CN103980211B - A kind of organic electroluminescent compounds - Google Patents

A kind of organic electroluminescent compounds Download PDF

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CN103980211B
CN103980211B CN201410128403.4A CN201410128403A CN103980211B CN 103980211 B CN103980211 B CN 103980211B CN 201410128403 A CN201410128403 A CN 201410128403A CN 103980211 B CN103980211 B CN 103980211B
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compounds
organic electroluminescent
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CN103980211A (en
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黄锦海
苏建华
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Shanghai Taoe Chemical Technology Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—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
    • H10K85/649—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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • 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

Abstract

The invention discloses the organic electroluminescent compounds of a kind of structural formula (I), this compound has better thermostability, high-luminous-efficiency, high luminance purity, may be used for being manufactured with organic electroluminescence devices, be applied to organic solar batteries, OTFT or organophotoreceptorswith field.

Description

A kind of organic electroluminescent compounds
Technical field
The present invention relates to field of organic electroluminescent materials, relate to a kind of organic electroluminescent compounds specifically.
Background technology
Organic electroluminescence device (OLEDs) is steam by spin coating or vacuum the device crossing deposition one deck organic materials and be prepared between two metal electrodes, classical three layers of organic electroluminescence device comprise hole transmission layer, luminescent layer and electron transfer layer.The hole produced by anode is followed through hole transmission layer the electronics produced by negative electrode to be combined in luminescent layer through electron transfer layer and is formed exciton, then luminous.Organic electroluminescence device can regulate by the material changing luminescent layer the light launching various needs as required.
Organic electroluminescence device is as a kind of novel technique of display, there is luminous, wide viewing angle, less energy-consumption, efficiency are high, thin, rich color, fast response time, Applicable temperature scope wide, low driving voltage, flexible and the particular advantages such as transparent display panel and environmental friendliness can be made, can be applied in flat-panel monitor and a new generation's illumination, also can as the backlight of LCD.
Since invention at the bottom of the eighties in 20th century, organic electroluminescence device is industrially applied to some extent, such as the screen such as camera and mobile phone, but current OLED due to efficiency low, the factors such as work-ing life is short restrict it and apply widely, particularly large screen display.And restrict the performance that one of them important factor is exactly the electroluminescent organic material in organic electroluminescence device.In addition because OLED is when applying voltage-operated, can joule heating be produced, make organic materials easily crystallization occur, have impact on life-span and the efficiency of device, therefore, also need the electroluminescent organic material developing stability and high efficiency.
Phenol oxazine derivative has good hole transport performance, and the application on organic electroluminescence device receives much concern.The phenol piperazine compounds obtained with the adjacent luxuriant and rich with fragrance diamine compounds of two aromatic bases and halogenated aryl hydrocarbon preparation greatly increases the preparation of phenol piperazine, has also widened the kind (CN102491950) of compound.At traditional hole-injecting material, as copperphthalocyanine (CuPc), degraded is slow, and preparation power consumption is high, is unfavorable for environment protection, and its meeting absorb light, affects the efficiency of device.And as the original hole mobile material such as NPB, thermostability is poor, also largely affects device lifetime.Thus, the electroluminescent organic material developing efficient stable is needed.
Summary of the invention
The present invention is exactly the defect overcoming compound above, provides a series of and has better thermostability, the hole transport of high hole mobility and good solubility, injecting material.
The invention provides a kind of organic electroluminescent compounds, there is following structural formula (I):
Wherein, R 1-R 4separately be expressed as hydrogen, D atom, halogen, cyano group, nitro, C1-C8 alkyl, C1-C8 alkoxyl group, the replacement of C6-C30 or unsubstituted aryl, the replacement of C3-C30 or unsubstituted heteroaryl, the replacement of C2-C8 or the replacement of unsubstituted allylic alkylation or C2-C8 or unsubstituted alkynes alkyl;
Wherein, Ar 1-Ar 4separately represent the replacement of C6-C60 or unsubstituted aryl, the replacement of C3-C60 or unsubstituted with the triaromatic amine base of one or more heteroatomic heteroaryl, C6-C60 or the replacement of C6-C30 or unsubstituted carbazyl;
N is 1-4.
Further preferably:
R 1-R 4the phenyl being separately expressed as hydrogen, halogen, cyano group, nitro, C1-C8 alkyl, C1-C8 alkoxyl group, the replacement of C2-C8 or unsubstituted allylic alkylation, the replacement of C2-C8 or unsubstituted alkynes alkyl, unsubstituted phenyl or being replaced by C1-C4 alkyl;
Ar 1-Ar 4separately be expressed as:
The phenyl replaced by C1-C4 alkyl or C6-C30 aryl,
The naphthyl replaced by C1-C4 alkyl or C6-C30 aryl,
The carbazyl, anthryl, phenanthryl, pyrenyl, perylene base or the fluoranthene base that are replaced by N-aryl (C6-C30) or C1-C4 alkyl,
(9,9-dialkyl group) fluorenyl,
(9,9-bis-replaces or unsubstituted aryl) fluorenyl,
9,9-is Spirofluorene-based,
Three fragrance (C6-C60) amido,
Replace or unsubstituted dibenzothiophene base,
Replace or unsubstituted dibenzofuran group;
N is preferably 1, and 2.
Preferred mode is further:
R 1-R 4separately be expressed as hydrogen, methoxyl group, fluorine, methyl, ethyl, propyl group, sec.-propyl, the tertiary butyl, normal-butyl, phenyl or naphthyl;
Ar 4be preferably phenyl, naphthyl, fluorenyl, dibenzothiophene base or dibenzofuran group;
Ar 1-Ar 3separately be preferably following groups, these groups can be substituted further:
Preferred further, a kind of organic electroluminescent compounds of the present invention, it is the structural formula of following 1-40:
Organic electroluminescent compounds of the present invention can be prepared by Suzuki coupling and Buchwald-Hartwig reaction.
Organic electroluminescent compounds of the present invention can be applied in organic electroluminescence device, organic solar batteries, OTFT or organophotoreceptorswith field.
Present invention also offers a kind of organic electroluminescence device, this device comprises anode, negative electrode and organic layer, it is one or more layers that organic layer comprises in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer and electron transfer layer, has one deck at least containing, for example the organic electroluminescent compounds described in structural formula (I) in wherein said organic layer:
Wherein R 1-R 4, Ar 1-Ar 4and the definition of n as previously mentioned;
Wherein organic layer is luminescent layer;
Or organic layer is luminescent layer and hole injection layer;
Or organic layer is luminescent layer and hole transmission layer;
Or organic layer is luminescent layer and electron transfer layer;
Or organic layer is luminescent layer, hole injection layer, hole transmission layer and electron transfer layer;
Or organic layer is luminescent layer, hole injection layer, hole transmission layer, electron transfer layer and electron injecting layer;
Or organic layer is luminescent layer, hole injection layer, hole transmission layer, electron transfer layer, electron injecting layer and blocking layer;
Or organic layer is luminescent layer, hole transmission layer, electron transfer layer, electron injecting layer and blocking layer;
Or organic layer is luminescent layer, hole transmission layer, electron injecting layer and blocking layer;
The layer at the organic electroluminescent compounds place wherein as described in structural formula (I) is luminescent layer, hole transmission layer or hole injection layer;
Organic electroluminescent compounds wherein as described in structural formula (I) is above-claimed cpd 1-40.
Organic electroluminescent compounds as described in structural formula I can be used alone, and also can use with other compound; Organic electroluminescent compounds as described in structural formula I can be used alone a kind of compound wherein, also can use two or more the compound in structural formula I simultaneously.
Organic electroluminescence device of the present invention, preferred mode is further, this organic electroluminescence device comprises anode, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, the compound containing structural formula (I) in its hole-transporting layer; Preferred further, the compound in hole transmission layer is the compound of structural formula 1-40.
When Compounds of structural formula I is as luminescent layer, can as non-impurity-doped luminescent layer or doping luminescent layer.
Described doping luminescent layer comprises material of main part and guest materials, and when structural formula (I) compound is as material of main part, its concentration is the 20-99.9% of whole luminescent layer weight, and preferred 80-99%, is more preferably 90-99%.When structural formula (I) compound is as guest materials, its concentration is the 0.01-80% of this luminescent layer weight, and preferred 1-20%, is more preferably 1-10%.
Two of structural formula I compounds can be used to make material of main part and guest materials respectively simultaneously.
The total thickness of organic electroluminescence device organic layer of the present invention is 1-1000nm, preferred 50-500nm.
The hole transmission layer of organic electroluminescence device of the present invention and hole injection layer, material requested has good hole transport performance, can effectively hole be transferred to luminescent layer from anode.Have except structural formula (I) described compound except above-mentioned, other small molecules and macromolecular organic compound can also be comprised, include but not limited to triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanine-like compound, six cyano group six mix triphen (hexanitrilehexaazatriphenylene), 2,3,5,6-tetra-fluoro-7,7 ', 8,8 '-four cyanogen dimethyl-parabenzoquinone (F4-TCNQ), Polyvinyl carbazole, Polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of organic electroluminescence device of the present invention, has the good characteristics of luminescence, can regulate the scope of visible ray as required.Except containing except phenol piperazine compounds of the present invention, can also containing, for example lower compound, include, but are not limited to naphthalene compounds, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance compounds, bend compounds, fluoranthene compounds, anthracene compounds, pentacene compounds, perylene compounds, two aromatic ethylene compounds, triphenylamine ethylene compounds, aminated compounds, carbazole compound, benzimidazoles compound, furfuran compound, metal organic fluorescence complex compound, metal Phosphorescent complex compound is (as Ir, Pt, Os, Cu), polyvinyl carbazole, poly organic silicon compound, the organic polymer luminescent materials such as Polythiophene, they can be used alone, also can use by multiple mixture.The thickness of luminescent layer is preferably 10-50nm.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires to have good electronic transmission performance, effectively during electronics is from cathode transport to luminescent layer, can have very large electronic mobility.Following compound can be selected, but be not limited thereto, oxa-oxazole, thiazole compound, triazole compound, three nitrogen piperazine compounds, triazine compounds, quinoline compounds, phenazine compounds, siliceous heterocyclic compound, quinolines, phenanthroline compounds, metallo-chelate (as Alq3), fluorine substituted benzene compound.
The electron injecting layer of organic electroluminescence device of the present invention, can effectively electronics be injected into organic layer from negative electrode, mainly be selected from basic metal or alkali-metal compound, or be selected from compound or the alkali metal complex of alkaline-earth metal or alkaline-earth metal, following compound can be selected, but be not limited thereto, the oxide compound of basic metal, alkaline-earth metal, rare earth metal, alkali gold brush or halogenide, the oxide compound of alkaline-earth metal or halogenide, the oxide compound of rare earth metal or the organic complex of halogenide, basic metal or alkaline-earth metal; Be preferably lithium, lithium fluoride, Lithium Oxide 98min, lithium nitride, oxine lithium, caesium, cesium carbonate, oxine caesium, calcium, Calcium Fluoride (Fluorspan), calcium oxide, magnesium, magnesium fluoride, magnesiumcarbonate, magnesium oxide, these compounds can be used alone also can mixture use, also can with other electroluminescent organic materials with the use of.
Every one deck of organic layer in organic electroluminescence device of the present invention, can cross the modes such as method, molecular beam vapour deposition method, the dip coating being dissolved in solvent, spin-coating method, stick coating method or spray ink Printing by vacuum steaming and prepare.Vapour deposition method or sputtering method can be used to be prepared for metal motor.
Device experimental shows, the organic electroluminescent compounds of the present invention as described in structural formula (I), has better thermostability, high-luminous-efficiency, high luminance purity.The organic electroluminescence device adopting this organic electroluminescent compounds to make has the advantage that electroluminescent efficiency is good and purity of color is excellent and the life-span is long.
Accompanying drawing explanation
Fig. 1 is the nuclear magnetic spectrogram of compound 1.
Fig. 2 is the nuclear magnetic spectrogram of compound 3.
Fig. 3 is the nuclear magnetic spectrogram of compound 20.
Fig. 4 is the nuclear magnetic spectrogram of compound 26.
Fig. 5 is the structural representation of the electroluminescent device built in embodiment 5, embodiment 6 and comparative example 1,110 are represented as glass substrate, 120 are represented as anode, 130 are represented as hole transmission layer, 140 are represented as luminescent layer, 150 are represented as electron transfer layer, and 160 are represented as electron injecting layer, and 170 are represented as negative electrode.
Embodiment
In order to more describe the present invention in detail, especially exemplified by following example, but be not limited thereto.
Embodiment 1
The synthesis of compound 1
The synthesis of intermediate brominated phenol piperazine
Brominated phenol piperazine
N9 is added respectively, luxuriant and rich with fragrance-9,10-diamines (15g) of N10-phenylbenzene and to bromo-iodobenzene (11.77g) in flask, and Cu (OTf) 2(2.52g), K 2cO 3(7.68g, 55.6mol), adds trichlorobenzene (50g) subsequently, is heated to about 210 DEG C backflows under mechanical stirring and spends the night, and stops heating after reacting completely, and underpressure distillation is except desolventizing.The faint yellow solid of 4.02g is obtained, productive rate 18.74% by silica gel column chromatography.
The synthesis of compound 1
Compound 1
In flask, by 4.5mgPd (OAc) 2with 5.8mgP (t-Bu) 3hBF 4be dissolved in 20ml toluene, N 20.5g4-bromine azophenlyene is added successively, pentanoic (0.3g) and 0.224g potassium tert.-butoxide, heated overnight at reflux in toluene under protection.After reacting completely, stop heating.Filter, washing, filtrate is revolved and is steamed except desolventizing, adopts silica gel column chromatography to be separated and obtains 410mg white solid, productive rate 68%.
1HNMR (400MHz, CDCl 3) δ 8.76 (d, 2H), 8.30 (d, 1H), 8.20 (d, 1H), 7.82-7.56 (m, 6H), 7.37 (m, 2H), 7.16 (m, 4H), 7.07 (m, 2H), 6.96-6.85 (m, 11H), 6.76 (d, 2H). nuclear-magnetism is shown in Fig. 1.
ESI, m/z:[M+H] +calcdforC 44h 31n 3, theoretical value: 602.2596; Measured value: 602.2596.
Embodiment 2
The synthesis of compound 3
Compound 3
In flask, by 4.5mgPd (OAc) 2with 5.8mgP (t-Bu) 3hBF 4be dissolved in 20ml toluene, N 24-bromine azophenlyene (0.5g) is added successively, N-phenyl-1-naphthylamine (0.4g) and potassium tert.-butoxide (0.22g), heated overnight at reflux in toluene under protection.After reacting completely, stop heating.Filter, washing, filtrate is revolved and is steamed except desolventizing, adopts silica gel column chromatography to be separated and obtains 210mg white solid, productive rate 31%.
1HNMR (400MHz, CDCl3) δ 8.70 (d, 2H), 8.17 (m, 2H), 7.83-7.77 (m, 2H), 7.74-7.51 (m, 7H), 7.42-7.34 (m, 2H), 7.28 (d, 2H), 7.24 (s, 1H), 7.13 (d, 1H), 7.08-6.99 (m, 4H), 6.92 (d, 2H), 6.78 (m, 8H). nuclear-magnetism is shown in Fig. 2.
ESI, m/z:[M+H] +calcdforC 48h 34n 3, theoretical value: 652.2753; Measured value: 652.2750.
Embodiment 3
The synthesis of compound 20
Compound 20
To in flask, add 4-bromine azophenlyene (0.5g) successively, 4-triphenylamine boric acid (0.3g), THF (20ml), tetrakis triphenylphosphine palladium (100mg), wet chemical (2mol/l, 5mL); And spend the night with nitrogen protection heating reflux reaction.Stopped reaction, revolves and steams removing THF (tetrahydrofuran (THF)), with dichloromethane extraction three times, merges organic phase, then is washed to neutrality; Separate organic phase, add anhydrous magnesium sulfate drying, suction filtration, be spin-dried for; White solid 440mg is obtained, productive rate 65% by silica gel column chromatography.
1hNMR (400MHz, CDCl 3) δ 8.74 (d, 2H), 8.13 (m, 2H), 7.62 (m, 6H), 7.33 (d, 2H), 7.30 (d, 2H), 7.22 (m, 6H), 7.14-6.94 (m, 15H), 6.78 (s, 1H). nuclear-magnetism is shown in Fig. 3.
ESI, m/z:[M+H] +calcdforC 50h 36n 3, theoretical value: 678.2909; Measured value: 678.2969.
Embodiment 4
The synthesis of compound 26
The synthesis of intermediate 1
Intermediate 1
40mL dimethylbenzene is added successively to flask; to bromo-iodobenzene (12.86g); start stirring and dissolving; then N-(1-naphthyl) aniline (10g) is added; potassium hydroxide (5.1g), 1; 10-phenanthroline (1.8g); add cuprous iodide (1.74g), nitrogen protection, heating reflux reaction 6h; be down to room temperature; reaction solution filters, and removes solvent under reduced pressure, has been threaded to when a large amount of solid is separated out and has added 50ml sherwood oil; suction filtration, obtaining look solid 8.9g is intermediate 1.
The synthesis of intermediate 2
In flask; 2g intermediate 1 is dissolved in the heavy steamed tetrahydrofuran solution of 20mL; under argon shield; be cooled to-78 DEG C; slow dropping 3.9mln-BuLi hexane solution (2.5M), stirs 1h, then slowly injects 4.3mL triisopropyl borate ester; maintain this temperature to continue to stir 1h; then rise to room temperature, stirring is spent the night, and reaction solution is poured into water; regulate PH to neutral with 2mol/L hydrochloric acid; be extracted with ethyl acetate three times, merge organic layer, with anhydrous sodium sulfate drying; removal of solvent under reduced pressure, obtains 1.2g white solid.
The synthesis of compound 26
Compound 26
To in flask, add 4-bromine azophenlyene (0.5g) successively, intermediate 2 (0.4g), THF solution (30ml), opens and stirs, then add tetrakis triphenylphosphine palladium (50mg), wet chemical (2mol/l, 5mL); Nitrogen protection heating reflux reaction spends the night.Stopped reaction, revolves and steams removing THF, with dichloromethane extraction three times, merges organic phase, then is washed to neutrality; Separate organic phase, add anhydrous magnesium sulfate drying, suction filtration, be spin-dried for; White solid 570mg is obtained, productive rate 78.4% by silica gel column chromatography.
1hNMR (400MHz, CDCl3) δ 8.77 (d, 2H), 8.18-8.11 (m, 2H), 7.91 (m, 2H), 7.78 (m, 3H), 7.67 (m, 2H), 7.60-7.54 (m, 2H), 7.50-7.43 (m, 2H), 7.39-7.31 (m, 4H), 7.29 (d, 2H), 7.27 (s, 2H), 7.25-7.17 (m, 4H), 7.09-6.97 (m, 10H), 6.94 (m, 1H), 6.80 (m, 1H). nuclear-magnetism is shown in Fig. 4.
ESI, m/z:[M+H] +calcdforC 54h 38n 3, theoretical value is: 728.3066; Measured value: 728.3063.
Embodiment 5
The preparation of organic electroluminescence device
Organic electroluminescent compounds of the present invention is used to prepare OLED
First, by electrically conducting transparent ito glass substrate 110 (above with anode 120) (China Nanbo Group Co) warp successively: deionized water, ethanol, acetone and deionized water are cleaned, then use oxygen plasma treatment 30 seconds.
Then, evaporation compound 1, forms the hole transmission layer 130 that 60nm is thick.
Then, the compd A lq that evaporation 30nm is thick on hole transmission layer 3as luminescent layer 140.
Then, the Alq that evaporation 20nm is thick on luminescent layer 3as electron transfer layer 150.
Finally, evaporation 1nmLiF is that electron injecting layer 160 and 100nmAl are as device cathodes 170.
Fig. 5 is shown in by concrete structure schematic diagram.
Prepared device PhotoResearchPR650 spectrograph records at 10mA/cm 2current density under efficiency be 0.22cd/A, transmitting green light.
Wherein, Alq used 3structural formula be:
Embodiment 6
First, by electrically conducting transparent ito glass substrate 110 (above with anode 120) (China Nanbo Group Co) warp successively: deionized water, ethanol, acetone, deionized water is cleaned, then uses oxygen plasma treatment 30 seconds.
Then, evaporation compound 22, forms the hole transmission layer 130 that 60nm is thick.
Then, the compd A lq that evaporation 30nm is thick on hole transmission layer 3as luminescent layer 140.
Then, the Alq that evaporation 20nm is thick on luminescent layer 3as electron transfer layer 150.
Finally, evaporation 1nmLiF is that electron injecting layer 160 and 100nmAl are as device cathodes 170.
Fig. 5 is shown in by concrete structure schematic diagram.
Prepared device PhotoResearchPR650 spectrograph records at 10mA/cm 2current density under efficiency be 0.21cd/A, transmitting green light.
Comparative example 1
First, by electrically conducting transparent ito glass substrate 110 (above with anode 120) (China Nanbo Group Co) warp successively: deionized water, ethanol, acetone, deionized water is cleaned, then uses oxygen plasma treatment 30 seconds.
Then, evaporation NPB, forms the hole transmission layer 130 that 60nm is thick.
Then, the Alq that evaporation 30nm is thick on hole transmission layer 3as luminescent layer 140.
Then, the Alq that evaporation 20nm is thick on luminescent layer 3as electron transfer layer 150.
Finally, evaporation 1nmLiF is that electron injecting layer 160 and 100nmAl are as device cathodes 170.
Fig. 5 is shown in by concrete structure schematic diagram.
Prepared device PhotoResearchPR650 spectrograph records at 10mA/cm 2current density under efficiency be 0.16cd/A, transmitting green light.
NPB wherein used in comparative example 1 is following structural formula:
At identical conditions, the efficiency of the organic electroluminescence device of embodiment 5 and 6 preparation is apparently higher than comparative example 1.Therefore organic electroluminescent compounds of the present invention has high stability, and organic electroluminescence device has high efficiency and optical purity.

Claims (3)

1. an organic electroluminescent compounds, has following structural formula (I):
Wherein, R 1-R 4separately be expressed as hydrogen, methyl, ethyl, propyl group, sec.-propyl, the tertiary butyl, normal-butyl;
Wherein, Ar 4for phenyl;
Ar 1-Ar 3be separately following groups, these groups can be replaced by the alkyl of C1-C4 further:
N is 1 or 2.
2. organic electroluminescent compounds according to claim 1, is characterized in that this compound is following structural formula
3. the application of organic electroluminescent compounds described in claim 1 or 2, it is for the preparation of organic electroluminescence device.
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102491950A (en) * 2011-12-09 2012-06-13 华东理工大学 Quinoxaline derivative and preparation method thereof
KR20130084825A (en) * 2012-01-18 2013-07-26 (주)위델소재 Asymmetric aryl amine structure of the blue light-emitting material containing meta-substituted phenyl and organic electroluminescent device using the its derivatives

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102491950A (en) * 2011-12-09 2012-06-13 华东理工大学 Quinoxaline derivative and preparation method thereof
KR20130084825A (en) * 2012-01-18 2013-07-26 (주)위델소재 Asymmetric aryl amine structure of the blue light-emitting material containing meta-substituted phenyl and organic electroluminescent device using the its derivatives

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