CN105503801A - Aromatic amine luminous compound and organic electroluminescence device manufactured through same - Google Patents
Aromatic amine luminous compound and organic electroluminescence device manufactured through same Download PDFInfo
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Abstract
The invention provides an aromatic amine luminous compound. The aromatic amine luminous compound has good heat stability, high luminous efficiency and high luminous purity, and can be used for manufacturing an organic electroluminescence device and applied to the field of organic solar cells or organic thin-film transistors or organic photoreceptors. The invention further provides the organic electroluminescence device which comprises an anode, a cathode and an organic layer. The organic layer comprises one or more of a luminous layer, a hole injection layer, a hole transfer layer, a hole blocking layer, an electron injection layer and an electron transfer layer. At least one layer in the organic layer comprises the compound shown in the structural formula I shown in the description.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, be specifically related to a kind of aromatic amine luminophor and organic electroluminescence device thereof, belong to organic electroluminescence device technique of display field.
Background technology
Organic electroluminescence device (OLEDs) is deposit by spin coating or vacuum evaporation the device that one deck organic materials is prepared between two metal electrodes, and classical three layers of organic electroluminescence device comprise hole transmission layer, luminescent layer and electron transfer layer.The hole produced by anode is followed through hole transmission layer the electronics produced by negative electrode to be combined in luminescent layer through electron transfer layer and is formed exciton, then luminous.Organic electroluminescence device can regulate by the material changing luminescent layer the light launching various needs as required.
Organic electroluminescence device is as a kind of novel technique of display, there is luminous, wide viewing angle, less energy-consumption, efficiency are high, thin, rich color, fast response time, Applicable temperature scope wide, low driving voltage, flexible and the particular advantages such as transparent display panel and environmental friendliness can be made, can be applied in flat-panel monitor and a new generation's illumination, also can as the backlight of LCD.
Since invention at the bottom of the eighties in 20th century, organic electroluminescence device is industrially applied to some extent, such as the screen such as camera and mobile phone, but current OLED due to efficiency low, the factors such as work-ing life is short restrict it and apply widely, particularly large screen display, therefore needs the efficiency improving device.And restrict the performance that one of them important factor is exactly the electroluminescent organic material in organic electroluminescence device.In addition because OLED is when applying voltage-operated, can joule heating be produced, make organic materials easily crystallization occur, have impact on life-span and the efficiency of device, therefore, also need the electroluminescent organic material developing stability and high efficiency.
In the middle of three primary colors (red, blue, green), ruddiness and green light material have achieved very large development recently, also meet the market requirement of panel.For stable and efficient blue light material still seldom, due to the high energy gap of blue light, make the requirement for material higher, again due to stability and the optical purity Problems existing of blue phosphor materials, the blue fluorescent material therefore developing efficient stable is particularly important.
Summary of the invention
First the present invention provides a kind of aromatic amine luminophor, and it is the compound with following structural formula I:
Ar
1-Ar
4separately be selected from C6-C60 to replace or unsubstituted aryl, C3-C60 replacement or unsubstituted heteroaryl, three fragrance (C6-C60) amido, replacement or unsubstituted carbazyl (C6-C30), (9,9-dialkyl group) fluorenyl, (9,9-bis-replaces or unsubstituted aryl) fluorenyl, 9,9-Spirofluorene-based, C6-C60 replaces or unsubstituted dibenzothiophene base, C6-C60 replace or unsubstituted dibenzofuran group;
X is O or S.
Preferably, Ar
1-Ar
4independently selected from phenyl, xenyl, 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, replace or unsubstituted dibenzothiophene base, replacement or unsubstituted dibenzofuran group; Wherein above-mentioned Ar
1-Ar
4can further replace by the alkyl of C1-C8;
Further preferably, described aromatic amine luminophor is the compound of following structural 1-16:
Aromatic amine compounds of the present invention can be prepared by Suzuki linked reaction and Buchwald-Hartwig reaction.
Aromatic amine compounds of the present invention can be applied in organic electroluminescence device, organic solar batteries, OTFT or organophotoreceptorswith field.
Present invention also offers a kind of organic electroluminescence device, this device comprises anode, negative electrode and organic layer, it is one or more layers that organic layer comprises in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer or electron transfer layer, has one deck at least containing, for example the aromatic amine compounds described in structural formula I in wherein said organic layer:
Wherein Ar
1-Ar
4and the definition of X as previously mentioned.
Wherein organic layer is luminescent layer;
Or organic layer is luminescent layer and electron transfer layer;
Or organic layer is luminescent layer, electron transfer layer and electron injecting layer;
Or organic layer is hole transmission layer and luminescent layer;
Or organic layer is hole injection layer, hole transmission layer and luminescent layer;
Or organic layer is hole transmission layer, luminescent layer and electron transfer layer;
Or organic layer is hole injection layer, hole transmission layer, luminescent layer and electron transfer layer;
Or organic layer is hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer;
Or organic layer is hole injection layer, hole transmission layer, blocking layer, luminescent layer, electron transfer layer and electron injecting layer;
Or organic layer is hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and hole blocking layer;
Or organic layer is hole transmission layer, luminescent layer, electron injecting layer and hole blocking layer;
Preferably, the layer at the aromatic amine compounds place as described in structural formula I is luminescent layer;
Preferably, the aromatic amine compounds as described in structural formula I is the compound of structural formula 1-16;
When aromatic amine compounds as described in structural formula I is prepared for luminescent device, can be used alone, also can use with other compound; Aromatic amine compounds as described in structural formula I can be used alone a kind of compound wherein, also can use two or more the compound in structural formula I simultaneously.
Organic electroluminescence device of the present invention, preferred mode is that this organic electroluminescence device comprises anode, hole transmission layer, luminescent layer, electron transfer layer and negative electrode further, the compound wherein containing one or more structural formula I in luminescent layer; Further preferably, the compound containing one or more structural formula 1-16 in luminescent layer.
The compound of structural formula I of the present invention can as the single luminescent layer of non-impurity-doped or doping luminescent layer, and wherein Compounds of structural formula I is as material of main part, and its content is the 20-99.9% of whole luminescent layer weight, and preferred 80-99%, is more preferably 90-99%; During as guest materials, its content is the 0.1-50% of whole luminescent layer, is preferably 0.5%-10%.
The total 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, can to arrange in pairs or groups use other materials, as medium on hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and blocking layer, 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 molecules 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.Have except Compounds of structural formula I except of the present invention, can also containing, for example lower compound, but be not limited thereto, naphthalene compounds, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance compounds, compounds, fluoranthene compounds, anthracene compounds, pentacene compounds, perylene compounds, two aromatic ethylene compounds, triphenylamine ethylene compounds, aminated compounds, benzimidazoles compound, furfuran compound, organic metal chelate complex in the wrong.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires to have good electronic transmission performance, effectively during electronics is from cathode transport to luminescent layer, can have very large electronic mobility.Following compound can be selected, but be not limited thereto: oxa-oxazole, thiazole compound, triazole compound, three nitrogen piperazine compounds, triazine compounds, quinoline compounds, phenazine compounds, siliceous heterocyclic compound, quinolines, phenanthroline compounds, metallo-chelate are (as Alq
3), 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 basic metal or alkali-metal compound, or be selected from compound or the alkali metal complex of alkaline-earth metal or alkaline-earth metal, following compound can be selected, but be not limited thereto: the oxide compound of basic metal, alkaline-earth metal, rare earth metal, alkali-metal oxide compound or halogenide, alkaline-earth metal or halogenide, the oxide compound of rare earth metal or the organic complex of halogenide, basic metal or alkaline-earth metal; Be preferably lithium, lithium fluoride, Lithium Oxide 98min, lithium nitride, oxine lithium, caesium, cesium carbonate, oxine caesium, calcium, Calcium Fluoride (Fluorspan), calcium oxide, magnesium, magnesium fluoride, magnesiumcarbonate, magnesium oxide, these compounds can be used alone also can mixture use, also can with other electroluminescent organic materials with the use of.
Every one deck of organic layer in organic electroluminescence device of the present invention, can 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 spray ink Printings.Vapour deposition method or sputtering method can be used to be prepared for metal motor.
Device experimental shows, the aromatic amine compounds of the present invention as described in structural formula I, has better thermostability, high-luminous-efficiency, high luminance purity.The organic electroluminescence device adopting this aromatic amine compounds to make has the advantage that electroluminescent efficiency is good and purity of color is excellent and the life-span is long.
Accompanying drawing explanation
Fig. 1 is 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 injection layer, 140 hole transmission layers, and 150 are represented as luminescent layer, and 160 are represented as electron transfer layer, and 170 are represented as electron injecting layer, and 180 are represented as negative electrode.
Embodiment
In order to more describe the present invention in detail, especially exemplified by following example, but be not limited thereto.
Embodiment 1
The synthesis of compound 1
The synthesis of intermediate 1-1
In there-necked flask; add 2-methyl-bromobenzoate (21.4g, 0.1mol), 1-naphthalene boronic acids (17g, 0.1mol), salt of wormwood (27g; 0.2mol), tetra-triphenylphosphine palladium (1g), 200ml tetrahydrofuran (THF) and 100ml water; reflux 12 hours under nitrogen protection, cooling, is extracted with ethyl acetate; dry; concentrated, thick product obtains 24.1g through column chromatography purification, productive rate 92%.
The synthesis of intermediate 1-2
In there-necked flask; add intermediate 1-1 (20g, 77mmol) and polyphosphoric acid (200g), be heated to 160 degree under nitrogen protection and react 5 hours; cooling; in heating frozen water, with dichloromethane extraction, dry; concentrated; thick product ethyl alcohol recrystallization, obtains 13g, productive rate 74%.
The synthesis of intermediate 1-3
In there-necked flask, add intermediate 1-2 (12g, 52mmol) and 200ml Glacial acetic acid, be heated to 80 degree, slowly be added dropwise to bromine (16.7g, 104mmol), react 5 hours, cooling, filter, then obtain productive rate 16g with ethyl alcohol recrystallization, productive rate 81%.
The synthesis of intermediate 1-4
In flask; add adjacent bromo-iodobenzene (28g, 0.1mol), 4-diphenylene-oxide boric acid (21g, 0.1mol), salt of wormwood (20.4g; 0.15mol), tetra-triphenylphosphine palladium (0.5g), water (150ml) and tetrahydrofuran (THF) (300ml); reflux 5 hours under nitrogen protection, cooling, with dichloromethane extraction; dry; concentrated, obtain product 21.5g through column chromatography purification, productive rate 57%.
The synthesis of intermediate 1-5
In there-necked flask, add intermediate 1-4 (6.4g, 20mmol) and 100ml anhydrous tetrahydro furan, be cooled to subzero 78 degree, slowly add the hexane solution (8ml of 2.5M n-Butyl Lithium, 20mmol), react 2 hours, slowly add the tetrahydrofuran solution (6.2g that 80ml is dissolved with intermediate 1-3,16mmol), drip off, slowly rise to room temperature, react 2 hours.Add water, with dichloromethane extraction, dry, concentrated, add Glacial acetic acid 100ml and 3ml concentrated hydrochloric acid, reflux 5 hours, except desolventizing, thick product obtains product 3.5g through column chromatography purification, productive rate 36%.
The synthesis of compound 1
In there-necked flask, add intermediate 1-5 (2g, 3.3mmol), pentanoic (1.6g, 9.8mmol), sodium tert-butoxide (1.3g, 13.2mmol), palladium (0.1g), X-phos (0.3g) and toluene 50ml.Reflux 12 hours, cooling, except desolventizing, thick product obtains product 2.0g through column chromatography purification, productive rate 77%.
Embodiment 2
The synthesis of compound 8
Synthetic method follows the synthetic method of 1 of compound the same, except replacing outside pentanoic with 2-anilino-9,9-dimethyl fluorene, and productive rate 70%.
Embodiment 3
The synthesis of compound 9
Intermediate 9-1
Synthetic method follows intermediate 1-4's, except replacing 4-diphenylene-oxide with 4-dibenzothiophene, and productive rate 65%.
The synthesis of intermediate 9-2
Synthetic method follows intermediate 1-5's, except replacing intermediate 1-4 with intermediate 9-1, and productive rate 40%.
The synthesis of compound 9
Synthetic method is the same with the synthesis of compound 1, except replacing intermediate 1-5 with intermediate 9-2, and productive rate 80%.
Embodiment 4
The synthesis of compound 16
Synthetic method is the same with the synthetic method of compound 9, except replacing outside pentanoic with 2-anilino-9,9-dimethyl fluorene, and productive rate 79%.
Embodiment 5
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, on ITO evaporation HIL (60nm) as hole injection layer 130.
Then, evaporation compound N PB, forms the hole transmission layer 140 that 10nm is thick.
Then, the luminescent layer 150 that evaporation 40nm is thick on hole transmission layer.Wherein, MADN is main body luminescent material, and using the compound 1 of 5% weight ratio as doping guest materials.
Then, the Alq that evaporation 20nm is thick on luminescent layer
3as electron transfer layer 160.
Finally, evaporation 1nmLiF is that electron injecting layer 170 and 100nmAl are as device cathodes 180.
Prepared device PhotoResearchPR650 spectrograph records at 10mA/cm
2current density under brightness be 740cd/m
2.Launch blue light.
Embodiment 6
The preparation method of device is the same with embodiment 5, except replacing the compound 1 of embodiment 5 with compound 8.
Prepared device PhotoResearchPR650 spectrograph records at 10mA/cm
2current density under brightness be 815cd/m
2.Launch blue light.
Embodiment 7
The preparation method of device is the same with embodiment 5, except replacing the compound 1 of embodiment 5 with compound 9.
Prepared device PhotoResearchPR650 spectrograph records at 10mA/cm
2current density under brightness be 695cd/m
2.Launch blue light.
Embodiment 8
The preparation method of device is the same with embodiment 5, except replacing the compound 1 of embodiment 5 with compound 16.
Prepared device PhotoResearchPR650 spectrograph records at 10mA/cm
2current density under brightness be 855cd/m
2.Launch blue light.
Comparative example
The preparation method of device is the same with embodiment 5, except replacing the compound 1 of embodiment 5 with compd B D1.
Prepared device PhotoResearchPR650 spectrograph records at 10mA/cm
2current density under brightness be 540cd/m
2.Launch blue light.
Under identical brightness conditions, apply the brightness of organic electroluminescence device prepared by aromatic amine material of the present invention higher than comparative example, as mentioned above, compound of the present invention has high stability, and the organic electroluminescence device of preparation has high efficiency and optical purity.
The structural formula of compound described in device is as follows:
More than describe preferred embodiment of the present invention in detail.Should be appreciated that the ordinary skill of this area just design according to the present invention can make many modifications and variations without the need to creative work.Therefore, all technician in the art, all should by the determined protection domain of claims under this invention's idea on the basis of existing technology by the available technical scheme of logical analysis, reasoning, or a limited experiment.
Claims (10)
1. an aromatic amine luminophor, is characterized in that it is the compound with following structural formula I:
Ar
1-Ar
4separately be selected from C6-C60 to replace or unsubstituted aryl, C3-C60 replacement or unsubstituted heteroaryl, three fragrance (C6-C60) amido, replacement or unsubstituted carbazyl (C6-C30), (9,9-dialkyl group) fluorenyl, (9,9-bis-replaces or unsubstituted aryl) fluorenyl, 9,9-Spirofluorene-based, C6-C60 replaces or unsubstituted dibenzothiophene base, C6-C60 replace or unsubstituted dibenzofuran group;
X is O or S.
2. aromatic amine luminophor according to claim 1, is characterized in that Ar
1-Ar
4independently selected from phenyl, xenyl, 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, replace or unsubstituted dibenzothiophene base, replacement or unsubstituted dibenzofuran group; Or above-mentioned Ar
1-Ar
4further replace by the alkyl of C1-C8.
3. aromatic amine luminophor according to claim 1, is characterized in that it is the compound of following structural 1-16:
4. an organic electroluminescence device, it 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, electron transfer layer, it is characterized in that in organic layer, at least one deck includes aromatic amine compounds as claimed in claim 1.
5. organic electroluminescence device according to claim 4, is characterized in that the layer at the aromatic amine compounds place as described in structural formula I is luminescent layer.
6. organic electroluminescence device according to claim 4, is characterized in that the aromatic amine compounds as described in structural formula I is used alone, or and other compound use.
7. organic electroluminescence device according to claim 4, the aromatic amine compounds 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.
8. organic electroluminescence device according to claim 4, is characterized in that it comprises anode, hole transmission layer, luminescent layer, electron transfer layer and negative electrode, it is characterized in that the compound containing one or more structural formulas I in luminescent layer.
9. organic electroluminescence device according to claim 4, is characterized in that it comprises anode, hole transmission layer, luminescent layer, electron transfer layer and negative electrode, it is characterized in that the compound contained in luminescent layer is the compound of structural formula 1-16.
10. organic electroluminescence device according to claim 4, it is characterized in that the compound of structural formula I is as the single luminescent layer of non-impurity-doped or doping luminescent layer, wherein Compounds of structural formula I is as material of main part, and its content is the 20-99.9% of whole luminescent layer weight.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106893581A (en) * | 2017-02-23 | 2017-06-27 | 南京高光半导体材料有限公司 | Organic electroluminescent compounds, organic electroluminescence device and its application |
| CN108658789A (en) * | 2018-05-16 | 2018-10-16 | 上海道亦化工科技有限公司 | A kind of triaromatic amine compound containing fluorenes and application thereof and luminescent device |
| CN109336772A (en) * | 2018-10-11 | 2019-02-15 | 上海道亦化工科技有限公司 | A kind of triaromatic amine compound containing spiro structure and application thereof and luminescent device |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106893581A (en) * | 2017-02-23 | 2017-06-27 | 南京高光半导体材料有限公司 | Organic electroluminescent compounds, organic electroluminescence device and its application |
| CN106893581B (en) * | 2017-02-23 | 2019-11-05 | 南京高光半导体材料有限公司 | Organic electroluminescent compounds, organic electroluminescence device and its application |
| CN108658789A (en) * | 2018-05-16 | 2018-10-16 | 上海道亦化工科技有限公司 | A kind of triaromatic amine compound containing fluorenes and application thereof and luminescent device |
| CN109336772A (en) * | 2018-10-11 | 2019-02-15 | 上海道亦化工科技有限公司 | A kind of triaromatic amine compound containing spiro structure and application thereof and luminescent device |
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| CN105503801B (en) | 2018-12-18 |
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