CN108864013A - A kind of aromatic amine compound containing dibenzofurans and application thereof and luminescent device - Google Patents
A kind of aromatic amine compound containing dibenzofurans and application thereof and luminescent device Download PDFInfo
- Publication number
- CN108864013A CN108864013A CN201811023324.1A CN201811023324A CN108864013A CN 108864013 A CN108864013 A CN 108864013A CN 201811023324 A CN201811023324 A CN 201811023324A CN 108864013 A CN108864013 A CN 108864013A
- Authority
- CN
- China
- Prior art keywords
- layer
- aromatic amine
- amine compound
- dibenzofurans
- organic
- 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.)
- Pending
Links
- VFUDMQLBKNMONU-UHFFFAOYSA-N c(cc1)cc(c2c3cccc2)c1[n]3-c(cc1)ccc1-c(cc1)ccc1-[n]1c2ccccc2c2ccccc12 Chemical compound c(cc1)cc(c2c3cccc2)c1[n]3-c(cc1)ccc1-c(cc1)ccc1-[n]1c2ccccc2c2ccccc12 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- 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
- C07D405/12—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 chain containing hetero atoms as chain links
-
- 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
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- 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]
- H10K50/17—Carrier injection layers
-
- 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]
- H10K50/18—Carrier blocking 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- 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
- C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- 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
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Chemistry (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention provides a kind of aromatic amine compounds containing dibenzofurans, have the following structure formula:The aromatic amine compound containing dibenzofurans has preferable thermal stability, high-luminous-efficiency, high luminance purity, can be applied to organic electroluminescence device, solar battery, Organic Thin Film Transistors or organophotoreceptorswith field.The present invention also provides a kind of organic electroluminescence devices, the device includes anode, cathode and organic layer, organic layer includes at least one layer in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer and electron transfer layer, the at least one layer aromatic amine compound containing dibenzofurans containing such as structural formula I in organic layer has the advantages that electroluminescent efficiency is good and excitation purity is excellent and the service life is long using the organic electroluminescence device of the aromatic amine compound production containing dibenzofurans.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of aromatic amine compound containing dibenzofurans
And application thereof, further relate to a kind of luminescent device.
Background technique
Organic electroluminescence device (OLEDs) is between two metal electrodes by spin coating or vacuum evaporation deposition one
The device that layer organic material is prepared, a classical three layer organic electroluminescence device include hole transmission layer, luminescent layer
And electron transfer layer.The electronics generated by cathode is followed to be incorporated in through electron transfer layer through hole transmission layer in the hole generated by anode
Luminescent layer forms exciton, then shines.Organic electroluminescence device can according to need the material by changing luminescent layer to adjust
Section emits the light of various needs.
Organic electroluminescence device has self-luminous, wide viewing angle, low energy consumption, efficiency as a kind of novel display technology
High, thin, rich in color, fast response time, Applicable temperature range be wide, low driving voltage, can make flexible and transparent
Display panel and the particular advantages such as environmental-friendly can be applied on flat-panel monitor and a new generation's illumination, be can also be used as
The backlight of LCD.
Since the invention at the bottom of the 1980s, organic electroluminescence device is industrially applied, such as
As screens such as camera and mobile phones, but current OLED device, due to low efficiency, it is wider that the factors such as service life is short restrict it
General application, especially large screen display, it is therefore desirable to improve the efficiency of device.And restrict one of key factor just
It is the performance of the electroluminescent organic material in organic electroluminescence device.It is voltage-operated in application additionally, due to OLED device
When, Joule heat can be generated, so that organic material is easy to happen crystallization, affects service life and the efficiency of device, therefore, it is also desirable to
Develop the electroluminescent organic material of stability and high efficiency.
Organic electrophosphorescenpolymer phenomenon, breaches theoretical limitation of the organic electroluminescent quantum efficiency lower than 25%, and promotion is arrived
100% (Baldo M.A., Forrest S.R.Et al, Nature, 1998,395,151-154), application also greatly mention
The high efficiency of organic electroluminescence device.Generally, electroluminescent phosphorescence needs commonly to be used as phosphorus using host-guest system technology
The CBP (4,4'-bis (9-carbazolyl)-biphenyl) of light material of main part has efficient and high triplet energy level, when its work
Based on material when, triplet energy state effectively can be transferred to object phosphorescent light-emitting materials from light emitting host material.But by
It is easily transmitted and the characteristic of electronics difficulty flowing in the hole of CBP, so that the charge unbalance of luminescent layer, as a result reduces the effect of device
Rate.
In organic electroluminescence device, the introducing of hole mobile material and injection material can be effectively reduced positive electricity
Lotus is transferred to the ability of luminescent layer from anode, improves the efficiency and thermostabilization of device.Traditional hole-injecting material, such as copper
Phthalocyanine (CuPc), degradation is slow, and preparation energy consumption is high, is unfavorable for environmental protection, and it can absorb light, influence device
Efficiency.NPB etc. original hole mobile material, thermal stability is poor, also largely influences device lifetime.Thus, it needs
Develop the electroluminescent organic material of efficient stable.
Summary of the invention
The present invention provides a kind of aromatic amine compounds containing dibenzofurans, are the chemical combination for having the following structure Formulas I
Object:For the compound for having the following structure Formulas I:
Wherein, Ar1-Ar3Independently selected from replace perhaps unsubstituted C6-C30 aryl replace or it is unsubstituted
The carbazyl of the triaromatic amine base of C18-C30, substitution or unsubstituted C12-C30.
Optionally, the aryl is selected from phenyl, diphenyl, naphthalene, naphthylphenyl, xenyl, three simultaneously phenyl, anthryl, phenanthrene
Base, pyrenyl, base, fluoranthene base, acenaphthenyl, acenaphthylene base, (9,9- dialkyl group) fluorenyl, (9,9- bis- replaces or unsubstituted aryl)
Fluorenyl, substitution or unsubstituted dibenzothiophene and substitution or unsubstituted dibenzofuran group.
Optionally, Ar1Selected from phenyl, naphthalene, xenyl.
Optionally, the Ar1Further replaced by the alkyl of C1-C12.
Optionally, the aromatic amine compound containing dibenzofurans is the compound of following structural 1-28:
Aromatic amine compound containing dibenzofurans of the invention can be reacted by Buchwald-Hartwig and Wu Er
Graceful anti-, suzkui should be prepared.
Aromatic amine compound containing dibenzofurans of the invention can be applied to organic electroluminescence device, solar-electricity
Pond, Organic Thin Film Transistors or organophotoreceptorswith field.
The present invention also provides a kind of organic electroluminescence device, which includes anode, cathode and organic layer, organic layer
Include at least one in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, exciton barrier-layer and electron transfer layer
Layer, at least one layer of aromatic amine compound containing dibenzofurans containing as described in structural formula I in the organic layer.
Wherein organic layer is luminescent layer;
Or organic layer is luminescent layer and electron transfer layer;
Or organic layer is luminescent layer, electron transfer layer and electron injecting layer;
Or organic layer is hole transmission layer and luminescent layer;
Or organic layer is hole injection layer, hole transmission layer and luminescent layer;
Or organic layer is hole transmission layer, luminescent layer and electron transfer layer;
Or organic layer is hole injection layer, hole transmission layer, luminescent layer and electron transfer layer;
Or organic layer is hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer;
Or organic layer is hole injection layer, hole transmission layer, barrier layer, luminescent layer, electron transfer layer and electron injection
Layer;
Or organic layer is hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and hole blocking layer;
Or organic layer is hole transmission layer, luminescent layer, electron injecting layer and hole blocking layer.
Further alternative, the layer where the aromatic amine compound containing dibenzofurans is hole transmission layer.
The aromatic amine compound containing dibenzofurans as described in structural formula I is used alone, or mixes with other compounds
It uses;The aromatic amine compound containing dibenzofurans as described in structural formula I can be used alone one such compound,
It can be simultaneously using two or more the compound in structural formula I;A kind of containing selected from structural formula 1-28 is used alone
The aromatic amine compound of dibenzofurans, or the two or more fragrance containing dibenzofurans selected from structural formula 1-28 are used simultaneously
Amine compounds.
Still optionally further, organic electroluminescence device of the invention include anode, hole injection layer, hole transmission layer,
Luminescent layer, electron transfer layer, electron injecting layer and cathode wherein contain one or more kinds of structural formula I's in luminescent layer
Compound;It is further preferred that the compound containing one or more kinds of structural formula 1-28 in luminescent layer.
The overall thickness of organic electroluminescence device organic layer of the invention is 1-1000nm, preferably 50-500nm.
When having the compound of structural formula I using the present invention, can arrange in pairs or groups makes organic electroluminescence device of the invention
With other materials, such as in hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and barrier layer
Deng, and obtain blue and green light, yellow light, feux rouges or white light.
The hole transmission layer and hole injection layer of organic electroluminescence device of the present invention, material requested have good hole
Transmission performance can effectively be transferred to hole on luminescent layer from anode.Except it is of the invention there is Compounds of structural formula I in addition to,
It can also include other small molecules and macromolecular organic compound, including but not limited to carbazole compound, triaromatic amine chemical combination
Object, benzidine compound, compound of fluorene class, phthalocyanine-like compound, the miscellaneous triphen of six cyano six
(hexanitrilehexaazatriphenylene), tetra- cyanogen dimethyl-parabenzoquinone (F4- of 2,3,5,6- tetra- fluoro- 7,7', 8,8'-
TCNQ), polyvinyl carbazole, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of organic electroluminescence device of the invention has the good characteristics of luminescence, can be adjusted according to the needs
The range of visible light.Following compound can be contained, but not limited to this, naphthalene compounds, pyrene compound, fluorenes class chemical combination
Object, luxuriant and rich with fragrance class compound,Class compound, glimmering anthracene compound, anthracene compound, pentacene class compound, class compound, two
Aromatic ethylene class compound, aminated compounds, benzimidazoles compound, furfuran compound, has triphenylamine ethylene compounds
Machine metallo-chelate.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires good electronic transmission performance, energy
It reaches in effectively electronics from cathode transport to luminescent layer, there is very big electron mobility.There is this hair in addition to can be used
Outside bright compound, it is also an option that following compound, but not limited to this:Oxa- oxazole, thiazole compound, triazole
Compound, three nitrogen piperazine class compounds, triazine class compound, quinoline class compound, phenodiazine anthracene compound, siliceous heterocyclic
Compound, quinolines, ferrosin class compound, metallo-chelate (such as Alq3), fluorine substituted benzene compound, benzo miaow
Azole compounds.
Electronics effectively can be injected into organic layer from cathode by the electron injecting layer of organic electroluminescence device of the present invention
In, it is mainly selected from the alkali metal perhaps compound of alkali metal or compound or alkali selected from alkaline-earth metal or alkaline-earth metal
Metal complex can choose following compound, and but not limited to this:Alkali metal, alkaline-earth metal, rare earth metal, alkali metal
Oxide or halide, the oxide of alkaline-earth metal or halide, the oxide of rare earth metal or halide, alkali metal
Or the organic complex of alkaline-earth metal;Preferably lithium, lithium fluoride, lithia, lithium nitride, 8-hydroxyquinoline lithium, caesium, carbonic acid
Caesium, 8-hydroxyquinoline caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, magnesia, these compounds can individually make
With that can also be used with mixture, can also be used cooperatively with other electroluminescent organic materials.
Each layer of organic layer in organic electroluminescence device of the invention can be steamed by vacuum vapour deposition, molecular beam
It is prepared by the modes such as plating method, the dip coating for being dissolved in solvent, spin-coating method, stick coating method or inkjet printing.Metal motor can be made
It is prepared with vapour deposition method or sputtering method.
Device experimental shows aromatic amine compound containing dibenzofurans of the present invention as described in structural formula I, has preferable
Thermal stability, high-luminous-efficiency, high luminance purity.Using the organic electroluminescence of the aromatic amine compound production containing dibenzofurans
Luminescent device has the advantages that electroluminescent efficiency is good and excitation purity is excellent and the service life is long.
Detailed description of the invention
Fig. 1 is the organic electroluminescence device structural schematic diagram of the embodiment of the present invention,
Wherein, 110 be glass substrate, and 120 be anode, and 130 be hole injection layer, and 140 be hole transmission layer, and 150 be hair
Photosphere, 160 be electron transfer layer, and 170 be electron injecting layer, and 180 be cathode.
Specific embodiment
In order to describe the present invention in more detail, spy lifts following example, and but not limited to this.
Embodiment 1
The synthetic route of compound 1
The synthetic method of intermediate 2-1
In there-necked flask, chlorobenzoyl chloride (30.8g, 0.22mol), dry methylene chloride (250mL) is added, is protected in nitrogen
Under shield, alchlor (35g, 0.26mol) is added at 0 DEG C, then the bromo- dibenzofurans of 2- (49g, 0.2mol) is added portionwise, adds
Finish stirring 2 hours, add water quenching reaction, organic phase is crossed silica gel after washing liquid separation, is spin-dried for, crude product ethyl alcohol recrystallization obtains
Off-white powder 48g, yield 69%.
The synthetic method of intermediate 2-2
In flask, it is added intermediate 2-1 (35g, 100mmol), anhydrous tetrahydro furan (400mL), under nitrogen protection
It is cooled to 0 DEG C, is slowly added to 2- xenyl magnesium bromide grignard reagent (120mmol), is heated to reflux stirring 3 hours, it is cooling, then
It is slowly added to the dilute hydrochloric acid solution of 1N, pH value is improved to 7, is extracted with dichloromethane, dries, being concentrated, glacial acetic acid (200mL) is added
It with concentrated hydrochloric acid (10mL), is heated to reflux 5 hours, cooling removes solvent, Jia Shui, is extracted with dichloromethane, dries, being concentrated, thick to produce
Object obtains product 10g, yield 21% through column chromatographic purifying.
The synthetic method of compound 2
In flask, it is added intermediate 2-2 (3g, 6.2mmol), 4,4 '-di-t-butyl diphenylamines (1.9g, 7mmol), uncles
Sodium butoxide (1.2g, 12mmol), palladium acetate (0.1g), X-phos (0.3g), toluene (30mL) are heated to reflux 5 under nitrogen protection
Hour, it is cooling, solvent is removed, crude by column chromatography purifies to obtain 3.2g, yield 76%.
The synthetic method of other embodiments such as compound 2, be all use intermediate 2-2 as raw material, then with other
Amine reaction, table 1 specific as follows:
Embodiment 9-16
The preparation of organic electroluminescence device
OLED is prepared using the compound of embodiment
Firstly, by electrically conducting transparent ito glass substrate 110 (having anode 120 above) (the limited public affairs of South China glass group share
Department) successively pass through:Deionized water, ethyl alcohol, acetone and deionized water were cleaned, then with oxygen plasma treatment 30 seconds.
Then, on ITO spin coating 45nm thickness PEDOT:PSS (Polyglycolic acid fibre-is poly- (styrene sulfonate)) is
It is 30 minutes dry at 130,150 DEG C of hole injection layer.
Then, the compounds of this invention of 40nm thickness is deposited on hole injection layer as hole mobile material 140.
Then, the luminescent layer 150 of 30nm thickness is deposited on electronic barrier layer, wherein luminescent material based on CBP, and with
The Ir (ppy) that weight ratio is 8%3Guest materials is adulterated as phosphorescence.
Then, the TMPYPB of 40nm thickness is deposited on the light-emitting layer as electron transfer layer 160.
Finally, vapor deposition 1nm LiF is electron injecting layer 170 and 80nm Al as device cathodes 180.
Prepared device (structural schematic diagram is shown in Fig. 1) with Photo Research PR650 spectrometer measure
100mA/cm2Current density under external quantum efficiency be such as table 2.
Comparative example 1
In addition to use NPB, HT1 replace the compounds of this invention as hole mobile material other than, method that comparative example prepares device
As embodiment 9-16.
Table 2
Embodiment | Compound | Current efficiency (100%) | Luminescent color |
9 | 2 | 7.1 | Green light |
10 | 10 | 7.4 | Green light |
11 | 12 | 7.2 | Green light |
12 | 13 | 7.3 | Green light |
13 | 14 | 7.5 | Green light |
14 | 18 | 7.9 | Green light |
15 | 21 | 8.0 | Green light |
16 | 23 | 7.8 | Green light |
Comparative example 1 | NPB | 6.1 | Green light |
Comparative example 2 | HT1 | 6.0 | Green light |
The structural formula of compound described in device is as follows:
From Table 2, it can be seen that the triaromatic amine compound of the invention containing dibenzofurans is used for organic electroluminescent
Device can reduce operating voltage, improve device efficiency, be the hole mobile material with excellent performance.As described above, this hair
Bright compound has high stability, and the organic electroluminescence device of preparation has high efficiency and optical purity.
The preferred embodiment of the present invention has been described in detail above.It should be appreciated that those skilled in the art without
It needs creative work according to the present invention can conceive and makes many modifications and variations.Therefore, all technologies in the art
Personnel are available by logical analysis, reasoning, or a limited experiment on the basis of existing technology under this invention's idea
Technical solution, all should be within the scope of protection determined by the claims.
Claims (10)
1. a kind of aromatic amine compound containing dibenzofurans, which is characterized in that be the compound for having the following structure Formulas I:
Wherein, Ar1-Ar3Independently selected from the aryl substitution or unsubstituted C18-C30 for replacing perhaps unsubstituted C6-C30
Triaromatic amine base, substitution or unsubstituted C12-C30 carbazyl.
2. as described in claim 1 containing the aromatic amine compound of dibenzofurans, which is characterized in that the aryl is selected from benzene
Base, diphenyl, naphthalene, naphthylphenyl, xenyl, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, acenaphthenyl, acenaphthylene
Base, (9,9- dialkyl group) fluorenyl, (9,9- bis- replaces or unsubstituted aryl) fluorenyl, substitution or unsubstituted dibenzo thiophene
Pheno base and substitution or unsubstituted dibenzofuran group.
3. as described in claim 1 containing the aromatic amine compound of dibenzofurans, which is characterized in that Ar1Selected from phenyl, naphthalene,
Xenyl.
4. as claimed in claim 3 containing the aromatic amine compound of dibenzofurans, which is characterized in that the Ar1Further by
The alkyl of C1-C12 replaces.
5. as described in claim 1 containing the aromatic amine compound of dibenzofurans, which is characterized in that be following structural 1-28
Compound:
6. application of the aromatic amine compound described in claim 1 containing dibenzofurans in organic electroluminescence device.
7. a kind of organic electroluminescence device, which includes anode, cathode and organic layer, and organic layer includes luminescent layer, hole
At least one layer in implanted layer, hole transmission layer, hole blocking layer, exciton barrier-layer and electron transfer layer, which is characterized in that institute
It states at least one layer of containing as described in claim 1 containing the aromatic amine compound of dibenzofurans in organic layer.
8. organic electroluminescence device as claimed in claim 7, which is characterized in that furan containing dibenzo described in claim 1
Layer where the aromatic amine compound muttered is hole transmission layer.
9. organic electroluminescence device as claimed in claim 7, which is characterized in that furan containing dibenzo described in claim 1
The aromatic amine compound muttered is used alone, or is used in mixed way with other compounds.
10. organic electroluminescence device as claimed in claim 7, which is characterized in that be used alone a kind of selected from as right is wanted
The aromatic amine compound containing dibenzofurans of structural formula 1-28 described in asking 5, or simultaneously using two or more selected from such as right
It is required that the aromatic amine compound containing dibenzofurans of structural formula 1-28 described in 5.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811023324.1A CN108864013A (en) | 2018-09-03 | 2018-09-03 | A kind of aromatic amine compound containing dibenzofurans and application thereof and luminescent device |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811023324.1A CN108864013A (en) | 2018-09-03 | 2018-09-03 | A kind of aromatic amine compound containing dibenzofurans and application thereof and luminescent device |
Publications (1)
Publication Number | Publication Date |
---|---|
CN108864013A true CN108864013A (en) | 2018-11-23 |
Family
ID=64322963
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201811023324.1A Pending CN108864013A (en) | 2018-09-03 | 2018-09-03 | A kind of aromatic amine compound containing dibenzofurans and application thereof and luminescent device |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN108864013A (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111793001A (en) * | 2019-04-02 | 2020-10-20 | 材料科学有限公司 | Organic compound and organic electroluminescent element comprising same |
EP3792255A1 (en) * | 2019-09-16 | 2021-03-17 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
CN112521360A (en) * | 2020-11-30 | 2021-03-19 | 长春海谱润斯科技股份有限公司 | Arylamine organic compound and organic electroluminescent device thereof |
WO2021141356A1 (en) * | 2020-01-10 | 2021-07-15 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using same, and electronic device thereof |
CN113195465A (en) * | 2018-12-20 | 2021-07-30 | 默克专利有限公司 | Material for electronic devices |
WO2021261946A1 (en) * | 2020-06-26 | 2021-12-30 | 엘티소재주식회사 | Heterocyclic compound and organic light-emitting device using same |
WO2023027479A1 (en) * | 2021-08-23 | 2023-03-02 | 엘티소재주식회사 | Heterocyclic compound and organic light-emitting device using same |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101184822A (en) * | 2005-05-30 | 2008-05-21 | 西巴特殊化学品控股有限公司 | Electroluminescent device |
CN108117543A (en) * | 2016-11-29 | 2018-06-05 | 东进世美肯株式会社 | Compounds and the organic electroluminescence device for including it |
-
2018
- 2018-09-03 CN CN201811023324.1A patent/CN108864013A/en active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101184822A (en) * | 2005-05-30 | 2008-05-21 | 西巴特殊化学品控股有限公司 | Electroluminescent device |
CN108117543A (en) * | 2016-11-29 | 2018-06-05 | 东进世美肯株式会社 | Compounds and the organic electroluminescence device for including it |
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2022515752A (en) * | 2018-12-20 | 2022-02-22 | メルク パテント ゲーエムベーハー | Materials for electronic devices |
JP7543273B2 (en) | 2018-12-20 | 2024-09-02 | メルク パテント ゲーエムベーハー | Materials for Electronic Devices |
CN113195465A (en) * | 2018-12-20 | 2021-07-30 | 默克专利有限公司 | Material for electronic devices |
CN111793001B (en) * | 2019-04-02 | 2023-12-22 | 材料科学有限公司 | Organic compound and organic electroluminescent element comprising same |
CN111793001A (en) * | 2019-04-02 | 2020-10-20 | 材料科学有限公司 | Organic compound and organic electroluminescent element comprising same |
EP3792255A1 (en) * | 2019-09-16 | 2021-03-17 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
US20210083201A1 (en) * | 2019-09-16 | 2021-03-18 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
US11711978B2 (en) * | 2019-09-16 | 2023-07-25 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
WO2021141356A1 (en) * | 2020-01-10 | 2021-07-15 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using same, and electronic device thereof |
KR20220000842A (en) * | 2020-06-26 | 2022-01-04 | 엘티소재주식회사 | Hetero-cyclic compound and organic light emitting device using same |
CN115996915A (en) * | 2020-06-26 | 2023-04-21 | Lt素材株式会社 | Heterocyclic compound and organic light-emitting device using same |
WO2021261946A1 (en) * | 2020-06-26 | 2021-12-30 | 엘티소재주식회사 | Heterocyclic compound and organic light-emitting device using same |
KR102585738B1 (en) | 2020-06-26 | 2023-10-10 | 엘티소재주식회사 | Hetero-cyclic compound and organic light emitting device using same |
CN112521360B (en) * | 2020-11-30 | 2021-12-21 | 长春海谱润斯科技股份有限公司 | Arylamine organic compound and organic electroluminescent device thereof |
CN112521360A (en) * | 2020-11-30 | 2021-03-19 | 长春海谱润斯科技股份有限公司 | Arylamine organic compound and organic electroluminescent device thereof |
WO2023027479A1 (en) * | 2021-08-23 | 2023-03-02 | 엘티소재주식회사 | Heterocyclic compound and organic light-emitting device using same |
KR20230029058A (en) * | 2021-08-23 | 2023-03-03 | 엘티소재주식회사 | Hetero-cyclic compound and organic light emitting device using same |
KR102610155B1 (en) | 2021-08-23 | 2023-12-06 | 엘티소재주식회사 | Hetero-cyclic compound and organic light emitting device using same |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN109053698A (en) | A kind of aromatic amine compound and luminescent device containing dibenzofurans | |
CN105481811B (en) | A kind of compound and its organic electroluminescence device with spiro structure | |
CN108864013A (en) | A kind of aromatic amine compound containing dibenzofurans and application thereof and luminescent device | |
CN108752221A (en) | A kind of triaromatic amine compound containing fluorenes and application thereof and luminescent device | |
CN106831313A (en) | A kind of compound and its organic electroluminescence device with triaryl naphthalene | |
CN107954922A (en) | A kind of two carbazole derivates of xenyl and application thereof and organic electroluminescence device | |
CN109336772A (en) | A kind of triaromatic amine compound containing spiro structure and application thereof and luminescent device | |
CN109535175A (en) | A kind of double triaromatic amine compounds, application and the luminescent device of the spiro structure containing five-membered ring | |
CN109265450A (en) | A kind of organic electroluminescent compounds and luminescent device of the aphthofurans containing benzo | |
CN108658953A (en) | A kind of compound based on dibenzofurans and carbazole and application thereof and luminescent device | |
CN108997239A (en) | A kind of compound of cyano-containing and application thereof and organic electroluminescence device | |
CN108047244A (en) | A kind of snail compound and application thereof and organic electroluminescence device | |
CN109535093A (en) | A kind of trisubstituted benzene based compound and organic electroluminescence device | |
CN108299388A (en) | A kind of phenanthrene derivatives and application thereof and organic electroluminescence device | |
CN107417677A (en) | A kind of carbazole pyridines organic electroluminescent compounds and its organic electroluminescence device | |
CN108752317A (en) | One kind is containing anthracene derivant and application thereof and luminescent device | |
CN106831798B (en) | Compound and its organic electroluminescence device containing five-membered ring structure | |
CN108658789A (en) | A kind of triaromatic amine compound containing fluorenes and application thereof and luminescent device | |
CN109320495A (en) | A kind of double triaromatic amine compounds, application and luminescent device containing spiro structure | |
CN109705021A (en) | A kind of organic electroluminescent compounds of the alkylnaphthalene containing cycloheptyl and application thereof and luminescent device | |
CN108912099A (en) | A kind of compound containing triazine and carbazole and application thereof and organic electroluminescence device | |
CN108003121A (en) | A kind of phenanthrene class compound and application thereof and organic electroluminescence device | |
CN106749289B (en) | A kind of organic electroluminescent compounds and its luminescent device with spiro structure | |
CN108358932A (en) | A kind of nitrogen heterocyclic and application thereof and organic electroluminescence device | |
CN107652223A (en) | A kind of carbazoles organic electroluminescent compounds and its organic electroluminescence device |
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 | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20181123 |
|
RJ01 | Rejection of invention patent application after publication |