CN108470828A - A kind of 2,4,6- trifluoromethyl pyridines compound and application thereof and luminescent device - Google Patents
A kind of 2,4,6- trifluoromethyl pyridines compound and application thereof and luminescent device Download PDFInfo
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- CN108470828A CN108470828A CN201810258776.1A CN201810258776A CN108470828A CN 108470828 A CN108470828 A CN 108470828A CN 201810258776 A CN201810258776 A CN 201810258776A CN 108470828 A CN108470828 A CN 108470828A
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Abstract
The present invention provides a kind of 2,4,6 trifluoromethyl pyridine compounds, have the following structure formula：2,4, the 6 trifluoromethyl pyridine compound has preferable thermal stability, high-luminous-efficiency, high luminance purity, can be applied to organic electroluminescence device, solar cell, 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, contain 2 such as structural formula I at least one layer in organic layer, 4,6 trifluoromethyl pyridine Compound Compounds, using 2, the organic electroluminescence device that 4,6 trifluoromethyl pyridine compounds make has high efficiency and optical purity.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to one kind 2,4,6- trifluoromethyl pyridines compound and its use
On the way, a kind of luminescent device is further related to.
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.
Organic electrophosphorescenpolymer phenomenon, breaches theoretical limitation of the organic electroluminescent quantum efficiency less than 25%, and promotion is arrived
100% (Baldo M.A., Forrest S.R.Et al, Nature, 1998,395,151-154), application also greatly carry
The high efficiency of organic electroluminescence device.Usually, electroluminescent phosphorescence needs to use host-guest system technology, is commonly used as phosphorus
The CBP (4,4'-bis (9-carbazolyl)-biphenyl) of light material of main part has efficient and high triplet energy level, when its work
Based on material when, triplet energy state effectively can be transferred to object phosphorescent light-emitting materials from light emitting host material.But by
In the characteristic of the hole of CBP easily transmission and the flowing of electronics difficulty so that as a result the charge unbalance of luminescent layer reduces the effect of device
Rate.
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
The present invention provides a kind of 2,4,6- trifluoromethyl pyridine compounds, are the compound for having the following structure Formulas I：
Wherein, R1And R2Independently selected from the substitution either aryl of unsubstituted C6-C30, substitution or unsubstituted C3-
Two aromatic amines of the heteroaryl of C30, the substitution either fragrant phosphino- of unsubstituted C6-C30, substitution or unsubstituted C12-C30
Base, substitution either the triaromatic amine base of unsubstituted C18-C30, substitution or unsubstituted C12-C30 carbazyl, substitution or
The indyl of the unsubstituted C8-C30 of person.
Optionally, the aryl be selected from phenyl, naphthalene, xenyl, three and phenyl, anthryl, fluoranthene base, pyrenyl, phenanthryl,
Base and the aryl replace gained group by the alkyl of C1-C12.
Optionally, the heteroaryl is selected from (9,9- dialkyl group) fluorenyl, (9,9- bis- substitutions or unsubstituted aryl) fluorenes
Base, dibenzothiophene, dibenzofuran group, pyridyl group, pyrimidine radicals, pyridazinyl, triazine radical, imidazole radicals, oxazolyls, thiazole
Base, thiadiazolyl group, quinolyl, isoquinolyl, quinazolyl, quinoxalinyl, azepine dibenzofuran group, azepine dibenzothiophenes
Base, acridinyl, phenoxazines, phenoxazine thiophene and the heteroaryl replace gained group by the alkyl of C1-C12.
Further alternative, 2,4,6- trifluoromethyl pyridine compounds are the compound of following structural 1-44：
The 2,4,6- trifluoromethyl pyridine compounds of the present invention can be applied to organic electroluminescence device, solar cell, have
Machine thin film transistor (TFT) or organophotoreceptorswith field.
The present invention also provides a kind of organic electroluminescence device, which includes anode, cathode and organic layer, organic layer
Including 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 2,4,6- trifluoromethyl pyridine compounds containing as described in structural formula I in the organic layer.
Wherein organic layer is luminescent layer；
Or organic layer is luminescent layer and electron transfer layer；
Or organic layer is luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole transmission layer and luminescent layer；
Or organic layer is hole injection layer, hole transmission layer and luminescent layer；
Or organic layer is hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole injection layer, hole transmission layer, barrier layer, luminescent layer, electron transfer layer and electron injection
Layer；
Or organic layer is hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and hole blocking layer；
Or organic layer is hole transmission layer, luminescent layer, electron injecting layer and hole blocking layer.
Further alternative, the layer where 2,4, the 6- trifluoromethyl pyridine compounds is luminescent layer or electron transfer layer.
2 as described in structural formula I, 4,6- trifluoromethyl pyridine compounds are used alone, or are used in mixed way with other compounds；Such as
2 described in structural formula I, 4,6- trifluoromethyl pyridine compounds can be used alone one such compound, can also use simultaneously
Two or more compound in structural formula I；A kind of 2,4,6- trifluoromethyl pyridines selected from structural formula 1-44 are used alone
Compound, or two or more 2,4, the 6- trifluoromethyl pyridine compounds selected from structural formula 1-44 are used simultaneously.
Still optionally further, organic electroluminescence device of the invention include anode, hole injection layer, hole transmission layer,
Contain one or more in luminescent layer, electron transfer layer, electron injecting layer and cathode, wherein luminescent layer or electron transfer layer
Structural formula I compound；It is further preferred that containing one or more kinds of structural formulas in luminescent layer or electron transfer layer
The compound of 1-44.
The overall thickness of the organic electroluminescence device organic layer of the present 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 the organic electroluminescence device of the present 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.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.In addition to the present invention is with Compounds of structural formula I, 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
In reaching effectively electronics from cathode transport to luminescent layer, there is prodigious electron mobility.In addition to that can use with this hair
Outside bright compound, it is also an option that following compound, but not limited to this：Oxa- oxazole, thiazole compound, triazole
Compound, three nitrogen piperazine class compounds, triazine class compound, quinoline class compound, phenodiazine anthracene compound, siliceous heterocyclic
Compound, quinolines, ferrosin class compound, metallo-chelate (such as Alq3), fluorine substituted benzene compound, benzo miaow
Azole compounds.
Electronics effectively can be injected into organic layer by the electron injecting layer of organic electroluminescence device of the present invention from cathode
In, it is mainly selected from the alkali metal either compound of alkali metal or the compound selected from alkaline-earth metal or alkaline-earth metal or alkali
Metal complex can select following compound, and but not limited to this：Alkali metal, alkaline-earth metal, rare earth metal, alkali metal
Oxide either halide, the oxide of alkaline-earth metal or halide, the oxide of rare earth metal or halide, alkali metal
Or the organic complex of alkaline-earth metal；Preferably lithium, lithium fluoride, lithia, lithium nitride, 8-hydroxyquinoline lithium, caesium, carbonic acid
Caesium, 8-hydroxyquinoline caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, magnesia, these compounds can individually make
With can also mixture use, can also be used cooperatively with other electroluminescent organic materials.
Each layer of organic layer in the organic electroluminescence device of the present invention can be steamed by vacuum vapour deposition, molecular beam
It is prepared by the modes such as plating method, the dip coating for being dissolved in solvent, spin-coating method, stick coating method or inkjet printing.Metal motor can be made
It is prepared with vapour deposition method or sputtering method.
Device experimental shows that 2 of the present invention as described in structural formula I, 4,6- trifluoromethyl pyridine compounds have preferable thermostabilization
Property, high-luminous-efficiency, high luminance purity.The organic electroluminescence device made of the 2,4,6- trifluoromethyl pyridine compounds has
The advantages of electroluminescent efficiency is 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 be glass substrate, and 120 be anode, and 130 be hole injection layer, and 140 be hole transmission layer, and 150 be resistance
Barrier, 160 be luminescent layer, and 170 be electron transfer layer, and 180 be electron injecting layer, and 190 be cathode；
Fig. 2 is another organic electroluminescence device structural schematic diagram of the present invention,
Wherein, 110 be glass substrate, and 120 be anode, and 130 be hole transmission layer, and 140 be luminescent layer, and 150 pass for electronics
Defeated layer, 160 be electron injecting layer, and 170 be 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 3
The synthetic method of compound 3
In flask, addition 2- triphens ene boric acid (3g, 11mmol), 3,5- bis- chloro- 2,4,6- trifluoromethyl pyridines (1g,
5mmol), potassium carbonate (2.7g, 20mmol), tetra-triphenylphosphine palladium (0.1g), tetrahydrofuran (25mL) and water (15mL), in nitrogen
It under protection, is heated to reflux 12 hours, cooling is extracted, concentration with dichloromethane, and crude by column chromatography is purified to obtain 2.1g, be produced
Rate 74%.
Embodiment 2-11
The synthetic method of embodiment 2-11 as the synthetic method of embodiment, and use boric acid and 3,5- bis- chloro- 2,4,
6- trifluoromethyl pyridines are as raw material, table 1 specific as follows：
Table 1
Embodiment 10-15
The preparation of organic electroluminescence device
OLED is prepared using the compound of above-described embodiment
First, by electrically conducting transparent ito glass substrate 110 (carrying anode 120 above) (the limited public affairs of South China glass group share
Department) it passes through successively：Deionized water, ethyl alcohol, acetone and deionized water were cleaned, then with oxygen plasma treatment 30 seconds.
Then, the MnO of 3nm thickness is deposited on ITO3(molybdenum oxide) is hole injection layer 130.
Then, the TAPC that 50nm thickness is deposited on hole injection layer is hole mobile material 140.
Then, TCTA is deposited, forms the electronic barrier layer 150 of 5nm thickness.
Then, the luminescent layer 160 of 20nm thickness is deposited on electronic barrier layer, wherein shine based on the compounds of this invention
Material, and the Ir (ppy) for being 3% with weight ratio3Guest materials is adulterated as phosphorescence.
Then, the BmPYPB of 40nm thickness is deposited on the light-emitting layer as electron transfer layer 170.
Finally, vapor deposition 1nm LiF are electron injecting layer 180 and 80nm Al as device cathodes 190.
Prepared device (structural schematic diagram is shown in Fig. 1) with Photo Research PR650 spectrometers measure
5000cd/m2Brightness under current efficiency be such as table 2.
Comparative example 1
Except use CBP replace the compounds of this invention as material of main part in addition to, other steps are according to the device of embodiment 12-15
Preparation method prepares device.
Table 2
| Embodiment | Compound | Current efficiency (cd/A) | Luminescent color |
| 12 | 27 | 50 | Green light |
| 13 | 32 | 52 | Green light |
| 14 | 33 | 53 | Green light |
| 15 | 39 | 55 | Green light |
| Comparative example 1 | CBP | 45 | Green light |
The structural formula of compound described in device is as follows：
From Table 2, it can be seen that when the compounds of this invention is used for organic electroluminescence device, operating voltage can be reduced,
Device efficiency is improved, is the phosphorescent light body material with excellent performance.As described above, the compound of the present invention has high stabilization
Property, the organic electroluminescence device of preparation has high efficiency and optical purity.
Embodiment 16-22
The preparation of organic electroluminescence device
OLED is prepared using the compound of above-described embodiment
First, by electrically conducting transparent ito glass substrate 110 (carrying anode 120 above) (the limited public affairs of South China glass group share
Department) 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 weight ratio is 1% 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 are electron injecting layer 160 and 100nm Al as device cathodes 170.
Prepared device (structural schematic diagram is shown in Fig. 2) with Photo Research PR650 spectrometers measure
20mA/cm2Current density under efficiency, such as table 3.
Comparative example 2
Except using Alq3Instead of the compounds of this invention as electron transfer layer outside, other steps are according to embodiment 16-22's
Device preparation method prepares device.Prepared device (structural schematic diagram is shown in Fig. 2) Photo Research PR650 spectrum
Instrument measure in 20mA/cm2Current density under efficiency such as table 3.
Table 3
| Embodiment | Compound | Power efficiency (lm/W) | Color |
| 16 | 3 | 5.9 | Green light |
| 17 | 6 | 5.8 | Green light |
| 18 | 9 | 5.7 | Green light |
| 19 | 15 | 6.1 | Green light |
| 20 | 17 | 6.2 | Green light |
| 21 | 18 | 6.3 | Green light |
| 22 | 19 | 6.0 | Green light |
| Comparative example 2 | Alq3 | 5.0 | Green light |
As shown in Table 3, under the same conditions, the Organic Electricity prepared as electron transfer layer using the compound of the present invention
The efficiency of electroluminescence device is higher than comparative example, as described above, the compound of the present invention has high stability, prepared by the present invention
Organic electroluminescence device has 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. one kind 2,4,6- trifluoromethyl pyridine compounds, which is characterized in that be the compound for having the following structure Formulas I：
Wherein, R1And R2Independently selected from the substitution either aryl of unsubstituted C6-C30, substitution or unsubstituted C3-C30
Heteroaryl, substitution either two aromatic aminos of the fragrant phosphino- of unsubstituted C6-C30, substitution or unsubstituted C12-C30, take
Generation either the triaromatic amine base of unsubstituted C18-C30, substitution or unsubstituted C12-C30 carbazyl, substitution or not
The indyl of substituted C8-C30.
2. as described in claim 12,4,6- trifluoromethyl pyridine compounds, which is characterized in that the aryl be selected from phenyl, naphthalene,
Xenyl, three and phenyl, anthryl, fluoranthene base, pyrenyl, phenanthryl, base and the aryl replace gained by the alkyl of C1-C12
Group.
3. as described in claim 12,4,6- trifluoromethyl pyridine compounds, which is characterized in that the heteroaryl is selected from (9,9- bis-
Alkyl) fluorenyl, (9,9- bis- replace or unsubstituted aryl) fluorenyl, dibenzothiophene, dibenzofuran group, pyridyl group,
Pyrimidine radicals, pyridazinyl, triazine radical, imidazole radicals, oxazolyls, thiazolyl, thiadiazolyl group, quinolyl, isoquinolyl, quinazolyl,
Quinoxalinyl, azepine dibenzofuran group, azepine dibenzothiophene, acridinyl, phenoxazines, phenoxazine thiophene and the heteroaryl
Base replaces gained group by the alkyl of C1-C12.
4. as described in claim 12,4,6- trifluoromethyl pyridine compounds, which is characterized in that be the chemical combination of following structural 1-44
Object：
5. application of the 2,4,6- trifluoromethyl pyridines compound 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, hole blocking layer, electron injecting layer, electron transfer layer, which is characterized in that institute
It states at least one layer in organic layer and contains 2,4,6- trifluoromethyl pyridines compound as described in claim 1.
7. organic electroluminescence device as claimed in claim 6, which is characterized in that described in claim 12,4,6- trifluoros
Layer where pyridine compounds is luminescent layer or electron transfer layer.
8. organic electroluminescence device as claimed in claim 6, which is characterized in that described in claim 12,4,6- trifluoros
Pyridine 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
2,4, the 6- trifluoromethyl pyridine compounds of structural formula 1-44 described in 4, or simultaneously using two or more selected from as claimed in claim 4
Structural formula 1-44 2,4,6- trifluoromethyl pyridine compounds.
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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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1845980A (en) * | 2003-09-05 | 2006-10-11 | 西巴特殊化学品控股有限公司 | Electroluminescent device |
| CN102781918A (en) * | 2010-02-25 | 2012-11-14 | 保土谷化学工业株式会社 | Substituted pyridyl compound and organic electroluminescent element |
| CN105294663A (en) * | 2015-11-11 | 2016-02-03 | 上海道亦化工科技有限公司 | Pyridine-containing compound and organic light-emitting device |
-
2018
- 2018-03-27 CN CN201810258776.1A patent/CN108470828A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1845980A (en) * | 2003-09-05 | 2006-10-11 | 西巴特殊化学品控股有限公司 | Electroluminescent device |
| CN102781918A (en) * | 2010-02-25 | 2012-11-14 | 保土谷化学工业株式会社 | Substituted pyridyl compound and organic electroluminescent element |
| CN105294663A (en) * | 2015-11-11 | 2016-02-03 | 上海道亦化工科技有限公司 | Pyridine-containing compound and organic light-emitting device |
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Application publication date: 20180831 |