CN104167498A - Organic light-emitting device - Google Patents

Organic light-emitting device Download PDF

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CN104167498A
CN104167498A CN201410414995.6A CN201410414995A CN104167498A CN 104167498 A CN104167498 A CN 104167498A CN 201410414995 A CN201410414995 A CN 201410414995A CN 104167498 A CN104167498 A CN 104167498A
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layer
compound
electroluminescence device
structural formula
organic electroluminescence
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CN104167498B (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
    • 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
    • H10K50/00—Organic light-emitting devices

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  • Engineering & Computer Science (AREA)
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Abstract

The invention provides an organic light-emitting device. The organic light-emitting device comprises an anode, a cathode and an organic layer, wherein the organic layer comprises one or more of a hole injection layer, a hole transmission layer, a light emitting layer, a barrier layer, an electron injection layer and an electron transmission layer. The organic light-emitting device is characterized in that at least one layer in the organic layer comprises a compound with the following structural formula (see the instructions).

Description

A kind of organic electroluminescence device
Technical field
The present invention relates to organic electroluminescent field, relate to specifically a kind of organic electroluminescence device.
Background technology
The device of organic electroluminescence device (OLEDs) for being prepared from by spin coating or vacuum evaporation deposition one deck organic material between two metal electrodes, three layers of classical organic electroluminescence device comprise hole transmission layer, luminescent layer and electron transfer layer.The hole being produced by anode is followed the electronics being produced by negative electrode to be combined in luminescent layer through electron transfer layer and is formed exciton through hole transmission layer, then luminous.Organic electroluminescence device can regulate the light of the various needs of transmitting as required by changing the material of luminescent layer.
Organic electroluminescence device is as a kind of novel Display Technique, have that self-luminous, wide visual angle, low energy consumption, efficiency are high, thin, rich color, fast response time, Applicable temperature scope are wide, low driving voltage, can make flexible and the transparent particular advantages such as display floater and environmental friendliness, can be applied in flat-panel monitor and a new generation's illumination above, also can be used as the backlight of LCD.
Since invention at the bottom of the eighties in 20th century, organic electroluminescence device is industrially application to some extent, and such as the screen such as camera and mobile phone, but current OLED device is because efficiency is 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.Because OLED device is applying voltage-operated time, can produce Joule heat in addition, make organic material that crystallization easily occur, affect life-span and the efficiency of device, therefore, also need to develop the electroluminescent organic material of 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 device is just lower like this.Three (oxine) aluminium (Alq 3) since invention, be extensively studied, but still very low as its electron mobility of electron transport material, and the intrinsic characteristic that self can degrade, taking in the device of electron transfer layer, there will be the situation of voltage drop, simultaneously, due to lower electron mobility, make a large amount of holes enter into Alq 3in layer, excessive hole is with non-luminous form emittance, and when as electron transport material, due to the characteristic of its green light, in application, is restricted.Therefore, development stability and have the electron transport material of larger electron mobility, has great value to being widely used 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 8respectively independently selected from replacement or the unsubstituted alkynyl of the replacement of the replacement of the replacement of the alkyl of hydrogen, D-atom, halogen, cyano group, nitro, C1-C8, C1-C8 alkoxyl, C6-C30 or unsubstituted aryl, C3-C30 or unsubstituted heteroaryl, C2-C8 or unsubstituted thiazolinyl, C2-C8;
L 1and L 2respectively independently selected from replacement or the unsubstituted heteroaryl of the replacement of the alkyl of sky, singly-bound, C1-C6, C6-C30 or unsubstituted aryl, C3-C30,
X 1and X 2respectively independently selected from O, S, S=O, S (O) 2, Se, NAr;
A is selected from O, S, S=O, S (O) 2, Se;
Wherein Ar is selected from replacement or the unsubstituted heteroaryl of the replacement of hydrogen, C1-C12 alkyl, C6-C60 or unsubstituted aryl, C3-C60;
Wherein preferred mode is:
R 1, R 2, R 3, R 4, R 5, R 6, R 7and R 8respectively independently 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 2respectively independently selected from sky, singly-bound, phenyl, the phenyl being replaced by C1-C4 alkyl, naphthyl, the naphthyl that replaced by C1-C4 alkyl;
X 1and X 2respectively independently selected from O, S, S=O, S (O) 2, NAr;
A is selected from O, S, S=O, S (O) 2;
Ar is selected from alkyl, phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylene base, the fluoranthene base, (9 of C1-C8,9-dialkyl group) fluorenyl, (9,9-bis-replaces or unsubstituted aryl) fluorenyl, 9,9-is 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-is Spirofluorene-based, dibenzothiophenes base, dibenzofuran group, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinolyl can further be replaced by the aryl of the alkyl of C1-C4 or C6-C30;
Further preferred mode is:
R 1, R 2, R 3, R 4, R 5, R 6, R 7and R 8respectively independently selected from hydrogen, fluorine, nitro, methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl, phenyl, naphthyl;
L 1and L 2respectively independently selected from sky, singly-bound, phenyl, naphthyl;
X 1and X 2respectively independently selected from O, S, NAr;
A is selected from O and S;
Wherein Ar is selected from methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl, the replacement of C1-C4 alkyl or unsubstituted following aryl and heteroaryl:
Further preferred, the electric transmission compound based on benzimidazole of the present invention is the compound of following structural 1-70.
Electric transmission compound based on benzimidazole of the present invention can prepare by Suzuki coupling 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.
The present invention also provides a kind of organic electroluminescence device, this device comprises anode, negative electrode and organic layer, organic layer comprises one or more layers in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer or electron transfer layer, has at least one deck to contain just like the electric transmission compound based on benzimidazole structural formula (I) Suo Shu in wherein said organic layer:
Wherein R 1-R 8, Ar, A, 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;
Wherein the layer at the electric transmission compound place based on benzimidazole as described in structural formula (I) is electron transfer layer or electron injecting layer;
Wherein the described electric transmission compound based on benzimidazole of structural formula (I) is the compound of structural formula 1-70;
The electric transmission compound based on benzimidazole as described in structural formula I can use separately, also can use with other compound; The electric transmission compound based on benzimidazole as described in structural formula I can use separately 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, further preferred mode is, this organic electroluminescence device comprises anode, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, the compound that wherein contains structural formula (I) in electron transfer layer or electron injecting layer; Further preferred, the compound in electron transfer layer or electron injecting layer is the compound of structural formula 1-70.
Organic electroluminescence device of the present invention, structural formula I compound also can doublely do electron injecting layer during as electron transfer layer.
The gross thickness of organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
Organic electroluminescence device of the present invention is in the time using the present invention to have the compound of structural formula I, can use collocation other materials, as hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and 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.Can comprise other little molecule and macromolecular organic compounds, include but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanine-like compound, the assorted triphen (hexanitrilehexaazatriphenylene), 2 of six cyano group six, 3,5,6-tetrafluoro-7,7', 8,8'-, tetra-cyanogen dimethyl 1,4-benzoquinone (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 as required the scope of visible ray.Can contain following 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, the organic phosphorescence complex compound of metal is (as Ir, Pt, Os, Cu), polyvinylcarbazole, poly-organosilicon compound, the organic polymer luminescent materials such as polythiophene, they can use separately, 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, can, effectively during electronics is from cathode transport to luminescent layer, have very large electron mobility.Have structural formula I compound except of the present invention, can also select following compound, but be not limited to this, 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, have structural formula I compound except of the present invention, 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, can select following compound, but be not limited to this, alkali metal, alkaline-earth metal, rare earth metal, alkali-metal oxide or halide, the oxide of alkaline-earth metal or halide, the oxide of rare earth metal or halide, the organic complex of 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 use separately also and can use by mixture, also can be used in conjunction with other electroluminescent organic materials.
Every one deck of organic layer in organic electroluminescence device of the present invention, can prepare by modes such as vacuum vapour deposition, molecular beam vapour deposition method, the dip coating that is dissolved in solvent, spin-coating method, excellent painting method or inkjet printings.Can use vapour deposition method or sputtering method 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 that adopts this organic electroluminescent compounds to make have advantages of the good and colorimetric purity excellence of electroluminescent efficiency and the life-span long.
Brief description of the drawings
Fig. 1 is the hydrogen nuclear magnetic spectrogram of compound 31.
Fig. 2 is the hydrogen nuclear magnetic spectrogram of compound 51.
Fig. 3 is that compound 31 and compound 51 are 1 × 10 in concentration -5the uv-visible absorption spectra recording with Varian Cary 500 ultraviolet-visible spectrophotometers under the dichloromethane solution of mole every liter.
Fig. 4 is that compound 31 and compound 51 are 1 × 10 in concentration -5the fluorescence emission spectrum recording with Varian Cary Eclipse sepectrophotofluorometer under the dichloromethane solution of mole every liter.
Fig. 5 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. 6 is that embodiment 3 is at 25mA/cm 2current density under emission spectrum.
Embodiment
In order more to describe the present invention in detail, especially exemplified by following example, but be not limited to this.
Embodiment 1
Synthesizing of compound 31
Intermediate 31-1's is synthetic
In flask, add the acetic acid of thioxanthones (5.0g, 24mmol) and 45ml, add hot reflux, slowly drip bromine (9.6g, 60mmol), drip off, add hot reflux 12 hours, cooling, filter, obtain 6.2g yellow solid, productive rate is 70%. 1H?NMR(400MHz,CDCl 3,δ):8.74(s,2H),7.73-7.75(d,J＝8.4Hz,2H),7.46-7.48(d,J＝8.4Hz,2H).
Intermediate 31-2 and intermediate 31-3's is synthetic
In there-necked flask, add magnesium chips (0.32g, 13.5mmol), add the iodine of catalytic amount, slowly drip 15ml oxolane (THF) solution that is dissolved with 2-bromo biphenyl (3g, 13.5mmol), add hot reflux 2 hours, cooling, the liquid of gained is slowly added drop-wise to the 30ml tetrahydrofuran solution that is dissolved with intermediate 31-1 (2.5g, 6.8mmol), dropwise, reflux 6 hours, cooling, reactant liquor is poured into water, be extracted with ethyl acetate three times, merge organic phase, dry, the concentrated intermediate 31-2 that obtains.The acetic acid that adds 30ml toward the intermediate 31-2 of gained, adds hot reflux, drips the concentrated hydrochloric acid of 0.5ml, refluxes 2 hours, cooling, filters and obtains 2.4g white solid, and productive rate is 71%. 1H?NMR(400MHz,CDCl 3,δ):7.79-7.81(d,J＝7.6Hz,2H),7.52-7.54(d,J＝7.6Hz,2H),7.41-7.45(m,2H),7.23-7.26(m,6H),6.60(s,2H).
Synthesizing of compound 31
In single port flask, add compound 31-3 (0.25g, 0.5mmol), 4-(1-phenyl-1H-benzimidazolyl-2 radicals-yl) phenyl boric acid (0.4g, 1.24mmol), the 2M K of the THF of 20ml and 8ml 2cO 3the aqueous solution; under nitrogen protection, add 10mg tetra-(triphenyl phosphorus) palladium (0.0075mmol), then add hot reflux 5 hours; react; cooling, use dichloromethane extraction three times, organic layer anhydrous sodium sulfate drying; organic solvent is removed in rotation; crude product carries out column chromatography purification, obtains 0.42g off-white color solid, and productive rate is 95%. 1H?NMR(400MHz,CDCl 3,δ):7.85-7.87(d,J＝8.0Hz,2H),7.77-7.79(d,J＝7.6Hz,2H),7.63-7.64(d,J＝7.6Hz,2H),7.20-7.48(m,28H),7.13-7.15(d,J＝8.0Hz,4H),6.75(s,2H).
The hydrogen nuclear magnetic spectrogram of compound 31 is shown in Fig. 1.Compound 31 is 1 × 10 in concentration -5under the dichloromethane solution of mole every liter, be 350nm with the maximum absorption wavelength that Varian Cary 500 ultraviolet-visible spectrophotometers record, uv-visible absorption spectra is shown in Fig. 3, and Fig. 4 is that compound 31 is 1 × 10 in concentration -5the fluorescence emission spectrum recording with Varian Cary Eclipse sepectrophotofluorometer under the dichloromethane solution of mole every liter, the maximum emission wavelength recording is 410nm.
Embodiment 2
Synthesizing of compound 51
In single port flask, add compound 31-3 (0.25g, 0.5mmol), 3-(1-phenyl-1H-benzimidazolyl-2 radicals-yl) phenyl boric acid (0.4g, 1.24mmol), the 2M K of the THF of 20ml and 8ml 2cO 3the aqueous solution; under nitrogen protection, add 10mg tetra-(triphenyl phosphorus) palladium (0.0075mmol), then add hot reflux 5 hours; react; cooling, use dichloromethane extraction three times, organic layer anhydrous sodium sulfate drying; organic solvent is removed in rotation; crude product carries out column chromatography purification, obtains 0.31g off-white color solid, and productive rate is 70%. 1H?NMR(400MHz,CDCl 3,δ):7.86-7.88(d,J＝7.6Hz,2H),7.77-7.79(d,J＝7.6Hz,2H),7.60-7.62(d,J＝7.6Hz,2H),7.16-7.51(m,28H),7.07-7.10(m,4H),6.70(s,2H).
The hydrogen nuclear magnetic spectrogram of compound 51 is shown in Fig. 2.Compound 51 is 1 × 10 in concentration -5under the dichloromethane solution of mole every liter, be 330nm with the maximum absorption wavelength that Varian Cary 500 ultraviolet-visible spectrophotometers record, uv-visible absorption spectra is shown in Fig. 3, and Fig. 4 is that compound 31 is 1 × 10 in concentration -5the fluorescence emission spectrum recording with Varian Cary Eclipse sepectrophotofluorometer under the dichloromethane solution of mole every liter, the maximum emission wavelength recording is 380nm.
Embodiment 3
The preparation of organic electroluminescence device
Use the compound 51 of embodiment 2 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 thick hole transmission layer 130 of 60nm.
Then the compd A lq that, evaporation 30nm is thick on hole transmission layer 3as luminescent layer 140.
Then the compound 51 that, evaporation 20nm is thick on luminescent layer is as electron transfer layer 150.
Finally, evaporation 1nm LiF is that electron injecting layer 160 and 100nm Al are as device cathodes 170.
Prepared device (structural representation is shown in Fig. 5) records at 25mA/cm with Photo Research PR650 spectrometer 2current density under efficiency be 0.5cd/A, the current density under the driving voltage of 8V is 346mA/cm 2, Fig. 6 represents that the organic electroluminescence device of the present embodiment is at 25mA/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 thick hole transmission layer 130 of 60nm.
Then, the thick Alq of evaporation 30nm on hole transmission layer 3as luminescent layer 140.
Then, the thick Alq of evaporation 20nm on luminescent layer 3as electron transfer layer 150.
Finally, evaporation 1nm LiF is that electron injecting layer 160 and 100nm Al are as device cathodes 170.
Prepared device records at 25mA/cm with Photo Research PR650 spectrometer 2current density under efficiency be 0.28cd/A, the current density under the driving voltage of 8V is 168mA/cm 2, transmitting green light.
Under identical condition, apply the efficiency of organic electroluminescence device prepared by the electric transmission compound based on benzimidazole of the present invention and current density 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 (9)

1. an organic electroluminescence device, it comprises anode, negative electrode and organic layer, organic layer comprises one or more layers 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 that one deck at least includes the compound of following structural formula (I):
Wherein, R 1, R 2, R 3, R 4, R 5, R 6, R 7and R 8respectively independently selected from replacement or the unsubstituted alkynyl of the replacement of the replacement of the replacement of the alkyl of hydrogen, D-atom, halogen, cyano group, nitro, C1-C8, C1-C8 alkoxyl, C6-C30 or unsubstituted aryl, C3-C30 or unsubstituted heteroaryl, C2-C8 or unsubstituted thiazolinyl, C2-C8;
L 1and L 2respectively independently selected from replacement or the unsubstituted heteroaryl of the replacement of the alkyl of sky, singly-bound, C1-C6, C6-C30 or unsubstituted aryl, C3-C30,
X 1and X 2respectively independently selected from O, S, S=O, S (O) 2, Se, NAr;
A is selected from O, S, S=O, S (O) 2, Se;
Wherein Ar is selected from replacement or the unsubstituted heteroaryl of the replacement of hydrogen, C1-C12 alkyl, C6-C60 or unsubstituted aryl, C3-C60.
2. organic electroluminescence device according to claim 1, is characterized in that wherein
R 1, R 2, R 3, R 4, R 5, R 6, R 7and R 8respectively independently 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 2respectively independently selected from sky, singly-bound, phenyl, the phenyl being replaced by C1-C4 alkyl, naphthyl, the naphthyl that replaced by C1-C4 alkyl;
X 1and X 2respectively independently selected from O, S, S=O, S (O) 2, NAr;
A is selected from O, S, S=O, S (O) 2;
Ar is selected from alkyl, phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylene base, the fluoranthene base, (9 of C1-C8,9-dialkyl group) fluorenyl, (9,9-bis-replaces or unsubstituted aryl) fluorenyl, 9,9-is 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-is Spirofluorene-based, dibenzothiophenes base, dibenzofuran group, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinolyl can further be replaced by the aryl of the alkyl of C1-C4 or C6-C30.
3. organic electroluminescence device according to claim 1, wherein
R 1, R 2, R 3, R 4, R 5, R 6, R 7and R 8respectively independently selected from hydrogen, fluorine, nitro, methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl, phenyl, naphthyl;
L 1and L 2respectively independently selected from sky, singly-bound, phenyl, naphthyl;
X 1and X 2respectively independently selected from O, S, NAr;
A is selected from O and S;
Wherein Ar is selected from methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl, the replacement of C1-C4 alkyl or unsubstituted following aryl and heteroaryl:
。
4. organic electroluminescence device according to claim 1, wherein the compound of structural formula (I) is the compound of following structural formula 1-70:
。
5. organic electroluminescence device according to claim 1, the layer that it is characterized in that the compound place as described in structural formula (I) is electron transfer layer or electron injecting layer.
6. organic electroluminescence device according to claim 1, is characterized in that the compound as described in structural formula (I) can use separately, also can use with other compound.
7. organic electroluminescence device according to claim 1, it is characterized in that the compound as described in structural formula (I) can use separately a kind of compound wherein, also can use two or more the compound in structural formula (I) simultaneously.
8. organic electroluminescence device according to claim 1, it comprises anode, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, it is characterized in that the compound that contains structural formula (I) in electron transfer layer.
9. organic electroluminescence device according to claim 8, is characterized in that the compound in electron transfer layer is the compound of structural formula 1-70.
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CN105001229A (en) * 2015-07-07 2015-10-28 上海道亦化工科技有限公司 Organic electroluminescent compound with spiro structure and apparatus of organic electroluminescent compound
CN105047830A (en) * 2015-05-29 2015-11-11 上海道亦化工科技有限公司 Organic light-emitting device
CN109180689A (en) * 2018-09-03 2019-01-11 上海道亦化工科技有限公司 A kind of imdazole derivatives and application thereof and organic electroluminescence device
CN109390501A (en) * 2018-09-30 2019-02-26 长春海谱润斯科技有限公司 A kind of organic electroluminescence device

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