CN108752221A - A kind of triaromatic amine compound containing fluorenes and application thereof and luminescent device - Google Patents
A kind of triaromatic amine compound containing fluorenes and application thereof and luminescent device Download PDFInfo
- Publication number
- CN108752221A CN108752221A CN201810650136.5A CN201810650136A CN108752221A CN 108752221 A CN108752221 A CN 108752221A CN 201810650136 A CN201810650136 A CN 201810650136A CN 108752221 A CN108752221 A CN 108752221A
- Authority
- CN
- China
- Prior art keywords
- layer
- amine compound
- compound containing
- containing fluorenes
- triaromatic amine
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- 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
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- 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
- 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]
- H10K50/14—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
- 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
- H10K85/649—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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—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)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The triaromatic amine compound containing fluorenes that the present invention provides a kind of, has the following structure formula：The compound has preferable thermal stability, high-luminous-efficiency, high luminance purity, organic electroluminescence device, solar cell, Organic Thin Film Transistors or organophotoreceptorswith field are can be applied to, the organic electroluminescence device made of the triaromatic amine compound containing fluorenes has the advantages that electroluminescent efficiency is good and excitation purity is excellent and long lifespan.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of triaromatic amine compound and its use containing fluorenes
On the way, a kind of luminescent device is further related to.
Background technology
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 be adjusted as desired by the material for changing luminescent layer
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 with it is 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, since efficiency is low, it is wider that the factors such as service life is short restrict it
General application, especially large screen display.And it is exactly in organic electroluminescence device to restrict one of key factor
The performance of electroluminescent organic material.Additionally, due to OLED device when applying voltage-operated, Joule heat will produce 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 organic electroluminescence of stability and high efficiency
Luminescent material.
Organic electrophosphorescenpolymer phenomenon, breaches theoretical limitation of the organic electroluminescent quantum efficiency less than 25%, and promotion is arrived
100% (Baldo M.A., Forrest S.R.Et al, Nature, 1998,395,151-154), application also greatly carry
The high efficiency of organic electroluminescence device.Usually, electroluminescent phosphorescence needs to use host-guest system technology, is commonly used as phosphorus
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
In the characteristic of the hole of CBP easily transmission and the flowing of electronics difficulty so that as a result the charge unbalance of luminescent layer 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 efficiency and the thermostabilization of device.Traditional hole-injecting material, such as copper
Phthalocyanine (CuPc), degradation is slow, prepares energy consumption height, is unfavorable for environmental protection, and it can absorb light, influence device
Efficiency.Hole mobile material original NPB etc., thermal stability is poor, also largely influences device lifetime.Thus, it needs
Develop the electroluminescent organic material of efficient stable.
Invention content
The triaromatic amine compound containing fluorenes that the present invention provides a kind of, is the compound for having the following structure Formulas I：
Wherein, Ar1-Ar3Independently selected from the substitution either aryl of unsubstituted C6-C30, substitution or unsubstituted
The carbazyl of the triaromatic amine base of C18-C30, substitution or unsubstituted C12-C30；R1-R10Independently selected from hydrogen, C1-C12
Alkyl, substitution or unsubstituted C6-C30 aryl.
Optionally, the aryl is selected from phenyl, diphenyl, naphthalene, phenyl napthyl, 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, the substitution either dibenzofurans of the dibenzothiophene of unsubstituted C6-C30 and substitution or unsubstituted C6-C30
Base.
Optionally, Ar1Gained group is replaced by the alkyl of C1-C12 selected from phenyl, naphthalene, xenyl and the above group.
Optionally, R1-R10Independently selected from hydrogen, methyl, ethyl, propyl, isopropyl, butyl, tertiary butyl, phenyl.
Optionally, the R1And R2Form spiro structure.
Further alternative, the triaromatic amine compound containing fluorenes specifically includes the compound of following structural 1-50：
The triaromatic amine compound containing fluorenes of the present invention can be reacted by Buchwald-Hartwig and Liv Ullmann it is anti-,
Suzkui should be prepared.
The triaromatic amine compound containing fluorenes of the present invention can be applied to organic electroluminescence device, solar cell, have
Machine thin film transistor (TFT) or organophotoreceptorswith field.
The present invention also provides a kind of organic electroluminescence device, which includes anode, cathode and organic layer, organic layer
Including at least one in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, exciton barrier-layer or electron transfer layer
Layer, which is characterized in that at least one layer of containing such as the above-mentioned triaromatic amine compound containing fluorenes 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.
Preferably, wherein the layer where the triaromatic amine compound containing fluorenes as described in structural formula I is hole transmission layer.
The triaromatic amine compound containing fluorenes as described in structural formula I is used alone, or is used in mixed way with other compounds；Such as
The triaromatic amine compound containing fluorenes described in structural formula I can be used alone one such compound, can also use simultaneously
Two or more compound in structural formula I；A kind of triaromatic amine containing fluorenes selected from structural formula 1-50 is used alone
Compound, or the two or more triaromatic amine compounds containing fluorenes selected from structural formula 1-50 are used simultaneously.
Still optionally further, organic electroluminescence device of the invention include anode, hole injection layer, hole transmission layer,
In luminescent layer, electron transfer layer, electron injecting layer and cathode, wherein luminescent layer or hole transmission layer containing it is a kind of or it is a kind of with
On structural formula I compound；It is further preferred that containing one or more kinds of knots in luminescent layer or hole transmission layer
The compound of structure formula 1-50.
The overall thickness of the organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
The present invention organic electroluminescence device using the present invention have structural formula I compound when, can use take
With other materials, such as hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and barrier layer, 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.In addition to the present invention is with Compounds of structural formula I,
May include other small molecules and macromolecular organic compound, including but not limited to carbazole compound, triaromatic amine compound,
Benzidine compound, compound of fluorene class, phthalocyanine-like compound, six cyano, six miscellaneous triphen
(hexanitrilehexaazatriphenylene), tetra- cyanogen dimethyl-parabenzoquinone (F4- of tetra- fluoro- 7,7' of 2,3,5,6-, 8,8'-
TCNQ), polyvinyl carbazole, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of the organic electroluminescence device of the present invention has the good characteristics of luminescence, can be adjusted according to the needs
The range of visible light.Following compound, including but not limited to naphthalene compounds, pyrene compound, fluorenes class chemical combination can be contained
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, triphenylamine ethylene compounds, aminated compounds, carbazole compound, benzimidazoles compound, furan
Class of muttering compound, metal organic fluorescence complex compound, metal Phosphorescent complex compound (such as Ir, Pt, Os, Cu, Au), polyethylene click
The organic polymer luminescent materials such as azoles, poly-organosilicon compound, polythiophene, they can be used alone, and a variety of can also mix
Object uses.
The triaromatic amine compound containing fluorenes of organic electroluminescence device of the present invention requires good electron-transporting
Can, can be effectively electronics from cathode transport to luminescent layer in, have prodigious electron mobility.It can select or arrange in pairs or groups
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 heterocycle compound, quinolines, phenanthrene
Hello quinoline class compound, metallo-chelate (such as Alq3, 8-hydroxyquinoline lithium), fluorine substituted benzene compound, benzimidazole chemical combination
Object.
Electronics effectively can be injected into organic layer by the electron injecting layer of organic electroluminescence device of the present invention from cathode
In, it is mainly selected from the alkali metal either compound of alkali metal or the compound selected from alkaline-earth metal or alkaline-earth metal or alkali
Metal complex can select following compound, but not limited to this, alkali metal, alkaline-earth metal, rare earth metal, alkali metal
Oxide either 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 can also mixture use, can also be used cooperatively with other electroluminescent organic materials.
Each layer of organic layer in the organic electroluminescence device of the present 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 triaromatic amine compound containing fluorenes of the present invention as described in structural formula I, has preferable thermostabilization
Property, high-luminous-efficiency, high luminance purity.The organic electroluminescence device made of the triaromatic amine compound containing fluorenes has
The advantages of electroluminescent efficiency is good and excitation purity is excellent and long lifespan.
Description of the drawings
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 implementation mode
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 A
In there-necked flask, chlorobenzoyl chloride (30.8g, 0.22mol), dry dichloromethane (250mL) is added, in nitrogen protection
Under, alchlor (35g, 0.26mol) is added at 0 DEG C, then 2- bromo- 9 is added portionwise, 9 dimethyl fluorenes (54.6g, 0.2mol) add
Finish stirring 2 hours, water quenching reaction, organic phase is added to cross silica gel after washing liquid separation, be spin-dried for, crude product ethyl alcohol recrystallization obtains
Off-white powder 57g, yield 76%.
The synthetic method of intermediate B
In flask, addition intermediate A (37.6g, 100mmol), anhydrous tetrahydro furan (400mL), under nitrogen protection
It is cooled to 0 DEG C, is slowly added to 2- xenyl magnesium bromide grignard reagents (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, with dichloromethane extraction, dry, concentration, glacial acetic acid and dense salt is added
Acid is heated to reflux 5 hours, cooling, removing solvent, Jia Shui, is extracted with dichloromethane, dry, concentration, crude by column chromatography is pure
Change obtains product 36g, yield 70%.
The synthetic method of compound 1
In flask, sequentially add intermediate 3-2 (3g, 5.9mmol), two (4- tert-butyl-phenyls) amine (1.6g,
5.9mmol), sodium tert-butoxide (1.2g, 12mmol), palladium (0.1g), X-phos (0.3g), toluene (30mL) are protected in nitrogen
It is heated to reflux under shield 5 hours, it is cooling, solvent is removed, crude by column chromatography purifies to obtain product 3.5g, yield 85%.
The synthetic method of other embodiment such as compound 1, be all use intermediate B as raw material, then with others
Amine reacts, table 1 specific as follows：
1 raw material of table and yield
Embodiment 16-30
The preparation of organic electroluminescence device
OLED is prepared using the compound of embodiment
First, by electrically conducting transparent ito glass substrate 110 (carrying anode 120 above) (the limited public affairs of South China glass group share
Department) it passes through successively：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 are 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 spectrometers measure
100mA/cm2Current density under external quantum efficiency be such as table 2.
Comparative example 1-3
In addition to use HT1, HT2, HT3 replace the compounds of this invention as hole mobile material other than, comparative example prepares device
Method is as embodiment 16-30.
2 test result of table
The structural formula of compound described in device is as follows：
From Table 2, it can be seen that the triaromatic amine compound containing fluorenes of the present invention is used for organic electroluminescence device, it can be with
Operating voltage is reduced, device efficiency is improved, is the hole mobile material with excellent performance.As described above, the chemical combination of the present invention
There is object high stability, the organic electroluminescence device of preparation to have 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 in the protection domain being defined in the patent claims.
Claims (10)
1. a kind of triaromatic amine compound containing fluorenes, which is characterized in that have the following structure the compound of Formulas I：
Wherein, Ar1-Ar3Independently selected from the substitution either aryl of unsubstituted C6-C30, substitution or unsubstituted C18-C30
Triaromatic amine base, substitution or unsubstituted C12-C30 carbazyl；R1-R10Independently selected from hydrogen, C1-C12 alkyl,
The aryl of substitution or unsubstituted C6-C30.
2. the triaromatic amine compound containing fluorenes as described in claim 1, which is characterized in that the aryl is selected from phenyl, hexichol
Base, naphthalene, phenyl napthyl, xenyl, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, acenaphthenyl, acenaphthylene base, (9,9-
Dialkyl group) fluorenyl, (9,9- bis- substitution either unsubstituted aryl) fluorenyl, substitution or unsubstituted C6-C30 dibenzo thiophene
The dibenzofuran group of pheno base and substitution or unsubstituted C6-C30.
3. the triaromatic amine compound containing fluorenes as claimed in claim 2, which is characterized in that Ar1Selected from phenyl, naphthalene, xenyl
And the above group replaces gained group by the alkyl of C1-C12.
4. the triaromatic amine compound containing fluorenes as described in claim 1, which is characterized in that R1-R10Independently selected from hydrogen, first
Base, ethyl, propyl, isopropyl, butyl, tertiary butyl, phenyl.
5. the triaromatic amine compound containing fluorenes as described in claim 1, which is characterized in that the R1And R2Form spiro structure.
6. the triaromatic amine compound containing fluorenes as described in claim 1, which is characterized in that specifically include following structural 1-50
Compound：
7. the application of triaromatic amine compound in organic electroluminescence device described in claim 1 containing fluorenes.
8. 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 or electron transfer layer, which is characterized in that institute
It states at least one layer of containing the triaromatic amine compound containing fluorenes as described in claim 1 in organic layer.
9. organic electroluminescence device as claimed in claim 8, which is characterized in that three containing fluorenes as described in claim 1
Layer where aromatic amine compound is hole transmission layer.
10. organic electroluminescence device as claimed in claim 8, which is characterized in that a kind of be selected from such as right is wanted is used alone
The triaromatic amine compound containing fluorenes of the structural formula 1-50 described in 6 is sought, or simultaneously using two or more selected from such as claim 6 institute
The triaromatic amine compound containing fluorenes of the structural formula 1-50 stated.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810650136.5A CN108752221A (en) | 2018-06-22 | 2018-06-22 | A kind of triaromatic amine compound containing fluorenes and application thereof and luminescent device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810650136.5A CN108752221A (en) | 2018-06-22 | 2018-06-22 | A kind of triaromatic amine compound containing fluorenes and application thereof and luminescent device |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN108752221A true CN108752221A (en) | 2018-11-06 |
Family
ID=63976183
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810650136.5A Pending CN108752221A (en) | 2018-06-22 | 2018-06-22 | A kind of triaromatic amine compound containing fluorenes and application thereof and luminescent device |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108752221A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109535175A (en) * | 2018-11-28 | 2019-03-29 | 上海道亦化工科技有限公司 | A kind of double triaromatic amine compounds, application and the luminescent device of the spiro structure containing five-membered ring |
| CN111138342A (en) * | 2018-11-05 | 2020-05-12 | 乐金显示有限公司 | Novel compound and organic electroluminescent device 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 |
| CN113717058A (en) * | 2021-09-17 | 2021-11-30 | 长春海谱润斯科技股份有限公司 | Triarylamine compound containing fluorene derivative group and organic electroluminescent device thereof |
| CN113788759A (en) * | 2021-09-17 | 2021-12-14 | 长春海谱润斯科技股份有限公司 | Triarylamine compound containing fluorene group and organic electroluminescent device thereof |
| CN116496168A (en) * | 2023-06-29 | 2023-07-28 | 吉林奥来德光电材料股份有限公司 | Light-emitting auxiliary material and organic electroluminescent device |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104037361A (en) * | 2014-06-25 | 2014-09-10 | 上海道亦化工科技有限公司 | Organic electroluminescence device |
| CN107382749A (en) * | 2017-07-28 | 2017-11-24 | 长春海谱润斯科技有限公司 | The aromatic amine analog derivative and its organic luminescent device of a kind of class formation containing fluorenes |
-
2018
- 2018-06-22 CN CN201810650136.5A patent/CN108752221A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104037361A (en) * | 2014-06-25 | 2014-09-10 | 上海道亦化工科技有限公司 | Organic electroluminescence device |
| CN107382749A (en) * | 2017-07-28 | 2017-11-24 | 长春海谱润斯科技有限公司 | The aromatic amine analog derivative and its organic luminescent device of a kind of class formation containing fluorenes |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11545630B2 (en) | 2018-11-05 | 2023-01-03 | Lg Display Co., Ltd. | Compound and organic electroluminescent device comprising the same |
| CN111138342A (en) * | 2018-11-05 | 2020-05-12 | 乐金显示有限公司 | Novel compound and organic electroluminescent device comprising same |
| CN111138342B (en) * | 2018-11-05 | 2023-10-31 | 乐金显示有限公司 | Novel compound and organic electroluminescent device comprising the same |
| CN109535175A (en) * | 2018-11-28 | 2019-03-29 | 上海道亦化工科技有限公司 | A kind of double triaromatic amine compounds, application and the luminescent device of the spiro structure containing five-membered ring |
| US11711978B2 (en) * | 2019-09-16 | 2023-07-25 | 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 |
| EP3792255A1 (en) * | 2019-09-16 | 2021-03-17 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the 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 |
| CN113717058A (en) * | 2021-09-17 | 2021-11-30 | 长春海谱润斯科技股份有限公司 | Triarylamine compound containing fluorene derivative group and organic electroluminescent device thereof |
| CN113788759A (en) * | 2021-09-17 | 2021-12-14 | 长春海谱润斯科技股份有限公司 | Triarylamine compound containing fluorene group and organic electroluminescent device thereof |
| CN113717058B (en) * | 2021-09-17 | 2023-08-15 | 长春海谱润斯科技股份有限公司 | Triarylamine compound containing fluorene derivative group and organic electroluminescent device thereof |
| CN113788759B (en) * | 2021-09-17 | 2024-01-26 | 长春海谱润斯科技股份有限公司 | Triarylamine compound containing fluorene group and organic electroluminescent device thereof |
| CN116496168A (en) * | 2023-06-29 | 2023-07-28 | 吉林奥来德光电材料股份有限公司 | Light-emitting auxiliary material and organic electroluminescent device |
| CN116496168B (en) * | 2023-06-29 | 2023-12-01 | 吉林奥来德光电材料股份有限公司 | Light-emitting auxiliary material and organic electroluminescent device |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108752221A (en) | A kind of triaromatic amine compound containing fluorenes and application thereof and luminescent device | |
| CN109053698A (en) | A kind of aromatic amine compound and luminescent device containing dibenzofurans | |
| CN106831313A (en) | A kind of compound and its organic electroluminescence device with triaryl naphthalene | |
| CN108864013A (en) | A kind of aromatic amine compound containing dibenzofurans and application thereof and luminescent device | |
| CN105175313B (en) | A kind of hole injection compound and its 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 | |
| CN105601612B (en) | Phosphorescence host compound containing indolyl radical and its organic electroluminescence 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 | |
| CN108658953A (en) | A kind of compound based on dibenzofurans and carbazole and application thereof and luminescent device | |
| CN108299388A (en) | A kind of phenanthrene derivatives and application thereof and organic electroluminescence device | |
| CN106883204A (en) | Organic electroluminescent compounds and luminescent device based on benzo [b] naphtho- [1,2 d] furans | |
| CN109535093A (en) | A kind of trisubstituted benzene based compound and organic electroluminescence device | |
| 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 | |
| CN108752317A (en) | One kind is containing anthracene derivant and application thereof and luminescent device | |
| CN106749289B (en) | A kind of organic electroluminescent compounds and its luminescent device with spiro structure | |
| CN107652223A (en) | A kind of carbazoles organic electroluminescent compounds and its organic electroluminescence device | |
| CN108358932A (en) | A kind of nitrogen heterocyclic and application thereof and organic electroluminescence device | |
| CN105669466B (en) | A kind of compound and its organic electroluminescence device based on fluoranthene | |
| CN107586273A (en) | A kind of acenaphthene class 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 | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20181106 |