CN107033143A - Compound and its organic electroluminescence device containing [1,2,4] triazole [1,5 a] pyridine - Google Patents

Compound and its organic electroluminescence device containing [1,2,4] triazole [1,5 a] pyridine Download PDF

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Publication number
CN107033143A
CN107033143A CN201710413701.1A CN201710413701A CN107033143A CN 107033143 A CN107033143 A CN 107033143A CN 201710413701 A CN201710413701 A CN 201710413701A CN 107033143 A CN107033143 A CN 107033143A
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compound
organic
pyridine
triazole
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黄锦海
苏建华
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Shanghai Taoe Chemical Technology Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

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  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

Contain [1 the invention provides one kind, 2,4] triazole [1,5 a] pyridine organic electroluminescent electron transport compound, the compound has preferable heat endurance, high-luminous-efficiency, high luminance purity, it can be used for making organic electroluminescence device, applied to organic solar batteries, OTFT or organophotoreceptorswith field.Present invention also offers a kind of organic electroluminescence device, it includes anode, negative electrode and organic layer, organic layer includes at least one layer of compound comprising just like structural formula I at least one layer in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, organic layer.

Description

Compound and its organic electroluminescent containing [1,2,4]-triazole [1,5-a] pyridine Device
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to one kind contains [1,2,4]-triazole [1,5-a] pyrrole The compound and its organic electroluminescence device of pyridine, 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 from, a classical three layer organic electroluminescence device includes hole transmission layer, luminescent layer And electron transfer layer.The hole produced by anode through hole transmission layer with the electronics that is produced by negative electrode through combined with electron transfer layer Luminescent layer formation exciton, then lights.Organic electroluminescence device can be adjusted as desired by the material of luminescent layer is changed The light of the various needs of section transmitting.
Organic electroluminescence device is as a kind of new Display Technique, with self-luminous, wide viewing angle, low energy consumption, efficiency High, thin, rich 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, can be applied on flat-panel monitor and a new generation's illumination, can also conduct LCD backlight.
Since invention at the bottom of 1980s, organic electroluminescence device has industrially been applied, such as As screens such as camera and mobile phones, but current OLED is low due to efficiency, and it is wider that the factor such as service life is short restricts it General application, particularly large screen display, it is therefore desirable to improve the efficiency of device.And restrict one of key factor just It is the performance of the electroluminescent organic material in organic electroluminescence device.Applying voltage-operated additionally, due to OLED When, Joule heat can be produced so that organic material is easily crystallized, have impact on life-span and the efficiency of device, therefore, it is also desirable to Develop the electroluminescent organic material of stability and high efficiency.
In OLED material, due to speed of the speed than transmitting electronics of most electroluminescent organic material transporting holes It hurry up, the electronics and number of cavities for easily causing luminescent layer are uneven, and the efficiency of such device is just than relatively low.Three (8-hydroxyquinolines) Aluminium (Alq3) since the invention, it has been extensively studied, but as electron transport material its electron mobility still very It is low, and the intrinsic characteristic that itself can be degraded, in the device using it 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 the shape of non-luminescent 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 are widely used to organic electroluminescence device With great value.
The content of the invention
Present invention firstly provides a kind of organic electroluminescent electric transmission for containing [1,2,4]-triazole [1,5-a] pyridine Compound, it is the compound with following structural formula I：
Wherein, R1-R4Separately selected from hydrogen, deuterium, halogen, cyano group, straight chain or C1-C12 alkyl with side chain, straight Chain or C1-C8 alkoxyl, C6-C30 substitution or unsubstituted aryl with side chain, C3-C30 substitution or unsubstituted Heteroaryl, triaryl phosphinyl；
L is selected from singly-bound, C6-C30 substitution or unsubstituted aryl, C3-C30 substitution or unsubstituted contains one Individual or multiple heteroatomic heteroaryls；
Ar be selected from C6-C30 substitution or unsubstituted aryl, C3-C30 substitution or it is unsubstituted containing one or The multiple heteroatomic heteroaryls of person, triaryl phosphinyl；
Py is pyridine radicals；
Ar1Selected from hydrogen, deuterium, C6-C30 substitution or unsubstituted aryl.
Preferably, R1-R4Separately it is selected from hydrogen, deuterium, fluorine, phenyl, naphthyl, phenanthryl, pyrenyl, xenyl, phenylnaphthalene Base, naphthylphenyl, pyridine radicals, diphenyl phenyl.
Preferably, L is selected from singly-bound, phenyl, naphthyl.
Preferably, Ar1Selected from hydrogen, phenyl, naphthyl.
Preferably, Ar be selected from benzene, naphthyl, anthryl, phenanthryl, pyrenyl, perylenes base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (9, 9- bis- replaces or unsubstituted aryl) fluorenyl, 9,9- Spirofluorene-based, dibenzothiophenes base, dibenzofuran group, xenyl, benzene Base naphthyl, naphthylphenyl, diphenyl base phenyl, pyridine radicals, quinolyl, pyrimidine radicals, triazine radical, thiazolyl, oxazolyl, triazole Base, quinoxalinyl, isoquinolyl, phenylpyridyl, pyridinylphenyl, bipyridyl, the above group can be further C1-C10 alkyl or alkoxy substitution.
It is further preferred that the present invention contains the organic electroluminescent electric transmission of [1,2,4]-triazole [1,5-a] pyridine Compound is following structural 1-54 compound：
The organic electroluminescent electron transport compound containing [1,2,4]-triazole [1,5-a] pyridine of the present invention can be answered Used in 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 Include at least one in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer Layer, wherein in the organic layer at least one layer containing containing [1,2,4]-triazole [1,5-a] pyridine as described in structural formula I Organic electroluminescent electron transport compound：
Wherein R1-R4、A1, Ar, Py and L 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 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.
Preferably, wherein containing the organic electroluminescent electronics of [1,2,4]-triazole [1,5-a] pyridine as described in structural formula I Layer where transport compound is electron transfer layer or electron injecting layer.
Preferably, the organic electroluminescent electronics containing [1,2,4]-triazole [1,5-a] pyridine is passed wherein described in structural formula I Defeated compound is structural formula 1-54 compound.
The organic electroluminescent electric transmission chemical combination containing [1,2,4]-triazole [1,5-a] pyridine as described in structural formula I When thing is used for luminescent device preparation, it can be used alone, can also be used in mixed way with other compounds；As described in structural formula I Electroluminescent compounds containing [1,2,4]-triazole [1,5-a] pyridine can be used alone a kind of compound therein, also may be used With simultaneously using the two or more compounds in structural formula I.
The organic electroluminescence device of the present invention, further preferred mode is 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 at least one structural formula I；It is further preferred that containing at least one in electron transfer layer or electron injecting layer Structural formula 1-54 compound.
The organic electroluminescence device of the present invention, Compounds of structural formula I is as can also also serve as electronics during electron transfer layer Implanted layer.
The gross thickness of the organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
The organic electroluminescence device of the present invention is when having structural formula I compound using the present invention, and can arrange in pairs or groups makes 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, 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, can effectively be transferred to hole on luminescent layer from anode.Small molecule can be included and macromolecular organic is closed Thing, including but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanines Compound, the miscellaneous triphen (hexanitrilehexaazatriphenylene) of six cyano group six, 2,3,5,6- tetra- fluoro- 7,7', 8,8'- tetra- Cyanogen dimethyl-parabenzoquinone (F4-TCNQ), PVK, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of the organic electroluminescence device of the present invention, with the good characteristics of luminescence, can be adjusted 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 in the wrong, glimmering anthracene compound, anthracene compound, pentacene class compound, perylene 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 is used.
The Organic Electron Transport Material requirement of organic electroluminescence device of the present invention has good electronic transmission performance, energy It is enough effectively electronics from cathode transport to luminescent layer in, with very big electron mobility.There is structural formula I except the present invention Chemical combination beyond the region of objective existence, it is also an option that or the following compound of arranging in pairs or groups, 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.
Electronics, effectively can be injected into organic layer by the electron injecting layer of organic electroluminescence device of the present invention 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 or alkaline-earth metal, can select 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 Oxide or halide, the organic complex of alkali metal or alkaline-earth metal of 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 Conjunction is used.
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.It can make for metal motor Prepared with vapour deposition method or sputtering method.
Device experimental shows, Organic Electricity containing [1,2,4]-triazole [1,5-a] pyridine of the present invention as described in structural formula I Photoluminescence electron transport compound has preferable heat endurance, high-luminous-efficiency, high luminance purity.Using this contain [1,2,4]- The organic electroluminescence device that the compound of triazole [1,5-a] pyridine makes has electroluminescent efficiency well and excitation is excellent And the advantage of long lifespan.
Brief description of the drawings
Fig. 1 is a kind of organic electroluminescence device structural representation of the 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 hair 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.
Embodiment 1
The synthesis of compound 4
Intermediate 4-1 synthesis
In flask, 2- amino -5- bromopyridines (10g, 58mmol), 4- biphenylboronic acids (11.4g, 58mmol), carbon are added Sour potassium (16g, 118mmol), tetra-triphenylphosphine palladium (0.5g), tetrahydrofuran (100mL) and water (50mL), nitrogen protection is lower to heat Backflow 12 hours, cooling, is extracted with dichloromethane, is dried, concentration, and crude product obtains 9g, yield 63% through column chromatography purifying.
Intermediate 4-2 synthesis
In flask, add 3,5- dibromos benzonitrile (3g, 11.6mmol), 4- (1- naphthyls)-phenyl boric acid (2.9g, 11.6mmol), potassium carbonate (4.1g, 30mmol), tetra-triphenylphosphine palladium (0.1g), tetrahydrofuran (30mL) and water (15mL), It is heated to reflux 12 hours under nitrogen protection, cools down, extracted with dichloromethane, dried, concentration, crude product is obtained through column chromatography purifying 2.5g, yield 57%.
Intermediate 4-3 synthesis
In single port bottle, intermediate 4-1 (2.5g, 10mmol), intermediate 4-2 (3.8g, 10mmol), cuprous bromide are added (0.18mmol, 27mg), phenanthroline (0.18mmol, 33mg), zinc iodide (0.37mmol, 118mg), o-dichlorohenzene (30mL), 150 degree of blowing air reacts 24 hours, is cooled to after room temperature and uses dchloromethane, is filtered to remove inorganic salts, filtrate is dense Column chromatography for separation is used after contracting, white solid 2.7g, yield 43% is obtained.
The synthesis of compound 4
In flask, add intermediate 4-3 (2.5g, 4mmol), 3- pyridine boronic acids (1g, 8mmol), potassium carbonate (1.3g, 10mmol), tetra-triphenylphosphine palladium (0.1g), tetrahydrofuran (20mL) and water (10mL), are heated to reflux 12 small under nitrogen protection When, cooling is extracted with dichloromethane, is dried, concentration, and crude product obtains 1.9g, yield 76% through column chromatography purifying.
Embodiment 2
The synthesis of compound 23
Intermediate 23-1 synthesis
In single port bottle, intermediate 4-1 (3g, 12mmol), 3,5- dibromos benzonitrile (3.1g, 12mmol), bromination are added Cuprous (0.18mmol, 27mg), phenanthroline (0.18mmol, 33mg), zinc iodide (0.37mmol, 118mg), o-dichlorohenzene (30mL), 150 degree of blowing air reacts 24 hours, is cooled to after room temperature and uses dchloromethane, is filtered to remove inorganic salts, filtrate is dense Column chromatography for separation is used after contracting, white solid 3g, yield 50% is obtained.
The synthesis of compound 23
In flask, add intermediate 23-1 (2.6g, 5.2mmol), 4- (3- pyridines)-phenyl boric acid (2.6g, 13mmol), Potassium carbonate (2.7g, 20mmol), tetra-triphenylphosphine palladium (0.1g), tetrahydrofuran (20mL) and water (10mL), under nitrogen protection It is heated to reflux 12 hours, cools down, extracted with dichloromethane, dry, concentration, crude product obtains 2.3g, yield through column chromatography purifying 68%.
Embodiment 3
The synthesis of compound 36
Intermediate 36-1 synthesis
Synthetic method is with intermediate 4-1, raw material is respectively 2- amino -5- bromopyridines and 3- biphenylboronic acids, and yield is 61%.
Intermediate 36-2 synthesis
Synthetic method with intermediate 36-1 with intermediate 23-1, being replaced outside intermediate 4-1, yield 52%.
The synthesis of compound 36
Synthetic method is with compound 23, raw materials used is intermediate 36-2 and 5- phenyl -2- pyridine pinacol boric acid Ester, yield 60%.
Embodiment 4
The synthesis of compound 45
Intermediate 45-1 synthesis
Synthetic method is with intermediate 4-1, raw materials used is 2- amino -4- bromopyridines and 1- naphthalene boronic acids, yield 75%. Intermediate 45-2 synthesis
Synthetic method is raw materials used that intermediate 4-1, yield 66% are replaced with intermediate 45-1 with intermediate 23-1. The synthesis of compound 45
Synthetic method is with as compound 23, raw materials used is intermediate 45-2 and 3- (3- pyridine radicals)-phenyl boric acid, production Rate 61%.
Embodiment 5-8
The preparation of organic electroluminescence device
OLED is prepared using the compound in the embodiment 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, the thick hole transmission layers 130 of 60nm are formed.
Then, the thick Alq of 37.5nm are deposited on hole transmission layer3Doping 1%C545T is used as luminescent layer 140.
Then, 37.5nm is deposited on luminescent layer thick as electron transfer layer 150, comprising 75% the compounds of this invention and 25% LiQ.
Finally, evaporation 1nm LiF are that electron injecting layer 160 and 100nm Al are used as device cathodes 170.
Prepared device (structural representation is shown in Fig. 1) measured with Photo Research PR650 spectrometers 20mA/cm2Current density under power efficiency it is as shown in table 1.
Comparative example
Except electron transfer layer Alq3Outside instead of the compounds of this invention, others are with embodiment 5-8.
Prepared device (structural representation is shown in Fig. 1) measured with Photo Research PR650 spectrometers 20mA/cm2Current density under power efficiency it is as shown in table 1.
Embodiment Compound Power efficiency (lm/W) Color
5 4 6.4 Green glow
6 23 6.8 Green glow
7 36 7.0 Green glow
8 45 6.9 Green glow
Comparative example Alq3 5.4 Green glow
Under the same conditions, the organic electroluminescent prepared using the organic electroluminescent electron transport material of the present invention The life-span 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 life-span and optical purity.
Structural formula is as follows described in device：
Preferred embodiment of the invention described in detail above.It should be appreciated that the ordinary skill of this area is without wound The property made work just can make many modifications and variations according to the design of the present invention.Therefore, all technical staff 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 in the protection domain being defined in the patent claims.

Claims (10)

1. one kind contains the organic electroluminescent electron transport compound of [1,2,4]-triazole [1,5-a] pyridine, it is characterised in that It is the compound with following structural formula I：
Wherein, R1-R4Separately selected from hydrogen, deuterium, halogen, cyano group, straight chain or C1-C12 alkyl with side chain, straight chain or The substitution of C1-C8 alkoxyl, C6-C30 with side chain or unsubstituted aryl, C3-C30 substitution or unsubstituted miscellaneous Aryl, triaryl phosphinyl；
L be selected from singly-bound, C6-C30 substitution or unsubstituted aryl, C3-C30 substitution or it is unsubstituted containing one or The multiple heteroatomic heteroaryls of person；
Ar is selected from C6-C30 substitution or unsubstituted aryl, C3-C30 substitution or unsubstituted containing one or many Individual heteroatomic heteroaryl, triaryl phosphinyl；
Py is pyridine radicals；
Ar1Selected from hydrogen, deuterium, C6-C30 substitution or unsubstituted aryl.
2. the organic electroluminescent electric transmission according to claim 1 containing [1,2,4]-triazole [1,5-a] pyridine Compound, it is characterised in that R1-R4Separately it is selected from hydrogen, deuterium, fluorine, phenyl, naphthyl, phenanthryl, pyrenyl, xenyl, phenylnaphthalene Base, naphthylphenyl, pyridine radicals, diphenyl phenyl.
3. the organic electroluminescent electric transmission according to claim 1 containing [1,2,4]-triazole [1,5-a] pyridine Compound, it is characterised in that L is selected from singly-bound, phenyl, naphthyl.
4. the organic electroluminescent electric transmission according to claim 1 containing [1,2,4]-triazole [1,5-a] pyridine Compound, it is characterised in that Ar1Selected from hydrogen, phenyl, naphthyl.
5. the organic electroluminescent electric transmission according to claim 1 containing [1,2,4]-triazole [1,5-a] pyridine Compound, it is characterised in that Ar be selected from benzene, naphthyl, anthryl, phenanthryl, pyrenyl, perylenes base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (9, 9- bis- replaces or unsubstituted aryl) fluorenyl, 9,9- Spirofluorene-based, dibenzothiophenes base, dibenzofuran group, xenyl, benzene Base naphthyl, naphthylphenyl, diphenyl base phenyl, pyridine radicals, quinolyl, pyrimidine radicals, triazine radical, thiazolyl, oxazolyl, triazole Base, quinoxalinyl, isoquinolyl, phenylpyridyl, pyridinylphenyl, bipyridyl, or more these groups further be C1- C10 alkyl or alkoxy substitution.
6. the organic electroluminescent electric transmission according to claim 1 containing [1,2,4]-triazole [1,5-a] pyridine Compound, it is characterised in that it is following structural 1-54 compound：
7. a kind of organic electroluminescence device, it includes anode, negative electrode and organic layer, and organic layer injects comprising luminescent layer, hole At least one layer in layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, it is characterised in that in organic layer At least one layer includes the organic electroluminescent electronics as claimed in claim 1 for containing [1,2,4]-triazole [1,5-a] pyridine Transport compound.
8. organic electroluminescence device according to claim 7, it is characterised in that as described in structural formula I containing [1,2, Layer where the organic electroluminescent electron transport compound of 4]-triazole [1,5-a] pyridine is electron transfer layer or electron injection Layer.
9. organic electroluminescence device according to claim 7, it is characterised in that as described in structural formula I containing [1,2, A kind of compound therein is used alone in the organic electroluminescent electron transport compound of 4]-triazole [1,5-a] pyridine, or simultaneously Use the two or more compounds in structural formula I.
10. organic electroluminescence device according to claim 7, it includes anode, hole transmission layer, luminescent layer, electronics Transport layer, electron injecting layer and negative electrode, it is characterised in that contain at least one structural formula I in electron transfer layer or electron injecting layer Compound.
CN201710413701.1A 2017-06-05 2017-06-05 Compound and its organic electroluminescence device containing [1,2,4] triazole [1,5 a] pyridine Pending CN107033143A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108047087A (en) * 2018-01-18 2018-05-18 河南省科学院化学研究所有限公司 3 '-(4- bromonaphthalene -1- bases) [1,1 '-xenyl] -4- nitriles and its synthetic method
CN108084180A (en) * 2017-12-26 2018-05-29 南京高光半导体材料有限公司 A kind of novel electroluminescent compound and the organic electroluminescence device using the organic electroluminescent compounds
CN110590770A (en) * 2019-08-22 2019-12-20 武汉尚赛光电科技有限公司 Triazolopyridine-based organic electroluminescent material and organic electroluminescent device
KR20200126198A (en) * 2019-04-29 2020-11-06 주식회사 엘지화학 Novel hetero-cyclic compound and organic light emitting device comprising the same

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106632325A (en) * 2017-01-25 2017-05-10 上海道亦化工科技有限公司 Azacycle-containing compound and organic electroluminescence device thereof
CN106749234A (en) * 2016-11-24 2017-05-31 上海道亦化工科技有限公司 Organic electroluminescent electron transport compound and its luminescent device based on anthracene

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106749234A (en) * 2016-11-24 2017-05-31 上海道亦化工科技有限公司 Organic electroluminescent electron transport compound and its luminescent device based on anthracene
CN106632325A (en) * 2017-01-25 2017-05-10 上海道亦化工科技有限公司 Azacycle-containing compound and organic electroluminescence device thereof

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108084180A (en) * 2017-12-26 2018-05-29 南京高光半导体材料有限公司 A kind of novel electroluminescent compound and the organic electroluminescence device using the organic electroluminescent compounds
CN108047087A (en) * 2018-01-18 2018-05-18 河南省科学院化学研究所有限公司 3 '-(4- bromonaphthalene -1- bases) [1,1 '-xenyl] -4- nitriles and its synthetic method
KR20200126198A (en) * 2019-04-29 2020-11-06 주식회사 엘지화학 Novel hetero-cyclic compound and organic light emitting device comprising the same
KR102521449B1 (en) 2019-04-29 2023-04-12 주식회사 엘지화학 Novel hetero-cyclic compound and organic light emitting device comprising the same
CN110590770A (en) * 2019-08-22 2019-12-20 武汉尚赛光电科技有限公司 Triazolopyridine-based organic electroluminescent material and organic electroluminescent device

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Application publication date: 20170811