CN106467526A - A kind of organic compound containing xanthene and its application - Google Patents

A kind of organic compound containing xanthene and its application Download PDF

Info

Publication number
CN106467526A
CN106467526A CN201610754307.XA CN201610754307A CN106467526A CN 106467526 A CN106467526 A CN 106467526A CN 201610754307 A CN201610754307 A CN 201610754307A CN 106467526 A CN106467526 A CN 106467526A
Authority
CN
China
Prior art keywords
formula
organic compound
compound
expressed
key
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
Application number
CN201610754307.XA
Other languages
Chinese (zh)
Other versions
CN106467526B (en
Inventor
张兆超
李崇
张小庆
叶中华
王立春
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.)
Jiangsu Sunera Technology Co Ltd
Original Assignee
Jiangsu Sanyue Optoelectronic 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 Jiangsu Sanyue Optoelectronic Technology Co Ltd filed Critical Jiangsu Sanyue Optoelectronic Technology Co Ltd
Priority to CN201610754307.XA priority Critical patent/CN106467526B/en
Publication of CN106467526A publication Critical patent/CN106467526A/en
Application granted granted Critical
Publication of CN106467526B publication Critical patent/CN106467526B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic 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
    • C07D471/12—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 three hetero rings
    • C07D471/14—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
    • C07D487/04—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
    • C07D487/12—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 three hetero rings
    • C07D487/14—Ortho-condensed systems
    • 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
    • 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
    • C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
    • 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
    • C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
    • 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
    • C07D491/12—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 three hetero rings
    • C07D491/14—Ortho-condensed systems
    • C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
    • 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
    • C07D491/12—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 three hetero rings
    • C07D491/14—Ortho-condensed systems
    • C07D491/153—Ortho-condensed systems the condensed system containing two rings with oxygen as ring hetero atom and one ring with nitrogen as ring hetero atom
    • 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
    • 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
    • C07D495/12—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 three hetero rings
    • C07D495/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D498/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
    • C07D513/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D517/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms
    • C07D517/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms in which the condensed system contains two hetero rings
    • C07D517/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D517/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms
    • C07D517/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms in which the condensed system contains three hetero rings
    • C07D517/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom 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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/104—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with other 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
    • 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

The invention discloses a kind of organic compound containing xanthene and its application, shown in the structural formula formula such as formula (1) of this organic compound.The organic compound vitrification point that the present invention provides is high, and molecule heat stability is strong, has suitable HOMO and lumo energy and higher Eg, is optimized by device architecture, can effectively lift the photoelectric properties of OLED and the life-span of OLED.

Description

A kind of organic compound containing xanthene and its application
Technical field
The present invention relates to organic photoelectrical material technical field, especially relate to one kind containing skeleton centered on xanthene structure Compound-material and its application in OLED field.
Background technology
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology both can be used to make Make new display product it is also possible to be used for making novel illumination product, be expected to substitute existing liquid crystal display and fluorescent lighting, Application prospect is quite varied.
OLED luminescent device just as the structure of sandwich, including electrode material film layer, and be clipped in Different electrodes film layer it Between organic functional material, various difference in functionality materials are overlapped mutually according to purposes and collectively constitute OLED luminescent device together. As current device, when the two end electrodes applied voltage to OLED luminescent device, and pass through electric field action organic layer functional material Positive and negative charge in film layer, positive and negative charge is compound in luminescent layer further, that is, produce OLED electroluminescent.
Currently, in smart mobile phone, the field such as panel computer obtains application to OLED Display Technique, further also will be to electricity Depending on etc. the extension of large scale application, but, require to compare with the products application of reality, the luminous efficiency of OLED, use The performances such as life-span also need to be lifted further.
High performance research is carried for OLED luminescent device include：Reduce the driving voltage of device, improve the luminous of device Efficiency, improves service life of device etc..In order to realize the continuous lifting of the performance of OLED, not only need from OLED Structure and the innovation of processing technology, constantly study with greater need for oled light sulfate ferroelectric functional material and innovate, formulate out higher performance OLED Functional material.
The oled light sulfate ferroelectric functional material being applied to OLED can be divided into two big class from purposes, i.e. electric charge injection transmission Material and luminescent material, further, also can inject charge into transmission material and be divided into electron injection transmission material, electronic blocking material Luminescent material can also be divided into main body luminescent material and dopant material by material, hole injection transmission material and hole barrier materials.
In order to make high performance OLED luminescent device it is desirable to various organic functional material possesses good photoelectric characteristic, Such as, as charge transport materials it is desirable to have good carrier mobility, high-vitrification conversion temperature etc., as luminous The material of main part of layer requires material to have good bipolarity, suitable HOMO/LUMO energy rank etc..
The oled light sulfate ferroelectric functional material film layer constituting OLED at least includes the above structure of two-layer, application in industry OLED structure, then include hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electronics biography Multiple film layer such as defeated layer, electron injecting layer is that is to say, that the photoelectric functional material being applied to OLED includes at least hole note Enter material, hole mobile material, luminescent material, electron transport material etc., material type and collocation form have rich and many The feature of sample.In addition, for the OLED of different structure is arranged in pairs or groups, the photoelectric functional material that used has stronger Selectivity, performance in different structure device for the identical material is it is also possible to completely totally different.
Therefore, for the industry application requirement of current OLED, and the difference in functionality film layer of OLED, device Photoelectric characteristic demand, it is necessary to select to be more suitable for, has high performance OLED functional material or combination of materials, just enables device The overall characteristic of high efficiency, long-life and low-voltage.For the actual demand that current OLED shows Lighting Industry, current OLED The development of material is also far from enough, lags behind the requirement of panel manufacturing enterprise, organic as material enterprise development higher performance Functional material is particularly important.
Content of the invention
For prior art exist the problems referred to above, the applicant provide a kind of organic compound containing xanthene and It is applied on organic electroluminescence device.The organic compound vitrification point that the present invention provides is high, and molecule heat stability is strong, There is suitable HOMO and lumo energy and higher Eg, optimized by device architecture, can effectively lift the photoelectricity of OLED Performance and the life-span of OLED.
Technical scheme is as follows：
The applicant provides a kind of organic compound containing xanthene, the general structure such as formula of described compound (1) shown in：
Wherein, Ar1、Ar2It is expressed as phenyl, xenyl or naphthyl；
R1、R2Independently be expressed as structure shown in formula (2)；R1With R2Can be identical or different；R1Also may indicate that For hydrogen atom；
In formula (2), R3、R4Independently be expressed as structure in hydrogen atom, formula (3) or formula (4)；
In formula (3), a is selected fromX1、X2、X3Independently be expressed as oxygen Atom, sulphur atom, selenium atom, C1-10The alkylidene of straight or branched alkyl replacement, the alkylidene of aryl replacement, alkyl or aryl One of tertiary amine groups replacing；
Formula (3), formula (4) pass through CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL‘1-CL’2Key, CL‘2-CL’3Key or CL‘3-CL’4Key and formula (2) connect.
Preferably, described R1、R2Being expressed as independently：
In any one.
Preferably, the concrete structure formula of the described organic compound containing xanthene is：
In any one.
The applicant additionally provides a kind of preparation method of described organic compound, works as R1When being expressed as hydrogen atom, preparation During reaction equation be：
Described preparation method is with Br-Ar2- Br is raw material, by grignard reaction, prepared Grignard reagent, then and Oxoxanthone Reaction, generates the tertiary alcohol, the then tertiary alcohol and H-Ar1Reacted by friedel-craft, a bromo compound, Ran Houhe are obtainedIt is coupled by C-N and described compound is obtained.
The applicant additionally provides the preparation method of another kind of described organic compound, works as R1It is expressed as the knot of formula (2) During structure, the reaction equation in preparation process is：
Described preparation method is with Br-Ar2- Br is raw material, by grignard reaction, prepared Grignard reagent, then and Oxoxanthone Reaction, generates the tertiary alcohol, the then tertiary alcohol and H-Ar1- Br is reacted by friedel-craft, and two bromo compounds, Ran Houhe are obtainedIt is coupled by C-N and described compound is obtained.
The applicant additionally provides a kind of organic electroluminescence device comprising the described organic compound containing xanthene, Described organic compound is applied between negative electrode and anode as emitting layer material, is used for preparing organic electroluminescent LED.
Beneficial the having technical effect that of the present invention：
The compounds of this invention with xanthene as parent nucleus, connected symmetrical dendrimer or asymmetrical rigid radical, the crystallization of saboteur Property, it is to avoid intermolecular aggregation, there is high vitrification point, material, when OLED is applied, can keep high film Layer stability, improves OLED service life.
The compounds of this invention structure makes electronics and hole more balance in the distribution of luminescent layer, in appropriate HOMO energy level Under, improve hole injection/transmission performance；Under suitable lumo energy, serve the effect of electronic blocking again, lift exciton Combined efficiency in luminescent layer；As OLED luminescent device light emitting functional layer materials'use when, aryl replace xanthene Side chain in the collocation scope of the invention can effectively improve exciton utilization rate and high fluorescent radiation efficiency, reduces under high current density Efficiency roll-off, reduces device voltage, improves current efficiency and the life-span of device.
The special construction of compound of the present invention designs so that material also has while having high decomposition temperature Low sublimation temperature or vacuum evaporation temperature, have higher temperature difference window between sublimation temperature or evaporation temperature and decomposition temperature Mouth, so that material has higher operation controllability in commercial Application, is applied beneficial to material volume production.
Compound of the present invention has good application effect in OLED luminescent device, before having good industrialization Scape.
Brief description
Materials application cited by the present invention for the Fig. 1 is in the structural representation of OLED；
Wherein, 1 is transparent substrate layer, and 2 is ito anode layer, and 3 is hole injection layer, and 4 is hole transport/electronic barrier layer, 5 is luminescent layer, and 6 is electric transmission/hole blocking layer, and 7 is electron injecting layer, and 8 is negative electrode reflection electrode layer.
Specific embodiment
With reference to the accompanying drawings and examples, the present invention is specifically described.
Embodiment 1：The synthesis of raw material A 1：
Synthetic route：
The four-hole bottle of 250ml, under the atmosphere being passed through nitrogen, add 11.8g Isosorbide-5-Nitrae-dibromobenzene (0.05mol) and 1.33gMg powder (0.055mol), 60ml oxolane, it is heated to reflux 4 hours, reaction completely, generates grignard reagent；
10.8g Oxoxanthone (0.05mol) is dissolved in 50ml oxolane, the above-mentioned grignard reagent of Deca, and 60 DEG C of reactions 24 are little When, generate a large amount of white precipitates, be eventually adding saturation NHCl4Form salt is converted into alcohol；After completion of the reaction, ether extraction, does Dry revolving, petroleum ether：Dichloromethane mixed solvent (3:2) silica column purification, (yield is to obtain the solid tertiary alcohol of yellowish 85%)；Identify this compound, molecular formula C using DEI-MS19H13BrO2, detected value [M+1]+=354.08, value of calculation 353.21；
By 1:2 when measuring the above-mentioned tertiary alcohol of 14.1g (0.04mol) and 12.5g bromobenzene (0.08mol) is dissolved in 100ml dichloromethane In alkane, Deca 8ml boron trifluoride etherate at ambient temperature, reacts 30 minutes, adds 20ml ethanol and 20ml water Reaction is quenched, with dichloromethane (20ml*3) extraction, revolving, petroleum ether silica column purification is dried, uses ethanol：Dichloromethane is tied again Crystalline substance, yield is 72%；Identify this compound, molecular formula C using DEI-MS25H16Br2O, detected value [M+1]+=492.92, meter Calculation value 492.20；
Embodiment 2：The synthesis of raw material A 2：
Synthetic route：
By synthetic method preparing raw material A2 of raw material A1 in embodiment 1, difference is to use 1, and 1 '-biphenyl replaces compound Bromobenzene；
Identify this compound, molecular formula C using DEI-MS31H21BrO, detected value [M+1]+=490.05, value of calculation 489.40.
Embodiment 3：The synthesis of raw material A 3：
Synthetic route：
By synthetic method preparing raw material A3 of raw material A1 in embodiment 1, difference is to be replaced with benzene in three-step reaction Bromobenzene；
Identify this compound, molecular formula C using DEI-MS25H17BrO, detected value [M+1]+=414.02, value of calculation 413.31.
Embodiment 4：The synthesis of raw material A 4：
Synthetic route：
By synthetic method preparing raw material A4 of raw material A1 in embodiment 1, difference is to be replaced with naphthalene in three-step reaction Bromobenzene；
Identify this compound, molecular formula C using DEI-MS29H19BrO, detected value [M+1]+=463.97, value of calculation 463.36.
Embodiment 5：The synthesis of compound 1：
Synthetic route：
In the there-necked flask of 250ml, under logical nitrogen protection, addition 0.01mol raw material A 1,0.024mol raw material B1, 0.04mol sodium tert-butoxide, 1 × 10-4molpd2(dba)3, 1 × 10-4Mol tri-tert phosphorus, 150ml toluene, it is heated to reflux 24 little When, sample point plate, reaction is completely；Natural cooling, filters, filtrate revolving, column chromatography obtains target product, HPLC purity 99.7%, yield 71.3%；
Elementary analysiss structure (molecular formula C49H32N2O)：Theoretical value C, 88.53；H,4.85；N,4.21；O,2.41；Test Value：C,88.54；H,4.86；N,4.20；O,2.40.
HPLC-MS：Material molecule amount is 664.79, surveys molecular weight 665.03.
Embodiment 6：The synthesis of compound 2：
Synthetic route：
In the there-necked flask of 250ml, under logical nitrogen protection, addition 0.01mol raw material A 2,0.012mol raw material C1, 0.03mol sodium tert-butoxide, 5 × 10-5mol pd2(dba)3, 5 × 10-5Mol tri-tert phosphorus, 150ml toluene, it is heated to reflux 24 Hour, sample point plate, reaction is completely；Natural cooling, filters, filtrate revolving, column chromatography obtains target product, HPLC purity 99.1%, yield 75.3%；
Elementary analysiss structure (molecular formula C51H33NO)：Theoretical value C, 90.64；H,4.92；N,2.07；O,2.37；Test Value：C,90.64；H,4.93；N,2.08；O,2.35.
HPLC-MS：Material molecule amount is 675.81, surveys molecular weight 676.04.
Embodiment 7：The synthesis of compound 8：
Synthetic route：
In the there-necked flask of 250ml, under logical nitrogen protection, addition 0.01mol raw material A 3,0.012mol raw material D1, 0.03mol sodium tert-butoxide, 5 × 10-5mol pd2(dba)3, 5 × 10-5Mol tri-tert phosphorus, 150ml toluene, it is heated to reflux 24 Hour, sample point plate, reaction is completely；Natural cooling, filters, filtrate revolving, column chromatography obtains target product, HPLC purity 99.1%, yield 72.5%；
Elementary analysiss structure (molecular formula C49H32N2O)：Theoretical value C, 88.53；H,4.85；N,4.21；O,2.41；Test Value：C,88.54；H,4.84；N,4.22；O,2.40.
HPLC-MS：Material molecule amount is 664.79, surveys molecular weight 665.08.
Embodiment 8：The synthesis of compound 10：
Synthetic route：
In the there-necked flask of 250ml, under logical nitrogen protection, addition 0.01mol raw material A 4,0.012mol raw material D2, 0.03mol sodium tert-butoxide, 5 × 10-5mol pd2(dba)3, 5 × 10-5Mol tri-tert phosphorus, 150ml toluene, it is heated to reflux 24 Hour, sample point plate, reaction is completely；Natural cooling, filters, filtrate revolving, column chromatography obtains target product, HPLC purity 98.7%, yield 73.6%；
Elementary analysiss structure (molecular formula C50H35NO)：Theoretical value C, 90.19；H,5.30；N,2.10；O,2.40；Test Value：C,90.16；H,5.31；N,2.12；O,2.41.
HPLC-MS：Material molecule amount is 665.82, surveys molecular weight 666.13.
Embodiment 9：The synthesis of compound 13：
Synthetic route：
By the synthetic method preparation of compound 8 in embodiment 7, difference is to replace raw material D1 with raw material E1；
Elementary analysiss structure (molecular formula C50H35NO)：Theoretical value C, 90.19；H,5.30；N,2.10；O,2.40；Test Value：C,90.16；H,5.32；N,2.11；O,2.41.
HPLC-MS：Material molecule amount is 665.82, surveys molecular weight 666.03.
Embodiment 10：The synthesis of compound 18：
Synthetic route：
By the synthetic method preparation of compound 8 in embodiment 7, difference is to replace raw material D1 with raw material D3；
Elementary analysiss structure (molecular formula C43H27NO2)：Theoretical value C, 87.58；H,4.62；N,2.38；O,5.43；Test Value：C,87.60；H,4.61；N,2.37；O,5.42.
HPLC-MS：Material molecule amount is 589.68, surveys molecular weight 590.01.
Embodiment 11：The synthesis of compound 32：
Synthetic route：
By the synthetic method preparation of compound 8 in embodiment 7, difference is to replace raw material D1 with raw material F1 generation；
Elementary analysiss structure (molecular formula C61H39N3O)：Theoretical value C, 88.27；H,4.74；N,5.06；O,1.93；Test Value：C,88.28；H,4.75；N,5.05；O,1.92.
HPLC-MS：Material molecule amount is 829.98, surveys molecular weight 930.35.
Embodiment 12：The synthesis of compound 46：
Synthetic route：
By the synthetic method preparation of compound 8 in embodiment 7, difference is to replace raw material D1 with raw material F2；
Elementary analysiss structure (molecular formula C55H41NO)：Theoretical value C, 90.25；H,5.65；N,1.91；O,2.19；Test Value：C,90.28；H,5.64；N,1.90；O,2.18.
HPLC-MS：Material molecule amount is 731.92, surveys molecular weight 732.36.
Embodiment 13：The synthesis of compound 48：
Synthetic route：
By the synthetic method preparation of compound 8 in embodiment 7, difference is to replace raw material D1 with raw material G1；
Elementary analysiss structure (molecular formula C46H33NO2)：Theoretical value C, 87.45；H,5.26；N,2.22；O,5.07；Test Value：C,87.48；H,5.25；N,2.21；O,5.06.
HPLC-MS：Material molecule amount is 631.76, surveys molecular weight 632.05.
Embodiment 14：The synthesis of compound 56：
Synthetic route：
By the synthetic method preparation of compound 8 in embodiment 7, difference is to replace raw material D1 with raw material F3；
Elementary analysiss structure (molecular formula C55H41NO)：Theoretical value C, 90.25；H,5.65；N,1.91；O,2.19；Test Value：C,90.26；H,5.64；N,1.92；O,2.18.
HPLC-MS：Material molecule amount is 731.92, surveys molecular weight 732.32.
Embodiment 15：The synthesis of compound 58：
Synthetic route：
By the synthetic method preparation of compound 8 in embodiment 7, difference is to replace raw material D1 with raw material G2；
Elementary analysiss structure (molecular formula C46H33NO2)：Theoretical value C, 87.45；H,5.26；N,2.22；O,5.07；Test Value：C,87.43；H,5.27；N,2.22；O,5.08.
HPLC-MS：Material molecule amount is 631.76, surveys molecular weight 632.08.
Embodiment 16：The synthesis of compound 66：
Synthetic route：
By the synthetic method preparation of compound 8 in embodiment 7, difference is to replace raw material D1 with raw material G3；
Elementary analysiss structure (molecular formula C46H33NO2)：Theoretical value C, 87.45；H,5.26；N,2.22；O,5.07；Test Value：C,87.47；H,5.25；N,2.21；O,5.07.
HPLC-MS：Material molecule amount is 631.76, surveys molecular weight 632.02.
Embodiment 17：The synthesis of compound 86：
Synthetic route：
By the synthetic method preparation of compound 8 in embodiment 7, difference is to replace raw material D1 with raw material G3；
Elementary analysiss structure (molecular formula C51H34N2O)：Theoretical value C, 88.67；H,4.96；N,4.06；O,2.32；Test Value：C,88.69；H,4.95；N,4.05；O,2.31.
HPLC-MS：Material molecule amount is 690.83, surveys molecular weight 691.12.
Embodiment 18：The synthesis of compound 95：
Synthetic route：
By the synthetic method preparation of compound 8 in embodiment 7, difference is to replace raw material D1 with raw material I1；
Elementary analysiss structure (molecular formula C64H45N3O2)：Theoretical value C, 86.56；H,5.11；N,4.73；O,3.60；Test Value：C,86.53；H,5.12；N,4.74；O,3.61.
HPLC-MS：Material molecule amount is 888.06, surveys molecular weight 888.44.
The compounds of this invention uses in luminescent device, can be as hole transport/electronic blocking layer material it is also possible to make For luminescent layer Subjective and Objective materials'use.The compounds of this invention has high operability and practicality, major embodiment in application For having high glass transition temperature, low sublimation temperature, high decomposition temperature and film forming stability.
The compounds of this invention 8, compound 32, compound 48, current material CBP are carried out respectively hot property, luminescent spectrum, The test of HOMO energy level, testing result is as shown in table 1.
Table 1
Note：Vitrification point Tg is by differential scanning calorimetry (DSC, German Nai Chi company DSC204F1 differential scanning calorimetry Instrument) measure, 10 DEG C/min of heating rate；Evaporation temperature is using SUNIC evaporated device, vacuum ＜ 1E-5Pa, material rate ForWhen evaporation temperature；Thermal weight loss temperature Td is in nitrogen atmosphere weightless 1% temperature, in Japanese Shimadzu Corporation It is measured on TGA-50H thermogravimetric analyzer, nitrogen flow is 20mL/min；Film forming stability refers to, using SUNIC evaporator Platform, is deposited with to glass substrate 100nm thickness thin film material, envelope in glove box environment (water oxygen content equal ＜ 1PPm) Dress, after encapsulation, glass sample under the conditions of double 80 (humidity 80%, 80 DEG C of temperature) places test 240 hours, uses micro- sem observation The crystal property of sample film；Highest occupied molecular orbital HOMO energy level and minimum occupied molecular orbital lumo energy are by photoelectron Transmitting spectrometer (AC-2 type PESA) test, tests as atmospheric environment.
From upper table data, the compounds of this invention has adjustable HOMO energy level, is suitable as difference in functionality layer material Use；Low evaporation temperature can make material in commercial Application, reduces heat radiation to Fine-mask influence of crust deformation in evaporation board, Improve OLED PPI grade, improve producing line yield；High film forming stability energy, ensure that material is being applied to OLED device During use after part, keep film morphology, do not formed local-crystalized, cause device electrode short circuit, improving OLED makes Use the life-span.
The OLED material describing present invention synthesis in detail below by way of device embodiments 1～10 and comparative example 1 is in the devices Application effect as emitting layer material.Device embodiments 2～10 of the present invention, comparative example 1 institute compared with device embodiments 1 The processing technology stating device is identical, and employed identical baseplate material and electrode material, the thickness of electrode material Also it is consistent, except that the material of main part of the luminescent layer 5 in 2～9 pairs of devices of device converts；Device 10 is using this Invent described material as hole transport/electronic barrier layer application.The performance test results of each embodiment obtained device such as table 2 institute Show.
Device embodiments 1
A kind of electroluminescent device, its preparation process includes：
A) the ito anode layer 2 on cleaning transparent substrate layer 1, deionized water, acetone, EtOH Sonicate cleaning each 15 respectively Minute, then process 2 minutes in plasma cleaner；
B) on ito anode layer 2, hole injection layer material HAT-CN is deposited with by vacuum evaporation mode, thickness is 10nm, This layer is as hole injection layer 3；
C) on hole injection layer 3, hole mobile material NPB is deposited with by vacuum evaporation mode, thickness is 80nm, this layer For hole transmission layer/electronic barrier layer 4；
D) it is deposited with luminescent layer 5 on hole transport/electronic barrier layer 4, the compounds of this invention 5 is used as main body Material, Ir (ppy)3As dopant material, material doped mass ratio is 10%, and thickness is 30nm；
E) on luminescent layer 5, electron transport material TPBI is deposited with by vacuum evaporation mode, thickness is 40nm, this layer Organic material uses as hole barrier/electron transfer layer 6；
F) on hole barrier/electron transfer layer 6, vacuum evaporation electron injecting layer LiF, thickness is 1nm, and this layer is electricity Sub- implanted layer 7；
G) on electron injecting layer 7, vacuum evaporation negative electrode Mg：Ag/Ag layer, Mg:Ag doping ratio is 9:1, thickness 15nm, Ag thickness 3nm, this layer is negative electrode reflection electrode layer 8；
Complete the making of electroluminescent device according to above-mentioned steps after, the current efficiency of measurement device and life-span, its result It is shown in Table 2.The molecular machinery formula of associated materials is as follows：
Device embodiments 2
The present embodiment is with the difference of device embodiments 1：The luminescent layer material of main part of electroluminescent device is changed into The compounds of this invention 8, dopant material is Ir (ppy)3, doping mass ratio is 10%, the detection data of gained electroluminescent device It is shown in Table 2.
Device embodiments 3
The present embodiment is with the difference of device embodiments 1：The luminescent layer material of main part of electroluminescent device is changed into The compounds of this invention 12, dopant material is Ir (ppy)3, doping mass ratio is 10%, the detection data of gained electroluminescent device It is shown in Table 2.
Device embodiments 4
The present embodiment is with the difference of device embodiments 1：The luminescent layer material of main part of electroluminescent device is changed into The compounds of this invention 8 and compound GHN, dopant material is Ir (ppy)3, the blending mass ratio of three kinds of materials is 60:30:10, institute The detection data obtaining electroluminescent device is shown in Table 2.
Device embodiments 5
The present embodiment is with the difference of device embodiments 1：The luminescent layer material of main part of electroluminescent device is changed into The compounds of this invention 48 and compound GHN, dopant material is Ir (ppy)3, the blending mass ratio of three kinds of materials is 60:30:10, The detection data of gained electroluminescent device is shown in Table 2.
Device embodiments 6
The present embodiment is with the difference of device embodiments 1：The luminescent layer material of main part of electroluminescent device is changed into The compounds of this invention 56 and compound GHN, dopant material is Ir (ppy)3, the blending mass ratio of three kinds of materials is 60:30:10, The detection data of gained electroluminescent device is shown in Table 2.
Device embodiments 7
The present embodiment is with the difference of device embodiments 1：The luminescent layer material of main part of electroluminescent device is changed into The compounds of this invention 58 and compound GHN, dopant material is Ir (ppy)3, the blending mass ratio of three kinds of materials is 60:30:10, The detection data of gained electroluminescent device is shown in Table 2.
Device embodiments 8
The present embodiment is with the difference of device embodiments 1：The luminescent layer material of main part of electroluminescent device is changed into The compounds of this invention 66 and compound GHN, dopant material Ir (ppy)3, the blending mass ratio of three kinds of materials is 60:30:10, institute The detection data obtaining electroluminescent device is shown in Table 2.
Device embodiments 9
The present embodiment is with the difference of device embodiments 1：The luminescent layer material of main part of electroluminescent device is changed into The compounds of this invention 70 and compound GHN, dopant material is Ir (ppy)3, the blending mass ratio of three kinds of materials is 60:30:10, The detection data of gained electroluminescent device is shown in Table 2.
Device embodiments 10
The present embodiment is with the difference of device embodiments 1：Hole transport/the electronic barrier layer of electroluminescent device 4 material is changed into the compounds of this invention 46, and the material of main part of luminescent layer 5 is known compound CBP, and dopant material is Ir (ppy)3, doping mass ratio is 10%, and the detection data of gained electroluminescent device is shown in Table 2.
Device comparative example 1
The present embodiment is with the difference of device embodiments 1：The luminescent layer material of main part of electroluminescent device is changed into Known compound CBP, the detection data of gained electroluminescent device is shown in Table 2.
Table 2
Note：Using device comparative example 1 as reference, comparative example 1 device property indices are set to 1.0 to device detection performance. The current efficiency of comparative example 1 is 28cd/A (@10mA/cm2)；CIE chromaticity coordinates is (0.33,0.63)；The LT95 longevity under 5000 brightness Life decays to 2.5Hr.
Can be seen that the machine compound containing xanthene structure of the present invention can be applicable to OLED and lights by the result of table 2 Element manufacturing, and compared with comparative example, either efficiency or life-span all ratio known OLED material larger changes of acquisition, especially It is the larger lifting of the life time decay acquisition of device.
To sum up, the foregoing is only presently preferred embodiments of the present invention, not in order to limit the present invention, all essences in the present invention Within god and principle, any modification, equivalent substitution and improvement made etc., should be included within the scope of the present invention.

Claims (6)

1. a kind of organic compound containing xanthene is it is characterised in that the general structure such as formula (1) of described compound is shown：
Wherein, Ar1、Ar2It is expressed as phenyl, xenyl or naphthyl；
R1、R2Independently be expressed as structure shown in formula (2)；R1With R2Can be identical or different；R1It is also denoted as hydrogen Atom；
In formula (2), R3、R4Independently be expressed as structure in hydrogen atom, formula (3) or formula (4)；
In formula (3), a is selected fromX1、X2、X3Independently be expressed as oxygen atom, Sulphur atom, selenium atom, C1-10The alkylidene that the alkylidene of straight or branched alkyl replacement, aryl replace, alkyl or aryl replace One of tertiary amine groups；
Formula (3), formula (4) pass through CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL‘1-CL’2Key, CL‘2-CL’3Key or CL‘3-CL’4 Key and formula (2) connect.
2. organic compound according to claim 1 is it is characterised in that described R1、R2Being expressed as independently：
In any one.
3. organic compound according to claim 1 is it is characterised in that the tool of the described organic compound containing xanthene Body structural formula is：
In any one.
4. a kind of preparation method of organic compound described in claim 1 is it is characterised in that work as R1When being expressed as hydrogen atom, preparation During reaction equation be：
Described preparation method is with Br-Ar2- Br is raw material, by grignard reaction, prepared Grignard reagent, and then with xanthenes reactive ketone, Generate the tertiary alcohol, the then tertiary alcohol and H-Ar1Reacted by friedel-craft, a bromo compound, Ran Houhe are obtainedIt is coupled by C-N and described compound is obtained.
5. a kind of preparation method of organic compound described in claim 1 is it is characterised in that work as R1It is expressed as the structure of formula (2) When, the reaction equation in preparation process is：
Described preparation method is with Br-Ar2- Br is raw material, by grignard reaction, prepared Grignard reagent, and then with xanthenes reactive ketone, Generate the tertiary alcohol, the then tertiary alcohol and H-Ar1- Br is reacted by friedel-craft, and two bromo compounds, Ran Houhe are obtainedIt is coupled by C-N and described compound is obtained.
6. a kind of organic electroluminescence device comprising the organic compound containing xanthene described in any one of Claims 1 to 5, It is characterized in that described organic compound is applied between negative electrode and anode as emitting layer material, it is used for preparing organic electroluminescence and sends out Optical diode.
CN201610754307.XA 2016-08-26 2016-08-26 A kind of organic compound containing xanthene and its application Active CN106467526B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201610754307.XA CN106467526B (en) 2016-08-26 2016-08-26 A kind of organic compound containing xanthene and its application

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201610754307.XA CN106467526B (en) 2016-08-26 2016-08-26 A kind of organic compound containing xanthene and its application

Publications (2)

Publication Number Publication Date
CN106467526A true CN106467526A (en) 2017-03-01
CN106467526B CN106467526B (en) 2019-05-24

Family

ID=58229958

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201610754307.XA Active CN106467526B (en) 2016-08-26 2016-08-26 A kind of organic compound containing xanthene and its application

Country Status (1)

Country Link
CN (1) CN106467526B (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107216279A (en) * 2017-06-12 2017-09-29 江苏三月光电科技有限公司 A kind of compound as core using dibenzocycloheptene and its application on organic electroluminescence device
CN107522705A (en) * 2017-09-29 2017-12-29 江苏三月光电科技有限公司 A kind of oxa anthracenes organic compound and its application on OLED
CN107556297A (en) * 2017-09-29 2018-01-09 江苏三月光电科技有限公司 A kind of oxa anthracenes organic compound and its application
CN107652297A (en) * 2017-09-29 2018-02-02 江苏三月光电科技有限公司 A kind of oxa anthracenes organic compound and its application in OLED
WO2018158659A1 (en) * 2017-03-03 2018-09-07 株式会社半導体エネルギー研究所 Organic compound, light-emitting element, light-emitting device, electronic apparatus, and illumination device
CN110372691A (en) * 2018-04-13 2019-10-25 江苏三月光电科技有限公司 It is a kind of using xanthone as the compound of core, preparation method and its application on OLED
KR20200135216A (en) * 2019-05-24 2020-12-02 머티어리얼사이언스 주식회사 An organic compound and an organic light emitting diode
WO2020242165A1 (en) * 2019-05-24 2020-12-03 머티어리얼사이언스 주식회사 Organic compound and organic electric field light-emitting device comprising same
US11124521B2 (en) 2018-04-11 2021-09-21 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
CN113444097A (en) * 2021-08-30 2021-09-28 浙江华显光电科技有限公司 Tri-carbazole derivative, organic photoelectric device, and display or lighting device

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010061315A1 (en) * 2008-11-26 2010-06-03 Philips Intellectual Property & Standards Gmbh Oled with novel hole-conducting material
WO2013149958A1 (en) * 2012-04-02 2013-10-10 Novaled Ag Use of a semiconducting compound in an organic light emitting device
WO2015099438A1 (en) * 2013-12-27 2015-07-02 주식회사 두산 Organic light-emitting compound and organic electroluminescent element using same
CN104781247A (en) * 2012-11-12 2015-07-15 默克专利有限公司 Materials for electronic devices
CN105630101A (en) * 2014-11-26 2016-06-01 鸿富锦精密工业(武汉)有限公司 Electronic device shell and electronic device

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010061315A1 (en) * 2008-11-26 2010-06-03 Philips Intellectual Property & Standards Gmbh Oled with novel hole-conducting material
WO2013149958A1 (en) * 2012-04-02 2013-10-10 Novaled Ag Use of a semiconducting compound in an organic light emitting device
CN104781247A (en) * 2012-11-12 2015-07-15 默克专利有限公司 Materials for electronic devices
WO2015099438A1 (en) * 2013-12-27 2015-07-02 주식회사 두산 Organic light-emitting compound and organic electroluminescent element using same
CN105630101A (en) * 2014-11-26 2016-06-01 鸿富锦精密工业(武汉)有限公司 Electronic device shell and electronic device

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018158659A1 (en) * 2017-03-03 2018-09-07 株式会社半導体エネルギー研究所 Organic compound, light-emitting element, light-emitting device, electronic apparatus, and illumination device
JPWO2018158659A1 (en) * 2017-03-03 2020-02-06 株式会社半導体エネルギー研究所 Organic compounds, light-emitting elements, light-emitting devices, electronic devices, and lighting devices
JP7175259B2 (en) 2017-03-03 2022-11-18 株式会社半導体エネルギー研究所 organic compounds, light-emitting elements, light-emitting devices, electronic devices, and lighting devices
CN107216279B (en) * 2017-06-12 2020-07-17 中节能万润股份有限公司 Compound with dibenzosuberene as core and application thereof in organic electroluminescent device
CN107216279A (en) * 2017-06-12 2017-09-29 江苏三月光电科技有限公司 A kind of compound as core using dibenzocycloheptene and its application on organic electroluminescence device
CN107522705A (en) * 2017-09-29 2017-12-29 江苏三月光电科技有限公司 A kind of oxa anthracenes organic compound and its application on OLED
CN107556297A (en) * 2017-09-29 2018-01-09 江苏三月光电科技有限公司 A kind of oxa anthracenes organic compound and its application
CN107652297A (en) * 2017-09-29 2018-02-02 江苏三月光电科技有限公司 A kind of oxa anthracenes organic compound and its application in OLED
US11124521B2 (en) 2018-04-11 2021-09-21 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
CN110372691A (en) * 2018-04-13 2019-10-25 江苏三月光电科技有限公司 It is a kind of using xanthone as the compound of core, preparation method and its application on OLED
CN110372691B (en) * 2018-04-13 2021-10-22 江苏三月科技股份有限公司 Compound with xanthone as core, preparation method thereof and application thereof in OLED
KR20200135216A (en) * 2019-05-24 2020-12-02 머티어리얼사이언스 주식회사 An organic compound and an organic light emitting diode
KR102249719B1 (en) 2019-05-24 2021-05-10 머티어리얼사이언스 주식회사 An organic compound and an organic light emitting diode
CN113795498A (en) * 2019-05-24 2021-12-14 材料科学有限公司 Organic compound and organic electroluminescent element comprising same
WO2020242165A1 (en) * 2019-05-24 2020-12-03 머티어리얼사이언스 주식회사 Organic compound and organic electric field light-emitting device comprising same
CN113444097A (en) * 2021-08-30 2021-09-28 浙江华显光电科技有限公司 Tri-carbazole derivative, organic photoelectric device, and display or lighting device

Also Published As

Publication number Publication date
CN106467526B (en) 2019-05-24

Similar Documents

Publication Publication Date Title
CN106467526B (en) A kind of organic compound containing xanthene and its application
CN106467486A (en) A kind of organic compound containing dimethylanthracene and its application
CN106478611B (en) It is a kind of using xanthene as the organic compound of core and its application
CN106220619B (en) A kind of organic compound containing xanthene structure and its application
CN105837498B (en) Organic compound containing dimethylanthracene structure and application thereof
CN106478610B (en) A kind of organic compound containing xanthene and its application in OLED device
CN107057681A (en) A kind of photoelectric material containing xanthene structure and its application in OLED fields
CN107868030B (en) Organic compound containing fluorene and application thereof in organic electroluminescent device
CN106674210A (en) Organic compounds using homobenzenes as core and application thereof in organic electroluminescent devices
CN109824684B (en) Spirofluorene derivative organic compound and application thereof in organic electroluminescent device
CN107056809B (en) It a kind of organic compound containing dimethylanthracene and its is applied on organic electroluminescence device
CN106220649A (en) Diaryl ketone-based compound and application thereof in organic electroluminescent device
CN108129386A (en) Swash complex luminescent material and its application in organic electroluminescence device is prepared to receptor type intramolecular base based on break-in conjugated
CN110294663B (en) Compound with anthracene as core and application thereof in organic electroluminescent device
CN109956962A (en) It is a kind of fluorene structured for the compound of parent nucleus and its application on organic electroluminescence device with azaspiro
CN107778220A (en) Compound and application in an organic light emitting device using fluorenes and nitrogenous hexa-member heterocycle as core
CN107056737B (en) Photoelectric material containing dimethyl anthracene structure and application thereof
CN107573329A (en) A kind of organic compound based on triazine and quinoxaline and its application on organic electroluminescence device
CN107868048A (en) A kind of compound containing fluorenes and its application
CN107056763A (en) A kind of electroluminescent organic material and its application using xanthene as core
CN107056820B (en) A kind of compound based on 9,10- anthraquinone and its application on organic electroluminescence device
CN107602397B (en) Compound with dibenzosuberene as core and application thereof
CN106543071B (en) Compound with dibenzoheptenone as core and application of compound in OLED
CN110577488A (en) Compound with carbazole as core and application thereof in organic electroluminescent device
CN106800526B (en) It is a kind of using cyclic diketones as the electroluminescent organic material of core and its application

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
TR01 Transfer of patent right
TR01 Transfer of patent right

Effective date of registration: 20200213

Address after: 264006 No. 11 Wuzhishan Road, Yantai economic and Technological Development Zone, Shandong

Patentee after: VALIANT Co.,Ltd.

Address before: 214112 No. 210, Xinzhou Road, New District, Jiangsu, Wuxi

Patentee before: JIANGSU SUNERA TECHNOLOGY Co.,Ltd.

PE01 Entry into force of the registration of the contract for pledge of patent right

Denomination of invention: An organic compound containing oxaanthracene and its application

Effective date of registration: 20211202

Granted publication date: 20190524

Pledgee: Yantai Branch of China Merchants Bank Co.,Ltd.

Pledgor: VALIANT Co.,Ltd.

Registration number: Y2021980013807

PE01 Entry into force of the registration of the contract for pledge of patent right
PC01 Cancellation of the registration of the contract for pledge of patent right

Date of cancellation: 20220823

Granted publication date: 20190524

Pledgee: Yantai Branch of China Merchants Bank Co.,Ltd.

Pledgor: VALIANT Co.,Ltd.

Registration number: Y2021980013807

PC01 Cancellation of the registration of the contract for pledge of patent right
TR01 Transfer of patent right

Effective date of registration: 20221021

Address after: 214112 No.210 Xinzhou Road, Wuxi City, Jiangsu Province

Patentee after: Jiangsu March Technology Co.,Ltd.

Address before: 264006 No. 11 Wuzhishan Road, Yantai economic and Technological Development Zone, Shandong

Patentee before: VALIANT Co.,Ltd.

TR01 Transfer of patent right