CN105153130B - Triazine derivative electron transport compound and its organic electroluminescence device - Google Patents
Triazine derivative electron transport compound and its organic electroluminescence device Download PDFInfo
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Abstract
The present invention provides a kind of triazine derivative organic electroluminescent compounds such as structural formula I, the compound has preferable thermal stability, high-luminous-efficiency, high luminance purity, it can be used for making organic electroluminescence device, be applied to organic solar batteries, Organic Thin Film Transistors or organophotoreceptorswith field.The present invention also provides a kind of organic electroluminescence devices, it includes anode, cathode and organic layer, organic layer is comprising one or more layers in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, at least one layer of compound comprising just like structural formula I in organic layer.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of organic electroluminescent of triazine derivative
Compound and its organic electroluminescence device belong to organic electroluminescence device field of display technology.
Background technique
Organic electroluminescence device (OLEDs) is between two metal electrodes by spin coating or vacuum evaporation deposition one
The device that layer organic material is prepared, a classical three layer organic electroluminescence device include hole transmission layer, luminescent layer
And electron transfer layer.The electronics generated by cathode is followed to be incorporated in through electron transfer layer through hole transmission layer in the hole generated by anode
Luminescent layer forms exciton, then shines.Organic electroluminescence device can according to need the material by changing luminescent layer to adjust
Section emits the light of various needs.
Organic electroluminescence device has self-luminous, wide viewing angle, low energy consumption, efficiency as a kind of novel display technology
High, thin, rich in color, fast response time, Applicable temperature range be wide, low driving voltage, can make flexible and transparent
Display panel and the particular advantages such as environmental-friendly can be applied on flat-panel monitor and a new generation's illumination, be can also be used as
The backlight of LCD.
Since the invention at the bottom of the 1980s, organic electroluminescence device is industrially applied, such as
As screens such as camera and mobile phones, but current OLED device, due to low efficiency, it is wider that the factors such as service life is short restrict it
General application, especially large screen display.And restricting one of key factor is exactly in organic electroluminescence device
The performance of electroluminescent organic material.Additionally, due to OLED device when applying voltage-operated, Joule heat can be generated, so that
Organic material is easy to happen crystallization, affects service life and the efficiency of device, therefore, it is also desirable to develop the organic electroluminescence of stability and high efficiency
Luminescent material.
Speed in OLED material, due to the speed of most electroluminescent organic material transporting holes than transmitting electronics
Fastly, it be easy to cause the electrons and holes quantity of luminescent layer uneven, the efficiency of such device is with regard to relatively low.Three (8-hydroxyquinolines)
Aluminium (Alq3) since the invention, it has been extensively studied, but still very as electron transport material its electron mobility
Intrinsic characteristic that is low, and itself can degrading, in using its device as electron transfer layer, it may appear that the case where voltage declines,
Simultaneously as lower electron mobility, so that a large amount of hole enters Alq3In layer, excessive hole is with non-luminescent shape
Formula radiation energy, and when as electron transport material, due to the characteristic of its green light, above it is restricted in application.Cause
This, organic electroluminescence device is widely used in development stability and the electron transport material with larger electron mobility
With great value.
Summary of the invention
Present invention firstly provides a kind of triazine derivative organic electroluminescent electron-transport materials, for as follows
The compound of structural formula I:
Wherein, R1、R2、R3、R4Separately it is selected from hydrogen, D-atom, the alkyl of C1-C12, the alkoxy of C1-C8, C6-
The substitution of C30 or unsubstituted aryl；
L be selected from singly-bound, the alkyl of C1-C6, the substituted or unsubstituted aryl of C6-C30, C3-C30 substitution or do not take
The heteroaryl in generation；
A is selected from O, S, Se, SO, SO2。
Preferably, R1、R2、R3、R4Separately it is selected from C1-C8 alkyl, the substitution of C6-C30 or unsubstituted virtue
Base；
L is selected from the substituted or unsubstituted aryl of singly-bound, C6-C30；
A is selected from O, S.
It is highly preferred that R1、R2、R3、R4Separately it is selected from methyl, ethyl, propyl, isopropyl, tert-butyl, positive fourth
Base, n-hexyl, phenyl, naphthalene, xenyl；
L is selected from singly-bound, phenyl ring, xenyl.
It is further preferred that triazine derivative of the invention is the compound of following structural 1-16:
The organic electroluminescent electron transport material of triazine derivative of the invention can be applied in organic electroluminescent
Device, organic solar batteries, Organic Thin Film Transistors or organophotoreceptorswith field.
The present invention also provides a kind of organic electroluminescence device, which includes anode, cathode and organic layer, organic layer
Include one layer or one in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer
Layer or more, wherein at least one layer organic electroluminescence hair containing the triazine derivative as described in structural formula I in the organic layer
Photoelectron transfer material:
Wherein R1-R4, L, A it is defined as described above.
Wherein organic layer is luminescent layer and electron transfer layer；
Or organic layer is luminescent layer, hole injection layer, hole transmission layer and electron transfer layer；
Or organic layer is luminescent layer, hole injection layer, hole transmission layer, electron transfer layer and electron injecting layer；Or
Organic layer is luminescent layer, hole transmission layer, electron transfer layer and electron injecting layer；
Or organic layer is luminescent layer, hole transmission layer and electron injecting layer.
Preferably, wherein the layer where triazine derivative as described in structural formula I is electron transfer layer or electron injection
Layer；
Preferably, the compound that wherein triazine derivative described in structural formula I is structural formula 1-16；
When triazine derivative as described in structural formula I is prepared for luminescent device, can be used alone, can also and its
He is used in mixed way compound；Triazine derivative as described in structural formula I can be used alone one such compound, can also
Simultaneously using two or more the compound in structural formula I.
Organic electroluminescence device of the invention, further preferred mode are that the organic electroluminescence device includes sun
Pole, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and cathode, wherein in electron transfer layer or electron injecting layer
Compound containing structural formula I；It is further preferred that the compound contained in electron transfer layer or electron injecting layer is structural formula
The compound of 1-16.
In organic electroluminescence device of the invention, electricity can also be also served as when Compounds of structural formula I is as electron transfer layer
Sub- implanted layer.
The overall thickness of organic electroluminescence device organic layer of the invention is 1-1000nm, preferably 50-500nm.
When having the compound of structural formula I using the present invention, can arrange in pairs or groups makes organic electroluminescence device of the invention
With other materials, such as in hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and hole blocking layer
It is medium, 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 is closed including other small molecules and macromolecular organic
Object, including but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanines
Close object, the miscellaneous triphen (hexanitrilehexaazatriphenylene) of six cyano six, 2,3,5,6- tetra- fluoro- 7,7', 8,8'- tetra-
Cyanogen dimethyl-parabenzoquinone (F4-TCNQ), polyvinyl carbazole, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of organic electroluminescence device of the invention has the good characteristics of luminescence, can be adjusted according to the needs
The range of visible light.Following compound, including but not limited to naphthalene compounds, pyrene compound, fluorenes class chemical combination can be contained
Object, bends class compound, glimmering anthracene compound, anthracene compound, pentacene class compound, class compound, two at luxuriant and rich with fragrance class compound
Aromatic ethylene class compound, triphenylamine ethylene compounds, aminated compounds, carbazole compound, benzimidazoles compound, furan
Class of muttering compound, metal organic fluorescence complex compound, metal Phosphorescent complex compound (such as Ir, Pt, Os, Cu, Au), polyethylene click
The organic polymer luminescent materials such as azoles, poly-organosilicon compound, polythiophene, they can be used alone, and a variety of can also mix
Object uses.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires good electronic transmission performance, energy
It reaches in effectively electronics from cathode transport to luminescent layer, there is very big electron mobility.Except of the invention has structural formula I
Outside compound, it is also an option that 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, except it is of the invention there is Compounds of structural formula I in addition to, be mainly selected from the compound of alkali metal or alkali metal, or be selected from alkaline earth
The compound or alkali metal complex of metal or alkaline-earth metal, can choose following compound, but not limited to this: alkali gold
Category, alkaline-earth metal, rare earth metal, the oxide of alkali metal or halide, the oxide of alkaline-earth metal or halide, rare earth
The organic complex of the oxide or halide of metal, alkali metal or alkaline-earth metal；Preferably lithium, lithium fluoride, lithia,
Lithium nitride, 8-hydroxyquinoline lithium, caesium, cesium carbonate, 8-hydroxyquinoline caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate,
Magnesia, these compounds, which can be used alone, to be used with mixture, can also match with other electroluminescent organic materials
It closes and uses.
Each layer of organic layer in organic electroluminescence device of the invention can be steamed by vacuum vapour deposition, molecular beam
It is prepared by the modes such as plating method, the dip coating for being dissolved in solvent, spin-coating method, stick coating method or inkjet printing.Metal motor can be made
It is prepared with vapour deposition method or sputtering method.
Device experimental shows that triazine derivative of the present invention as described in structural formula I has preferable thermal stability, and height shines
Efficiency, high luminance purity.Have electroluminescent efficiency good and colour purity using the device of organic electroluminescent compounds production
Spend the advantage of length of excellent and service life.
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 synthesis of compound 1
The synthesis of intermediate A
In three-necked flask, bromo- 9, the 9- dimethyl fluorene (5.5g, 20mmol) of 2- is added, magnesium chips (0.86g, 36mmol), does
Dry tetrahydrofuran 60ml and 3 iodine, are heated to reflux 1 hour.Under ice bath, this reaction solution is added drop-wise to dissolved with equal trichlorine piperazine
It in the tetrahydrofuran solution of (1.8g, 10mmol), drips off, is heated to 50 degree and reacts 12 hours, it is cooling, it is slowly added to ammonium chloride water
Solution is extracted with dichloromethane, then is dried, filtered with anhydrous sodium sulfate, concentration, and organic layer obtains 7.5g through column chromatographic purifying and produces
Product, yield 75%.
The synthesis of compound 1
In three-necked flask, intermediate A (1.5g, 3mmol), 4- dibenzofurans boric acid (0.84g, 4mmol), carbon is added
Sour potassium (0.82g, 6mmol), the tetrahydrofuran of 20ml, the water of 10ml and four triphenyl phosphorus palladiums (50mg) return under nitrogen protection
Stream 24 hours, it is cooling, it is extracted with chloroform, is dried, filtered with anhydrous sodium sulfate, be concentrated to get crude product, crude product is through column chromatographic purifying
Obtain 1.3g product, yield 68%.
Embodiment 2
The synthesis of compound 9
In three-necked flask, intermediate A (1.5g, 3mmol), 4- dibenzothiophenes boric acid (0.91g, 4mmol), carbon is added
Sour potassium (0.82g, 6mmol), the tetrahydrofuran of 20ml, the water of 10ml and four triphenyl phosphorus palladiums (50mg) return under nitrogen protection
Stream 24 hours, it is cooling, it is extracted with chloroform, is dried, filtered with anhydrous sodium sulfate, be concentrated to get crude product, crude product is through column chromatographic purifying
Obtain 1.1g product, yield 58%.
Embodiment 3
The synthesis of compound 13
In three-necked flask, be added intermediate A (1.5g, 3mmol), 3- (4- dibenzothiophenes)-phenyl boric acid (1.2g,
4mmol), potassium carbonate (0.82g, 6mmol), the tetrahydrofuran of 20ml, the water of 10ml and four triphenyl phosphorus palladiums (50mg), in nitrogen
Under protection, flow back 24 hours, it is cooling, it is extracted with chloroform, is dried, filtered with anhydrous sodium sulfate, be concentrated to get crude product, crude product is through column
Chromatographic purifying obtains 1.0g product, yield 45%.
Embodiment 4
The preparation of organic electroluminescence device
OLED is prepared using the compound 1 of embodiment 1.
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, in NPB, the hole transmission layer 130 of 60nm thickness is formed.
Then, the Alq for crossing 37.5nm thickness is steamed on the hole transport layer31%C545T is adulterated as luminescent layer 140.
Then, the compound 1 and Liq for 37.5nm thickness being deposited on the light-emitting layer are as electron transfer layer 150,1 He of compound
The ratio of Liq is 1:1.
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) is measured with Photo Research PR650 spectrometer in 20mA/
cm2Current density under power efficiency be 6.9lm/W, emit green light.
Embodiment 5
Other than electron transfer layer replaces compound 1 with compound 9, others are as embodiment 4.
Prepared device is in 20mA/cm2Current density under power efficiency be 7.1lm/W, emit green light.
Embodiment 6
Other than electron transfer layer replaces compound 1 with compound 13, others are as embodiment 4.
Prepared device is in 20mA/cm2Current density under power efficiency be 6.7lm/W, emit green light.
Comparative example 1
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 for crossing 37.5nm thickness is steamed on the hole transport layer31%C545T is adulterated as luminescent layer 140.
Then, the Alq of 37.5nm thickness is deposited on the light-emitting layer3As electron transfer layer 150.
Finally, vapor deposition 1nm LiF is electron injecting layer 160 and 100nm Al as device cathodes 170.
Prepared device is measured with Photo Research PR650 spectrometer in 20mA/cm2Current density under
Power efficiency is 5.0lm/W, emits green light.
Under the same conditions, the organic electroluminescent prepared using organic electroluminescent electron transport material of the invention
The efficiency of device is higher than comparative example, as described above, the compound of the present invention has high stability, Organic Electricity prepared by the present invention
Electroluminescence device has high efficiency and optical purity.
The structural formula of compound described in device is as follows:
The preferred embodiment of the present invention has been described in detail above.It should be appreciated that the ordinary skill of this field is without wound
The property made labour, which according to the present invention can conceive, makes many modifications and variations.Therefore, all technician in the art
Pass through the available technology of logical analysis, reasoning, or a limited experiment on the basis of existing technology under this invention's idea
Scheme, all should be within the scope of protection determined by the claims.
Claims (8)
1. a kind of triazine derivative organic electroluminescent compounds, it is characterised in that it is the chemical combination for having the following structure Formulas I
Object:
Wherein, R1-R4For methyl；
L is selected from singly-bound or phenyl；
A is selected from O or S.
2. triazine derivative organic electroluminescent compounds according to claim 1, it is characterised in that it is following knot
The compound of structure formula 1-16:
3. a kind of organic electroluminescence device comprising anode, cathode and organic layer, organic layer include luminescent layer, hole injection
It is layer, hole transmission layer, hole blocking layer, electron injecting layer, one or more layers in electron transfer layer, it is characterised in that have
At least one layer includes triazine derivative as described in claim 1 in machine layer.
4. organic electroluminescence device according to claim 3, it is characterised in that the triazines as described in structural formula I are derivative
Layer where object is electron transfer layer or electron injecting layer.
5. organic electroluminescence device according to claim 3, it is characterised in that the triazines as described in structural formula I are derivative
Object is used alone, or is used in mixed way with other compounds.
6. organic electroluminescence device according to claim 3, it is characterised in that the triazines as described in structural formula I are derivative
One such compound is used alone in object, or simultaneously using two or more the compound in structural formula I.
7. organic electroluminescence device according to claim 3, it includes anode, hole transmission layer, luminescent layer, electronics to pass
Defeated layer, electron injecting layer and cathode, it is characterised in that the chemical combination containing structural formula I in electron transfer layer and/or electron injecting layer
Object.
8. organic electroluminescence device according to claim 3, it includes anode, hole transmission layer, luminescent layer, electronics to pass
Defeated layer, electron injecting layer and cathode, it is characterised in that the compound contained in electron transfer layer and/or electron injecting layer is as weighed
Benefit requires the compound of the 2 structural formula 1-16.
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| CN107068879B (en) * | 2016-04-25 | 2020-09-22 | 中节能万润股份有限公司 | Organic electroluminescent device containing triazine compounds and application thereof |
| KR102054276B1 (en) | 2016-06-29 | 2019-12-10 | 삼성에스디아이 주식회사 | Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device |
| KR102027961B1 (en) | 2016-06-29 | 2019-10-02 | 삼성에스디아이 주식회사 | Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device |
| KR102050000B1 (en) | 2016-07-12 | 2019-11-28 | 삼성에스디아이 주식회사 | Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device |
| KR102054277B1 (en) | 2016-07-29 | 2019-12-10 | 삼성에스디아이 주식회사 | Composition for organic optoelectronic device and organic optoelectronic device and display device |
| KR101939152B1 (en) * | 2016-09-12 | 2019-01-16 | (주)씨엠디엘 | Fluorenyl triazine derivative organic compound and organic electroluminescent device including the same |
| WO2018128255A1 (en) * | 2017-01-05 | 2018-07-12 | 삼성에스디아이 주식회사 | Compound for organic optoelectronic element, composition for organic optoelectronic element, organic optoelectronic element, and display device |
| US11158817B2 (en) | 2017-01-05 | 2021-10-26 | Samsung Sdi Co., Ltd. | Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device |
| CN107501302A (en) * | 2017-08-11 | 2017-12-22 | 长春海谱润斯科技有限公司 | A kind of 1,3,5 pyrrolotriazine derivatives and its application |
| EP3503240A1 (en) * | 2017-12-21 | 2019-06-26 | Novaled GmbH | Organic semiconductor layer |
| CN111004219B (en) * | 2019-12-26 | 2020-12-08 | 陕西莱特迈思光电材料有限公司 | Compound, organic electroluminescent device, and display device |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1789252A (en) * | 2005-12-29 | 2006-06-21 | 中国科学院上海有机化学研究所 | Novel blue light material-thiotrzinone-containing anthracene derivatives |
| CN1950479A (en) * | 2004-04-29 | 2007-04-18 | 西巴特殊化学品控股有限公司 | Electroluminescent device |
| CN103325950A (en) * | 2012-03-22 | 2013-09-25 | 陶氏环球技术有限责任公司 | Charge transport layers and films containing the same |
| WO2015000549A1 (en) * | 2013-07-02 | 2015-01-08 | Merck Patent Gmbh | Materials for electronic devices |
| WO2015073343A1 (en) * | 2013-11-12 | 2015-05-21 | Dow Global Technologies Llc | Compositions containing fluorene substituted triazine derived compounds, and electronic devices containing the same |
-
2015
- 2015-08-03 CN CN201510481602.8A patent/CN105153130B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1950479A (en) * | 2004-04-29 | 2007-04-18 | 西巴特殊化学品控股有限公司 | Electroluminescent device |
| CN1789252A (en) * | 2005-12-29 | 2006-06-21 | 中国科学院上海有机化学研究所 | Novel blue light material-thiotrzinone-containing anthracene derivatives |
| CN103325950A (en) * | 2012-03-22 | 2013-09-25 | 陶氏环球技术有限责任公司 | Charge transport layers and films containing the same |
| WO2015000549A1 (en) * | 2013-07-02 | 2015-01-08 | Merck Patent Gmbh | Materials for electronic devices |
| WO2015073343A1 (en) * | 2013-11-12 | 2015-05-21 | Dow Global Technologies Llc | Compositions containing fluorene substituted triazine derived compounds, and electronic devices containing the same |
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