CN107721903A - 一种有机电致发光材料及其有机发光器件 - Google Patents

一种有机电致发光材料及其有机发光器件 Download PDF

Info

Publication number
CN107721903A
CN107721903A CN201711111257.4A CN201711111257A CN107721903A CN 107721903 A CN107721903 A CN 107721903A CN 201711111257 A CN201711111257 A CN 201711111257A CN 107721903 A CN107721903 A CN 107721903A
Authority
CN
China
Prior art keywords
unsubstituted
organic
substituted
compound
electroluminescent
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.)
Withdrawn
Application number
CN201711111257.4A
Other languages
English (en)
Inventor
孙可
孙可一
蔡辉
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Changchun Haipurunsi Technology Co Ltd
Original Assignee
Changchun Haipurunsi Technology Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Changchun Haipurunsi Technology Co Ltd filed Critical Changchun Haipurunsi Technology Co Ltd
Priority to CN201711111257.4A priority Critical patent/CN107721903A/zh
Publication of CN107721903A publication Critical patent/CN107721903A/zh
Withdrawn legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56Ring systems containing three or more rings
    • C07D209/80[b, c]- or [b, d]-condensed
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56Ring systems containing three or more rings
    • C07D209/80[b, c]- or [b, d]-condensed
    • C07D209/82Carbazoles; Hydrogenated carbazoles
    • C07D209/86Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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
    • C07D401/10Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/14Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic 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
    • C07D403/10Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/0803Compounds with Si-C or Si-Si linkages
    • C07F7/081Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C07F7/0814Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/0803Compounds with Si-C or Si-Si linkages
    • C07F7/081Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C07F7/0816Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00Organic light-emitting devices
    • H10K50/10OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/615Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/615Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/615Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/624Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/615Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/631Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/649Aromatic compounds comprising a hetero atom
    • H10K85/654Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/649Aromatic compounds comprising a hetero atom
    • H10K85/657Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/649Aromatic compounds comprising a hetero atom
    • H10K85/657Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/649Aromatic compounds comprising a hetero atom
    • H10K85/657Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1003Carbocyclic compounds
    • C09K2211/1007Non-condensed systems
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1003Carbocyclic compounds
    • C09K2211/1011Condensed systems
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1003Carbocyclic compounds
    • C09K2211/1014Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1029Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1029Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1029Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1044Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1059Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1088Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1092Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1096Heterocyclic compounds characterised by ligands containing other heteroatoms

Abstract

本发明提供一种有机电致发光材料及其有机发光器件,属于有机光电材料技术领域。本发明的一种有机电致发光材料结构中含有咔唑的结构,通过连接更多的共轭基团,可以有效地提高其玻璃化转化温度,减少使用中可能的结晶,此外更多的推电子基团的引入,导致了传输空穴的能力更强。与现有技术相比,将其应用于有机发光器件,特别是作为发光层中的主体材料使用,具有相对较高的发光效率和较低的驱动电压。

Description

一种有机电致发光材料及其有机发光器件
技术领域
本发明涉及有机光电材料技术领域,具体涉及一种有机电致发光材料及其有机发光器件。
背景技术
全色彩显示要求发射相对较稳定,色纯度高的红光、绿光和蓝光材料。在全色OLEDs中,蓝色发光层不仅可以有效地较少器件的能量损耗,而且可以通过将能量降低到能级更低的荧光或磷光来产生其他颜色的光。然而,由于蓝光发射材料的能极差较大,导致蓝光发射材料的性能要比绿光和红光低。另一方面,实现高效的深蓝色磷光发射很困难,按照规定CIE应该是y值小于0.15,x+Y值小于0.3,还有目前为止蓝色磷光器件的稳定性和寿命不能满足应用要求。
发明内容
有鉴于此,本发明的目的在于提供一种有机电致发光材料及其有机发光器件,采用本发明所述有机电致发光材料制备的有机发光器件,具有更高的发光效率,及更低的驱动电压。
本发明首先提供了一种有机电致发光材料,其结构通式如I所示:
其中,R1选自取代或未取代的C1-C30烷基、取代或未取代的C6-C50芳基、取代或未取代的C3-C50杂芳基中的一个;
R2到R5各自独立的选自氢、氰基、取代或未取代的C1-C30烷基、取代或未取代的C6-C50芳基、取代或未取代的C3-C50杂芳基中的一个;
a到d各自独立的表示0或者1;
所述杂芳基中的杂原子为B、N、O、S、Si或P中的至少一个。
优选的,所述的R2到R5各自独立的选自氢、氰基、取代或未取代的C1-C10烷基、取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基中的一个。
优选的,所述的一种有机电致发光材料,其结构通式如下所示:
优选的,所述的一种有机电致发光材料,其特征在于,选自如下结构中的任意一种:
本发明还提供一种有机发光器件,包括第一电极、第二电极和置于所述两电极之间的一个或多个有机化合物层,至少一个有机化合物层含有任一种有机电致发光材料。
优选的,有机化合物层包括发光层,发光层中含有任一种有机电致发光材料。
本发明的有益效果:
本发明的一种有机电致发光材料结构中含有咔唑的结构,通过连接更多的共轭基团,可以有效地提高其玻璃化转化温度,减少使用中可能的结晶,此外更多的推电子基团的引入,导致了传输空穴的能力更强。与现有技术相比,将其应用于有机发光器件,特别是作为发光层中的主体材料使用,具有相对较高的发光效率和较低的驱动电压。
具体实施方式
下面将结合本发明实施例的技术方案进行清楚、完整地描述,显然,所描述的实施例仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
本发明首先提供一种有机电致发光材料,结构通式如I所示:
其中,R1选自取代或未取代的C1-C30烷基、取代或未取代的C6-C50芳基、取代或未取代的C3-C50杂芳基中的一个;
R2到R5各自独立的选自氢、氰基、取代或未取代的C1-C30烷基、取代或未取代的C6-C50芳基、取代或未取代的C3-C50杂芳基中的一个;
a到d各自独立的表示0或者1;
所述杂芳基中的杂原子为B、N、O、S、Si或P中的至少一个。
按照本发明,所述芳基是指芳烃分子的芳核碳上去掉一个氢原子后,剩下一价基团的总称,其可以为单环芳基或稠环芳基,例如可选自苯基、联苯基、萘基、蒽基、菲基或芘基等,但不限于此。
所述杂芳基是指芳香族烃基中的一个或多个芳核碳被杂原子替代得到的基团的总称,所述杂原子包括但不限于氧、硫和氮原子,所述芳族杂环可以为单环或稠环,例如可选自吡啶基、嘧啶基、苯并嘧啶基、咔唑基、三嗪基、苯并噻唑基或苯并咪唑基等,但不限于此。
所述取代基是指取代有机化合物中氢原子的基团除去一个或几个-H而形成称作取代基的基团,如甲基、乙基、异丙基、叔丁基、苯基、萘基、蒽基、菲基、苯并菲基、基、苝基、芘基、苯甲基、甲氧基、甲硫基、苯氧基、苯硫基、芴基、9,9-二甲基芴基、二苯胺基、二甲胺基、咔唑基,9-苯基咔唑基、呋喃基、噻吩基、氰基、氟基、氘基、三苯基硅基、三甲基硅基、吩噻嗪基、吩噁嗪基、吖啶基、哌啶基、吡啶基、嘧啶基、联苯基、三联苯基、硝基等,但不限于此。
优选的,所述的R2到R5各自独立的选自氢、氰基、取代或未取代的C1-C10烷基、取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基中的一个。
优选的,所述的一种有机电致发光材料,其结构通式如下所示:
优选的,所述的一种有机电致发光材料,其特征在于,选自如下结构中的任意一种:
本发明所述一种有机电致发光材料的制备方法,包括所示的原料通过如下路线反应生成式I所示的一种有机电致发光材料:
其中,R1选自取代或未取代的C1-C30烷基、取代或未取代的C6-C50芳基、取代或未取代的C3-C50杂芳基中的一个;
R2到R5各自独立的选自氢、氰基、取代或未取代的C1-C30烷基、取代或未取代的C6-C50芳基、取代或未取代的C3-C50杂芳基中的一个;
a到d各自独立的表示0或者1;
所述杂芳基中的杂原子为B、N、O、S、Si或P中的至少一个。
本发明对上述各类反应的反应条件没有特殊要求,以本领域技术人员熟知的此类反应的常规条件即可。本发明对上述各类反应中所采用的原料的来源没有特别的限制,可以为市售产品或采用本领域技术人员所熟知的制备方法制备得到。
本发明还提供一种有机发光器件,所述有机发光器件为本领域技术人员所熟知的有机发光器件即可。本发明所述有机发光器件包括第一电极、第二电极和置于两电极之间的一个或多个有机化合物层,至少一个有机化合物层包含至少一种本发明所述的有机电致发光材料。所述有机化合物层优选包括空穴注入层、空穴传输层、发光层、空穴阻挡层、电子传输层与电子注入层中的至少一层,优选所述的发光层中含有本发明所述的有机电致发光材料。
实施例1:化合物1的制备
Step1,取100mmol的1,5-二溴化萘,加入100mmol的(2-硝基苯)硼酸,300mmol叔丁醇钾,10mmol CuI,甲苯,氩气置换三次,加入10mmol林菲罗啉,再次氩气置换三次,回流温度下反应6h,粗产品过硅胶柱,得到产品90mmol化合物1-1。
Step2,依次投入90mmol化合物1-1,溶剂邻二氯苯,亚硫酸三乙酯3当量,置换三次氩气,升温至165℃,反应15h。将反应液冷却到室温,在搅拌下,向釜中加入二氯甲烷,使产品全部溶剂,用去离子水洗涤有机相,150摄氏度加压蒸馏-,浓缩至干,得到黄色油状粘稠液体。黄粘稠液体中,加入甲醇、水,加热到回流,冷却到室温,有大量黄色固体颗粒物产生,减压过滤,得到的固体用甲醇洗涤至流出液无色。抽干后,晾干,得到黄色固体粉末。按照m:V=1g:7ml,加入甲苯,加热至回流,使粗品完全溶解。停止加入和搅拌,自然冷却至室温,次日,得到的黄色固体产品减压过滤,滤饼用无水乙醇淋洗至流出液无色。抽干后,减压烘干,得到黄色固体产品1-2 70mmol。
Step3,取70mmol 1-2,加入1当量的碘苯,210mmol叔丁醇钾,0.7mmol Pd2(dba)3,甲苯,氩气置换三次,加入0.7mmol三叔丁基膦,再次氩气置换三次,回流温度下反应6h,粗产品经由柱层析,得到产品62mmol化合物1-3
Step4,取62mmol 1-3,加入1当量的9-蒽硼酸,180mmol碳酸钠,0.6mmol四三苯基磷钯,甲苯,乙醇,水混合溶液,氩气置换三次,回流温度下反应6h,粗产品经由柱层析,得到产品45mmol化合物1。
实施例2:化合物2的制备
将实施例1中的碘苯更换为2-碘-9,9-二甲基芴。其它步骤同实施例1。
实施例3:化合物3的制备
将实施例1中的碘苯更换为2-溴二苯并呋喃。其它步骤同实施例1。
实施例4:化合物4的制备
将实施例1中的碘苯更换为3-溴-9-苯基咔唑。其它步骤同实施例1。
实施例5:化合物5的制备
Step1,取100mmol的1,5-二溴化萘,加入100mmol的(2-硝基苯)硼酸,300mmol叔丁醇钾,10mmol CuI,甲苯,氩气置换三次,加入10mmol林菲罗啉,再次氩气置换三次,回流温度下反应6h,粗产品过硅胶柱,得到产品90mmol化合物1-1。
Step2,依次投入90mmol化合物1-1,溶剂邻二氯苯,亚硫酸三乙酯3当量,置换三次氩气,升温至165℃,反应15h。将反应液冷却到室温,在搅拌下,向釜中加入二氯甲烷,使产品全部溶剂,用去离子水洗涤有机相,150摄氏度加压蒸馏-,浓缩至干,得到黄色油状粘稠液体。黄粘稠液体中,加入甲醇、水,加热到回流,冷却到室温,有大量黄色固体颗粒物产生,减压过滤,得到的固体用甲醇洗涤至流出液无色。抽干后,晾干,得到黄色固体粉末。按照m:V=1g:7ml,加入甲苯,加热至回流,使粗品完全溶解。停止加入和搅拌,自然冷却至室温,次日,得到的黄色固体产品减压过滤,滤饼用无水乙醇淋洗至流出液无色。抽干后,减压烘干,得到黄色固体产品1-2 70mmol。
Step3,取70mmol的化合物1-2,加入足量的溶剂氯仿和催化量的三氯化铁,降温到0摄氏度,滴加1.2当量的溴素的氯仿溶液,在此温度下反应24小时,用亚硫酸氢钠水溶液淬灭反应,蒸干有机溶剂,粗品过硅胶柱得到化合物5-3的溴代中间体,53mmol。
Step4,取53mmol 5-3,加入1当量的碘苯,150mmol叔丁醇钾,0.5mmol Pd2(dba)3,甲苯,氩气置换三次,加入0.5mmol三叔丁基膦,再次氩气置换三次,回流温度下反应6h,粗产品经由柱层析,得到产品42mmol化合物5-4。
Step5,取42mmol 5-3,加入2当量的2-萘硼酸,120mmol碳酸钠,0.4mmol四三苯基磷钯,甲苯,乙醇,水混合溶液,氩气置换三次,回流温度下反应6h,粗产品经由柱层析,得到产品35mmol化合物5。
实施例6:化合物6的制备
Step1-2:同实施例1。
Step3:将实施例1中step3中的碘苯换为3-溴二苯并呋。
Step4:取53mmol 5-3,加入1当量的吩噻嗪,150mmol叔丁醇钾,0.5mmol Pd2(dba)3,甲苯,氩气置换三次,加入0.5mmol三叔丁基膦,再次氩气置换三次,回流温度下反应6h,粗产品经由柱层析,得到产品42mmol化合物6。
实施例7:化合物7的制备
Step1,取100mmol的1,5-二溴化萘,加入100mmol的(2-硝基苯)硼酸,300mmol叔丁醇钾,10mmol CuI,甲苯,氩气置换三次,加入10mmol林菲罗啉,再次氩气置换三次,回流温度下反应6h,粗产品过硅胶柱,得到产品90mmol化合物1-1。
Step2,依次投入90mmol化合物1-1,溶剂邻二氯苯,亚硫酸三乙酯3当量,置换三次氩气,升温至165℃,反应15h。将反应液冷却到室温,在搅拌下,向釜中加入二氯甲烷,使产品全部溶剂,用去离子水洗涤有机相,150摄氏度加压蒸馏-,浓缩至干,得到黄色油状粘稠液体。黄粘稠液体中,加入甲醇、水,加热到回流,冷却到室温,有大量黄色固体颗粒物产生,减压过滤,得到的固体用甲醇洗涤至流出液无色。抽干后,晾干,得到黄色固体粉末。按照m:V=1g:7ml,加入甲苯,加热至回流,使粗品完全溶解。停止加入和搅拌,自然冷却至室温,次日,得到的黄色固体产品减压过滤,滤饼用无水乙醇淋洗至流出液无色。抽干后,减压烘干,得到黄色固体产品1-2 70mmol。
Step3,取70mmol的化合物1-2,加入足量的溶剂氯仿和催化量的三氯化铁,降温到0摄氏度,滴加2.2当量的溴素的氯仿溶液,在此温度下反应24小时,用亚硫酸氢钠水溶液淬灭反应,蒸干有机溶剂,粗品过硅胶柱得到化合物7-3的溴代中间体,53mmol。
Step4:取53mmol 7-3,加入1当量的2-(4-溴苯)-4,6-二苯-1,3,5-三嗪,150mmol叔丁醇钾,0.5mmol Pd2(dba)3,甲苯,氩气置换三次,加入0.5mmol三叔丁基膦,再次氩气置换三次,回流温度下反应6h,粗产品经由柱层析,得到产品42mmol化合物7-4。
Step5,取42mmol7-4,加入3当量的苯硼酸,120mmol碳酸钠,0.4mmol四三苯基磷钯,甲苯,乙醇,水混合溶液,氩气置换三次,回流温度下反应6h,粗产品经由柱层析,得到产品35mmol化合物7。
实施例8:化合物8的制备
Step1,取100mmol的1,5-二溴化萘,加入100mmol的(2-硝基苯)硼酸,300mmol叔丁醇钾,10mmol CuI,甲苯,氩气置换三次,加入10mmol林菲罗啉,再次氩气置换三次,回流温度下反应6h,粗产品过硅胶柱,得到产品90mmol化合物1-1。
Step2,依次投入90mmol化合物1-1,溶剂邻二氯苯,亚硫酸三乙酯3当量,置换三次氩气,升温至165℃,反应15h。将反应液冷却到室温,在搅拌下,向釜中加入二氯甲烷,使产品全部溶剂,用去离子水洗涤有机相,150摄氏度加压蒸馏-,浓缩至干,得到黄色油状粘稠液体。黄粘稠液体中,加入甲醇、水,加热到回流,冷却到室温,有大量黄色固体颗粒物产生,减压过滤,得到的固体用甲醇洗涤至流出液无色。抽干后,晾干,得到黄色固体粉末。按照m:V=1g:7ml,加入甲苯,加热至回流,使粗品完全溶解。停止加入和搅拌,自然冷却至室温,次日,得到的黄色固体产品减压过滤,滤饼用无水乙醇淋洗至流出液无色。抽干后,减压烘干,得到黄色固体产品1-2 70mmol。
Step3:取70mmol 1-2,加入1当量的4-溴-N,N-二苯基苯胺,210mmol叔丁醇钾,0.7mmol Pd2(dba)3,甲苯,氩气置换三次,加入0.7mmol三叔丁基膦,再次氩气置换三次,回流温度下反应6h,粗产品经由柱层析,得到产品50mmol化合物8-3。
Step4:取50mmol 2,4-二苯基-1,3,5-三嗪,溶解于无水THF,加入1.5当量的NaH,搅拌0.5小时,加入50mmol化合物8-3,室温下继续搅拌3小时。反应后,用水淬灭反应,DCM萃取,干燥浓缩,过硅胶柱得到产品8 41mmol。
实施例9:化合物9的制备
Step1,取100mmol的1,5-二溴化萘,加入100mmol的(2-硝基苯)硼酸,300mmol叔丁醇钾,10mmol CuI,甲苯,氩气置换三次,加入10mmol林菲罗啉,再次氩气置换三次,回流温度下反应6h,粗产品过硅胶柱,得到产品90mmol化合物1-1。
Step2,依次投入90mmol化合物1-1,溶剂邻二氯苯,亚硫酸三乙酯3当量,置换三次氩气,升温至165℃,反应15h。将反应液冷却到室温,在搅拌下,向釜中加入二氯甲烷,使产品全部溶剂,用去离子水洗涤有机相,150摄氏度加压蒸馏-,浓缩至干,得到黄色油状粘稠液体。黄粘稠液体中,加入甲醇、水,加热到回流,冷却到室温,有大量黄色固体颗粒物产生,减压过滤,得到的固体用甲醇洗涤至流出液无色。抽干后,晾干,得到黄色固体粉末。按照m:V=1g:7ml,加入甲苯,加热至回流,使粗品完全溶解。停止加入和搅拌,自然冷却至室温,次日,得到的黄色固体产品减压过滤,滤饼用无水乙醇淋洗至流出液无色。抽干后,减压烘干,得到黄色固体产品1-2 70mmol。
Step3:取黄色固体产品1-2 70mmol,溶解于无水THF,加入1.5当量的NaH,搅拌0.5小时,加入70mmol化合物2-溴-5-苯基嘧啶,室温下继续搅拌3小时。反应后,用水淬灭反应,DCM萃取,干燥浓缩,过硅胶柱得到产品9-3 61mmol。
Step4:取61mmol化合物9-3,加入1当量的9-苯基-咔唑-2-硼酸,180mmol碳酸钠,0.6mmol四三苯基磷钯,甲苯,乙醇,水混合溶液,氩气置换三次,回流温度下反应6h,粗产品经由柱层析,得到产品55mmol化合物9。
实施例10:化合物10的制备
Step1,取100mmol的1,5-二溴化萘,加入100mmol的(2-硝基苯)硼酸,300mmol叔丁醇钾,10mmol CuI,甲苯,氩气置换三次,加入10mmol林菲罗啉,再次氩气置换三次,回流温度下反应6h,粗产品过硅胶柱,得到产品90mmol化合物1-1。
Step2,依次投入90mmol化合物1-1,溶剂邻二氯苯,亚硫酸三乙酯3当量,置换三次氩气,升温至165℃,反应15h。将反应液冷却到室温,在搅拌下,向釜中加入二氯甲烷,使产品全部溶剂,用去离子水洗涤有机相,150摄氏度加压蒸馏-,浓缩至干,得到黄色油状粘稠液体。黄粘稠液体中,加入甲醇、水,加热到回流,冷却到室温,有大量黄色固体颗粒物产生,减压过滤,得到的固体用甲醇洗涤至流出液无色。抽干后,晾干,得到黄色固体粉末。按照m:V=1g:7ml,加入甲苯,加热至回流,使粗品完全溶解。停止加入和搅拌,自然冷却至室温,次日,得到的黄色固体产品减压过滤,滤饼用无水乙醇淋洗至流出液无色。抽干后,减压烘干,得到黄色固体产品1-2 70mmol。
Step3:取70mmol 1-2,加入1当量的4-溴-喹啉,210mmol叔丁醇钾,0.7mmol Pd2(dba)3,甲苯,氩气置换三次,加入0.7mmol三叔丁基膦,再次氩气置换三次,回流温度下反应6h,粗产品经由柱层析,得到产品50mmol化合物10-3。
Step4:取50mmol化合物10-3,加入1当量的9-苯基-咔唑-3-硼酸,150mmol碳酸钠,0.5mmol四三苯基磷钯,甲苯,乙醇,水混合溶液,氩气置换三次,回流温度下反应6h,粗产品经由柱层析,得到产品45mmol化合物10。
本发明实施例制备得到的一种有机电致发光材料的FD-MS值见表1所示。
表1本发明实施例制备的化合物FD-MS值
化合物 FD-MS
6 M/z:343.27,C40H25N(519.2)
11 M/z:443.54,C41H29N(535.23)
19 M/z:493.25,C38H23NO(509.18)
21 M/z:459.03,C44H28N2(584.23)
38 M/z:583.63,C46H29N(595.23)
54 M/z:433.29,C44H26N2OS(630.18)
63 M/z:802.36,C59H38N4(802.31)
64 M/z:741.36,C53H35N5(741.29)
65 M/z:662.36,C48H30N4(662.25)
66 M/z:635.36,C47H29N3(635.28)
对比应用实施例1:
将ITO玻璃基板放在蒸馏水中清洗2次,超声波洗涤30分钟,蒸馏水清洗结束后,异丙醇、丙酮、甲醇等溶剂按顺序超声波洗涤以后干燥,转移到等离子体清洗机里,将上述基板洗涤5分钟,送到蒸镀机里。
在已经准备好的ITO透明电极上依次蒸镀空穴注入层蒸镀空穴传输层蒸镀发光层主体mCP:客体掺杂Alq3 5%然后蒸镀电子传输层阴极上述过程有机物蒸镀速度是保持LiF是Al是
应用实例1:
在已经准备好的ITO透明电极上依次蒸镀空穴注入层蒸镀空穴传输层蒸镀发光层主体化合物6:客体掺杂Alq3 5%然后蒸镀电子传输层阴极上述过程有机物蒸镀速度是保持LiF是Al是
应用实例2:
将应用实施例1中的化合物6换成化合物11。测量该器件的发光性能,结果见表2。
应用实例3:
将应用实施例1中的化合物6换成化合物19。测量该器件的发光性能,结果见表2。
应用实例4:
将应用实施例1中的化合物6换成化合物21。测量该器件的发光性能,结果见表2。
应用实例5:
将应用实施例1中的化合物6换成化合物38。测量该器件的发光性能,结果见表2。
应用实例6:
将应用实施例1中的化合物6换成化合物54。测量该器件的发光性能,结果见表2。
对比应用实施例2:
将ITO玻璃基板放在蒸馏水中清洗2次,超声波洗涤30分钟,蒸馏水清洗结束后,异丙醇、丙酮、甲醇等溶剂按顺序超声波洗涤以后干燥,转移到等离子体清洗机里,将上述基板洗涤5分钟,送到蒸镀机里。
在已经准备好的ITO透明电极上依次蒸镀空穴注入层2-TNATA蒸镀空穴传输层蒸镀发光层主体mCP:客体掺杂DCM 2%然后蒸镀电子传输层阴极上述过程有机物蒸镀速度是保持LiF是Al是
应用实例7:
在已经准备好的ITO透明电极上依次蒸镀空穴注入层2-TNATA蒸镀空穴传输层蒸镀发光层主体化合物63:客体掺杂化合物DCM2%然后蒸镀电子传输层阴极上述过程有机物蒸镀速度是保持LiF是Al是
应用实例8:
将应用实施例1中的化合物63换成化合物64。测量该器件的发光性能,结果见表2。
应用实例9:
将应用实施例1中的化合物63换成化合物65。测量该器件的发光性能,结果见表2。
应用实例10:
将应用实施例1中的化合物63换成化合物66。测量该器件的发光性能,结果见表2。
测量实施例1:对比样品以及样品的发光性能
对比样品以及样品是采用Keithley SMU235,PR650评价发光效率和驱动电压,结果列于表2中:
表2本发明实施例制备的发光器件的发光特性
虽然本发明用示范性实施方案进行了特别的描述,但应该理解在不偏离权利要求所限定的本发明的精神与范围的情况下,本领域普通技术人员可对其进行各种形式和细节上的改变。

Claims (6)

1.一种有机电致发光材料,其结构通式如I所示:
其中,R1选自取代或未取代的C1-C30烷基、取代或未取代的C6-C50芳基、取代或未取代的C3-C50杂芳基中的一个;
R2到R5各自独立的选自氢、氰基、取代或未取代的C1-C30烷基、取代或未取代的C6-C50芳基、取代或未取代的C3-C50杂芳基中的一个;
a到d各自独立的表示0或者1;
所述杂芳基中的杂原子为B、N、O、S、Si或P中的至少一个。
2.根据权利要求1所述的一种有机电致发光材料,R2到R5各自独立的选自氢、氰基、取代或未取代的C1-C10烷基、取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基中的一个。
3.根据权利要求1所述的一种有机电致发光材料,其结构通式如下所示:
4.根据权利要求1所述的一种有机电致发光材料,其特征在于,选自如下结构中的任意一种:
5.一种有机发光器件,包括第一电极、第二电极和置于所述两电极之间的一个或多个有机化合物层,其特征在于,至少一个有机化合物层含有如权利要求1-4中所述的任一种有机电致发光材料。
6.根据权利要求5中所述的一种有机发光器件,其特征在于,所述有机化合物层包括发光层,发光层中含有如权利要求1-4中所述的任一种有机电致发光材料。
CN201711111257.4A 2017-11-13 2017-11-13 一种有机电致发光材料及其有机发光器件 Withdrawn CN107721903A (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201711111257.4A CN107721903A (zh) 2017-11-13 2017-11-13 一种有机电致发光材料及其有机发光器件

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201711111257.4A CN107721903A (zh) 2017-11-13 2017-11-13 一种有机电致发光材料及其有机发光器件

Publications (1)

Publication Number Publication Date
CN107721903A true CN107721903A (zh) 2018-02-23

Family

ID=61214413

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201711111257.4A Withdrawn CN107721903A (zh) 2017-11-13 2017-11-13 一种有机电致发光材料及其有机发光器件

Country Status (1)

Country Link
CN (1) CN107721903A (zh)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019102292A1 (ja) * 2017-11-24 2019-05-31 株式会社半導体エネルギー研究所 ジベンゾ[c,g]カルバゾール誘導体、発光素子、発光装置、電子機器および照明装置
CN112480077A (zh) * 2020-11-17 2021-03-12 上海和辉光电股份有限公司 一种用于有机发光的化合物及其应用

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010114264A2 (en) * 2009-03-31 2010-10-07 Dow Advanced Display Materials,Ltd. Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN107074764A (zh) * 2014-09-26 2017-08-18 罗门哈斯电子材料韩国有限公司 有机电致发光化合物以及包含其的有机电致发光材料和有机电致发光装置

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010114264A2 (en) * 2009-03-31 2010-10-07 Dow Advanced Display Materials,Ltd. Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN107074764A (zh) * 2014-09-26 2017-08-18 罗门哈斯电子材料韩国有限公司 有机电致发光化合物以及包含其的有机电致发光材料和有机电致发光装置

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019102292A1 (ja) * 2017-11-24 2019-05-31 株式会社半導体エネルギー研究所 ジベンゾ[c,g]カルバゾール誘導体、発光素子、発光装置、電子機器および照明装置
CN111372917A (zh) * 2017-11-24 2020-07-03 株式会社半导体能源研究所 二苯并[c,g]咔唑衍生物、发光元件、发光装置、电子设备及照明装置
US11641777B2 (en) * 2017-11-24 2023-05-02 Semiconductor Energy Laboratory Co., Ltd. Dibenzo[c,g]carbazole derivative, light-emitting device, light-emitting apparatus, electronic device, and lighting device
CN112480077A (zh) * 2020-11-17 2021-03-12 上海和辉光电股份有限公司 一种用于有机发光的化合物及其应用
CN112480077B (zh) * 2020-11-17 2022-04-12 上海和辉光电股份有限公司 一种用于有机发光的化合物及其应用

Similar Documents

Publication Publication Date Title
CN105753629B (zh) 化合物和使用其的有机电致发光装置
CN102428159A (zh) 用于发光应用的*化合物
CN103183691B (zh) 含有取代或非取代咔唑基的6-均三甲苯基-6H-6-硼杂苯并[cd]芘衍生物及制备方法及应用及含其的发光器件
CN107312017A (zh) 一种含吩噁嗪/噻噁嗪类衍生物的有机电致发光材料及其有机发光器件
CN108359445A (zh) 一种双极性有机电致发光材料及其有机发光器件
CN107573307A (zh) 一种有机电致发光材料及有机发光器件
CN107235997A (zh) 一种螺硅芴衍生物及其有机发光器件
JP2015523377A (ja) 新規な化合物及びこれを含む有機電界発光素子
CN107417702A (zh) 一种新颖的有机电致发光材料及有机发光器件
KR20110049012A (ko) 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자
CN108129386A (zh) 基于打断共轭的给受体型分子内基激复合物发光材料及其在制备有机电致发光器件中的应用
CN109053810A (zh) 有机金属铱化合物及有机电致发光器件
CN108912175A (zh) 一种金属铱配合物及其有机发光器件
CN108276342A (zh) 一种含蒽结构的有机电致发光材料及其有机发光器件
CN107337630A (zh) 一种含芴环结构的四苯基乙烯有机电致发光材料及其有机发光器件
CN109651435B (zh) 一种双极性有机光电功能材料及制备方法
CN107759559A (zh) 化合物及其有机电子装置
CN107721903A (zh) 一种有机电致发光材料及其有机发光器件
CN107652969A (zh) 一种有机电致发光材料及其有机发光器件
CN108774266A (zh) 一种铱配合物及其有机发光器件
CN108409680A (zh) 一种螺芴并含氮杂环类有机电致发光材料及其有机发光器件
CN108329271A (zh) 一种含蒽和苯并咪唑结构的有机电致发光材料及其有机发光器件
CN107602605A (zh) 一种有机电致发光材料及其有机发光器件
CN106749375B (zh) 一种三苯基硅基相连苯并噻吩衍生物及使用该衍生物的有机发光器件
CN105777809B (zh) 有机电致发光材料及有机电致发光器件

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
WW01 Invention patent application withdrawn after publication

Application publication date: 20180223

WW01 Invention patent application withdrawn after publication