CN107501218A - A kind of pyrene class organic electroluminescent compounds and its organic electroluminescence device - Google Patents
A kind of pyrene class organic electroluminescent compounds and its organic electroluminescence device Download PDFInfo
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Abstract
The invention provides a kind of pyrene class organic electroluminescent compounds, and it has following structure：The compound has preferable heat endurance, high-luminous-efficiency, high luminance purity, can be used for making organic electroluminescence device, applied to organic solar batteries, OTFT or organophotoreceptorswith field.Present invention also offers a kind of organic electroluminescence device, the device includes anode, negative electrode and organic layer, organic layer includes at least one layer 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, the organic electroluminescence device have the advantages of excellent electroluminescent efficiency, excitation and long lifespan in organic layer.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of pyrene class electroluminescent organic material and its has
Organic electroluminescence devices, belong to organic electroluminescence device display technology field.
Technical background
Organic electroluminescence device (OLEDs) is by spin coating or vacuum evaporation deposition one between two metal electrodes
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.Hole follows the electronics as caused by negative electrode to be incorporated in through electron transfer layer through hole transmission layer as caused by anode
Luminescent layer forms exciton, then lights.Organic electroluminescence device can be adjusted as desired by the material for changing luminescent layer
Section launches the light of various needs.
Organic electroluminescence device has self-luminous, wide viewing angle, low energy consumption, efficiency as a kind of new Display Technique
High, thin, rich in color, fast response time, Applicable temperature scope are wide, low driving voltage, can make flexible with it is transparent
Display panel and the particular advantages such as environment-friendly, it can apply on flat-panel monitor and a new generation's illumination, can also conduct
LCD backlight.
Since the invention at the bottom of the 1980s, organic electroluminescence device has industrially been applied, such as
As screens such as camera and mobile phones, but current OLED, because efficiency is low, it is wider that the factors such as service life is short restrict it
General application, particularly 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
When, Joule heat can be produced so that organic material easily crystallizes, and have impact on life-span and the efficiency of device, therefore, it is also desirable to
Develop the electroluminescent organic material of stability and high efficiency.
Among 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 stable 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 the problem of stability due to blue phosphor materials and optical purity are present, therefore develop the indigo plant of efficient stable
Color fluorescent material is particularly important.
The content of the invention
The invention provides a kind of pyrene class organic electroluminescent compounds, and it is the compound with following structural formula I：
Wherein, R1And R2Independently selected from hydrogen, substitution either unsubstituted C1-C20 alkyl, substitution or unsubstituted
C3-C10 cycloalkyl, C1-C8 alkoxy, substitution or unsubstituted C6-C30 aryl；
R3And R4Independently selected from substitution or unsubstituted C1-C20 alkyl；
Ar1And Ar2Independently selected from substitution or unsubstituted C6-C30 aryl.
Preferably, R1And R2Independently selected from hydrogen, methyl, ethyl, propyl group, isopropyl, isobutyl group, normal-butyl, the tert-butyl group,
N-pentyl, isopentyl, n-hexyl, cyclohexyl, cyclobutyl, cyclopropyl, octyl group, phenyl, tolyl；
R3And R4Independent is selected from methyl, ethyl, propyl group, isopropyl, phenyl；
Ar1And Ar2Independently selected from phenyl, xenyl, naphthyl, above aryl is further former by C1-C12 alkyl, fluorine
Son, cyano group substitution.
It is further preferred that described pyrene class organic electroluminescent compounds are following structural 1-40 compound：
The present invention organic electroluminescent compounds can apply organic electroluminescence device, organic solar batteries,
OTFT and organophotoreceptorswith field.
Present invention also offers a kind of organic electroluminescence device, the device includes anode, negative electrode 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
More than one layer, wherein at least one layer pyrene class organic electroluminescent compounds contained as described in structural formula I in the organic layer：
R1-R4、Ar1And Ar2It 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；
The layer where pyrene class organic electroluminescent compounds wherein as described in structural formula I is luminescent layer；
The compound that pyrene class organic electroluminescent compounds wherein described in structural formula I are structural formula 1-40；
When pyrene class organic electroluminescent compounds as described in structural formula I are used for luminescent device preparation, it can be used alone,
It can also be used in mixed way with other compounds；Pyrene class organic electroluminescent compounds as described in structural formula I can be used alone
A kind of compound therein, two or more the compound in structural formula I can also be used simultaneously.
The organic electroluminescence device of the present invention, further preferred mode are that the organic electroluminescence device includes sun
Contain one or more kinds of structural formula I in pole, hole transmission layer, luminescent layer, electron transfer layer and negative electrode, wherein luminescent layer
Compound；It is further preferred that the compound containing one or more kinds of structural formula 1-40 in luminescent layer.
The structural formula I of present invention compound can be used as the single luminescent layer of non-impurity-doped or doping luminescent layer, wherein structure
Compound of formula I is 20-99.9%, the preferably 80-99% of whole luminous layer weight as material of main part, its concentration, is more preferably
90-99%；During as guest materials, its concentration is the 0.1-50%, preferably 0.5%-10% of whole luminescent layer.Present invention tool
There is structural formula I compound preferably as guest emitting material.
The gross thickness of the organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
The present invention organic electroluminescence device using the present invention have structural formula I compound when, can use take
With other materials, such as hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and barrier layer, and
Obtain blue and green light, gold-tinted, 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, effectively hole can be transferred on luminescent layer from anode.Other small molecules can be included and macromolecule is organic
Compound, including but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanine
Class compound, six cyano group, six miscellaneous triphen (hexanitrilehexaazatriphenylene), 2,3,5,6- tetra- fluoro- 7,7', 8,
The cyanogen dimethyl-parabenzoquinones (F4-TCNQ) of 8'- tetra-, PVK, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of the organic electroluminescence device of the present invention, has the good characteristics of luminescence, can adjust as needed
The scope of visible ray.Luminescent layer except comprising the present invention have Compounds of structural formula I in addition to, can also be including but not limited to naphthalenes
Compound, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance class compound,Class compound, glimmering anthracene compound, anthracene compound, and
Five benzene-like compounds, class compound, two aromatic ethylene class compounds, triphenylamine ethylene compounds, aminated compounds, benzo miaow
Azole compounds, 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 is enough effectively electronics from cathode transport to luminescent layer in, there is very big electron mobility.It can select but be not limited to oxygen
Miscellaneous oxazole, thiazole compound, triazole compound, three nitrogen piperazine class compounds, triazine class compound, quinoline class chemical combination
Thing, phenodiazine anthracene compound, siliceous heterocycle compound, quinolines, ferrosin class compound, metallo-chelate is (such as
Alq3), fluorine substituted benzene compound, benzimidazoles compound.
The electron injecting layer of organic electroluminescence device of the present invention, electronics effectively can be injected into organic layer from negative electrode
In, it is mainly selected from the compound of alkali metal or alkali metal, or compound or alkali selected from alkaline-earth metal either alkaline-earth metal
Metal complex, it can select but be not limited to alkali metal, the oxide of alkaline-earth metal, rare earth metal, alkali metal or halogenation
Oxide either halide, the oxide of rare earth metal or halide, alkali metal or the alkaline-earth metal of thing, alkaline-earth metal
Organic complex；Preferably lithium, lithium fluoride, lithia, lithium nitride, 8-hydroxyquinoline lithium, caesium, cesium carbonate, 8-hydroxyquinoline caesium,
Calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, magnesia, these compounds can be used alone can also mixture make
With can also be used cooperatively with other electroluminescent organic materials.
Each layer of organic layer in the organic electroluminescence device of the present invention, it 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.It can make for metal motor
Prepared with vapour deposition method or sputtering method.
Device experimental shows pyrene class organic electroluminescent compounds of the present invention as described in structural formula I, have preferably heat steady
It is qualitative, high-luminous-efficiency, high luminance purity.The organic electroluminescence device made using the pyrene class organic electroluminescent compounds
With electroluminescent efficiency, excitation is excellent and the advantages of long lifespan.
Brief description of the drawings
Fig. 1 is the mass spectrogram of compound 4；
Fig. 2 is the nmr spectrum of compound 17；
Fig. 3 is the nmr spectrum of compound 20；
Fig. 4 is a kind of organic electroluminescence device structural representation of the present invention,
Wherein, 110 glass substrate is represented as, 120 are represented as anode, and 130 are represented as hole injection layer, and 140 are represented as sky
Cave transport 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 the moon
Pole；
Fig. 5 is device current density-power efficiency graph of a relation；
Fig. 6 is the emission spectrum under 6V of embodiment 6.
Embodiment 1
The synthesis of compound 1
Intermediate 1-1 synthesis
In single-necked flask, aniline (0.89g, 9.6mmol) is added, the bromo- 2- methyldiphenyls of 4- and furans (2.5g,
9.6mmol), sodium tert-butoxide (1.84g, 19.2mmol), x-phos (0.47g), palladium (0.2g), toluene (40mL), in nitrogen
It is heated to reflux under gas shielded 2 hours, after reaction terminates, revolving removes solvent, crude product petroleum ether/dichloromethane (8:1)
Eluant, eluent carries out column chromatography purifying (silicagel column), obtains white solid 2.24g, yield 66%.
The synthesis of compound 1
1,6- dibromos pyrene (2.0g, 5.6mmol) and intermediate 1-1 (3.8g, 14mmol) are dissolved in 50mL toluene, then and
Sodium tert-butoxide (1.6g, 16.8mmol), which is mixed, to be added in single-necked flask.Under argon gas protection, then add and urge into mixture
The palladium and tri-butyl phosphine of agent amount, it is heated to reflux 4 hours.After reaction terminates, question response mixture is cooled to room temperature, rotation
Solvent is evaporated off, crude product purifies to obtain yellow solid 1.6g, yield 40% through column chromatography.
Embodiment 2
The synthesis of compound 4
Intermediate 4-1
Synthetic method is as intermediate 1-1 synthesis, in addition to replacing aniline with 4- isopropyl anilines, yield 67%
The synthesis of compound 4
Synthetic method is as the synthesis of compound 1, and in addition to replacing intermediate 1-1 with intermediate 4-1, yield is
50%, Fig. 1 are its mass spectrogram.
Embodiment 3
The synthesis of compound 17
Synthetic method is as the synthesis of compound 1, except replacing 1,6- dibromos with 1,6- diisopropyl -3,8- dibromos pyrene
Outside pyrene, yield 59%, the nmr spectrum of compound 17 is as shown in Figure 2.
Embodiment 4
The synthesis of compound 20
For synthetic method as the synthesis of compound 1, raw materials used is intermediate 4-1 and 1,6- diisopropyl -3,8- bis-
Bromine pyrene, yield 53%, its nmr spectrum such as Fig. 3.
Embodiment 5
The preparation of organic electroluminescence device
OLED is prepared using the compound of embodiment 1.
First, by electrically conducting transparent ito glass substrate 110 (carrying anode 120 above) (the limited public affairs of South China glass group share
Department) pass through successively：Deionized water, ethanol, acetone and deionized water are cleaned, then with oxygen plasma treatment 30 seconds.
Then, PEDOT thick spin coating 35nm on ITO:PSS (Polyglycolic acid fibre-poly- (styrene sulfonate)) is
Hole injection layer 130, dried 30 minutes at 150 DEG C；
Then, compound N PB is deposited, forms the thick hole transmission layers 140 of 30nm.
Then, the thick luminescent layers 150 of 30nm are deposited on hole transmission layer.Wherein, MADN is main body luminescent material, and with
5% weight than compound 1 as doping guest materials.
Then, the thick TPBI of 30nm are deposited on luminescent layer as electron transfer layer 160.
Finally, evaporation 1nm LiF are electron injecting layer 170 and 100nm Al as device cathodes 180.
It is close that prepared device (its structural representation such as Fig. 4) with Photo Research PR650 spectrometers measures electric current
Degree and power efficiency graph of a relation such as Fig. 5, launch blue light.
Embodiment 6
The preparation method of device is as embodiment 5, in addition to the compound 1 of embodiment 5 is replaced with compound 4.It is made
Standby device (its structural representation such as Fig. 4) measures current density and power efficiency with Photo Research PR650 spectrometers
Graph of a relation such as Fig. 5.Device such as Fig. 6 of the emission spectrum under 6V, launch blue light.
Embodiment 7
The preparation method of device is as embodiment 5, in addition to the compound 1 of embodiment 5 is replaced with compound 17.It is made
Standby device (its structural representation such as Fig. 4) measures current density and power efficiency with Photo Research PR650 spectrometers
Graph of a relation such as Fig. 5, launch blue light.
Embodiment 8
The preparation method of device is as embodiment 5, in addition to the compound 1 of embodiment 5 is replaced with compound 20.It is made
Standby device (its structural representation such as Fig. 4) measures current density and power efficiency with Photo Research PR650 spectrometers
Graph of a relation such as Fig. 5, launch blue light.
Comparative example
The preparation method of device is as embodiment 5, in addition to replacing the compound 1 of embodiment 5 with compound BD.It is made
Standby device measures current density and power efficiency graph of a relation such as Fig. 5 with Photo Research PR650 spectrometers, and transmitting is blue
Light.
Under identical brightness conditions, the power of the organic electroluminescence device prepared using blue light emitting material of the present invention
Efficiency is far above comparative example, as described above, the compound of the present invention has high stability, the organic electroluminescence device of preparation
With high efficiency and optical purity.
The structural formula of compound described in device is as follows：
Preferred embodiment of the invention described in detail above.It should be appreciated that the ordinary skill of this area is without wound
The property made work can makes many modifications and variations according to the design of the present invention.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 in the protection domain being defined in the patent claims.
Claims (10)
1. a kind of pyrene class organic electroluminescent compounds, it is characterised in that be the compound with following structural formula I：
Wherein, R1And R2Independently selected from hydrogen, substitution either unsubstituted C1-C20 alkyl, substitution or unsubstituted C3-
C10 cycloalkyl, C1-C8 alkoxy, substitution or unsubstituted C6-C30 aryl；
R3And R4Independently selected from substitution or unsubstituted C1-C20 alkyl；
Ar1And Ar2Independently selected from substitution or unsubstituted C6-C30 aryl.
2. pyrene class organic electroluminescent compounds as claimed in claim 1, it is characterised in that R1And R2Independently select
From hydrogen, methyl, ethyl, propyl group, isopropyl, isobutyl group, normal-butyl, the tert-butyl group, n-pentyl, isopentyl, n-hexyl, hexamethylene
Base, cyclobutyl, cyclopropyl, octyl group, phenyl, tolyl；
R3And R4Independent is selected from methyl, ethyl, propyl group, isopropyl, phenyl；
Ar1And Ar2Independently selected from phenyl, xenyl, naphthyl, above aryl is further by C1-C12 alkyl, fluorine atom, cyanogen
Base substitutes.
3. pyrene class organic electroluminescent compounds as claimed in claim 1, it is characterised in that it is following structural 1-40's
Compound：
4. a kind of organic electroluminescence device, the device includes anode, negative electrode and organic layer, and organic layer includes luminescent layer, hole
At least one layer in implanted layer, hole transmission layer, hole blocking layer, electron injecting layer or electron transfer layer, it is characterised in that institute
State in organic layer at least one layer and contain pyrene class organic electroluminescent compounds as claimed in claim 1.
5. organic electroluminescence device as claimed in claim 4, it is characterised in that the pyrene class Organic Electricity as described in structural formula I
Layer where electro luminescent compounds is luminescent layer.
6. organic electroluminescence device according to claim 4, it is characterised in that the pyrene class Organic Electricity as described in structural formula I
Electro luminescent compounds are structural formula 1-40 compound.
7. organic electroluminescence device as claimed in claim 4, it is characterised in that the pyrene class Organic Electricity as described in structural formula I
A kind of compound therein is used alone in electro luminescent compounds, or uses the two or more compounds in structural formula I simultaneously.
8. organic electroluminescence device as claimed in claim 4, it is characterised in that the pyrene class Organic Electricity as described in structural formula I
Material of main part of the electro luminescent compounds as luminescent layer, its concentration are the 20-99.9% of whole luminous layer weight.
9. organic electroluminescence device as claimed in claim 4, it is characterised in that the pyrene class Organic Electricity as described in structural formula I
Guest materials of the electro luminescent compounds as luminescent layer, its concentration are the 0.1-50% of whole luminous layer weight.
10. organic electroluminescence device as claimed in claim 4, it is characterised in that organic electroluminescence device organic layer
Gross thickness is 1-1000nm.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2021075493A (en) * | 2019-11-11 | 2021-05-20 | 三菱ケミカル株式会社 | Oled element forming composition and oled element |
| CN113429399A (en) * | 2021-07-10 | 2021-09-24 | 浙江华显光电科技有限公司 | Pyrene derivative, light emitting device material and light emitting device |
Citations (1)
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| CN106220606A (en) * | 2010-04-09 | 2016-12-14 | 株式会社半导体能源研究所 | Aromatic amine derivant, light-emitting component, luminescent device, electronic device and illuminating device |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106220606A (en) * | 2010-04-09 | 2016-12-14 | 株式会社半导体能源研究所 | Aromatic amine derivant, light-emitting component, luminescent device, electronic device and illuminating device |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2021075493A (en) * | 2019-11-11 | 2021-05-20 | 三菱ケミカル株式会社 | Oled element forming composition and oled element |
| JP7342639B2 (en) | 2019-11-11 | 2023-09-12 | 三菱ケミカル株式会社 | Composition for forming an OLED element and OLED element |
| CN113429399A (en) * | 2021-07-10 | 2021-09-24 | 浙江华显光电科技有限公司 | Pyrene derivative, light emitting device material and light emitting device |
| CN113429399B (en) * | 2021-07-10 | 2024-03-26 | 浙江华显光电科技有限公司 | Pyrene derivative, light-emitting device material and light-emitting device |
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Application publication date: 20171222 |