CN105061439B - A kind of organic electroluminescent compounds and its organic electroluminescence device - Google Patents

A kind of organic electroluminescent compounds and its organic electroluminescence device Download PDF

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CN105061439B
CN105061439B CN201510481891.1A CN201510481891A CN105061439B CN 105061439 B CN105061439 B CN 105061439B CN 201510481891 A CN201510481891 A CN 201510481891A CN 105061439 B CN105061439 B CN 105061439B
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organic electroluminescence
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CN105061439A (en
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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
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom

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Abstract

The invention provides a kind of such as structural formula I novel electroluminescent 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 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

A kind of organic electroluminescent compounds and its organic electroluminescence device
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of novel electroluminescent compound 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, 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.It is voltage-operated in application additionally, due to OLED When, 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 electroluminescent organic material of stability and high efficiency.
Organic electrophosphorescenpolymer phenomenon, breaches theoretical limitation of the organic electroluminescent quantum efficiency less than 25%, and lifting is arrived 100% (Baldo M.A., Forrest S.R.Et al, Nature, 1998,395,151-154), its application also greatly carry The high efficiency of organic electroluminescence device.Usually, electroluminescent phosphorescence needs to use host-guest system technology, and conventional is used as phosphorus The CBP (4,4'-bis (9-carbazolyl)-biphenyl) of light material of main part has efficient and high triplet energy level, when its work For material of main part when, triplet energy state effectively can be transferred to object phosphorescent light-emitting materials from light emitting host material.But by Easily transmitted and the characteristic of the difficult flowing of electronics in CBP hole so that the charge unbalance of luminescent layer, as a result reduce the effect of device Rate.
The content of the invention
Present invention firstly provides a kind of new organic electroluminescent compounds, and it is the chemical combination with following structural formula I Thing：
Wherein, L1And L2Separately taken selected from singly-bound, C6-C30 substitution or unsubstituted aryl, C3-C30 Generation or the unsubstituted heteroatomic aryl containing one or more；
Z1-Z8In to have one be N, remaining is CH；
A and B is separately selected from O, S, SO, SO2、Se、CR1R2；
R1And R2Separately selected from C1-C8 alkoxyl, C6-C30 substitution or unsubstituted aryl, C3-C30 Substitution unsubstituted contains one or more heteroatomic aryl.
Preferably, L1And L2Separately selected from singly-bound, phenyl, naphthyl, pyridine radicals, quinolyl, xenyl, fluorenyl, two Benzothienyl, dibenzofuran group, carbazyl, benzimidazolyl, benzothiazolyl, pyrimidine radicals, benzothiazolyl, oxazole Base, thiazolyl；
A and B is separately selected from O, S.
It is highly preferred that L1And L2Separately selected from singly-bound, phenyl, naphthyl, xenyl.
It is further preferred that the novel electroluminescent compound of the present invention is following structural 1-36 compound：
The new compound of the present invention can be applied in organic electroluminescence device, organic solar batteries, organic film Transistor 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 one layer or one in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer More than layer, wherein at least one layer new compound contained as described in structural formula I in the organic layer：
Wherein L1-L2、Z1-Z8, A and B it is defined as described above.
Wherein organic layer is luminescent layer；
Or organic layer is luminescent layer and electron transfer layer；
Or organic layer is luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole transmission layer and luminescent layer；
Or organic layer is hole injection layer, hole transmission layer and luminescent layer；
Or organic layer is hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole injection layer, hole transmission layer, barrier layer, luminescent layer, electron transfer layer and electron injection Layer；
Or organic layer is hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and hole blocking layer；
Or organic layer is hole transmission layer, luminescent layer, electron injecting layer and hole blocking layer.
Preferably, wherein the layer where new compound as described in structural formula I is luminescent layer；
Preferably, the new compound wherein described in structural formula I is structural formula 1-36 compound；
When compound as described in structural formula I is used for luminescent device preparation, it can be used alone, can also be with other chemical combination Thing is used in mixed way；Compound as described in structural formula I can be used alone a kind of compound therein, can also be simultaneously using knot Two or more compound in structure Formulas I.
The organic electroluminescence device of the present invention, further preferred mode are that the organic electroluminescence device includes sun Contain in pole, hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, wherein luminescent layer One or more kinds of structural formula I compound；It is further preferred that contain one or more kinds of structures in luminescent layer Formula 1-36 compound.
The luminescent layer of organic electroluminescence device contains phosphorescence light emitting guest material and the compound conduct with structural formula I As material of main part, its concentration is the 20-99.9% of whole luminous layer weight, excellent for material of main part, wherein structural formula I compound Select 80-99%, more preferably 90-99%.
The gross thickness of the organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
When having structural formula I compound using the present invention, can arrange in pairs or groups makes the organic electroluminescence device of the present invention With other materials, such as in hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and hole blocking layer It is medium, 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.Except the present invention have Compounds of structural formula I as phosphorescent light body material in addition to, can also arrange in pairs or groups other phosphorescence Material of main part, phosphorescence light emitting guest material can be included selected from least one of ruthenium, copper, rhodium, silver, iridium, platinum, gold and osmium metal Metal-organic complex.
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.Following compound can be selected, but It is not limited to this：Oxa- oxazole, thiazole compound, triazole compound, three nitrogen piperazine class compounds, triazine class chemical combination Thing, quinoline class compound, phenodiazine anthracene compound, siliceous heterocycle compound, quinolines, ferrosin class compound, Metallo-chelate (such as Alq3), fluorine substituted benzene compound, 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, it is mainly selected from the compound of alkali metal or alkali metal, or compound or alkali selected from alkaline-earth metal either alkaline-earth metal Metal complex, can select following compound, but not limited to this：Alkali metal, alkaline-earth metal, rare earth metal, alkali metal Oxide either halide, the oxide of alkaline-earth metal or halide, the oxide of rare earth metal or halide, alkali metal Or the organic complex of alkaline-earth metal；Preferably lithium, lithium fluoride, lithia, lithium nitride, 8-hydroxyquinoline lithium, caesium, carbonic acid Caesium, 8-hydroxyquinoline caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, magnesia, these compounds can individually make With can also mixture use, can also be used cooperatively with other electroluminescent organic materials.
Each layer of organic layer in the organic electroluminescence device of the present invention, 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 new compound of the present invention as described in structural formula I, have preferable heat endurance, height luminous Efficiency, high luminance purity.Using the new compound make organic electroluminescence device have electroluminescent efficiency well 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 injection layer, and 140 are represented as sky Cave transport layer, 150 are represented as luminescent layer, and 160 are represented as electron transfer layer, and 170 are represented as electron injecting layer, and 180 are represented as the moon Pole.
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 three-necked flask, add 3- bromines carbazole (24.5g, 0.1mol), 4- dibenzofurans boric acid (21.2g, 0.1mol), potassium carbonate (27.2g, 0.2mol), 300ml tetrahydrofurans, 100ml water and tetra-triphenylphosphine palladium (0.5g), in nitrogen It is heated to reflux under protection 12 hours, cools down, be extracted with ethyl acetate, dried, concentration, crude product is obtained with recrystallizing methanol 30.6g products, yield 92%.
Intermediate 1-2 synthesis
In three-necked flask, intermediate 1-1 (25g, 0.075mol), a bromo-iodobenzene (28.1g, 0.1mol), hydrogen-oxygen are added Change potassium (5.6g, 0.1mol), cuprous iodide (1.9g), Phen (2.5g) and 300ml mesitylene, add under nitrogen protection Heat backflow 24 hours, cooling, removal of solvent under reduced pressure, adds water and dichloromethane, is layered, organic phase anhydrous sodium sulfate drying, Concentration, crude product are purified to obtain 29.2g products, yield 80% with column chromatography.
Intermediate 1-3 synthesis
In three-necked flask, the tetrahydrofuran that intermediate 1-2 (15g, 0.031mol), 180ml are dried is added, be cooled to- 78 degree, under nitrogen protection, the hexane solution (15ml, 0.037mmol) of 2.5M n-BuLi is slowly added dropwise, in this temperature Lower reaction 2 hours, is then slowly added into triisopropyl borate ester (8.7g, 0.046mol), drips off, and it is small to be slowly increased to room temperature reaction 12 When, 1N dilute hydrochloric acid solution is slowly added dropwise, is extracted with ethyl acetate, then with anhydrous sodium sulfate drying, concentration, with ether and just oneself Alkane is recrystallized to give 9.1g products, yield 65%.
The synthesis of compound 1
In three-necked flask, intermediate 1-3 (2.5g, 5.5mmol), the chloro- benzofurans of 3- [3,2-c] pyridine are added (1.2g, 5.9mmol), potassium carbonate (1.5g, 11mmol), 30ml tetrahydrofurans, 10ml water and tetra-triphenylphosphine palladium (50mg), It is heated to reflux 12 hours under nitrogen protection, cools down, extracted with dichloromethane, dried, concentration, crude product column chromatography for separation obtains 2.5g products, yield 78%.
Embodiment 2
The synthesis of compound 9
In three-necked flask, intermediate 1-3 (2.5g, 5.5mmol), the chloro- benzothiophenes of 3- [3,2-c] pyridine are added (1.3g, 6.0mmol), potassium carbonate (1.5g, 11mmol), 30ml tetrahydrofurans, 10ml water and tetra-triphenylphosphine palladium (50mg), It is heated to reflux 12 hours under nitrogen protection, cools down, extracted with dichloromethane, dried, concentration, crude product column chromatography for separation obtains 2.4g products, yield 73%.
Embodiment 3
The synthesis of compound 19
Intermediate 19-1 synthesis
In three-necked flask, add 3- bromines carbazole (24.5g, 0.1mol), 4- dibenzofurans boric acid (22.8g, 0.1mol), potassium carbonate (27.2g, 0.2mol), 300ml tetrahydrofurans, 100ml water and tetra-triphenylphosphine palladium (0.5g), in nitrogen It is heated to reflux under protection 12 hours, cools down, be extracted with ethyl acetate, dried, concentration, crude product obtains 31g with recrystallizing methanol Product, yield 89%.
Intermediate 19-2 synthesis
In three-necked flask, intermediate 19-1 (25g, 0.072mol), a bromo-iodobenzene (28.1g, 0.1mol), hydrogen-oxygen are added Change potassium (5.6g, 0.1mol), cuprous iodide (1.9g), Phen (2.5g) and 300ml mesitylene, add under nitrogen protection Heat backflow 24 hours, cooling, removal of solvent under reduced pressure, adds water and dichloromethane, is layered, organic phase anhydrous sodium sulfate drying, Concentration, crude product are purified to obtain 26.1g products, yield 72% with column chromatography.
Intermediate 19-3 synthesis
In three-necked flask, the tetrahydrofuran that intermediate 19-2 (15g, 0.030mol), 180ml are dried is added, be cooled to- 78 degree, under nitrogen protection, the hexane solution (15ml, 0.037mmol) of 2.5M n-BuLi is slowly added dropwise, in this temperature Lower reaction 2 hours, is then slowly added into triisopropyl borate ester (8.7g, 0.046mol), drips off, and it is small to be slowly increased to room temperature reaction 12 When, 1N dilute hydrochloric acid solution is slowly added dropwise, is extracted with ethyl acetate, then with anhydrous sodium sulfate drying, concentration, with ether and just oneself Alkane is recrystallized to give 10g products, yield 71%.
The synthesis of compound 19
In three-necked flask, intermediate 19-3 (2.5g, 5.3mmol), the chloro- benzofurans of 3- [3,2-c] pyridine are added (1.2g, 5.9mmol), potassium carbonate (1.5g, 11mmol), 30ml tetrahydrofurans, 10ml water and tetra-triphenylphosphine palladium (50mg), It is heated to reflux 12 hours under nitrogen protection, cools down, extracted with dichloromethane, dried, concentration, crude product column chromatography for separation obtains 2.6g products, yield 82%.
Embodiment 4
The synthesis of compound 27
In three-necked flask, intermediate 19-3 (2.5g, 5.3mmol), the chloro- benzothiophenes of 3- [3,2-c] pyridine are added (1.3g, 6.0mmol), potassium carbonate (1.5g, 11mmol), 30ml tetrahydrofurans, 10ml water and tetra-triphenylphosphine palladium (50mg), It is heated to reflux 12 hours under nitrogen protection, cools down, extracted with dichloromethane, dried, concentration, crude product column chromatography for separation obtains 2.7g products, yield 85%.
Embodiment 5
The preparation of organic electroluminescence device
OLED is prepared using the compound 1 of embodiment 1.
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, it is hole injection layer 130 that the thick HAT-CN of 5nm are deposited on ITO.
Then, TAPC is deposited, forms the thick hole transmission layers 140 of 65nm.
Then, steamed on hole transmission layer and cross 10nm thickness luminescent layer 150, wherein, compound 1 is main body luminescent material, and Guest materials is adulterated using 7%Ir (ppy) 2acac as phosphorescence.
Then, the thick TmPyPB of 50nm are deposited on luminescent layer as electron transfer layer 160.
Finally, evaporation 1nm LiF are electron injecting layer 170 and 100nm Al as device cathodes 180.
Prepared device (structural representation is shown in Fig. 1) is measured in 100mA/ with Photo Research PR650 spectrometers cm2Current density under driving voltage be 5.6V, be green spectral.
Embodiment 6
The method of device is prepared as embodiment 5, in addition to replacing compound 1 with compound 9.
Prepared device is measured in 100mA/cm with Photo Research PR650 spectrometers2Current density under Driving voltage is 5.7V, is green spectral.
Embodiment 7
The method of device is prepared as embodiment 5, in addition to replacing compound 1 with compound 19.
Prepared device is measured in 100mA/cm with Photo Research PR650 spectrometers2Current density under Driving voltage is 5.8V, is green spectral.
Embodiment 8
The method of device is prepared as embodiment 5, in addition to replacing compound 1 with compound 27.
Prepared device is measured in 100mA/cm with Photo Research PR650 spectrometers2Current density under Driving voltage is 5.5V, is green spectral.
Comparative example
The method of device is prepared as embodiment 5, in addition to replacing compound 1 with compound CBP.
Prepared device is measured in 100mA/cm with Photo Research PR650 spectrometers2Current density under Driving voltage is 6.7V, is green spectral.
Verified, new organic electroluminescent compounds of the invention have more excellent photo electric than conventional material Matter, the organic electroluminescence device prepared by the present invention have 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 the ordinary skill of this area is without wound The property made work can makes many modifications and variations according to the design of the present invention.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 in the protection domain being defined in the patent claims.

Claims (8)

1. a kind of organic electroluminescent compounds, it is characterised in that it is the compound with following structural formula I：
Wherein, L1For singly-bound, L2For phenyl；
Z1-Z4In to have one be N, remaining is CH, Z5-Z8For CH；
A and B is separately selected from O, S, Se.
2. organic electroluminescent compounds according to claim 1, it is characterised in that wherein, A and B are separately selected from O、S。
3. organic electroluminescent compounds as claimed in claim 1, it is characterised in that its be following structural 1-4,9-12, The compound of 17-22,27-30,35,36：
4. a kind of organic electroluminescence device, it includes anode, negative electrode and organic layer, and organic layer includes luminescent layer, hole is injected It is one or more layers in layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, it is characterised in that hair Photosphere includes organic electroluminescent compounds as claimed in claim 1.
5. organic electroluminescence device according to claim 4, it is characterised in that the organic electroluminescence as described in structural formula I Compound is used alone, or is used in mixed way with other compounds.
6. organic electroluminescence device according to claim 4, it is characterised in that the organic electroluminescence as described in structural formula I A kind of compound therein is used alone in compound, or uses two or more the compound in structural formula I simultaneously.
7. organic electroluminescence device according to claim 4, it includes anode, hole injection layer, hole transmission layer, hair Photosphere, electron transfer layer, electron injecting layer and negative electrode, it is characterised in that contain one or more kinds of structural formulas in luminescent layer I compound.
8. a kind of organic electroluminescence device, it includes anode, hole injection layer, hole transmission layer, luminescent layer, electric transmission Layer, electron injecting layer and negative electrode, it is characterised in that contain one or more kinds of knots according to claim 3 in luminescent layer Structure formula 1-4,9-12, the compound of 17-22,27-30,35,36.
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CN107641126A (en) * 2017-10-25 2018-01-30 上海道亦化工科技有限公司 A kind of organic electroluminescent compounds based on Imidazopyridazine and application thereof and organic electroluminescence device
CN107793436A (en) * 2017-10-25 2018-03-13 上海道亦化工科技有限公司 A kind of organic electroluminescent compounds based on double Imidazopyridazines and application thereof and organic electroluminescence device
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