CN106749200A - Ketone electroluminescent organic material of a kind of chromene 4 and its preparation method and application - Google Patents

Ketone electroluminescent organic material of a kind of chromene 4 and its preparation method and application Download PDF

Info

Publication number
CN106749200A
CN106749200A CN201611153197.8A CN201611153197A CN106749200A CN 106749200 A CN106749200 A CN 106749200A CN 201611153197 A CN201611153197 A CN 201611153197A CN 106749200 A CN106749200 A CN 106749200A
Authority
CN
China
Prior art keywords
organic material
substitution
electroluminescent organic
alkyl
benzopyran
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
CN201611153197.8A
Other languages
Chinese (zh)
Inventor
王元勋
石宇
高自良
巨成良
胡葆华
孙利
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.)
Valiant Co Ltd
Original Assignee
Valiant 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 Valiant Co Ltd filed Critical Valiant Co Ltd
Priority to CN201611153197.8A priority Critical patent/CN106749200A/en
Publication of CN106749200A publication Critical patent/CN106749200A/en
Withdrawn legal-status Critical Current

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
    • C07D405/02—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
    • C07D405/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
    • 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
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/06—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D491/056—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
    • 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
    • C07D498/02—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
    • C07D498/06—Peri-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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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
    • C09K2211/1044—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
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom

Landscapes

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

Abstract

The invention discloses ketone electroluminescent organic material of a kind of chromene 4 and its preparation method and application, the structural formula of above-mentioned electroluminescent organic material isThe ketone electroluminescent organic material of chromene 4 that the present invention is provided is applied in OLED luminescent devices so that the current efficiency of device, power efficiency and external quantum efficiency are greatly improved.The ketone electroluminescent organic material of chromene 4 that the present invention is provided has good application effect, with good industrialization prospect.

Description

A kind of benzopyran-4-one class electroluminescent organic material and preparation method thereof and Using
Technical field
The present invention relates to electroluminescent organic material, more particularly to a kind of benzopyran-4-one class organic electroluminescence material Material and its preparation method and application.
Background technology
Organic Light Emitting Diode (OLED:Organic Light Emission Diodes) turn into very popular both at home and abroad Emerging flat-panel monitor product because when OLED display has self-luminous, wide viewing angle (up to more than 175 °), short reaction Between, high-luminous-efficiency, wide colour gamut, low-work voltage (3-10V), panel thin (being smaller than 1mm) and the characteristic such as rollable.OLED quilts It is likened to star's flat display products of 21 century.As technology is more and more ripe, it is possible to be developed rapidly from now on, future It is limitless.OLED luminous principle is by applying an applied voltage, after hole and electronics overcome interface energy barrier, by anode With negative electrode injection, the LUMO of the HOMO energy ranks and electron transfer layer that respectively enter hole-transporting layer can rank；Then electric charge is additional The interface of hole-transporting layer and electron transfer layer is transferred under the driving of electric field, the energy jump at interface causes that interface has electric charge Accumulation；Electronics, hole in the organic substance for have the characteristics of luminescence in conjunction with, formed an exciton, this exciton is in general ring Border is unstable, will be released energy in the form of light or heat afterwards and returns to stable ground state.Via electronics, hole in conjunction with The excitation state of generation only 25% is in theory singlet excited, and remaining 75% is triplet excited state, by with the shape of phosphorescence or heat Formula revert to ground state.
Organic Light Emitting Diode (OLEDs) large-area flat-plate show and illumination in terms of application cause industrial quarters and The extensive concern of art circle.However, traditional organic fluorescence materials can only be lighted using 25% singlet exciton to be formed is electrically excited, device The internal quantum efficiency of part is relatively low (up to 25%).External quantum efficiency is generally less than 5%, also has with the efficiency of phosphorescent devices very big Gap.Although phosphor material enhances intersystem crossing due to the strong SO coupling in heavy atom center, can effectively using electricity The singlet exciton and Triplet exciton to be formed are excited, makes the internal quantum efficiency of device up to 100%.But phosphor material is present Expensive, stability of material is poor, limits its application in OLEDs the problems such as device efficiency tumbles serious.Hot activation is prolonged Slow fluorescence (TADF) material is the third generation luminous organic material developed after organic fluorescence materials and organic phosphorescent material.Should Class material is typically poor (△ EST) with small singlet-triplet, and triplet excitons can be changed by anti-intersystem crossing It is luminous into singlet exciton.This can make full use of the singlet exciton and triplet excitons for being electrically excited lower formation, device it is interior Quantum efficiency can reach 100%.Meanwhile, material structure is controllable, stable in properties, cheap without precious metal, in OLEDs Field has a extensive future.
Although TADF materials can realize 100% exciton utilization rate in theory, following problem is there are in fact：(1) T1 the and S1 states for designing molecule have strong CT features, very small S1-T1 state energy gaps, although can be realized by TADF processes T1 → S1 states exciton conversion ratio high, but low S1 state radiation transistion speed is also resulted in, consequently it is difficult to have (or realizing) concurrently simultaneously Exciton utilization rate high and fluorescent radiation efficiency high；(2) even if having used doping device to mitigate T exciton concentration quenching effects, greatly Efficiency roll-off is serious at higher current densities for the device of most TADF materials.
For the actual demand of current OLED display Lighting Industries, the development of current OLED material is also far from enough, falls After the requirement of panel manufacturing enterprise, it is particularly important as the organic functional material of material enterprise development higher performance.
The content of the invention
For the above mentioned problem that existing OLED material is present, a kind of benzopyran-4-one class organic electroluminescence hair is now provided Luminescent material and its preparation method and application, it is desirable to provide a kind of electroluminescent organic material with good photoelectric properties, with full The requirement of sufficient panel manufacturing enterprise.
Concrete technical scheme is as follows：
The first aspect of the invention is to provide benzopyran-4-one class electroluminescent organic material, with such spy Levy, above-mentioned electroluminescent organic material is with benzopyran-4-one as parent nucleus, and its structural formula such as formula (I) or formula (II) are shown：
Wherein, R1Selected from C1-6Alkyl；
Wherein, Ar is selected from aromatic group, n=1 or 2, R2Selected from containing substituted base or without substitution baseThe base containing substitution or without substitution baseWherein, X1Selected from oxygen atom, sulphur atom, two (C1-10Straight chained alkyl) substitution season alkyl (or tertiary alkyl), two (C1-10Branched alkyl) substitution season alkyl (or tertiary alkyl), virtue One kind in the tertiary amine groups in season alkyl (or tertiary alkyl), alkyl-substituted tertiary amine groups or aryl substitution of base substitution.
Above-mentioned electroluminescent organic material, also has the feature that, containing substituted base
With the base containing substitutionIt is quilt at least one phenyl ring Ortho position unitary substitution, i.e., above-mentioned substitution base passes through C1-C2、C2-C3、C3-C4、C4- C5、C1'-C2'、C2'-C3'、C3'-C4'Or C4'-C5'It is bonded and connects, wherein, X2、X3、X4Separately selected from oxygen atom, sulphur atom, Selenium atom, two (C1-10Straight chained alkyl) substitution season alkyl (or tertiary alkyl), two (C1-10Branched alkyl) substitution season alkyl (or Tertiary alkyl), aryl substitution season alkyl (or tertiary alkyl), alkyl-substituted tertiary amine groups or aryl substitution tertiary amine groups in one Kind.
Above-mentioned electroluminescent organic material, also has the feature that, Ar be selected from phenyl, dibiphenylyl, terphenyl, One kind in naphthyl, anthryl or phenanthryl.
Above-mentioned electroluminescent organic material, also has the feature that, containing substituted baseIn at least one Quilt on individual phenyl ringSubstitution, andBy C4-C5Or
C4'-C5'It is bonded when connecing, X1And X2Overlap, only take X1Or X2。
Preferably, R2Preferably
In any one.
Preferably, above-mentioned electroluminescent organic material is preferably any one in C1-C104 in the present invention：
It is above some specific structure types, but the benzopyran-4-one class organic electroluminescent provided in the present invention Material is not limited to these listed chemical constitutions, every based on formula (I) or formula (II), and substitution base is all models of definition The compound for enclosing the simple transformation of interior group should all be included.
The second aspect of the invention is to provide the preparation method of above-mentioned electroluminescent organic material, with such spy Levy, including：
To the benzopyran-4-one ring bromo compound, the amine compound that weigh is loaded in reaction bulb, add reaction molten Agent, adds catalyst, part and alkali, under an inert atmosphere, the mixed solution of above-mentioned reactant is reacted into 10- in 95-100 DEG C 24 hours, through cooling, filtering, column chromatography after stopping reacting, obtain above-mentioned electroluminescent organic material.
Above-mentioned electroluminescent organic material, also has the feature that, catalyst is Pd2(dba) 3, also, catalyst It is 0.006-0.02 with the mol ratio of benzopyran-4-one ring bromo compound:1.
Above-mentioned electroluminescent organic material, also has the feature that, benzopyran-4-one ring bromo compound and amine The mol ratio of based compound is 1:2.0-4.0.
Above-mentioned electroluminescent organic material, also has the feature that, alkali is sodium tert-butoxide, also, alkali and benzo pyrrole Mutter -4- ketone ring bromo compounds mol ratio be 1.0-3.0:1.
Above-mentioned electroluminescent organic material, also has the feature that, part be tri-tert phosphorus, also, part with The mol ratio of benzopyran-4-one ring bromo compound is 0.006-0.02:1.
The third aspect of the invention is to provide above-mentioned electroluminescent organic material in organic electroluminescence device is prepared Application.
The fourth aspect of the invention is to provide a kind of organic electroluminescence device, contains in the organic electroluminescence device Multiple functional layers, also have the feature that, at least one functional layer contains above-mentioned electroluminescent organic material.
Prepared organic electroluminescence device generally comprises ITO Conducting Glass, the sky being sequentially overlapped in the present invention Cave transport layer, luminescent layer (the benzopyran-4-one class electroluminescent organic material provided in the present invention is provided), electric transmission Layer, electron injecting layer (LiF) and cathode layer (Al), all functional layers are made of vacuum evaporation process.
It should be appreciated that making the purpose of OLED in the present invention, it is intended merely to be better described, is provided in the present invention The electroluminescent ability that benzopyran-4-one class electroluminescent organic material has, and be not to provided by the present invention The limitation of the range of application of electroluminescent organic material.
The beneficial effect of such scheme is：
The benzopyran-4-one class electroluminescent organic material that the present invention is provided is applied in OLED luminescent devices so that The current efficiency of device, power efficiency and external quantum efficiency are greatly improved.The benzopyran-4-one class that the present invention is provided Electroluminescent organic material has good application effect, with good industrialization prospect.
Brief description of the drawings
Fig. 1 is the structural representation of the organic electroluminescence device of offer in embodiments of the invention, by lower floor to upper strata, It is followed successively by transparent substrate layer (1), transparent electrode layer (2), hole injection layer (3), hole transmission layer (4), luminescent layer (5), electronics Transport layer (6), electron injecting layer (7), negative electrode reflection electrode layer (8), wherein, luminescent layer (5) is related to provided in the present invention Benzopyran-4-one class electroluminescent organic material.
Specific embodiment
Below in conjunction with the accompanying drawing in the embodiment of the present invention, the technical scheme in the embodiment of the present invention is carried out clear, complete Site preparation is described, it is clear that described embodiment is only a part of embodiment of the invention, rather than whole embodiments.It is based on Embodiment in the present invention, those of ordinary skill in the art obtained on the premise of creative work is not made it is all its His embodiment, belongs to the scope of protection of the invention.
It should be noted that in the case where not conflicting, the embodiment in the present invention and the feature in embodiment can phases Mutually combination.
The invention will be further described with specific embodiment below in conjunction with the accompanying drawings, but not as limiting to the invention.
The compound C05 of embodiment 1
The there-necked flask of 250ml, under the atmosphere for being passed through nitrogen, adds 0.01mol 6- bromine-7-methyls-chromene -4- Ketone, 0.02mol compounds A1,0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert phosphorus, 150ml toluene, is heated to reflux 24 hours, sample point plate, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains target product Thing, purity 99.56%, yield 57%.
Elementary analysis structure (molecular formula C34H22N2O2)：Theoretical value：C,83.25；H,4.52；N,5.71；O, 6.52 tests Value：C,83.29；H,4.52；N,5.66；O,6.53.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C34H22N2O2, theoretical value：490.1681, test value： 490.1683。
The compound C08 of embodiment 2
The there-necked flask of 250ml, under the atmosphere for being passed through nitrogen, adds 0.01mol 6- (4- bromophenyls) -7- methyl-benzo Pyrans -4- ketone, 0.02mol compounds A2,0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, the uncles of 1 × 10-4mol tri- Butyl phosphorus, 150ml toluene is heated to reflux 24 hours, sample point plate, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains Target product, purity 99.326%, yield 48%.
Elementary analysis structure (molecular formula C37H27NO2)：Theoretical value：C,85.85；H,5.26；N,2.71；Test value：C, 85.75；H,5.23；N,2.73.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C37H23NO2, theoretical value：517.2042, test value： 517.2046。
The compound C19 of embodiment 3
The there-necked flask of 250ml, under the atmosphere for being passed through nitrogen, adds 0.01mol 6- bromine-7-methyls-chromene -4- Ketone, 0.02mol compound A-13s, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert phosphorus, 150ml toluene, is heated to reflux 24 hours, sample point plate, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains target product Thing, purity 99.6%, yield 45%.
Elementary analysis structure (molecular formula C34H19NO4)：Theoretical value：C,80.78；H,3.79；N,2.77；O, 12.66 tests Value：C,80.74；H,3.80；N,2.78；O,12.68.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C34H19NO4, theoretical value：505.1314, test value： 505.1318。
The compound C21 of embodiment 4
The there-necked flask of 250ml, under the atmosphere for being passed through nitrogen, adds 0.01mol 6- (4- bromophenyls) -7- methyl-benzo Pyrans -4- ketone, 0.02mol compounds A4,0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, the uncles of 1 × 10-4mol tri- Butyl phosphorus, 150ml toluene is heated to reflux 24 hours, sample point plate, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains Target product, purity 99.5%, yield 56.6%.
Elementary analysis structure (molecular formula C67H35NO2)：Theoretical value：C,90.83；H,3.98；N, 1.58 test values：C, 90.85；H,3.85；N,1.55.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C67H35NO2, theoretical value：885.2668, test value： 885.2670。
The compound C23 of embodiment 5
The there-necked flask of 250ml, under the atmosphere for being passed through nitrogen, adds 0.01mol 6- bromine-7-methyls-chromene -4- Ketone, 0.02mol compound A-45s, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert phosphorus, 150ml toluene, is heated to reflux 24 hours, sample point plate, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains target product Thing, purity 99.8%, yield 53.6%.
Elementary analysis structure (molecular formula C37H25NO3)：Theoretical value：C,83.60；H,4.74；N,2.63；O, 9.03 tests Value：C,83.55；H,4.75；N,2.65；O,9.05.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C37H25NO3, theoretical value：531.1834, test value： 531.1834。
The compound C25 of embodiment 6
With embodiment 1, difference is using the A1 in the alternative embodiment 2 of raw material A 6 to the preparation method of compound C25.
Elementary analysis structure (molecular formula C40H24N2O3)：Theoretical value：C,82.74；H,4.17；N,4.82；O, 8.27 tests Value：C,82.76；H,4.12；N,4.87；O,8.25.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C40H24N2O3, theoretical value：580.1787, test value： 580.1790。
The compound C27 of embodiment 7
With embodiment 1, difference is using the A1 in the alternative embodiment 1 of raw material A 7 to the preparation method of compound C27.
Elementary analysis structure (molecular formula C34H19NO4)：Theoretical value：C,80.78；H,3.79；N,2.77；O, 12.66 tests Value：C,80.81；H,3.80；N,2.74；O,12.65.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C34H19NO4, theoretical value：505.1314, test value： 505.1319。
The compound C34 of embodiment 8
With embodiment 1, difference is using the A1 in the alternative embodiment 2 of raw material A 8 to the preparation method of compound C34.
Elementary analysis structure (molecular formula C40H31NO2)：Theoretical value：C,86.15；H,5.60；N,2.51；O, 5.74 tests Value：C,86.16；H,5.62；N,2.49；O,5.73.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C40H31NO2, theoretical value：557.2355, test value： 557.2359。
The compound C43 of embodiment 9
With embodiment 1, difference is using the A1 in the alternative embodiment 1 of raw material A 9 to the preparation method of compound C43.
Elementary analysis structure (molecular formula C40H27N3O2)：Theoretical value：C,82.60；H,4.68；N,7.22；O, 5.50 tests Value：C,82.57；H,4.66；N,7.28；O,5.49.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C40H27N3O2, theoretical value：581.2103, test value： 581.2108。
The compound C46 of embodiment 10
With embodiment 1, difference is using in the alternative embodiment 1 of raw material A 10 to the preparation method of compound C46 A1。
Elementary analysis structure (molecular formula C40H31NO4)：Theoretical value：C,81.47；H,5.30；N,2.38；O,10.85；Test Value：C,81.49；H,5.33；N,2.35；O,10.83.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C40H31NO4, theoretical value：589.2253, test value： 589.2256。
The compound C49 of embodiment 11
With embodiment 1, difference is using in the alternative embodiment 1 of raw material A 11 to the preparation method of compound C49 A1。
Elementary analysis structure (molecular formula C40H31NO4)：Theoretical value：C,81.47；H,5.30；N,2.38；O,10.85；Test Value：C,81.48；H,5.31；N,2.36；O,10.85.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C40H31NO4, theoretical value：589.2253, test value： 589.2258。
The compound C56 of embodiment 12
With embodiment 1, difference is using in the alternative embodiment 1 of raw material A 12 to the preparation method of compound C56 A1。
Elementary analysis structure (molecular formula C33H25NO2)：Theoretical value：C,84.77；H,5.39；N,3.00；O,6.84；Test Value：C,84.79；H,5.38；N,3.01；O,6.82.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C33H25NO2, theoretical value：467.1885, test value： 467.1888。
The compound C62 of embodiment 13
With embodiment 1, difference is using in the alternative embodiment 1 of raw material A 13 to the preparation method of compound C62 A1。
Elementary analysis structure (molecular formula C36H24N2O2)：Theoretical value：C,83.70；H,4.68；N,5.42；O,6.19；Test Value：C,83.79；H,4.65；N,5.39；O,6.16.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C36H24N2O2, theoretical value：516.1838, test value： 516.1839。
The compound C64 of embodiment 14
With embodiment 1, difference is using in the alternative embodiment 1 of raw material A 14 to the preparation method of compound C64 A1。
Elementary analysis structure (molecular formula C46H32N4O2)：Theoretical value：C,82.12；H,4.79；N,8.33；O,4.76；Test Value：C,82.17；H,4.78；N,8.30；O,4.75.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C46H32N4O2, theoretical value：672.2525, test value： 672.2528。
The compound C65 of embodiment 15
With embodiment 1, difference is using in the alternative embodiment 1 of raw material A 15 to the preparation method of compound C65 A1。
Elementary analysis structure (molecular formula C47H32N2O3)：Theoretical value：C,83.91；H,4.79；N,4.16；O,7.13；Test Value：C,83.89；H,4.78；N,4.19；O,7.13.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C47H32N2O3, theoretical value：672.2413, test value： 672.2410。
The compound C80 of embodiment 16
With embodiment 1, difference is using in the alternative embodiment 1 of raw material A 16 to the preparation method of compound C80 A1。
Elementary analysis structure (molecular formula C31H23NO3)：Theoretical value：C,81.38；H,5.07；N,3.06；O,10.49；Test Value：C,81.39；H,5.05；N,3.03；O,10.53.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C31H23NO3, theoretical value：457.1687, test value： 457.1689。
The compound C96 of embodiment 17
The there-necked flask of 250ml, under the atmosphere for being passed through nitrogen, adds 0.01mol 6- (4- bromophenyls) -7- methyl-benzo Pyrans -4- ketone, 0.02mol compounds A16,0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, the uncles of 1 × 10-4mol tri- Butyl phosphorus, 150ml toluene is heated to reflux 24 hours, sample point plate, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains Target product, purity 99.9%, yield 59.6%.
Elementary analysis structure (molecular formula C37H27NO3)：Theoretical value：C,83.28；H,5.10；N,2.62；O, 8.99 tests Value：C,83.25；H,5.15；N,2.64；O,8.95.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C37H27NO3, theoretical value：533.1991, test value： 533.2001。
The compound C98 of embodiment 18
With embodiment 17, difference is using in the alternative embodiment 17 of raw material A 17 to the preparation method of compound C98 A16。
Elementary analysis structure (molecular formula C37H28N2O2)：Theoretical value：C,83.43；H,5.30；N,5.26；O,6.01；Test Value：C,83.45；H,5.25；N,5.29；O,6.01.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C37H28N2O2, theoretical value：532.2151, test value： 532.2156。
The compound C99 of embodiment 19
With embodiment 17, difference is using in the alternative embodiment 17 of raw material A 18 to the preparation method of compound C99 A16。
Elementary analysis structure (molecular formula C40H27N3O2)：Theoretical value：C,82.60；H,4.68；N,7.22；O,5.50；Test Value：C,82.65；H,4.67；N,7.20；O,5.48.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C40H27N3O2, theoretical value：581.2103, test value： 581.2106。
The compound C100 of embodiment 20
With embodiment 17, difference is using in the alternative embodiment 17 of raw material A 19 to the preparation method of compound C100 A16.
Elementary analysis structure (molecular formula C37H27NO2)：Theoretical value：C,85.85；H,5.26；N,2.71；O,6.18；Test Value：C,85.86；H,5.27；N,2.72；O,6.15.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C37H27NO2, theoretical value：517.2042, test value： 517.2047。
The compound C108 of embodiment 21
The there-necked flask of 250ml, under the atmosphere for being passed through nitrogen, adds 0.01mol 6- (3'- bromo biphenyl -3- bases) -- 7- first Base-benzopyran-4-one, 0.02mol compounds A16,0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10- 4mol tri-tert phosphorus, 150ml toluene is heated to reflux 24 hours, sample point plate, natural cooling, filtering, filtrate revolving, crosses silicon Glue post, obtains target product, purity 99.9%, yield 59.6%.
Elementary analysis structure (molecular formula C43H31NO3)：Theoretical value：C,84.71；H,5.12；N,2.30；Test value：C, 84.68；H,5.15；N,2.32.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C43H31NO3, theoretical value：609.2304, test value： 609.2308。
The compound C110 of embodiment 22
With embodiment 17, difference is using in the alternative embodiment 17 of raw material A 20 to the preparation method of compound C110 A16.
Elementary analysis structure (molecular formula C37H27NO3)：Theoretical value：C,83.28；H,5.10；N,2.62；Test value：C, 83.26；H,5.17；N,2.65.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C37H27NO3, theoretical value：533.1991, test value： 533.1997。
The compound C112 of embodiment 22
With embodiment 21, difference is using raw material 6- (4'- bromo biphenyls -3- to the preparation method of compound C112 Base) 6- (4- bromophenyls) -7- methyl-benzopyran-4-one in -7- methyl-benzopyran-4-one alternative embodiment 21.
Elementary analysis structure (molecular formula C43H31NO3)：Theoretical value：C,84.71；H,5.12；N,2.30；Test value：C, 84.74；H,5.10；N,2.31.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C43H31NO3, theoretical value：609.2304, test value： 609.2307。
The compound C113 of embodiment 23
With embodiment 17, difference is using in the alternative embodiment 17 of raw material A 21 to the preparation method of compound C113 A16.
Elementary analysis structure (molecular formula C37H27NO3)：Theoretical value：C,83.28；H,5.10；N,2.62；Test value：C, 83.30；H,5.08；N,2.68.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C37H27NO3, theoretical value：533.1991, test value： 533.2001。
The compound C115 of embodiment 24
With embodiment 22, difference is using in the alternative embodiment 22 of raw material A 21 to the preparation method of compound C115 A20.
Elementary analysis structure (molecular formula C43H31NO3)：Theoretical value：C,84.71；H,5.12；N,2.30；Test value：C, 84.79；H,5.13；N,2.26.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C43H31NO3, theoretical value：609.2304, test value： 609.2310。
The above-mentioned compound 83 for preparing, compound 87 and current material CBP, BD carry out hot property, luminescent spectrum, The test of fluorescence quantum efficiency and cyclic voltammetric stability, it is as a result as shown in the table：
Compound Tg(℃) Td(℃) λPL(nm) Φf Cyclic voltammetric stability
Compound C96 137 372 473 75.9 It is excellent
Material C BP 113 353 369 26.1 Difference
Compound C115 141 385 463 76.3 It is excellent
Material BD1 - 334 486 58.3 Difference
From upper table data, the benzopyran-4-one class electroluminescent organic material that the present invention is provided has suitable HOMO energy levels and heat endurance higher, are suitable as the material of main part of luminescent layer.
Organic electroluminescence device embodiment
Device 1-8 is prepared with the above-mentioned electroluminescent organic material in part in embodiments of the invention 25-32, should be managed Solution, device implementation process and result, are intended merely to preferably explain the present invention, not limitation of the present invention, above-mentioned Organic Electricity The preparation method of electroluminescence device is as follows：
A) neutralizing treatment, pure water, drying carried out successively to ito anode layer (thickness is 150nm), then carry out ultraviolet- Ozone washing is removing the organic residue on the surface of transparent ITO-anode layer 2.
B) it is deposited with hole injection layer (MoO on ito anode layer3), thickness is 10nm；
C) hole transmission layer (TAPC), thickness 140nm are deposited with hole injection layer；
D) luminescent layer, thickness 30nm are deposited with hole transmission layer；
E) electron transfer layer (TPBI) is deposited with luminescent layer, thickness is 40nm；
F) electron injecting layer device (LiF), thickness 1nm are deposited with the electron transport layer；
G) evaporation cathode reflection electrode layer (Al) on electron injecting layer, thickness 80nm.
As above after completing device 1-8 and comparative device, anode and negative electrode are coupled together with known drive circuit, is measured The life-span of the current efficiency of device, luminescent spectrum and device, the principal structural layer and test of device 1-8 and comparative device 1-3 Result is as shown in the table：
The molecular structural formula of each compound is as follows：
In above-mentioned test, the current efficiency of comparative example 1 is 6.5cd/A (@10mA/cm2)；Startup voltage is 4.3V (@1cd/ M2), LT95 life time decays are 3.8Hr under 5000nit brightness.The current efficiency of comparative example 2 is 24.6cd/A (@10mA/cm2)； LT95 life time decays are 4.3Hr under 5000nit brightness.The current efficiency of comparative example 3 is 25.1cd/A (@10mA/cm2)；Start Voltage is 3.5V (@1cd/m2), and LT95 life time decays are 7.8Hr under 5000nit brightness.
From upper table analysis, benzopyran-4-one class electroluminescent organic material provided by the present invention is used as luminous The efficiency and startup voltage of the OLED luminescent devices obtained by layer main body material obtain larger change than known OLED material, special It is not that efficiency roll-off under device high current density is improved.Benzopyran-4-one class organic electroluminescence provided by the present invention Luminescent material has good application effect in OLED luminescent devices, with good industrialization prospect.
Preferred embodiments of the present invention are the foregoing is only, embodiments of the present invention and protection model is not thereby limited Enclose, to those skilled in the art, should can appreciate that done by all utilization description of the invention and diagramatic content Scheme obtained by equivalent and obvious change, should be included in protection scope of the present invention.

Claims (10)

1. a kind of benzopyran-4-one class electroluminescent organic material, it is characterised in that the electroluminescent organic material is with benzene And pyrans -4- ketone is parent nucleus, shown in its structural formula such as formula (I) or formula (II)：
Wherein, R1Selected from C1-6Alkyl；
Wherein, Ar is selected from the one kind in phenyl, dibiphenylyl, terphenyl, naphthyl, anthryl or phenanthryl, n=1 or 2, R2Selected from containing Substituted base or without substitution baseThe base containing substitution or without substitution baseWherein, X1It is selected from Oxygen atom, sulphur atom, two (C1-10Straight chained alkyl) substitution season alkyl, two (C1-10Branched alkyl) substitution season alkyl, aryl takes Generation season alkyl, alkyl-substituted tertiary amine groups or aryl substitution tertiary amine groups in one kind.
2. electroluminescent organic material according to claim 1, it is characterised in that described containing substituted baseWith the base containing substitutionIt is quilt at least one phenyl ring Ortho position unitary substitution, wherein, X2、X3、X4Separately it is selected from oxygen atom, sulphur atom, two (C1-10Directly Alkyl group) substitution season alkyl, two (C1-10Branched alkyl) substitution season alkyl, the season alkyl, alkyl-substituted of aryl substitution One kind in tertiary amine groups or the tertiary amine groups of aryl substitution.
3. electroluminescent organic material according to claim 2, it is characterised in that described containing substituted baseIn quilt at least one phenyl ringSubstitution, andBy C4-C5Or C4'-C5'It is bonded when connecing, X1And X2Overlap, only take X1Or X2。
4. a kind of preparation method of electroluminescent organic material according to claim any one of 1-3, it is characterised in that bag Include：
To the benzopyran-4-one ring bromo compound, the amine compound that weigh is loaded in reaction bulb, reaction dissolvent is added, then Catalyst, part and alkali are added, it is under an inert atmosphere, the mixed solution of above-mentioned reactant is small in 95-100 DEG C of reaction 10-24 When, through cooling, filtering, column chromatography after stopping reacting, obtain the electroluminescent organic material.
5. electroluminescent organic material according to claim 4, it is characterised in that the catalyst is Pd2(dba)3, and And, the catalyst is 0.006-0.02 with the mol ratio of the benzopyran-4-one ring bromo compound:1.
6. electroluminescent organic material according to claim 4, it is characterised in that the benzopyran-4-one ring bromo Compound is 1 with the mol ratio of the amine compound:2.0-4.0.
7. electroluminescent organic material according to claim 4, it is characterised in that the alkali is sodium tert-butoxide, also, institute It is 1.0-3.0 that alkali is stated with the mol ratio of the benzopyran-4-one ring bromo compound:1.
8. electroluminescent organic material according to claim 4, it is characterised in that the part is tri-tert phosphorus, and And, the part is 0.006-0.02 with the mol ratio of the benzopyran-4-one ring bromo compound:1.
9. it is a kind of according to any described benzopyran-4-one class electroluminescent organic materials of claim 1-3 prepare it is organic Application in electroluminescent device.
10. a kind of organic electroluminescence device, including multiple functional layers, it is characterised in that at least one described functional layer contains Have the right any described benzopyran-4-one class electroluminescent organic materials of requirement 1-3.
CN201611153197.8A 2016-12-14 2016-12-14 Ketone electroluminescent organic material of a kind of chromene 4 and its preparation method and application Withdrawn CN106749200A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201611153197.8A CN106749200A (en) 2016-12-14 2016-12-14 Ketone electroluminescent organic material of a kind of chromene 4 and its preparation method and application

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201611153197.8A CN106749200A (en) 2016-12-14 2016-12-14 Ketone electroluminescent organic material of a kind of chromene 4 and its preparation method and application

Publications (1)

Publication Number Publication Date
CN106749200A true CN106749200A (en) 2017-05-31

Family

ID=58887828

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201611153197.8A Withdrawn CN106749200A (en) 2016-12-14 2016-12-14 Ketone electroluminescent organic material of a kind of chromene 4 and its preparation method and application

Country Status (1)

Country Link
CN (1) CN106749200A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107501292A (en) * 2017-08-28 2017-12-22 长春海谱润斯科技有限公司 A kind of electroluminescent organic material and its organic luminescent device
KR20190129509A (en) * 2018-05-11 2019-11-20 주식회사 엘지화학 Multicyclic compound and organic light emitting device comprising the same
CN110669033A (en) * 2019-09-19 2020-01-10 武汉华星光电半导体显示技术有限公司 Electroluminescent material, preparation method of electroluminescent material and luminescent device
CN112079806A (en) * 2020-09-19 2020-12-15 吉林奥来德光电材料股份有限公司 Organic electroluminescent compound, preparation method thereof and organic electroluminescent device
CN112661778A (en) * 2020-12-30 2021-04-16 中节能万润股份有限公司 Boron-containing aryl imide organic electroluminescent material and application thereof

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1880314A (en) * 2005-12-02 2006-12-20 西安瑞联近代电子材料有限责任公司 Synthesis method of red doped material BDCJT for OLED device
CN103887444A (en) * 2013-12-31 2014-06-25 昆山工研院新型平板显示技术中心有限公司 OLED blue-light device capable of enhancing the service life
WO2015121239A1 (en) * 2014-02-14 2015-08-20 Hartmut Yersin Organic molecule having small triplet-singlet energy spacings for effective delayed fluorescence for application in optoelectronic devices
CN105340101A (en) * 2013-07-03 2016-02-17 国立大学法人九州大学 Light-emitting material, long-persistent phosphor, organic light-emitting element and compound
CN105916963A (en) * 2014-01-17 2016-08-31 默克专利有限公司 Materials for organic electroluminescent devices
CN105968104A (en) * 2016-07-20 2016-09-28 深圳市华星光电技术有限公司 Luminescent material and preparation method thereof and organic light emitting diode using same

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1880314A (en) * 2005-12-02 2006-12-20 西安瑞联近代电子材料有限责任公司 Synthesis method of red doped material BDCJT for OLED device
CN105340101A (en) * 2013-07-03 2016-02-17 国立大学法人九州大学 Light-emitting material, long-persistent phosphor, organic light-emitting element and compound
CN103887444A (en) * 2013-12-31 2014-06-25 昆山工研院新型平板显示技术中心有限公司 OLED blue-light device capable of enhancing the service life
CN105916963A (en) * 2014-01-17 2016-08-31 默克专利有限公司 Materials for organic electroluminescent devices
WO2015121239A1 (en) * 2014-02-14 2015-08-20 Hartmut Yersin Organic molecule having small triplet-singlet energy spacings for effective delayed fluorescence for application in optoelectronic devices
CN105968104A (en) * 2016-07-20 2016-09-28 深圳市华星光电技术有限公司 Luminescent material and preparation method thereof and organic light emitting diode using same

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107501292A (en) * 2017-08-28 2017-12-22 长春海谱润斯科技有限公司 A kind of electroluminescent organic material and its organic luminescent device
KR20190129509A (en) * 2018-05-11 2019-11-20 주식회사 엘지화학 Multicyclic compound and organic light emitting device comprising the same
KR102225901B1 (en) 2018-05-11 2021-03-09 주식회사 엘지화학 Multicyclic compound and organic light emitting device comprising the same
CN110669033A (en) * 2019-09-19 2020-01-10 武汉华星光电半导体显示技术有限公司 Electroluminescent material, preparation method of electroluminescent material and luminescent device
CN112079806A (en) * 2020-09-19 2020-12-15 吉林奥来德光电材料股份有限公司 Organic electroluminescent compound, preparation method thereof and organic electroluminescent device
CN112079806B (en) * 2020-09-19 2023-08-18 吉林奥来德光电材料股份有限公司 Organic electroluminescent compound, preparation method thereof and organic electroluminescent device
CN112661778A (en) * 2020-12-30 2021-04-16 中节能万润股份有限公司 Boron-containing aryl imide organic electroluminescent material and application thereof

Similar Documents

Publication Publication Date Title
CN106467554A (en) A kind of boracic organic electroluminescent compounds and its application
CN106279203B (en) Compound containing ketone and nitrogen heterocycle and application thereof in organic electroluminescent device
CN107245079B (en) A kind of azepine xanthone compound and its application in OLED device
CN108586507A (en) A kind of long-life boracic organic electroluminescent compounds and its application
CN106220638A (en) A kind of compound based on xanthone and application thereof
CN106749200A (en) Ketone electroluminescent organic material of a kind of chromene 4 and its preparation method and application
CN106898699B (en) A kind of organic electroluminescence device
CN107068888B (en) A kind of organic electroluminescence device containing ketone and heterocyclic nitrogen compound and its application
CN107068910A (en) A kind of organic electroluminescence device of compound containing xanthone and its application
CN107056748A (en) It is a kind of using triazine and ketone as the compound of core and its application on organic electroluminescence device
CN106467523A (en) A kind of organic aromatic compound and its application
CN110128403B (en) Compound, display panel and display device
CN106977446A (en) It is a kind of using three benzo cycloheptene ketone as the compound of core and its application in OLED
CN107057680A (en) A kind of compound as core using anthrone and its application on organic electroluminescence device
CN107652272A (en) It is a kind of using ketone structure as the organic compound of parent nucleus and its application in OLED
CN106220645A (en) Compound based on monosubstituted-9-fluorenone and application thereof
CN107043382A (en) A kind of compound as core using triazine and its application on organic electroluminescence device
CN106749050B (en) It is a kind of using cyclic diketones as the hot activation delayed fluorescence OLED material of core and its application
CN106243057A (en) A kind of compound based on azepine equal benzene structure and the application on OLED thereof
CN109574909A (en) It is a kind of using ketone structure as the organic compound of core and its application in OLED device
CN107056770A (en) A kind of compound as core using nitrogenous five-ring heterocycles and its application on organic electroluminescence device
CN107056758A (en) A kind of compound as core using acridine spiral shell anthrone and its application on organic electroluminescence device
CN106800567A (en) A kind of acridine spiral shell thioxanthene sulfone derivatives and its preparation method and application
CN106467511A (en) A kind of compound with acridone as core and its application on organic electroluminescence device
CN115028626B (en) Thermally-induced delayed fluorescent material and preparation method and application thereof

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
WW01 Invention patent application withdrawn after publication
WW01 Invention patent application withdrawn after publication

Application publication date: 20170531