CN109111470A - A kind of organic electroluminescent compounds and luminescent device containing imidazoles - Google Patents
A kind of organic electroluminescent compounds and luminescent device containing imidazoles Download PDFInfo
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Abstract
The present invention provides a kind of organic electroluminescent compounds containing imidazoles, have the following structure formula:The compound has preferable thermal stability, high-luminous-efficiency, high luminance purity, can be applied to organic electroluminescence device, organic solar batteries, Organic Thin Film Transistors or organophotoreceptorswith field.The present invention also provides a kind of organic electroluminescence devices, the device includes anode, cathode and organic layer, organic layer includes at least one layer in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, the at least one layer compound containing such as structural formula I in organic layer has the advantages that electroluminescent efficiency is good and excitation purity is excellent and the service life is long using the organic electroluminescence device that the compound makes.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of organic electroluminescent chemical combination containing imidazoles
Object further relates to a kind of organic electroluminescence device.
Background technique
Organic electroluminescence device (OLEDs) is between two metal electrodes by spin coating or vacuum evaporation deposition one
The device that layer organic material is prepared, a classical three layer organic electroluminescence device include hole transmission layer, luminescent layer
And electron transfer layer.The electronics generated by cathode is followed to be incorporated in through electron transfer layer through hole transmission layer in the hole generated by anode
Luminescent layer forms exciton, then shines.Organic electroluminescence device can according to need the material by changing luminescent layer to adjust
Section emits the light of various needs.
Organic electroluminescence device has self-luminous, wide viewing angle, low energy consumption, efficiency as a kind of novel display technology
High, thin, rich in color, fast response time, Applicable temperature range be wide, low driving voltage, can make flexible and transparent
Display panel and the particular advantages such as environmental-friendly can be applied on flat-panel monitor and a new generation's illumination, be can also be used as
The backlight of LCD.
Since the invention at the bottom of the 1980s, organic electroluminescence device is industrially applied, such as
As screens such as camera and mobile phones, but current OLED device, due to low efficiency, it is wider that the factors such as service life is short restrict it
General application, especially large screen display.And restricting one of key factor is exactly in organic electroluminescence device
The performance of electroluminescent organic material.Additionally, due to OLED device when applying voltage-operated, Joule heat can be generated, so that
Organic material is easy to happen crystallization, affects service life and the efficiency of device, therefore, it is also desirable to develop the organic electroluminescence of stability and high efficiency
Luminescent material.
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 organic electroluminescent compounds containing imidazoles, are the chemical combination for having the following structure Formulas I
Object:
Wherein, L is selected from singly-bound, the aryl of substitution or unsubstituted C6-C30, substitution or unsubstituted C3-C30
Heteroaryl；N is 2 or 3 or 4.
Preferably, L is selected from singly-bound or following aryl and heteroaryl: phenyl, naphthalene, xenyl, fluorenyl, pyridyl group, pyrimidine
Base, pyridazinyl, triazine radical, dibenzofuran group, dibenzothiophene, carbazyl.
It is further preferred that the aryl and heteroaryl are further replaced by the alkyl of C1-C12.
Preferably, the organic electroluminescent compounds containing imidazoles are the compound of following structural 1-50:
Organic electroluminescent compounds containing imidazoles of the invention can be applied to organic electroluminescence device, solar-electricity
Pond, Organic Thin Film Transistors or organophotoreceptorswith field.
The present invention also provides a kind of organic electroluminescence device, which includes anode, cathode and organic layer, organic layer
Include at least one in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer
Layer, at least one layer of organic electroluminescent compounds containing imidazoles containing 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.
Preferably, the layer where the organic electroluminescent compounds containing imidazoles is electron transfer layer.
The organic electroluminescent compounds containing imidazoles as described in structural formula I are used alone, or mix with other compounds
It uses；The organic electroluminescent compounds containing imidazoles as described in structural formula I can be used alone one such compound,
It can be simultaneously using two or more the compound in structural formula I；A kind of containing selected from structural formula 1-50 is used alone
The organic electroluminescent compounds of imidazoles, or the organic electroluminescence containing imidazoles using two or more selected from structural formula 1-50 is sent out simultaneously
Optical compounds.
The overall thickness of organic electroluminescence device organic layer of the invention is 1-1000nm, preferably 50-500nm.
When having the compound of structural formula I using the present invention, can arrange in pairs or groups makes organic electroluminescence device of the invention
With other materials, such as in hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and barrier layer
Deng, and obtain blue and green light, yellow light, feux rouges or white light.
The hole transmission layer and hole injection layer of organic electroluminescence device of the present invention, material requested have good hole
Transmission performance can effectively be transferred to hole on luminescent layer from anode.In addition to can be used with the compound of the present invention
It outside, can also include other small molecules and macromolecular organic compound, including but not limited to carbazole compound, triaromatic amine
Close object, benzidine compound, compound of fluorene class, phthalocyanine-like compound, the miscellaneous triphen (hexanitrilehexaaza of six cyano six
Triphenylene), tetra- cyanogen dimethyl-parabenzoquinone (F4-TCNQ) of 2,3,5,6- tetra- fluoro- 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.Except it is of the invention there is Compounds of structural formula I in addition to, following compound can also be contained, but not limited to this,
Naphthalene compounds, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance class compound,Class compound, glimmering anthracene compound, anthracene class chemical combination
Object, pentacene class compound, class compound, two aromatic ethylene class compounds, triphenylamine ethylene compounds, aminated compounds,
Benzimidazoles compound, furfuran compound, organic metal chelate complex.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires good electronic transmission performance, energy
It reaches in effectively electronics from cathode transport to luminescent layer, there is very big electron mobility.Except of the invention has structural formula I
Outside compound, it is also an option that following compound, but not limited to this: oxa- oxazole, thiazole compound, triazole chemical combination
Object, three nitrogen piperazine class compounds, triazine class compound, quinoline class compound, phenodiazine anthracene compound, siliceous heterocyclic chemical combination
Object, quinolines, ferrosin class compound, metallo-chelate (such as Alq3), fluorine substituted benzene compound, benzimidazole
Compound.
Electronics effectively can be injected into organic layer from cathode by the electron injecting layer of organic electroluminescence device of the present invention
In, it is mainly selected from the alkali metal perhaps compound of alkali metal or compound or alkali selected from alkaline-earth metal or alkaline-earth metal
Metal complex can choose following compound, but not limited to this: alkali metal, alkaline-earth metal, rare earth metal, alkali metal
Oxide or halide, the oxide of alkaline-earth metal or halide, the oxide of rare earth metal or halide, alkali metal
Or the organic complex of alkaline-earth metal；Preferably lithium, lithium fluoride, lithia, lithium nitride, 8-hydroxyquinoline lithium, caesium, carbonic acid
Caesium, 8-hydroxyquinoline caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, magnesia, these compounds can individually make
With that can also be used with mixture, can also be used cooperatively with other electroluminescent organic materials.
Each layer of organic layer in organic electroluminescence device of the invention can be steamed by vacuum vapour deposition, molecular beam
It is prepared by the modes such as plating method, the dip coating for being dissolved in solvent, spin-coating method, stick coating method or inkjet printing.Metal motor can be made
It is prepared with vapour deposition method or sputtering method.
Device experimental shows organic electroluminescent compounds containing imidazoles 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
The advantage that efficiency is good and excitation purity is excellent and the service life is long.
Detailed description of the invention
Fig. 1 is a kind of organic electroluminescence device structural schematic diagram of the invention,
Wherein, 110 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 synthetic route of intermediate C
The synthetic method of intermediate A
In flask, the bromo- 2- fluorobenzaldehyde (20g, 0.1mol) of 4-, benzimidazole (12g, 0.1mol), water are sequentially added
It closing ferric trichloride (10mmol), potassium phosphate (0.2mol) and DMF (200mL) react 20 hours at 120 DEG C, and it is cooling, add water,
It is extracted with dichloromethane, dry, concentration, product obtains product 21.7g, yield 73% through column chromatographic purifying out.
The synthetic method of intermediate B
It in flask, sequentially adds intermediate A (20g, 57mmol), anhydrous tetrahydro furan (250mL), under room temperature, slowly
Be added 2- xenyl magnesium bromide grignard reagent (75mmol), be heated to reflux 2 hours, it is cooling, be slowly added to dilute hydrochloric acid adjust pH to
7, it is extracted with dichloromethane, is concentrated, acetic acid (200mL) and concentrated hydrochloric acid (10mL) is added, is heated to reflux 5 hours, it is cooling, it removes molten
Agent, is added ethyl alcohol, and filtering is dried to obtain product 18g, yield 73%.
The synthetic method of compound C
It in flask, sequentially adds intermediate B (20g, 46mmol), connection boric acid pinacol ester (14g, 55mmol), acetic acid
Potassium (8.6g, 90mmol), dioxane (220mL), Pd (dppf) Cl2(0.5g) is heated to reflux 12 hours under nitrogen protection,
It is cooling, solvent is removed, adds water, is extracted with dichloromethane, dry, concentration, crude product obtains 15g, yield through column chromatographic purifying
68%.
Embodiment 2
The synthetic route of compound F
The synthetic method of intermediate D
Its synthetic method replaces the bromo- 2- fluorobenzaldehyde of 4- such as intermediate A, with the bromo- 2- fluorobenzaldehyde of raw material 5-, produces
Rate 69%.
The synthetic method of intermediate E
For its synthetic method as the synthesis of intermediate B, raw materials used is intermediate D, yield 65%.
The synthetic method of intermediate F
For its synthetic method such as intermediate C, raw materials used is intermediate E, yield 71%.
Embodiment 3
The synthetic route of compound 1
The synthetic method of compound 1
It in flask, sequentially adds intermediate E (2g, 4.6mmol), intermediate F (2.2g, 4.6mmol), potassium carbonate
(0.94g, 6.9mmol), tetrahydrofuran (15mL), water (10mL), tetra-triphenylphosphine palladium (0.1g) heat back under nitrogen protection
Stream 12 hours, it is cooling, it is extracted with dichloromethane, dry, concentration, crude product obtains 2.4g, yield 73% through column chromatographic purifying.
As the synthesis of compound 1, raw materials used is raw material specifically such as table 1 for the synthesis of other embodiments compound:
1 raw material of table and yield
Embodiment 10-16
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%C545T is adulterated as luminescent 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 is 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 spectrometer 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, other steps are as embodiment 10-16.
Prepared device (structural schematic diagram is shown in Fig. 1) with Photo Research PR650 spectrometer measure
20mA/cm2Current density under power efficiency such as table 2.
2 experimental result of table
| Embodiment | Compound | Power efficiency (lm/W) | Color |
| 10 | 1 | 6.1 | Green light |
| 11 | 3 | 6.0 | Green light |
| 12 | 5 | 6.2 | Green light |
| 13 | 18 | 6.3 | Green light |
| 14 | 20 | 6.2 | Green light |
| 15 | 22 | 6.1 | Green light |
| 16 | 23 | 6.3 | Green light |
| Comparative example 1 | Alq3 | 5.0 | Green light |
As shown in Table 2, under the same conditions, the organic electroluminescence prepared using organic electroluminescent compounds of the invention
The efficiency of luminescent device is higher than comparative example, as described above, the compound of the present invention has high stability, it is prepared by the present invention to have
Organic electroluminescence devices have high efficiency and optical purity.
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 organic electroluminescent compounds containing imidazoles, which is characterized in that be the compound for having the following structure Formulas I:
Wherein, L is selected from the heteroaryl of singly-bound, the aryl of substitution or unsubstituted C6-C30, substitution or unsubstituted C3-C30
Base；N is 2 or 3 or 4.
2. as described in claim 1 containing the organic electroluminescent compounds of imidazoles, which is characterized in that L is selected from singly-bound or following
Aryl and heteroaryl: phenyl, naphthalene, xenyl, fluorenyl, pyridyl group, pyrimidine radicals, pyridazinyl, triazine radical, dibenzofuran group,
Dibenzothiophene, carbazyl.
3. as claimed in claim 2 containing the organic electroluminescent compounds of imidazoles, which is characterized in that the aryl and heteroaryl
Further replaced by the alkyl of C1-C12.
4. as described in claim 1 containing the organic electroluminescent compounds of imidazoles, which is characterized in that be following structural 1-50
Compound:
5. application of the organic electroluminescent compounds described in claim 1 containing imidazoles in organic electroluminescence device.
6. a kind of organic electroluminescence device, which includes anode, cathode and organic layer, and organic layer includes luminescent layer, hole
Implanted layer, hole transmission layer, hole blocking layer, electron injecting layer, at least one layer in electron transfer layer, which is characterized in that institute
It states at least one layer of containing as described in claim 1 containing the organic electroluminescent compounds of imidazoles in organic layer.
7. organic electroluminescence device as claimed in claim 6, which is characterized in that having containing imidazoles described in claim 1
Layer where organic electro luminescent compounds is electron transfer layer.
8. organic electroluminescence device as claimed in claim 6, which is characterized in that having containing imidazoles described in claim 1
Organic electro luminescent compounds are used alone, or are used in mixed way with other compounds.
9. organic electroluminescence device as claimed in claim 6, which is characterized in that be used alone a kind of selected from such as claim
The organic electroluminescent compounds containing imidazoles of structural formula 1-50 described in 4, or wanted simultaneously using two or more selected from such as right
The organic electroluminescent compounds containing imidazoles of structural formula 1-50 described in asking 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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| WO2007011163A1 (en) * | 2005-07-22 | 2007-01-25 | Lg Chem. Ltd. | Imidazole derivatives and organic electronic device using the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110746442A (en) * | 2018-12-10 | 2020-02-04 | 广州华睿光电材料有限公司 | Imidazole spiro-containing compound and application thereof |
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