CN112062718B - 有机电致发光化合物和包含所述化合物的有机电致发光装置 - Google Patents

有机电致发光化合物和包含所述化合物的有机电致发光装置 Download PDF

Info

Publication number
CN112062718B
CN112062718B CN201910808091.4A CN201910808091A CN112062718B CN 112062718 B CN112062718 B CN 112062718B CN 201910808091 A CN201910808091 A CN 201910808091A CN 112062718 B CN112062718 B CN 112062718B
Authority
CN
China
Prior art keywords
compound
organic electroluminescent
substituted
unsubstituted
layer
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.)
Active
Application number
CN201910808091.4A
Other languages
English (en)
Other versions
CN112062718A (zh
Inventor
马晓宇
汪康
王进政
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
Publication of CN112062718A publication Critical patent/CN112062718A/zh
Application granted granted Critical
Publication of CN112062718B publication Critical patent/CN112062718B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • 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
    • C07D405/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D411/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D411/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms 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
    • C07D413/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero 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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
    • 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
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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
    • H10K85/657—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
    • 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
    • C09K2211/1029—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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms 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
    • C09K2211/1088—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
    • 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
    • C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms

Abstract

本发明涉及发光材料技术领域，具体涉及一种有机电致发光化合物及其制备方法和有机电致发光器件。为了解决传统空穴传输材料中存在的问题而得到理想的材料，本发明提出向吖啶的9,10位引入芳基胺和杂环的解决方案。通过引入芳基胺获得了空穴注入能力/传输能力，高功率效率、长寿命；通过引入杂环获得适当玻璃态转变温度，从而获得了优质的有机电致发光材料。由本发明提供的化合物制备的器件具有极佳电流效率和功率效率以及长寿命。本发明提供的有机电致发光化合物的制备方法，简单易行，产量高，适于工业化生产。

Description

有机电致发光化合物和包含所述化合物的有机电致发光装置
技术领域
本发明涉及发光化合物技术领域，具体涉及一种有机电致发光化合物及制法和应用。
背景技术
电致发光装置(EL装置)为自动发光装置，其优点在于其提供较宽的视角、较大的对比率和较快的响应时间。
有机EL元件是利用了如下原理的自发光元件：通过施加电场，利用由阳极注入的空穴与由阴极注入的电子的复合能使荧光性物质发光。它具有如下结构:阳极、阴极以及介于两者之间的有机层。为了提高有机EL元件的效率和稳定性，有机层包括具有不同材料的多层，例如空穴注入层（HIL）、空穴传输层（HTL）、发光层、电子传输层（ETL）和电子注入层（EIL）。
其中空穴传输层可改变空穴到发光层的空穴传输效率、发光效率、寿命等。因此，使用铜酞菁(CuPc)、4，4′-双[N-(1-萘基)-N-苯基氨基]联苯(NPB)、N，N′-二苯基-N，N′-双(3-甲基苯基)-(1，1′-联苯)-4，4′-二胺(TPD)等作为空穴传输材料。然而，使用这些材料的有机EL装置在量子效率和使用寿命方面仍存在问题。
发明内容
本发明要解决现有技术中的技术问题，提供一种具有极佳电流效率和功率效率以及长寿命的有机电致发光化合物及制法和应用。
为了解决上述技术问题，本发明的技术方案具体如下：
一种有机电致发光化合物，其由以下化学式1表示：
化学式1
其中，Ar1、Ar2和Ar3各自独立地表示经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C30芳基或经取代或未经取代的C3到C30杂芳基；或与相邻取代基连接形成单环或多环C3-C30脂环族环或芳香族环，其碳原子可置换为至少一个选自氮、氧和硫的杂原子；
优选所述Ar1、Ar2和Ar3各自独立地选自经取代或未经取代的C6-C20芳基、经取代或未经取代的C6~C26杂芳基或三苯胺基；
进一步的，优选Ar1、Ar2、Ar3选自：
其中,“*”代表可与化学式1连接的取代基团上的任意位置，且所述R’表示在其所在苯环的任意位置，X选自C或N；所述R’为氢、卤素、氰基、C1~C30的烷基、C6~C50的芳基、C7~C50的芳烷基、C7~C50的芳基烷氧基、C7~C50的芳基烷巯基或C5~C50的杂芳基，三芳胺基；优选R为氢、氰基、C1~C6的烷基、C6~C12的芳基、C5~C15的杂芳基；进一步的优选所述R’为氢、甲基、氰基、异丙基、苯基或2,4-二苯基-1,3,5-三唑；
或R’与相邻取代基连接形成经取代或未经取代的单环或多环C3-C30脂环族环或芳香族环，其碳原子可置换成至少一个选自氮、氧和硫的杂原子；优选为经取代或未经取代的C10~C16的稠芳基，C5~C14的杂芳基；进一步的优选为经取代或非经取代的萘、蒽、菲、芘、苯并呋喃、苯并噻吩或吲哚，其中所述取代基为氢、甲基或苯基；
R1和R2各自独立地表示氢、氘、卤素、氰基、羧基、硝基、羟基、经取代或未经取代的C1-C30烃类（烷基、烯基、炔基等）、经取代或未经取代的C1-C30烷氧基、经取代或未经取代的C3-C30环烷基、经取代或未经取代的C3-C30环烯基、经取代或未经取代的C3~C7杂环烷基、经取代或未经取代的C6-C30芳基、经取代或未经取代的C3~C30杂芳基、-NR4R5、-SiR6R7R8、-SR9、-OR10、-COR11、-BOR12OR13；或R1和R2与相邻取代基连接形成经取代或未经取代的单环或多环C3-C30脂环族环或芳香族环，其碳原子可置换成至少一个选自氮、氧和硫的杂原子；优选为萘、蒽、菲或芘，或取代的萘、蒽、菲或芘；其中所述取代基为氢、甲基或苯基；
R3表示经取代或未经取代的C1-C30烃类（烷基、烯基、炔基等）、经取代或未经取代的C3-C30环烷基、经取代或未经取代的C3-C30环烯基、经取代或未经取代的C3~C7杂环烷基、经取代或未经取代的C6-C30芳基、经取代或未经取代的C3~C30杂芳基。
优选R3选自经取代或未经取代的C1~C10烷基、经取代或未经取代的C6-C25芳基、经取代或未经取代的C5~C22杂芳基或三芳胺基；进一步优选R3选自经取代或未经取代的C1~C6烷基、经取代或未经取代的C6-C12芳基、经取代或未经取代的C6到C21杂芳基或三苯胺基；
优选R3为异丙基、叔丁基、戊烷、环己烷、
其中，“*”代表可与化学式1中的N原子连接的取代基团上的任意位置；X选自N或C。
其中R为氢、卤素、氰基、C1~C30的烷基、C6~C50的芳基、C7~C50的芳烷基、C7~C50的芳基烷氧基、C7~C50的芳基烷巯基或C5~C50的杂芳基。且所述—R表示在其所在苯环的任意位置。
优选R选自氢、C1~C6烷基、C6-C12芳基、C6到C21杂芳基或C15~C27的胺基；进一步的优选R选自氢、苯基、9,9-二甲基-9,10-二氢吖啶、二（[1,1’-联苯]-4-基）胺、N-（[1,1’-联苯]-4-基）-9,9-二甲基-9H-芴-2-胺。
或R3与相邻取代基连接形成经取代或未经取代的单环或多环C3-C30脂环族环或芳香族环，其碳原子可置换成至少一个选自氮、氧和硫的杂原子；优选为萘、蒽、菲或芘，或取代的萘、蒽、菲或芘；其中所述取代基为氢、甲基或苯基；
R4到R13各自独立地表示经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C30芳基或经取代或未经取代的C3~C30杂芳基；或与相邻取代基连接形成经取代或未经取代的单环或多环C3-C30脂肪族环或芳香族环；a、 b为整数1到4。a和b各自独立地表示整数1到4；优选a、b为1。
L独立地为经取代或未经取代的C6-C30芳基、经取代或未经取代的3到30元杂芳基；L1优选苯、氘代苯；
其中，所述烷基为直链烷基、支链烷基、环烷基、至少1个取代基取代的直连烷基、至少1个取代基取代的支链烷基或至少1个取代基取代的环烷基；其中，所述取代基独立的选自卤素、氰基、羟基和巯基中的一种或几种。
所述芳基优选为未取代的芳基或至少1个取代基取代的芳基；其中，所述取代基独立的选择卤素、氨基、氰基、硝基、羟基或巯基；
所述芳基烷基优选为未取代的芳基烷基或至少1个取代基取代的芳基烷基；其中，所述取代基独立的选择卤素、氨基、氰基、硝基、羟基或巯基；
所述芳基烷氧基优选为未取代的芳基烷氧基或至少1个取代基取代的芳基烷氧基；其中，所述取代基独立的选择卤素、氨基、氰基、硝基、羟基或巯基；
所述芳基烷巯基优选为未取代的芳基烷巯基或至少1个取代基取代的芳基烷巯基；其中，所述取代基独立的选择卤素、氨基、氰基、硝基、羟基或巯基；
所述杂芳基优选为未取代的杂芳基或至少1个取代基取代的杂芳基；其中，杂芳基中的杂原子为氮、硫或氧；所述取代基独立的选择卤素、氨基、氰基、硝基、羟基或巯基；
本发明的目标为提供一种具有极佳电流效率和功率效率以及长寿命的有机电致发光化合物。
本发明的特定化合物包括以下化合物，但不限于此：
一种有机电致发光化合物的制法，包括以下步骤：
步骤1、中间体1的制备
在反应容器中加入化合物2和四氢呋喃之后，在氮气气氛下使所述容器冷却，接着将正丁基锂逐滴添加到混合物中，搅拌混合物，将该混合物在室温下搅拌反应后，冷却；此后，将溶解于四氢呋喃中的化合物1逐滴添加到上述混合物中，使反应温度升温到室温，继续进行搅拌反应，接着将氯化铵水溶液添加到反应溶液中以完成反应，并且用乙酸乙酯萃取反应溶液，接着使用硫酸镁干燥经萃取的有机层，并且使用旋转式蒸发器去除溶剂，用管柱色谱法纯化剩余物质获得中间体1；
步骤2、化学式1所示化合物的制备
将中间体1、化合物3和二氯甲烷加入反应容器中之后，用氮气充分置换空气三次，将溶解于二氯甲烷中的三氟化硼乙醚逐滴添加到上述混合物中，在室温下搅拌反应，用蒸馏水淬灭，并且用二氯甲烷萃取混合物，接着使用硫酸钠干燥萃取的有机层，并且使用旋转式蒸发器去除溶剂，用柱色谱法纯化剩余物质获得化学式1所示化合物；
本发明的有机电致发光化合物可通过所属领域的技术人员已知的合成方法制备。举例来说，其可以根据以下反应流程来制备。
其中R1、R2、R3、Ar1、Ar2、Ar3、L、及a和b如上述式1中所定义，并且Hal
表示卤素。
优选所述步骤1具体包括以下步骤：
在反应容器中加入化合物2和200mL四氢呋喃之后，在氮气气氛下使所述容器冷却到-78℃，接着将正丁基锂逐滴添加到混合物中，在-78℃下搅拌混合物30分钟后，将其在室温下搅拌3小时，并且冷却到-78℃，此后，将溶解于200mL四氢呋喃中的化合物1逐滴添加到上述混合物中，添加后，使反应温度升温到室温，并且搅拌混合物16小时，接着将氯化铵水溶液添加到反应溶液中以完成反应，并且用乙酸乙酯萃取反应溶液，接着使用硫酸镁干燥经萃取的有机层，并且使用旋转式蒸发器去除溶剂，用管柱色谱法纯化剩余物质获得中间体1。
优选所述步骤2具体包括以下步骤：
将中间体1、化合物3和500L二氯甲烷加入反应容器中之后，用氮气充分置换空气三次，将溶解于100mL二氯甲烷中的三氟化硼乙醚逐滴添加到上述混合物中，在室温下搅拌混合物2小时后，用蒸馏水淬灭，并且用二氯甲烷萃取混合物，接着使用硫酸钠干燥萃取的有机层，并且使用旋转式蒸发器去除溶剂，用柱色谱法纯化剩余物质获得化学式1所示化合物。
本发明还提供了一种包含本发明化学式1所示结构的化合物的有机电致发光器件。
所述有机电致发光器件包括：
第一电极、第二电极和置于所述两电极之间的有机物层，其中，所述有机物层中包含有化学式1所示结构的化合物；化学式1所示结构的化合物可以是单一形态或与其它物质混合存在于有机物层中。即上述化合物可以包含单独的根据本发明的有机电致发光化合物，或可进一步包括一般用于有机电致发光材料的常规材料。
所述第一和第二电极中的一个是阳极，且另一个是阴极。所述有机物层包含发光层，并且进一步包含至少一个选自空穴注入层、空穴传输层、电子传输层、电子注入层、空穴阻挡层以及电子阻挡层组成的群组的层。
在发光层和空穴传输层中的至少一个中可以包含根据本发明的有机电致发光化合物。
其中，所述有机物层至少包括空穴注入层、空穴传输层、既具备空穴注入又具备空穴传输技能层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层和既具备电子传输又具备电子注入技能层中的一种或几种。
本发明中“有机物层”指的是有机电致发光器件第一电极和第二电极之间部署的全部层的术语。
当化学式1所示结构的化合物存在于所述有机物层中的发光层时，所述化学式1所示结构的化合物可以作为发光主体或者掺杂在其它荧光主体中；
当化学式1所示结构的化合物存在于所述有机物层中的空穴传输层或者空穴注入层时，所述化学式1所示结构的化合物可以作为空穴传输层、空穴注入层以及既具备空穴注入又具备空穴传输功能层。
本发明所述的包含有化学式1所示结构的化合物制备的器件可以用于有机发光器件（OLED）、有机太阳电池（OSC）、电子纸（e-Paper）、有机感光体（OPC）或有机薄膜晶体管（OTFT）。
本发明所述的器件可以通过薄膜蒸镀、电子束蒸发、物理气相沉积等方法在基板上蒸镀金属以及具有导电性的氧化物及他们的合金形成阳极，也可以采用旋转涂膜（spin-coating）或薄带带头蒸镀；还可以采用成型（tape-casting）、刮片法（doctor-blading）、丝网印刷（Screen-Printing）、喷墨印刷或热成像(Thermal-Imaging) 等方法减少层数制造。
具体实施方式
实例1：制备化合物1
在反应容器中将入溴苯60mmol和200mL四氢呋喃之后，在氮气气氛下使所述容器冷却到-78℃。接着将正丁基锂2.5M，60mmol缓慢逐滴添加到混合物中。在-78℃下搅拌混合物30分钟后，将其在室温下搅拌3小时，并且冷却到-78℃。此后，将溶解于200mL四氢呋喃中的2-氯-10-苯基-9-10H-吖啶酮60mmol缓慢逐滴添加到混合物中。添加后，使反应温度缓慢升温到室温，并且搅拌混合物16小时。接着将氯化铵水溶液添加到反应溶液中以完成反应，并且用乙酸乙酯萃取反应溶液。接着使用硫酸镁干燥萃取的有机层，并且使用旋转式蒸发器去除溶剂。用管柱色谱法纯化剩余物质获得化合物1-117.4g，83％，质谱值为349.56。
将化合物1-145mmol、三苯基胺46mmol和500L二氯甲烷加入反应容器中之后，用氮气充分置换空气三次。将溶解于100mL二氯甲烷中的三氟化硼乙醚46mmol缓慢逐滴添加到混合物中。在室温下搅拌混合物2小时后，用蒸馏水淬灭，并且用二氯甲烷萃取混合物。接着使用硫酸钠干燥萃取的有机层，并且使用旋转式蒸发器去除溶剂。用柱色谱法纯化剩余物质获得化合物1 为23.30g，92％,质谱值为576.33。
实例2：制备化合物3
按照实施例1的方法制备化合物3产率为87%，质谱值为778.88。与实施例1的不同之处在于使用中间体1-3代替中间体1-1，使用中间体2-3代替中间体2-1
实例3：制备化合物11
按照实施例1的方法制备化合物11产率为82%，质谱值为884.27。与实施例1的不同之处在于使用中间体1-11代替中间体1-1，使用中间体2-11代替中间体2-1。
实例4：制备化合物20
按照实施例1的方法制备化合物20产率为88%，质谱值为996.21。与实施例1的不同之处在于使用中间体1-20代替中间体1-1，使用中间体2-20代替中间体2-1。
实例5：制备化合物25
按照实施例1的方法制备化合物25产率为81%，质谱值为893.72。与实施例1的不同之处在于使用中间体1-25代替中间体1-1，使用中间体2-25代替中间体2-1。
实例6：制备化合物33
按照实施例1的方法制备化合物33产率为79%，质谱值为845.85。与实施例2的不同之处在于使用中间体1-33代替中间体1-1, 使用中间体2-33代替中间体2-1。
实例7：制备化合物34
按照实施例1的方法制备化合物45产率为80%，质谱值为818.45.。与实施例1的不同之处在于使用中间体1-34代替中间体1-1, 使用中间体2-34代替中间体2-1。
实例8：制备化合物41
按照实施例2的方法制备化合物41产率为78%，质谱值为923.12。与实施例1的不同之处在于使用中间体1-41代替中间体1-1, 使用中间体2-41代替中间体2-1。
实例9：制备化合物47
按照实施例1的方法制备化合物47产率为82%，质谱值为834.01。与实施例2的不同之处在于使用中间体1-47代替中间体1-1。
实例10：制备化合物51
按照实施例1的方法制备化合物51产率为85%，质谱值为898.98。与实施例1的不同之处在于使用中间体1-51代替中间体1-1。
实例11：制备化合物72
按照实施例1的方法制备化合物72产率为82%，质谱值为803.09。与实施例1的不同之处在于使用中间体1-72代替中间体1-1, 使用中间体2-72代替中间体2-1。
实施例12：制造含有化合物1的有机电致发光器件
将涂层厚度为1500Å的ITO玻璃基板放在蒸馏水中清洗2次，超声波洗涤30分钟，用蒸馏水反复清洗2次，超声波洗涤10分钟，蒸馏水清洗结束后，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5分钟，送到蒸镀机里。将已经准备好的ITO透明电极上蒸镀厚度为50nm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。然后将化合物1在形成的空穴注入层上面真空蒸镀厚度为30nm的空穴传输层。然后在上述空穴传输层上蒸镀厚度为30nm的蓝色主体材料9，10-二2-萘基蒽（ADN）和掺杂材料双4,6-二氟苯基吡啶-N,C2吡啶甲酰合铱FIrpic。主体材料和掺杂材料的重量比为95:5。接着在上述发光层上真空蒸镀厚度为40nm的TPBi作为空穴阻挡层及电子传输层。在上述电子传输层上真空蒸镀厚度为0.5nm氟化锂（LiF），作为电子注入层。最后蒸镀厚度为150nm的铝作为阴极，以此完成了有机电致发光器件的制备。对得到的器件的性能发光特性测试，测量采用KEITHLEY 2400型源测量单元，CS-2000分光辐射亮度计，以评价驱动电压，发光亮度，发光效率。
实施例13：制造含有化合物3的有机电致发光器件
将实施例12中的化合物1置换为化合物3，其他方法相同，制作含有化合物3的有机电致发光器件
实施例14：制造含有化合物11的有机电致发光器件
将实施例12中的化合物1置换为化合物11，其他方法相同，制作含有化合物11的有机电致发光器件
实施例15：制造含有化合物20的有机电致发光器件
将实施例12中的化合物1置换为化合物20，其他方法相同，制作含有化合物20的有机电致发光器件
实施例16：制造含有化合物25的有机电致发光器件
将实施例12中的化合物1置换为化合物25，其他方法相同，制作含有化合物25的有机电致发光器件
实施例17：制造含有化合物33的有机电致发光器件
将实施例12中的化合物1置换为化合物33，其他方法相同，制作含有化合物33的有机电致发光器件
实施例18：制造含有化合物34的有机电致发光器件
将实施例12中的化合物1置换为化合物34，其他方法相同，制作含有化合物34的有机电致发光器件
实施例19：制造含有化合物41的有机电致发光器件
将实施例12中的化合物1置换为化合物41，其他方法相同，制作含有化合物41的有机电致发光器件
实施例20：制造含有化合物47的有机电致发光器件
将实施例12中的化合物1置换为化合物47，其他方法相同，制作含有化合物47的有机电致发光器件
实施例21：制造含有化合物51的有机电致发光器件
将实施例12中的化合物1置换为化合物51，其他方法相同，制作含有化合物51的有机电致发光器件
实施例22：制造含有化合物72的有机电致发光器件
将实施例12中的化合物1置换为化合物72，其他方法相同，制作含有化合物72的有机电致发光器件
实施例23：
按照实施例14的方法，将空穴传输层的材料由化合物1置换为N'-二1-萘基-N，N'-二苯基-1,1'-联苯-4，4'-二胺（NPD）。
表1 为本发明实施例制备的化合物以及NPD制备的发光器件的发光特性测试结果
表1
从上表可看成本发明提供的化合物有适合的玻璃态转变温度，发光效率及寿命相对于NPD有显著的提高。
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，对于本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 (2)

1.一种有机电致发光化合物，选自以下化合物：
2.一种包含权利要求1所述的有机电致发光化合物的有机电致发光器件。
CN201910808091.4A 2019-05-25 2019-08-29 有机电致发光化合物和包含所述化合物的有机电致发光装置 Active CN112062718B (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201910442545 2019-05-25
CN2019104425450 2019-05-25

Publications (2)

Publication Number Publication Date
CN112062718A CN112062718A (zh) 2020-12-11
CN112062718B true CN112062718B (zh) 2024-02-06

Family

ID=73657909

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201910808091.4A Active CN112062718B (zh) 2019-05-25 2019-08-29 有机电致发光化合物和包含所述化合物的有机电致发光装置

Country Status (1)

Country Link
CN (1) CN112062718B (zh)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111233764B (zh) * 2020-03-31 2022-03-18 烟台显华化工科技有限公司 一类具有吖啶衍生的三芳胺结构的有机化合物及其应用
CN113121361A (zh) * 2021-03-31 2021-07-16 吉林奥来德光电材料股份有限公司 具有菲类双芳胺结构的空穴传输材料及其制备方法和应用
CN115160272B (zh) * 2021-09-15 2023-10-31 陕西莱特光电材料股份有限公司 一种含氮化合物及使用其的电子元件和电子装置
CN115322189B (zh) * 2021-09-28 2023-11-28 四川阿格瑞新材料有限公司 一种螺环化合物及其应用
CN116332978B (zh) * 2023-05-30 2023-08-29 吉林奥来德光电材料股份有限公司 一种有机化合物及其制备方法、包含其的有机电致发光器件

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103030596A (zh) * 2011-09-28 2013-04-10 昆山维信诺显示技术有限公司 一种二氢吖啶类材料及其应用
KR20130142967A (ko) * 2012-06-20 2013-12-30 에스에프씨 주식회사 이형고리 화합물 및 이를 포함하는 유기전계발광소자
CN105722944A (zh) * 2013-10-23 2016-06-29 默克专利有限公司 用于电子器件的材料
CN107109213A (zh) * 2014-12-30 2017-08-29 陶氏环球技术有限责任公司 作为用于电致发光装置的发光元件的芴衍生物
CN109232419A (zh) * 2018-09-17 2019-01-18 宁波卢米蓝新材料有限公司 一种9,10-二氢吖啶衍生物及其制备方法和用途
CN109748898A (zh) * 2018-12-29 2019-05-14 吉林奥来德光电材料股份有限公司 有机电致发光化合物及其制备方法和有机电致发光器件

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130299793A1 (en) * 2012-05-11 2013-11-14 Nichem Fine Technology Company Limted 9,10-dihydroacridine derivative and organic light emitting device comprising the same

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103030596A (zh) * 2011-09-28 2013-04-10 昆山维信诺显示技术有限公司 一种二氢吖啶类材料及其应用
KR20130142967A (ko) * 2012-06-20 2013-12-30 에스에프씨 주식회사 이형고리 화합물 및 이를 포함하는 유기전계발광소자
CN105722944A (zh) * 2013-10-23 2016-06-29 默克专利有限公司 用于电子器件的材料
CN107109213A (zh) * 2014-12-30 2017-08-29 陶氏环球技术有限责任公司 作为用于电致发光装置的发光元件的芴衍生物
CN109232419A (zh) * 2018-09-17 2019-01-18 宁波卢米蓝新材料有限公司 一种9,10-二氢吖啶衍生物及其制备方法和用途
CN109748898A (zh) * 2018-12-29 2019-05-14 吉林奥来德光电材料股份有限公司 有机电致发光化合物及其制备方法和有机电致发光器件

Also Published As

Publication number Publication date
CN112062718A (zh) 2020-12-11

Similar Documents

Publication Publication Date Title
CN109748898B (zh) 有机电致发光化合物及其制备方法和有机电致发光器件
CN112062718B (zh) 有机电致发光化合物和包含所述化合物的有机电致发光装置
KR101427605B1 (ko) 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계발광 소자
CN109796960B (zh) 一种有机电致发光化合物及制法和应用
US20060063027A1 (en) Organic electroluminescent element
CN109776334B (zh) 有机电致发光化合物及其制法和器件
KR20100109293A (ko) 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계발광 소자
CN112079834B (zh) 一种有机电致发光化合物及其应用
CN109970575B (zh) 有机电致发光化合物及其制法和应用
CN110330472B (zh) 一种蓝光材料及其制备方法和应用
CN109180560A (zh) 一种有机发光化合物及制法和含该化合物的有机电致发光器件
KR20120020901A (ko) 신규한 유기 전자재료용 화합물 및 이를 채용하고 있는 유기 전계 발광 소자
US6657224B2 (en) Organic light emitting diode devices using thermostable hole-injection and hole-transport compounds
CN109776393A (zh) 一种有机发光化合物及制法和该化合物的有机电致发光器件
WO2020073605A1 (zh) 一种有机发光化合物及制法和含该化合物的有机电致发光器件
KR102237159B1 (ko) 유기화합물 및 이를 이용한 유기발광다이오드소자
CN114702489A (zh) 一种含有菲和邻菲罗啉的有机电子材料及其应用
JP2014110315A (ja) 有機電界発光素子用正孔輸送材料及びそれを用いた有機電界発光素子
CN112125812B (zh) 一种化合物及其应用以及包含该化合物的器件
JP2006245172A (ja) 発光素子
KR101508145B1 (ko) 유기 발광 화합물, 이의 제조 방법 및 이를 포함하는 유기 전계 발광 소자
CN110010773B (zh) 一种调节载流子迁移率的发光层及有机电致发光器件
CN115636755A (zh) 一种萘基取代双芳胺化合物及其应用
CN115160273A (zh) 一种含有二苯并杂环的化合物及其制备方法和应用
CN109369641A (zh) 一种有机电致器件用化合物

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
GR01 Patent grant
GR01 Patent grant