CN108299388A - A kind of phenanthrene derivatives and application thereof and organic electroluminescence device - Google Patents
A kind of phenanthrene derivatives and application thereof and organic electroluminescence device Download PDFInfo
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Abstract
The present invention provides a kind of phenanthrene derivatives, have the following structure formula：The phenanthrene derivatives have 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, electron injecting layer, electron transfer layer, the at least one layer compound containing such as structural formula I in organic layer, the organic electroluminescence device made of phenanthrene derivatives have the advantages that electroluminescent efficiency is good and excitation purity 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 phenanthrene derivatives and application thereof further relate to
A kind of organic electroluminescence device.
Background technology
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 be adjusted as desired by the material for changing luminescent layer
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 with it is 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, since efficiency is low, it is wider that the factors such as service life is short restrict it
General application, especially large screen display.And it is exactly in organic electroluminescence device to restrict one of key factor
The performance of electroluminescent organic material.Additionally, due to OLED device when applying voltage-operated, Joule heat will produce 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.
In OLED material, the speed due to the speed of most electroluminescent organic material transporting holes than transmitting electronics
Soon, the electrons and holes quantity for be easy to causeing luminescent layer is uneven, and 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, be above 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.
Invention content
It is the compound for having the following structure Formulas I the present invention provides a kind of phenanthrene derivatives：
Wherein, Ar1With Ar2Independently selected from substitution or the aryl of unsubstituted C6-C30；
Py is selected from substitution or the pyridyl group of unsubstituted C6-C30；
R1-R8Independently selected from hydrogen, deuterium, the alkyl of C1-C12, the alkoxy of C1-C8, substitution or unsubstituted C6-C30
Aryl.
Optionally, Ar1With Ar2Independently selected from phenyl, cyano-phenyl, fluorine substituted-phenyl, xenyl, diphenyl substituted benzene
Base, naphthalene, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (9,9- bis- replace or
Unsubstituted aryl) fluorenyl, 9,9- be Spirofluorene-based, substitution either unsubstituted dibenzothiophene, substitution or unsubstituted two
Benzofuranyl, the above aryl can be further that the alkyl of C1-C12 replaces.
Optionally, R1-R8Independently selected from hydrogen, phenyl, methyl.
Optionally, the phenanthrene derivatives are the compound of following structural 1-52：
The phenanthrene derivatives of the present invention can be applied to organic electroluminescence device, organic solar batteries, organic 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
Including one layer in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer or electron transfer layer or
One layer or more, wherein at least one layer phenanthrene derivatives contained as described in structural formula I 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；
The layer where phenanthrene derivatives wherein as described in structural formula I is electron transfer layer or electron injecting layer；
The compound that phenanthrene derivatives described in wherein structural formula I are structural formula 1-52；
Phenanthrene derivatives as described in structural formula I can be used alone, and can also be used in mixed way with other compounds；Such as knot
Phenanthrene derivatives described in structure Formulas I can be used alone one such compound, can also use two in structural formula I simultaneously
Kind or two or more compounds.
The organic electroluminescence device of the present invention, it is further preferred that the organic electroluminescence device includes anode, hole
Contain knot in transport layer, luminescent layer, electron transfer layer, electron injecting layer and cathode, wherein electron transfer layer or electron injecting layer
The compound of structure Formulas I；It is further preferred that the change that the compound in electron transfer layer or electron injecting layer is structural formula 1-52
Close object.
The organic electroluminescence device of the present invention, can also also serve as electronics when Compounds of structural formula I is as electron transfer layer
Implanted layer.
The overall thickness of the organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
The present invention organic electroluminescence device using the present invention have structural formula I compound when, can use take
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.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, six cyano, six miscellaneous triphen (hexanitrilehexaazatriphenylene), 2,3,5,6- tetra- fluoro- 7,7', 8,
Tetra- cyanogen dimethyl-parabenzoquinones (F4-TCNQ) of 8'-, polyvinyl carbazole, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of the organic electroluminescence device of the present 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
In reaching effectively electronics from cathode transport to luminescent layer, there is prodigious electron mobility.There is structural formula I except the present invention
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 substitution
Benzene-like compounds, benzimidazoles compound.
Electronics effectively can be injected into organic layer by the electron injecting layer of organic electroluminescence device of the present invention from cathode
In, in addition to the present invention is with Compounds of structural formula I, it is 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 either alkaline-earth metal, can select following compound, and but not limited to this, alkali gold
Oxide either halide, the oxide of alkaline-earth metal or halide, the rare earth of category, alkaline-earth metal, rare earth metal, alkali metal
The organic complex of the oxide of metal either halide, 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 can be used alone can also mixture use, can also match with other electroluminescent organic materials
It closes and uses.
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.Metal motor can be made
It is prepared with vapour deposition method or sputtering method.
Device experimental shows that phenanthrene derivatives of the present invention as described in structural formula I have preferable thermal stability, light efficiency occurred frequently
Rate, high luminance purity.There is electroluminescent efficiency using the organic electroluminescence device that the organic electroluminescent compounds make
The advantages of good and excitation purity is excellent and long lifespan.
Description of the drawings
Fig. 1 is a kind of organic electroluminescence device structural schematic diagram of the present 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 implementation mode
In order to describe the present invention in more detail, spy lifts following example, and but not limited to this.
Embodiment 1
The synthetic route of compound 1
The synthetic method of intermediate 1-1
In flask, 9,10- of addition dibromos are luxuriant and rich with fragrance (15g, 45mmol), 3- pyridine boronic acids pinacol ester (11g, 54mmol),
Potassium carbonate (7.5g, 54mmol), tetrahydrofuran (150mL), water (100mL), tetra-triphenylphosphine palladium (1g) add under nitrogen protection
Heat reflux 12 hours, it is cooling, it is extracted with dichloromethane, dry, concentration, crude product purifies to obtain 8.7g, yield through column chromatography
58%.
The synthetic method of intermediate 1-2
In flask, intermediate 1-1 (8g, 24mmol), connection boric acid pinacol ester (9.1g, 36mmol), potassium acetate is added
(3.5g, 36mmol), dioxane (120mL), Pd (dppf) Cl2(0.5g) is heated to reflux 12 hours under nitrogen protection, cold
But, solvent is removed, adds water, is extracted with dichloromethane, dry, concentration, crude product purifies to obtain 5.9g, yield through column chromatography
65%.
The synthetic method of compound 1
For synthetic method as with intermediate 1-1, raw materials used is chloro- 3, the 5- diphenyl-triazine of intermediate 1-2 and 2-,
Yield 59%.
Embodiment 2
The synthetic route of compound 5
For synthetic method as with intermediate 1-1, raw materials used is chloro- 3, the 5- bis- (4- phenyl benzene)-of intermediate 1-2 and 2-
Triazine, yield 52%.
Embodiment 3
The synthetic route of compound 7
The synthetic method of intermediate 7-1
For synthetic method as with intermediate 1-1, raw materials used is -5 pinacol borate of 9,10- dibromos phenanthrene and 2- phenyl
Pyridine, yield 47%.
The synthetic method of intermediate 7-2
For synthetic method as with intermediate 1-2, raw materials used is intermediate 7-1, yield 55%.
The synthetic method of compound 7
For synthetic method as with intermediate 1-1, raw materials used is chloro- 3, the 5- diphenyl triazine of intermediate 7-2 and 2-, production
Rate 46%.
Embodiment 4
The synthetic route of compound 19
For synthetic method as with intermediate 1-1, raw materials used is intermediate 1-2 and 3,5- diphenyl -2- (4- bromobenzenes
Base)-triazine, yield 64%.
Embodiment 5
The synthetic route of compound 37
For synthetic method as with intermediate 1-1, raw materials used is intermediate 1-2 and 3,5- diphenyl -2- (3- bromobenzenes
Base)-triazine, yield 69%.
Embodiment 6
The synthetic route of compound 41
For synthetic method as with intermediate 1-1, raw materials used is intermediate 7-2 and 3,5- diphenyl -2- (3- bromobenzenes
Base)-triazine, yield 60%.
Embodiment 7-12
The preparation of organic electroluminescence device
OLED is prepared using the compound of the present invention
First, by electrically conducting transparent ito glass substrate 110 (carrying anode 120 above) (the limited public affairs of South China glass group share
Department) it passes through successively：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 layer3The C545T that doping weight ratio is 1% is as luminous
Layer 140.
Then, 37.5nm thickness the compounds of this invention is deposited on the light-emitting layer as electron transfer layer 150.
Finally, vapor deposition 1nm LiF are electron injecting layer 160 and 100nm Al as device cathodes 170.
Prepared device (structural schematic diagram is shown in Fig. 1) with Photo Research PR650 spectrometers measure
20mA/cm2Current density under efficiency such as table 1.
Comparative example 1
In addition to electron transfer layer Alq3Outside instead of the compounds of this invention, others are as embodiment 6-10.
Prepared device (structural schematic diagram is shown in Fig. 1) with Photo Research PR650 spectrometers measure
20mA/cm2Current density under efficiency such as table 1.
Table 1
| Embodiment | Compound | Power efficiency (lm/W) | Color |
| 7 | 1 | 6.4 | Green light |
| 8 | 5 | 6.3 | Green light |
| 9 | 7 | 6.6 | Green light |
| 10 | 19 | 6.7 | Green light |
| 11 | 37 | 6.8 | Green light |
| 12 | 41 | 6.5 | Green light |
| Comparative example 1 | Alq3 | 5.0 | Green light |
Under the same conditions, the efficiency of the organic electroluminescence device prepared using the phenanthrene derivatives of the present invention is higher than
Comparative example, as described above, the phenanthrene derivatives of the present invention have high stability, organic electroluminescence device prepared by the present invention
With high efficiency and optical purity.
Structural formula described in device
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 in the protection domain being defined in the patent claims.
Claims (10)
1. a kind of phenanthrene derivatives, which is characterized in that be the compound for having the following structure Formulas I：
Wherein, Ar1With Ar2Independently selected from substitution or the aryl of unsubstituted C6-C30；
Py is selected from substitution or the pyridyl group of unsubstituted C6-C30；
R1-R8Independently selected from the virtue of hydrogen, deuterium, the alkyl of C1-C12, the alkoxy of C1-C8, substitution or unsubstituted C6-C30
Base.
2. phenanthrene derivatives as described in claim 1, which is characterized in that Ar1With Ar2Independently selected from phenyl, cyano-phenyl,
Fluorine substituted-phenyl, xenyl, diphenyl substituted-phenyl, naphthalene, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,
9- dialkyl group) fluorenyl, (9,9- bis- substitution either unsubstituted aryl) fluorenyl, 9,9- be Spirofluorene-based, substitution or unsubstituted two
Benzothienyl, substitution or unsubstituted dibenzofuran group, the above aryl can be further that the alkyl of C1-C12 replaces.
3. phenanthrene derivatives as described in claim 1, which is characterized in that R1-R8Independently selected from hydrogen, phenyl, methyl.
4. phenanthrene derivatives as described in claim 1, which is characterized in that be the compound of following structural 1-52：
5. application of the phenanthrene derivatives described in claim 1 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
At least one layer in implanted layer, hole transmission layer, exciton barrier-layer, electron transfer layer, which is characterized in that in the organic layer extremely
Few one layer contains phenanthrene derivatives as described in claim 1.
7. organic electroluminescence device as claimed in claim 6, which is characterized in that the phenanthrene derivatives as described in structural formula I
The organic layer at place is electron transfer layer.
8. organic electroluminescence device as claimed in claim 6, which is characterized in that the phenanthrene derivatives as described in structural formula I
One such compound is used alone, or uses two or more the compound in structural formula I simultaneously.
9. organic electroluminescence device as claimed in claim 6, which is characterized in that containing such as right in the hole transmission layer
It is required that the compound of one or more kinds of structural formula 1-52 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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| CN113024511A (en) * | 2021-03-07 | 2021-06-25 | 上海传勤新材料有限公司 | Compound and application thereof in organic electroluminescent device |
| WO2021139452A1 (en) * | 2020-01-08 | 2021-07-15 | 上海传勤新材料有限公司 | Organic electronic material containing nitrogen atom heterocyclic ring, preparation method therefor and application thereof |
| CN113429399A (en) * | 2021-07-10 | 2021-09-24 | 浙江华显光电科技有限公司 | Pyrene derivative, light emitting device material and light emitting device |
| CN114380734A (en) * | 2020-10-19 | 2022-04-22 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compounds, various host materials, and organic electroluminescent devices comprising the same |
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| CN111808082A (en) * | 2019-04-11 | 2020-10-23 | 北京鼎材科技有限公司 | Luminescent material and application thereof |
| CN111808082B (en) * | 2019-04-11 | 2023-10-17 | 北京鼎材科技有限公司 | Luminescent material and application thereof |
| CN111170993A (en) * | 2020-01-08 | 2020-05-19 | 上海传勤新材料有限公司 | Organic electronic material containing nitrogen atom heterocycle and preparation method and application thereof |
| WO2021139452A1 (en) * | 2020-01-08 | 2021-07-15 | 上海传勤新材料有限公司 | Organic electronic material containing nitrogen atom heterocyclic ring, preparation method therefor and application thereof |
| TWI761014B (en) * | 2020-01-08 | 2022-04-11 | 大陸商上海傳勤新材料有限公司 | A kind of organic electronic material containing nitrogen atom heterocycle and its preparation method and application |
| CN114380734A (en) * | 2020-10-19 | 2022-04-22 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compounds, various host materials, and organic electroluminescent devices comprising the same |
| CN112375071A (en) * | 2020-11-18 | 2021-02-19 | 吉林奥来德光电材料股份有限公司 | Organic light-emitting compound and preparation method and application thereof |
| CN112375071B (en) * | 2020-11-18 | 2021-12-10 | 吉林奥来德光电材料股份有限公司 | An organic light-emitting compound and its preparation method and application |
| CN113024511A (en) * | 2021-03-07 | 2021-06-25 | 上海传勤新材料有限公司 | Compound and application thereof in organic electroluminescent device |
| CN113429399A (en) * | 2021-07-10 | 2021-09-24 | 浙江华显光电科技有限公司 | Pyrene derivative, light emitting device material and light emitting device |
| CN113429399B (en) * | 2021-07-10 | 2024-03-26 | 浙江华显光电科技有限公司 | Pyrene derivative, light-emitting device material and light-emitting device |
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