CN108250084A - 一种芴类衍生物及其有机发光器件 - Google Patents

一种芴类衍生物及其有机发光器件 Download PDF

Info

Publication number
CN108250084A
CN108250084A CN201810148749.9A CN201810148749A CN108250084A CN 108250084 A CN108250084 A CN 108250084A CN 201810148749 A CN201810148749 A CN 201810148749A CN 108250084 A CN108250084 A CN 108250084A
Authority
CN
China
Prior art keywords
substituted
unsubstituted
formula
layer
unsubstituted aryl
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
CN201810148749.9A
Other languages
English (en)
Inventor
刘喜庆
蔡辉
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.)
Changchun Haipurunsi Technology Co Ltd
Original Assignee
Changchun Haipurunsi Technology 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 Changchun Haipurunsi Technology Co Ltd filed Critical Changchun Haipurunsi Technology Co Ltd
Priority to CN201810148749.9A priority Critical patent/CN108250084A/zh
Publication of CN108250084A publication Critical patent/CN108250084A/zh
Pending legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C07C211/54—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 two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • 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
    • C07D401/12—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 chain containing hetero atoms as chain links
    • 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
    • C07D405/12—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 chain containing hetero atoms as chain links
    • 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
    • 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
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • 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
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • 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
    • 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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
    • 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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • 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
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only 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
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom

Abstract

本发明提供一种芴类衍生物及其有机发光器件，涉及有机光电材料技术领域。芴类结构因sp3杂化碳的存在，阻碍了π电子的流动，打断了芳香环之间的共轭，使其有较高的三线态能级；并且此类化合物的三维立体的空间结构可以有效的防止分子间的聚集，使发光薄膜不易结晶，热稳定性能较好。将此结构作为空穴传输材料制备的有机发光器件，展现出比较低的效率滚降；在三线态能级都足够大的前提下，载流子的注入/传输能力的大小和平衡程度影响器件效率，器件表现出高的发光效率，并且具有低驱动加压的优点。

Description

一种芴类衍生物及其有机发光器件
技术领域
本发明涉及有机光电材料技术领域，具体涉及一种芴类衍生物及其有机发光器件。
背景技术
近年来，有机发光二极管(OLED:Organic Light Emitting Diode)作为一种新型和有前途的显示技术逐渐进入人们的视野。它与传统的显示技术相比，在电压特性、发光亮度、发光效率、器件重量、响应速度以及观赏视角等方面具有显著优势，并因其低成本潜力，拥有广阔市场前景。
通常，OLED具有层状或层压结构。例如，典型的OLED具有阳极/有机发光层/阴极多层结构。OLED还可具有各种其它结构，例如阳极/空穴注入层/空穴传输层/发光层/电子传输层/电子注入层/阴极多层结构或阳极/空穴注入层/空穴传输层/发光层/空穴阻挡层/电子传输层/电子注入层/阴极多层结构。
空穴传输层的基本作用就是提高空穴在器件中的传输速率，并有效地将电子阻挡在发光层内，实现载流子的最大复合；同时降低空穴在注入过程中的能量势垒，提高空穴的注入效率，从而提高器件的亮度、效率和寿命。对于有机发光空穴传输材料，除了要求其具有很高的空穴迁移率外，还要求满足以下条件：
(1)能够形成无针孔的均一无定形薄膜：
(2)所形成的无定形薄膜具有很好的热稳定性：
(3)具有合适的HOMO轨道能级，以保证空穴在电极/有机层以及有机层/有机层界面之间的有效注入与传输。
目前，有机发光材料的研究已经在学术界和工业界广泛开展，大量性能优良的有机发光材料陆续被开发出来，但该技术的产业化进程仍面临许多关键问题，如何设计新的性能更好的空穴传输材料进行调节，一直是本领域技术人员亟待解决的问题。
发明内容
本发明的目的是提供一种芴类衍生物及其有机发光器件，本发明提供的化合物热稳定性能高、成膜性好，制备方法简单，由该化合物制成的有机发光器件，表现出高效率、低驱动电压和不易结晶的优点，是性能优良的有机发光材料。
本发明首先提供一种芴类衍生物，结构式为：
A-L-B (1)
其中，L选自C6～C30的取代或未取代的芳基、C3～C30的取代或未取代的杂芳基中的一种；
A为二芳基胺基，结构式如式(2)所示：
其中，R1～R3独立地选自C1～C30的取代或未取代的烷基、C1～C30的取代或未取代的烷氧基、C6～C30的取代或未取代的芳基、C6～C30的取代或未取代的芳胺基、C3～C30的取代或未取代的杂芳基中的一种，或R2、R3相互连结成环；
B选自C6～C30的取代或未取代的芳基、C6～C30的取代或未取代的芳胺基、 C3～C30的取代或未取代的杂芳基中的一种。
优选的，所述式(1)中的B为二芳基胺基，结构式如式(3)所示：
其中，Ar1、Ar2独立地选自C6～C30的取代或未取代的芳基、C3～C30的取代或未取代的杂芳基中的一种，或Ar1、Ar2相互连结成环。
优选的，所述式(1)中的B的结构式如式(3-a)、式(3-b)、式(3-c) 或式(3-d)中的一种所示：
其中，R4～R6独立地选自C1～C30的取代或未取代的烷基、C1～C30的取代或未取代的烷氧基、C6～C30的取代或未取代的芳基、C6～C30的取代或未取代的芳胺基、C3～C30的取代或未取代的杂芳基中的一种；
R7、R8独立地选自C1～C30的取代或未取代的烷基、C6～C30的取代或未取代的芳基；
X选自CRaRb、NRc、氧原子或硫原子，所述Ra～Rc独立地选自C1～C30的取代或未取代的烷基、C6～C30的取代或未取代的芳基、C3～C30的取代或未取代的杂芳基中的一种，或Ra、Rb相互连结成环；
m、n、r独立地选自0～5的整数；
p、q独立地选自0～4的整数。
优选的，所述的式(1)中的L选自如下所示的基团中的一种：
其中，R9、R10独立的选自C1～C30的烷基、C6～C30的取代或未取代的芳基中的一种，或二者相互连结成环；
Y选自NRd、氧原子或硫原子，所述Rd选自C1～C30的取代或未取代的烷基、C6～C30的取代或未取代的芳基、C3～C30的取代或未取代的杂芳基中的一种。
优选的，所述化合物选自如下结构中的一种：
本发明还提供芴类衍生物在有机发光器件中的应用。
优选的，所述有机发光器件包括阳极、阴极和有机物层，有机物层包含空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层中的至少一层；
所述有机物层中的至少一层含有所述的芴类衍生物。
优选的，所述芴类衍生物用于制备有机发光器件的空穴传输层。
本发明的有益效果：
本发明首先提供一种芴类衍生物，该芴类衍生物具有式(1)所示结构。芴类结构因sp3杂化碳的存在，阻碍了π电子的流动，打断了芳香环之间的共轭，使其有较高的三线态能级；并且此类化合物的三维立体的空间结构可以有效的防止分子间的聚集，使发光薄膜不易结晶，热稳定性能较好。将此结构作为空穴传输材料制备的有机发光器件，展现出比较低的效率滚降；在三线态能级都足够大的前提下，载流子的注入/传输能力的大小和平衡程度影响器件效率，器件表现出高的发光效率，并且具有低驱动加压的优点。
具体实施方式
为了进一步理解本发明，下面结合实施例对本发明优选实施方案进行描述，但是应当理解，这些描述只是为进一步说明本发明的特征和优点，而不是对本发明权利要求的限制。
本发明所述烷基是指烷烃分子中少掉一个氢原子而成的烃基，其可以为直链烷基、支链烷基、环烷基，实例可包括甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、戊基、异戊基、环戊基、环己基等，但不限于此。
本发明所述烷氧基是指烷基与氧原子连结后的基团，实例可包括甲氧基、乙氧基、2-丙氧基、2-环己氧基等，但不限于此。
本发明所述芳基是指芳烃分子的芳核碳上去掉一个氢原子后，剩下一价基团的总称，其可以为单环芳基或稠环芳基，实例可包括苯基、联苯基、萘基、蒽基、菲基或芘基等，但不限于此。
本发明所述杂芳基是指芳基中的一个或多个芳核碳被杂原子替代得到的基团的总称，所述杂原子包括但不限于氧、硫或氮原子，所述杂芳基可以为单环杂芳基或稠环杂芳基，实例可包括吡啶基、吡咯基、吡啶基、噻吩基、呋喃基、吲哚基、喹啉基、异喹啉基、苯并噻吩基、苯并呋喃基、二苯并呋喃基、二苯并噻吩基、咔唑基等，但不限于此。
本发明所述取代的烷基、取代的烷氧基、取代的氨基取代的芳基、取代的杂芳基、取代的氨基，所述取代基独立的选自甲基、乙基、异丙基、叔丁基、苯基、萘基、蒽基、菲基、苯并菲基、苝基、芘基、苯甲基、甲氧基、甲硫基、苯氧基、苯硫基、芴基、9,9-二甲基芴基、二苯胺基、二甲胺基、咔唑基、9-苯基咔唑基、呋喃基、噻吩基、氰基、卤素、氘基、三苯基硅基、三甲基硅基、三氟甲基、吩噻嗪基、吩噁嗪基、吖啶基、哌啶基、吡啶基、吡嗪基、三嗪基、嘧啶基、联苯基、三联苯基、硝基等，但不限于此。
本发明所述的相互连结成环是指两个基团通过化学键彼此连接。如下所示：
然而，此外，上述表述也旨在被认为是指，在其中两个基团表示苯基的情况下，氢原子所在位置键合，从而成环。如下所示：
但不限于此。
本发明首先提供一种芴类衍生物，结构式为：
A-L-B (1)
其中，L选自C6～C30的取代或未取代的芳基、C3～C30的取代或未取代的杂芳基中的一种；
A为二芳基胺基，结构式如式(2)所示：
其中，R1～R3独立地选自C1～C30的取代或未取代的烷基、C1～C30的取代或未取代的烷氧基、C6～C30的取代或未取代的芳基、C6～C30的取代或未取代的芳胺基、C3～C30的取代或未取代的杂芳基中的一种，或R2、R3相互连结成环；
B选自C6～C30的取代或未取代的芳基、C6～C30的取代或未取代的芳胺基、 C3～C30的取代或未取代的杂芳基中的一种。
优选的，所述式(1)中的B为二芳基胺基，结构式如式(3)所示：
其中，Ar1、Ar2独立地选自C6～C30的取代或未取代的芳基、C3～C30的取代或未取代的杂芳基中的一种，或Ar1、Ar2相互连结成环。
优选的，所述式(1)中的B的结构式如式(3-a)、式(3-b)、式(3-c)或式(3-d)中的一种所示：
其中，R4～R6独立地选自C1～C30的取代或未取代的烷基、C1～C30的取代或未取代的烷氧基、C6～C30的取代或未取代的芳基、C6～C30的取代或未取代的芳胺基、C3～C30的取代或未取代的杂芳基中的一种；
R7、R8独立地选自C1～C30的取代或未取代的烷基、C6～C30的取代或未取代的芳基；
X选自CRaRb、NRc、氧原子或硫原子，所述Ra～Rc独立地选自C1～C30的取代或未取代的烷基、C6～C30的取代或未取代的芳基、C3～C30的取代或未取代的杂芳基中的一种，或Ra、Rb相互连结成环；
m、n、r独立地选自0～5的整数；
p、q独立地选自0～4的整数。
优选的，所述的式(1)中的L选自如下所示的基团中的一种：
其中，R9、R10独立的选自C1～C30的烷基、C6～C30的取代或未取代的芳基中的一种，或二者相互连结成环；
Y选自NRd、氧原子或硫原子，所述Rd选自C1～C30的取代或未取代的烷基、C6～C30的取代或未取代的芳基、C3～C30的取代或未取代的杂芳基中的一种。
优选的，所述芴类衍生物选自如下结构中的任意一种：
本发明的芴类衍生物经由Buchwald-Hartwig偶联反应制备，对所述偶联反应没有特殊的限制，采用本领域技术人员所熟知的偶联反应条件即可，该制备方法简单，原料易得。
本发明还提供所述芴类衍生物在有机发光器件中的应用，本发明的芴类衍生物可以作为空穴传输材料在有机发光器件方面得到应用，所述有机发光器件包括阳极、阴极和有机物层，有机物层包含空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层中的至少一层；所述有机物层中的至少一层含有所述的芴类衍生物。所述芴类衍生物具体可以作为制备有机发光器件的空穴传输层。采用的器件结构优选具体为：附着在透光玻璃上的ITO作为阳极；本发明所得芴类衍生物作为空穴传输层；在空穴传输层上真空蒸镀CBP/Ir(ppy)3作为发光层，8-羟基喹啉铝为电子传输层，LiF作为电子注入层，金属Al作为阴极。所述有机发光器件可用于平板显示器、照明光源、指示牌、信号灯等应用领域。
本发明对以下实施例中所采用的原料没有特别的限制，可以为市售产品或采用本领域技术人员所熟知的制备方法制备得到。
实施例1：
中间体A1的制备
将三叔丁基膦(4.4mL的1.0M的甲苯溶液，1.48g，0.05mmol)、醋酸钯(0.4g，1.83mmol)和叔丁醇钠(40.4g，420mmol)添加至联苯胺(33.6g，183mmol) 和2-溴联苯(85.3g，366mmol)在脱气甲苯(1L)中的溶液，并且将该混合物在回流下加热2小时。将该反应混合物冷却至室温，用甲苯稀释并且经由硅藻土过滤。将该滤液用水稀释，并用甲苯提取，并且合并有机相，将其在真空下进行蒸发。将该残余物经由硅胶进行过滤，并重结晶。得到中间体A1(67.0g，理论值75％)。质谱m/z：488.68(计算值：488.62)。理论元素含量(％)C36H28N2： C,88.49；H,5.78；N,5.73实测元素含量(％)：C,88.47；H,5.78；N,5.75。上述结果证实获得产物为目标产品。
化合物3的制备
将三叔丁基膦(4.4mL的1.0M的甲苯溶液，1.48g，0.05mmol)、醋酸钯(0.4g，1.83mmol)和叔丁醇钠(22.8g，238mmol)添加至中间体B1(105.5g，183mmol) 和2-溴-9,9-二甲基芴(99.9g，366mmol)在脱气甲苯(1L)中的溶液，并且将该混合物在回流下加热2小时。将该反应混合物冷却至室温，用甲苯稀释并且经由硅藻土过滤。将该滤液用水稀释，并用甲苯提取，并且合并有机相，将其在真空下进行蒸发。将该残余物经由硅胶进行过滤，并重结晶。得到目标产物化合物1(84.5g，理论值60％)。质谱m/z：873.15(计算值：873.13)。理论元素含量(％)C66H52N2：C,90.79；H,6.00；N,3.21实测元素含量(％)：C,90.75； H,6.02；N,3.23。上述结果证实获得产物为目标产品。
实施例2：
中间体A2的制备
将三叔丁基膦(4.4mL的1.0M的甲苯溶液，1.48g，0.05mmol)、醋酸钯(0.4g，1.83mmol)和叔丁醇钠(40.4g，420mmol)添加至2-氨基联苯(30.9g，183mmol) 和2-溴-9,9-二甲基芴(49.9g，183mmol)在脱气甲苯(1L)中的溶液，并且将该混合物在回流下加热2小时。将该反应混合物冷却至室温，用甲苯稀释并且经由硅藻土过滤。将该滤液用水稀释，并用甲苯提取，并且合并有机相，将其在真空下进行蒸发。将该残余物经由硅胶进行过滤，并重结晶。得到中间体A2 (46.2g，理论值70％)。质谱m/z：361.45(计算值：361.48)。理论元素含量 (％)C36H28N2：C,89.71；H,6.41；N,3.87实测元素含量(％)：C,89.73；H,6.41； N,3.86。上述结果证实获得产物为目标产品。
化合物37的制备
将三叔丁基膦(4.4mL的1.0M的甲苯溶液，1.48g，0.05mmol)、醋酸钯(0.4g，1.83mmol)和叔丁醇钠(22.8g，238mmol)添加至中间体A2(137.2g，380mmol) 和5,8-二溴喹啉(52.5g，183mmol)在脱气甲苯(1L)中的溶液，并且将该混合物在回流下加热2小时。将该反应混合物冷却至室温，用甲苯稀释并且经由硅藻土过滤。将该滤液用水稀释，并用甲苯提取，并且合并有机相，将其在真空下进行蒸发。将该残余物经由硅胶进行过滤，并重结晶。得到目标产物化合物37(93.0g，理论值60％)。质谱m/z：847.35(计算值：847.39)。理论元素含量(％)C63H49N3：C,89.22；H,5.82；N,4.95实测元素含量(％)：C,89.25；H, 5.84；N,4.91。上述结果证实获得产物为目标产品。
实施例3：
中间体A3的制备
将三叔丁基膦(4.4mL的1.0M的甲苯溶液，1.48g，0.05mmol)、醋酸钯(0.4g，1.83mmol)和叔丁醇钠(40.4g，420mmol)添加至联苯胺(33.6g，183mmol) 和中间体A2(66.0g，183mmol)在脱气甲苯(1L)中的溶液，并且将该混合物在回流下加热2小时。将该反应混合物冷却至室温，用甲苯稀释并且经由硅藻土过滤。将该滤液用水稀释，并用甲苯提取，并且合并有机相，将其在真空下进行蒸发。将该残余物经由硅胶进行过滤，并重结晶。得到中间体A3(91.7g，理论值70％)。质谱m/z：716.49(计算值：716.70)。理论元素含量(％)C49H34BrN： C,82.12；H,4.78；Br,11.15；N,1.95实测元素含量(％)：C,82.12；H,4.79；Br,11.15； N,1.94。上述结果证实获得产物为目标产品。
化合物55的制备
将三叔丁基膦(4.4mL的1.0M的甲苯溶液，1.48g，0.05mmol)、醋酸钯(0.4g，1.83mmol)和叔丁醇钠(22.8g，238mmol)添加至中间体A3(131.0g，183mmol) 和二(4-联苯基)胺(59.4g，185mmol)在脱气甲苯(1L)中的溶液，并且将该混合物在回流下加热2小时。将该反应混合物冷却至室温，用甲苯稀释并且经由硅藻土过滤。将该滤液用水稀释，并用甲苯提取，并且合并有机相，将其在真空下进行蒸发。将该残余物经由硅胶进行过滤，并重结晶。得到目标产物化合物55(100.7g，理论值65％)。质谱m/z：847.35(计算值：847.39)。理论元素含量(％)C73H52N2：C,91.60；H,5.48；N,2.93实测元素含量(％)：C,91.62； H,5.45；N,2.93。上述结果证实获得产物为目标产品。
比较例1
CBP/Ir(ppy)3用作发光层物质，2-TNATA用作空穴注入层物质，NPB用作空穴传输层物质，用以制造有以下相同构造的有机发光器件： ITO/2-TNATA(80nm)/NPB(30nm)/CBP/Ir(ppy)3(30nm)/Alq3(30nm)/LiF(0.5nm)/Al (60nm)。阳极是康宁(Corning)公司的15Ω/cm2()ITO玻璃基底切割成 50mm*50mm*0.7mm大小，并将其依次在纯水、丙酮、异丙醇中各进行15分钟的超声波清洗、30分钟的UV臭氧清洗后再使用。在玻璃基底上，将2-TANATA进行真空蒸镀后形成80nm厚度的空穴注入层。在空穴注入层上将NPB进行真空蒸镀，形成30nm厚度的空穴传输层。在上面的空穴传输层上将CBP/Ir(ppy)3 (掺杂度5％)进行真空蒸镀后形成25nm的发光层。然后，在发光层上将Alq3 的化合物以30nm的厚度进行真空蒸镀，形成电子传输层。将电子传输层上LiF 0.5nm(电子注入层)和Al 600nm(阴极)依次的进行真空蒸镀。制作有机发光器件，称为比较样品1
由所述的芴类衍生物制备有机发光器件：
将所述的芴类衍生物代替NPB作为空穴传输层中的化合物，用和上述比较例1同样的方法制造了拥有ITO/2-TNATA(80nm)/所述的芴类衍生物 (30nm)/EML(30nm)/Alq3(30nm)/LiF(0.5nm)/Al(60nm)结构的有机发光器件。
对比较例1的器件与由所述的芴类衍生物制备有机发光器件的参数进行测试，采用美商吉时利仪器股份有限公司台湾分公司Keithley2400系列数字源表，柯尼卡美能达konica minolta CS-2000，CS-2000A光度计评价驱动电压、发光效率进行评价，对结果以下表1的形式展现。
表1
以上结果表明，本发明中的芴类衍生物应用于有机发光器件中，尤其是作为空穴传输材料，表现出高效率、低驱动电压的优点，是性能良好的有机发光材料。
显然，以上实施例的说明只是用于帮助理解本发明的方法及其核心思想。应当指出，对于所述技术领域的普通技术人员来说，在不脱离本发明原理的前提下，还可以对本发明进行若干改进和修饰，这些改进和修饰也落入本发明权利要求的保护范围内。

Claims (7)

1.一种芴类衍生物，其特征在于，结构式如式(1)所示：
A-L-B (1)
其中，L选自C6～C30的取代或未取代的芳基、C3～C30的取代或未取代的杂芳基中的一种；
A为二芳基胺基，结构式如式(2)所示：
其中，R1～R3独立地选自C1～C30的取代或未取代的烷基、C1～C30的取代或未取代的烷氧基、C6～C30的取代或未取代的芳基、C6～C30的取代或未取代的芳胺基、C3～C30的取代或未取代的杂芳基中的一种，或R2、R3相互连结成环；
B选自C6～C30的取代或未取代的芳基、C6～C30的取代或未取代的芳胺基、C3～C30的取代或未取代的杂芳基中的一种。
2.根据权利要求1所述的一种芴类衍生物，其特征在于，所述式(1)中的B为二芳基胺基，结构式如式(3)所示：
其中，Ar1、Ar2独立地选自C6～C30的取代或未取代的芳基、C3～C30的取代或未取代的杂芳基中的一种，或Ar1、Ar2相互连结成环。
3.根据权利要求1所述的一种芴类衍生物，其特征在于，所述式(1)中的B的结构式如式(3-a)、式(3-b)、式(3-c)或式(3-d)中的一种所示：
其中，R4～R6独立地选自C1～C30的取代或未取代的烷基、C1～C30的取代或未取代的烷氧基、C6～C30的取代或未取代的芳基、C6～C30的取代或未取代的芳胺基、C3～C30的取代或未取代的杂芳基中的一种；
R7、R8独立地选自C1～C30的取代或未取代的烷基、C6～C30的取代或未取代的芳基；
X选自CRaRb、NRc、氧原子或硫原子，所述Ra～Rc独立地选自C1～C30的取代或未取代的烷基、C6～C30的取代或未取代的芳基、C3～C30的取代或未取代的杂芳基中的一种，或Ra、Rb相互连结成环；
m、n、r独立地选自0～5的整数；
p、q独立地选自0～4的整数。
4.根据权利要求1所述的一种芴类衍生物，其特征在于，所述的式(1)中的L选自如下所示的基团中的一种：
其中，R9、R10独立的选自C1～C30的烷基、C6～C30的取代或未取代的芳基中的一种，或二者相互连结成环；
Y选自NRd、氧原子或硫原子，所述Rd选自C1～C30的取代或未取代的烷基、C6～C30的取代或未取代的芳基、C3～C30的取代或未取代的杂芳基中的一种。
5.根据权利要求1所述的一种芴类衍生物，其特征在于，所述化合物选自如下结构中的一种：
6.一种有机发光器件，其特征在于，所述有机发光器件包括阴极、阳极和置于所述两电极之间的有机化合物层，所述有机化合物层包括空穴注入层、空穴传输层，电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层中的至少一层；所述有机化合物层中至少一层含有权利要求1-5任一项所述的一种芴类衍生物。
7.根据权利要求6中所述的一种有机发光器件，其特征在于，空穴传输层中含有权利要求1-5中所述的一种芴类衍生物。
CN201810148749.9A 2018-02-13 2018-02-13 一种芴类衍生物及其有机发光器件 Pending CN108250084A (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201810148749.9A CN108250084A (zh) 2018-02-13 2018-02-13 一种芴类衍生物及其有机发光器件

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201810148749.9A CN108250084A (zh) 2018-02-13 2018-02-13 一种芴类衍生物及其有机发光器件

Publications (1)

Publication Number Publication Date
CN108250084A true CN108250084A (zh) 2018-07-06

Family

ID=62745004

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201810148749.9A Pending CN108250084A (zh) 2018-02-13 2018-02-13 一种芴类衍生物及其有机发光器件

Country Status (1)

Country Link
CN (1) CN108250084A (zh)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110357851A (zh) * 2018-03-26 2019-10-22 三星显示有限公司 杂环化合物和包括其的有机发光器件

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110357851A (zh) * 2018-03-26 2019-10-22 三星显示有限公司 杂环化合物和包括其的有机发光器件
EP3575295A1 (en) * 2018-03-26 2019-12-04 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same
US11289657B2 (en) * 2018-03-26 2022-03-29 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same
CN110357851B (zh) * 2018-03-26 2023-08-01 三星显示有限公司 杂环化合物和包括其的有机发光器件

Similar Documents

Publication Publication Date Title
TWI688137B (zh) 有機電場發光元件、顯示裝置以及照明裝置
CN107266481B (zh) 有机电场发光元件用材料、有机电场发光元件、显示装置、以及照明装置
KR102157998B1 (ko) 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
CN103249722B (zh) 用于有机电子材料的新化合物以及使用该化合物的有机电致发光器件
KR101574704B1 (ko) 신규한 화합물, 이를 포함하는 유기전계발광소자 및 유기태양전지
KR101852926B1 (ko) 유기발광 화합물 및 이를 포함하는 유기전계발광소자
JP5780132B2 (ja) ベンゾフルオレン化合物、該化合物を用いた発光層用材料および有機電界発光素子
CN109020960A (zh) 新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
WO2011071255A1 (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20110008784A (ko) 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR101401631B1 (ko) 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자
KR20160079514A (ko) 유기발광 화합물 및 이를 포함하는 유기전계발광소자
WO2014065391A1 (ja) ベンゾフルオレン化合物、該化合物を用いた発光層用材料および有機電界発光素子
CN108336246A (zh) 一种有机发光器件
KR101597865B1 (ko) 신규한 화합물 및 이를 이용한 유기 전자 소자
KR20160054870A (ko) 유기발광 화합물 및 이를 포함하는 유기전계발광소자
TW202003527A (zh) 多環芳香族化合物、有機器件用材料、有機電致發光元件、顯示裝置及照明裝置
KR20160054866A (ko) 유기발광 화합물 및 이를 포함하는 유기전계발광소자
CN107001370A (zh) 杂环化合物和使用其的有机发光器件
CN107602441A (zh) 一种稠环化合物及其有机发光器件
CN107602568A (zh) 一种基于吲哚并喹喔啉的三芳胺类衍生物及其有机发光器件
CN109467510A (zh) 一种含有芴类基团的三芳胺及其有机发光器件
CN108276335A (zh) 一种含氮杂环衍生物及其有机发光器件
CN107674060A (zh) 一种芳香族胺类衍生物及其有机发光器件
TWI794673B (zh) 雜環化合物以及包括其之有機發光裝置

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: 20180706