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CN107721979A - A kind of organic electroluminescent compounds and its organic electroluminescence device based on pyridine and triazine - Google Patents

A kind of organic electroluminescent compounds and its organic electroluminescence device based on pyridine and triazine Download PDF

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Publication number
CN107721979A
CN107721979A CN201710935488.0A CN201710935488A CN107721979A CN 107721979 A CN107721979 A CN 107721979A CN 201710935488 A CN201710935488 A CN 201710935488A CN 107721979 A CN107721979 A CN 107721979A
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organic
compound
electroluminescence device
pyridine
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黄锦海
苏建华
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Shanghai Taoe Chemical Technology Co Ltd
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Abstract

The invention provides a kind of organic electroluminescent compounds based on pyridine and triazine, it has following structure：The compound has preferable heat endurance, high-luminous-efficiency and high luminance purity, can be used for making organic electroluminescence device, organic solar batteries, OTFT or organophotoreceptorswith field.Present invention also offers a kind of organic electroluminescence device, the device includes at least one layer in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer or electron transfer layer, organic layer includes compound just like structural formula I, and the organic electroluminescence device has that electroluminescent efficiency is good and excitation is excellent and the advantages of long lifespan.

Description

A kind of organic electroluminescent compounds and its organic electroluminescence hair based on pyridine and triazine Optical device
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of to be sent out based on pyridine and the organic electroluminescence of triazine Luminescent material and its organic electroluminescence device, belong to organic electroluminescence device display technology field.
Background technology
Organic electroluminescence device (OLEDs) is by spin coating or vacuum evaporation deposition one between two metal electrodes 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.Hole follows the electronics as caused by negative electrode to be incorporated in through electron transfer layer through hole transmission layer as caused by anode Luminescent layer forms exciton, then lights.Organic electroluminescence device can be adjusted as desired by the material for changing luminescent layer Section launches the light of various needs.
Organic electroluminescence device has self-luminous, wide viewing angle, low energy consumption, efficiency as a kind of new Display Technique High, thin, rich in color, fast response time, Applicable temperature scope are wide, low driving voltage, can make flexible with it is transparent Display panel and the particular advantages such as environment-friendly, it can apply on flat-panel monitor and a new generation's illumination, can also conduct LCD backlight.
Since the invention at the bottom of the 1980s, organic electroluminescence device has industrially been applied, such as As screens such as camera and mobile phones, but current OLED, because efficiency is low, it is wider that the factors such as service life is short restrict it General application, particularly 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 when applying voltage-operated, Joule heat can be produced so that Organic material easily crystallizes, and have impact on life-span 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, due to speed of the speed of most electroluminescent organic material transporting holes than transmitting electronics It hurry up, easily cause the electronics and number of cavities imbalance of luminescent layer, the efficiency of such device is just than relatively low.Three (8-hydroxyquinolines) Aluminium (Alq3) since invention, it has been extensively studied, but as electron transport material its electron mobility still very Intrinsic characteristic that is low, and itself can degrading, in using its device as electron transfer layer, it may appear that the situation that voltage declines, Simultaneously as relatively low electron mobility so that substantial amounts of hole enters Alq3In layer, excessive hole is with non-luminescent shape Formula emittance, and when as electron transport material, due to the characteristic of its green light, be above restricted in application.Cause This, development stability and the electron transport material with larger electron mobility, widely uses to organic electroluminescence device With great value.
The content of the invention
Present invention firstly provides a kind of organic electroluminescent compounds based on pyridine and triazine, and it is with following structure The compound of Formulas I：
Wherein, R1And R2Independently selected from hydrogen, deuterium and substitution or unsubstituted C6-C30 aryl；
Ar1、Ar2Independently selected from substitution or unsubstituted C6-C30 aryl；
Py is pyridine radicals；
L is phenylene；
Z1And Z2Independently selected from N or CH.
Preferably, R1And R2Independently selected from hydrogen, deuterium, phenyl, naphthyl, three and phenyl, anthryl, phenanthryl, pyrenyl, base, glimmering Anthryl, (9,9- dialkyl group) fluorenyl, (9,9- bis- substitutes either unsubstituted aryl) fluorenyl, 9,9- be Spirofluorene-based, substitution or not Substituted dibenzothiophenes base and substitution or unsubstituted dibenzofuran group, above aryl and heteroaryl can also be further Substitute for C1-C12 alkyl；
Ar1And Ar2Independently selected from phenyl or xenyl.
The organic electroluminescent compounds for being preferably based on pyridine and triazine are following structural 1-71 compound：
The present invention the organic electroluminescent compounds based on pyridine and triazine can apply organic electroluminescence device, Organic solar batteries, OTFT or organophotoreceptorswith field.
Present invention also offers a kind of organic electroluminescence device, the device includes anode, negative electrode and organic layer, organic layer Comprising at least one layer of in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer or electron transfer layer, At least one layer contains the compound as described in structural formula I in wherein described organic layer：
Wherein Ar1-Ar2、R1-R2、Py、Z1-Z2It is defined as described above with L.
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 stop 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；
Wherein, the layer where the compound as described in structural formula I is electron transfer layer or electron injecting layer；
The compound that compound as described in structural formula I is structural formula 1-71；
Compound as described in structural formula I can be used alone, and can also be used in mixed way with other compounds；Such as structural formula Compound described in I can be used alone a kind of compound therein, can also use two kinds or two kinds in structural formula I simultaneously Compound above.
The organic electroluminescence device of the present invention, further preferred mode are that the organic electroluminescence device includes sun In pole, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, wherein electron transfer layer or electron injecting layer Compound containing structural formula I；It is further preferred that the compound in electron transfer layer or electron injecting layer is structural formula 1- 71 compound.
The organic electroluminescence device of the present invention, can also also serve as electricity when structural formula I compound is as electron transfer layer Sub- implanted layer.
The gross 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, gold-tinted, 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, effectively hole can be transferred on luminescent layer from anode.Other small molecules can be included and macromolecule is organic Compound, including but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanine Class compound, six cyano group, six miscellaneous triphen (hexanitrilehexaazatriphenylene), 2,3,5,6- tetra- fluoro- 7,7', 8, The cyanogen dimethyl-parabenzoquinones (F4-TCNQ) of 8'- tetra-, PVK, 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 adjust as needed The scope of visible ray.Following compound, including but not limited to naphthalene compounds, pyrene compound, fluorenes class chemical combination can be contained Thing, 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 Thing uses.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires good electronic transmission performance, energy It is enough effectively electronics from cathode transport to luminescent layer in, there is very big electron mobility.There is structural formula I except the present invention Outside compound, it is also an option that or the following compound of collocation, but not limited to this, oxa- oxazole, thiazole compound, three nitrogen Azole compounds, three nitrogen piperazine class compounds, triazine class compound, quinoline class compound, phenodiazine anthracene compound, containing sila Cyclics, quinolines, ferrosin class compound, metallo-chelate (such as Alq3,8-hydroxyquinoline lithium), fluorine substitution Benzene-like compounds, benzimidazoles compound.
The electron injecting layer of organic electroluminescence device of the present invention, electronics effectively can be injected into organic layer from negative electrode In, in addition to the present invention is with Compounds of structural formula I, the compound of alkali metal or alkali metal is mainly selected from, or selected from alkaline earth The compound or alkali metal complex of metal either alkaline-earth metal, can select following compound, but not limited to this, alkali gold Category, alkaline-earth metal, rare earth metal, oxide either halide, the oxide of alkaline-earth metal or halide, the rare earth of 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 somebody with somebody with other electroluminescent organic materials Close and use.
Each layer of organic layer in the organic electroluminescence device of the present invention, it 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.It can make for metal motor Prepared with vapour deposition method or sputtering method.
Device experimental shows, organic electroluminescent compounds based on pyridine and triazine of the present invention as described in structural formula I, With preferable heat endurance, high-luminous-efficiency, high luminance purity.The organic electroluminescence made using the organic electroluminescent compounds Luminescent device has that electroluminescent efficiency is good and excitation is excellent and the advantages of long lifespan.
Brief description of the drawings
Fig. 1 is a kind of organic electroluminescence device structural representation of the present invention,
Wherein, 110 glass substrate is represented as, 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 negative electrode.
Embodiment
In order to describe the present invention in more detail, especially exemplified by example below, but not limited to this.
The synthesis of intermediate
The synthesis of intermediate A
In flask, the addition bromo- 2- chloroiodobenzones (25g, 79.4mmol) of 4-, 3- pyridine boronic acids pinacol ester (16.3g, 79.4mmol), potassium carbonate (22g, 160mmol), tetrahydrofuran (300mL), water (100mL), tetra-triphenylphosphine palladium (1g), in nitrogen It is heated to reflux under gas shielded 10 hours, cools down, extracted with dichloromethane, dried, concentration, crude product is purified through column chromatography and produced Thing 14.2g, yield 67%.
Intermediate 1-1 synthesis
In flask, addition intermediate A (2g, 7.5mmol), 1- naphthalene boronic acids (1.3g, 7.5mmol), potassium carbonate (2g, 15mmol), tetrahydrofuran (20mL), water (10mL), tetra-triphenylphosphine palladium (0.2g), it is small that 10 is heated to reflux under nitrogen protection When, cooling, extracted, dried with dichloromethane, concentration, crude product purifies to obtain product 1.8g, yield 76% through column chromatography.
With similar intermediate 1-1 synthetic method, other following intermediates are prepared, such as table 1：
Table 1
Embodiment 1
The synthesis of compound 2
In flask, addition intermediate 1-1 (1.8g, 5.7mmol), 2,4- diphenyl -6- [3- (4,4,5,5- tetramethyls - 1,3,2- dioxaborolanes -2- bases) phenyl] -1,3,5-triazines (2.5g, 5.7mmol), potassium carbonate (1.6g, 11.5mmol), tetrahydrofuran (20mL), water (10mL), palladium (0.1g), X-Phos (0.2g), nitrogen protection is lower to heat back Stream 24 hours, cooling, is extracted with dichloromethane, is dried, and concentration, crude product purifies to obtain product 1.8g, yield through column chromatography 55%.
Other following compounds are prepared with similar synthetic method, see the table below：
Table 2
Intermediate 2-1 synthesis
In flask, the bromo- iodobenzenes of the chloro- 4- of 3- (5g, 15.9mmol), 1- naphthalene boronic acids (2.7g, 15.9mmol), carbonic acid are added Potassium (4.4g, 32mmol), tetrahydrofuran (30mL), water (15mL), tetra-triphenylphosphine palladium (0.3g), it is heated to reflux under nitrogen protection 5 hours, cooling, extracted, dried with dichloromethane, concentration, crude product purifies to obtain product 3.2g, yield 63% through column chromatography.
Intermediate listed in table 3 is synthesized with similar synthetic method：
Table 3
Intermediate 3-1 synthesis
In flask, addition intermediate 2-1 (3g, 9.5mmol), 2,4- diphenyl -6- [3- (4,4,5,5- tetramethyl -1, 3,2- dioxaborolanes -2- bases) phenyl] -1,3,5-triazines (4.4g, 9.5mmol), potassium carbonate (2.8g, 20mmol), four Hydrogen furans (30mL), water (15mL), tetra-triphenylphosphine palladium (0.3g), it is heated to reflux 5 hours under nitrogen protection, cools down, use dichloro Methane extracts, and dries, and concentration, crude product purifies to obtain product 3.7g, yield 72% through column chromatography.
The intermediate of following table is prepared with similar synthetic method：
Table 4
Embodiment 9
The synthesis of compound 27
In flask, addition intermediate 3-1 (3g, 5.5mmol), 3- pyridine boronic acids pinacol ester (1.3g, 6.6mmol), Potassium carbonate (1.5g, 11mmol), dioxane (20mL), water (10mL), palladium (0.1g), X-Phos (0.2g), in nitrogen Under protection, it is heated to reflux 24 hours, cools down, extracted with dichloromethane, purify to obtain yield 1.6g, yield 48% through column chromatography.
Other compounds in table 5 are prepared with similar synthetic method：
Table 5
Embodiment 13-24
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) pass through successively：Deionized water, ethanol, acetone and deionized water are cleaned, then with oxygen plasma treatment 30 seconds.
Then, NPB is deposited, forms the thick hole transmission layers 130 of 60nm.
Then, the thick Alq of 37.5nm are deposited on hole transmission layer31%C545T is adulterated as luminescent layer 140.
Then, 37.5nm thickness the compounds of this invention is deposited on luminescent layer as electron transfer layer 150.
Finally, evaporation 1nm LiF are electron injecting layer 160 and 100nm Al as device cathodes 170.
Prepared device (structural representation is shown in Fig. 1) with Photo Research PR650 spectrometers measure 20mA/cm2Current density under efficiency such as table 6.
Comparative example 1
Except electron transfer layer Alq3Or ET1Outside instead of the compounds of this invention, others are as embodiment 13-24. Prepared device (structural representation is shown in Fig. 1) with Photo Research PR650 spectrometers measure in 20mA/cm2Electricity Efficiency such as table 6 under current density.
Table 6
Under the same conditions, being had based on prepared by pyridine and the organic electroluminescent compounds of triazine using the present invention The efficiency of organic electroluminescence devices is higher than comparative example, as described above, the compound of the present invention has high stability, present invention system Standby organic electroluminescence device has high efficiency and optical purity.
The structural formula of compound described in device is as follows：
Preferred embodiment of the invention described in detail above.It should be appreciated that one of ordinary skill in the art without Creative work can is needed to make many modifications and variations according to the design of the present invention.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 scheme, all should be in the protection domain being defined in the patent claims.

Claims (8)

1. a kind of organic electroluminescent compounds based on pyridine and triazine, it is characterised in that be the change with following structural formula I Compound：
Wherein, R1And R2Independently selected from hydrogen, deuterium and substitution or unsubstituted C6-C30 aryl；
Ar1、Ar2Independently selected from substitution or unsubstituted C6-C30 aryl；
Py is pyridine radicals；
L is phenylene；
Z1And Z2Independently selected from N or CH.
2. the organic electroluminescent compounds based on pyridine and triazine as claimed in claim 1, it is characterised in that R1And R2Solely On the spot selected from hydrogen, deuterium, phenyl, naphthyl, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (9,9- bis- substitutes either unsubstituted aryl) fluorenyl, 9,9- be Spirofluorene-based, substitution or unsubstituted dibenzothiophenes base and takes Generation or unsubstituted dibenzofuran group, above aryl and heteroaryl further can also substitute for C1-12 alkyl；
Ar1And Ar2Independently selected from phenyl or xenyl.
3. the organic electroluminescent compounds based on pyridine and triazine as claimed in claim 1, it is characterised in that be following knot Structure formula 1-71 compound：
4. a kind of organic electroluminescence device, the device includes anode, negative electrode and organic layer, and organic layer includes luminescent layer, hole At least one layer in implanted layer, hole transmission layer, hole blocking layer, electron injecting layer or electron transfer layer, it is characterised in that institute State at least one layer Organic Electricity based on pyridine and triazine contained as described in any one in claims 1 to 3 in organic layer Electro luminescent compounds.
5. organic electroluminescence device as claimed in claim 4, it is characterised in that as described in structural formula I based on pyridine and Layer where the organic electroluminescent compounds of triazine is at least one layer in electron transfer layer, electron injecting layer.
6. organic electroluminescence device as claimed in claim 4, it is characterised in that as described in structural formula I based on pyridine and The organic electroluminescent compounds of triazine are structural formula 1-71 compound.
7. organic electroluminescence device as claimed in claim 4, it is characterised in that as described in structural formula I based on pyridine and A kind of compound therein is used alone in the organic electroluminescent compounds of triazine, or uses two kinds in structural formula I simultaneously Compound above, or be used in mixed way with other compounds.
8. organic electroluminescence device as claimed in claim 4, it is characterised in that the organic electroluminescence device organic layer Gross thickness be 1-1000nm.
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