CN108976196A - A kind of aromatic amine compound of the spiro structure containing five-membered ring and application thereof and luminescent device - Google Patents
A kind of aromatic amine compound of the spiro structure containing five-membered ring and application thereof and luminescent device Download PDFInfo
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Abstract
The present invention provides a kind of aromatic amine compounds of spiro structure containing five-membered ring, have 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
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of aromatic amine chemical combination of the spiro structure containing five-membered ring
Object and application thereof 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 of spiro structure containing five-membered ring, are the change for having the following structure Formulas I
Close object:
Wherein, X is selected from O, S, Se；R1-R10Alkyl independently selected from hydrogen, deuterium, substitution or unsubstituted C1-C12 takes
The aryl of generation or unsubstituted C6-C30；Ar1-Ar2Aryl independently selected from substitution or unsubstituted C6-C30；L is selected from
Singly-bound or aryl.
Preferably, the aryl is selected from phenyl, diphenyl phenyl, naphthalene, phenyl napthyl, xenyl, terphenyl, three simultaneously
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.
It is further preferred that the aryl is further replaced by the alkyl of C1-C12.
Preferably, the aromatic amine compound of the spiro structure containing five-membered ring is the compound of following structural 1-114:
The aromatic amine compound of the spiro structure containing five-membered ring of the invention can be reacted by Buchwald-Hartwig and crow
Germania is anti-, suzkui should be prepared.
The aromatic amine compound of the spiro structure containing five-membered ring of the invention can be applied to organic electroluminescence device, solar energy
Battery, 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 the spiro structure containing five-membered ring 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 of the spiro structure containing five-membered ring is hole transmission layer.
The aromatic amine compound of the spiro structure containing five-membered ring as described in structural formula I is used alone, or mixed with other compounds
It closes and uses；The aromatic amine compound of the spiro structure containing five-membered ring as described in structural formula I can be used alone one such chemical combination
Object, can also be simultaneously using two or more the compound in structural formula I；It is used alone a kind of selected from structural formula 1-
The aromatic amine compound of 114 spiro structure containing five-membered ring, or contain five-membered ring selected from structural formula 1-114 using two or more simultaneously
The aromatic amine compound of spiro structure.
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 the aromatic amine compound of containing five-membered ring spiro structure of the present invention as described in structural formula I, have compared with
Good thermal stability, high-luminous-efficiency, high luminance purity.Organic electroluminescence device using compound production has electroluminescent hair
The advantage that light 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 intermediate A
The synthetic method of intermediate A
In flask, 2- (2- bromophenyl)-thiophene (10g, 42mol), anhydrous tetrahydro furan (100mL), in nitrogen is added
It is cooled to -78 degree under protection, the normal-butyl hexane solution (17mL, 42mmol) of 2.5M is slowly added dropwise, this temperature is kept to stir 2
Hour, then 2- bromine Fluorenone (10.8g, 42mol) is added dropwise toward this solution, it drips off, in room temperature reaction 2 hours, is slowly dripped toward reaction solution
The hydrochloric acid solution for adding 1N, is extracted with dichloromethane, dry, and 200mL acetic acid and 5mL concentrated hydrochloric acid is added in concentration in this crude product,
It is heated to reflux 5 hours, cooling, filtering, then is recrystallized with ethyl alcohol and tetrahydrofuran, is dry, obtain product 9.6g, yield 57%.
The synthetic method of other intermediates such as intermediate A, be all use 2- bromine Fluorenone as raw material, then with bromo-derivative
Reaction, specific such as table 1:
Table 1
Embodiment 8
The synthetic route of compound 15
In flask, it is added intermediate A (2g, 5mmol), biphenyl fluorenamine (1.8g, 5mmol), sodium tert-butoxide (1g,
10mmol), palladium acetate (0.1g), X-phos (0.3g), toluene (30mL) are heated to reflux 5 hours under nitrogen protection, cooling, remove
Solvent is removed, crude by column chromatography purifies to obtain 2.7g, yield 77%.
The synthetic method of other embodiments such as compound 1, be all use intermediate B as raw material, then with others
Amine reaction, specific such as table 2:
Table 2
Embodiment 20-31
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 3.
Comparative example 1 and 2
In addition to use NPB and HT1 replace respectively the compounds of this invention as hole mobile material other than, comparative example prepares device
Method is as embodiment 20-31.
3 experimental result of table
The structural formula of compound described in device is as follows:
From table 3 it can be seen that the aromatic amine compound of the spiro structure of the invention containing five-membered ring 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 of spiro structure containing five-membered ring, which is characterized in that be the compound for having the following structure Formulas I:
Wherein, X is selected from O, S, Se；R1-R10Alkyl independently selected from hydrogen, deuterium, substitution or unsubstituted C1-C12, replace or
The aryl of the unsubstituted C6-C30 of person；Ar1-Ar2Aryl independently selected from substitution or unsubstituted C6-C30；L is selected from singly-bound
Or aryl.
2. the aromatic amine compound of the spiro structure containing five-membered ring as described in claim 1, which is characterized in that the aryl is selected from benzene
Base, diphenyl phenyl, naphthalene, naphthylphenyl, xenyl, terphenyl, 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, dibenzothiophene
And dibenzofuran group.
3. the aromatic amine compound of the spiro structure containing five-membered ring as claimed in claim 2, which is characterized in that the aryl is further
Replaced by the alkyl of C1-C12.
4. the aromatic amine compound of the spiro structure containing five-membered ring as described in claim 1, which is characterized in that be following structural 1-
114 compound:
5. application of the aromatic amine compound of the spiro structure described in claim 1 containing five-membered ring 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
State at least one layer of aromatic amine compound containing the spiro structure containing five-membered ring as described in claim 1 in organic layer.
7. organic electroluminescence device as claimed in claim 6, which is characterized in that spiral shell containing five-membered ring described in claim 1
Layer where the aromatic amine compound of structure is hole transmission layer.
8. organic electroluminescence device as claimed in claim 6, which is characterized in that spiral shell containing five-membered ring described in claim 1
The aromatic amine compound of structure 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 of the spiro structure containing five-membered ring of structural formula 1-114 described in 4, or simultaneously using two or more selected from such as right
It is required that the aromatic amine compound of the spiro structure containing five-membered ring of structural formula 1-114 described in 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。
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111793001A (en) * | 2019-04-02 | 2020-10-20 | 材料科学有限公司 | Organic compound and organic electroluminescent element comprising same |
| CN112390789A (en) * | 2019-08-16 | 2021-02-23 | 南京高光半导体材料有限公司 | Electron transport material and organic electroluminescent device using same |
Citations (3)
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| CN106432181A (en) * | 2016-09-27 | 2017-02-22 | 上海道亦化工科技有限公司 | Compound containing pentacyclic ring screw structure and organic electroluminescence device |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111793001A (en) * | 2019-04-02 | 2020-10-20 | 材料科学有限公司 | Organic compound and organic electroluminescent element comprising same |
| CN111793001B (en) * | 2019-04-02 | 2023-12-22 | 材料科学有限公司 | Organic compound and organic electroluminescent element comprising same |
| CN112390789A (en) * | 2019-08-16 | 2021-02-23 | 南京高光半导体材料有限公司 | Electron transport material and organic electroluminescent device using same |
| CN112390789B (en) * | 2019-08-16 | 2022-05-13 | 南京高光半导体材料有限公司 | Electron transport material and organic electroluminescent device using same |
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Application publication date: 20181211 |