CN107253954A - Compound and its organic electroluminescence device containing pyridine groups - Google Patents

Compound and its organic electroluminescence device containing pyridine groups Download PDF

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CN107253954A
CN107253954A CN201710414649.1A CN201710414649A CN107253954A CN 107253954 A CN107253954 A CN 107253954A CN 201710414649 A CN201710414649 A CN 201710414649A CN 107253954 A CN107253954 A CN 107253954A
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organic
compound
substitution
electron transport
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黄锦海
苏建华
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Shanghai Taoe Chemical Technology Co Ltd
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Shanghai Taoe Chemical Technology Co Ltd
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  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention provides a kind of organic electroluminescent electron transport compound containing pyridine groups, 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 electroluminescence device containing pyridine groups
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of compound containing pyridine groups and its has Organic electroluminescence devices, 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 electron transport compound containing pyridine groups, it is with such as Lower structural formula I compound：
Wherein, L is selected from singly-bound, C6-C30 substitution or unsubstituted aryl, C3-C30 substitution or unsubstituted Contain one or more heteroatomic heteroaryl；
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；
Py is pyridine radicals；
Ar ' is selected from hydrogen, C6-C30 substitution or unsubstituted aryl；
Z1-Z8One of them is N, and remaining is CH；
A is selected from O, S, SO, SO2、Se。
Preferably, L is selected from singly-bound, phenyl, naphthyl, pyridine radicals, quinolyl, xenyl, fluorenyl, dibenzothiophenes base, two Benzofuranyl, carbazyl, benzimidazolyl, benzothiazolyl, pyrimidine radicals, benzothiazolyl, oxazolyl, thiazolyl.
Preferably, Ar ' is selected from hydrogen, phenyl, naphthyl, phenanthryl, fluorenyl.
Preferably, A is O or S.
Preferably, Ar is selected from
Wherein, L1、L2、L3Separately it is selected from singly-bound, C6-C30 substitution or unsubstituted aryl；Z9、Z10、Z11 In at least one be N, remaining is CH；Ar1-Ar3Separately it is selected from hydrogen, deuterium, C1-C8 alkyl, C1-C8 alkoxyl, C6- C30 substitution or unsubstituted aryl, C3-C30 substitution or unsubstituted heteroatomic miscellaneous containing one or more Aryl；X is selected from O, S, Se, NR, and wherein R is selected from C1-C8 alkyl, C1-C8 alkoxyl, C6-C30 substitution or unsubstituted virtue Base, C3-C30 substitution unsubstituted contain one or more heteroatomic heteroaryl.
Preferably, A is O or S；L、L1、L2And L3Separately it is selected from singly-bound, phenyl, naphthyl, pyridine radicals, xenyl；X Selected from O, S, NR；Ar1-Ar3Methyl, ethyl, propyl group, butyl, amyl group, hexyl, octyl group, phenyl, first are separately selected from R Phenyl, naphthyl, xenyl, diphenyl phenyl, phenyl napthyl, naphthylphenyl, phenanthryl, fluoranthene base, anthryl, pyrenyl, fluorenyl, hexichol And furyl, dibenzothiophenes base, pyridine radicals, pyrimidine radicals, quinolyl, isoquinolyl, triazine radical, pyrrole radicals, furyl, thiazole Base, the above aryl and heteroaryl further can replace for C1-C10 alkyl or alkoxy.
It is further preferred that the organic electroluminescent electron transport compound of the invention containing pyridine groups is having structure Formula 1-92 compound：
The organic electroluminescent electron transport compound containing pyridine groups of the present invention can be applied in organic electroluminescence hair Optical 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 the electricity of the organic electroluminescent containing pyridine groups that at least one layer contains as described in structural formula I in the organic layer Sub- transport compound：
Wherein Z1-Z8, A, Ar, Py, Ar ' 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 where the organic electroluminescent electron transport compound containing pyridine groups as described in structural formula I Layer be electron transfer layer or electron injecting layer.
Preferably, the organic electroluminescent electron transport compound containing pyridine groups is structure wherein described in structural formula I Formula 1-92 compound.
The organic electroluminescent electron transport compound containing pyridine groups as described in structural formula I is used for luminescent device system When standby, it can be used alone, can also be used in mixed way with other compounds；The electricity containing pyridine groups as described in structural formula I Electro luminescent compounds can be used alone a kind of compound therein, can also use simultaneously two or more in structural formula I Compound.
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 1-92 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 electroluminescent electric transmission containing pyridine groups of the present invention as described in structural formula I Compound has preferable heat endurance, high-luminous-efficiency, high luminance purity.Made using the compound for containing pyridine groups Organic electroluminescence device has the advantages that electroluminescent efficiency is good and excitation is excellent and 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 1
Intermediate 1-1 synthesis
In flask, add 3- bromo- 5- chlorobenzaldehydes (10g, 46mmol), connection boric acid pinacol ester (14g, 55mmol), Potassium acetate (6.8g, 69mmol), [double (diphenylphosphino) ferrocene of 1,1'-] palladium chloride (0.5g) and dioxane (100mL), is heated to reflux 12 hours under nitrogen protection, cooling, adds water, is extracted with dichloromethane, dries, concentration, crude product 7.7g, yield 63% are obtained through column chromatography purifying.
Intermediate 1-2 synthesis
In flask, add intermediate 1-1 (8.0g, 30mmol), the chloro- benzofurans of 3- [3,2-c] pyridine (6g, 30mmol), potassium carbonate (8.3g, 60mmol), tetra-triphenylphosphine palladium (0.5g), tetrahydrofuran (100mL) and water (30mL), in nitrogen It is heated to reflux under gas shielded 12 hours, adds water, extracted with dichloromethane, dried, concentration, crude product is obtained through column chromatography purifying 6.9g, yield 75%.
Intermediate 1-3 synthesis
In flask, intermediate 1-2 (7g, 23mmol), Amidinobenzene hydrochloride (8.1g, 46mmol), sodium methoxide are added (2.5g, 46mmol), ethanol (50mL), is heated to reflux 12 hours under nitrogen protection, cooling, removes ethanol, adds water, use dichloro Methane extract, dry, concentration, add acetone (80mL), then add 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (5.2g, 23mmol), stir 2 hours, filtering, filter cake is beaten with ethanol, filter, be dried to obtain 9.5g, yield 83%.
The synthesis of compound 1
In flask, intermediate 1-3 (2.3g, 4.5mmol), 3- pyridine boronic acids (1.1g, 9mmol), potassium carbonate are added (1.2g, 9mmol), toluene (20mL), ethanol (10mL), water (10mL), palladium (0.2g), X-phos (0.2g), in nitrogen It is heated to reflux under protection 24 hours, cools down, extracted with chloroform, dried, concentration, crude product obtains 1.4g through column chromatography purifying, produces Rate 55%.
Embodiment 2
The synthesis of compound 13
Synthetic method is with the synthesis of compound 1, except replacing 3- pyridines with 2- phenyl -5- pyridine boronic acid pinacol esters Outside boric acid, yield 47%.
Embodiment 3
The synthesis of compound 20
Synthetic method is with the synthesis of compound 1, except replacing 3- pyrroles with 4- (3- pyridine radicals) phenyl boric acid pinacol ester Outside pyridine boric acid, yield 63%.
Embodiment 4
The synthesis of compound 24
Intermediate 24-1 synthesis
In three-necked flask, 3,5- dichloros phenyl boric acid (15g, 79mmol), the chloro- benzofurans of 3- [3,2-c] pyridine are added (16g, 79mmol), potassium carbonate (22g, 158mmol), tetra-triphenylphosphine palladium (0.5g), tetrahydrofuran (200mL), water (80mL), It is heated to reflux under nitrogen protection 12 hours, cools down, add water, extracted with dichloromethane, dries, concentration, crude product is through column chromatography Purifying obtains 19g, yield 77%.
Intermediate 24-2 synthesis
In flask, intermediate 24-1 (10g, 32mmol), 3- pyridine boronic acids (4.6g, 38mmol), potassium carbonate are added (8.9g, 64mmol), palladium (0.5g), X-phos (0.6g), toluene (80mL), ethanol (40mL), water (40mL), in nitrogen It is heated to reflux under protection 12 hours, cools down, add water, extracted with dichloromethane, dried, concentration, crude product is purified through column chromatography To 4.7g, yield 41%.
The synthesis of compound 24
Synthetic method is with the synthesis of compound 1, with intermediate 24-2 and 2,4- diphenyl -6- (4- boric acid pinacols Ester phenyl) -1,3,5-triazines, yield 65%.
Embodiment 5
The synthesis of compound 43
Synthetic method is with the synthesis of compound 1, raw materials used is intermediate 24-2 and B- [4- (1- phenyl -1H- benzene And imidazoles -2- bases) phenyl]-boric acid, yield 72%.
Embodiment 6
The synthesis of compound 47
Intermediate 47-1 synthesis
Synthetic method is with intermediate 1-2 synthetic method, raw materials used is the chloro- benzothiophene of intermediate 1-1 and 3- [3,2-c] pyridine, yield 74%.
Intermediate 47-2 synthesis
Synthetic method is with as intermediate 1-3, raw materials used is intermediate 47-1 and Amidinobenzene hydrochloride, yield 69%.
The synthesis of compound 47
Synthetic method is with the synthesis of compound 1, raw materials used is intermediate 47-2 and 3- pyridine boronic acid, yield 46%.
Embodiment 7
The synthesis of compound 66
Synthetic method with intermediate 47-2 with the synthetic method of compound 20, being replaced outside intermediate 1-3, yield 56%.
Embodiment 8
The synthesis of compound 70
Intermediate 70-1 synthesis
Synthetic method is with intermediate 24-1, except replacing the chloro- benzos of 3- with the chloro- benzothiophenes of 3- [3,2-c] pyridine Outside furans [3,2-c] pyridine, yield 69%.
Intermediate 70-2 synthesis
Synthetic method is with intermediate 24-2, in addition to replacing intermediate 24-2 with intermediate 70-1, yield 52%.
The synthesis of compound 70
Synthetic method is with as compound 24, in addition to replacing intermediate 24-2 with intermediate 70-2, yield 51%.
Embodiment 9-16
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 9-16.
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
9 1 6.8 Green glow
10 13 7.1 Green glow
11 20 6.6 Green glow
12 24 6.7 Green glow
13 43 5.4 Green glow
14 47 7.0 Green glow
15 66 6.8 Green glow
16 70 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. a kind of organic electroluminescent electron transport compound containing pyridine groups, it is characterised in that it is with following structure The compound of Formulas I：
Wherein, L be selected from singly-bound, C6-C30 substitution or unsubstituted aryl, C3-C30 substitution or it is unsubstituted containing One or more heteroatomic heteroaryl；
Ar is selected from C6-C30 substitution or unsubstituted aryl, C3-C30 substitution or unsubstituted containing one or many Individual heteroatomic heteroaryl；
Py is pyridine radicals；
Ar ' is selected from hydrogen, C6-C30 substitution or unsubstituted aryl；
Z1-Z8One of them is N, and remaining is CH；
A is selected from O, S, SO, SO2、Se。
2. the organic electroluminescent electron transport compound according to claim 1 containing pyridine groups, it is characterised in that L Selected from singly-bound, phenyl, naphthyl, pyridine radicals, quinolyl, xenyl, fluorenyl, dibenzothiophenes base, dibenzofuran group, carbazole Base, benzimidazolyl, benzothiazolyl, pyrimidine radicals, benzothiazolyl, oxazolyl, thiazolyl.
3. the organic electroluminescent electron transport compound according to claim 1 containing pyridine groups, it is characterised in that Ar ' is selected from hydrogen, phenyl, naphthyl, phenanthryl, fluorenyl.
4. the organic electroluminescent electron transport compound according to claim 1 containing pyridine groups, it is characterised in that A For O or S.
5. the organic electroluminescent electron transport compound according to claim 1 containing pyridine groups, it is characterised in that Ar is selected from
Wherein, L1、L2、L3Separately it is selected from singly-bound, C6-C30 substitution or unsubstituted aryl；Z9、Z10、Z11In extremely Rare one is N, and remaining is CH；Ar1-Ar3Separately selected from hydrogen, deuterium, C1-C8 alkyl, C1-C8 alkoxyl, C6-C30 Substitution or unsubstituted aryl, C3-C30 substitution unsubstituted contain one or more heteroatomic heteroaryl；X Selected from O, S, Se, NR, wherein R is selected from C1-C8 alkyl, C1-C8 alkoxyl, C6-C30 substitution or unsubstituted aryl, C3- C30 substitution unsubstituted contains one or more heteroatomic heteroaryl.
6. the organic electroluminescent electron transport compound according to claim 5 containing pyridine groups, it is characterised in that A For O or S；L、L1、L2And L3Separately it is selected from singly-bound, phenyl, naphthyl, pyridine radicals, xenyl；X is selected from O, S, NR；Ar1- Ar3Methyl, ethyl, propyl group, butyl, amyl group, hexyl, octyl group, phenyl, tolyl, naphthyl, biphenyl are separately selected from R Base, diphenyl phenyl, phenyl napthyl, naphthylphenyl, phenanthryl, fluoranthene base, anthryl, pyrenyl, fluorenyl, dibenzofuran group, hexichol Bithiophene base, pyridine radicals, pyrimidine radicals, quinolyl, isoquinolyl, triazine radical, pyrrole radicals, furyl, thiazolyl, or more these Aryl and heteroaryl further replace for C1-C10 alkyl or alkoxy.
7. the organic electroluminescent electron transport compound according to claim 1 containing pyridine groups, it is characterised in that It is following structural 1-92 compound：
8. 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 electron transport compound as claimed in claim 1 containing pyridine groups.
9. organic electroluminescence device according to claim 8, it is characterised in that contain pyridine radicals as described in structural formula I Layer where the organic electroluminescent electron transport compound of group is electron transfer layer or electron injecting layer.
10. organic electroluminescence device according to claim 8, 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.
CN201710414649.1A 2017-06-05 2017-06-05 Compound and its organic electroluminescence device containing pyridine groups Pending CN107253954A (en)

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CN110283178A (en) * 2019-07-15 2019-09-27 陕西莱特光电材料股份有限公司 A kind of heterocyclic compound and its synthetic method and the organic electroluminescent device comprising the compound
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CN112679511A (en) * 2020-12-14 2021-04-20 阜阳欣奕华材料科技有限公司 Organic electroluminescent material and application thereof
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Application publication date: 20171017