CN105503801B - A kind of aromatic amine luminophor and its organic electroluminescence device - Google Patents

A kind of aromatic amine luminophor and its organic electroluminescence device Download PDF

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CN105503801B
CN105503801B CN201511005601.2A CN201511005601A CN105503801B CN 105503801 B CN105503801 B CN 105503801B CN 201511005601 A CN201511005601 A CN 201511005601A CN 105503801 B CN105503801 B CN 105503801B
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黄锦海
苏建华
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Shanghai Taoe Chemical Technology Co Ltd
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Abstract

The present invention provides a kind of aromatic amine luminophors, the compound has preferable thermal stability, high-luminous-efficiency, high luminance purity, it can be used for making organic electroluminescence device, be applied to organic solar batteries, Organic Thin Film Transistors or organophotoreceptorswith field.The present invention also provides a kind of organic electroluminescence devices, it includes anode, cathode and organic layer, organic layer is comprising one or more layers in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, at least one layer of compound comprising just like structural formula I in organic layer.

Description

A kind of aromatic amine luminophor and its organic electroluminescence device
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of aromatic amine luminophor and its organic Electroluminescent device belongs to organic electroluminescence device field of display technology.
Background technique
Organic electroluminescence device (OLEDs) is between two metal electrodes by spin coating or vacuum evaporation deposition one The device that layer organic material is prepared, a classical three layer organic electroluminescence device include hole transmission layer, luminescent layer And electron transfer layer.The electronics generated by cathode is followed to be incorporated in through electron transfer layer through hole transmission layer in the hole generated by anode Luminescent layer forms exciton, then shines.Organic electroluminescence device can according to need the material by changing luminescent layer to adjust Section emits the light of various needs.
Organic electroluminescence device has self-luminous, wide viewing angle, low energy consumption, efficiency as a kind of novel display technology High, thin, rich in color, fast response time, Applicable temperature range be wide, low driving voltage, can make flexible and transparent Display panel and the particular advantages such as environmental-friendly can be applied on flat-panel monitor and a new generation's illumination, be can also be used as The backlight of LCD.
Since the invention at the bottom of the 1980s, organic electroluminescence device is industrially applied, such as As screens such as camera and mobile phones, but current OLED device, due to low efficiency, it is wider that the factors such as service life is short restrict it General application, especially large screen display, it is therefore desirable to improve the efficiency of device.And restrict one of key factor just It is the performance of the electroluminescent organic material in organic electroluminescence device.It is voltage-operated in application additionally, due to OLED device When, Joule heat can be generated, so that organic material is easy to happen crystallization, affects service life and the efficiency of device, therefore, it is also desirable to Develop the electroluminescent organic material of stability and high efficiency.
In three primary colors (red, indigo plant, green), feux rouges and green light material have been achieved for very big development recently, also comply with The market demand of panel.For stablizing and efficient blue light material or seldom, due to the high energy gap of blue light, so that for material Requirement it is higher, and stability due to blue phosphor materials and optical purity there are the problem of, develop the indigo plant of efficient stable Color fluorescent material is particularly important.
Summary of the invention
Present invention firstly provides a kind of aromatic amine luminophors, are the compound for having the following structure Formulas I:
Ar1-Ar4Separately it is selected from C6-C60 substitution or unsubstituted aryl, C3-C60 substitution or unsubstituted Heteroaryl, three fragrant (C6-C60) amidos, substitution or unsubstituted carbazyl (C6-C30), (9,9- dialkyl group) fluorenyl, (9, 9- bis- replaces or unsubstituted aryl) fluorenyl, 9,9- are Spirofluorene-based, C6-C60 replaces or unsubstituted dibenzothiophene, C6-C60 replaces or unsubstituted dibenzofuran group；
X is O or S.
Preferably, Ar1-Ar4Independently selected from phenyl, xenyl, naphthalene, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (9,9- bis- replace or unsubstituted aryl) fluorenyl, 9,9- are Spirofluorene-based, replace or unsubstituted Dibenzothiophene, substitution or unsubstituted dibenzofuran group；Wherein above-mentioned Ar1-Ar4It can be further by the alkane of C1-C8 Replaced base；
It is further preferred that the aromatic amine luminophor is the compound of following structural 1-16:
Aromatic amine compounds of the invention can pass through Suzuki coupling reaction and Buchwald-Hartwig reaction system It is standby to obtain.
Aromatic amine compounds of the invention can be applied in organic electroluminescence device, organic solar batteries, organic Thin film transistor (TFT) or organophotoreceptorswith field.
The present invention also provides a kind of organic electroluminescence device, which includes anode, cathode and organic layer, organic layer Comprising one layer in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer or electron transfer layer or One layer or more, wherein at least one layer aromatic amine compounds contained as described in structural formula I in the organic layer:
Wherein Ar1-Ar4And X is defined as described above.
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, barrier layer, luminescent layer, electron transfer layer and electron injection 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 where the aromatic amine compounds as described in structural formula I is luminescent layer；
Preferably, the aromatic amine compounds as described in structural formula I are the compound of structural formula 1-16；
When aromatic amine compounds as described in structural formula I are prepared for luminescent device, it can be used alone, it can also be with Other compounds are used in mixed way；Aromatic amine compounds as described in structural formula I can be used alone one such compound, It can also be simultaneously using two or more the compound in structural formula I.
Organic electroluminescence device of the invention, further preferred mode are that the organic electroluminescence device includes sun Pole, hole transmission layer, luminescent layer, electron transfer layer and cathode wherein contain one or more kinds of structural formula I in luminescent layer Compound；It is further preferred that the compound containing one or more kinds of structural formula 1-16 in luminescent layer.
The compound of structural formula I of the invention can be used as the single luminescent layer of non-impurity-doped or doping luminescent layer, wherein structure Compound of formula I is as material of main part, and content is 20-99.9%, the preferably 80-99% of entire luminous layer weight, more preferably 90-99%；When as guest materials, content is the 0.1-50%, preferably 0.5%-10% of entire luminescent layer.
The overall thickness of organic electroluminescence device organic layer of the invention is 1-1000nm, preferably 50-500nm.
When having the compound of structural formula I using the present invention, can arrange in pairs or groups makes organic electroluminescence device of the invention With other materials, such as in hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and barrier layer Deng, and obtain blue and green light, yellow light, feux rouges or white light.
The hole transmission layer and hole injection layer of organic electroluminescence device of the present invention, material requested have good hole Transmission performance can effectively be transferred to hole on luminescent layer from anode.It may include that other small molecules and macromolecule are organic Compound, including but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanine Class compound, the miscellaneous triphen (hexanitrilehexaazatriphenylene) of six cyano six, 2,3,5,6- tetra- fluoro- 7,7', 8, Tetra- cyanogen dimethyl-parabenzoquinone (F4-TCNQ) of 8'-, polyvinyl carbazole, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of organic electroluminescence device of the invention has the good characteristics of luminescence, can be adjusted according to the needs The range of visible light.Except it is of the invention there is Compounds of structural formula I in addition to, following compound can also be contained, but not limited to this, Naphthalene compounds, compound of fluorene class, luxuriant and rich with fragrance class compound, bend class compound, glimmering anthracene compound, anthracene class chemical combination at pyrene compound Object, pentacene class compound, class compound, two aromatic ethylene class compounds, triphenylamine ethylene compounds, aminated compounds, Benzimidazoles compound, furfuran compound, organic metal chelate complex.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires good electronic transmission performance, energy It reaches in effectively electronics from cathode transport to luminescent layer, there is very big electron mobility.It can choose following compound, but It is not limited to this: oxa- oxazole, thiazole compound, triazole compound, three nitrogen piperazine class compounds, triazine class chemical combination Object, quinoline class compound, phenodiazine anthracene compound, siliceous heterocycle compound, quinolines, ferrosin class compound, Metallo-chelate (such as Alq3), fluorine substituted benzene compound, benzimidazoles compound.
Electronics effectively can be injected into organic layer from cathode by the electron injecting layer of organic electroluminescence device of the present invention In, it is mainly selected from the alkali metal perhaps compound of alkali metal or compound or alkali selected from alkaline-earth metal or alkaline-earth metal Metal complex can choose following compound, but 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, alkali metal Or the organic complex of alkaline-earth metal；Preferably lithium, lithium fluoride, lithia, lithium nitride, 8-hydroxyquinoline lithium, caesium, carbonic acid Caesium, 8-hydroxyquinoline caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, magnesia, these compounds can individually make With that can also be used with mixture, can also be used cooperatively with other electroluminescent organic materials.
Each layer of organic layer in organic electroluminescence device of the invention can be steamed by vacuum vapour deposition, molecular beam It is prepared by the modes such as plating method, the dip coating for being dissolved in solvent, spin-coating method, stick coating method or inkjet printing.Metal motor can be made It is prepared with vapour deposition method or sputtering method.
Device experimental shows aromatic amine compounds of the present invention as described in structural formula I, has preferable thermal stability, height Luminous efficiency, high luminance purity.It is imitated using the organic electroluminescence device of aromatic amine compounds production with electroluminescent The advantage that rate is good and excitation purity is excellent and the service life is long.
Detailed description of the invention
Fig. 1 is a kind of organic electroluminescence device structural schematic diagram of the invention；
Wherein, 110 it is represented as glass substrate, 120 are represented as anode, and 130 are represented as hole injection layer, 140 hole transports Layer, 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 cathode.
Specific embodiment
In order to describe the present invention in more detail, spy lifts following example, and but not limited to this.
Embodiment 1
The synthesis of compound 1
The synthesis of intermediate 1-1
In three-necked flask, 2- methyl-bromobenzoate (21.4g, 0.1mol), 1- naphthalene boronic acids (17g, 0.1mol), carbon is added Sour potassium (27g, 0.2mol), tetra-triphenylphosphine palladium (1g), 200ml tetrahydrofuran and 100ml water are heated to reflux 12 under nitrogen protection Hour, it is cooling, it is extracted with ethyl acetate, dry, concentration, crude product obtains 24.1g, yield 92% through column chromatographic purifying.
The synthesis of intermediate 1-2
In three-necked flask, intermediate 1-1 (20g, 77mmol) and polyphosphoric acids (200g) is added, is heated under nitrogen protection It is reacted 5 hours to 160 degree, it is cooling, it heats in ice water, is extracted with dichloromethane, dry, concentration, crude product ethyl alcohol recrystallization, Obtain 13g, yield 74%.
The synthesis of intermediate 1-3
In three-necked flask, intermediate 1-2 (12g, 52mmol) and 200ml glacial acetic acid is added, is heated to 80 degree, slowly drips It is added bromine (16.7g, 104mmol), reacts 5 hours, cooling, filtering, then yield 16g, yield are obtained with ethyl alcohol recrystallization 81%.
The synthesis of intermediate 1-4
In flask, adjacent bromo-iodobenzene (28g, 0.1mol), 4- dibenzofurans boric acid (21g, 0.1mol), potassium carbonate is added (20.4g, 0.15mol), tetra-triphenylphosphine palladium (0.5g), water (150ml) and tetrahydrofuran (300ml), under nitrogen protection plus Heat reflux 5 hours, it is cooling, it is extracted with dichloromethane, dry, concentration obtains product 21.5g, yield 57% through column chromatographic purifying.
The synthesis of intermediate 1-5
In three-necked flask, intermediate 1-4 (6.4g, 20mmol) and 100ml anhydrous tetrahydro furan is added, is cooled to subzero 78 degree, be slowly added to the hexane solution (8ml, 20mmol) of 2.5M n-BuLi, react 2 hours, be slowly added to 80ml dissolved with The tetrahydrofuran solution (6.2g, 16mmol) of intermediate 1-3, drips off, and is slowly increased to room temperature, reacts 2 hours.Water is added, with two Chloromethanes extraction, dry, concentration is added glacial acetic acid 100ml and 3ml concentrated hydrochloric acid, is heated to reflux 5 hours, removes solvent, crude product Product 3.5g, yield 36% are obtained through column chromatographic purifying.
The synthesis of compound 1
In three-necked flask, intermediate 1-5 (2g, 3.3mmol), diphenylamines (1.6g, 9.8mmol), sodium tert-butoxide is added (1.3g, 13.2mmol), palladium acetate (0.1g), X-phos (0.3g) and toluene 50ml.It is heated to reflux 12 hours, it is cooling, it removes Solvent, crude product obtain product 2.0g, yield 77% through column chromatographic purifying.
Embodiment 2
The synthesis of compound 8
Synthetic method is as the 1 of compound synthetic method, in addition to replacing hexichol with 2- anilino- -9,9- dimethyl fluorene Outside amine, yield 70%.
Embodiment 3
The synthesis of compound 9
Intermediate 9-1
Synthetic method is as with intermediate 1-4, other than replacing 4- dibenzofurans with 4- dibenzothiophenes, yield 65%.
The synthesis of intermediate 9-2
Synthetic method is as with intermediate 1-5, other than replacing intermediate 1-4 with intermediate 9-1, yield 40%.
The synthesis of compound 9
Synthetic method is as the synthesis of compound 1, other than replacing intermediate 1-5 with intermediate 9-2, yield 80%.
Embodiment 4
The synthesis of compound 16
Synthetic method is as the synthetic method of compound 9, in addition to replacing diphenylamines with 2- anilino- -9,9- dimethyl fluorene Outside, yield 79%.
Embodiment 5
The preparation of organic electroluminescence device
OLED is prepared using the compound of embodiment 1.
Firstly, by electrically conducting transparent ito glass substrate 110 (having anode 120 above) (the limited public affairs of South China glass group share Department) successively pass through: deionized water, ethyl alcohol, acetone and deionized water were cleaned, then with oxygen plasma treatment 30 seconds.
Then, HIL (60nm) is deposited on ITO and is used as hole injection layer 130.
Then, compound N PB is deposited, forms the hole transmission layer 140 of 10nm thickness.
Then, the luminescent layer 150 of 40nm thickness is deposited on the hole transport layer.Wherein, luminescent material based on MADN, and with The compound 1 of 5% weight ratio is as doping guest materials.
Then, the Alq of 20nm thickness is deposited on the light-emitting layer3As electron transfer layer 160.
Finally, vapor deposition 1nm LiF is electron injecting layer 170 and 100nm Al as device cathodes 180.
Prepared device is measured with Photo Research PR650 spectrometer in 10mA/cm2Current density under Brightness is 740cd/m2.Emit blue light.
Embodiment 6
The preparation method of device is as embodiment 5, other than replacing the compound 1 of embodiment 5 with compound 8.
Prepared device is measured with Photo Research PR650 spectrometer in 10mA/cm2Current density under Brightness be 815cd/m2.Emit blue light.
Embodiment 7
The preparation method of device is as embodiment 5, other than replacing the compound 1 of embodiment 5 with compound 9.
Prepared device is measured with Photo Research PR650 spectrometer in 10mA/cm2Current density under Brightness be 695cd/m2.Emit blue light.
Embodiment 8
The preparation method of device is as embodiment 5, other than replacing the compound 1 of embodiment 5 with compound 16.
Prepared device is measured with Photo Research PR650 spectrometer in 10mA/cm2Current density under Brightness be 855cd/m2.Emit blue light.
Comparative example
The preparation method of device is as embodiment 5, other than the compound 1 for replacing embodiment 5 with compound BD1.
Prepared device is measured with Photo Research PR650 spectrometer in 10mA/cm2Current density under Brightness be 540cd/m2.Emit blue light.
Under identical brightness conditions, using the brightness of the organic electroluminescence device of aromatic amine material of the present invention preparation Higher than comparative example, as described above, the compound of the present invention has high stability, the organic electroluminescence device of preparation has height Efficiency and optical purity.
The structural formula of compound described in device is as follows:
The preferred embodiment of the present invention has been described in detail above.It should be appreciated that the ordinary skill of this field is without wound The property made labour, which according to the present invention can conceive, makes many modifications and variations.Therefore, all technician in the art Pass through the available technology of logical analysis, reasoning, or a limited experiment on the basis of existing technology under this invention's idea Scheme, all should be within the scope of protection determined by the claims.

Claims (9)

1. a kind of aromatic amine luminophor, it is characterised in that it is the compound for having the following structure Formulas I:
Ar1-Ar4Independently selected from phenyl, xenyl, naphthalene, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, fluorenyl, 9,9- spiro fluorene Base, dibenzothiophene, dibenzofuran group；Or above-mentioned Ar1-Ar4Further replaced the alkyl by C1-C8；
X is O or S.
2. aromatic amine luminophor according to claim 1, it is characterised in that it is the change of following structural 1-16 Close object:
3. a kind of organic electroluminescence device comprising anode, cathode and organic layer, organic layer include luminescent layer, hole injection It is layer, hole transmission layer, hole blocking layer, electron injecting layer, one or more layers in electron transfer layer, it is characterised in that have At least one layer includes the aromatic amine compounds as described in claim 1 as described in structural formula I in machine layer.
4. organic electroluminescence device according to claim 3, it is characterised in that the aromatic amine as described in structural formula I Layer where closing object is luminescent layer.
5. organic electroluminescence device according to claim 3, it is characterised in that the aromatic amine as described in structural formula I It closes object to be used alone, or is used in mixed way with other compounds.
6. organic electroluminescence device according to claim 3, it is characterised in that the aromatic amine as described in structural formula I It closes object and one such compound is used alone, or simultaneously using two or more the compound in structural formula I.
7. organic electroluminescence device according to claim 3, it is characterised in that it includes anode, hole transmission layer, hairs Photosphere, electron transfer layer and cathode, it is characterised in that the compound containing one or more kinds of structural formula I in luminescent layer.
8. organic electroluminescence device according to claim 3, it is characterised in that it includes anode, hole transmission layer, hairs Photosphere, electron transfer layer and cathode, it is characterised in that the compound contained in luminescent layer is structural formula 1- as claimed in claim 2 16 compound.
9. organic electroluminescence device according to claim 3, it is characterised in that the compound of structural formula I is as non-impurity-doped Single luminescent layer or doping luminescent layer, wherein for Compounds of structural formula I as material of main part, content is entire luminous layer weight 20-99.9%.
CN201511005601.2A 2015-12-29 2015-12-29 A kind of aromatic amine luminophor and its organic electroluminescence device Active CN105503801B (en)

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