CN104037338B - A kind of organic electroluminescence device - Google Patents

A kind of organic electroluminescence device Download PDF

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CN104037338B
CN104037338B CN201410293080.4A CN201410293080A CN104037338B CN 104037338 B CN104037338 B CN 104037338B CN 201410293080 A CN201410293080 A CN 201410293080A CN 104037338 B CN104037338 B CN 104037338B
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electroluminescence device
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organic electroluminescence
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CN104037338A (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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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • 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
    • C07D405/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero 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
    • H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
    • 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

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Abstract

The invention provides a kind of organic electroluminescence device, it comprises anode, negative electrode and organic layer, it is one or more layers that organic layer comprises in hole injection layer, hole transmission layer, luminescent layer, barrier layer, electron injecting layer and electron transfer layer, it is characterized in that in organic layer, at least one deck includes the compound of following structural formula (I).

Description

A kind of organic electroluminescence device
Technical field
The present invention relates to field of organic electroluminescence, relate to a kind of organic electroluminescence device specifically.
Background technology
Organic electroluminescence device (OLEDs) is deposit by spin coating or vacuum evaporation the device that one deck organic material is 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 Display Technique, there is self-luminous, wide viewing angle, low 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 floater 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 useful life is short restrict it and apply widely, particularly large screen display.And restrict the performance that one of them key factor is exactly the electroluminescent organic material in organic electroluminescence device.In addition because OLED is when applying voltage-operated, can Joule heat be produced, make organic material 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.
In OLED material, because the speed of most electroluminescent organic material transporting holes is faster than the speed of transmission electronic, easily cause electronics and the number of cavities imbalance of luminescent layer, the efficiency of such device is just lower.Three (oxine) aluminium (Alq 3) since invention, be extensively studied, but it is still very low as its electron mobility of electron transport material, and the intrinsic characteristic that self can degrade, with in the device of electron transfer layer, there will be the situation of voltage drop, simultaneously, due to lower electron mobility, a large amount of holes is made to enter into Alq 3in layer, excessive hole with the form emittance of non-luminescent, and when as electron transport material, due to the characteristic of its green light, application is restricted.Therefore, development stability and have the electron transport material of larger electron mobility, has great value to widely using of organic electroluminescence device.
Summary of the invention
First the present invention provides a kind of electric transmission compound based on benzimidazole, and it is the compound with following structural formula I:
Wherein, R 1, R 2, R 3, R 4, R 5, R 6, R 7and R 8separately be selected from hydrogen, D-atom, halogen, cyano group, nitro, the alkyl of C1-C8, C1-C8 alkoxyl, the replacement of C6-C30 or unsubstituted aryl, the replacement of C3-C30 or unsubstituted heteroaryl, the replacement of C2-C8 or unsubstituted thiazolinyl, the replacement of C2-C8 or unsubstituted alkynyl;
L 1and L 2separately be selected from sky, singly-bound, the alkyl of C1-C6, the substituted or unsubstituted aryl of C6-C30, the replacement of C3-C30 or unsubstituted heteroaryl,
X 1and X 2separately be selected from O, S, Se, NAr 3;
Wherein Ar 1, Ar 2, Ar 3separately be selected from hydrogen, C1-C12 alkyl, the replacement of C6-C60 or unsubstituted aryl, the replacement of C3-C60 or unsubstituted heteroaryl;
Wherein preferred mode is:
R 1, R 2, R 3, R 4, R 5, R 6, R 7and R 8separately be selected from hydrogen, halogen, cyano group, nitro, C1-C8 alkyl, C1-C8 alkoxyl, phenyl, naphthyl, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinoline;
L 1and L 2separately be selected from sky, singly-bound, phenyl, the phenyl replaced by C1-C4 alkyl, naphthyl, the naphthyl that replaced by C1-C4 alkyl;
X 1and X 2separately be selected from O, S, NAr 3;
Ar 1, Ar 2, Ar 3separately be selected from the alkyl of C1-C8, phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylene base, fluoranthene base, (9,9-dialkyl group) fluorenyl, (9,9-bis-replaces or unsubstituted aryl) fluorenyl, 9,9-Spirofluorene-based, dibenzothiophenes base, dibenzofuran group, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinolyl;
Wherein above-mentioned phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylene base, fluoranthene base, (9,9-dialkyl group) fluorenyl, (9,9-bis-replaces or unsubstituted aryl) fluorenyl, 9,9-Spirofluorene-based, dibenzothiophenes base, dibenzofuran group, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinolyl can further replace by the aryl of the alkyl of C1-C4 or C6-C30;
Preferred mode is further:
R 1, R 2, R 3, R 4, R 5, R 6, R 7and R 8separately be selected from hydrogen, fluorine, nitro, methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl, phenyl, naphthyl;
L 1and L 2separately be selected from sky, singly-bound, phenyl, naphthyl;
X 1and X 2be separately NAr 3.
Wherein Ar 1, Ar 2, Ar 3separately be selected from methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl, the substituted or unsubstituted following aryl of C1-C4 alkyl and heteroaryl:
Preferred further, the electric transmission compound based on benzimidazole of the present invention is the compound of following structural 1-46.
Electric transmission compound based on benzimidazole of the present invention can be prepared by Suzuki coupling reaction and aldehyde radical and amido condensation reaction.
Electric transmission compound based on benzimidazole 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, electron injecting layer or electron transfer layer, has one deck at least containing, for example the electric transmission compound based on benzimidazole described in structural formula (I) in wherein said organic layer:
Wherein R 1-R 8, Ar 1-Ar 2, X 1-X 2and L 1-L 2definition as previously mentioned.
Wherein 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 barrier layer;
Or organic layer is luminescent layer, hole transmission layer, electron transfer layer, electron injecting layer and barrier layer;
Or organic layer is luminescent layer, hole transmission layer, electron injecting layer and barrier layer;
The layer at the electric transmission compound place based on benzimidazole wherein as described in structural formula (I) is electron transfer layer or electron injecting layer;
The electric transmission compound based on benzimidazole wherein described in structural formula (I) is the compound of structural formula 1-46;
The electric transmission compound based on benzimidazole as described in structural formula I can be used alone, and also can use with other compound; The electric transmission compound based on benzimidazole 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 wherein containing structural formula (I) in electron transfer layer; Further preferred, the compound in electron transfer layer or electron injecting layer is the compound of structural formula 1-46.
Organic electroluminescence device of the present invention, Compounds of structural formula I also doublely can do electron injecting layer as during electron transfer layer.
The gross thickness of organic electroluminescence device organic layer of the present invention is 1-1000nm, preferred 50-500nm.
Organic electroluminescence device of the present invention is when using the present invention to have the compound of structural formula I, collocation other materials can be used, as hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and exciton barrier-layer etc., and obtain blue light, green glow, gold-tinted, ruddiness or white light.
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.Other Small molecular and macromolecular organic compound can be comprised, include but not limited to carbazole compound, 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'-tetra-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.Can 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), polyvinylcarbazole, poly-organosilicon compound, the organic polymer luminescent materials such as polythiophene, they can be used alone, also can use by multiple mixture.
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 electron mobility.Have except Compounds of structural formula I except of the present invention, following compound can also be selected, but be not limited thereto, oxa-oxazole, thiazole compound, triazole compound, three nitrogen piperazine compounds, triazine compounds, quinoline compounds, phenazine compounds, siliceous heterocycle compound, quinolines, ferrosin compounds, metallo-chelate (as Alq3), fluorine substituted benzene compound, benzimidazoles 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 alkali 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 of alkali metal, alkaline-earth metal, rare earth metal, alkali-metal oxide or halide, alkaline-earth metal or halide, the oxide of rare earth metal or the organic complex of halide, alkali metal or alkaline-earth metal; Be preferably lithium, lithium fluoride, lithia, lithium nitride, oxine lithium, caesium, cesium carbonate, oxine caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, 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 be prepared by modes such as vacuum vapour deposition, molecular beam vapour deposition method, the dip coating being dissolved in solvent, spin-coating method, stick coating method or inkjet printings.Vapour deposition method or sputtering method can be used to be prepared for metal motor.
Device experimental shows, the electric transmission compound based on benzimidazole of the present invention as described in structural formula (I), has better thermal stability, 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 colorimetric purity is excellent and the life-span is long.
Accompanying drawing explanation
Fig. 1 is the hydrogen nuclear magnetic spectrogram of compound 17.
Fig. 2 is the hydrogen nuclear magnetic spectrogram of compound 37.
Fig. 3 is a kind of organic electroluminescence device structural representation of the present invention
Wherein, 110 are represented as glass substrate, and 120 are represented as anode, and 130 are represented as hole transmission layer, and 140 are represented as luminescent layer, and 150 are represented as electron transfer layer, and 160 are represented as electron injecting layer, and 170 are represented as negative electrode.
Fig. 4 is that embodiment 3 is at 20mA/cm 2current density under emission spectrum.
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 17
The synthesis of compound 17-1
In flask, add N-phenyl-1,2-phenylenediamine (9.2g, 50mmol) and NMP (80ml, 1-METHYLPYRROLIDONE), then add 4-bromo-benzoyl chloride (10.9g, 50mmol) stirred at ambient temperature reaction spend the night.React, reactant liquor is poured into water, has a large amount of solid to separate out, filter, filter cake THF (oxolane) and recrystallizing methanol, the white solid that obtains (compound 15-3) adds acetic acid (100ml) and adds hot reflux 12 hours, has reacted, removal of solvent under reduced pressure, add methyl alcohol (50ml), filter, obtain 12g white solid (compound 17-1), productive rate is 69%.Wherein the nuclear-magnetism of 17-1 is:
1HNMR(400MHz,DMSO,δ):7.78-7.81(d,J＝7.6Hz,1H),7.54-7.60(m,5H),7.43-7.46(m,4H),7.26-7.34(m,2H),7.17-7.19(d,J＝7.2Hz,1H).
The synthesis of compound 17-2
Under nitrogen protection, in the there-necked flask that compound 17-1 (10.6g, 29mmol) and dried oxolane (100mL) add ,-78 DEG C are cooled to.N-BuLi hexane solution (the 20mL of 2.5 moles often liter is under agitation slowly injected subsequently with syringe; 50mmol); and then add triisopropyl borate ester (8.1g; 43mmol); continue stirring 1 hour at this temperature; then slowly rise to room temperature, stir under nitrogen protection and spend the night.React, reactant liquor has been poured in the dilute hydrochloric acid solution of 2N, and be extracted with ethyl acetate three times, merged organic phase, use salt solution and washing successively, then use anhydrous sodium sulfate drying.Except desolventizing, crude product ethyl acetate and n-hexane recrystallization obtain 8.3g white solid, and productive rate is 74%. 1HNMR(400MHz,DMSO,δ):8.14(s,2H),7.34-7.82(m,3H),7.43-7.50(m,7H),7.20-7.35(m,3H)。
The synthesis of compound 17-3
In there-necked flask, add phenanthrenequione (6.24g, 30mmol), the concentrated sulfuric acid (50ml), slowly adds NBS (11.2g at 0 DEG C, 63mmol), react 2 hours, reactant liquor is slowly poured in frozen water, filter, filter cake methyl-sulfoxide recrystallization obtains 5.6g orange solids, and productive rate is 50%.
1HNMR(400MHz,CDCl 3,δ):8.25-8.27(d,J＝8.8Hz,2H),8.08-8.09(d,J＝2.4Hz,2H),7.95-7.98(dd,J＝8.4Hz,2H).
The synthesis of compound 17-4
In there-necked flask, add compound 17-3 (1.1g, 3mmol), benzaldehyde (0.36g, 5.4mmol) and ammonium acetate (0.5g, 6.5mmol), acetic acid (20ml), add hot reflux 3 hours, cold filtration obtains 1.5g faint yellow solid, and productive rate is 95%.
1HNMR(400MHz,CDCl 3,δ):9.00,8.45-8.53(m,2H),7.49-7.74(m,9H),7.71-7.33(m,3H),7.19(s,1H)。
The synthesis of compound 17
In single port flask, add compound 17-4 (0.53g, 1mmol), the 2MK of THF and 8ml of compound 17-2 (0.9g, 3mmol), 20ml 2cO 3the aqueous solution; under nitrogen protection, add 10mg tetra-(triphenyl phosphorus) palladium (0.0075mmol), then add hot reflux 5 hours; react; cooling, with dichloromethane extraction three times, organic over anhydrous dried over sodium sulfate; rotate removing organic solvent; crude product carries out column chromatography purification, obtains 0.74g off-white color solid, and productive rate is 81%.
1HNMR(400MHz,CDCl 3,δ):9.10(s,1H),8.72-8.78(m,2H),7.88-7.94(m,5H),7.72-7.77(m,3H),7.55-7.75(m,16H),7.23-7.43(m,15H).
ESI,m/z:[M+H]+：907.4.
Embodiment 2
The synthesis of compound 37
The synthesis of compound 37-1 and 37-2
In flask, add m-bromobenzoic acid (5.9g, 29mmol) with thionyl chloride (6mL), add hot reflux 2 hours, cooling, the thionyl chloride that decompression removing is unnecessary, add solvent NMP (1-METHYLPYRROLIDONE, 50mL), adjacent amido diphenylamines (5.3g, 29mmol) with triethylamine (5mL), stirring at normal temperature is spent the night, pour in frozen water, filter, filter cake oxolane and recrystallizing methanol, gained solid (compound 37-1) adds acetic acid (50mL) and adds hot reflux 12 hours, react, removal of solvent under reduced pressure, add 25ml methyl alcohol, filter, obtain 7.2g white solid, productive rate is 71%. 1HNMR(400MHz,CDCl 3,δ):7.88-7.93(m,2H),7.49-7.58(m,4H),7.29-7.40(m,6H),7.14-7.18(m,1H).
The synthesis of compound 37-3
Under nitrogen protection, in the there-necked flask that compound 37-2 (3.8g, 11mmol) and dried oxolane (40mL) add, but to-78 DEG C.N-BuLi hexane solution (the 6.4mL of 2.5M is under agitation slowly injected subsequently with syringe; 16mmol); and then add triisopropyl borate ester (3g; 16mmol); continue stirring 1 hour at this temperature; then slowly rise to room temperature, stir under nitrogen protection and spend the night.React, reactant liquor has been poured in the dilute hydrochloric acid solution of 2N, and be extracted with ethyl acetate three times, merged organic phase, use salt solution and washing successively, then use anhydrous sodium sulfate drying.Except desolventizing, crude product ethyl acetate and n-hexane recrystallization obtain 2.7g white solid, and productive rate is 77%.
The synthesis of compound 37
In single port flask, add compound 17-2 (0.15g, 0.28mmol), the 2MK of THF and 8ml of compound 37-3 (0.27g, 0.85mmol), 20ml 2cO 3the aqueous solution; under nitrogen protection, add 10mg tetra-(triphenyl phosphorus) palladium (0.0075mmol), then add hot reflux 5 hours; react; cooling, with dichloromethane extraction three times, organic over anhydrous dried over sodium sulfate; rotate removing organic solvent; crude product carries out column chromatography purification, obtains 0.13g off-white color solid, and productive rate is 52%.
1HNMR(400MHz,CDCl 3,δ):8.91(s,1H),8.62-8.68(m,2H),8.01(s,1H),7.86-7.90(m,3H),7.72(s,1H),7.14-7.65(m,34H).
Embodiment 3
The preparation of organic electroluminescence device
The compound of embodiment 1 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 NPB, 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 compound 17 that evaporation 20nm is thick on luminescent layer is as electron transfer layer 150.
Finally, evaporation 1nmLiF is that electron injecting layer 160 and 100nmAl are as device cathodes 170.
Prepared device PhotoResearchPR650 spectrometer records at 300mA/cm 2current density under efficiency be that 2.1cd/A, Fig. 4 represent that the organic electroluminescence device of the present embodiment is at 20mA/cm 2current density under emission spectrum, be green spectral.
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 and deionized water are cleaned, then use 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.
Prepared device PhotoResearchPR650 spectrometer records at 300mA/cm 2current density under efficiency be 1.7cd/A, transmitting green light.
At identical conditions, the efficiency of organic electroluminescence device prepared by organic electroluminescent compounds of the present invention is applied higher than comparative example.As mentioned above, compound of the present invention has high stability, and organic electroluminescence device prepared by the present invention has high efficiency and optical purity.
Structural formula described in device
。

Claims (6)

1. an organic electroluminescence device, it comprises anode, negative electrode and organic layer, it is one or more layers that organic layer comprises in hole injection layer, hole transmission layer, luminescent layer, barrier layer, electron injecting layer and electron transfer layer, it is characterized in that at least comprising electron transfer layer in organic layer, and containing, for example the compound of lower structural formula (I) in electron transfer layer:
Wherein, R 1, R 2, R 3, R 4, R 5, R 6, R 7and R 8separately be selected from hydrogen, methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl;
L 1and L 2separately be selected from singly-bound, phenyl, naphthyl;
Ar 1, Ar 2separately be selected from methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl, C1-C4 alkyl are substituted or unsubstituted
X 1and X 2be separately NAr 3;
Wherein Ar 3be selected from methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl, the substituted or unsubstituted following aryl of C1-C4 alkyl:
2. organic electroluminescence device according to claim 1, wherein the compound of structural formula (I) is the compound of following structural:
3. organic electroluminescence device according to claim 1, is characterized in that the compound only used in transport layer as described in structural formula (I), or the compound as described in structural formula (I) and other compound is used.
4. organic electroluminescence device according to claim 1, the compound that it is characterized in that as described in structural formula (I) is used alone a kind of compound wherein, or uses two or more the compound in structural formula (I) simultaneously.
5. organic electroluminescence device according to claim 1, is characterized in that it comprises anode, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, the compound containing structural formula (I) in electron transfer layer.
6. organic electroluminescence device according to claim 5, is characterized in that the compound in electron transfer layer is the compound of following structural:
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