CN109053698A - A kind of aromatic amine compound and luminescent device containing dibenzofurans - Google Patents

A kind of aromatic amine compound and luminescent device containing dibenzofurans Download PDF

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CN109053698A
CN109053698A CN201811094415.4A CN201811094415A CN109053698A CN 109053698 A CN109053698 A CN 109053698A CN 201811094415 A CN201811094415 A CN 201811094415A CN 109053698 A CN109053698 A CN 109053698A
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aromatic amine
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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 a kind of aromatic amine luminophor containing dibenzofurans, has the following structure formula:The compound has preferable thermal stability, high-luminous-efficiency, high luminance purity, can be applied to organic electroluminescence device, organic solar batteries, 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, exciton barrier-layer, electron transfer layer, the at least one layer compound containing such as structural formula I in organic layer has the advantages that electroluminescent efficiency is good and excitation purity is excellent and the service life is long using the organic electroluminescence device that the compound makes.

Description

A kind of aromatic amine compound and luminescent device containing dibenzofurans
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of aromatic amine chemical combination containing dibenzofurans Object further relates to a kind of organic electroluminescence device.
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.
Organic electrophosphorescenpolymer phenomenon, breaches theoretical limitation of the organic electroluminescent quantum efficiency lower than 25%, and promotion is arrived 100% (Baldo M.A., Forrest S.R.Et al, Nature, 1998,395,151-154), application also greatly mention The high efficiency of organic electroluminescence device.Generally, electroluminescent phosphorescence needs commonly to be used as phosphorus using host-guest system technology The CBP (4,4'-bis (9-carbazolyl)-biphenyl) of light material of main part has efficient and high triplet energy level, when its work Based on material when, triplet energy state effectively can be transferred to object phosphorescent light-emitting materials from light emitting host material.But by It is easily transmitted and the characteristic of electronics difficulty flowing in the hole of CBP, so that the charge unbalance of luminescent layer, as a result reduces the effect of device Rate.
In organic electroluminescence device, the introducing of hole mobile material and injection material can be effectively reduced positive electricity Lotus is transferred to the ability of luminescent layer from anode, improves the efficiency and thermostabilization of device.Traditional hole-injecting material, such as copper Phthalocyanine (CuPc), degradation is slow, and preparation energy consumption is high, is unfavorable for environmental protection, and it can absorb light, influence device Efficiency.NPB etc. original hole mobile material, thermal stability is poor, also largely influences device lifetime.Thus, it needs Develop the electroluminescent organic material of efficient stable.
Summary of the invention
The present invention provides a kind of aromatic amine compounds containing dibenzofurans, are the chemical combination for having the following structure Formulas I Object:
Wherein, Ar1Triaromatic amine base, substitution or unsubstituted C12- selected from substitution or unsubstituted C18-C30 The carbazyl of C30；Ar2And Ar3Aryl, substitution or unsubstituted independently selected from substitution or unsubstituted C6-C30 The carbazyl of the triaromatic amine base of C18-C30, substitution or unsubstituted C12-C30.
Preferably, the aryl is selected from phenyl, diphenyl, naphthalene, phenyl napthyl, xenyl, terphenyl, three acenes Base, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, acenaphthenyl, acenaphthylene base, (9,9- dialkyl group) fluorenyl, (9,9- bis- replace or not Substituted aryl) fluorenyl, dibenzothiophene and dibenzofuran group.
It is further preferred that the aryl is further replaced by the alkyl of C1-C12.
Preferably, the aromatic amine compound containing dibenzofurans is the compound of following structural 1-40:
Aromatic amine compound containing dibenzofurans of the invention can be reacted by Buchwald-Hartwig and Wu Er Graceful anti-, suzkui should be prepared.
Aromatic amine compound containing dibenzofurans of the invention can be applied to organic electroluminescence device, solar-electricity Pond, Organic Thin Film Transistors 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, exciton barrier-layer, electron transfer layer Layer, at least one layer of aromatic amine compound containing dibenzofurans containing as described in structural formula I in the organic layer.
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 compound containing dibenzofurans is hole transmission layer.
The aromatic amine compound containing dibenzofurans as described in structural formula I is used alone, or mixes with other compounds It uses；The aromatic amine compound containing dibenzofurans as described in structural formula I can be used alone one such compound, It can be simultaneously using two or more the compound in structural formula I；A kind of containing selected from structural formula 1-40 is used alone The aromatic amine compound of dibenzofurans, or the two or more fragrance containing dibenzofurans selected from structural formula 1-40 are used simultaneously Amine compounds.
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, 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 compound containing dibenzofurans of the present invention as described in structural formula I, has preferable Thermal stability, high-luminous-efficiency, high luminance purity.Organic electroluminescence device using compound production has electroluminescent The advantage that 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 be glass substrate, and 120 be anode, and 130 be hole injection layer, and 140 be hole transmission layer, and 150 be hair Photosphere, 160 be electron transfer layer, and 170 be electron injecting layer, and 180 be 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 6
The synthetic method of intermediate 6-1
In flask, the bromo- 4- aminodiphenyl of 1- and furans (4g, 15.3mmol), 9- phenyl -3- carbazyl benzene are sequentially added Boric acid (4.4g, 15.3mmol), potassium carbonate (4g, 30mmol), tetra-triphenylphosphine palladium (0.1g), tetrahydrofuran (40mL), water (20mL) is heated to reflux 5 hours under nitrogen protection, cooling, is extracted with dichloromethane, dry, concentration, crude by column chromatography Purifying obtains 4.2g, yield 61%.
The synthetic method of compound 6
It in flask, sequentially adds intermediate 6-1 (3g, 7mmol), 4- bromo biphenyl (4.1g, 18mmol), sodium tert-butoxide (2.1g, 21mmol), palladium acetate (0.1g), X-phos (0.3g), toluene (30mL) are heated to reflux 5 hours under nitrogen protection, cold But, solvent is removed, crude by column chromatography purifies to obtain 3.7g, yield 72%.
Embodiment 2
The synthesis of compound 20
The synthetic method of intermediate 20-1
Its synthetic method is as the synthesis of intermediate 6-1, yield 80%.
The synthetic method of compound 20
For its synthetic method as the synthesis of compound 6, raw materials used is intermediate 20-1, yield 61%.
Embodiment 3
The synthetic route of compound 22
The synthetic method of intermediate 22-1
Its synthetic method is as the synthesis of intermediate 6-1, yield 69%.
The synthetic method of compound 22
For its synthetic method as the synthesis of compound 6, raw materials used is intermediate 22-1, yield 73%.
Embodiment 4
The synthetic route of compound 33
The synthetic method of intermediate 33-1
Its synthetic method is such as intermediate 6-1, yield 77%.
The synthetic method of compound 33
Its synthetic method and the synthesis of compound 6 are same, and raw materials used is intermediate 33-1, yield 67%.
Embodiment 5
The synthetic route of compound 34
Its synthetic method replaces 4- bromo biphenyl, yield as the synthesis of compound 33, with 9,9- dimethyl -2- bromine fluorenes 69%.
Embodiment 6-10
The preparation of organic electroluminescence device
OLED is prepared using the compound of embodiment
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, the PEDOT:PSS (Polyglycolic acid fibre-is poly- (styrene sulfonate)) of spin coating 45nm thickness is on ITO It is 30 minutes dry at 130,150 DEG C of hole injection layer.
Then, the compounds of this invention of 40nm thickness is deposited on hole injection layer as hole mobile material 140.
Then, the luminescent layer 150 of 30nm thickness is deposited on electronic barrier layer, wherein luminescent material based on CBP, and with The Ir (ppy) that weight ratio is 8%3Guest materials is adulterated as phosphorescence.
Then, the TMPYPB of 40nm thickness is deposited on the light-emitting layer as electron transfer layer 160.
Finally, vapor deposition 1nm LiF is electron injecting layer 170 and 80nm Al as device cathodes 180.
Prepared device (structural schematic diagram is shown in Fig. 1) with Photo Research PR650 spectrometer measure 100mA/cm2Current density under external quantum efficiency be such as table 1.
Comparative example 1
In addition to use NPB replace the compounds of this invention as hole mobile material other than, comparative example prepares the method and reality of device It is the same to apply a 6-10.
1 experimental result of table
Embodiment Compound Current efficiency (100%) Luminescent color
6 6 8.1 Green light
7 20 8.4 Green light
8 22 8.2 Green light
9 33 8.3 Green light
10 34 7.9 Green light
Comparative example 1 NPB 6.1 Green light
The structural formula of compound described in device is as follows:
As it can be seen from table 1 the triaromatic amine compound of the invention containing dibenzofurans is used for organic electroluminescence Part can reduce operating voltage, improve device efficiency, be the hole mobile material with excellent performance.As described above, of the invention Compound there is high stability, the organic electroluminescence device of preparation has high efficiency and optical purity.
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. a kind of aromatic amine compound containing dibenzofurans, which is characterized in that be the compound for having the following structure Formulas I:
Wherein, Ar1Triaromatic amine base, substitution or unsubstituted C12-C30 selected from substitution or unsubstituted C18-C30 Carbazyl；Ar2And Ar3Aryl, substitution or unsubstituted C18-C30 independently selected from substitution or unsubstituted C6-C30 Triaromatic amine base, substitution or unsubstituted C12-C30 carbazyl.
2. as described in claim 1 containing the aromatic amine compound of dibenzofurans, which is characterized in that the aryl is selected from benzene Base, diphenyl, naphthalene, naphthylphenyl, xenyl, terphenyl, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, Acenaphthenyl, acenaphthylene base, (9,9- dialkyl group) fluorenyl, (9,9- bis- replace or unsubstituted aryl) fluorenyl, dibenzothiophene and Dibenzofuran group.
3. as claimed in claim 2 containing the aromatic amine compound of dibenzofurans, which is characterized in that the aryl further by The alkyl of C1-C12 replaces.
4. as described in claim 1 containing the aromatic amine compound of dibenzofurans, which is characterized in that be following structural 1-40 Compound:
5. application of the aromatic amine compound described in claim 1 containing dibenzofurans 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, exciton barrier-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 containing the aromatic amine compound of dibenzofurans in organic layer.
7. organic electroluminescence device as claimed in claim 6, which is characterized in that furan containing dibenzo described in claim 1 Layer where the aromatic amine compound muttered is hole transmission layer.
8. organic electroluminescence device as claimed in claim 6, which is characterized in that furan containing dibenzo described in claim 1 The aromatic amine compound muttered is used alone, or is used in mixed way with other compounds.
9. organic electroluminescence device as claimed in claim 6, which is characterized in that be used alone a kind of selected from such as claim The aromatic amine compound containing dibenzofurans of structural formula 1-40 described in 4, or wanted simultaneously using two or more selected from such as right The aromatic amine compound containing dibenzofurans of structural formula 1-40 described in asking 4.
10. organic electroluminescence device as claimed in claim 6, which is characterized in that the overall thickness of the organic layer is 1- 1000nm。
CN201811094415.4A 2018-09-19 2018-09-19 A kind of aromatic amine compound and luminescent device containing dibenzofurans Pending CN109053698A (en)

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CN111718367A (en) * 2020-07-28 2020-09-29 吉林奥来德光电材料股份有限公司 Organic luminescent material and preparation method and application thereof
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CN111138393A (en) * 2018-11-02 2020-05-12 昱镭光电科技股份有限公司 Arylamine compound and organic electroluminescent device using the same
CN111138393B (en) * 2018-11-02 2023-04-07 昱镭光电科技股份有限公司 Arylamine compound and organic electroluminescent device using the same
CN110256415A (en) * 2019-06-26 2019-09-20 上海天马有机发光显示技术有限公司 A kind of compound, light extraction material, organic photoelectric device and electronic equipment
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CN112745285A (en) * 2019-10-31 2021-05-04 昱镭光电科技股份有限公司 Aminodibenzofuran compound and organic electroluminescent device thereof
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EP4201930A4 (en) * 2020-08-13 2024-07-31 Lt Mat Co Ltd Heterocyclic compound, organic light-emitting device comprising same, and composition for organic material layer of organic light-emitting device
CN116082318A (en) * 2023-04-03 2023-05-09 吉林奥来德光电材料股份有限公司 Blue light luminescent auxiliary material, preparation method thereof and organic electroluminescent device
CN116375694A (en) * 2023-05-31 2023-07-04 吉林奥来德光电材料股份有限公司 Benzonaphthofuran compound and preparation method and application thereof
CN116375694B (en) * 2023-05-31 2023-09-15 吉林奥来德光电材料股份有限公司 Benzonaphthofuran compound and preparation method and application thereof

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Application publication date: 20181221