CN110452226B - 一种基于吡咯衍生物的有机蓝光荧光材料与蓝光器件 - Google Patents

一种基于吡咯衍生物的有机蓝光荧光材料与蓝光器件 Download PDF

Info

Publication number
CN110452226B
CN110452226B CN201910717048.7A CN201910717048A CN110452226B CN 110452226 B CN110452226 B CN 110452226B CN 201910717048 A CN201910717048 A CN 201910717048A CN 110452226 B CN110452226 B CN 110452226B
Authority
CN
China
Prior art keywords
blue light
light
organic
fluorescent material
blue
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
CN201910717048.7A
Other languages
English (en)
Other versions
CN110452226A (zh
Inventor
孟鸿
施明
孙越
贺耀武
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.)
Peking University Shenzhen Graduate School
Original Assignee
Peking University Shenzhen Graduate School
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 Peking University Shenzhen Graduate School filed Critical Peking University Shenzhen Graduate School
Priority to CN201910717048.7A priority Critical patent/CN110452226B/zh
Publication of CN110452226A publication Critical patent/CN110452226A/zh
Application granted granted Critical
Publication of CN110452226B publication Critical patent/CN110452226B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • 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
    • C07D401/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D413/14—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
    • 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
    • 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
    • C07D471/22—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 systems contains four or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/06—Peri-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
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • 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
    • 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
    • H10K85/649—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
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • H10K85/6565—Oxadiazole compounds
    • 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
    • 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
    • C09K2211/1044—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
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • 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

Landscapes

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

Abstract

本发明公开一种基于吡咯衍生物的有机蓝光荧光材料与蓝光器件，所述有机蓝光荧光材料包括D‑A结构，所述D为电子供体，所述A为电子受体，所述D为吡咯衍生物。本发明提供一类基于吡咯衍生物作为电子供体的有机蓝光荧光材料，基于该材料的蓝光器件的光色纯度具有很好的蓝光荧光效果。同时，基于该材料的蓝光器件具有高的发光纯度、发光效率和器件稳定性；此外由于材料自身的特点，可以精简器件结构，降低器件制备复杂度。

Description

一种基于吡咯衍生物的有机蓝光荧光材料与蓝光器件
技术领域
本发明涉及有机光电材料领域，尤其涉及一种基于吡咯衍生物的有机蓝光荧光材料与蓝光器件。
背景技术
有机电致发光二极管(OLED)是指有机材料在电场作用下，受到电流或电场的激发而产生光的新一代显示技术。基于有机电致发光材料的OLED显示技术，在智能手机、电视、照明、大屏显示等领域已取得成功的应用，其柔性显示、质量轻薄、响应快速、高纯显色、主动发光且能耗低等优势，收到了学术界和工业界的广泛重视和研究。根据光的三原色，有机发光材料可以分为蓝色、红色和绿色三种发光材料，目前的白光显示中最大的瓶颈就是蓝光材料和器件，尤其是浅蓝色到深蓝色的高性能蓝光材料。从材料本身来分析，蓝光的能隙间隔要求在2.7eV以上，给材料的综合性能的设计带来挑战；器件上分子，宽的带隙对功能层之间的能级匹配也提出了高的要求。所以设计和开发出一系列高荧光量子产率和高稳定性的蓝光材料十分必要，同时其它层的设计和匹配也同等重要。
自从有机发光二极管(OLED)被发现以来，有机小分子蓝光材料和蓝光器件持续取得了进展，在发光效率和稳定性上面都有了很大的提高。有机磷光蓝光材料由于需要贵金属(Ir、Pt等)，而且器件的稳定性和发光纯度都有很大的困难，有机荧光蓝光材料更有优势。荧光材料按照发光的过程可以分为普通荧光和延迟荧光。普通荧光就是单线态上的25％的单线态激子直接跃迁回基态所发射的荧光，这类荧光材料的理论最大内部量子效率为25％，如果外部光量子耦合效率为0.2，它的最大外部发光效率为5％，这远远不能满足商业的需求，虽然它的稳定性和光色纯度十分出色；另一类就是延迟荧光材料，目前根据延迟发光机理不同分为三种：热激发延迟荧光(TADF)、三线态-三线态激子湮灭延迟荧光(TTA)和高线态逆转换延迟荧光(HLCT)。目前研究最多也是效果最好的就是TADF蓝光材料，由于热激发下三线态激子可以逆转换单线态，从而内部量子效率可以实现100％，这类延迟荧光材料在发光效率上和传统荧光相比取得了巨大的突破。但是基于TADF材料的蓝光器件的光色纯度很难达到纯蓝或者深蓝，这是因为TADF发光材料由于D-A结构存在较强电荷转移态，在光谱上则表现为半峰宽很宽，一般都在90nm左右。
因此，现有技术还有待于改进和发展。
发明内容
鉴于上述现有技术的不足，本发明的目的在于提供一种基于吡咯衍生物的有机蓝光荧光材料与蓝光器件，旨在解决现有基于TADF材料的蓝光器件的光色纯度很难达到纯蓝或者深蓝的问题。
本发明的技术方案如下：
本发明提供一种基于吡咯衍生物的有机蓝光荧光材料，其中，包括D-A结构，所述D为电子供体，所述A为电子受体，所述D为吡咯衍生物。
本发明提供一种蓝光器件，包括发光层，其中，所述发光层的材料包括本发明所述的有机蓝光荧光材料。
有益效果：本发明提供一类基于吡咯衍生物作为电子供体的有机蓝光荧光材料，基于该材料的蓝光器件的光色纯度具有很好的蓝光荧光效果。同时，基于该材料的蓝光器件具有高的发光纯度、发光效率和器件稳定性；此外由于材料自身的特点，可以精简器件结构，降低器件制备复杂度。
附图说明
图1为本发明具体的实施例中化合物1作为发光层的器件的结构示意图。
图2为本发明具体的实施例中化合物1作为发光层的器件的外量子效率图。
图3为本发明具体的实施例中化合物1作为发光层的器件的电致发光图。
具体实施方式
本发明提供一种基于吡咯衍生物的有机蓝光荧光材料与蓝光器件，为使本发明的目的、技术方案及效果更加清楚、明确，以下对本发明进一步详细说明。应当理解，此处所描述的具体实施例仅仅用以解释本发明，并不用于限定本发明。
为了实现纯蓝或者深蓝，必须设计出新的电子供体和新的电子受体，目前最常用的蓝光材料的电子供体为咔唑及其衍生物，为了减小电荷转移态，本实施例设计具备更弱供电子能力的基团。研究发现，基于结构的修饰，基于吡咯和吡咯衍生物的基团的供电子能力比咔唑弱，同时具有很强的荧光，是一类十分有潜力应用于蓝光和深蓝光OLED材料研究的体系。因此，本发明基于吡咯衍生物作电子供体，设计了一系列的新型蓝光荧光材料。
具体的，本发明实施例提供一种基于吡咯衍生物的有机蓝光荧光材料，其中，包括D-A结构，所述D为电子供体，所述A为电子受体，所述D为吡咯衍生物。
也就是说，本发明实施例材料结构模型为：D-A(Donor-Acceptor)。其中D(Donor，供体)选择的是吡咯衍生物，这是一类极易修饰，具有良好的空穴传输能力和弱供电子能力的基团。
在一种实施方式中，所述A(Acceptor，受体)为含氮杂环；或者
所述A为含硼、酮或砜等具有吸电子特性的芳香基团。
通过计算和测试，本实施例所述材料的带隙在2.80eV以上，而且都具备很好的蓝光荧光。当作为发光材料的时候，由于自身的双极性特性，以及吡咯衍生物结构的空间扭曲性和聚集诱导发光效应，可以有效的减缓分子间的激子猝灭，因为可用于掺杂和非掺杂蓝光器件。
在一种实施方式中，所述D为一类基于2,3,4,5-四芳基取代吡咯，所述D的结构式如下式所示：
Figure BDA0002155783490000041
R1、R2、R3、R4分别独立地选自以下中的一种:
Figure BDA0002155783490000042
Figure BDA0002155783490000043
Figure BDA0002155783490000044
2，5位为吡咯芳环上较为活泼的位点，用芳基加以保护，可以提高基团的稳定性；3，4位连接为芳香基团时，会具有聚集诱导发光性质，或为稠环时，可以增强共轭，提高发光效率。
在一种实施方式中，所述电子受体选自以下基团中的一种:
Figure BDA0002155783490000045
Figure BDA0002155783490000051
在一种实施方式中，所述材料选自如下化合物1-116中的任意一种：
Figure BDA0002155783490000061
Figure BDA0002155783490000071
Figure BDA0002155783490000081
Figure BDA0002155783490000091
Figure BDA0002155783490000101
Figure BDA0002155783490000111
Figure BDA0002155783490000121
Figure BDA0002155783490000131
Figure BDA0002155783490000141
Figure BDA0002155783490000151
Figure BDA0002155783490000161
Figure BDA0002155783490000171
Figure BDA0002155783490000181
Figure BDA0002155783490000191
Figure BDA0002155783490000201
Figure BDA0002155783490000211
本发明实施例提供一种蓝光器件，包括发光层，其中，所述发光层的材料包括本发明实施例所述的有机蓝光荧光材料。
本发明实施例提供一种有机蓝光荧光材料的制备方法，其可通过Buchward偶联反应制备得到，采用本领域技术人员所熟知的常规反应条件即可。
下面以化合物1为例，对其制备方法进行介绍。简单吡咯衍生物原料和电子受体基团均易购买，反应式如下所示：
Figure BDA0002155783490000221
具体制备过程：氮气条件下向100ml1,4-二氧六环溶剂中加入2,3,4,5-四苯基吡咯(3.71g，10.0mmol)、4-溴三苯基三嗪(4.27g，11.0mmol)、三(二亚苄基丙酮)二钯(0.58g，0.5mmol)和三叔丁基磷(15％，0.15mmol)，110℃下搅拌12小时。反应冷却至室温后硅胶漏斗过滤，溶液低压浓缩后二氯甲烷和正己烷进行柱层析得到最终产物(5.77g，8.5mmol)，产率85％。
下面通过具体的实施例对本发明进一步说明。
实施例
以化合物1用作OLED的发光层材料为例，OLED器件结构如图1所示：
上述器件中所用到的所有材料除发光层材料外，均是商业化材料。ITO透明基板，用水、乙醇和丙酮分别超声30分钟，用氮气吹干备用。HATCN作为空穴注入层，其蒸镀速率为0.1A/S，厚度为5nm；LHT002作为第一空穴传输层，其蒸镀速率为0.8A/S，厚度为30nm；TAPC作为第二空穴传输层，同时由于其高三线态的原因，也用作激子阻挡层，蒸镀速率为0.8A/S，厚度为10nm；emitter(发光层)和DPEPO共蒸，掺杂浓度为5％或10％(％为质量百分比)，厚度为30nm；TmPyPB是第一电子传输层，其蒸镀速率为0.8A/S，厚度为40nm；LET003用作第二电子传输层，其蒸镀速率为0.8A/S，厚度为20nm；Liq用作电子注入层，其蒸镀速率为0.05A/S，厚度为2nm；Al用作电极，其蒸镀速率为1A/S，厚度为100nm。
Figure BDA0002155783490000231
Figure BDA0002155783490000241
结合图2-3所示，本实施例器件得到的最大EQE为9.11，测得的EL光谱，最高发光的位移为450nm，为深蓝光，发光CIE坐标为(0.14,0.12)。
综上所述，本发明提供一类基于吡咯衍生物作为电子供体的有机蓝光荧光材料，基于该材料的蓝光器件的光色纯度具有很好的蓝光荧光效果。同时，基于该材料的蓝光器件具有高的发光纯度、发光效率和器件稳定性；此外由于材料自身的特点，可以精简器件结构，降低器件制备复杂度。
应当理解的是，本发明的应用不限于上述的举例，对本领域普通技术人员来说，可以根据上述说明加以改进或变换，所有这些改进和变换都应属于本发明所附权利要求的保护范围。

Claims (2)

1.一种基于吡咯衍生物的有机蓝光荧光材料，其特征在于，所述有机蓝光荧光材料为
Figure FDA0003505153400000011
2.一种蓝光器件，包括发光层，其特征在于，所述发光层的材料包括权利要求1所述的基于吡咯衍生物的有机蓝光荧光材料。
CN201910717048.7A 2019-08-05 2019-08-05 一种基于吡咯衍生物的有机蓝光荧光材料与蓝光器件 Active CN110452226B (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201910717048.7A CN110452226B (zh) 2019-08-05 2019-08-05 一种基于吡咯衍生物的有机蓝光荧光材料与蓝光器件

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201910717048.7A CN110452226B (zh) 2019-08-05 2019-08-05 一种基于吡咯衍生物的有机蓝光荧光材料与蓝光器件

Publications (2)

Publication Number Publication Date
CN110452226A CN110452226A (zh) 2019-11-15
CN110452226B true CN110452226B (zh) 2022-04-22

Family

ID=68484875

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201910717048.7A Active CN110452226B (zh) 2019-08-05 2019-08-05 一种基于吡咯衍生物的有机蓝光荧光材料与蓝光器件

Country Status (1)

Country Link
CN (1) CN110452226B (zh)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112521411B (zh) * 2019-09-19 2024-04-12 北京鼎材科技有限公司 一种化合物及其应用
CN110981871B (zh) * 2019-12-11 2022-07-22 北京大学深圳研究生院 一种蓝光材料及其制备方法和应用
CN111440187B (zh) * 2019-12-11 2023-04-07 北京大学深圳研究生院 一种热激发延迟蓝光材料及其制备方法和应用
JP2021091644A (ja) * 2019-12-12 2021-06-17 学校法人関西学院 多量体化合物
KR20220156003A (ko) * 2020-03-18 2022-11-24 가부시키가이샤 큐럭스 화합물, 발광 재료 및 유기 발광 디바이스
KR20230122094A (ko) 2020-12-18 2023-08-22 메르크 파텐트 게엠베하 Oled에 사용하기 위한 청색 형광 방출체로서의 인돌로[3.2.1-jk]카르바졸-6-카르보니트릴유도체
KR20230122093A (ko) 2020-12-18 2023-08-22 메르크 파텐트 게엠베하 유기 전계 발광 디바이스용 질소 함유 화합물
CN113801057B (zh) * 2021-08-13 2023-04-18 浙江大学 䓛基氮杂[7]螺烯类化合物、制备方法及应用

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100482276B1 (ko) * 2002-08-12 2005-04-13 한국과학기술연구원 피롤계 화합물, 그 중합체 및 이들을 이용한 ｅｌ 소자
WO2009104733A1 (ja) * 2008-02-22 2009-08-27 東洋インキ製造株式会社 有機エレクトロルミネッセンス素子用材料ならびに有機エレクトロルミネッセンス素子
KR101562883B1 (ko) * 2013-10-11 2015-10-23 (주)피엔에이치테크 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자
KR20150045141A (ko) * 2013-10-18 2015-04-28 (주)피엔에이치테크 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자
KR101614583B1 (ko) * 2013-10-25 2016-04-21 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
CN103833507B (zh) * 2013-12-25 2016-08-17 石家庄诚志永华显示材料有限公司 一系列有机电致发光材料及其制备方法与应用
KR101666826B1 (ko) * 2014-05-29 2016-10-17 (주)피엔에이치테크 유기발광 화합물 및 이를 포함하는 유기전계발광소자
JP2016119355A (ja) * 2014-12-19 2016-06-30 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子

Also Published As

Publication number Publication date
CN110452226A (zh) 2019-11-15

Similar Documents

Publication Publication Date Title
CN110452226B (zh) 一种基于吡咯衍生物的有机蓝光荧光材料与蓝光器件
CN105503766B (zh) 一种热活化延迟荧光材料及有机电致发光器件
CN112174992B (zh) 一种发光材料及其应用以及包含其的有机电致发光器件
CN105418533B (zh) 一种红光热活化延迟荧光材料及有机电致发光器件
CN112480154A (zh) 一种手性热活化延迟荧光材料及其圆偏振电致发光器件
CN108250214B (zh) 氧杂螺芴三苯胺衍生物、制备方法及其用途
CN112979709B (zh) 一种金属配合物及其应用
CN111777633B (zh) 一种含硼化合物及含有其的有机电致发光器件
Jung et al. A new family of bis-DCM based dopants for red OLEDs
CN112341466A (zh) 一种有机化合物及使用该化合物的有机发光器件
CN112174942A (zh) 一种有机化合物及使用该化合物的有机发光器件
CN110964019B (zh) 一种以6-苯基-6H-吲哚并[2,3-b]喹喔啉为受体的化合物及其应用
CN113248485A (zh) 一种有机发光主体组合物及使用该组合物的有机发光器件
Zhou et al. Double light-emitting layer implementing three-color emission: Using DCJTB lightly doping in Alq3 as red-green emitting layer and APEAn1N as blue-green emitting layer
CN108191847B (zh) 一类不对称给受体型有机红色荧光小分子材料及其在有机电致发光器件中的应用
WO2021120450A1 (zh) 一种热活化延迟荧光绿光高分子材料及其制备方法
CN112341460A (zh) 一种有机化合物及使用该化合物的有机发光器件
CN110003115B (zh) 一种蓝色有机发光材料、发光器件及制备方法
WO2020220414A1 (zh) 热活化延迟荧光材料及其制备方法、显示装置
CN105237520A (zh) 一种含有吡唑啉结构的化合物材料及其应用
CN109988166A (zh) 一种以菲啶衍生物为受体的化合物及其应用
CN104860884A (zh) 类三苯基乙烯衍生物及其用途
CN112279844B (zh) 一种绿光主体材料、有机电致发光器件及电子显示设备
KR102509009B1 (ko) 보론 화합물 및 이를 포함하는 유기 발광 소자
CN110256458B (zh) 一种热活化延迟荧光分子及其制备方法、电致热激活延迟荧光器件

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