CN110229094A - Electroluminescent material, the preparation method of electroluminescent material and luminescent device - Google Patents
Electroluminescent material, the preparation method of electroluminescent material and luminescent device Download PDFInfo
- Publication number
- CN110229094A CN110229094A CN201910588608.3A CN201910588608A CN110229094A CN 110229094 A CN110229094 A CN 110229094A CN 201910588608 A CN201910588608 A CN 201910588608A CN 110229094 A CN110229094 A CN 110229094A
- Authority
- CN
- China
- Prior art keywords
- reactant
- electroluminescent material
- group
- compound
- layer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000463 material Substances 0.000 title claims abstract description 113
- 238000002360 preparation method Methods 0.000 title claims abstract description 26
- 239000000376 reactant Substances 0.000 claims description 109
- 150000001875 compounds Chemical class 0.000 claims description 97
- 239000013067 intermediate product Substances 0.000 claims description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 37
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 239000002904 solvent Substances 0.000 claims description 27
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 19
- 235000019441 ethanol Nutrition 0.000 claims description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 17
- 239000000758 substrate Substances 0.000 claims description 15
- 239000000654 additive Substances 0.000 claims description 13
- 230000000996 additive effect Effects 0.000 claims description 13
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 12
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 11
- 239000012312 sodium hydride Substances 0.000 claims description 11
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 11
- 230000000903 blocking effect Effects 0.000 claims description 10
- 230000005525 hole transport Effects 0.000 claims description 10
- -1 R2 group Chemical class 0.000 claims description 9
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 7
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 4
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 abstract description 6
- 125000000524 functional group Chemical group 0.000 abstract description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 5
- 238000000034 method Methods 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 230000003993 interaction Effects 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 239000002274 desiccant Substances 0.000 description 18
- 239000003599 detergent Substances 0.000 description 18
- 239000003480 eluent Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000012153 distilled water Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 239000011574 phosphorus Substances 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000011505 plaster Substances 0.000 description 6
- 239000001103 potassium chloride Substances 0.000 description 6
- 235000011164 potassium chloride Nutrition 0.000 description 6
- 239000012266 salt solution Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 238000000103 photoluminescence spectrum Methods 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910052792 caesium Inorganic materials 0.000 description 3
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- IDDAQARKHUGOPH-UHFFFAOYSA-N benzene oxalonitrile Chemical group C1=CC=CC=C1.N#CC#N IDDAQARKHUGOPH-UHFFFAOYSA-N 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 description 1
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- 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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The application provides a kind of electroluminescent material, the preparation method and luminescent device of electroluminescent material, using benzene cyano, group is used as electroluminescent material main body, using carbazole group as branch, to reduce the interaction in each molecule between main body, it not only restrained effectively molecule reunion, and it can have the function that equilbrium carrier transmits, it is high to realize luminous efficiency, the electroluminescent material of blue light can be issued, simultaneously, the carbazole group of branch further includes the functional group with alkyl chain, the functional group increases the dissolubility of molecule, to achieve the purpose that prepare luminescent device using wet process.
Description
Technical field
This application involves display fields, and in particular to a kind of electroluminescent material, electroluminescent material preparation method and
Luminescent device.
Background technique
In the prior art, Organic Light Emitting Diode (Organic Light Emitting Diode) has self-luminous special
Property, dominating its luminous material is mainly electroluminescent material, and still, the luminous efficiency of current electroluminescent material is low, past
Toward leading to the failure of Organic Light Emitting Diode, therefore, it is necessary to provide a kind of electroluminescent material that luminous efficiency is high, electroluminescent hair
The preparation method and luminescent device of luminescent material.
Summary of the invention
The application provides the preparation method of a kind of electroluminescent material high with electroluminescent efficiency, electroluminescent material
And luminescent device.
The application provides a kind of electroluminescent material, and the structural formula of the electroluminescent material isWherein, the R1Knot
Structure formula isThe R2Structural formula be
The application provides a kind of preparation method of electroluminescent material, comprising:
The first reactant and the second reactant are provided, first reactant and second reactant carry out reaction generation
The electroluminescent material, wherein the structural formula of first reactant isThe X1For F, Cl
One of with Br, the X2For for one of F, Cl and Br, the X2Atomic number be more than or equal to the X1Atomic number
Number, second reactant be include R1The compound of group and/or including R2The compound of group, the electroluminescent material
Structural formula beWherein,
The R1Structural formula beThe R2Structural formula be
In the preparation method of electroluminescent material provided herein, as the X2Atomic number be equal to the X1
Atomic number when, second reactant be include R1The compound of group or including R2The compound of group, the electroluminescent hair
The structural formula of luminescent material is
In the preparation method of electroluminescent material provided herein, the mole of first reactant and described
The corresponding relationship of the mole of second reactant is described the of corresponding -3 mmoles of 1 mmoles of first reactant of 2-10 mmoles
Two reactants.
In the preparation method of electroluminescent material provided herein, first reactant and second reaction
Object carries out reaction in the first solvent and generates the electroluminescent material, and first solvent includes tetrahydrofuran, toluene, second
The combination of one or more of alcohol, ethylene, perchloroethylene, trichloro ethylene, acetone, ethylene glycol ether and triethanolamine.
There is the first addition in the preparation method of electroluminescent material provided herein, in first solvent
Agent, first additive include potassium carbonate, four triphenyl phosphorus palladiums, cesium carbonate, potassium hydroxide, sodium hydride, sodium hydroxide, tertiary fourth
Sodium alkoxide (NaOt- Bu) and one or more of sodium bicarbonate combination.
In the preparation method of electroluminescent material provided herein, as the X2Atomic number be greater than the X1
Atomic number when, second reactant be include R1The compound of group and including R2The compound of group, the electroluminescent hair
The structural formula of luminescent material is
In the preparation method of electroluminescent material provided herein, the first reactant of the offer and the second reaction
Object, first reactant and second reactant carry out reacting the step of generating electroluminescent material
First reactant is provided;
There is provided includes R1The compound of group, first reactant and it is described include R1The compound of group, which reacts, to be generated
The structural formula of first intermediate product, first intermediate product isAnd
There is provided includes R2The compound of group, first intermediate product and it is described include R2The compound of group reacts life
At the electroluminescent material, the structural formula of the electroluminescent material is
In the preparation method of electroluminescent material provided herein, the first reactant of the offer and the second reaction
Object, first reactant and second reactant carry out reacting the step of generating electroluminescent material
First reactant is provided;
There is provided includes R2The compound of group, first reactant and it is described include R2The compound of group, which reacts, to be generated
The structural formula of second intermediate product, second intermediate product isAnd
There is provided includes R2The compound of group, second intermediate product and it is described include R2The compound of group reacts life
At the electroluminescent material, the structural formula of the electroluminescent material is
The application provides a kind of luminescent device, comprising:
Substrate layer, the substrate layer include substrate and anode layer, and the anode layer is set on the substrate;
Hole transport and implanted layer, the hole transport and implanted layer are set on the anode layer;
Luminescent layer, the luminescent layer is set to the hole transport and implanted layer is set;
Electron-transport and hole blocking layer, the electron-transport and hole blocking layer are set on the luminescent layer;
Electron injecting layer, the electron injecting layer are set on the electron-transport and hole blocking layer;
Cathode layer, the cathode layer are set on the electron injecting layer;
The luminescent layer includes the electroluminescent material, wherein the structural formula of the electroluminescent material isWherein, the R1Knot
Structure formula isThe R2Structural formula be
The application provides the preparation method and luminescent device of a kind of electroluminescent material, electroluminescent material, using benzene cyanogen
Group is as electroluminescent material main body, using carbazole group as branch, to reduce the phase in each molecule between main body
Interaction not only restrained effectively molecule reunion, but also can have the function that equilbrium carrier transmits, and realize luminous efficiency
Electroluminescent material high, that blue light can be issued, meanwhile, the carbazole group of branch further includes the functional group with alkyl chain, institute
It states functional group and increases the dissolubility of molecule, to achieve the purpose that prepare luminescent device using wet process.
Detailed description of the invention
It, below will be to needed in embodiment description in order to illustrate more clearly of the technical solution in the application
Attached drawing is briefly described, it should be apparent that, the accompanying drawings in the following description is only some embodiments of the application, for this
For the technical staff of field, without creative efforts, it is also possible to obtain other drawings based on these drawings.
Fig. 1 is the photoluminescence spectra of the compound one of electroluminescent material provided herein.
Fig. 2 is the photoluminescence spectra of the compound two of electroluminescent material provided herein.
Fig. 3 is the photoluminescence spectra of the compound three of electroluminescent material provided herein.
Fig. 4 is the photoluminescence spectra of the compound four of electroluminescent material provided herein.
Fig. 5 is the structural schematic diagram of luminescent device provided herein.
Specific embodiment
Below in conjunction with the attached drawing in the application embodiment, the technical solution in the application is carried out clearly and completely
Description.Obviously, described embodiment is only a part of embodiment of the application, rather than whole embodiments.Base
Embodiment in the application, those skilled in the art are obtained every other without making creative work
Embodiment shall fall in the protection scope of this application.
The application provides a kind of electroluminescent material, and the structural formula of the electroluminescent material isWherein, the R1Knot
Structure formula isThe R2Structural formula beIt is described electroluminescent
Luminescent material is the electroluminescent material that can issue blue light.
The structural formula of the electroluminescent material can be
One of.
The application also provides a kind of preparation method of electroluminescent material.The preparation method packet of the electroluminescent material
It includes: providing the first reactant and the second reactant, it is electroluminescent that first reactant and second reactant carry out reaction generation
Luminescent material.
The structural formula of first reactant isThe X1For one of F, Cl and Br.The X2
For for one of F, Cl and Br.The X2Atomic number be more than or equal to the X1Atomic number.Second reactant is
Including R1The compound of group and/or including R2The compound of group.The structural formula of the electroluminescent material is The R1Structural formula beThe R2Structural formula be
In some embodiments, as the X2Atomic number be equal to the X1Atomic number when, second reactant
Being includes R1The compound of group or including R2The structural formula of the compound of group, the electroluminescent material is
First reactant and it is described include R1The reaction equation of the compound of group can be with are as follows:
The R1It includes R that-H, which is described,1The compound of group.
First reactant and it is described include R2The reaction equation of the compound of group can be with are as follows:
The R2It includes R that-H, which is described,2The compound of group.
The corresponding relationship of the mole of first reactant and the mole of second reactant is 2-10 mmoles
Second reactant of corresponding -3 mmoles of 1 mmoles of first reactant.In some embodiments, first reactant
The corresponding relationship of mole and the mole of second reactant can be corresponding 2 mmoles of first reactant of 7 mmoles
Second reactant, 4 mmoles corresponding 1 mmoles of first reactant second reactant or 8 moles described
Corresponding 3 moles of second reactant of first reactant.
First reactant and second reactant carry out reaction in the first solvent and generate the electroluminescence material
Material.First solvent includes tetrahydrofuran, toluene, ethyl alcohol, ethylene, perchloroethylene, trichloro ethylene, acetone, ethylene glycol
The combination of one or more of ether and triethanolamine.
There is the first additive in first solvent.First additive includes potassium carbonate, four triphenyl phosphorus palladiums, carbon
Sour caesium, potassium hydroxide, sodium hydride, sodium hydroxide, sodium tert-butoxide (NaOt- Bu) and one or more of sodium bicarbonate group
It closes.
In one embodiment, by the second reactant of 6 mmolesIt is dissolved in 15 millis
It rises in -25 milliliters of the first solvents tetrahydrofurane, the first additive sodium hydride of -2 mmoles of 0.5 mmoles is slow added into, in room
Warm condition and under nitrogen protection reacts 20-50 minutes, the first reactant of 2 mmoles is then addedAfter
Continuous reaction 12 hours, obtains including the electroluminescent material
Mixture.By the electroluminescent materialMixture it is cold
But it to pouring into distilled water after room temperature, is extracted, is then washed using the first detergent, then adopt with the first extractant
It is dried with the first desiccant, is then chromatographed again, obtain the first crude product, then eluted using the first eluant, eluent
After obtain the electroluminescent materialThe electroluminescent
MaterialFor white solid, yield 64%.
First extractant can be the combination of one or more of methylene chloride, chloroform and acetone.Institute
Stating the first detergent can be the combination of one or more of saturated salt solution, saturation potassium chloride and distilled water.Described first
Desiccant can be anhydrous sodium sulfate, anhydrous magnesium sulfate, anhydrous calcium chloride, dead plaster, Anhydrous potassium carbonate and five oxidations two
The combination of one or more of phosphorus.First eluant, eluent is one or more of methylene chloride, ethyl alcohol and chloroform
Combination.
In the present embodiment, first extractant can be methylene chloride.First detergent can be saturation
Saline solution.First desiccant can be anhydrous sodium sulfate.First eluant, eluent is the mixture of methylene chloride and ethyl alcohol.
In one embodiment, by the second reactant of 6 mmolesIt is dissolved in 15 millis
It rises in -25 milliliters of the first solvents tetrahydrofurane, the first additive sodium hydride of -2 mmoles of 0.5 mmoles is slow added into, in room
Warm condition and under nitrogen protection reacts 20-50 minutes, the first reactant of 2 mmoles is then addedAfter
Continuous reaction 12 hours, obtains including the electroluminescent materialMixture.By the electroluminescent materialMixture be cooled to room temperature after pour into steaming
It in distilled water, is extracted with the second extractant, is then washed using the second detergent, then carried out using the second desiccant
It is dry, it is then chromatographed again, obtains the second crude product, then carry out affording the electroluminescent using the second eluant, eluent
MaterialThe electroluminescent materialFor white solid, yield 54%.
Second extractant can be the combination of one or more of methylene chloride, chloroform and acetone.Institute
Stating the second detergent can be the combination of one or more of saturated salt solution, saturation potassium chloride and distilled water.Described second
Desiccant can be anhydrous sodium sulfate, anhydrous magnesium sulfate, anhydrous calcium chloride, dead plaster, Anhydrous potassium carbonate and five oxidations two
The combination of one or more of phosphorus.Second eluant, eluent is one or more of methylene chloride, ethyl alcohol and chloroform
Combination.
In the present embodiment, second extractant can be methylene chloride.Second detergent can be saturation
Saline solution.Second desiccant can be anhydrous sodium sulfate.Second eluant, eluent is the mixture of methylene chloride and ethyl alcohol.
In some embodiments, as the X2Atomic number be greater than the X1Atomic number when, second reactant
Being includes R1The compound of group and including R2The structural formula of the compound of group, the electroluminescent material is
In some embodiments, the first reactant of the offer and the second reactant, first reactant and described
Two reactants carry out reacting the step of generating electroluminescent material
A1, the first reactant is provided;
A2, it provides including R1The compound of group, first reactant and it is described include R1The compound of group reacts life
At the first intermediate product, the structural formula of first intermediate product isAnd
A3, it provides including R2The compound of group, first intermediate product and it is described include R2The compound of group reacts
The electroluminescent material is generated, the structural formula of the electroluminescent material is
First reactant and it is described include R1The reaction equation that the compound reaction of group generates the first intermediate product can
With are as follows:
The R1It includes R that-H, which is described,1The compound of group.
The mole of first reactant and it is described include R1The corresponding relationship of the mole of the compound of group is 2 millis
The described of corresponding -3 mmoles of 1 mmoles of first reactant for -5 mmoles of rubbing includes R1The compound of group.In some embodiments
In, the mole of first reactant and it is described include R1The corresponding relationship of the mole of the compound of group can be 4 millis
The described of corresponding 1.5 mmoles of first reactant to rub includes R1First reactant pair of the compound of group, 3 mmoles
Answering the described of 1.5 mmoles includes R1The compound of group or the described of 3 moles of 5 moles of first reactant correspondence include R1
The compound of group.
First reactant and it is described include R1The compound of group reacts in the second solvent to be produced among generation first
Object.Second solvent includes tetrahydrofuran, toluene, ethyl alcohol, ethylene, perchloroethylene, trichloro ethylene, acetone, ethylene glycol
The combination of one or more of ether and triethanolamine.
There is Second addition in second solvent.The Second addition includes potassium carbonate, four triphenyl phosphorus palladiums, carbon
Sour caesium, potassium hydroxide, sodium hydride, sodium hydroxide, sodium tert-butoxide (NaOt- Bu) and one or more of sodium bicarbonate group
It closes.
First intermediate product and it is described include R2The compound reaction of group generates the anti-of the electroluminescent material
Ying Shike with are as follows:
The R2It includes R that-H, which is described,2The compound of group.
The mole of first intermediate product and it is described include R2The corresponding relationship of the mole of the compound of group is 1
The described of corresponding 1 mmoles of first intermediate product of -3 mmoles of mmoles includes R2The compound of group.In some embodiments,
The mole of first intermediate product and it is described include R2The corresponding relationship of the mole of the compound of group can be 5 mmoles
The described of corresponding 5 mmoles of first intermediate product include R2The compound of group, 2 moles of first intermediate product pair
Answer 1 mole it is described include R2The compound of group or corresponding the described of 1.5 mmoles of first intermediate product of 1 mmoles include
R2The compound of group.
First intermediate product and it is described include R2It is described electroluminescent that the compound of group reacts generation in third solvent
Luminescent material.The third solvent includes tetrahydrofuran, toluene, ethyl alcohol, ethylene, perchloroethylene, trichloro ethylene, acetone, N, N-
The combination of one or more of dimethylformamide, ethylene glycol ether and triethanolamine.
There is third additive in the third solvent.The third additive includes potassium carbonate, four triphenyl phosphorus palladiums, iodine
Change cuprous, cesium carbonate, potassium hydroxide, 1,10- ferrosin, sodium hydride, sodium hydroxide, sodium tert-butoxide (NaOt- Bu), potassium carbonate and
The combination of one or more of sodium bicarbonate.
In one embodiment, by the second reactantIt is dissolved in 20 milliliters -35 milliliters
The second solvents tetrahydrofurane in, be slow added into the second catalyst sodium hydride, in room temperature condition and under nitrogen protection, reaction
20-50 minutes, the first reactant of 2 mmoles is then addedThe reaction was continued 12 hours, obtains including described
First intermediate productMixture.It will include first intermediate productMixture be cooled to room temperature and pour into distilled water, extracted with third extractant, so
It is washed using third detergent, then is dried using third desiccant afterwards, then chromatographed again, obtain third crude product,
Then it carries out affording first intermediate product using third eluant, eluentIn described first
Between productFor white solid, yield 78%.
The third extractant can be the combination of one or more of methylene chloride, chloroform and acetone.Institute
Stating third detergent can be the combination of one or more of saturated salt solution, saturation potassium chloride and distilled water.The third
Desiccant can be anhydrous sodium sulfate, anhydrous magnesium sulfate, anhydrous calcium chloride, dead plaster, Anhydrous potassium carbonate and five oxidations two
The combination of one or more of phosphorus.The third eluant, eluent is one or more of methylene chloride, ethyl alcohol and chloroform
Combination.
In the present embodiment, the third extractant can be methylene chloride.The third detergent can be saturation
Saline solution.The third desiccant can be anhydrous sodium sulfate.The third eluant, eluent is the mixture of methylene chloride and ethyl alcohol.
The first intermediate product of 1 mmoles is added in the reaction vesselWith 1 mmoles
It is described include R2The compound of groupThird catalyst is added, the third is urged
Agent includes the potassium carbonate of the cuprous iodide of 5 mmoles, 1, the 10- ferrosin of 5 mmoles and 10 mmoles, and the of 15 milliliters is then added
Three solvent n,N-Dimethylformamide react 24 hours under 160 degrees Celsius under nitrogen protection, obtain including described electroluminescent
Luminescent materialMixture, by the electroluminescent materialMixture be cooled to room temperature after, using the 4th extraction it is molten
Agent is extracted, and is then washed using the 4th detergent, then is dried using the 4th desiccant, then carries out layer again
Analysis, obtains the 4th crude product, then is eluted to obtain the electroluminescent material using the first eluentThe electroluminescent materialFor white solid, yield 56%.
4th extractant can be the combination of one or more of methylene chloride, chloroform and acetone.Institute
Stating the 4th detergent can be the combination of one or more of saturated salt solution, saturation potassium chloride and distilled water.Described 4th
Desiccant can be anhydrous sodium sulfate, anhydrous magnesium sulfate, anhydrous calcium chloride, dead plaster, Anhydrous potassium carbonate and five oxidations two
The combination of one or more of phosphorus.First eluent is one of methylene chloride, ethyl alcohol, petroleum ether and chloroform
Or several combination.
In the present embodiment, the 4th extractant can be methylene chloride.4th detergent can be distillation
Water.4th desiccant can be anhydrous sodium sulfate.First eluent is the mixing of petroleum ether, methylene chloride and ethyl alcohol
Object.
In some embodiments, the first reactant of the offer and the second reactant, first reactant and described
Two reactants carry out reacting the step of generating electroluminescent material
B1, the first reactant is provided;
B2, it provides including R2The compound of group, first reactant and it is described include R2The compound of group reacts life
At the second intermediate product, the structural formula of second intermediate product isAnd
B3, it provides including R1The compound of group, second intermediate product and it is described include R1The compound of group reacts
The electroluminescent material is generated, the structural formula of the electroluminescent material is
First reactant and it is described include R2The reaction equation that the compound reaction of group generates the second intermediate product can
With are as follows:
The R2It includes R that-H, which is described,2The compound of group.
The mole of first reactant and it is described include R2The corresponding relationship of the mole of the compound of group is 2 millis
The described of corresponding -3 mmoles of 1 mmoles of first reactant for -5 mmoles of rubbing includes R2The compound of group.In some embodiments
In, the mole of first reactant and it is described include R2The corresponding relationship of the mole of the compound of group can be 4 millis
The described of corresponding 1.5 mmoles of first reactant to rub includes R2First reactant pair of the compound of group, 3 mmoles
Answering the described of 1.5 mmoles includes R2The compound of group or the described of 3 moles of 5 moles of first reactant correspondence include R2
The compound of group.
First reactant and it is described include R2The compound of group reacts in the 4th solvent to be produced among generation second
Object.4th solvent includes tetrahydrofuran, toluene, ethyl alcohol, ethylene, perchloroethylene, trichloro ethylene, acetone, ethylene glycol
The combination of one or more of ether and triethanolamine.
There is the 4th additive in 4th solvent.4th additive includes potassium carbonate, four triphenyl phosphorus palladiums, carbon
Sour caesium, potassium hydroxide, sodium hydride, sodium hydroxide, sodium tert-butoxide (NaOt- Bu) and one or more of sodium bicarbonate group
It closes.
Second intermediate product and it is described include R1The compound reaction of group generates the anti-of the electroluminescent material
Ying Shike with are as follows:
The R1It includes R that-H, which is described,1The compound of group.
The mole of second intermediate product and it is described include R1The corresponding relationship of the mole of the compound of group is 1
The described of corresponding 1 mmoles of second intermediate product of -3 mmoles of mmoles includes R1The compound of group.In some embodiments,
The mole of second intermediate product and it is described include R1The corresponding relationship of the mole of the compound of group can be 5 mmoles
The described of corresponding 5 mmoles of second intermediate product include R1The compound of group, 2 moles of second intermediate product pair
Answer 1 mole it is described include R1The compound of group or corresponding the described of 1.5 mmoles of second intermediate product of 1 mmoles include
R1The compound of group.
Second intermediate product and it is described include R1It is described electroluminescent that the compound of group reacts generation in the 5th solvent
Luminescent material.5th solvent includes tetrahydrofuran, toluene, ethyl alcohol, ethylene, perchloroethylene, trichloro ethylene, acetone, N, N-
The combination of one or more of dimethylformamide, ethylene glycol ether and triethanolamine.
There is the 5th additive in 5th solvent.5th additive includes potassium carbonate, four triphenyl phosphorus palladiums, iodine
Change cuprous, cesium carbonate, potassium hydroxide, 1,10- ferrosin, sodium hydride, sodium hydroxide, sodium tert-butoxide (NaOt- Bu), potassium carbonate and
The combination of one or more of sodium bicarbonate.
In one embodiment, by the second reactantIt is dissolved in 20 milliliter -35
In 4th solvents tetrahydrofurane of milliliter, it is slow added into the 4th catalyst sodium hydride, in room temperature condition and under nitrogen protection,
Reaction 20-50 minutes, is then added the first reactant of 2 mmolesThe reaction was continued 12 hours, including
Second intermediate productMixture.It will include second intermediate productMixture be cooled to room temperature and pour into distilled water, with the 5th extractant into
Then row extraction is washed using the 5th detergent, then is dried using the 5th desiccant, then chromatographed again, obtains the
Then five crude products carry out affording second intermediate product using the 4th eluant, eluentSecond intermediate productIt is solid for white
Body, yield 71%.
5th extractant can be the combination of one or more of methylene chloride, chloroform and acetone.Institute
Stating the 5th detergent can be the combination of one or more of saturated salt solution, saturation potassium chloride and distilled water.Described 5th
Desiccant can be anhydrous sodium sulfate, anhydrous magnesium sulfate, anhydrous calcium chloride, dead plaster, Anhydrous potassium carbonate and five oxidations two
The combination of one or more of phosphorus.5th eluant, eluent is one or more of methylene chloride, ethyl alcohol and chloroform
Combination.
In the present embodiment, the 5th extractant can be methylene chloride.5th detergent can be saturation
Saline solution.5th desiccant can be anhydrous sodium sulfate.4th eluant, eluent is the mixture of methylene chloride and ethyl alcohol.
The second intermediate product of 1 mmoles is added in the reaction vesselWith 1 mmoles
It is described include R1The compound of groupThe 5th catalyst is added, the 5th catalyst includes 5 millis
Then 15 milliliters of the 5th solvent N, N- is added in 1, the 10- ferrosin of the cuprous iodide, 5 mmoles that rub and the potassium carbonate of 10 mmoles
Dimethylformamide reacts 24 hours under 160 degrees Celsius under nitrogen protection, obtains including the electroluminescent materialMixture, by the electroluminescent materialMixture be cooled to room temperature after, using the 6th extraction it is molten
Agent is extracted, and is then washed using the 6th detergent, then is dried using the 6th desiccant, then carries out layer again
Analysis, obtains the 6th crude product, then is eluted to obtain the electroluminescent material using the second eluentThe electroluminescent materialFor white solid, yield 50%.
6th extractant can be the combination of one or more of methylene chloride, chloroform and acetone.Institute
Stating the 6th detergent can be the combination of one or more of saturated salt solution, saturation potassium chloride and distilled water.Described 6th
Desiccant can be anhydrous sodium sulfate, anhydrous magnesium sulfate, anhydrous calcium chloride, dead plaster, Anhydrous potassium carbonate and five oxidations two
The combination of one or more of phosphorus.Second eluent is one of methylene chloride, ethyl alcohol, petroleum ether and chloroform
Or several combination.
In the present embodiment, the 6th extractant can be methylene chloride.6th detergent can be distillation
Water.6th desiccant can be anhydrous sodium sulfate.Second eluent is the mixing of petroleum ether, methylene chloride and ethyl alcohol
Object.
Fig. 1-4 is please referred to, Fig. 1-4 is the photoluminescence spectra of the electroluminescent material provided herein.It please join
Table 1 is read, table 1 is the photophysical property of the electroluminescent material provided herein.
Table 1
Wherein, compound one isCompound two isCompound three isCompound four isPL Peak is the fluorescence spectrum of the electroluminescent material
Crest value, S1For minimum singlet level value, T1For lowest triplet state energy level value, EST=S1-T1, HOMO is that highest occupies point
The energy level value of sub-track, LUMO are the energy level value of lowest unoccupied molecular orbital.
The emission peak of the compound one is 440nm, and the emission peak of the compound two is 437nm, the compound three
Emission peak be 427nm, the emission peak of the compound four is 429nm.Electroluminescent material provided herein is issued
Light be in blue region.
Referring to Fig. 5, the application provides a kind of luminescent device 100.The luminescent device 100 includes substrate layer 11, hole
Transmission and implanted layer 12, luminescent layer 13, electron-transport and hole blocking layer 14, electron injecting layer 15 and cathode layer 16.
The substrate layer 11 includes substrate 111 and anode layer 112.The substrate 111 can be glass substrate or transparent modeling
Expect substrate.The anode layer 112 is set on the substrate 111.The anode layer 112 can be indium tin oxide material.
The hole transport and implanted layer 12 are set on the anode layer 112.The hole transport and implanted layer 12 can
Think poly- 3,4-ethylene dioxythiophene: poly styrene sulfonate (poly (3,4-ethylenedioxythiophene): poly
(styrenesulfonate), PEDOT:PSS).The thickness of the hole transport and implanted layer 12 can be 40 nanometers.
The luminescent layer 13 is set in the hole transport and implanted layer 12.The luminescent layer 13 includes the electroluminescent hair
The structural formula of luminescent material, the electroluminescent material is Wherein, the R1Structural formula beThe R2
Structural formula beThe thickness of the luminescent layer 13 can be 40 nanometers.
The electron-transport and hole blocking layer 14 are set on the luminescent layer 13.The electron-transport and hole barrier
Layer 14 can be 1,3,5- tri- (1- phenyl -1H- benzimidazolyl-2 radicals-yl) benzene (1,3,5-Tris (1-phenyl-1H-
Benzimidazol-2-yl) benzene, TPBi).The thickness of the electron-transport and hole blocking layer 14 can be 50 nanometers.
The electron injecting layer 15 is set in the electron-transport and hole blocking layer 14.The electron injecting layer 15 can
Think CsCO3.The thickness of the electron injecting layer 15 can be 2 nanometers.
The cathode layer 16 is set on the electron injecting layer 15.The cathode layer 16 can be Al.The cathode layer
Thickness can be 100 nanometers.
According to means known in the art making devices one to device four, table 2 is please referred to, table 2 is hair provided herein
The performance data table of optical device.
Table 2
Wherein, the device one is the luminescent device for including compound one, and the device two is the hair for including compound two
Optical device, the device three are the luminescent device for including compound three, and the device four is the luminescent device for including compound four.
The application provides the preparation method and luminescent device of a kind of electroluminescent material, electroluminescent material, using benzene cyanogen
Group is as electroluminescent material main body, using carbazole group as branch, to reduce the phase in each molecule between main body
Interaction not only restrained effectively molecule reunion, but also can have the function that equilbrium carrier transmits, and realize luminous efficiency
Electroluminescent material high, that blue light can be issued, meanwhile, the carbazole group of branch further includes the functional group with alkyl chain, institute
It states functional group and increases the dissolubility of molecule, to achieve the purpose that prepare luminescent device using wet process.
The application embodiment is provided above and is discussed in detail, principle of the specific case to the application used herein
And embodiment is expounded, the explanation of embodiment of above is merely used to help understand the application.Meanwhile for this field
Technical staff, according to the thought of the application, there will be changes in the specific implementation manner and application range, to sum up institute
It states, the contents of this specification should not be construed as limiting the present application.
Claims (10)
1. a kind of electroluminescent material, which is characterized in that the structural formula of the electroluminescent material isWherein, the R1Knot
Structure formula isThe R2Structural formula be
2. a kind of preparation method of electroluminescent material characterized by comprising
The first reactant and the second reactant are provided, first reactant and second reactant carry out described in reaction generation
Electroluminescent material, wherein the structural formula of first reactant isThe X1For F, Cl and Br
One of, the X2For for one of F, Cl and Br, the X2Atomic number be more than or equal to the X1Atomic number,
Second reactant be include R1The compound of group and/or including R2The compound of group, the knot of the electroluminescent material
Structure formula isWherein, described
R1Structural formula beThe R2Structural formula be
3. the preparation method of electroluminescent material as claimed in claim 2, which is characterized in that as the X2Atomic number etc.
In the X1Atomic number when, second reactant be include R1The compound of group or compound including R2 group, institute
The structural formula for stating electroluminescent material is
4. the preparation method of electroluminescent material as claimed in claim 3, which is characterized in that mole of first reactant
Amount and the corresponding relationship of the mole of second reactant are corresponding -3 mmoles of 1 mmoles of first reactant of 2-10 mmoles
Second reactant.
5. the preparation method of electroluminescent material as claimed in claim 4, which is characterized in that first reactant and described
Second reactant carries out reaction in the first solvent and generates the electroluminescent material, first solvent include tetrahydrofuran,
One or more of toluene, ethyl alcohol, ethylene, perchloroethylene, trichloro ethylene, acetone, ethylene glycol ether and triethanolamine
Combination.
6. the preparation method of electroluminescent material as claimed in claim 5, which is characterized in that have the in first solvent
One additive, first additive include potassium carbonate, four triphenyl phosphorus palladiums, cesium carbonate, potassium hydroxide, sodium hydride, hydroxide
Sodium, sodium tert-butoxide (NaOt- Bu) and one or more of sodium bicarbonate combination.
7. the preparation method of electroluminescent material as claimed in claim 2, which is characterized in that as the X2Atomic number it is big
In the X1Atomic number when, second reactant be include R1The compound of group and including R2The compound of group, institute
The structural formula for stating electroluminescent material is
8. the preparation method of electroluminescent material as claimed in claim 7, which is characterized in that the first reactant of the offer and
Second reactant, first reactant and second reactant carry out reacting the step of generating electroluminescent material
First reactant is provided;
There is provided includes R1The compound of group, first reactant and it is described include R1The compound reaction of group generates first
The structural formula of intermediate product, first intermediate product isAnd
There is provided includes R2The compound of group, first intermediate product and it is described include R2The compound reaction of group generates institute
Electroluminescent material is stated, the structural formula of the electroluminescent material is
9. the preparation method of electroluminescent material as claimed in claim 7, which is characterized in that the first reactant of the offer and
Second reactant, first reactant and second reactant carry out reacting the step of generating electroluminescent material
First reactant is provided;
There is provided includes R2The compound of group, first reactant and it is described include R2The compound reaction of group generates second
The structural formula of intermediate product, second intermediate product isAnd
There is provided includes R2The compound of group, second intermediate product and it is described include R2The compound reaction of group generates institute
Electroluminescent material is stated, the structural formula of the electroluminescent material is
10. a kind of luminescent device characterized by comprising
Substrate layer, the substrate layer include substrate and anode layer, and the anode layer is set on the substrate;
Hole transport and implanted layer, the hole transport and implanted layer are set on the anode layer;
Luminescent layer, the luminescent layer is set to the hole transport and implanted layer is set;
Electron-transport and hole blocking layer, the electron-transport and hole blocking layer are set on the luminescent layer;
Electron injecting layer, the electron injecting layer are set on the electron-transport and hole blocking layer;
Cathode layer, the cathode layer are set on the electron injecting layer;
The luminescent layer includes the electroluminescent material, wherein the structural formula of the electroluminescent material isWherein, the R1Knot
Structure formula isThe R2Structural formula be
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910588608.3A CN110229094B (en) | 2019-07-01 | 2019-07-01 | Electroluminescent material, preparation method of electroluminescent material and luminescent device |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910588608.3A CN110229094B (en) | 2019-07-01 | 2019-07-01 | Electroluminescent material, preparation method of electroluminescent material and luminescent device |
Publications (2)
Publication Number | Publication Date |
---|---|
CN110229094A true CN110229094A (en) | 2019-09-13 |
CN110229094B CN110229094B (en) | 2021-03-16 |
Family
ID=67857932
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201910588608.3A Active CN110229094B (en) | 2019-07-01 | 2019-07-01 | Electroluminescent material, preparation method of electroluminescent material and luminescent device |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN110229094B (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110903236A (en) * | 2019-12-17 | 2020-03-24 | 武汉大学 | Dark blue electroluminescent material and preparation method and application thereof |
CN111978300A (en) * | 2020-07-24 | 2020-11-24 | 山西华辉光电科技有限公司 | Phosphorescence luminescent main body material based on carbazole and benzonitrile and application thereof |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108586318A (en) * | 2018-01-16 | 2018-09-28 | 东南大学 | A kind of hot activation delayed fluorescence material of solution processable and preparation method thereof |
CN109503458A (en) * | 2018-11-27 | 2019-03-22 | 淮海工学院 | A kind of preparation method and applications of blue light autonomous agent heat shock activating compound |
-
2019
- 2019-07-01 CN CN201910588608.3A patent/CN110229094B/en active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108586318A (en) * | 2018-01-16 | 2018-09-28 | 东南大学 | A kind of hot activation delayed fluorescence material of solution processable and preparation method thereof |
CN109503458A (en) * | 2018-11-27 | 2019-03-22 | 淮海工学院 | A kind of preparation method and applications of blue light autonomous agent heat shock activating compound |
Non-Patent Citations (3)
Title |
---|
XINXIN BAN ET AL.: "Constructing a Novel Dendron for a Self-Host Blue Emitter with Thermally Activated Delayed Fluorescence: Solution-Processed Nondoped Organic Light-Emitting Diodes with Bipolar Charge Transfer and Stable Color Purity", 《CHEM.ASIAN J.》 * |
XINXIN BAN ET AL.: "Design of encapsulated hosts and guests for highly efficient blue and green thermally activated delayed fluorescence OLEDs based on a solution-process", 《CHEM.COMMUN.》 * |
XINXIN BAN ET AL.: "Self-Host Blue Dendrimer Comprised of Thermally Activated Delayed Fluorescence Core and Bipolar Dendrons for Efficient Solution-Processable Nondoped Electroluminescence", 《ACS APPL.MATER.INTERFACES》 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110903236A (en) * | 2019-12-17 | 2020-03-24 | 武汉大学 | Dark blue electroluminescent material and preparation method and application thereof |
CN110903236B (en) * | 2019-12-17 | 2022-11-29 | 武汉大学 | Dark blue electroluminescent material and preparation method and application thereof |
CN111978300A (en) * | 2020-07-24 | 2020-11-24 | 山西华辉光电科技有限公司 | Phosphorescence luminescent main body material based on carbazole and benzonitrile and application thereof |
Also Published As
Publication number | Publication date |
---|---|
CN110229094B (en) | 2021-03-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Chen et al. | Nitrogen heterocycle-containing materials for highly efficient phosphorescent OLEDs with low operating voltage | |
KR102052739B1 (en) | Phophorescene compounds and organic light emitting diode devices using the same | |
CN102593374A (en) | Electron transport material and organic light-emitting device | |
CN110229094A (en) | Electroluminescent material, the preparation method of electroluminescent material and luminescent device | |
CN110078754A (en) | Compound, display panel and display device | |
CN104513247A (en) | Benzo [c] benzo [3,4] carbazol derivatives and uses | |
CN106867520B (en) | Based on heteroaromatic simultaneously -2-S, the bipolarity small molecule emitter material and its preparation method of S- dioxydibenze bithiophene unit and application | |
CN104673276A (en) | Organic luminescent material and application thereof | |
CN110283178B (en) | Heterocyclic compound, synthetic method thereof and organic electroluminescent element containing heterocyclic compound | |
CN105237519A (en) | Mazarine electroluminescent compound, and preparation method and application thereof | |
CN110016027A (en) | Electroluminescent material, the preparation method of electroluminescent material and luminescent device | |
CN109251745A (en) | Electroluminescent material, the preparation method of electroluminescent material and luminescent device | |
CN106893578B (en) | Bipolar small-molecule luminescent material based on 3, 7-naphtho-dibenzothiophene unit and preparation method and application thereof | |
CN109321234A (en) | Electroluminescent material, the preparation method of electroluminescent material and luminescent device | |
CN109988099A (en) | Electroluminescent material, the preparation method of electroluminescent material and luminescent device | |
CN114409700B (en) | Bipolar main material based on diphenyl sulfide thermal excitation delayed fluorescence, synthesis method and application thereof | |
CN107759624A (en) | New asymmetric aryl boron organic photoelectric functional material and preparation method and application | |
CN107325811A (en) | Thermal excitation delayed fluorescence material and preparation method and application based on carbazole and phosphine oxygen | |
CN113461693A (en) | Organic compound, hole injection material and application thereof | |
CN107129486B (en) | Bipolar blue light small molecule luminescent material based on naphtho-8-S, S-dioxo dibenzothiophene unit and preparation method and application thereof | |
EP3802483A1 (en) | Cyano-derivatized oligonophenylacetylene-based fluorescent small molecules suitable for use in organic light-emitting diode applications and their use in organic light-emitting diode applications | |
CN110437208A (en) | A kind of bis- carbazole benzene class phosphorescent light body material of 1,3-, its synthetic method and its application | |
CN110128417A (en) | Compound, display panel and display device | |
CN110078757A (en) | A kind of aryl silicon organic photoelectrical material and the preparation method and application thereof | |
CN109748913A (en) | Electroluminescent material based on carbazole and pyridine construction unit |
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 |