CN106565434B - 一种蒽类化合物及其制备方法以及有机发光器件 - Google Patents

一种蒽类化合物及其制备方法以及有机发光器件 Download PDF

Info

Publication number
CN106565434B
CN106565434B CN201610963975.3A CN201610963975A CN106565434B CN 106565434 B CN106565434 B CN 106565434B CN 201610963975 A CN201610963975 A CN 201610963975A CN 106565434 B CN106565434 B CN 106565434B
Authority
CN
China
Prior art keywords
radical
organic
formula
condensed ring
heterocyclic group
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
CN201610963975.3A
Other languages
English (en)
Other versions
CN106565434A (zh
Inventor
崔敦洙
王钊
毕岩
秦翠英
胡晓明
高春吉
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 CN201610963975.3A priority Critical patent/CN106565434B/zh
Publication of CN106565434A publication Critical patent/CN106565434A/zh
Application granted granted Critical
Publication of CN106565434B publication Critical patent/CN106565434B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/04—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reaction of ammonia or amines with olefin oxides or halohydrins
    • 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
    • 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
    • C07C217/94—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 bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
    • C07C43/275—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings having all ether-oxygen atoms bound to carbon atoms of 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
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • 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
    • C07D213/60—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C07D213/643—2-Phenoxypyridines; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
    • C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
    • 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
    • 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
    • H10K50/15—Hole transporting 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]
    • H10K50/17—Carrier injection 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
    • 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
    • H10K85/649—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
    • 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
    • C09K2211/1018—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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

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)
  • Chemical Kinetics & Catalysis (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

本发明提供了一种蒽类化合物，具有式(Ⅰ)结构：其中，Q为C1～60烷基、C6～60芳基、C5～60稠环基或C5～60杂环基；Ar为C6～60芳基、C5～60稠环基或C5～60杂环基；Ar1为H、C1～60烷基、C1～60烷氧基、C1～60醚基、C6～60芳基、C6～60稠环基、C6～60杂环基和C6～60芳胺基。与现有技术相比，本发明提供的蒽类化合物通过蒽连接芳香化合物，通过引入Q、Ar、Ar1基团，使有机化合物应用于有机发光器件后器件发蓝光，同时通过上述基团调节发光波长等手段，使有机发光器件发光效率高，使用寿命长。

Description

一种蒽类化合物及其制备方法以及有机发光器件
技术领域
本发明涉及有机光电材料技术领域，尤其涉及一种蒽类化合物及其制备方法以及有机发光器件。
背景技术
有机发光器件(OLED)是由阴极、阳极及阴极和阳极之间插入的有机物层构成。器件的组成是透明ITO阳极、空穴注入层(TIL)、空穴传输层(HTL)、发光层(EL、空穴阻挡层(HBL)、电子传输层(ETL)、电子注入层(EIL)、LiAl等阴极形成，按需要可省略1～2有机层。
有机发光器件的两个电极之间形成电压一边从阴极电子注入。另一边阳极注入空穴。这电子和空穴在发光层再结合形成激发态，激发态回到稳定的基态。使具有荧光或磷光特性的有机化合物产生了光发射。
目前，发光材料分为荧光材料和磷光材料，发光层的形成方法是荧光主体材料中掺杂磷光材料(有机金属)的方法和荧光主体材料掺杂荧光(包含氮的有机物)掺杂剂的方法及发光体里利用掺杂剂(DCM，Rubrene，DCJTB等)具现长波长的方法，通过这样的参杂改善发光波长，效率，驱动电压，寿命等因素。一般形成发光层材料是具有苯、萘、芴、螺二芴、蒽、芘、咔唑等中心体和苯、联苯、萘、杂环等配体；对位、间位、邻位的结合位置及氰基、氟、甲基、叔丁基等置换结构。
在OLED面板发展到大型化，需要更细腻和色彩更鲜明的材料，其中重点需求是蓝色材料，尤其是高效率发光效率的材料。
发明内容
有鉴于此，本发明要解决的技术问题在于提供一种蒽类化合物及其制备方法以及一种有机发光器件，由所述蒽类化合物制备的有机发光器件具有较高的发光效率以及较长的寿命。
本发明提供了一种蒽类化合物，具有式(Ⅰ)结构：
Figure BDA0001145196420000021
其中，
Q为C1～60烷基、C6～60芳基、C5～60稠环基或C5～60杂环基；
Ar为C6～60芳基、C5～60稠环基或C5～60杂环基；
Ar1为H、C1～60烷基、C1～60烷氧基、C1～60醚基、C6～60芳基、C6～60稠环基、C6～60杂环基和C6～60芳胺基。
优选的，所述蒽类化合物具有以下结构：
Figure BDA0001145196420000022
优选的，所述Q为C1～20烷基、C6～20芳基或C5～20杂环基。
优选的，所述Ar1为H、C1～30醚基、C6～30芳基、C6～30稠环基、C6～30杂环基和C6～30芳胺基。
优选的，所述Ar1选自式(a-1)～式(a-8)所示结构：
Figure BDA0001145196420000023
Figure BDA0001145196420000031
L1选自0，1或2；X独立的选自CH、N或C-R6；
Ar2为C6～60芳基、C6～60稠环基或C5～60杂环基；
R1、R2、R3独立的选自H、C1～60烷基、C1～60醚基、C6～60芳基、C7～60芳基醚、C6～60芳胺基、C5～60稠环基或C5～60杂环基；
R4、R5独立的选自C6～60芳基、C7～60芳基醚、C6～60芳胺基、C5～60稠环基或C5～60杂环基；
R6选自C1～60烷基、C1～60醚基、C6～60芳基、C6～60芳胺基、C5～60稠环基或C5～60杂环基。
优选的，所述蒽类化合物具有以下任一结构：
Figure BDA0001145196420000041
Figure BDA0001145196420000051
Figure BDA0001145196420000061
本发明提供了一种蒽类化合物的制备方法，包括：
将式(II)所示的硼酸化合物，与式(III)所示的溴化物进行取代反应，得到式(Ⅰ)所示的蒽类化合物；
Figure BDA0001145196420000071
Ar1-Ar-Br式(III)；
或者采用式(V)所示的溴化物，与式(VI)所示的硼酸化合物进行取代反应，得到式(Ⅰ)所示的蒽类化合物；
BrAr1式(V)；
Figure BDA0001145196420000072
其中，
Q为C1～60烷基、C6～60芳基、C5～60稠环基或C5～60杂环基；
Ar为C6～60芳基、C5～60稠环基或C5～60杂环基；
Ar1为H、C1～60烷基、C1～60烷氧基、C1～60醚基、C6～60芳基、C6～60稠环基、C6～60杂环基和C6～60芳胺基。
本发明提供了一种有机发光器件，包括上述技术方案所述的蒽类化合物或上述技术方案所述的制备方法制备的蒽类化合物。
优选的，包括第一电极、第二电极和设置于所述第一电极与第二电极之间的有机物层；所述有机物层包括权利要求1～6任意一项所述的蒽类化合物或权利要求7所述的制备方法制备的蒽类化合物。
本发明提供了一种有机光电材料，包括上述技术方案所述的蒽类化合物或上述技术方案所述的制备方法制备的蒽类化合物；所述有机光电材料包括有机太阳电池、电子纸、有机感光体或有机晶体管。
与现有技术相比，本发明提供了一种蒽类化合物，具有式(Ⅰ)结构：其中，Q为C1～60烷基、C6～60芳基、C5～60稠环基或C5～60杂环基；Ar为C6～60芳基、C5～60稠环基或C5～60杂环基；Ar1为H、C1～60烷基、C1～60烷氧基、C1～60醚基、C6～60芳基、C6～60稠环基、C6～60杂环基和C6～60芳胺基。与现有技术相比，本发明提供的蒽类化合物通过蒽连接芳香化合物，通过引入Q、Ar、Ar1基团，使有机化合物应用于有机发光器件后器件发蓝光，同时通过上述基团调节发光波长等手段，使有机发光器件发光效率高，使用寿命长。
具体实施方式
本发明提供了一种蒽类化合物，具有式(Ⅰ)结构：
Figure BDA0001145196420000081
其中，
Q为C1～60烷基、C6～60芳基、C5～60稠环基或C5～60杂环基；所述Q优选为H、取代或非取代C1～30烷基，取代或非取代C6～30芳基、取代或非取代C5～30稠环基或取代或非取代C5～30杂环基；更优选为取代或非取代C1～20烷基、取代或非取代C6～20芳基或取代或非取代C5～20杂环基；在本发明的具体实施例中，Q最优选为甲基、乙基、丙基、丁基、戊基、苯基、吡啶基、呋喃基、萘基；
Ar为取代或非取代C6～60芳基、取代或非取代C5～60稠环基或取代或非取代C5～60杂环基；优选为取代或非取代C5～30稠环基；在本发明的具体实施例中，所述Ar更优选为式(m-1)或式(m-2)所示；
Figure BDA0001145196420000082
Ar1为H、取代或非取代C1～60烷基、取代或非取代C1～60烷氧基、取代或非取代C1～60醚基、取代或非取代C6～60芳基、取代或非取代C6～60稠环基、取代或非取代C6～60杂环基和取代或非取代C6～60芳胺基；优选为H、取代或非取代C1～30醚基、取代或非取代C6～30芳基、取代或非取代C6～30稠环基、取代或非取代C6～30杂环基和取代或非取代C6～30芳胺基。
在本发明中，需要指出的是，-O-Q表示取代基可以在所在芳香环的任意位置；
其中，所述烷基优选为直链烷基、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和氰基中的一种或几种，所述烷基上取代基的个数优选为1～5，更优选为2、3或4。
所述烷氧基优选为未取代的烷氧基或至少1个取代基取代的烷氧基；其中，所述取代基独立的选自卤素和氰基中的一种或几种，所述烷氧基上取代基的个数优选为1～5，更优选为2、3或4。
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和/或氰基；所述芳基上取代基的个数优选为1～5，更优选为2、3或4。
所述杂环基优选为未取代的杂环基或至少1个取代基取代的杂环基；其中，杂环基中的杂原子为氮、硫或氧；所述取代基独立的选择卤素和/或氰基；所述杂环基上取代基的个数优选为1～5，更优选为2、3或4。
所述稠环基优选为未取代的稠环基或至少1个取代基取代的稠环基；其中，所述取代基独立的选择卤素和/或氰基；所述稠环基上取代基的个数优选为1～5，更优选为2、3或4。
在本发明中，所述蒽类化合物优选具有以下结构：
Figure BDA0001145196420000091
Q为C1～60烷基、C6～60芳基、C5～60稠环基或C5～60杂环基；所述Q优选为H、取代或非取代C1～30烷基，取代或非取代C6～30芳基、取代或非取代C5～30稠环基或取代或非取代C5～30杂环基；更优选为取代或非取代C1～20烷基、取代或非取代C6～20芳基或取代或非取代C5～20杂环基；在本发明的具体实施例中，Q最优选为甲基、乙基、丙基、丁基、戊基、苯基、吡啶基、呋喃基、萘基；
Ar1为H、C1～60烷基、C1～60烷氧基、C1～60醚基、C6～60芳基、C6～60稠环基、C6～60杂环基和C6～60芳胺基；优选为H、取代或非取代C1～30醚基、取代或非取代C6～30芳基、取代或非取代C6～30稠环基、取代或非取代C6～30杂环基和取代或非取代C6～30芳胺基。
在本发明中，所述Ar1优选选自式(a-1)～式(a-8)所示结构：
Figure BDA0001145196420000092
Figure BDA0001145196420000101
其中，L1选自0，1或2；X独立的选自CH、N或C-R6；
Ar1为C6～60芳基、C6～60稠环基或C5～60杂环基；优选为C6～30芳基、C6～30稠环基或C5～30杂环基；更优选为C6～20芳基、C6～20稠环基或C5～20杂环基；最优选为C6～15芳基、C6～15稠环基；在本发明的具体实施例中，最最优选为苯基或萘基。
R1、R2、R3独立的选自H、C1～60烷基、C1～60醚基、C6～60芳基、C7～60芳基醚、C6～60芳胺基、C5～60稠环基或C5～60杂环基；优选为H、C1～20烷基、C1～20醚基、C6～20芳基、C7～20芳基醚、C6～20芳胺基、C5～20稠环基或C5～20杂环基；在本发明的具体实施例中，更优选为H、甲氧基、乙氧基、丙氧基、吡啶基、呋喃基、苯基、萘基。
R4、R5独立的选自C6～60芳基、C7～60芳基醚、C6～60芳胺基、C5～60稠环基或C5～60杂环基；优选为C6～30芳基、C6～30稠环基或C5～30杂环基；更优选为C6～20芳基、C6～20稠环基或C5～20杂环基；最优选为C6～15芳基、C6～15稠环基；在本发明的具体实施例中，最最优选为苯基或萘基。
R6选自C1～60烷基、C1～60醚基、C6～60芳基、C6～60芳胺基、C5～60稠环基或C5～60杂环基；优选为H、C1～20烷基、C1～20醚基、C6～20芳基、C6～20芳胺基、C5～20稠环基或C5～20杂环基；在本发明的具体实施例中，更优选为H、甲氧基、乙氧基、丙氧基、吡啶基、呋喃基、苯基、萘基。
即，所述蒽类化合物更优选具有以下结构：
Figure BDA0001145196420000102
Figure BDA0001145196420000111
其中，L1、X、Ar2、R1、R2、R3、R4、R5、R6范围同上，在此不再赘述。
在本发明中，所述蒽类化合物最优选具有以下任一结构：
Figure BDA0001145196420000121
Figure BDA0001145196420000131
Figure BDA0001145196420000141
其中，未显示基团为甲基的省略。
本发明提供了一种蒽类化合物的制备方法，包括：
将式(II)所示的硼酸化合物，与式(III)所示的溴化物进行取代反应，得到式(Ⅰ)所示的蒽类化合物；
Figure BDA0001145196420000151
Ar1-Ar-Br式(III)；
或者采用式(V)所示的溴化物，与式(VI)所示的硼酸化合物进行取代反应，得到式(Ⅰ)所示的蒽类化合物；
BrAr1式(V)；
Figure BDA0001145196420000152
其中，
Q为C1～60烷基、C6～60芳基、C5～60稠环基或C5～60杂环基；
Ar为C6～60芳基、C5～60稠环基或C5～60杂环基；
Ar1为H、C1～60烷基、C1～60烷氧基、C1～60醚基、C6～60芳基、C6～60稠环基、C6～60杂环基和C6～60芳胺基。
在本发明中，所述反应优选在催化剂四三苯基膦钯的催化作用下进行。所述反应的溶剂优选为甲苯。所述反应的温度优选为80～100℃，反应时间优选为8～12h。
反应结束后，优选采用过柱分离的方法得到产物纯品。
在本发明中，先将式(II)所示的硼酸化合物与Br-Ar-Br式(IV)所示的溴化物进行取代反应、与硼酸三异丙酯反应、再与BrAr1式(V)所示的溴化物取代反应，得到式(Ⅰ)所示的蒽类化合物，具体路线包括：
此外，本发明对式(II)结构的化合物与式(III)结构的化合物的来源没有特殊限定，通过本领域公知的制备方法制得即可，具体可以为:
Figure BDA0001145196420000154
反应条件同上，在此不再赘述。
式(A-1)所示化合物与硼酸三异丙酯进行反应，得到式(B-1)所示硼酸化合物；
所述反应优选在正丁基锂的催化作用下进行。
所述反应的溶剂优选为四氢呋喃。
所述反应中，式(A-1)所示化合物与硼酸三异丙酯、正丁基锂的混合温度优选为-78℃，滴加完毕后，反应温度优选为室温，反应时间优选为4～6h。
反应结束后，优选的，加水淬灭反应，萃取并蒸干得到产物。
本发明中，式(Ⅰ)所示的蒽类类化合物的制备方法不限定于上述方法，本领域技术人员可以根据以上反应自由选择反应基团，本领域技术人员可以根据产物结构以及上述反应方法，推知其制备方法。上述反应条件同上，在此不再赘述。
在本发明中，得到的溴代产物可以继续和咔唑反应，得到目标产物，反应条件和路线为本领域技术人员熟知的反应，在此不再赘述，例如：
Figure BDA0001145196420000162
本发明提供的蒽类类化合物制备方法简单，易于产业化。
本发明还提供了一种有机发光器件，包括上述的式(I)所示的蒽类类化合物。
所述有机发光器件为本领域技术人员熟知的有机发光器件即可，本发明优选包括第一电极、第二电极和设置于所述第一电极与第二电极之间的有机物层；所述有机物层包含上述的含联蒽类化合物。所述含联蒽类化合物可以是单一形态，或与其他物质混合，包含于上述有机物层中。
本发明中，所述有机物层是指有机发光器件第一电极和第二电极之间的全部层。所述有机物层中的至少一层为发光层。
按照本发明，所述有机物层优选包括空穴注入层、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、电子注入层与既具备电子传输又具备电子注入技能层中的一层或多层，更优选包括依次设置的空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层与电子注入层或依次设置的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、空穴阻挡层与既具备电子传输又具备电子注入技能层。
当本发明有机物层包含空穴注入层、空穴传输层或既具备空穴注入又具备空穴传输技能层时，优选所述空穴注入层、空穴传输层或既具备空穴注入又具备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。
当本发明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；所述磷光主体、荧光主体、磷光掺杂材料与荧光掺杂材料中的一种或多种为式(I)所示的蒽类类化合物。
所述发光层还可优选为红色、黄色或青色发光层，所述蒽类类化合物为红色、黄色或青色发光层的主体或掺杂物质。如，当所述发光层为青色发光层时，所述式(I)所示的蒽类类化合物在用于青色主体或青色掺杂时，可提供高效率、高亮度、高分辨率及长寿命的有机发光器件。
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式(I)所示的蒽类类化合物和/或金属化合物。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式(I)所示的蒽类类化合物。
本发明提供的有机发光器件，利用式(I)所示的蒽类类化合物及常规材料制成即可，本发明对所述有机发光器件的制备方法并无限定，本领域常规方法即可，本发明优选利用薄膜蒸镀、电子束蒸发或物理气相沉积等方法在基板上蒸镀金属及具有导电性的氧化物及它们的合金形成阳极，然后在其上形成有机物层及蒸镀阴极，得到有机发光器件。
本发明将有机物层、阳极物质按顺序蒸镀到外基板上阴极物质层，制作有机发光器件。
所述有机物层可以同时包括上述的空穴注入层、空穴传输层、发光层、空穴阻挡层及电子传输层的多层结构，并且这些多层结构可按照上述薄膜蒸镀、电子束蒸发或物理气相沉积等方法蒸镀，也可使用多样的高分子材料溶剂工程替代蒸镀方法，如旋转涂膜(spin-coating)、薄带成型(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。
本发明提供的有机发光器件按照使用的材料也可分为前面发光、背面发光或两面发光；并且该有机发光器件可以同样原理应用在有机发光器件(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)上。
本发明提供的式(I)所示的蒽类类化合物在有机太阳电池、照明用OLED、柔性OLED、有机感光体及有机晶体管等有机器件中也可按照适用有机发光器件的原理适用。
本发明还提供了一种有机光电材料，包括上述式(I)所示的蒽类类化合物；所述有机光电材料包括有机太阳电池、电子纸、有机感光体或有机晶体管。
为了进一步说明本发明，下面结合实施例对本发明提供的蒽类化合物及其制备方法以及有机发光器件进行详细描述。
实施例1
中间体1-溴-2-苯氧基苯(A-1)的合成：
Figure BDA0001145196420000181
取苯酚0.1mol，溶于100mL无水四氢呋喃中，搅拌，准确称量0.4mol氢化钠分批次加到反应瓶中，不要太快，防止太多气泡产生，加完后溶液呈现黄色，再加入1-溴-2-碘苯0.11mol(分批加入)室温反应过夜；将得到的反应产物过滤，除去固体物质，滤液旋干，加入二氯甲烷溶解，过柱用石油醚：乙酸乙酯＝1：5(体积比)冲柱，得到1-溴-2-苯氧基苯(中间体A-1)(0.05mol，y＝50％)。质谱：249.97。
实施例2
中间体A-2～A-7的合成：
按照上述实施例1中间体A-1的合成方法，用相同摩尔量比制备得到表1所示的化合物，表1是本发明实施例2反应物质、生成物质及产率汇总。
表1实施例2反应物质、生成物质及产率汇总
Figure BDA0001145196420000191
实施例3
2-苯氧基苯基硼酸(B-1)的合成：
Figure BDA0001145196420000192
将1-溴-2-苯氧基苯0.018mol溶解于100ml，干燥的THF中，后加入干燥过的500ml三口瓶中，N2保护下-78℃反应30min，缓慢滴加正丁基锂0.027mol，滴加结束后保持-78℃反应3h，再缓慢滴加硼酸三异丙酯0.02mol，滴加结束后将反应保持在-78℃反应2h，缓慢升温至室温，反应过夜，TLC监测反应结束后，用水缓慢淬灭反应液，萃取蒸干，得到2-苯氧基苯基硼酸(B-1)0.0144mol，产率为80％。质谱：214.06。
实施例4
中间体B-2～B-7的合成
按照上述实施例3中间体B-1的合成方法，用相同摩尔量比制备得到表2所示化合物，表2是本发明实施例4反应物质、生成物质及产率汇总。
表2本发明实施例4反应物质、生成物质及产率汇总
Figure BDA0001145196420000193
Figure BDA0001145196420000201
实施例5
9-溴-10-(2-甲氧基苯基)菲(C-1)的合成：
Figure BDA0001145196420000202
将2-甲氧基苯基硼酸0.10mol，9,10-二溴菲0.12mol，四三苯基膦钯7.0g，加入到反应瓶中，加入甲苯600mL，碳酸钠水溶液(2N,250mL)氮气保护，油浴90℃反应，过夜。后处理过程：体系降温，分液，旋干甲苯，剩余物用二氯甲烷全溶，再加入等量的石油醚，过硅胶漏斗，并用二氯甲烷：石油醚＝1：2(体积比)冲洗，直到无产品点流出，收集滤液，并旋干溶剂，得深色固体(C-1)(0.081mol，y＝81％)。质谱：362.05。
实施例6
中间体C-2～C-16的合成
按照上述实施例5中间体C-1的合成方法，用相同摩尔量比制备得到表3所示化合物，表3是本发明实施例6反应物质、生成物质及产率汇总。
表3本发明实施例6反应物质、生成物质及产率汇总
Figure BDA0001145196420000203
Figure BDA0001145196420000211
Figure BDA0001145196420000221
实施例7
中间体D-1～D-13的合成
按照上述实施例3中间体B-1的合成方法，用相同摩尔量比制备得到表4所示化合物，表4是本发明实施例7反应物质、生成物质及产率汇总。
表4本发明实施例7反应物质、生成物质及产率汇总
Figure BDA0001145196420000222
Figure BDA0001145196420000231
实施例8
中间体E-1～E-5的合成
按照上述实施例5中间体C-1的合成方法，用相同摩尔量比制备得到表5所示化合物，表5是本发明实施例8反应物质、生成物质及产率汇总。
表5本发明实施例8反应物质、生成物质及产率汇总
Figure BDA0001145196420000241
实施例9
中间体F-1～F-5的合成
按照上述实施例3中间体B-1的合成方法，用相同摩尔量比制备得到表6所示化合物，表6是本发明实施例9反应物质、生成物质及产率汇总。
表6本发明实施例9反应物质、生成物质及产率汇总
Figure BDA0001145196420000242
Figure BDA0001145196420000251
实施例10
中间体G-1～G-13的合成
按照上述实施例5中间体C-1的合成方法，用相同摩尔量比制备得到表7所示化合物，表7是本发明实施例10反应物质、生成物质及产率汇总。
表7本发明实施例10反应物质、生成物质及产率汇总
Figure BDA0001145196420000252
Figure BDA0001145196420000261
实施例11
中间体H-1～H-13的合成
按照上述实施例3中间体B-1的合成方法，用相同摩尔量比制备得到表8所示化合物，表8是本发明实施例11反应物质、生成物质及产率汇总。
表8本发明实施例11反应物质、生成物质及产率汇总
Figure BDA0001145196420000271
Figure BDA0001145196420000281
实施例12
按照上述实施例5中间体C-1的合成方法，用相同摩尔量比制备得到表9所示化合物，表9是本发明实施例12反应物质、生成物质及产率汇总。
表9本发明实施例12反应物质、生成物质及产率汇总
Figure BDA0001145196420000282
Figure BDA0001145196420000291
Figure BDA0001145196420000301
Figure BDA0001145196420000311
Figure BDA0001145196420000321
Figure BDA0001145196420000331
实施例13
I-53的合成：
Figure BDA0001145196420000332
将4-异丙基胺0.10mol和叔丁醇钠0.30mol，甲苯400mL加入到反应瓶中，搅拌30分钟，氮气保护，然后加入1-溴-4-异丙基苯0.12mol、三(二亚卞基丙酮)二钯1.5g，最后加入三叔丁基膦4g，升温到100℃反应24小时；后处理过程：体系降温，加入水终止反应，过滤，滤液分液，旋干甲苯，加入少量二氯甲烷溶解固体，石油醚:二氯甲烷＝3:1(体积比)过柱分离，得固体(E-1)(0.05mol，y＝50％)。
实施例14
按照上述实施例13I-53的合成方法，制备得到表10所示化合物，表10是本发明实施例14反应物质、生成物质及产率汇总。
表10本发明实施例14反应物质、生成物质及产率汇总
Figure BDA0001145196420000351
实施例15
将费希尔公司涂层厚度为
Figure BDA00011451964200003511
的ITO玻璃基板放在蒸馏水中清洗2次，超声波洗涤30min，再用蒸馏水反复清洗2次，超声波洗涤10min，水清洗结束后，按异丙醇、丙酮、甲醇按顺序洗涤30min，干燥，转移到等离子体清洗机中，将上述基板洗涤5min，送到蒸镀机中；将已经准备好的ITO透明电极上蒸镀空穴注入层2-TNATA蒸镀
Figure BDA0001145196420000352
空穴传输层a-NPD蒸镀
Figure BDA0001145196420000353
蓝色主体材料为表9和表10中物质和比较物质AND(9,10-Di(2-naphthyl)anthracene)跟掺杂TPPDA(N1,N1,N6,N6-四苯基芘-1,6-二胺)5％蒸镀
Figure BDA0001145196420000354
空穴阻挡层及空穴传输层TPBi
Figure BDA0001145196420000355
阴极LiF
Figure BDA0001145196420000356
Al
Figure BDA0001145196420000357
上述过程有机物蒸镀速度是保持LiF是
Figure BDA0001145196420000359
Al是
Figure BDA00011451964200003510
Figure BDA0001145196420000361
上述方法得到的有机发光器件的电子发光特性见表11。
表11本发明实施例15和比较例制备的发光器件的发光特性测试结果
Figure BDA0001145196420000362
从上述表11中可以看出利用本发明的蒽类化合物制备的有机发光器件的发光效率及寿命特性均有显著的提高。
本发明利用新的蒽类化合物制备得到有机发光器件，具有较高的发光效率和较长的寿命结果，因此可应用于实用性高的OLED产业。本发明的有机发光器件可适用于平面面板显示、平面发光体、照明用面发光OLED发光体、柔性发光体、复印机、打印机、LCD背光灯或计量机类的光源、显示板、标识等。
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 (5)

1.一种蒽类化合物，其特征在于，所述蒽类化合物具有以下任一结构：
Figure FDA0002214666870000011
2.一种权利要求1所述的蒽类化合物的制备方法，包括：
将式(II)所示的硼酸化合物，与式(III)所示的溴化物进行取代反应，得到式(Ⅰ)所示的蒽类化合物；
Figure FDA0002214666870000012
Ar1-Ar-Br式(III)；
或者采用式(V)所示的溴化物，与式(VI)所示的硼酸化合物进行取代反应，得到式(Ⅰ)所示的蒽类化合物；
Br-Ar1式(V)；
Figure FDA0002214666870000013
其中，
Q为C1～20烷基、C6～20芳基或C5～20杂环基；
Ar为C6～60芳基、C5～60稠环基或C5～60杂环基；
Ar1选自式(a-1)～式(a-8)所示结构：
Figure FDA0002214666870000021
L1选自0，1或2；X独立的选自CH、N或C-R6；
Ar2为C6～60芳基、C6～60稠环基或C5～60杂环基；
R1、R2、R3独立的选自H、C1～60烷基、C1～60醚基、C6～60芳基、C7～60芳基醚、C6～60芳胺基、C5～60稠环基或C5～60杂环基；
R4、R5独立的选自C6～60芳基、C7～60芳基醚、C6～60芳胺基、C5～60稠环基或C5～60杂环基；
R6选自C1～60烷基、C1～60醚基、C6～60芳基、C6～60芳胺基、C5～60稠环基或C5～60杂环基。
3.一种有机发光器件，包括权利要求1所述的蒽类化合物。
4.根据权利要求3所述的有机发光器件，其特征在于，包括第一电极、第二电极和设置于所述第一电极与第二电极之间的有机物层；所述有机物层包括权利要求1所述的蒽类化合物。
5.一种有机光电材料，其特征在于，包括权利要求1所述的蒽类化合物；所述有机光电材料包括有机太阳电池、电子纸、有机感光体或有机晶体管。
CN201610963975.3A 2016-10-28 2016-10-28 一种蒽类化合物及其制备方法以及有机发光器件 Active CN106565434B (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201610963975.3A CN106565434B (zh) 2016-10-28 2016-10-28 一种蒽类化合物及其制备方法以及有机发光器件

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201610963975.3A CN106565434B (zh) 2016-10-28 2016-10-28 一种蒽类化合物及其制备方法以及有机发光器件

Publications (2)

Publication Number Publication Date
CN106565434A CN106565434A (zh) 2017-04-19
CN106565434B true CN106565434B (zh) 2020-02-14

Family

ID=58536078

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201610963975.3A Active CN106565434B (zh) 2016-10-28 2016-10-28 一种蒽类化合物及其制备方法以及有机发光器件

Country Status (1)

Country Link
CN (1) CN106565434B (zh)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107400508B (zh) * 2017-07-06 2020-07-28 西安交通大学 一种非对称9,9′-联蒽类蓝光、主体材料及应用
CN112979400B (zh) * 2021-02-21 2023-06-06 苏州大学 一种在碱金属氢化物作用下制备2-碘代芳醚的方法
CN112979497A (zh) * 2021-02-21 2021-06-18 苏州大学 一种无催化剂下基于邻卤碘苯制备2-碘代芳醚的方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0681019A2 (en) * 1994-04-26 1995-11-08 TDK Corporation Phenylanthracene derivative and organic EL element
JP2007238500A (ja) * 2006-03-08 2007-09-20 Mitsui Chemicals Inc アントラセン化合物および該化合物を含有する有機電界発光素子

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100480424B1 (ko) * 2000-08-10 2005-04-07 미쯔이카가쿠 가부시기가이샤 탄화수소화합물, 유기전계발광소자용 재료 및유기전계발광소자
KR20160099157A (ko) * 2015-02-11 2016-08-22 삼성디스플레이 주식회사 유기 발광 소자

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0681019A2 (en) * 1994-04-26 1995-11-08 TDK Corporation Phenylanthracene derivative and organic EL element
JP2007238500A (ja) * 2006-03-08 2007-09-20 Mitsui Chemicals Inc アントラセン化合物および該化合物を含有する有機電界発光素子

Also Published As

Publication number Publication date
CN106565434A (zh) 2017-04-19

Similar Documents

Publication Publication Date Title
KR101467039B1 (ko) 유기 발광 소자용 화합물 및 이를 사용하는 유기 발광 소자
CN104995195B (zh) 杂环化合物、使用了其的有机电致发光元件用材料、以及使用了其的有机电致发光元件及电子设备
CN110229071A (zh) 芴衍生物有机电致发光器件
KR20130024521A (ko) 유기전기소자용 신규 화합물, 이를 이용하는 유기전기소자 및 그 전자 장치
CN105693631A (zh) 一种芳杂环化合物及其制备方法以及一种有机电致发光器件
CN114853769B (zh) 一种咔唑衍生物、有机电致发光元件、显示装置和照明装置
CN109336782B (zh) 一种芴类衍生物及其有机电致发光器件
CN108847447B (zh) 一种顶部发射有机电致发光器件
CN106543123A (zh) 一种联蒽类化合物及其制备方法以及有机发光器件
CN106565434B (zh) 一种蒽类化合物及其制备方法以及有机发光器件
CN110885335A (zh) 一种以苯并[1,2-b:4,5-b’]二苯并呋喃为核心的化合物及其应用
CN115073461A (zh) 一种咔唑衍生物及其在有机发光元件中的应用
CN108727389B (zh) 芘衍生物及其在有机发光材料中的应用
CN106892903B (zh) 基于酚嗪和咔唑的有机电致发光化合物及其发光器件
CN115093414A (zh) 一种咔唑衍生物及包含它的有机发光元件
CN113429399B (zh) 芘类衍生物，发光器件材料及发光器件
KR20130131793A (ko) 인돌 화합물 및 그 유도체를 포함하는 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
CN114539075A (zh) 一种芴衍生物及其应用
WO2021103728A1 (zh) 一种有机化合物和使用该化合物的有机电致发光器件
CN107619406A (zh) 一种新的咔唑类衍生物及其制备方法和在器件中的应用
CN115368370A (zh) 一种稠合氮杂环化合物及其应用以及包含该化合物的有机电致发光器件
KR20130104451A (ko) 인돌로퀴녹살린 유도체를 포함하는 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
CN112125812B (zh) 一种化合物及其应用以及包含该化合物的器件
CN107827879B (zh) 一种可用于柔性显示的材料及其制备方法和有机电致发光器件
CN114891000B (zh) 一种吲哚衍生物、有机电致发光元件、显示装置和照明装置

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
GR01 Patent grant
GR01 Patent grant