CN108864012A - One kind is based on dibenzofurans compound and application thereof and organic electroluminescence device - Google Patents

One kind is based on dibenzofurans compound and application thereof and organic electroluminescence device Download PDF

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CN108864012A
CN108864012A CN201811023317.1A CN201811023317A CN108864012A CN 108864012 A CN108864012 A CN 108864012A CN 201811023317 A CN201811023317 A CN 201811023317A CN 108864012 A CN108864012 A CN 108864012A
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compound
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organic electroluminescence
dibenzofurans
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黄锦海
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Shanghai Taoe Chemical Technology Co Ltd
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Abstract

The present invention provides one kind to be based on dibenzofurans compound, has the following structure formula：Should have preferable thermal stability, high-luminous-efficiency, high luminance purity based on dibenzofurans compound, and can be applied to organic electroluminescence device, solar battery, Organic Thin Film Transistors or organophotoreceptorswith field.The present invention also provides a kind of organic electroluminescence devices, the device includes anode, cathode 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 or electron transfer layer, in organic layer at least one layer containing if structural formula I is based on dibenzofurans compound, have the advantages that electroluminescent efficiency well using organic electroluminescence device make based on dibenzofurans compound and excitation purity be excellent and the service life is grown.

Description

One kind is based on dibenzofurans compound and application thereof and organic electroluminescence device
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to one kind is based on dibenzofurans compound and its use On the way, a kind of organic electroluminescence device is further related to.
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.And restricting one of key factor is exactly in organic electroluminescence device The performance of electroluminescent organic material.Additionally, due to OLED device when applying voltage-operated, 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 organic electroluminescence of stability and high efficiency Luminescent material.
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
The present invention provides one kind to be based on dibenzofurans compound, is the compound for having the following structure Formulas I：
Wherein, R1-R8Virtue independently selected from hydrogen, deuterium, halogen, the alkyl of C1-C12, substitution or unsubstituted C6-C30 Base；
Ar be selected from replace or the aryl of unsubstituted C6-C30, substitution or unsubstituted C3-C30 heteroaryl, take The carbazyl of the triaromatic amine base of generation or unsubstituted C18-C30, substitution or unsubstituted C18-C30.
Optionally, R1-R8Selected from hydrogen, methyl, phenyl, tert-butyl, ethyl, propyl, isopropyl.
Optionally, Ar is selected from phenyl, deuterated benzene, diphenyl phenyl, naphthalene, naphthylphenyl, xenyl, three simultaneously phenyl, anthracene Base, phenanthryl, pyrenyl, base, fluoranthene base, acenaphthenyl, acenaphthylene base, (9,9- dialkyl group) fluorenyl, (substitution or unsubstituted of 9,9- bis- Aryl) fluorenyl, substitution or unsubstituted dibenzothiophene and substitution or unsubstituted dibenzofuran group, triaromatic amine Base and substitution or unsubstituted carbazyl.
Optionally, the compound for being following structural 1-28 based on dibenzofurans compound：
One kind of the invention is based on dibenzofurans compound can be prepared by Suzuki coupling reaction.
Of the invention can be applied to organic electroluminescence device based on dibenzofurans compound, solar battery, has Machine 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 Include at least one in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer Layer, in the organic layer it is at least one layer of containing as described in structural formula I based on dibenzofurans compound.
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.
Optionally, the layer where the compound based on dibenzofurans is luminescent layer.
Being used alone based on dibenzofurans compound as described in structural formula I, or be used in mixed way with other compounds；Such as One such compound can be used alone based on dibenzofurans compound described in structural formula I, can also use simultaneously Two or more compound in structural formula I；Be used alone it is a kind of selected from structural formula 1-28 based on dibenzofurans Compound, or simultaneously using two or more selected from structural formula 1-28 based on dibenzofurans compound.
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 concentration is 20%-99.9%, the preferably 80%-99% of entire luminous layer weight, more Preferably 90%-99%；When as guest materials, concentration is the 0.1%-50%, preferably 0.5%- of entire luminescent layer 10%.
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.In addition to can be used with the compound of the present invention It outside, can also include other small molecules and macromolecular organic compound, including but not limited to carbazole compound, triaromatic amine Close object, benzidine compound, compound of fluorene class, phthalocyanine-like compound, the miscellaneous triphen of six cyano six (hexanitrilehexaazatriphenylene), tetra- cyanogen dimethyl-parabenzoquinone (F4- of 2,3,5,6- tetra- fluoro- 7,7', 8,8'- TCNQ), 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, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance class compound,Class compound, glimmering anthracene compound, anthracene class chemical combination 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, and 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 show the present invention as described in structural formula I based on dibenzofurans compound, there is preferable thermostabilization Property, high-luminous-efficiency, high luminance purity.Had using the organic electroluminescence device based on the production of dibenzofurans compound The advantage that electroluminescent efficiency 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 transmission layer, and 140 are represented as sending out Photosphere, 150 are represented as electron transfer layer, and 160 are represented as electron injecting layer, and 170 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 synthetic route of compound 1
The synthetic method of intermediate 1-1
In there-necked flask, chlorobenzoyl chloride (30.8g, 0.22mol), dry methylene chloride (250mL) is added, in nitrogen protection Under, alchlor (35g, 0.26mol) is added at 0 DEG C, then the bromo- dibenzofurans of 2- (49g, 0.2mol) is added portionwise, adds Finish stirring 2 hours, add water quenching reaction, organic phase is crossed silica gel after washing liquid separation, is spin-dried for, crude product ethyl alcohol recrystallization obtains Off-white powder 48g, yield 69%.
The synthetic method of intermediate 1-2
In flask, it is added intermediate 1-1 (35g, 100mmol), anhydrous tetrahydro furan (400mL), under nitrogen protection It is cooled to 0 DEG C, is slowly added to 2- xenyl magnesium bromide grignard reagent (120mmol), is heated to reflux stirring 3 hours, it is cooling, then It is slowly added to the dilute hydrochloric acid solution of 1N, pH value is improved to 7, is extracted with dichloromethane, dries, being concentrated, glacial acetic acid (200ml) is added It with concentrated hydrochloric acid (10ml), is heated to reflux 5 hours, cooling removes solvent, Jia Shui, is extracted with dichloromethane, dries, being concentrated, thick to produce Object obtains product 10g, yield 21% through column chromatographic purifying.
The synthetic method of compound 1
In flask, it is added intermediate 1-2 (2g, 4.1mmol), 9- phenyl -10- anthracene boric acid (1.22g, 4.1mmol), carbon Sour potassium (1.4g, 10mmol), four triphenyl phosphorus (50mg), tetrahydrofuran (30mL), water (10mL) heat back under nitrogen protection Stream 5 hours, it is cooling, tetrahydrofuran is removed, is extracted with dichloromethane, is dried, filtered with anhydrous sodium sulfate, is concentrated, product first Benzene is recrystallized to give 2.1g, yield 79%.
The synthetic method of other embodiments such as compound 1, be all use intermediate 1-2 as raw material, then with other Anthracene acid reaction, table 1 specific as follows：
Table 1
Embodiment 7
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, compound N PB is deposited, forms the hole transmission layer 130 of 60nm thickness.
Then, the luminescent layer 140 of 40nm thickness is deposited on the hole transport layer, wherein luminescent material based on compound 3, And using the BUBD-1 that weight ratio is 3% as doping guest materials.
Then, the Alq of 20nm thickness is deposited on the light-emitting layer3As electron transfer layer 150.
Finally, vapor deposition 1nm LiF is electron injecting layer 160 and 100nm Al as device cathodes 170.
Prepared device (structural schematic diagram is as shown in Figure 1) is measured with Photo Research PR650 spectrometer 200mA/cm2Current density under current efficiency be 8.3cd/A.
Embodiment 8
The preparation method of device is as embodiment 7, other than replacing the compound 1 of embodiment 7 with compound 2.It is made Standby device (structural schematic diagram is as shown in Figure 1) is measured with Photo Research PR650 spectrometer in 200mA/cm2Electricity Current efficiency under current density is 7.9cd/A.
Embodiment 9
The preparation method of device is as embodiment 7, other than replacing the compound 1 of embodiment 7 with compound 3.It is made Standby device (structural schematic diagram is as shown in Figure 1) is measured with Photo Research PR650 spectrometer in 200mA/cm2Electricity Current efficiency under current density is 8.2cd/A.
Embodiment 10
The preparation method of device is as embodiment 7, other than replacing the compound 1 of embodiment 7 with compound 8.
Prepared device (structural schematic diagram is as shown in Figure 1) is measured with Photo Research PR650 spectrometer 200mA/cm2Current density under current efficiency be 7.8cd/A.
Embodiment 11
The preparation method of device is as embodiment 7, other than replacing the compound 1 of embodiment 7 with compound 11.It is made Standby device (structural schematic diagram is as shown in Figure 1) is measured with Photo Research PR650 spectrometer in 200mA/cm2Electricity Current efficiency under current density is 8.0cd/A.
Embodiment 12
The preparation method of device is as embodiment 7, other than replacing the compound 1 of embodiment 7 with compound 25.It is made Standby device (structural schematic diagram is as shown in Figure 1) is measured with Photo Research PR650 spectrometer in 200mA/cm2Electricity Current efficiency under current density is 7.5cd/A.
Comparative example
The preparation method of device is as embodiment 7, other than the compound 1 for replacing embodiment 7 with compound BH.It is made Standby device (structural schematic diagram is as shown in Figure 1) is measured with Photo Research PR650 spectrometer in 200mA/cm2Electricity Current efficiency under current density is 6.2cd/A.
By comparing, under identical brightness conditions, using the present invention is based on dibenzofurans compound prepare it is organic The current efficiency of electroluminescent device is higher than comparative example, as described above, the compound of the present invention has high stability, preparation Organic electroluminescence device has high 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 those skilled in the art without It needs creative work according to the present invention can conceive and makes many modifications and variations.Therefore, all technologies in the art Personnel are available by logical analysis, reasoning, or a limited experiment on the basis of existing technology under this invention's idea Technical solution, all should be within the scope of protection determined by the claims.

Claims (10)

1. one kind is based on dibenzofurans compound, which is characterized in that be the compound for having the following structure Formulas I：
Wherein, R1-R8Aryl independently selected from hydrogen, deuterium, halogen, the alkyl of C1-C12, substitution or unsubstituted C6-C30；
Ar be selected from replace or the aryl of unsubstituted C6-C30, substitution or unsubstituted C3-C30 heteroaryl, replace or The carbazyl of the triaromatic amine base of the unsubstituted C18-C30 of person, substitution or unsubstituted C18-C30.
2. being based on dibenzofurans compound as described in claim 1, which is characterized in that R1-R8Selected from hydrogen, methyl, phenyl, Tert-butyl, ethyl, propyl, isopropyl.
3. being based on dibenzofurans compound as described in claim 1, which is characterized in that Ar is selected from phenyl, deuterated benzene, hexichol Base phenyl, naphthalene, naphthylphenyl, xenyl, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, acenaphthenyl, acenaphthylene base, (9,9- dialkyl group) fluorenyl, (9,9- bis- replaces or unsubstituted aryl) fluorenyl, substitution or unsubstituted dibenzothiophenes Base and substitution or unsubstituted dibenzofuran group, triaromatic amine base and substitution or unsubstituted carbazyl.
4. being based on dibenzofurans compound as described in claim 1, which is characterized in that be the chemical combination of following structural 1-28 Object：
5. the application described in claim 1 based on dibenzofurans compound in organic electroluminescence device.
6. a kind of organic electroluminescence device, which includes anode, cathode and organic layer, and organic layer includes luminescent layer, hole Implanted layer, hole transmission layer, hole blocking layer, electron injecting layer, at least one layer in electron transfer layer, which is characterized in that institute It states at least one layer of containing as described in claim 1 based on dibenzofurans compound in organic layer.
7. organic electroluminescence device as claimed in claim 6, which is characterized in that described in claim 1 to be based on dibenzo Layer where furan compound is luminescent layer.
8. organic electroluminescence device as claimed in claim 7, which is characterized in that described to be made based on dibenzofurans compound Based on material or guest materials, if weight is the 20%-99.9% of entire luminous layer weight when as material of main part； If when as guest materials, weight is the 0.1%-50% of entire luminous layer weight.
9. organic electroluminescence device as claimed in claim 6, which is characterized in that described in claim 1 to be based on dibenzo Furan compound is used alone, or is used in mixed way with other compounds.
10. organic electroluminescence device as claimed in claim 6, which is characterized in that be used alone a kind of selected from as right is wanted Structural formula 1-28's described in asking 4 is selected from using two or more such as claim 4 institute based on dibenzofurans compound, or simultaneously The structural formula 1-28 stated based on dibenzofurans compound.
CN201811023317.1A 2018-09-03 2018-09-03 One kind is based on dibenzofurans compound and application thereof and organic electroluminescence device Pending CN108864012A (en)

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