CN105622581B - Compound and its organic electroluminescence device containing quinoxaline group - Google Patents
Compound and its organic electroluminescence device containing quinoxaline group Download PDFInfo
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Abstract
The present invention provides a kind of organic electroluminescent compounds containing quinoxaline group, the compound has preferable thermal stability, high-luminous-efficiency, high luminance purity, it can be used for making organic electroluminescence device, be applied to organic solar batteries, Organic Thin Film Transistors or organophotoreceptorswith field.The present invention also provides a kind of organic electroluminescence devices, it includes anode, cathode and organic layer, organic layer includes one layer or more in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, at least one layer of compound comprising just like structural formula I in organic layer.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of organic electroluminescence hair containing quinoxaline group
Optical compounds and its organic electroluminescence device belong to organic electroluminescence device field of display technology.
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.
Speed in OLED material, due to the speed of most electroluminescent organic material transporting holes than transmitting electronics
Fastly, it be easy to cause the electrons and holes quantity of luminescent layer uneven, the efficiency of such device is with regard to relatively low.Three (8-hydroxyquinolines)
Aluminium (Alq3) since the invention, it has been extensively studied, but still very as electron transport material its electron mobility
Intrinsic characteristic that is low, and itself can degrading, in using its device as electron transfer layer, it may appear that the case where voltage declines,
Simultaneously as lower electron mobility, so that a large amount of hole enters Alq3In layer, excessive hole is with non-luminescent shape
Formula radiation energy, and when as electron transport material, due to the characteristic of its green light, above it is restricted in application.Cause
This, organic electroluminescence device is widely used in development stability and the electron transport material with larger electron mobility
With great value.
Summary of the invention
Present invention firstly provides a kind of organic electroluminescent compounds containing quinoxaline group, to have the following structure
The compound of Formulas I:
Wherein, Ar1And Ar2It is separately selected from C1-C8 alkyl, C1-C8 alkoxyl, the substitution of C6-C30 or does not take
The substitution of the aryl, C3-C30 in generation unsubstituted contains one or more heteroatomic heteroaryl；Ar3Selected from C3-C60
Substitution or it is unsubstituted have one or more heteroatomic heteroaryl.
Preferably, Ar1And Ar2Separately it is selected from phenyl, xenyl, naphthalene, pyridyl group, quinolyl, pyridyl group benzene
Base, isoquinolyl, quinolyl phenyl；The above group can further be replaced by the alkyl of C1-C10 or alkoxy.
Preferably, Ar3Selected from benzimidazole, pyridyl group, pyrimidine radicals, quinolyl, isoquinolyl, triazine radical, pyrrole radicals, furan
It mutters base, thiazolyl, quinazolyl, triazol radical, benzothiazolyl, diazosulfide base, 1,2,4- triazolyl.
It is further preferred that the organic electroluminescent compounds of the invention containing quinoxaline group are following structural 1-
30 compound:
Organic electroluminescent compounds containing quinoxaline group of the invention can apply organic electroluminescence device,
Organic solar batteries, 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
Comprising one layer in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer with
On, wherein at least one layer organic electroluminescent containing quinoxaline group contained as described in structural formula I in the organic layer
Compound:
Wherein Ar1-Ar3It is defined as described above.
Wherein organic layer is luminescent layer and electron transfer layer；
Or organic layer is luminescent layer, hole injection layer, hole transmission layer and electron transfer layer；
Or organic layer is luminescent layer, hole injection layer, hole transmission layer, electron transfer layer and electron injecting layer；
Or organic layer is luminescent layer, hole injection layer, hole transmission layer, electron transfer layer, electron injecting layer and blocking
Layer；
Or organic layer is luminescent layer, hole transmission layer, electron transfer layer, electron injecting layer and barrier layer；
Or organic layer is luminescent layer, hole transmission layer, electron injecting layer and barrier layer.
Preferably, layer where the organic electroluminescent compounds containing quinoxaline group as described in structural formula I is electronics
Transport layer and/or electron injecting layer.
Preferably, the organic electroluminescent compounds containing quinoxaline group as described in structural formula I are structural formula 1-30
Compound.
When the organic electroluminescent compounds containing quinoxaline group as described in structural formula I are prepared for luminescent device,
It can be used alone, can also be used in mixed way with other compounds；The Organic Electricity containing quinoxaline group as described in structural formula I
Electro luminescent compounds can be used alone one such compound, can also be simultaneously using two or more in structural formula I
Compound.
Organic electroluminescence device of the invention, further preferred mode are that the organic electroluminescence device includes sun
Pole, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and cathode, wherein electron transfer layer and/or electron injection
Compound containing structural formula I in layer；It is further preferred that containing structural formula 1- in electron transfer layer and/or electron injecting layer
30 compound.
In organic electroluminescence device of the invention, it can also be also served as when Compounds of structural formula I is as electron transfer layer
Electron injecting layer.
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.It may include that other small molecules and macromolecule are organic
Compound, including but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanine
Class compound, the miscellaneous triphen (hexanitrilehexaazatriphenylene) of six cyano six, 2,3,5,6- tetra- fluoro- 7,7', 8,
Tetra- cyanogen dimethyl-parabenzoquinone (F4-TCNQ) of 8'-, 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.Following compound, including but not limited to naphthalene compounds, pyrene compound, fluorenes class chemical combination can be contained
Object, bends class compound, glimmering anthracene compound, anthracene compound, pentacene class compound, class compound, two at luxuriant and rich with fragrance class compound
Aromatic ethylene class compound, triphenylamine ethylene compounds, aminated compounds, carbazole compound, benzimidazoles compound, furan
Class of muttering compound, metal organic fluorescence complex compound, metal Phosphorescent complex compound (such as Ir, Pt, Os, Cu, Au), polyethylene click
The organic polymer luminescent materials such as azoles, poly-organosilicon compound, polythiophene, they can be used alone, and a variety of can also mix
Object uses.
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.Except of the invention has structural formula I
Outside compound, it is also an option that the following compound of collocation, but not limited to this: oxa- oxazole, thiazole compound, three nitrogen
Azole compounds, triazine class compound, quinoline class compound, phenodiazine anthracene compound, contain sila at three nitrogen piperazine class compounds
Cyclics, quinolines, ferrosin class compound, metallo-chelate (such as Alq3, 8-hydroxyquinoline lithium), fluorine replace
Benzene-like compounds, 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, except it is of the invention there is Compounds of structural formula I in addition to, be mainly selected from the compound of alkali metal or alkali metal, or be selected from alkaline earth
The compound or alkali metal complex of metal or alkaline-earth metal, can choose following compound, but not limited to this: alkali gold
Category, alkaline-earth metal, rare earth metal, the oxide of alkali metal or halide, the oxide of alkaline-earth metal or halide, rare earth
The organic complex of the oxide or halide of metal, alkali metal or alkaline-earth metal；Preferably lithium, lithium fluoride, lithia,
Lithium nitride, 8-hydroxyquinoline lithium, caesium, cesium carbonate, 8-hydroxyquinoline caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate,
Magnesia, these compounds, which can be used alone, to be used with mixture, can also match with other electroluminescent organic materials
It closes and uses.
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 organic electroluminescent compounds containing quinoxaline group of the present invention as described in structural formula I,
With preferable thermal stability, high-luminous-efficiency, high luminance purity.The organic electroluminescence made of the organic electroluminescent compounds
Luminescent device has the advantages that electroluminescent efficiency is good and excitation purity is excellent and the service life is long.
Detailed description of the invention
Fig. 1 is the hydrogen nuclear magnetic spectrogram of compound 2；
Fig. 2 is the hydrogen nuclear magnetic spectrogram of compound 7；
Fig. 3 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 synthesis of compound 2
The synthesis of intermediate 2-1
In flask, 4- bromine o-phenylenediamine (18.6g, 0.1mol), benzil (21g, 0.1mol) and acetic acid is added
(200ml) is heated to 90 degree and reacts 5 hours, and cooling, filtering, filter cake ethyl alcohol recrystallization obtains product 28g, yield 78%.
The synthesis of intermediate 2-2
In flask, intermediate 2-1 (18g, 50mmol), connection boric acid pinacol ester (15.2g, 60mmol), acetic acid is added
Potassium (9.8g, 100mmol), dioxane (200ml) and palladium diphenyl phosphine dichloride (1g) are heated to reflux 5 under nitrogen protection
Hour, cooling, concentration, crude product obtains product 15.3g, yield 75% through column chromatographic purifying.
The synthesis of intermediate 2-3
In three-necked flask, 2,4- dichloroquinazoline (6g, 30mmol), biphenylboronic acid (6g, 30mmol), potassium carbonate is added
(8.3g, 60mmol), tetra-triphenylphosphine palladium (0.3g), tetrahydrofuran (60ml) and water (20ml), heating 5 is small under nitrogen protection
When, cooling, filtering, crude product uses tetrahydrofuran and ethyl alcohol recrystallization again, obtains product 7.6g, yield 80%.
The synthesis of compound 2
In three-necked flask, intermediate 2-2 (2g, 4.9mmol), intermediate 2-3 (1.6g, 4.9mmol), potassium carbonate is added
(1.1g, 10mmol), tetra-triphenylphosphine palladium (0.1g), tetrahydrofuran (50ml) and water (20ml), heating 5 is small under nitrogen protection
When, it is cooling, it is extracted with dichloromethane, dries, filters, crude product obtains product 2.5g, yield 91%, hydrogen through column chromatographic purifying
Nuclear magnetic spectrogram is as shown in Figure 1.
Embodiment 2
The synthesis of compound 7
In three-necked flask, intermediate 2-2 (2g, 4.9mmol), 2- (4- bromophenyl) -1- phenyl -1H- benzo miaow is added
Azoles (1.7g, 4.9mmol), potassium carbonate (1.1g, 10mmol), tetra-triphenylphosphine palladium (0.1g), tetrahydrofuran (50ml) and water
(20ml) is heated 5 hours under nitrogen protection, cooling, is extracted with dichloromethane, is dried, filtered, crude product is obtained through column chromatographic purifying
To product 2.3g, yield 85%, hydrogen nuclear magnetic spectrogram is as shown in Figure 2.
Embodiment 3
The synthesis of compound 17
In three-necked flask, intermediate 2-2 (2g, 4.9mmol), 2- (4- bromophenyl) -4,6- diphenyl -1,3,5- is added
Triazine (1.9g, 4.9mmol), potassium carbonate (1.1g, 10mmol), tetra-triphenylphosphine palladium (0.1g), tetrahydrofuran (50ml) and water
(20ml) is heated 5 hours under nitrogen protection, cooling, is extracted with dichloromethane, is dried, filtered, crude product is obtained through column chromatographic purifying
To product 1.9g, yield 67%.
Embodiment 4
The synthesis of compound 19
In three-necked flask, intermediate 2-2 (2g, 4.9mmol), 3- (4- bromophenyl) -4,5- diphenyl -4H-1 is added,
2,4- triazole (1.8g, 4.9mmol), potassium carbonate (1.1g, 10mmol), tetra-triphenylphosphine palladium (0.1g), tetrahydrofuran (50ml)
With water (20ml), heat 5 hours under nitrogen protection, it is cooling, it is extracted with dichloromethane, dries, filters, crude product chromatographs pure through column
Change obtains product 2.3g, yield 82%.
Embodiment 5
The synthesis of compound 25
The synthesis of intermediate 25-1
In three-necked flask, be added 1,2- (4- bromophenyl)-second diketone (3.65g, 10mmol), 4- pyridine boronic acid (3.7g,
25mmol), potassium carbonate (3.4g, 30mmol), tetra-triphenylphosphine palladium (0.5g), tetrahydrofuran (50ml) and water (20ml), nitrogen
It is protection lower heating 5 hours, cooling, it is extracted with dichloromethane, dries, filters, crude product obtains product 2.6g through column chromatographic purifying,
Yield 73%.
The synthesis of intermediate 25-2
It in flask, is added 4- bromine o-phenylenediamine (1g, 5.5mmol), intermediate 25-1 (2g, 5.5mmol) and acetic acid
(20ml) is heated to 90 degree and reacts 5 hours, and cooling, filtering, filter cake ethyl alcohol recrystallization obtains product 2.3g, yield 83%.
The synthesis of compound 25
In three-necked flask, intermediate 25-2 (2g, 3.9mmol), B- [4- (1- phenyl -1H- benzimidazolyl-2 radicals-is added
Base) phenyl]-boric acid (1.2g, 3.9mmol), potassium carbonate (1.5g, 11.2mmol), tetra-triphenylphosphine palladium (0.1g), tetrahydrofuran
(50ml) and water (20ml) heats 5 hours under nitrogen protection, cooling, is extracted with dichloromethane, dries, filters, crude product is through column
Chromatographic purifying obtains product 2.2g, yield 79%.
Embodiment 6-10
The preparation of organic electroluminescence device
OLED is prepared using the compound of the present invention.
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, NPB is deposited, forms the hole transmission layer 130 of 60nm thickness.
Then, the Alq of 37.5nm thickness is deposited on the hole transport layer31%C-545T is adulterated as luminescent layer 140.
Then, the compounds of this invention of 37.5nm thickness is deposited on the light-emitting layer as 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 shown in Fig. 3) with Photo Research PR650 spectrometer measure
200mA/cm2Current density under efficiency be as shown in table 1.
Comparative example
In addition to electron transfer layer Alq3Outside instead of the compounds of this invention, others are as embodiment 6.
Prepared device (structural schematic diagram is shown in Fig. 3) with Photo Research PR650 spectrometer measure
20mA/cm2Current density under efficiency it is as shown in table 1.
Table 1
Under the same conditions, the organic electroluminescence device prepared using organic electroluminescent compounds of the invention
Efficiency is all higher than comparative example, as described above, the compound of the present invention has high stability, organic electroluminescence hair prepared by the present invention
Optical 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 (6)
1. a kind of organic electroluminescent compounds containing quinoxaline group, it is characterised in that it is following structural 1,2,6-
The compound of 10,13-15,17-21,23-25,27-30:
2. a kind of organic electroluminescence device comprising anode, cathode and organic layer, organic layer include luminescent layer, hole injection
Layer, hole transmission layer, hole blocking layer, electron injecting layer, one layer or more in electron transfer layer, it is characterised in that described organic
Contain the organic electroluminescent compounds as described in claim 1 containing quinoxaline group at least one layer in layer.
3. organic electroluminescence device according to claim 2, it is characterised in that contain quinoline as described in claim 1
Layer where the organic electroluminescent compounds of quinoline group is electron transfer layer and/or electron injecting layer.
4. organic electroluminescence device according to claim 2, it is characterised in that contain quinoline as described in claim 1
The organic electroluminescent compounds of quinoline group are used alone, or are used in mixed way with other compounds.
5. organic electroluminescence device according to claim 2, it is characterised in that contain quinoline as described in claim 1
One such compound is used alone in the organic electroluminescent compounds of quinoline group, or uses its two or more changes simultaneously
Close object.
6. organic electroluminescence device according to claim 2, it is characterised in that it includes anode, hole transmission layer, hairs
Photosphere, electron transfer layer, electron injecting layer and cathode, it is characterised in that containing such as in electron transfer layer and/or electron injecting layer
Compound described in claim 1.
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| CN106711351B (en) * | 2017-01-25 | 2019-01-15 | 上海道亦化工科技有限公司 | Compound and its organic electroluminescence device containing quinoxaline and biphenyl group |
| CN107266418A (en) * | 2017-06-05 | 2017-10-20 | 上海道亦化工科技有限公司 | Compound and its organic electroluminescence device containing quinoxaline and pyridine groups |
| CN107513054A (en) * | 2017-09-29 | 2017-12-26 | 江苏三月光电科技有限公司 | It is a kind of using triazine and quinoxaline as the organic compound of core and its application on OLED |
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