CN107266346A - A kind of benzidine class organic electroluminescent compounds and its organic electroluminescence device - Google Patents
A kind of benzidine class organic electroluminescent compounds and its organic electroluminescence device Download PDFInfo
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Abstract
The invention provides a kind of benzidine class organic electroluminescent compounds, it has following structure：The compound has preferable heat endurance, and high-luminous-efficiency, high luminance purity, low driving voltage can be used for making organic electroluminescence device, applied to organic solar batteries, perovskite battery, 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, exciton barrier-layer, electron transfer layer, at least one layer of compound comprising just like structural formula I in organic layer, the organic electroluminescence device has the advantages that electroluminescent efficiency is good and excitation is excellent and long lifespan.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of benzidine class electroluminescent organic material
And its organic electroluminescence device, belong to organic electroluminescence device display technology field.
Background technology
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 from, a classical three layer organic electroluminescence device includes hole transmission layer, luminescent layer
And electron transfer layer.The hole produced by anode through hole transmission layer with the electronics that is produced by negative electrode through combined with electron transfer layer
Luminescent layer formation exciton, then lights.Organic electroluminescence device can be adjusted as desired by the material of luminescent layer is changed
The light of the various needs of section transmitting.
Organic electroluminescence device is as a kind of new Display Technique, with self-luminous, wide viewing angle, low energy consumption, efficiency
High, thin, rich 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, can be applied on flat-panel monitor and a new generation's illumination, can also conduct
LCD backlight.
Since invention at the bottom of 1980s, organic electroluminescence device has industrially been applied, such as
As screens such as camera and mobile phones, but current OLED is low due to efficiency, and it is wider that the factor such as service life is short restricts 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.Applying voltage-operated additionally, due to OLED
When, Joule heat can be produced so that organic material is easily crystallized, 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.
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 positive pole, improves the efficiency of device and thermally-stabilised.Traditional hole-injecting material, such as copper
Phthalocyanine (CuPc), degraded is slow, prepares power consumption height, is unfavorable for environmental protection, and it can absorb light, influence device
Efficiency.Hole mobile material original NPB etc., heat endurance is poor, also largely influences device lifetime.Thus, need
Develop the electroluminescent organic material of efficient stable.
The content of the invention
The invention provides a kind of benzidine class organic electroluminescent compounds, it is the change with following structural formula I
Compound：
Wherein, Ar1And Ar2Independently selected from substitution or unsubstituted C6-C30 aryl, substitution or unsubstituted
C3-C30 heteroaryl, two aromatic aminos of substitution or unsubstituted C1-C30, the three of substitution or unsubstituted C1-C30
Aromatic amino, carbazyl；
R1And R2Independently selected from hydrogen, C1-C12 alkyl, C1-C8 alkoxy, substitution or unsubstituted C6-C30
The heteroaryl of aryl, substitution or unsubstituted C3-C30；
L1Substitution or unsubstituted aryl selected from C6-C30；
L2And L3Independently selected from singly-bound or sky.
Preferably, Ar1And Ar2Independently selected from phenyl, naphthyl, xenyl, three and phenyl, C6-C30 aryl substitution or
Person C1-C4 alkyl-substituted carbazyl, indyl, carbazole indyl, fluorenes carbazyl, anthryl, phenanthryl, pyrenyl, perylenes base, fluoranthene
Base, (9,9- dialkyl group) fluorenyl, (9,9- bis- replaces or unsubstituted aryl) fluorenyl, 9,9- Spirofluorene-based, triaromatic amine base or
Substitution or unsubstituted dibenzofuran group, or more aryl and heteroaryl further replaced by C1-12 alkyl；
R1And R2Independently selected from hydrogen, methyl, ethyl, propyl group, isopropyl, butyl, phenyl, aminomethyl phenyl or xenyl；
L1Selected from phenyl or naphthyl.
It is further preferred that described benzidine class organic electroluminescent compounds are following structural 1-34 chemical combination
Thing：
The benzidine class organic electroluminescent compounds of the present invention can be applied in organic electroluminescence device, You Jitai
Positive energy battery, perovskite battery, 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
Comprising at least one layer in luminescent layer, hole injection layer, hole transmission layer, exciton barrier-layer, electron transfer layer, wherein described have
At least one layer contains the organic electroluminescent compounds as described in structural formula I in machine layer：
Wherein R1With R2、Ar1With Ar2、L1With L2And L3It is defined as described above.
Wherein organic layer is hole transmission layer and luminescent 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, luminescent layer, electron transfer layer, electron injecting layer and exciton
Barrier layer；
Or organic layer is hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and exciton barrier-layer；
Or organic layer is hole transmission layer, luminescent layer, electron injecting layer and exciton barrier-layer.
Preferably, wherein the layer where benzidine class organic electroluminescent compounds as described in structural formula I is hole
Transport layer.
Preferably, wherein the benzidine class organic electroluminescent compounds as described in structural formula I are structural formula 1-34
Compound.
When benzidine class organic electroluminescent compounds as described in structural formula I are used for luminescent device preparation, Ke Yidan
Solely use, can also be used in mixed way with other compounds；Benzidine class organic electroluminescent compounds as described in structural formula I
A kind of compound therein is can be used alone, 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 is that the organic electroluminescence device includes sun
Contain structural formula I in pole, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, its hole-transporting layer
Compound；It is further preferred that the compound that the compound in hole transmission layer is structural formula 1-34.
The gross thickness of the organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
The organic electroluminescence device of the present invention is when having structural formula I compound using the present invention, and can arrange in pairs or groups makes
With other materials, such as in hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and exciton barrier-layer
It is medium, 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, can effectively be transferred to hole on luminescent layer from anode.There is compound described in structural formula I except above-mentioned
Outside, other small molecules and macromolecular organic compound, including but not limited to carbazole compound, triaromatic amine can also be included
Compound, benzidine compound, compound of fluorene class, phthalocyanine-like compound, the miscellaneous triphen of six cyano group six
(hexanitrilehexaazatriphenylene), the cyanogen dimethyl-parabenzoquinone (F4- of 2,3,5,6- tetra- fluoro- 7,7', 8,8'- tetra-
TCNQ), PVK, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of the organic electroluminescence device of the present invention, with the good characteristics of luminescence, can be adjusted as needed
The scope of visible ray.In addition to can be containing compound of fluorene class of the invention, following compound can also be contained, including but not limit
In naphthalene compounds, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance class compound,Class compound, phenol piperazine class compound, anthracene class
Compound, pentacene class compound, perylene classes compound, two aromatic ethylene class compounds, triphenylamine ethylene compounds, amine chemical combination
Thing, carbazole compound, benzimidazoles compound, furfuran compound, metal organic fluorescence complex compound, metal Phosphorescent
Complex compound (such as Ir, Pt, Os, Cu), polyvinylcarbazole, poly-organosilicon compound, polythiophene organic polymer luminescent material, it
Can be used alone, can also a variety of mixtures use.
The Organic Electron Transport Material requirement of organic electroluminescence device of the present invention has good electronic transmission performance, energy
It is enough effectively electronics from cathode transport to luminescent layer in, with very big electron mobility.Following compound can be selected, but
It is not limited to this：Oxa- oxazole, thiazole compound, triazole compound, three nitrogen piperazine class compounds, triazine class chemical combination
Thing, 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 by the electron injecting layer of organic electroluminescence device of the present invention 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 or alkaline-earth metal
Metal complex, can select 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 can also mixture use, can also be used cooperatively with other electroluminescent organic materials.
Each layer of organic layer in the organic electroluminescence device of the present 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.It can make for metal motor
Prepared with vapour deposition method or sputtering method.
Device experimental shows, benzidine class organic electroluminescent compounds of the present invention as described in structural formula I, with compared with
Good heat endurance, high-luminous-efficiency, high luminance purity, low driving voltage.Using the benzidine class organic electroluminescent chemical combination
The organic electroluminescence device that thing makes has the advantages that electroluminescent efficiency is good and excitation is excellent and long lifespan.
Brief description of the drawings
Fig. 1 is a kind of organic electroluminescence device structural representation of the 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. 2 is the current density and external quantum efficiency graph of a relation of the organic electroluminescence device of embodiments of the invention.
Embodiment
In order to describe the present invention in more detail, especially exemplified by example below, but not limited to this.
Embodiment 1
The synthesis of compound 1
Intermediate 1-1 synthesis
In round-bottomed flask, indoles (10g, 85mmol) is put into and to bromo-iodobenzene (24g, 85mmol), potassium hydroxide
(7.1g, 128mmol), cuprous iodide (1g) and Phen (1g), ortho-xylene (200mL), nitrogen protection, at 180 DEG C
Heating, is stirred at reflux 8 hours, cools down, and by washing, after dichloromethane extraction, is spin-dried for, and obtained by column chromatography separating purification
Product 19g, yield is 82%.
Intermediate 1-2 synthesis
In round-bottomed flask, input intermediate 1-1 (12g, 44mmol) and 9,9- dimethyl -2- fluorenamines (9.3g,
44mmol), sodium tert-butoxide (6.5g, 66mmol), palladium (0.3g) and x-phos (0.6g), add 200mL toluene and make solvent,
Nitrogen is protected, and is heated, is stirred at reflux 8 hours at 150 DEG C, and reaction is complete, cooling, by washing, after dichloromethane extraction, rotation
It is dry, and product 11g is obtained by column chromatography separating purification, yield is 65%.
Intermediate 1-3 synthesis
Synthetic method is with intermediate 1-1 synthesis, raw materials used for intermediate 1-2 and to bromo-iodobenzene, yield is
77%.The synthesis of compound 1
In 100mL round-bottomed flasks, input intermediate 1-3 (1.6g, 2.9mmol) and 4- diphenylamines phenyl boric acid (0.9g,
3.1mmol), Anhydrous potassium carbonate (0.8g, 5.8mmol), adds 10mL water and 20mL tetrahydrofurans, and add appropriate catalysis
Agent --- tetra-triphenylphosphine palladium, nitrogen protection, heats at 120 DEG C, is stirred at reflux 5 hours, and reaction is complete, cooling, by water
Wash, after dichloromethane extraction, be spin-dried for, and by column chromatography separating purification product 1.3g, yield is 64%.
Embodiment 2-8 synthesis is raw materials used and yield such as following table, and synthetic method is with the synthesis of compound 1.
Embodiment 9
The synthesis of compound 27
Intermediate 27-1 synthesis
Synthetic method is with as intermediate 1-3, in addition to replacing to bromo-iodobenzene with a bromo-iodobenzene, and yield is 79%.
The synthesis of compound 27
Synthetic method is with as compound 1, in addition to replacing intermediate 1-3 with intermediate 27-1, and yield is 74%.
Embodiment 10
The synthesis of compound 32
Synthetic method is with the synthesis of compound 1, raw materials used is the boric acid of intermediate 27-1 and 9- phenyl carbazole -3, production
Rate is 83%.
Embodiment 11-20
The preparation of organic electroluminescence device
OLED is prepared using the compound of embodiment.
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 45nm on ITO:PSS (Polyglycolic acid fibre-poly- (styrene sulfonate)) is
Dried 30 minutes at 130,150 DEG C of hole injection layer；
Then, the thick the compounds of this invention of 40nm is deposited on hole injection layer as hole mobile material 140,
Then, the thick luminescent layers 150 of 30nm are deposited on electronic barrier layer, wherein, the compounds of this invention is luminous for main body
Material, and with 8% weight than Ir (ppy)3It is used as phosphorescence doping guest materials.
Then, the thick TMPYPB of 40nm are deposited on luminescent layer and are used as electron transfer layer 160.
Finally, evaporation 1nm LiF are that electron injecting layer 170 and 80nm Al are used as device cathodes 180.
Prepared device (structural representation is shown in Fig. 1) measured with Photo Research PR650 spectrometers
100mA/cm2Current density under external quantum efficiency be such as table 1 and Fig. 2.
Comparative example 1
Device prepared by comparative example is with embodiment 11-20 device preparation methods, except replacing chemical combination of the present invention with NPB
Thing as hole mobile material outside.
Table 1
The structural formula of compound described in device is as follows：
As can be seen from the table, new organic materials of the invention are used for organic electroluminescence device, can reduce work
Voltage, improves device efficiency, is the phosphorescent light body material with premium properties.As described above, the compound of the present invention has height
Stability, the organic electroluminescence device of preparation has high efficiency and optical purity.
Preferred embodiment of the invention described in detail above.It should be appreciated that one of ordinary skill in the art without
Need creative work just can make many modifications and variations according to the design of the present invention.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 scheme, all should be in the protection domain being defined in the patent claims.
Claims (8)
1. a kind of benzidine class organic electroluminescent compounds, it is characterised in that be the compound with following structural formula I：
Wherein, Ar1And Ar2Independently selected from substitution or unsubstituted C6-C30 aryl, substitution or unsubstituted C3-C30
Heteroaryl, two aromatic aminos of substitution or unsubstituted C1-C30, substitution or unsubstituted C1-C30 triaromatic amine
Base, carbazyl；
R1And R2Independently selected from hydrogen, C1-C12 alkyl, C1-C8 alkoxy, substitution or unsubstituted C6-C30 virtue
The heteroaryl of base, substitution or unsubstituted C3-C30；
L1Substitution or unsubstituted aryl selected from C6-C30；
L2And L3Independently selected from singly-bound or sky.
2. benzidine class organic electroluminescent compounds as claimed in claim 1, it is characterised in that Ar1And Ar2Independently
Selected from phenyl, naphthyl, xenyl, three and phenyl, C6-C30 aryl substitution or C1-C4 alkyl-substituted carbazyl, Yin
Diindyl base, carbazole indyl, fluorenes carbazyl, anthryl, phenanthryl, pyrenyl, perylenes base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (9,9- bis-
Substitution or unsubstituted aryl) fluorenyl, 9,9- Spirofluorene-based, triaromatic amine base or substitution or unsubstituted dibenzofurans
Base, or more aryl and heteroaryl further replaced by C1-12 alkyl；
R1And R2Independently selected from hydrogen, methyl, ethyl, propyl group, isopropyl, butyl, phenyl, aminomethyl phenyl or xenyl；
L1Selected from phenyl or naphthyl.
3. benzidine class organic electroluminescent compounds as claimed in claim 1, it is characterised in that it is following structural
1-34 compound：
4. a kind of organic electroluminescence device, the device includes anode, negative electrode and organic layer, organic layer includes luminescent layer, hole
At least one layer in implanted layer, hole transmission layer, exciton barrier-layer, electron transfer layer, it is characterised in that in the organic layer extremely
Rare one layer contains the benzidine class organic electroluminescent compounds as described in any one in claims 1 to 3.
5. organic electroluminescence device as claimed in claim 4, it is characterised in that the benzidine class as described in structural formula I
Layer where organic electroluminescent compounds is hole transmission layer.
6. organic electroluminescence device as claimed in claim 4, it is characterised in that the benzidine class as described in structural formula I
Organic electroluminescent compounds are structural formula 1-34 compound.
7. organic electroluminescence device as claimed in claim 4, it is characterised in that the benzidine class as described in structural formula I
A kind of compound therein is used alone in organic electroluminescent compounds, or uses the two or more changes in structural formula I simultaneously
Compound.
8. organic electroluminescence device as claimed in claim 4, it is characterised in that organic electroluminescence device organic layer it is total
Thickness is 1-1000nm.
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| CN201710676754.2A CN107266346A (en) | 2017-08-09 | 2017-08-09 | A kind of benzidine class organic electroluminescent compounds and its organic electroluminescence device |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109232492A (en) * | 2018-10-18 | 2019-01-18 | 长春海谱润斯科技有限公司 | A kind of aromatic amine derivant and its organic electroluminescence device |
| CN114874231A (en) * | 2021-02-05 | 2022-08-09 | 上海和辉光电股份有限公司 | Organic electroluminescent compound and application thereof |
-
2017
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109232492A (en) * | 2018-10-18 | 2019-01-18 | 长春海谱润斯科技有限公司 | A kind of aromatic amine derivant and its organic electroluminescence device |
| CN114874231A (en) * | 2021-02-05 | 2022-08-09 | 上海和辉光电股份有限公司 | Organic electroluminescent compound and application thereof |
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Application publication date: 20171020 |