CN104037340A - Organic electroluminescence device - Google Patents
Organic electroluminescence device Download PDFInfo
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- CN104037340A CN104037340A CN201410293595.4A CN201410293595A CN104037340A CN 104037340 A CN104037340 A CN 104037340A CN 201410293595 A CN201410293595 A CN 201410293595A CN 104037340 A CN104037340 A CN 104037340A
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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
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- 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
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- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- 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
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- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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- 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
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- H—ELECTRICITY
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- 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
Abstract
The invention provides an organic electroluminescence device. The organic electroluminescence device comprises an anode, a cathode and an organic layer; the organic layer comprises one or more of a hole injection layer, a hole transmission layer, a lighting layer, a barrier layer, an electron injection layer and an electron transmission layer. The organic electroluminescence device is characterized in that at least one layer in the organic layer contains a compound as shown in the structural formula (I). Structural formula is as shown in the specification.
Description
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 combined in luminescent layer through hole transmission layer and the electronics that produced by negative electrode through electron transfer layer and forms exciton, 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 the distinct advantages such as flexible and transparent 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 screens such as camera and mobile phones, 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 the electronics of luminescent layer and number of cavities uneven, 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 due to the intrinsic characteristic that self can degrade, take 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 organic electronic transport compound, and it is the compound with following structural formula I:
Wherein, R
1, R
2, R
3, R
4, R
5, R
6, R
7, R
8, R
9, R
10, R
11, R
12respectively independently selected from the alkyl of hydrogen, D-atom, halogen, cyano group, nitro, C1-C12, the replacement of the replacement of the replacement of the replacement of the alkoxyl of C1-C8, C6-C30 or unsubstituted aryl, C3-C30 or unsubstituted heteroaryl, C2-C8 or unsubstituted thiazolinyl, C2-C8 or unsubstituted alkynyl;
L
1and L
2respectively independently selected from the alkyl of sky, singly-bound, C1-C6, the replacement of the replacement of C6-C30 or unsubstituted aryl, C3-C30 or unsubstituted heteroaryl;
X
1, X
2respectively independently selected from O, S, Se, NR
13;
R
13for the alkyl of hydrogen, C1-C12, the replacement of the replacement of C6-C60 or unsubstituted aryl, C3-C60 or unsubstituted heteroaryl;
Wherein preferred mode is:
R
1, R
2, R
3, R
4, R
5, R
6, R
7, R
8, R
9, R
10, R
11, R
12respectively independently selected from the alkyl of hydrogen, halogen, cyano group, nitro, C1-C8, the alkoxyl of C1-C8, 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
1, X
2respectively independently selected from O, S, NR
13;
R
13for
C1-C8 alkyl, 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;
Wherein above-mentioned phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylene base, fluoranthene base, 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
7, R
8, R
9, R
10, R
11, R
12respectively 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
1, X
2respectively independently selected from NR
13;
R
13be selected from methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl, by the alkyl of C1-C4, replaced or unsubstituted following aryl or heteroaryl:
Further preferred, organic electronic transport compound of the present invention is the compound of following structural 1-52:
Organic electronic transport compound of the present invention can prepare by Suzuki coupling reaction, aldehyde radical and amino condensation reaction.
Organic electronic transport compound 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 and electron transfer layer, has at least one deck to contain just like organic electronic transport compound structural formula (I) Suo Shu in wherein said organic layer:
R wherein
1-R
12, 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 organic electronic transport compound place as described in structural formula (I) is one or more layers in electron transfer layer or electron injecting layer;
Wherein the described organic electronic transport compound of structural formula (I) is the compound of structural formula 1-52;
Organic electronic transport compound as described in structural formula I can be used separately, also can use with other compound; Organic electronic transport compound as described in structural formula I can be used 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, hole injection 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 1-52.
Organic electroluminescence device of the present invention, structural formula I compound also can doublely be done 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 when being used 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 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.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.Except of the present invention, have structural formula I compound, 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, 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, the oxide of the oxide of alkali metal, alkaline-earth metal, rare earth metal, alkali-metal oxide or halide, alkaline-earth metal or halide, 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 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.For metal motor, can use vapour deposition method or sputtering method to be prepared.
Experiment shows, the organic electronic transport compound 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 electronic transport compound to make have advantages of the good and colorimetric purity excellence of electroluminescent efficiency and the life-span long.
Accompanying drawing explanation
Fig. 1 is the hydrogen nuclear magnetic spectrogram of compound 15.
Fig. 2 is the hydrogen nuclear magnetic spectrogram of compound 29.
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 more to describe the present invention in detail, especially exemplified by following example, but be not limited to this.
Embodiment 1
Synthesizing of compound 15
Compound 15-1's is synthetic
In there-necked flask, add phenanthrenequione (6.24g, 30mmol), the concentrated sulfuric acid (50ml) slowly adds NBS (11.2g at 0 ℃, 63mmol), react 2 hours, reactant liquor is slowly poured in frozen water, filter, gained solid obtains 5.6g orange solids with methyl-sulfoxide recrystallization, and productive rate is 50%.
1H?NMR(400MHz,CDCl
3,δ):8.25-8.27(d,J＝8.8Hz,2H),8.08-8.09(d,2H),7.95-7.98(dd,J＝8.4Hz,2H).
Compound 15-2's is synthetic
In there-necked flask, add compound 15-1 (3.66g, 10mmol), o-phenylenediamine (1.2g, 11mmol), acetic acid (40m) and ethanol (80ml), add hot reflux 3 hours, and cold filtration obtains 4.2g faint yellow solid, and productive rate is 96%.
1H?NMR(400MHz,CDCl
3,δ):9.53-9.54(d,2H),8.34-8.40(m,4H),7.88-7.93(m,4H).
Compound 15-3 and 15-4's is synthetic
In flask, add N-phenyl-1,2-phenylenediamine (9.2g, 50mmol) and NMP (80ml, 1-METHYLPYRROLIDONE), then add stirring reaction under 4-bromo-benzoyl chloride (10.9g, 50mmol) room temperature to spend the night.Reacted, reactant liquor is poured into water, has a large amount of solids to separate out, filter, THF for filter cake (oxolane) and recrystallizing methanol, resulting white solid (compound 15-3) adds acetic acid (100ml) to add hot reflux 12 hours, has reacted removal of solvent under reduced pressure, add methyl alcohol (50ml), filter, obtain 12g white solid (compound 15-4), productive rate is 69%.Wherein the nuclear-magnetism of 15-4 is:
1H?NMR(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).
Compound 15-5's is synthetic
Under nitrogen protection, in the there-necked flask that compound 15-4 (10.6g, 29mmol) and the oxolane (100mL) that was dried are added, be cooled to-78 ℃.Under agitation with syringe, slowly inject the n-BuLi hexane solution (20mL of 2.5 moles every liter subsequently; 50mmol); and then add triisopropyl borate ester (8.1g; 43mmol); at this temperature, continue to stir 1 hour; then slowly rise to room temperature, under nitrogen protection, stir and spend the night.Reacted, reactant liquor has been poured in the dilute hydrochloric acid solution of 2N, and be extracted with ethyl acetate three times, merged organic phase, used successively salt solution and washing, then use anhydrous sodium sulfate drying.Except desolventizing, crude product obtains 8.3g white solid with ethyl acetate and n-hexane recrystallization, and productive rate is 74%.
1H?NMR(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)。
Synthesizing of compound 15
In single port flask, add compound 15-2 (0.3g, 0.68mmol), compound 15-5 (0.6g, 1.78mmol), oxolane (20ml) and 2M K
2cO
3the aqueous solution (10ml), under nitrogen protection, adds four (triphenyl phosphorus) palladium (10mg; 0.0075mmol); then add hot reflux 5 hours, reacted, cooling; with dichloromethane extraction three times; organic layer anhydrous sodium sulfate drying, organic solvent is removed in rotation, and crude product carries out column chromatography purification; obtain 0.4g yellow solid, productive rate is 72%.
1H?NMR(400MHz,CDCl
3,δ):9.68(s,2H),8.65(d,2H),8.39-8.41(m,2H),8.07-8.09(m,2H),7.80-7.98(m,12H),7.56-7.61(m,6H),7.33-7.41(m,10H).
Embodiment 2
Synthesizing of compound 29
Compound 29-2's is synthetic
In flask, add m-bromobenzoic acid (5.9g, 29mmol) and thionyl chloride (6mL), add hot reflux 2 hours, cooling, unnecessary thionyl chloride is removed in decompression, adds solvent NMP (1-METHYLPYRROLIDONE, 50mL), adjacent amido diphenylamines (5.3g, 29mmol) and triethylamine (5mL), stirring at normal temperature is spent the night, pour in frozen water, filter, oxolane and recrystallizing methanol for filter cake, gained solid adds acetic acid (50mL) to add hot reflux 12 hours, reacted, removal of solvent under reduced pressure, adds 25ml methyl alcohol, filters, obtain 7.2g white solid, productive rate is 71%.
1H?NMR(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).
Compound 29-3's is synthetic
Under nitrogen protection, in the there-necked flask that compound 29-2 (3.8g, 11mmol) and the oxolane (40mL) that was dried are added, be cooled to-78 ℃.Under agitation with syringe, slowly inject subsequently the n-BuLi hexane solution (6.4mL, 16mmol) of 2.5M, and then add triisopropyl borate ester (3g; 16mmol); at this temperature, continue to stir 1 hour, then slowly rise to room temperature, under nitrogen protection, stir and spend the night.Reacted, reactant liquor has been poured in the dilute hydrochloric acid solution of 2N, and be extracted with ethyl acetate three times, merged organic phase, used successively salt solution and washing, then use anhydrous sodium sulfate drying.Except desolventizing, crude product obtains 2.7g white solid with ethyl acetate and n-hexane recrystallization, and productive rate is 78%.
Synthesizing of compound 29
In single port flask, add compound 29-3 (0.31g, 1mmol), compound 15-2 (0.15g, 0.34mmol), and oxolane (20ml) and 2M K
2cO
3the aqueous solution (10ml), under nitrogen protection, adds four (triphenyl phosphorus) palladium (10mg; 0.0075mmol); then add hot reflux 5 hours, reacted, cooling; with dichloromethane extraction three times; organic layer anhydrous sodium sulfate drying, organic solvent is removed in rotation, and crude product carries out column chromatography purification; obtain 0.15g yellow solid, productive rate is 54%.
1H?NMR(400MHz,CDCl
3,δ):9.68(s,2H),8.46-8.48(d,J＝8.8Hz,2H),8.30-8.32(m,2H),8.05(s,2H),7.71-7.90(m,8H),7.24-7.54(m,20H)。
Embodiment 3
The preparation of organic electroluminescence device
Use the compound 15 preparation OLED of embodiment 1
First, by electrically conducting transparent ito glass substrate 110 (above with anode 120) (China Nanbo Group Co) successively warp: 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 15 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.Device architecture is as Fig. 3
Prepared device records at 200mA/cm with Photo Research PR650 spectrometer
2current density under efficiency be 2.2cd/A, Fig. 4 represents 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) successively warp: 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 200mA/cm with Photo Research PR650 spectrometer
2current density under efficiency be 1.5cd/A.
Under identical condition, apply the efficiency of organic electroluminescence device prepared by organic electronic transport compound of the present invention 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
7, R
8, R
9, R
10, R
11, R
12respectively independently selected from the alkyl of hydrogen, D-atom, halogen, cyano group, nitro, C1-C12, the replacement of the replacement of the replacement of the replacement of the alkoxyl of C1-C8, C6-C30 or unsubstituted aryl, C3-C30 or unsubstituted heteroaryl, C2-C8 or unsubstituted thiazolinyl, C2-C8 or unsubstituted alkynyl;
L
1and L
2respectively independently selected from the alkyl of sky, singly-bound, C1-C6, the replacement of the replacement of C6-C30 or unsubstituted aryl, C3-C30 or unsubstituted heteroaryl;
X
1, X
2respectively independently selected from O, S, Se, NR
13;
R wherein
13for the alkyl of hydrogen, C1-C12, the replacement of the replacement of C6-C60 or unsubstituted aryl, C3-C60 or unsubstituted heteroaryl.
2. organic electroluminescence device according to claim 1, is characterized in that
R wherein
1, R
2, R
3, R
4, R
5, R
6, R
7, R
8, R
9, R
10, R
11, R
12respectively independently selected from the alkyl of hydrogen, halogen, cyano group, nitro, C1-C8, the alkoxyl of C1-C8, 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
1, X
2respectively independently selected from O, S, NR
13;
R
13for
C1-C8 alkyl, 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.
3. organic electroluminescence device according to claim 1, is characterized in that
R wherein
1, R
2, R
3, R
4, R
5, R
6, R
7, R
8, R
9, R
10, R
11, R
12respectively 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
1, X
2respectively independently selected from NR
13;
R
13be selected from methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl, by the alkyl of C1-C4, replaced or unsubstituted following aryl or heteroaryl:
。
4. organic electroluminescence device according to claim 1, the compound that it is characterized in that structural formula (I) is the compound of following structural 1-52:
。
5. organic electroluminescence device according to claim 1, one or more layers in electron transfer layer or electron injecting layer of the layer that it is characterized in that the compound place as described in structural formula (I).
6. organic electroluminescence device according to claim 1, is characterized in that the compound as described in structural formula (I) can be used 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 be used 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 1-52.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017177507A1 (en) * | 2016-04-15 | 2017-10-19 | 深圳市华星光电技术有限公司 | Oled display device and manufacturing method therefor |
| CN107827879A (en) * | 2017-09-14 | 2018-03-23 | 上海珂力恩特化学材料有限公司 | A kind of material available for Flexible Displays and preparation method thereof and organic electroluminescence device |
| CN109096210A (en) * | 2018-09-05 | 2018-12-28 | 武汉市晟承宇科技有限公司 | Compound and application for organic electroluminescence device |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1777592A (en) * | 2003-04-18 | 2006-05-24 | 株式会社半导体能源研究所 | Quinoxaline derivatives, and organic semiconductor devices, electroluminescent devices and electronic appliances, made by using the derivatives |
| CN101003516A (en) * | 2006-01-18 | 2007-07-25 | 中国科学院化学研究所 | Dentritic pattern compound, preparation method and application |
| WO2009060757A1 (en) * | 2007-11-08 | 2009-05-14 | Konica Minolta Holdings, Inc. | Organic electroluminescent device, display device and illuminating device |
| CN101687814A (en) * | 2007-03-29 | 2010-03-31 | 巴斯夫欧洲公司 | heterocyclic bridged biphenyls |
| CN103456897A (en) * | 2012-05-30 | 2013-12-18 | 京东方科技集团股份有限公司 | Organic electroluminescence device |
| CN103468243A (en) * | 2012-06-06 | 2013-12-25 | 广东阿格蕾雅光电材料有限公司 | Organic electronic materials and organic electroluminescent device |
| KR20140048028A (en) * | 2012-10-15 | 2014-04-23 | 엘지디스플레이 주식회사 | Organic light emitting device and organic light emitting display device using the same |
-
2014
- 2014-06-25 CN CN201410293595.4A patent/CN104037340B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1777592A (en) * | 2003-04-18 | 2006-05-24 | 株式会社半导体能源研究所 | Quinoxaline derivatives, and organic semiconductor devices, electroluminescent devices and electronic appliances, made by using the derivatives |
| CN101003516A (en) * | 2006-01-18 | 2007-07-25 | 中国科学院化学研究所 | Dentritic pattern compound, preparation method and application |
| CN101687814A (en) * | 2007-03-29 | 2010-03-31 | 巴斯夫欧洲公司 | heterocyclic bridged biphenyls |
| WO2009060757A1 (en) * | 2007-11-08 | 2009-05-14 | Konica Minolta Holdings, Inc. | Organic electroluminescent device, display device and illuminating device |
| CN103456897A (en) * | 2012-05-30 | 2013-12-18 | 京东方科技集团股份有限公司 | Organic electroluminescence device |
| CN103468243A (en) * | 2012-06-06 | 2013-12-25 | 广东阿格蕾雅光电材料有限公司 | Organic electronic materials and organic electroluminescent device |
| KR20140048028A (en) * | 2012-10-15 | 2014-04-23 | 엘지디스플레이 주식회사 | Organic light emitting device and organic light emitting display device using the same |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017177507A1 (en) * | 2016-04-15 | 2017-10-19 | 深圳市华星光电技术有限公司 | Oled display device and manufacturing method therefor |
| CN107827879A (en) * | 2017-09-14 | 2018-03-23 | 上海珂力恩特化学材料有限公司 | A kind of material available for Flexible Displays and preparation method thereof and organic electroluminescence device |
| CN107827879B (en) * | 2017-09-14 | 2021-06-04 | 奥来德(上海)光电材料科技有限公司 | Material for flexible display, preparation method thereof and organic electroluminescent device |
| CN109096210A (en) * | 2018-09-05 | 2018-12-28 | 武汉市晟承宇科技有限公司 | Compound and application for organic electroluminescence device |
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