CN106467526B - 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
CN106467526B
CN106467526B CN201610754307.XA CN201610754307A CN106467526B CN 106467526 B CN106467526 B CN 106467526B CN 201610754307 A CN201610754307 A CN 201610754307A CN 106467526 B CN106467526 B CN 106467526B
Authority
CN
China
Prior art keywords
general formula
organic compound
compound
preparation
expressed
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN201610754307.XA
Other languages
Chinese (zh)
Other versions
CN106467526A (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 materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent 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

本发明公开了一种含有氧杂蒽的有机化合物及其应用，该有机化合物的结构式通式如通式(1)所示。本发明提供的有机化合物玻璃化温度高，分子热稳定性强，具有合适的HOMO和LUMO能级和较高的Eg，通过器件结构优化，可有效提升OLED器件的光电性能以及OLED器件的寿命。

The invention discloses an organic compound containing xanthene and an application thereof. The general structural formula of the organic compound is shown in the general formula (1). The organic compound provided by the invention has high glass transition temperature, strong molecular thermal stability, suitable HOMO and LUMO energy levels and high Eg, and can effectively improve the optoelectronic performance of the OLED device and the life of the OLED device by optimizing the device structure.

Description

A kind of organic compound containing xanthene and its application
Technical field
The present invention relates to organic photoelectrical material technical fields, and containing xanthene structure more particularly, to one kind is center skeleton Compound-material and its application in the field OLED.
Background technique
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology can both be used to make New display product is made, production novel illumination product is can be used for, is expected to substitute existing liquid crystal display and fluorescent lighting, Application prospect is very extensive.
Structure of the OLED luminescent device like sandwich, including electrode material film layer, and be clipped in Different electrodes film layer it Between organic functional material, various different function materials are overlapped mutually depending on the application collectively constitutes OLED luminescent device together. As current device, when the two end electrodes application 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 further compound in luminescent layer, i.e. generation OLED electroluminescent.
Currently, OLED display technology in smart phone, applied by the fields such as tablet computer, further will also be to electricity Depending on etc. large scales application field extension, still with actual products application require compare, the luminous efficiency of OLED device, use The performances such as service life also need further to be promoted.
Proposing high performance research for OLED luminescent device includes: the driving voltage for reducing device, improves shining for device Efficiency improves the service life etc. of device.In order to realize OLED device performance continuous promotion, not only need from OLED device The innovation of structure and manufacture craft is constantly studied and is innovated with greater need for oled light sulfate ferroelectric functional material, formulates out higher performance OLED Functional material.
Oled light sulfate ferroelectric functional material applied to OLED device can be divided into two major classes, i.e. charge injection transmission from purposes Material and luminescent material further can also 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 that various organic functional materials have good photoelectric characteristic, For example, as charge transport materials, it is desirable that have good carrier mobility, high-vitrification conversion temperature etc., as luminous The material of main part of layer requires material to have good bipolarity, HOMO/LUMO energy rank appropriate etc..
The oled light sulfate ferroelectric functional material film layer for constituting OLED device includes at least two layers or more structure, applies in industry OLED device structure then includes hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electronics biography A variety of film layers such as defeated layer, electron injecting layer, that is to say, that the photoelectric functional material applied to OLED device is infused including at least hole Enter material, hole mobile material, luminescent material, electron transport material etc., material type and collocation form with rich and more The characteristics of sample.In addition, used photoelectric functional material has stronger for the collocation of the OLED device of different structure Selectivity, performance of the identical material in different structure device, it is also possible to completely totally different.
Therefore, for the industry application requirement of current OLED device and the different function film layer of OLED device, device Photoelectric characteristic demand, it is necessary to which selection is more suitable for, and OLED functional material or combination of materials with high performance are just able to achieve device High efficiency, the overall characteristic of long-life and low-voltage.For current OLED shows the actual demand of Lighting Industry, OLED at present The development of material is also far from enough, lags behind the requirement of panel manufacturing enterprise, as the organic of material enterprise development higher performance Functional material is particularly important.
Summary of the invention
In view of the above-mentioned problems existing in the prior art, the applicant provide a kind of organic compound containing xanthene and It is applied on organic electroluminescence device.Organic compound glass transition temperature provided by the invention is high, and molecule thermal stability is strong, With suitable HOMO and lumo energy and higher Eg, optimized by device architecture, can effectively promote the photoelectricity of OLED device The service life of performance and OLED device.
Technical scheme is as follows:
The applicant provides a kind of organic compound containing xanthene, the general structure of the compound such as general formula (1) shown in:
Wherein, Ar1、Ar2It is expressed as phenyl, xenyl or naphthalene；
R1、R2Independently be expressed as structure shown in general formula (2)；R1With R2It can be identical or different；R1It also may indicate that For hydrogen atom；
In general formula (2), R3、R4Independently be expressed as hydrogen atom, structure in general formula (3) or general formula (4)；
In general formula (3), a is selected fromX1、X2、X3Independently be expressed as oxygen Atom, sulphur atom, selenium atom, C1-10Alkylidene, the alkyl or aryl of alkylidene, aryl substitution that linear or branched alkyl group replaces One of substituted tertiary amine groups；
General formula (3), general formula (4) pass through CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL‘1-CL’2Key, CL‘2-CL’3Key or CL‘3-CL’4Key and general formula (2) connection.
Preferably, the R1、R2Expression independently are as follows:
In any one.
Preferably, the concrete structure formula of the organic compound containing xanthene are as follows:
Any one of.
The applicant additionally provides a kind of preparation method of organic compound, works as R1When being expressed as hydrogen atom, preparation Reaction equation in the process is:
The preparation method is with Br-Ar2- Br is raw material, and by grignard reaction, Grignard Reagent is made, then with xanthenes reactive ketone, The tertiary alcohol is generated, then the tertiary alcohol and H-Ar1Reacted by friedel-craft, be made a bromo compound, then and The compound is made by C-N coupling.
The applicant additionally provides the preparation method of another organic compound, works as R1It is expressed as the knot of general formula (2) When structure, the reaction equation in preparation process is:
The preparation method is with Br-Ar2- Br is raw material, and by grignard reaction, Grignard Reagent is made, raw then with xanthenes reactive ketone At the tertiary alcohol, the then tertiary alcohol and H-Ar1- Br by friedel-craft react, be made two bromo compounds, then and The compound is made by C-N coupling.
The applicant additionally provides a kind of organic electroluminescence device comprising the organic compound containing xanthene, The organic compound is applied between cathode and anode as emitting layer material, is used to prepare organic electroluminescent LED.
The present invention is beneficial to be had the technical effect that
For the compounds of this invention using xanthene as parent nucleus, connected symmetrical dendrimer or asymmetrical rigid radical destroy the crystallization of molecule Property, intermolecular aggtegation is avoided, there is high glass transition temperature, material is in OLED device in application, high film can be kept Layer stability, improves OLED device service life.
The compounds of this invention structure balances electrons and holes more in the distribution of luminescent layer, in appropriate HOMO energy level Under, improve hole injection/transmission performance；Under suitable lumo energy, and play the role of electronic blocking, promotes exciton Combined efficiency in luminescent layer；When light emitting functional layer materials'use as OLED luminescent device, xanthene that aryl replaces Branch in the collocation scope of the invention can effectively improve exciton utilization rate and high fluorescent radiation efficiency, reduce under high current density Efficiency roll-off reduces device voltage, improves current efficiency and the service life of device.
The special construction of compound of the present invention designs, so that material also has while with high decomposition temperature Low sublimation temperature or vacuum evaporation temperature, temperature difference window with higher between sublimation temperature or vapor deposition temperature and decomposition temperature Mouthful, so that material operation controllability with higher in industrial application, is conducive to the application of material volume production.
Compound of the present invention has good application effect in OLED luminescent device, before having good industrialization Scape.
Detailed description of the invention
Fig. 1 is the structural schematic diagram that material cited by the present invention is applied to OLED device；
Wherein, 1 is transparent substrate layer, and 2 be ito anode layer, and 3 be hole injection layer, and 4 be hole transport/electronic barrier layer, 5 be luminescent layer, and 6 be electron-transport/hole blocking layer, and 7 be electron injecting layer, and 8 be cathode 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 for being passed through nitrogen, be added 11.8g Isosorbide-5-Nitrae-dibromobenzene (0.05mol) and 1.33gMg powder (0.055mol), 60ml tetrahydrofuran are heated to reflux 4 hours, fully reacting, generate grignard reagent；
10.8g Oxoxanthone (0.05mol) is dissolved in 50ml tetrahydrofuran, and above-mentioned grignard reagent is added dropwise, and 60 DEG C of reactions 24 are small When, a large amount of white precipitates are generated, saturation NHCl is eventually adding4Alcohol is converted by format salt；After completion of the reaction, ether extracts, and does Dry revolving, petroleum ether: methylene chloride mixed solvent (3:2) silica gel column purification, obtaining the solid tertiary alcohol of yellowish, (yield is 85%)；The compound, molecular formula C are identified using DEI-MS19H13BrO2, detected value [M+1]+=354.08, calculated value 353.21；
By 1:2 when the measurement above-mentioned tertiary alcohol of 14.1g (0.04mol) and 12.5g bromobenzene (0.08mol) are dissolved in 100ml dichloromethane In alkane, 8ml boron trifluoride etherate is added dropwise at room temperature, reacts 30 minutes, 20ml ethyl alcohol and 20ml water is added Quenching reaction is extracted with methylene chloride (20ml*3), and dry revolving, petroleum ether silica gel column purification is tied again with ethyl alcohol: methylene chloride Crystalline substance, yield 72%；The compound, molecular formula C are identified 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:
Raw material A 2 is prepared by the synthetic method of raw material A1 in embodiment 1, difference is to replace compound with 1,1 '-biphenyl Bromobenzene；
The compound, molecular formula C are identified using DEI-MS31H21BrO, detected value [M+1]+=490.05, calculated value 489.40。
Embodiment 3: the synthesis of raw material A 3:
Synthetic route:
Raw material A 3 is prepared by the synthetic method of raw material A1 in embodiment 1, difference is to be replaced in third step reaction with benzene Bromobenzene；
The compound, molecular formula C are identified using DEI-MS25H17BrO, detected value [M+1]+=414.02, calculated value 413.31。
Embodiment 4: the synthesis of raw material A 4:
Synthetic route:
Raw material A 4 is prepared by the synthetic method of raw material A1 in embodiment 1, difference is to be replaced in third step reaction with naphthalene Bromobenzene；
The compound, molecular formula C are identified using DEI-MS29H19BrO, detected value [M+1]+=463.97, calculated value 463.36。
Embodiment 5: the synthesis of compound 1:
Synthetic route:
In the there-necked flask of 250ml, lead under 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 × 10-4It is small to be heated to reflux 24 for mol tri-tert phosphorus, 150ml toluene When, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving, column chromatograph to obtain target product, HPLC purity 99.7%, yield 71.3%；
Elemental analysis 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 664.79 surveys molecular weight 665.03.
Embodiment 6: the synthesis of compound 2:
Synthetic route:
In the there-necked flask of 250ml, lead under 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 are heated to reflux 24 Hour, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving, column chromatograph to obtain target product, HPLC purity 99.1%, yield 75.3%；
Elemental analysis 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 675.81 surveys molecular weight 676.04.
Embodiment 7: the synthesis of compound 8:
Synthetic route:
In the there-necked flask of 250ml, lead under 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 are heated to reflux 24 Hour, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving, column chromatograph to obtain target product, HPLC purity 99.1%, yield 72.5%；
Elemental analysis 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 664.79 surveys molecular weight 665.08.
Embodiment 8: the synthesis of compound 10:
Synthetic route:
In the there-necked flask of 250ml, lead under 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 are heated to reflux 24 Hour, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving, column chromatograph to obtain target product, HPLC purity 98.7%, yield 73.6%；
Elemental analysis 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 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；
Elemental analysis 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 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；
Elemental analysis 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 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 with raw material F1 generation for raw material D1；
Elemental analysis 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 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；
Elemental analysis 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 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；
Elemental analysis 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 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；
Elemental analysis 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 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；
Elemental analysis 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 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；
Elemental analysis 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 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；
Elemental analysis 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 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；
Elemental analysis 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 888.06 surveys molecular weight 888.44.
The compounds of this invention uses in luminescent device, can be used as hole transport/electronic blocking layer material, can also make For luminescent layer Subjective and Objective materials'use.The compounds of this invention is in application with high operability and practicability, major embodiment For with high glass transition temperature, low sublimation temperature, high decomposition temperature and film forming stability.
To the compounds of this invention 8, compound 32, compound 48, current material CBP carry out respectively hot property, luminescent spectrum, The test of HOMO energy level, testing result are as shown in table 1.
Table 1
Note: glass transition temperature Tg is by differential scanning calorimetry (DSC, German Nai Chi company DSC204F1 differential scanning calorimetry Instrument) measurement, 10 DEG C/min of heating rate；It is using SUNIC evaporated device, vacuum degree < 1E-5Pa, material rate that temperature, which is deposited, ForWhen vapor deposition temperature；Thermal weight loss temperature Td is the temperature of the weightlessness 1% in nitrogen atmosphere, in Japanese Shimadzu Corporation It is measured on TGA-50H thermogravimetric analyzer, nitrogen flow 20mL/min；Film forming stability refers to, utilizes SUNIC evaporator Platform, material be deposited on glass substrate at 100nm thickness thin film, the envelope in glove box environment (the equal < 1PPm of water oxygen content) Dress, glass sample (humidity 80%, 80 DEG C of temperature) under the conditions of double 80 places test 240 hours after encapsulation, with 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 Emit spectrometer (AC-2 type PESA) test, tests as atmospheric environment.
By upper table data it is found that the compounds of this invention has adjustable HOMO energy level, it is suitable as different function layer material It uses；Low vapor deposition temperature can make material in industrial application, reduce heat radiation to vapor deposition board in Fine-mask influence of crust deformation, OLED device PPI grade is improved, producing line yield is improved；High film forming stability energy can guarantee that material is being applied to OLED device In use process after part, film morphology is kept, is not formed local-crystalized, causes device electrode short-circuit, improving OLED device makes Use the service life.
In the devices below by way of device embodiments 1~10 and comparative example 1 OLED material that the present invention will be described in detail synthesizes Application effect as emitting layer material.Device embodiments 2~10 of the present invention, the institute compared with device embodiments 1 of comparative example 1 The manufacture craft for stating device is identical, and uses identical baseplate material and electrode material, the film 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 uses this The material is invented as hole transport/electronic barrier layer application.The performance test results of each embodiment obtained device such as 2 institute of table Show.
Device embodiments 1
A kind of electroluminescent device, preparation step include:
A) the ito anode layer 2 on transparent substrate layer 1 is cleaned, cleans each 15 with deionized water, acetone, EtOH Sonicate respectively Minute, then handled 2 minutes in plasma cleaner；
B) on ito anode layer 2, hole injection layer material HAT-CN is deposited by vacuum evaporation mode, with a thickness of 10nm, This layer is as hole injection layer 3；
C) on hole injection layer 3, hole mobile material NPB is deposited by vacuum evaporation mode, with a thickness of 80nm, the layer For hole transmission layer/electronic barrier layer 4；
D) luminescent layer 5 is deposited on hole transport/electronic barrier layer 4, uses the compounds of this invention 5 as main body Material, Ir (ppy)3As dopant material, material doped mass ratio is 10%, with a thickness of 30nm；
E) on luminescent layer 5, electron transport material TPBI is deposited by vacuum evaporation mode, with a thickness of 40nm, this layer Organic material is used as hole barrier/electron transfer layer 6；
F) on hole barrier/electron transfer layer 6, vacuum evaporation electron injecting layer LiF, with a thickness of 1nm, which is electricity Sub- implanted layer 7；
G) on electron injecting layer 7, Mg:Ag/Ag layers of vacuum evaporation cathode, Mg:Ag doping ratio is 9:1, thickness 15nm, Ag thickness 3nm, the layer are cathode reflection electrode layer 8；
After the production for completing electroluminescent device according to above-mentioned steps, the current efficiency of measurement device and service life, result It is shown in Table 2.The molecular machinery formula of associated materials is as follows:
Device embodiments 2
The present embodiment and device embodiments 1 the difference is that: the luminescent layer material of main part of electroluminescent device becomes The compounds of this invention 8, dopant material are 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 and device embodiments 1 the difference is that: the luminescent layer material of main part of electroluminescent device becomes The compounds of this invention 12, dopant material are 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 and device embodiments 1 the difference is that: the luminescent layer material of main part of electroluminescent device becomes The compounds of this invention 8 and compound GHN, dopant material are Ir (ppy)3, the blending mass ratio of three kinds of materials is 60:30:10, institute The detection data for obtaining electroluminescent device is shown in Table 2.
Device embodiments 5
The present embodiment and device embodiments 1 the difference is that: the luminescent layer material of main part of electroluminescent device becomes The compounds of this invention 48 and compound GHN, dopant material are 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 and device embodiments 1 the difference is that: the luminescent layer material of main part of electroluminescent device becomes The compounds of this invention 56 and compound GHN, dopant material are 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 and device embodiments 1 the difference is that: the luminescent layer material of main part of electroluminescent device becomes The compounds of this invention 58 and compound GHN, dopant material are 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 and device embodiments 1 the difference is that: the luminescent layer material of main part of electroluminescent device becomes 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 for obtaining electroluminescent device is shown in Table 2.
Device embodiments 9
The present embodiment and device embodiments 1 the difference is that: the luminescent layer material of main part of electroluminescent device becomes The compounds of this invention 70 and compound GHN, dopant material are 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 and device embodiments 1 the difference is that: hole transport/electronic barrier layer of electroluminescent device 4 material becomes the compounds of this invention 46, and the material of main part of luminescent layer 5 is known compound CBP, dopant material 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 and device embodiments 1 the difference is that: the luminescent layer material of main part of electroluminescent device becomes The detection data of known compound CBP, gained electroluminescent device are shown in Table 2.
Table 2
Note: for device detection performance using device comparative example 1 as reference, 1 device performance indexes of comparative example is set as 1.0. 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.
It can be seen that the machine compound of the present invention containing xanthene structure can be applied to OLED and shine by the result of table 2 Element manufacturing, and compared with comparative example, either efficiency or service life obtain larger change than known OLED material, especially It is the biggish promotion of life time decay acquisition of device.
To sum up, the foregoing is merely presently preferred embodiments of the present invention, is not intended to limit the invention, all in essence of the invention Within mind and principle, any modification, equivalent replacement, improvement and so on be should all be included in the protection scope of the present invention.

Claims (6)

1. a kind of organic compound containing xanthene, it is characterised in that shown in the general structure of the compound such as general formula (1):
Wherein, Ar1、Ar2It is expressed as phenyl, xenyl or naphthalene；
R1、R2Independently be expressed as structure shown in general formula (2)；R1With R2It can be identical or different；R1It is also denoted as hydrogen Atom；
In general formula (2), R3、R4Independently be expressed as hydrogen atom, structure in general formula (3) or general formula (4)；
In general formula (3), a is selected fromX1、X2、X3Independently be expressed as oxygen atom, One of the tertiary amine groups that sulphur atom, selenium atom, the methylene of dimethyl substitution, methyl substituted tertiary amine groups, phenyl replace；
General formula (3), general 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 general formula (2) connection.
2. organic compound according to claim 1, it is characterised in that the R1、R2Expression independently are as follows:
In any one.
3. organic compound according to claim 1, it is characterised in that the tool of the organic compound containing xanthene Body structural formula are as follows:
Any one of.
4. a kind of preparation method of organic compound described in claim 1, which is characterized in that work as R1When being expressed as hydrogen atom, preparation Reaction equation in the process is:
The preparation method is with Br-Ar2- Br is raw material, and by grignard reaction, Grignard Reagent is made, then with xanthenes reactive ketone, The tertiary alcohol is generated, then the tertiary alcohol and H-Ar1Reacted by friedel-craft, be made a bromo compound, then and The compound is made by C-N coupling.
5. a kind of preparation method of organic compound described in claim 1, which is characterized in that work as R1It is expressed as the structure of general formula (2) When, the reaction equation in preparation process is:
The preparation method is with Br-Ar2- Br is raw material, and by grignard reaction, Grignard Reagent is made, raw then with xanthenes reactive ketone At the tertiary alcohol, the then tertiary alcohol and H-Ar1- Br by friedel-craft react, be made two bromo compounds, then and The compound is made by C-N coupling.
6. a kind of organic electroluminescence device comprising the organic compound described in any one of Claims 1 to 5 containing xanthene, It is characterized in that the organic compound is applied between cathode and anode as emitting layer material, it is used to prepare organic electroluminescence hair 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 CN106467526A (en) 2017-03-01
CN106467526B true 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)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
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
CN107522705B (en) * 2017-09-29 2020-12-11 中节能万润股份有限公司 Xanthene organic compound and application thereof in OLED
CN107556297B (en) * 2017-09-29 2020-09-04 中节能万润股份有限公司 Xanthene organic compound and application thereof
KR20190118821A (en) 2018-04-11 2019-10-21 삼성전자주식회사 Condensed cyclic compound and organic light-emitting device including the same
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
CN113795498B (en) * 2019-05-24 2024-12-17 材料科学有限公司 Organic compound and organic electroluminescent element comprising same
KR102249719B1 (en) * 2019-05-24 2021-05-10 머티어리얼사이언스 주식회사 An organic compound and an organic light emitting diode
KR102890854B1 (en) * 2019-08-12 2025-11-27 삼성디스플레이 주식회사 Organic electroluminescence device and fused polycyclic compound for organic electroluminescence device
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

Also Published As

Publication number Publication date
CN106467526A (en) 2017-03-01

Similar Documents

Publication Publication Date Title
CN106467526B (en) A kind of organic compound containing xanthene and its application
CN107021926B (en) Compound containing azaspirofluorene and nitrogen-containing six-membered heterocycle and application of compound in OLED
CN110294663B (en) Compound with anthracene as core and application thereof in organic electroluminescent device
CN106467486B (en) Organic compound containing dimethylanthracene and application thereof
CN106220619B (en) A kind of organic compound containing xanthene structure and its application
CN105837498B (en) Organic compound containing dimethylanthracene structure and application thereof
CN109449304A (en) A kind of organic compound based on triazine and benzimidazole and its application on organic electroluminescence device
CN107868048B (en) Fluorene-containing compound and application thereof
CN107868030B (en) Organic compound containing fluorene and application thereof in organic electroluminescent device
CN106478611B (en) It is a kind of using xanthene as the organic compound of core and its application
CN109467511A (en) A kind of aromatic amine compounds and its organic luminescent device
CN107056809B (en) An organic compound containing dimethyl anthracene and its application in organic electroluminescent devices
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
CN107056763A (en) A kind of electroluminescent organic material and its application using xanthene as core
CN110642732B (en) Organic compound containing spirofluorene anthrone structure and application thereof
CN107056807B (en) It is a kind of using equal benzene as the compound of core and its application in organic electroluminescence device
CN110577523B (en) Compound containing triarylamine structure and organic electroluminescent device prepared from compound
CN110655504B (en) Compound with dibenzosuberene as core and application thereof in organic electroluminescent device
CN107216279B (en) Compound with dibenzosuberene as core and application thereof in organic electroluminescent device
CN109912592B (en) Compound containing pyridoindole and application of compound in organic electroluminescent device
CN106800526B (en) It is a kind of using cyclic diketones as the electroluminescent organic material of core and its application
CN107686487B (en) Dimethyl anthracene organic compound and application thereof in organic electroluminescent device
CN106749320B (en) A kind of benzimidazole simultaneously ketone compounds and its application in OLED device
CN106543071B (en) Compound with dibenzoheptenone as core and application of compound in OLED

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