CN109535093A - A kind of trisubstituted benzene based compound and organic electroluminescence device - Google Patents
A kind of trisubstituted benzene based compound and organic electroluminescence device Download PDFInfo
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Abstract
The present invention provides a kind of trisubstituted benzene based compounds, have the following structure formula:The compound has preferable thermal stability, high-luminous-efficiency, high luminance purity, it can be applied to organic electroluminescence device, solar battery, Organic Thin Film Transistors or organophotoreceptorswith field, have the advantages that electroluminescent efficiency is good and excitation purity is excellent and the service life is long using the organic electroluminescence device based on the production of trisubstituted benzene based compound.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of trisubstituted benzene based compound further relates to one
Kind 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.
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
The present invention provides a kind of trisubstituted benzene based compounds, are the compound for having the following structure Formulas I:
Wherein, Z1-Z3In at least one group be N, remaining is CH；
L is selected from singly-bound, phenyl, naphthalene, anthryl and phenanthryl；
Ar1-Ar3Aryl independently selected from substitution or unsubstituted C6-C30；
R1-R6At least one group is CN, remaining group is independently selected from H, F, CH3Or CF3。
Optionally, Ar1-Ar2Independently selected from phenyl, naphthalene, xenyl；
Optionally, Ar3Selected from phenyl, xenyl, diphenyl substituted-phenyl, naphthalene, three and phenyl, anthryl, phenanthryl, benzo
Phenanthryl, pyrenyl, base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (9,9- bis- replaces or unsubstituted aryl) fluorenyl, 9,9-
Spirofluorene-based, dibenzothiophene, dibenzofuran group, carbazyl.
Optionally, the Ar1-Ar3Replaced by the alkyl of C1-C6.
Optionally, the trisubstituted benzene based compound specifically includes the compound of following structural 1-105:
Trisubstituted benzene based compound of the invention can be applied to organic electroluminescence device, solar battery, organic thin
Film transistor or organophotoreceptorswith field.
The present invention also provides a kind of organic electroluminescence device, which includes anode, cathode and organic layer, organic layer
Include at least one in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer or electron transfer layer
Layer, it is at least one layer of containing such as above-mentioned trisubstituted benzene based compound in the organic layer.
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, wherein the layer where trisubstituted benzene based compound as described in structural formula I is electron transfer layer and hole
At least one layer in barrier layer.
Trisubstituted benzene based compound as described in structural formula I is used alone, or is used in mixed way with other compounds；Such as structure
Trisubstituted benzene based compound described in Formulas I can be used alone one such compound, can also be simultaneously using in structural formula I
Two or more compound；A kind of trisubstituted benzene based compound selected from structural formula 1-105 is used alone, or simultaneously
Use the two or more trisubstituted benzene based compounds selected from structural formula 1-105.
Still optionally further, organic electroluminescence device of the invention includes anode, hole transmission layer, luminescent layer, electronics
Transport layer, electron injecting layer and cathode wherein contain one or more kinds of structures in electron transfer layer or electron injecting layer
The compound of Formulas I；It is further preferred that containing one or more kinds of structural formula 1- in electron transfer layer or electron injecting layer
105 compound.
The overall thickness of organic electroluminescence device organic layer of the invention is 1-1000nm, preferably 50-500nm.
Organic electroluminescence device of the invention can be used and take when being had the compound of structural formula I using the present invention
With other materials, such as hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and barrier layer, 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
Six miscellaneous triphen (hexanitrilehexaazatriphenylene) of class compound, six terphenyls and cyano, 2,3,5,6- tetra- are fluoro-
Tetra- cyanogen dimethyl-parabenzoquinone (F4-TCNQ) of 7,7', 8,8'-, 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, luxuriant and rich with fragrance class compound,Class compound, glimmering anthracene compound, anthracene compound, pentacene class compound, class compound, two
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, and 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 trisubstituted benzene based compound 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 efficiency good
With the advantage that excitation purity is excellent and the service life is long.
Detailed description of the invention
Fig. 1 is a kind of organic electroluminescence device structural schematic diagram of the invention,
Wherein, 110 it is represented as glass substrate, 120 are represented as anode, and 130 are represented as hole 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 yin
Pole.
Fig. 2 is another 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 injection layer, and 140 are represented as sky
Cave transport layer, 150 are represented as luminescent layer, and 160 are represented as hole blocking layer, and 170 are represented as electron transfer layer, and 180 represent electronics
Implanted layer, 190 are represented as cathode.
Specific embodiment
In order to describe the present invention in more detail, spy lifts following example, and but not limited to this.
Embodiment 1
The synthetic route of intermediate A
The synthetic method of intermediate A
In flask, addition intermediate 2- (the bromo- phenyl of the chloro- 5- of 3-) -4,6- diphenyl -1,3,5-triazines (20g,
47mmol), phenyl boric acid (7.5g, 61mmol), potassium carbonate (13.6g, 100mmol), tetra-triphenylphosphine palladium (1g), tetrahydrofuran
(400mL) and water (200mL), is heated to reflux 12 hours under nitrogen protection, cooling, is extracted with dichloromethane, dry, concentration,
Crude product obtains 16.5g, yield 84% with re crystallization from toluene.
The synthetic method of other intermediates is as with intermediate A, is all to use brominated triazine and other boric acid as raw material,
Specific such as table 1:
Table 1
Embodiment 2
The synthetic route of compound 5
The synthetic method of compound 5
In flask, it is added intermediate B (2.5g, 4.8mmol), biphenylboronic acid ester (1.8g, 5.8mmol), potassium carbonate
(1.3g, 10mmol), palladium acetate (0.1g), X-phos (0.3g), toluene (20mL), ethyl alcohol (10mL) and water (10mL), in nitrogen
It is heated to reflux under gas shielded 12 hours, it is cooling, it is extracted with dichloromethane, dry, concentration, crude product is obtained through column chromatographic purifying
2.2g, yield 68%.
The synthetic method of other embodiments is as with compound 5, is all to use intermediate A as raw material, it is other in addition to
Boric acid used is different outer, specific such as table 2:
Table 2
Embodiment 15-27
The preparation of organic electroluminescence device
OLED is prepared using the compound 5 of embodiment 2
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, HIL (60nm) is deposited on ITO and is used as hole injection layer 130.
Then, compound N PB is deposited, forms the hole transmission layer 140 of 10nm thickness.
Then, the luminescent layer 150 of 40nm thickness is deposited on the hole transport layer.Wherein, luminescent material based on MADN, and with
The BD of 5% weight ratio is as doping guest materials.
Then, the compounds of this invention of 25nm thickness is deposited on the light-emitting layer as electron transfer layer 160.
Finally, vapor deposition 1nm LiF is electron injecting layer 170 and 100nm Al as device cathodes 180.
Prepared device (structural schematic diagram is shown in Fig. 1) is measured with Photo Research PR650 spectrometer in 25mA/
cm2Current density under brightness and service life such as the following table 3.
Comparative example 1-5
Other than electron transfer layer replaces the compounds of this invention with comparative example compound, others are with embodiment 15-27 mono-
Sample.Prepared device (structural schematic diagram is shown in Fig. 1) with Photo Research PR650 spectrometer measure in 25mA/cm2
Current density under brightness, the service life numerical value in table indicates embodiment and the service life in the service life and comparative example 1 of comparative example 2-5
Percentage, it is specific such as table 3.
Table 3
The effect of comparative example 5 is least ideal it can be seen from the experimental data of table 3, and comparative example 1~4 takes second place, of the present inventionization
It is the most excellent to close physical performance.Compared to the structural formula of comparative example 1,2,3,4, in the compounds of this invention structural formulaThe group of connection is the aromatic radical with CN base, the organic electroluminescence of experimental result the compound of the present invention preparation
The light emission luminance of luminescent device is much higher than comparative example, meanwhile, the service life is also improved largely.
Therefore, the discovery of the invention existsOn the basis of introduce with CN base aromatic radical obtained by
The organic electroluminescence device of compound preparation has higher efficiency and optical purity, and the service life rises appreciably.
Embodiment 28-32
The preparation of organic electroluminescence device
OLED is prepared using the compound of the present invention and comparative example
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, HIL (60nm) is deposited on ITO and is used as hole injection layer 130.
Then, compound N PB is deposited, forms the hole transmission layer 140 of 10nm thickness.
Then, the luminescent layer 150 of 40nm thickness is deposited on the hole transport layer.Wherein, luminescent material based on MADN, and with
The BD of 5% weight ratio is as doping guest materials.
Then, the compounds of this invention of 5nm thickness is deposited on the light-emitting layer as hole blocking layer 160.
Then, the Alq of 20nm thickness is deposited on the light-emitting layer3As electron transfer layer 170.
Finally, vapor deposition 1nm LiF is electron injecting layer 180 and 100nm Al as device cathodes 190.
Prepared device (structural schematic diagram is shown in Fig. 2) is measured with Photo Research PR650 spectrometer in 25mA/
cm2Current density under brightness, such as the following table 4.
Comparative example 6-7
Other than hole blocking layer replaces the compounds of this invention with comparative example compound, others are with embodiment 28-32 mono-
Sample.
Prepared device (structural schematic diagram is shown in Fig. 2) with Photo Research PR650 spectrometer measure
25mA/cm2Current density under brightness, it is specific such as table 4.
Table 4
| Embodiment | Compound | Brightness (cd/m2) | Color |
| 28 | 7 | 1340 | Blue light |
| 29 | 11 | 1296 | Blue light |
| 30 | 24 | 1306 | Blue light |
| 31 | 30 | 1270 | Blue light |
| 32 | 44 | 1356 | Blue light |
| Comparative example 6 | ETM1 | 1030 | Blue light |
| Comparative example 7 | Alq3 | 980 | Blue light |
By the experimental result of table 4 it is known that the organic electroluminescent that the compounds of this invention is prepared as hole blocking layer
The performance of device is far superior to comparative example.
Structural formula described in device is as follows:
The preferred embodiment of the present invention has been described in detail above.It should be appreciated that those skilled in the art without
It needs creative work according to the present invention can conceive and makes many modifications and variations.Therefore, all technologies in the art
Personnel are available by logical analysis, reasoning, or a limited experiment on the basis of existing technology under this invention's idea
Technical solution, all should be within the scope of protection determined by the claims.
Claims (10)
1. a kind of trisubstituted benzene based compound, which is characterized in that have the following structure the compound of Formulas I:
Wherein, Z1-Z3In at least one group be N, remaining is CH；
L is selected from singly-bound, phenyl, naphthalene, anthryl and phenanthryl；
Ar1-Ar3Aryl independently selected from substitution or unsubstituted C6-C30；
R1-R6At least one group is CN, remaining group is independently selected from H, F, CH3Or CF3。
2. trisubstituted benzene based compound as described in claim 1, which is characterized in that Ar1-Ar2Independently selected from phenyl, naphthalene,
Xenyl.
3. trisubstituted benzene based compound as claimed in claim 2, which is characterized in that Ar3It is taken selected from phenyl, xenyl, diphenyl
For phenyl, naphthalene, three and phenyl, anthryl, phenanthryl, benzo phenanthryl, pyrenyl, base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (9,
9- bis- replaces or unsubstituted aryl) fluorenyl, 9,9- be Spirofluorene-based, dibenzothiophene, dibenzofuran group, carbazyl.
4. trisubstituted benzene based compound as claimed in claim 3, which is characterized in that the Ar1-Ar3It is taken by the alkyl of C1-C6
Generation.
5. trisubstituted benzene based compound as described in claim 1, which is characterized in that the R1Selected from CN, F or CF3。
6. trisubstituted benzene based compound as described in claim 1, which is characterized in that specifically include following structural 1-105's
Compound:
7. a kind of organic electroluminescence device, which includes anode, cathode and organic layer, and organic layer includes luminescent layer, hole
At least one layer in implanted layer, hole transmission layer, hole blocking layer, electron injecting layer or electron transfer layer, which is characterized in that institute
It states at least one layer in organic layer and contains trisubstituted benzene based compound as described in claim 1.
8. organic electroluminescence device as claimed in claim 7, which is characterized in that be used alone a kind of selected from such as claim
The trisubstituted benzene based compound of structural formula 1-105 described in 6, or simultaneously using two or more selected from as claimed in claim 6
The trisubstituted benzene based compound of structural formula 1-105.
9. organic electroluminescence device as claimed in claim 7, which is characterized in where the trisubstituted benzene based compound
Layer be at least one layer in electron transfer layer and hole blocking layer.
10. organic electroluminescence device as claimed in claim 7, which is characterized in that the overall thickness of the organic layer is 1-
1000nm。
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