CN110003019A - 一种以均苯为核心的高迁移率有机化合物及其应用 - Google Patents
一种以均苯为核心的高迁移率有机化合物及其应用 Download PDFInfo
- Publication number
- CN110003019A CN110003019A CN201910279263.3A CN201910279263A CN110003019A CN 110003019 A CN110003019 A CN 110003019A CN 201910279263 A CN201910279263 A CN 201910279263A CN 110003019 A CN110003019 A CN 110003019A
- Authority
- CN
- China
- Prior art keywords
- general formula
- expressed
- organic compound
- organic
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
-
- 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
- C07D209/88—Carbazoles; Hydrogenated carbazoles 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 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
- C07D213/60—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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
- C07D219/08—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
-
- 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
-
- 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
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- 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
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—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
- C09K2211/1088—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
-
- 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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
本发明涉及一种以均苯为核心的具有高迁移率的有机化合物及其应用,本发明提供的有机化合物以均苯为核心,连接芘支链,本发明有机化合物具有良好的热稳定性和较高的玻璃化温度,同时具有合适的HOMO能级,采用本发明提供的有机化合物的器件通过结构优化,可有效提升OLED器件的光电性能以及OLED器件的寿命。
Description
技术领域
本发明涉及半导体技术领域,尤其涉及一种以均苯为核心的具有高迁移率的有机化合物及其应用。
背景技术
有机电致发光(OLED:Organic Light Emission Diodes)器件技术既可以用来制造新型显示产品,也可以用于制作新型照明产品,有望替代现有的液晶显示和荧光灯照明,应用前景十分广泛。
OLED发光器件犹如三明治的结构,包括电极材料膜层以及夹在不同电极膜层之间的有机功能材料,各种不同功能材料根据用途相互叠加在一起共同组成OLED发光器件。OLED发光器件作为电流器件,当对其两端电极施加电压,并通过电场作用有机层功能材料膜层中的正负电荷时,正负电荷进一步在电子阻挡层中复合,即产生OLED电致发光。
目前对OLED发光器件提高性能的研究包括:降低器件的驱动电压、提高器件的发光效率、提高器件的使用寿命等。为了实现OLED器件的性能的不断提升,不但需要从OLED器件结构和制作工艺的创新,更需要OLED光电功能材料不断研究和创新,创制出更高性能的OLED功能材料。
为了制作高性能的OLED发光器件,要求各种有机功能材料具备良好的光电性能,譬如,作为电荷传输材料,要求具有良好的载流子迁移率,高玻璃化转化温度等,作为电子阻挡层的主体材料具有良好双极性,适当的HOMO/LUMO能阶等。
因此,针对当前OLED器件的产业应用要求以及OLED器件的不同功能膜层,器件的光电特性需求,必须选择更适合、性能更高的OLED功能材料或材料组合,才能实现器件的高效率、长寿命和低电压的综合特性。就当前的OLED显示照明产业的实际需求而言,目前OLED材料的发展还远远不够,落后于面板制造企业的要求,作为材料企业开发更高性能的有机功能材料显得尤为重要。
发明内容
本发明的目的之一,是提供一种以均苯为核心的具有高迁移率的有机化合物,其具有良好的热稳定性和较高的玻璃化温度,同时具有合适的HOMO能级,采用本发明提供的有机化合物的器件通过结构优化,可有效提升OLED器件的光电性能以及OLED器件的寿命。
本发明解决上述技术问题的的技术方案如下:一种以均苯为核心的具有高迁移率的有机化合物,所述有机化合物的结构如通式(1)所示:
通式(1)中,Ar1-Ar5分别表示为取代的或未取代的C6-C30芳基、取代的或未取代的C2-C30杂芳基;
所述“取代的”是指至少一个氢原子由以下取代基来替代:金刚烷基、氰基、氟原子、甲基、乙基、丙基、异丙基、叔丁基、戊基、苯基、萘基、联苯基、吡啶基、二苯并呋喃基、咔唑基或呋喃基;
所述杂芳基中的杂原子任选自氮、氧或硫中的一种或多种。
作为本发明的进一步改进,所述Ar1、Ar2、Ar3、Ar4、Ar5分别表示为通式(2)、通式(3)、通式(4)或通式(5)所示结构:
通式(2)中,X1和X2分别独立的表示为单键、O、S、-C(R1R2)-或-NR3-,且X1和X2不同时表示为单键;
R1、R2、R3分别独立地表示为C1-C10的烷基、C3-C10的环烷基、C6-C30芳基、C2-C30杂芳基;
通式(2)、通式(3)、通式(4)、通式(5)和通式(6)中,Y表示为氮原子、碳原子或C-R4,Y每次出现相同或者不同,与其它基团键合时,Y表示为C;R4表示为氢原子、卤素原子、氰基、C1-C20的烷基、C3-C20的环烷基、C1-C20的烷氧基、C6-C30芳基、C2-C30杂芳基。
作为本发明的进一步改进,所述Ar1、Ar2、Ar3、Ar4、Ar5至少有一个表示为通式(2)或通式(3)所示结构。
作为本发明的进一步改进,R1、R2、R3分别独立地表示为甲基、异丙基、叔丁基、金刚烷基、苯基、联苯基、萘基、二甲基芴基、二苯并呋喃基、咔唑基、二苯并噻吩基、吡啶基、萘啶基或咔唑啉基;所述R4表示为为氢原子、氟原子、氰基、甲氧基、甲基、异丙基、叔丁基、金刚烷基、苯基、联苯基、萘基、二甲基芴基、二苯基芴基、螺芴基、二苯并呋喃基、咔唑基、二苯并噻吩基、吡啶基、萘啶基或咔唑啉基。
作为本发明的进一步改进,所述有机化合物的具体结构表示为以下结构中的任一种:
中的任一种。
本发明的目的之二,是提供上述有机化合物的制备方法。本发明的制备方法简单,市场前景广阔,适合规模化生产。
本发明解决上述技术问题的技术方案如下:一种均苯为核心的有机化合物的制备方法,所述制备方法涉及的反应方程式为:
具体制备方法如下:250mL的三口瓶,在通入氮气的气氛下,加入中间体C、原料D、叔丁醇钾、Pd2(dba)3、三苯基膦及150mL溶剂甲苯,加热回流12小时,取样点板,反应完全;自然冷却,过滤,滤液旋蒸,过硅胶柱,得到目标产物;
其中,所述原料D和中间体C的摩尔比为(1.0-3.0):1,叔丁醇钾与中间体C的摩尔比为(1-5):1,Pd2(dba)3与中间体C的摩尔比为(0.01-0.03):1,三苯基膦与中间体C摩尔比为(0.01-0.03):1;甲苯的用量为每1mol中间体C用(100-150)mL甲苯。
本发明的第三个方面是提供一种有机电致发光器件,包括阴极和阳极,所述阴极和阳极之间设置有有机功能层,具有这样的特征,上述有机功能层含有上述有机化合物。
作为本发明的进一步改进,所述有机功能层包括空穴传输层或电子阻挡层,具有这样的特征,上述空穴传输层或电子阻挡层含有上述有机化合物。
本发明的第五个方面是提供一种照明或显示元件,具有这样的特征,包括上述的有机电致发光器件。
本发明有益的技术效果在于:
1.本发明的有机化合物的结构使得电子和空穴在电子阻挡层的分布更加平衡,在恰当的HOMO能级下,提升了空穴注入和传输性能;在合适的LUMO能级下,又起到了电子阻挡的作用,提升激子在电子阻挡层中的复合效率;作为OLED发光器件的电子阻挡层材料使用时,可有效提高激子利用率和荧光辐射效率,降低高电流密度下的效率滚降,降低器件电压,提高器件的电流效率和寿命。
2.本发明的有机化合物在OLED器件应用时,通过器件结构优化,可保持高的膜层稳定性,可有效提升OLED器件的光电性能以及OLED器件的寿命。本发明所述化合物在OLED发光器件中具有良好的应用效果和产业化前景。
附图说明
图1为本发明所列举的材料应用于OLED器件的结构示意图;其中,1、透明基板层,2、ITO阳极层,3、空穴注入层,4、空穴传输层5、电子阻挡层,6、电子阻挡层,7、空穴阻挡/电子传输层,8、电子注入层,9、阴极层,10、CPL层。
图2为本发明制备的器件和对比器件在不同温度下测量的效率曲线图。
具体实施方式
下面将结合本发明实施例中的附图,对本发明实施例中的技术方案进行清楚、完整地描述。
下述制备实施例中所有原料均采购于烟台万润精细化工股份有限公司。
具体制备方法如下:250ml的三口瓶,在通入氮气的气氛下,加入0.01mol原料A1,0.014mol的原料B1,0.03mol叔丁醇钾,1.4×10-4mol Pd2(dba)3,1.3×10-4mol三苯基膦,150ml甲苯,加热至100℃回流12小时,取样点板,反应完全;自然冷却,过滤,滤液旋蒸,过硅胶柱,得到中间体C1;HPLC纯度98.6%,收率86.5%;元素分析结构(分子式C36H29N3):理论值C,85.85;H,5.80;N,8.34;测试值:C,85.87;H,5.81;N,8.34。ESI-MS(m/z)(M+):理论值为503.24,实测值为503.25。
以中间体C1的合成方法制备中间体C,其中涉及到原料A和原料B具体结构如表1所示。
表1
制备实施例1:化合物1的合成:
具体制备方法如下:250ml的三口瓶,在通入氮气的气氛下,加入0.01mol的中间体C1,加入0.014mol原料D1,0.03mol叔丁醇钾,1.4×10-4mol Pd2(dba)3,1.3×10-4mol三苯基膦,150ml甲苯,加热至110℃回流12小时,取样点板,反应完全;自然冷却,过滤,滤液旋蒸,过硅胶柱,得到化合物1;HPLC纯度99.2%,收率89.1%;元素分析结构(分子式C52H37N3):理论值C,88.73;H,5.30;N,5.97;测试值:C,88.74;H,5.30;N,5.97。
ESI-MS(m/z)(M+):理论值为703.30,实测值为703.32。
其余目标化合物的涉及到的反应类型和化合物1的制备步骤涉及到的反应类型相同。
制备实施例2:化合物3的合成
制备实施例3:化合物6的合成
制备实施例4:化合物7的合成
制备实施例5:化合物10的合成
制备实施例6:化合物12的合成
制备实施例7:化合物15的合成
制备实施例8:化合物22的合成
制备实施例9:化合物31的合成
制备实施例10:化合物37的合成
制备实施例11:化合物51的合成
制备实施例12:化合物58的合成
制备实施例13:化合物74的合成
制备实施例14:化合物87的合成
制备实施例15:化合物102的合成
目标化合物制备过程中涉及到的反应物和催化剂的量,以及得到的目标化合物的结构表征如表2所示。
表2
本发明有机化合物在发光器件中使用,具有高的玻璃化转变温度(Tg)和三线态能级(T1),合适的HOMO、LUMO能级,可以作为空穴传输层和电子阻挡层材料使用。对本发明化合物分别进行热性能、T1能级、HOMO能级、空穴迁移率及Eg测试,结果如表3所示。
表3
注:三线态能级T1是由日立的F4600荧光光谱仪测试,材料的测试条件为2*10- 5mol/L的甲苯溶液;玻璃化温度Tg由示差扫描量热法(DSC,德国耐驰公司DSC204F1示差扫描量热仪)测定,升温速率10℃/min;最高占据分子轨道HOMO能级是由电离能测试***(IPS-3)以及紫外分光光度计(UV)测试计算所得,测试为大气环境,空穴迁移率测试,将本发明材料制成单电荷器件,用SCLC方法测定;Eg能级:基于材料单膜的紫外分光光度(UV吸收)基线与第一吸收峰的上升侧画切线,用切线和基线交叉点数值算出;同时,可以使用Gaussian16、6-31G(d)基组,B3lyp泛函、TD-FDT算法优化几何结构,进行HOMO、LUMO能级计算,Eg=|HOMO-LUMO|。
由上表数据可知,本发明化合物具有适当的HOMO能级、Eg以及较高的空穴迁移率,适合作为空穴传输层和电子阻挡层材料;同时,本发明化合物具有较高的热稳定性,使得应用本发明化合物的OLED器件寿命得到提升。
以下通过器件实施例1~37和比较例1详细说明本发明合成的化合物在器件中作为空穴传输层和电子阻挡层的应用效果。器件实施例2~37、器件比较例1与器件实施例1相比,所述器件的制作工艺完全相同,并且所采用了相同的基板材料和电极材料,电极材料的膜厚也保持一致,所不同的是器件实施例2~17中空穴传输层的材料发生了改变;器件实施例18~37中对器件的电子阻挡层材料做了变换,各实施例所得器件的结构如表4所示。
器件实施例1
如图1所示,一种电致发光器件的制备方法,包括如下步骤:
透明基板层1为透明PI膜,对ITO阳极层2(膜厚为150nm)进行洗涤,即依次进行碱洗涤、纯水洗涤、干燥,再进行紫外线-臭氧洗涤以清除透明ITO表面的有机残留物。在进行了上述洗涤之后的ITO阳极层2上,利用真空蒸镀装置,蒸镀膜厚为10nm的HAT-CN作为空穴注入层3使用。接着蒸镀60nm厚度的化合物1作为空穴传输层。随后蒸镀20nm厚度的EB-1作为电子阻挡层。然后制作OLED发光器件的发光层6,其结构包括OLED发光层6所使用GH-1、GH-2作为主体材料,GD-1作为掺杂材料,掺杂材料掺杂比例为10%重量比,发光层膜厚为40nm。在上述发光层6之后,继续真空蒸镀电子传输层材料为ET-1和Liq。该材料的真空蒸镀膜厚为30nm,此层为空穴阻挡/电子传输层7。在空穴阻挡/电子传输层7上,通过真空蒸镀装置,制作膜厚为1nm的氟化锂(LiF)层,此层为电子注入层8。在电子注入层8上,通过真空蒸镀装置,制作膜厚为15nm的Mg:Ag电极层,此层为阴极层9使用。在阴极层9上,真空蒸镀70nm的CP-1,作为CPL层10。
相关现有材料的结构如下所示:
如上所述地完成OLED发光器件后,用公知的驱动电路将阳极和阴极连接起来,测量器件的电流效率、发光光谱以及器件的寿命。所得器件的测试结果见表5示。
表4
表5
说明:器件测试性能以比较例1作为参照;电流效率均在10mA/cm2条件下测得;寿命测试***为日本System Engineer's Co.,LTD开发的型号为EAS-62C的OLED器件寿命测试仪。
表5的结果表明本发明化合物作为空穴传输层和电子阻挡层材料可应用于OLED发光器件制作,并且与比较例1相比,无论是效率还是寿命均比已知OLED材料获得较大改观,特别是器件的驱动寿命获得较大的提升。
进一步的本发明材料制备的OLED器件在低温下工作时效率也比较稳定,将器件实施例1、8、18和器件比较例1在-10~80℃区间进行效率测试,所得结果如表6和图2所示。
表6
从表6的数据可知,实施例1、8、18为本发明材料和已知材料搭配的器件结构,和器件比较例1相比,不仅低温效率高,而且在温度升高过程中,效率平稳升高。
从以上数据应用来看,本发明化合物作为空穴传输层或电子阻挡层材料在OLED发光器件中具有良好的应用效果,具有良好的产业化前景。
Claims (7)
1.一种以均苯为核心的具有高迁移率的有机化合物,其特征在于,所述有机化合物的结构如通式(1)所示:
通式(1)中,Ar1-Ar5分别表示为取代的或未取代的C6-C30芳基、取代的或未取代的C2-C30杂芳基;
所述“取代的”是指至少一个氢原子由以下取代基来替代:金刚烷基、氰基、氟原子、甲基、乙基、丙基、异丙基、叔丁基、戊基、苯基、萘基、联苯基、吡啶基、二苯并呋喃基、咔唑基或呋喃基;
所述杂芳基中的杂原子任选自氮、氧或硫中的一种或多种。
2.根据权利要求1所述的有机化合物,其特征在于,所述Ar1、Ar2、Ar3、Ar4、Ar5分别表示为通式(2)、通式(3)、通式(4)或通式(5)所示结构:
通式(2)中,X1和X2分别独立的表示为单键、O、S、-C(R1R2)-或-NR3-,且X1和X2不同时表示为单键;
R1、R2、R3分别独立地表示为C1-C10的烷基、C3-C10的环烷基、C6-C30芳基、C2-C30杂芳基;
通式(2)、通式(3)、通式(4)、通式(5)和通式(6)中,Y表示为氮原子、碳原子或C-R4,Y每次出现相同或者不同,与其它基团键合时,Y表示为C;R4表示为氢原子、卤素原子、氰基、C1-C20的烷基、C3-C20的环烷基、C1-C20的烷氧基、C6-C30芳基、C2-C30杂芳基。
3.根据权利要求1所述的有机化合物,其特征在于,所述Ar1、Ar2、Ar3、Ar4、Ar5至少有一个表示为通式(2)或通式(3)所示结构。
4.根据权利要求1或2所述的有机化合物,其特征在于,所述R1、R2、R3分别独立地表示为甲基、异丙基、叔丁基、金刚烷基、苯基、联苯基、萘基、二甲基芴基、二苯并呋喃基、咔唑基、二苯并噻吩基、吡啶基、萘啶基或咔唑啉基;所述R4表示为为氢原子、氟原子、氰基、甲氧基、甲基、异丙基、叔丁基、金刚烷基、苯基、联苯基、萘基、二甲基芴基、二苯基芴基、螺芴基、二苯并呋喃基、咔唑基、二苯并噻吩基、吡啶基、萘啶基或咔唑啉基。
5.根据权利要求1所述的有机化合物,其特征在于,所述有机化合物的具体结构表示为以下结构中的任一种:
中的任一种。
6.一种有机电致发光器件,包括阴极和阳极,所述阴极和阳极之间设置有有机功能层,其特征在于,所述有机功能层包含有权利要求1-5任一项所述的有机化合物。
7.根据权利要求5所述的一种有机电致发光器件,所述有机功能层包括电子阻挡层或空穴传输层,其特征在于,所述电子阻挡层或空穴传输层含有权利要求1-5任一项所述的有机化合物。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910279263.3A CN110003019B (zh) | 2019-04-09 | 2019-04-09 | 一种以均苯为核心的高迁移率有机化合物及其应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910279263.3A CN110003019B (zh) | 2019-04-09 | 2019-04-09 | 一种以均苯为核心的高迁移率有机化合物及其应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN110003019A true CN110003019A (zh) | 2019-07-12 |
CN110003019B CN110003019B (zh) | 2022-08-16 |
Family
ID=67170435
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201910279263.3A Active CN110003019B (zh) | 2019-04-09 | 2019-04-09 | 一种以均苯为核心的高迁移率有机化合物及其应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN110003019B (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2020253445A1 (zh) * | 2019-06-19 | 2020-12-24 | 陕西莱特光电材料股份有限公司 | 一种有机电致发光材料及包含该材料的有机电致发光器件 |
CN115385802A (zh) * | 2022-06-17 | 2022-11-25 | 长春海谱润斯科技股份有限公司 | 一种有机电致发光器件 |
Citations (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0689040A (ja) * | 1992-09-07 | 1994-03-29 | Ricoh Co Ltd | 電子写真用感光体 |
EP0611148A1 (en) * | 1993-02-10 | 1994-08-17 | Yasuhiko Shirota | Trisarylaminobenzene derivatives, compounds for organic EL element, and organic EL element |
JPH06240248A (ja) * | 1993-02-18 | 1994-08-30 | Ricoh Co Ltd | 電界発光素子 |
JPH07157754A (ja) * | 1993-10-14 | 1995-06-20 | Ricoh Co Ltd | 電界発光素子 |
JPH07271068A (ja) * | 1994-03-31 | 1995-10-20 | Mita Ind Co Ltd | 積層型電子写真感光体 |
JPH0848974A (ja) * | 1994-08-09 | 1996-02-20 | Yasuhiko Shirota | 有機el素子 |
JPH09208845A (ja) * | 1996-02-05 | 1997-08-12 | Toyo Ink Mfg Co Ltd | 蛍光着色剤 |
DE19704031A1 (de) * | 1997-02-04 | 1998-08-06 | Bosch Gmbh Robert | Aminoverbindung und elektrolumineszierende Anordnung mit einer lochleitenden Schicht jene enthaltend |
EP0977087A1 (en) * | 1998-07-31 | 2000-02-02 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member, process cartridge and electrophotographic apparatus |
JP2003040844A (ja) * | 2001-07-30 | 2003-02-13 | Konica Corp | 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子材料及びそれ等に用いる化合物 |
JP2004006379A (ja) * | 2003-06-20 | 2004-01-08 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子 |
CN101410476A (zh) * | 2006-03-24 | 2009-04-15 | 默克专利有限公司 | 用于有机电致发光器件的新型材料 |
US20140030644A1 (en) * | 2012-07-27 | 2014-01-30 | Ricoh Company, Ltd. | Image bearing member and image forming apparatus |
US20140209878A1 (en) * | 2013-01-30 | 2014-07-31 | Samsung Display Co., Ltd. | Amine-based compound and organic light emitting diode comprising the same |
CN104356004A (zh) * | 2014-10-23 | 2015-02-18 | 江苏三月光电科技有限公司 | 一种新型芳香类化合物的合成及其在oled器件上的应用 |
CN104370752A (zh) * | 2014-10-23 | 2015-02-25 | 江苏三月光电科技有限公司 | 一种1,3,5-三(芳基胺基)苯芳香类化合物的合成及其在oled器件上的应用 |
WO2016034556A2 (de) * | 2014-09-02 | 2016-03-10 | Cynora Gmbh | Opto-elektronische vorrichtung enthaltend emitterverbindung mit hoher quantenausbeute und löslichkeit |
CN106892887A (zh) * | 2017-03-17 | 2017-06-27 | 吉林奥来德光电材料股份有限公司 | 一种化合物及其制备方法和应用 |
CN109535012A (zh) * | 2018-12-17 | 2019-03-29 | 长春海谱润斯科技有限公司 | 一种有机电致发光器件 |
-
2019
- 2019-04-09 CN CN201910279263.3A patent/CN110003019B/zh active Active
Patent Citations (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0689040A (ja) * | 1992-09-07 | 1994-03-29 | Ricoh Co Ltd | 電子写真用感光体 |
EP0611148A1 (en) * | 1993-02-10 | 1994-08-17 | Yasuhiko Shirota | Trisarylaminobenzene derivatives, compounds for organic EL element, and organic EL element |
JPH06240248A (ja) * | 1993-02-18 | 1994-08-30 | Ricoh Co Ltd | 電界発光素子 |
JPH07157754A (ja) * | 1993-10-14 | 1995-06-20 | Ricoh Co Ltd | 電界発光素子 |
JPH07271068A (ja) * | 1994-03-31 | 1995-10-20 | Mita Ind Co Ltd | 積層型電子写真感光体 |
JPH0848974A (ja) * | 1994-08-09 | 1996-02-20 | Yasuhiko Shirota | 有機el素子 |
JPH09208845A (ja) * | 1996-02-05 | 1997-08-12 | Toyo Ink Mfg Co Ltd | 蛍光着色剤 |
DE19704031A1 (de) * | 1997-02-04 | 1998-08-06 | Bosch Gmbh Robert | Aminoverbindung und elektrolumineszierende Anordnung mit einer lochleitenden Schicht jene enthaltend |
EP0977087A1 (en) * | 1998-07-31 | 2000-02-02 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member, process cartridge and electrophotographic apparatus |
JP2003040844A (ja) * | 2001-07-30 | 2003-02-13 | Konica Corp | 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子材料及びそれ等に用いる化合物 |
JP2004006379A (ja) * | 2003-06-20 | 2004-01-08 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子 |
CN101410476A (zh) * | 2006-03-24 | 2009-04-15 | 默克专利有限公司 | 用于有机电致发光器件的新型材料 |
US20140030644A1 (en) * | 2012-07-27 | 2014-01-30 | Ricoh Company, Ltd. | Image bearing member and image forming apparatus |
US20140209878A1 (en) * | 2013-01-30 | 2014-07-31 | Samsung Display Co., Ltd. | Amine-based compound and organic light emitting diode comprising the same |
WO2016034556A2 (de) * | 2014-09-02 | 2016-03-10 | Cynora Gmbh | Opto-elektronische vorrichtung enthaltend emitterverbindung mit hoher quantenausbeute und löslichkeit |
CN104356004A (zh) * | 2014-10-23 | 2015-02-18 | 江苏三月光电科技有限公司 | 一种新型芳香类化合物的合成及其在oled器件上的应用 |
CN104370752A (zh) * | 2014-10-23 | 2015-02-25 | 江苏三月光电科技有限公司 | 一种1,3,5-三(芳基胺基)苯芳香类化合物的合成及其在oled器件上的应用 |
CN106892887A (zh) * | 2017-03-17 | 2017-06-27 | 吉林奥来德光电材料股份有限公司 | 一种化合物及其制备方法和应用 |
CN109535012A (zh) * | 2018-12-17 | 2019-03-29 | 长春海谱润斯科技有限公司 | 一种有机电致发光器件 |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2020253445A1 (zh) * | 2019-06-19 | 2020-12-24 | 陕西莱特光电材料股份有限公司 | 一种有机电致发光材料及包含该材料的有机电致发光器件 |
US11424412B2 (en) | 2019-06-19 | 2022-08-23 | Shaanxi Lighte Optoelectronics Material Co., Ltd. | Organic electroluminescent material and organic electroluminescent device comprising same |
CN115385802A (zh) * | 2022-06-17 | 2022-11-25 | 长春海谱润斯科技股份有限公司 | 一种有机电致发光器件 |
Also Published As
Publication number | Publication date |
---|---|
CN110003019B (zh) | 2022-08-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN106467549B (zh) | 一种含有苯并咪唑的化合物及其在有机电致发光器件上的应用 | |
CN110156612A (zh) | 一种具有高迁移率的有机化合物及其应用 | |
CN110317184A (zh) | 一种基于双二甲基芴的化合物、制备方法及其应用 | |
CN109467543A (zh) | 一种三芳胺衍生物及其有机电致发光器件 | |
CN109942439A (zh) | 一种三芳胺类有机化合物及其应用 | |
CN105837498B (zh) | 一种含有二甲基蒽结构的有机化合物及其应用 | |
CN109836339A (zh) | 一种三芳胺类有机化合物及其应用 | |
CN110229145A (zh) | 一种基于氮杂苯的有机化合物及其在oled上的应用 | |
CN106220619B (zh) | 一种含有氧杂蒽结构的有机化合物及其应用 | |
CN109912431A (zh) | 一种含萘的三芳胺类有机化合物及其应用 | |
CN109928911A (zh) | 一种含有三芳胺和咔唑的有机化合物及其应用 | |
CN109928886A (zh) | 一种含有三芳胺和芴的化合物及其应用 | |
CN107057681A (zh) | 一种含有氧杂蒽结构的光电材料及其在oled领域的应用 | |
CN109956962A (zh) | 一种以氮杂螺芴结构为母核的化合物及其在有机电致发光器件上的应用 | |
CN110003091A (zh) | 一种含有三芳胺和咔唑的化合物及其应用 | |
CN109574858A (zh) | 一种螺二甲基蒽芴类有机化合物及其在有机电致发光器件上的应用 | |
CN108203417A (zh) | 以芴为主体的有机化合物及有机电致发光器件 | |
CN107586299A (zh) | 一种以氮杂苯为核心的有机化合物及其应用 | |
CN111662190A (zh) | 一种含芘或氮杂芘的有机化合物及其应用 | |
CN110323342A (zh) | 一种有机电致发光器件及显示元件 | |
CN110003019A (zh) | 一种以均苯为核心的高迁移率有机化合物及其应用 | |
CN109575039A (zh) | 一种氮杂苯类有机化合物及其应用 | |
CN107759559A (zh) | 化合物及其有机电子装置 | |
CN108218853A (zh) | 一种以二苯并含氮六元杂环为核心的化合物及其在有机电致发光器件上的应用 | |
CN110294735A (zh) | 一种以蒽和菲为核心的化合物及其在有机电致发光器件上的应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
CB02 | Change of applicant information |
Address after: 214112 No. 210, Xinzhou Road, New District, Wuxi City, Jiangsu Province Applicant after: Jiangsu March Technology Co.,Ltd. Address before: 214112 No. 210, Xinzhou Road, New District, Wuxi City, Jiangsu Province Applicant before: JIANGSU SUNERA TECHNOLOGY Co.,Ltd. |
|
CB02 | Change of applicant information | ||
GR01 | Patent grant | ||
GR01 | Patent grant |