发光现象，其已经逐步应用在智能手机、平板电视、虚拟现实商品中。
目前，有机电致发光器件的效率以及寿命等因素制约了其发展，为了提高有机电致发光器件的亮度、效率和寿命，通常在器件中使用多层结构。这些多层结构通常包括：空穴注入层，空穴传输层，电子阻挡层，发光层和电子传输层，电子注入层等等。
在有机材料中，电子和空穴的转移速度是不同的，若使用适合的材料，将电子和空穴有效的转移到发光层，平衡电子和空穴的数量，可有效的提高发光效率。然而适合的材料十分难于寻找。其中，三(8-羟基喹啉)铝(Alq3)作为电子传输材料自发明以来使用了将近30年，而且有较多的资料证明其比常规材料优异。但其作为电子传输材料，还是存在发光效率较低和使用寿命较短等问题。
发明内容
本发明实施例的目的在于提供一种电子传输化合物，以解决上述背景技术中提出的问题。
为实现上述目的，本发明实施例提供如下技术方案：
一种电子传输化合物，所述电子传输化合物的结构通式为式I或式II：
Figure BDA0002293919690000021
式中，R1、R2分别独立地为氢、氘原子、卤素、氰基、硝基、羟基、氨基、取代或非取代的C1～C60的烷基、C3～C60的环烷基、C1～C60的杂环基、C1～C60烷氧基、C1～C60的烷胺基、C3～C60烯烷基、C3～C60炔烷基、C6～C60芳基、C6～C60的杂芳基、C10～C60的稠环基、C10～C60的螺环基中的一种；
R3独立地为氢、取代或非取代的C1～C30烷基、取代或非取代的C6～C30芳基、取代或非取代的C3～C30杂环基中的一种；
X1、X2、X3、X4、X5、X6、X7、X8分别独立地为H或N；
环A、环B分别独立地为氢、取代或非取代的C6～C60芳基、取代或非取代的C6～C60的杂芳基、取代或非取代的C10～C60的稠环基、C10～C60的螺环基中的一种。
其中，术语“取代或非取代的”意指被选自以下的一个、两个或更多个取代基取代：氘；卤素基团；腈基；羟基；羰基；酯基；甲硅烷基；硼基；经取代或未经取代的烷基；经取代或未经取代的环烷基；经取代或未经取代的烷氧基；经取代或未经取代的烯基；经取代或未经取代的烷基胺基；经取代或未经取代的杂环基胺基；经取代或未经取代的芳基胺基；经取代或未经取代的芳基；经取代或未经取代的杂环基；或者被以上所示的取代基中的两个或更多个取代基相连接的取代基取代，或者不具有取代基。例如，“两个或更多个取代基相连接的取代基”可以包括联苯基。换言之，联苯基可以为芳基，或者可以解释为两个苯基相连接的取代基。
作为本发明实施例的一个优选方案，所述的杂环基为包含有至少一个杂原子的芳香族或非芳香族环状基团。
作为本发明实施例的另一个优选方案，所述的杂原子为O、S、N、P、B、Si和Se中的一种。
作为本发明实施例的另一个优选方案，所述的杂原子为O、S和N中的一种。
作为本发明实施例的另一个优选方案，所述的杂环基为吗啉基、哌啶基、吡咯烷基、四氢呋喃、四氢吡喃和四氢噻吩中的一种。
作为本发明实施例的另一个优选方案，所述电子传输化合物的化学结构式为式1～式69中的一种：
Figure BDA0002293919690000031
Figure BDA0002293919690000041
Figure BDA0002293919690000051
Figure BDA0002293919690000061
Figure BDA0002293919690000071
本发明实施例的另一目的在于提供一种上述的电子传输化合物的合成方法，其包括以下步骤：
Figure BDA0002293919690000081
将通式为式III的第一反应物和N-溴代丁二酰亚胺置于N,N-二甲基甲酰胺中进行搅拌反应后，得到中间体；
在保护气氛下，将上述中间体、通式为式IV或式V的第二反应物、四(三苯基膦)钯和碳酸钾加入到混合溶剂中进行升温回流反应，并经洗涤、过滤后，再置于有机溶剂中进行重结晶处理，得到所述的电子传输化合物。
其中，中间体的合成路线如下：
Figure BDA0002293919690000082
通式为式I的电子传输化合物的化学合成路线如下：
通式为式II的电子传输化合物的化学合成路线如下：
Figure BDA0002293919690000091
上述合成路线中出现的R1～R3、X1～X8、环A、环B与上述式I和式II中所述的范围相同。
作为本发明实施例的另一个优选方案，所述的步骤中，混合溶剂包括甲苯、乙醇和水。
优选的，甲苯、乙醇和水的体积比为(2～4):(0.8～1.2):1。
优选的，第一反应物与N-溴代丁二酰亚胺的摩尔比为(8～12):1。
优选的，中间体、第二反应物、四(三苯基膦)钯和碳酸钾的摩尔比为1:(0.8～1.2):(0.01～0.03):(2～4)。
作为本发明实施例的另一个优选方案，所述的步骤中，重结晶处理所使用的有机溶剂为1,4-二氧六环。
本发明实施例的另一目的在于提供一种有机电致发光器件，其包括至少一组有机物层，所述的有机物层中包括发光层和/或电子传输层；所述的发光层和电子传输层分别包含上述的电子传输化合物。
与现有技术相比，本发明实施例的有益效果是：
本发明实施例提供了一种新的电子传输化合物，将该电子传输化合物作为有机电致发光器件的发光层或电子传输层的材料，可以显著地降低有机电致发光器件的驱动电压以及提高有机电致发光器件的发光效率和使用寿命，从而可以提高有机电致发光器件的实用性。另外，本发明实施例提供的电子传输化合物的合成路线较短，工艺简单，原料易得，成本低，适合工业化生产。
具体实施方式
下面将结合本发明实施例，对本发明实施例中的技术方案进行清楚、完整地描述，显然，所描述的实施例仅仅是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例，都属于本发明保护的范围。
实施例1
该实施例提供了一种电子传输化合物，其化学结构式为发明内容中的式1，该电子传输化合物的合成方法的反应路线如下：
Figure BDA0002293919690000101
其具体的合成方法包括以下步骤：
(1)在室温条件下，将第一反应物1-A(34.4g，80.0mmol)加入到N,N-二甲基甲酰胺(200mL)溶剂中，同时添加N-溴代丁二酰亚胺(17.8g，100.0mmol)进行搅拌反应，得到反应液；反应结束后，将反应液浓缩至少许，并缓慢滴加到正在被搅拌的石油醚中，待固体析出完全后，再进行抽滤、烘干，得到中间体1-I(34.1g，收率为84％)。
(2)在氮气的保护气氛下，将上述中间体1-I(60.0mmol)、第二反应物1-B(60mmol)、碳酸钾(180.0mmol)加入到400mL体积比3:1:1的甲苯/乙醇/水的混合溶剂中，同时添加四(三苯基磷)钯(0.7mmol)，并升温至回流，进行反应；待反应结束后，再冷却至室温，并加入水进行洗涤、过滤、滤饼干燥后，再置于1,4-二氧六环中进行重结晶处理，得到的最终产物(34.8g，收率83％)即为式1所示的电子传输化合物。
按照与上述实施例1中步骤(1)相同原理和路线的合成方法，分别采用不同的第一反应物合成不同的中间体，其对应第一反应物和中间体的结构式、中间体的收率以及中间体分子量的质谱测试值如下表1所示。
表1
Figure BDA0002293919690000111
Figure BDA0002293919690000121
Figure BDA0002293919690000131
按照与上述实施例1中步骤(2)相同原理和路线的合成方法，分别采用上表1中的中间体与不同的第二反应物可以合成上述发明内容中的化学结构式为式4、7、10、14、17、22、27、33、40、45、55、60的电子传输化合物，其对应中间体、第二反应物和电子传输化合物的结构式、电子传输化合物的收率以及电子传输化合物分子量的质谱测试值如下表2所示。
表2
Figure BDA0002293919690000132
Figure BDA0002293919690000161
实施例2
该实施例提供了一种采用上述实施例提供的电子传输化合物制备得到的有机电致发光器件，其中，该有机电致发光器件包括第一电极、第二电极以及设置在所述第一电极与第二电极之间的至少一组有机物层。
另外，当有机物层包含空穴注入层、空穴传输层和同时具备空穴注入和空穴传输技能层时，优选所述空穴注入层、空穴传输层和同时具备空穴注入和空穴传输技能层中至少一层包含空穴注入物质、空穴传输物质或既具备空穴注入又具备空穴传输技能的物质。当有机物层为单层结构时，所述有机物层为发光层，当所述有机物层为多层结构时，所述有机物层包括发光层；所述发光层中优选包括磷光主体、荧光主体、磷光掺杂材料与荧光掺杂材料中的一种或多种。
当所述有机物层包括电子传输层时，所述电子传输层可包括上述实施例提供的电子传输化合物。
在本发明的一些具体实施例中，所述电子传输层还可包括金属化合物。所述金属化合物为本领域技术人员熟知的用于电子传输的物质即可，并无特殊的限制。
当所述有机物层同时包括发光层与电子传输层时，所述发光层与电子传输层可分别包括结构相同或不相同的上述实施例提供的电子传输化合物。
具体的，上述有机电致发光器件的制备方法包括以下步骤：
(1)将费希尔公司涂层厚度为的ITO玻璃基板放在蒸馏水中清洗2次，超声波洗涤30min，用蒸馏水反复清洗2次，超声波洗涤10min，蒸馏水清洗结束后，再用异丙醇、丙酮、甲醇等溶剂按顺序超声波洗涤以后干燥，转移到等离子体清洗机里，将上述基板洗涤5min，得到ITO透明电极，并送到蒸镀机里。
(2)将已经准备好的ITO透明电极上蒸镀厚度为80nm的4,4',4”-三[2-萘基苯基氨基]三苯基胺(2-TNATA)作为空穴注入层。在形成的空穴注入层上面真空蒸镀厚度为30nm的N'-二(1-萘基)-N,N'-二苯基-(1,1'-联苯)-4,4'-二胺(NPB)作为空穴传输层。
(3)在上述空穴传输层上蒸镀厚度为20nm的4,4'-N,N'-联苯二咔唑("CBP")以及掺杂有5％的二(1-苯基-异喹啉)(乙酰丙酮)合铱(Ⅲ)(Ir(ppy)2(acac))的发光材料。接着在上述发光层上真空蒸镀厚度为10nm的双(2-甲基-8-羟基喹啉-N1,08)-(1,1’-联苯-4-羟基)铝(BAlq)作为空穴阻挡层。然后，在上述空穴阻挡层上真空蒸镀厚度为40nm上述实施例制得的电子传输化合物，作为电子传输层。再接着，在上述电子传输层上真空蒸镀厚度为1nm氟化锂，作为电子注入层。最后，蒸镀厚度为100nm的铝作为阴极，便可完成有机电致发光器件的制备。
参照上述方法，分别选用化学结构式为式1、4、7、10、14、17、22、27、33、40、45、55、60的电子传输化合物，作为电子传输层，并制备得到相应的有机电致发光器件。
对比例1
该对比例提供了一种现有的有机电致发光器件，该有机电致发光器件的制备方法与实施例2提供的制备方法相同，唯一区别在于，该有机电致发光器件的电子传输层所采用的电子传输化合物为Alq3，其结构式为：
Figure BDA0002293919690000181
将上述实施例2和对比例1得到的有机电致发光器件分别加以正向直流偏置电压，利用Photo Research公司的PR-650光度测量设备测定有机电致发光特性，并在5000cd/m2的基准灰度下利用McScience公司的寿命测定装置测定其T95的寿命，其测试得到的驱动电压、发光效率以及T95寿命如下表3所示。
表3
Figure BDA0002293919690000182
Figure BDA0002293919690000191
从上表3可以看出，使用本发明实施例提供的电子传输化合物作为电子传输层所制到的有机电致发光器件，与使用现有电子传输化合物Alq3作为电子传输层所制到的有机电致发光器件相比，其驱动电压明显降低，且发光效率以及寿命得到了显著的提高。
以上述依据本发明的理想实施例为启示，通过上述的说明内容，相关工作人员完全可以在不偏离本项发明技术思想的范围内，进行多样的变更以及修改。本项发明的技术性范围并不局限于说明书上的内容，必须要根据权利要求范围来确定其技术性范围。

Claims (10)

1.一种电子传输化合物，其特征在于，所述电子传输化合物的结构通式为式I或式II：
Figure FDA0002293919680000011
式中，R1、R2分别独立地为氢、氘原子、卤素、氰基、硝基、羟基、氨基、取代或非取代的C1～C60的烷基、C3～C60的环烷基、C1～C60的杂环基、C1～C60烷氧基、C1～C60的烷胺基、C3～C60烯烷基、C3～C60炔烷基、C6～C60芳基、C6～C60的杂芳基、C10～C60的稠环基、C10～C60的螺环基中的一种；
R3独立地为氢、取代或非取代的C1～C30烷基、取代或非取代的C6～C30芳基、取代或非取代的C3～C30杂环基中的一种；
X1、X2、X3、X4、X5、X6、X7、X8分别独立地为H或N；
环A、环B分别独立地为氢、取代或非取代的C6～C60芳基、取代或非取代的C6～C60的杂芳基、取代或非取代的C10～C60的稠环基、C10～C60的螺环基中的一种。
2.根据权利要求1所述的一种电子传输化合物，其特征在于，所述的杂环基为包含有至少一个杂原子的芳香族或非芳香族环状基团。
3.根据权利要求2所述的一种电子传输化合物，其特征在于，所述的杂原子为O、S、N、P、B、Si和Se中的一种。
4.根据权利要求3所述的一种电子传输化合物，其特征在于，所述的杂原子为O、S和N中的一种。
5.根据权利要求2所述的一种电子传输化合物，其特征在于，所述的杂环基为吗啉基、哌啶基、吡咯烷基、四氢呋喃、四氢吡喃和四氢噻吩中的一种。
6.根据权利要求1所述的一种电子传输化合物，其特征在于，所述电子传输化合物的化学结构式为式1～式69中的一种：
Figure FDA0002293919680000021
Figure FDA0002293919680000031
Figure FDA0002293919680000041
7.一种如权利要求1～6中任一项所述的电子传输化合物的合成方法，其特征在于，包括以下步骤：
Figure FDA0002293919680000071
将通式为式III的第一反应物和N-溴代丁二酰亚胺置于N,N-二甲基甲酰胺中进行搅拌反应后，得到中间体；
在保护气氛下，将上述中间体、通式为式IV或式V的第二反应物、四(三苯基膦)钯和碳酸钾加入到混合溶剂中进行升温回流反应，并经洗涤、过滤后，再置于有机溶剂中进行重结晶处理，得到所述的电子传输化合物。
8.根据权利要求7所述的一种电子传输化合物的合成方法，其特征在于，所述的步骤中，混合溶剂包括甲苯、乙醇和水。
9.根据权利要求7所述的一种电子传输化合物的合成方法，其特征在于，所述的步骤中，重结晶处理所使用的有机溶剂为1,4-二氧六环。
10.一种有机电致发光器件，包括至少一组有机物层，所述的有机物层中包括发光层和/或电子传输层，其特征在于，所述的发光层和电子传输层分别包含如权利要求1～6中任一项所述的电子传输化合物。
CN201911192497.0A 2019-11-28 2019-11-28 一种电子传输化合物、其合成方法及有机电致发光器件 Pending CN110845421A (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201911192497.0A CN110845421A (zh) 2019-11-28 2019-11-28 一种电子传输化合物、其合成方法及有机电致发光器件

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201911192497.0A CN110845421A (zh) 2019-11-28 2019-11-28 一种电子传输化合物、其合成方法及有机电致发光器件

Publications (1)

Publication Number Publication Date
CN110845421A true CN110845421A (zh) 2020-02-28

Family

ID=69606593

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201911192497.0A Pending CN110845421A (zh) 2019-11-28 2019-11-28 一种电子传输化合物、其合成方法及有机电致发光器件

Country Status (1)

Country Link
CN (1) CN110845421A (zh)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112142672A (zh) * 2020-10-20 2020-12-29 吉林奥来德光电材料股份有限公司 一种蒽类含氮有机发光化合物及其制备方法及应用
CN113004295A (zh) * 2021-03-11 2021-06-22 吉林奥来德光电材料股份有限公司 三嗪类电子传输材料、其制备方法和应用

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090233125A1 (en) * 2007-03-14 2009-09-17 Samsung Sdi Co., Ltd. Organic light-emitting device including organic layer including anthracene derivative compound
CN101560136A (zh) * 2008-04-02 2009-10-21 葛来西雅帝史派有限公司 新颖的有机电致发光化合物和使用该化合物的有机电致发光器件
CN103554011A (zh) * 2013-10-30 2014-02-05 吉林奥来德光电材料股份有限公司 一种含蒽类衍生物、制备方法及其应用
KR20140082345A (ko) * 2012-12-24 2014-07-02 에스에프씨 주식회사 헤테로아릴 치환기를 갖는 나프틸기를 포함하는 안트라센 유도체 및 이를 포함하는 유기 발광 소자
CN105143186A (zh) * 2013-02-22 2015-12-09 出光兴产株式会社 蒽衍生物、有机电致发光元件用材料、有机电致发光元件和电子设备
CN108059615A (zh) * 2017-12-21 2018-05-22 北京燕化集联光电技术有限公司 一种有机材料及其在有机电致发光器件中的应用
CN109251176A (zh) * 2017-07-12 2019-01-22 北京鼎材科技有限公司 一种有机电致发光器件

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090233125A1 (en) * 2007-03-14 2009-09-17 Samsung Sdi Co., Ltd. Organic light-emitting device including organic layer including anthracene derivative compound
CN101560136A (zh) * 2008-04-02 2009-10-21 葛来西雅帝史派有限公司 新颖的有机电致发光化合物和使用该化合物的有机电致发光器件
KR20140082345A (ko) * 2012-12-24 2014-07-02 에스에프씨 주식회사 헤테로아릴 치환기를 갖는 나프틸기를 포함하는 안트라센 유도체 및 이를 포함하는 유기 발광 소자
CN105143186A (zh) * 2013-02-22 2015-12-09 出光兴产株式会社 蒽衍生物、有机电致发光元件用材料、有机电致发光元件和电子设备
CN103554011A (zh) * 2013-10-30 2014-02-05 吉林奥来德光电材料股份有限公司 一种含蒽类衍生物、制备方法及其应用
CN109251176A (zh) * 2017-07-12 2019-01-22 北京鼎材科技有限公司 一种有机电致发光器件
CN108059615A (zh) * 2017-12-21 2018-05-22 北京燕化集联光电技术有限公司 一种有机材料及其在有机电致发光器件中的应用

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
YU-CHEN CHANG，等: "New carbazole-substituted anthracene derivatives based non-doped blue light-emitting devices with high brightness and efficiency", 《DYES AND PIGMENTS》 *
YU-CHEN CHANG，等: "New carbazole-substituted anthracene derivatives based non-doped blue light-emitting devices with high brightness and efficiency", 《DYES AND PIGMENTS》, 27 June 2013 (2013-06-27), pages 577 - 587, XP028762006, DOI: 10.1016/j.dyepig.2013.06.025 *
朱飞剑，等: "含吩噻嗪及其衍生物的聚合物有机电致发光材料的合成和器件制备", 《发光学报》 *
朱飞剑，等: "含吩噻嗪及其衍生物的聚合物有机电致发光材料的合成和器件制备", 《发光学报》, 31 October 2006 (2006-10-31), pages 715 - 718 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112142672A (zh) * 2020-10-20 2020-12-29 吉林奥来德光电材料股份有限公司 一种蒽类含氮有机发光化合物及其制备方法及应用
CN113004295A (zh) * 2021-03-11 2021-06-22 吉林奥来德光电材料股份有限公司 三嗪类电子传输材料、其制备方法和应用
CN113004295B (zh) * 2021-03-11 2022-07-19 吉林奥来德光电材料股份有限公司 三嗪类电子传输材料、其制备方法和应用

Similar Documents

Publication Publication Date Title
CN112939931B (zh) 有机电致器件用化合物、利用该化合物的有机电致器件及其电子装置
KR101678363B1 (ko) 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR101996649B1 (ko) 피렌 유도체 화합물 및 이를 포함하는 유기전계발광소자
CN104342126B (zh) 有机电致发光材料和有机电致发光器件
CN112106215A (zh) 用于有机电气元件的化合物、使用所述化合物的有机电气元件及其电子设备
KR101823704B1 (ko) 아미노안트라센 유도체 및 그것을 이용한 유기 전기 발광 소자
CN111100072A (zh) 一种有机光电化合物、其合成方法及有机电致发光器件
KR20140112924A (ko) 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR101529878B1 (ko) 유기 전기 발광 조성물 및 이를 포함하는 유기 전기 발광 소자
KR20150111271A (ko) 신규한 유기발광화합물 및 이를 포함하는 유기 발광 소자
KR20170039020A (ko) 유기 전계발광 화합물 및 유기 전계발광 소자
KR101897045B1 (ko) 유기금속 화합물 및 이를 포함하는 유기전계발광소자
CN113121493B (zh) 芳胺类化合物及制备方法、有机电致发光器件和显示装置
KR20140072295A (ko) 중수소 치환된 유기금속 착물 및 이를 포함하는 유기 발광 소자
CN112375071B (zh) 一种有机发光化合物及其制备方法与应用
CN110845422A (zh) 一种有机发光化合物、其合成方法及有机电致发光器件
KR20150145131A (ko) 신규한 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR20150017605A (ko) 화합물, 이를 포함하는 발광 재료, 유기 광전자 소자 및 상기 유기 광전자 소자를 포함하는 표시장치
KR101950893B1 (ko) 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
CN110845421A (zh) 一种电子传输化合物、其合成方法及有机电致发光器件
CN112707908B (zh) 一种有机电子材料及其应用
KR101739831B1 (ko) 유기 발광 화합물, 잉크 조성물, 유기 발광 소자 및 전자 기기
CN112979535A (zh) 一种化合物及其应用
KR20150124609A (ko) 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
CN112079833A (zh) 一种有机电致发光化合物及其制备方法和应用

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
RJ01 Rejection of invention patent application after publication
RJ01 Rejection of invention patent application after publication

Application publication date: 20200228