CN108358932A - A kind of nitrogen heterocyclic and application thereof and organic electroluminescence device - Google Patents

A kind of nitrogen heterocyclic and application thereof and organic electroluminescence device Download PDF

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CN108358932A
CN108358932A CN201810122941.0A CN201810122941A CN108358932A CN 108358932 A CN108358932 A CN 108358932A CN 201810122941 A CN201810122941 A CN 201810122941A CN 108358932 A CN108358932 A CN 108358932A
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electroluminescence device
organic electroluminescence
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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 present invention provides a kind of nitrogen heterocyclics, have the following structure formula：The nitrogen heterocyclic has preferable thermal stability, high-luminous-efficiency, high luminance purity, can be applied to organic electroluminescence device, organic solar batteries, Organic Thin Film Transistors or organophotoreceptorswith field.The present invention also provides a kind of organic electroluminescence devices, the device includes anode, cathode and organic layer, organic layer includes at least one layer in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, the at least one layer heterocyclic compound containing such as structural formula I in organic layer, the organic electroluminescence device made of nitrogen heterocyclic have the advantages that electroluminescent efficiency is good and excitation purity is excellent and long lifespan.

Description

A kind of nitrogen heterocyclic and application thereof and organic electroluminescence device
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of nitrogen heterocyclic and application thereof also relates to And a kind of organic electroluminescence device.
Background technology
Organic electroluminescence device (OLEDs) is between two metal electrodes by spin coating or vacuum evaporation deposition one The device that layer organic material is prepared, a classical three layer organic electroluminescence device include hole transmission layer, luminescent layer And electron transfer layer.The electronics generated by cathode is followed to be incorporated in through electron transfer layer through hole transmission layer in the hole generated by anode Luminescent layer forms exciton, then shines.Organic electroluminescence device can be adjusted as desired by the material for changing luminescent layer Section emits the light of various needs.
Organic electroluminescence device has self-luminous, wide viewing angle, low energy consumption, efficiency as a kind of novel display technology High, thin, rich in color, fast response time, Applicable temperature range be wide, low driving voltage, can make flexible with it is transparent Display panel and the particular advantages such as environmental-friendly can be applied on flat-panel monitor and a new generation's illumination, be can also be used as The backlight of LCD.
Since the invention at the bottom of the 1980s, organic electroluminescence device is industrially applied, such as As screens such as camera and mobile phones, but current OLED device, since efficiency is low, it is wider that the factors such as service life is short restrict it General application, especially 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 device when applying voltage-operated, Joule heat will produce so that Organic material is easy to happen crystallization, affects service life and the efficiency of device, therefore, it is also desirable to develop the organic electroluminescence of stability and high efficiency Luminescent material.
Organic electrophosphorescenpolymer phenomenon, breaches theoretical limitation of the organic electroluminescent quantum efficiency less than 25%, and promotion is arrived 100% (Baldo M.A., Forrest S.R.Et al, Nature, 1998,395,151-154), application also greatly carry The high efficiency of organic electroluminescence device.Usually, electroluminescent phosphorescence needs to use host-guest system technology, is commonly 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 Based on material when, triplet energy state effectively can be transferred to object phosphorescent light-emitting materials from light emitting host material.But by In the characteristic of the hole of CBP easily transmission and the flowing of electronics difficulty so that as a result the charge unbalance of luminescent layer reduces the effect of device Rate.
Invention content
It is the compound for having the following structure Formulas I the present invention provides a kind of nitrogen heterocyclic：
Ar1-Ar5In it is at least one selected from substitution either unsubstituted C6-C30 carbazyl substitution or it is unsubstituted The triaromatic amine base of C18-C30, remaining aryl independently selected from hydrogen, substitution or unsubstituted C6-C30.
Optionally, the aryl is selected from phenyl, cyano-phenyl, fluorine substituted-phenyl, xenyl, diphenyl substituted-phenyl, naphthalene Base, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (substitutions or unsubstituted of 9,9- bis- Aryl) fluorenyl, 9,9- be Spirofluorene-based, substitution either unsubstituted dibenzothiophene and substitution or unsubstituted dibenzo furan It mutters base.
Optionally, the nitrogen heterocyclic is the compound of following structural 1-118：
The nitrogen heterocyclic of the present invention can be applied to organic electroluminescence device, organic solar batteries, organic thin Film transistor or organophotoreceptorswith field.
The present invention also provides a kind of organic electroluminescence device, which includes anode, cathode and organic layer, organic layer Including one layer or one in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer Layer or more, wherein at least one layer nitrogen heterocyclic contained as described in structural formula I in the organic layer.
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.
The compound that nitrogen heterocyclic described in wherein structural formula I is structural formula 1-118；Nitrogen as described in structural formula I Heterocyclic compound is used alone, or is used in mixed way with other compounds；A kind of azacyclo- selected from structural formula 1-118 is used alone Compound, or the two or more nitrogen heterocyclics selected from structural formula 1-118 are used simultaneously.
It is further preferred that the present invention organic electroluminescence device include anode, hole injection layer, hole transmission layer, Luminescent layer, electron transfer layer, electron injecting layer and cathode contain one or more kinds of structural formula I's wherein in luminescent layer Compound；It is further preferred that the compound containing one or more kinds of structural formula 1-118 in luminescent layer.
The organic electroluminescence device of the present invention, can also also serve as electronics when Compounds of structural formula I is as electron transfer layer Implanted layer.
The overall thickness of the organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
When having the compound of structural formula I using the present invention, can arrange in pairs or groups makes 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 barrier layer Deng, and obtain blue and green light, yellow light, feux rouges or white light.
The hole transmission layer and hole injection layer of organic electroluminescence device of the present invention, material requested have good hole Transmission performance can effectively be transferred to hole on luminescent layer from anode.In addition to the compound with I of the present invention can be used Outside, it can also include other small molecules and macromolecular organic compound, including but not limited to carbazole compound, triaromatic amine Close object, benzidine compound, compound of fluorene class, phthalocyanine-like compound, six cyano, six miscellaneous triphen (hexanitrilehexaazatriphenylene), tetra- cyanogen dimethyl-parabenzoquinone (F4- of tetra- fluoro- 7,7' of 2,3,5,6-, 8,8'- TCNQ), polyvinyl carbazole, 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 be adjusted according to the needs The range of visible light.In addition to the present invention is with Compounds of structural formula I, following compound can also be contained, but not limited to this, Naphthalene compounds, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance class compound,Class compound, glimmering anthracene compound, anthracene class chemical combination Object, pentacene class compound, class compound, two aromatic ethylene class compounds, triphenylamine ethylene compounds, aminated compounds, Benzimidazoles compound, furfuran compound, organic metal chelate complex.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires good electronic transmission performance, energy In reaching effectively electronics from cathode transport to luminescent layer, there is prodigious 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 Object, quinoline class compound, phenodiazine anthracene compound, siliceous heterocycle compound, quinolines, ferrosin class compound, Metallo-chelate (such as Alq3), fluorine substituted benzene compound, benzimidazoles compound.
Electronics effectively can be injected into organic layer by the electron injecting layer of organic electroluminescence device of the present invention from cathode In, it is mainly selected from the alkali metal either compound of alkali metal or the compound selected from alkaline-earth metal or alkaline-earth metal or alkali Metal complex can select following compound, and 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 can be steamed by vacuum vapour deposition, molecular beam It is prepared by the modes such as plating method, the dip coating for being dissolved in solvent, spin-coating method, stick coating method or inkjet printing.Metal motor can be made It is prepared with vapour deposition method or sputtering method.
Device experimental shows nitrogen heterocyclic of the present invention as described in structural formula I, has preferable thermal stability, occurred frequently Light efficiency, high luminance purity.Have electroluminescent efficiency good using the organic electroluminescence device that the nitrogen heterocyclic makes The advantages of good and excitation purity is excellent and long lifespan.
Description of the drawings
Fig. 1 is a kind of organic electroluminescence device structural schematic diagram of the present invention,
Wherein, 110 it is represented as glass substrate, 120 are represented as anode, and 130 are represented as hole injection layer, 140 hole transports Layer, 150 are represented as barrier layer, and 160 are represented as luminescent layer, and 170 are represented as electron transfer layer, and 180 are represented as electron injecting layer, 190 are represented as cathode.
Specific implementation mode
In order to describe the present invention in more detail, spy lifts following example, and but not limited to this.
Embodiment 1
The synthetic route of compound 1
The synthetic method of intermediate 1-1
In flask, 2- bromoacetophenones (10g, 50mmol), 3- amino -6- chlorine pyridazines (6.5g, 50mmol), ethyl alcohol is added (80mL) is heated to reflux 6 hours, cooling, and filtering obtains product 7.7g, yield 67%.
The synthetic method of compound 1
In flask, addition intermediate 1-1 (2g, 8.8mmol), 4- (9- carbazyls) phenyl boric acid (2.5g, 8.8mmol), Tetra-triphenylphosphine palladium (0.1g), potassium carbonate (2.5g, 18mmol), tetrahydrofuran (20mL), water (10mL) add under nitrogen protection Heat reflux 10 hours, it is cooling, it is extracted with dichloromethane, dry, concentration purifies to obtain product 3.3g, yield 86% through column chromatography.
Embodiment 2
The synthetic route of compound 3
The synthetic method of intermediate 3-1
In flask, addition 2- bromoacetophenones (10g, 50mmol), the bromo- 6- chlorine pyridazines of 3- amino -4- (10.4g, 50mmol), ethyl alcohol (100mL) is being added, is being heated to reflux 5 hours, cooling, filtering obtains product 14g, yield 92%.
The synthetic method of intermediate 3-2
In flask, intermediate 3-1 (8g, 26mmol), 4- biphenylboronic acids (5.2g, 26mmol), potassium carbonate is added (7.2g, 52mmol), tetrahydrofuran (100mL), water (50mL), tetra-triphenylphosphine palladium (0.3g) heat back under nitrogen protection Stream 6 hours, cooling, filtering, filter cake ethyl alcohol and tetrahydrofuran recrystallization, obtain product 5.7g, yield 58%.
The synthetic method of compound 3
Other than replacing intermediate 1-1 with intermediate 3-2, synthetic method is consistent with compound 1, yield 82%.
Embodiment 3
The synthetic route of compound 5
The synthetic method of compound 5
Consistent with the synthetic method of compound 1, raw materials used is intermediate 3-1 and 4- (9- carbazyls) phenyl boric acid, yield It is 65%.
Embodiment 4
The synthetic route of compound 22
Consistent with the synthetic method of compound 1, raw materials used is bromo- 6- chlorine imidazo [1, the 2-b] pyridazines of 3- and 4- (9- clicks Oxazolyl) phenyl boric acid, yield 73%.
Embodiment 5
The synthetic route of compound 27
Consistent with the synthetic method of compound 1, raw materials used is intermediate 1-1 and 9- phenyl -3- carbazole boric acid, and yield is 84%.
Embodiment 6
The synthetic route of compound 30
Consistent with the synthetic method of compound 1, raw materials used is intermediate 3-1 and 9- phenyl -3- carbazole boric acid, and yield is 72%.
Embodiment 7
The synthetic route of compound 49
Consistent with the synthetic method of compound 1, raw materials used is bromo- 6- chlorine imidazo [1, the 2-b] pyridazines of 3- and 9- phenyl- 3- carbazole boric acid, yield 63%.
Embodiment 8
The synthetic route of compound 54
Consistent with the synthetic method of compound 1, raw materials used is intermediate 1-1 and 4- boric acid triphenylamine, yield 69%.
Embodiment 9
The synthetic route of compound 57
Consistent with the synthetic method of compound 1, raw materials used is intermediate 3-1 and 4- boric acid triphenylamine, yield 49%.
Embodiment 10
The synthetic route of compound 74
Consistent with the synthetic method of compound 1, raw materials used is bromo- 6- chlorine imidazo [1, the 2-b] pyridazines of 3- and 4- boric acid Triphenylamine, yield 49%.
Embodiment 11
The synthetic route of compound 92
The synthetic method of intermediate 92-1
In flask, intermediate 3-1 (5g, 16.3mmol), N is added, N- dimethylformamides (30mL) are slowly added to N- Bromo- succimide (2.9g, 16.3mmol), is stirred at room temperature 5 hours, adds water, and filtering, filter cake is washed with methanol, dry, is produced Object 5.7g, yield 91%.
The synthetic method of compound 92
Consistent with the synthetic method of compound 1, raw materials used is intermediate 92-1 and 4- (9- carbazyls) phenyl boric acid, yield It is 57%.
Embodiment 12
The synthetic route of compound 93
Consistent with the synthetic method of compound 1, raw materials used is intermediate 92-1 and 9- phenyl -3- carbazole boric acid, yield It is 61%.
Embodiment 13
The synthetic route of compound 102
The synthetic method of intermediate 102-1
Consistent with the synthetic method of intermediate 102-1, raw materials used is the bromo- 4'- phenyl acetophenones of 2-, 3- amino -6- chlorine Pyridazine, yield 88%.
The synthetic method of compound 102
Consistent with the synthetic method of compound 1, raw materials used is intermediate 102-1 and 9- (4- phenyls) 3- carbazole boron Acid, yield 64%.
Embodiment 14
The synthetic route of compound 113
The synthetic method of intermediate 113-1
5,7- dihydros -7,7- dimethyl-indeno [2,1-b] carbazole (10g, 35.3mmol), bromine are added into reaction bulb Iodobenzene (12g, 42mmol), potassium tert-butoxide (7.9g, 70.6mmol), palladium (0.3g), tri-tert-butylphosphine tetrafluoroborate (0.8g) and toluene (150mL) is heated to reflux 24 hours under nitrogen protection, cooling, removes toluene, is added dichloromethane, washing, Dry, crude product crosses column, obtains 11g products, yield 71%.
The synthetic method of intermediate 113-2
In single-necked flask be added compound 113-2 (4.37g, 10mmol), connection boric acid frequency receive alcohol ester (3.0g, 12mmol), potassium acetate (3.0g), two triphenylphosphine palladium of dichloro (50mg), dioxane (60mL) are heated to 100 DEG C of reactions 12 Hour, silica gel is crossed while hot, is washed filter cake with dichloromethane, is revolved solvent evaporated, crude product is purified with column chromatography, obtains product 3.1g, yield 70%.
The synthetic method of compound 14
Consistent with the synthetic method of compound 1, raw materials used is intermediate 113-2 and intermediate 102-1, yield are 68%.
Embodiment 15-28
The preparation of organic electroluminescence device
OLED is prepared using the compound of embodiment
First, by electrically conducting transparent ito glass substrate 110 (carrying anode 120 above) (the limited public affairs of South China glass group share Department) it passes through successively：Deionized water, ethyl alcohol, acetone and deionized water were cleaned, then with oxygen plasma treatment 30 seconds.
Then, on ITO spin coating 45nm thickness PEDOT:PSS (Polyglycolic acid fibre-is poly- (styrene sulfonate)) is It is 30 minutes dry at 130,150 DEG C of hole injection layer.
Then, the TAPC that 45nm thickness is deposited on hole injection layer is hole mobile material 140.
Then, TCTA is deposited, forms the electronic barrier layer 150 of 5nm thickness.
Then, the luminescent layer 160 of 20nm thickness is deposited on electronic barrier layer, wherein shine based on the compounds of this invention Material, and the Ir (pq) for being 5% with weight ratio2Acac adulterates guest materials as phosphorescence.
Then, the TmPYPB of 55nm thickness is deposited on the light-emitting layer as electron transfer layer 170.
Finally, vapor deposition 0.6nm LiF are electron injecting layer 180 and 80nm Al as device cathodes 190.
Prepared device (structural schematic diagram is shown in Fig. 1) with Photo Research PR650 spectrometers start voltage be 1cd/m2, brightness 1000cd/m2Under to measure external quantum efficiency be such as table 1.
Comparative example 1
Device prepared by comparative example 1 is as the device preparation method of embodiment 15-28, in addition to replacing the present invention with CBP Compound as material of main part outside.
1 external quantum efficiency test result of table
Embodiment Compound Start voltage (V) External quantum efficiency (100%) Luminescent color
15 1 3.0 24 Feux rouges
16 3 2.9 23 Feux rouges
17 5 3.3 21 Feux rouges
18 22 3.7 22 Feux rouges
19 27 2.7 25 Feux rouges
20 30 2.8 25 Feux rouges
21 49 2.4 15 Feux rouges
22 54 2.7 20 Feux rouges
23 57 2.8 12 Feux rouges
24 74 2.5 13 Feux rouges
25 92 3.3 17 Feux rouges
26 93 2.9 12 Feux rouges
27 102 2.7 23 Feux rouges
28 113 2.8 19 Feux rouges
Comparative example 1 CBP 3.6 12 Feux rouges
As can be seen from the table, nitrogen heterocyclic of the invention is used for organic electroluminescence device, can reduce work Voltage improves device efficiency, is the phosphorescent light body material with excellent performance.As described above, the nitrogen heterocyclic of the present invention With high stability, the organic electroluminescence device of preparation has high efficiency and optical purity.
The structural formula of compound described in device is as follows：
The preferred embodiment of the present invention has been described in detail above.It should be appreciated that those skilled in the art without It needs creative work according to the present invention can conceive and makes many modifications and variations.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 solution, all should be in the protection domain being defined in the patent claims.

Claims (10)

1. a kind of nitrogen heterocyclic, which is characterized in that be the compound for having the following structure Formulas I：
Ar1-Ar5In it is at least one selected from substitution either unsubstituted C6-C30 carbazyl substitution or unsubstituted C18- The triaromatic amine base of C30, remaining aryl independently selected from hydrogen, substitution or unsubstituted C6-C30.
2. nitrogen heterocyclic as described in claim 1, which is characterized in that the aryl is selected from phenyl, cyano-phenyl, fluorine and takes For phenyl, xenyl, diphenyl substituted-phenyl, naphthalene, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,9- bis- Alkyl) fluorenyl, (9,9- bis- substitution either unsubstituted aryl) fluorenyl, 9,9- be Spirofluorene-based, substitution or unsubstituted dibenzo Thienyl and substitution or unsubstituted dibenzofuran group.
3. nitrogen heterocyclic as described in claim 1, which is characterized in that be the compound of following structural 1-118：
4. application of the nitrogen heterocyclic described in claim 1 in organic electroluminescence device.
5. a kind of organic electroluminescence device, which includes anode, cathode 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, electron transfer layer, which is characterized in that institute It states at least one layer in organic layer and contains nitrogen heterocyclic as described in claim 1.
6. organic electroluminescence device as claimed in claim 5, which is characterized in that azepine cyclisation as described in claim 1 Organic layer where closing object is at least one layer in luminescent layer, hole transmission layer or hole injection layer.
7. organic electroluminescence device as claimed in claim 5, which is characterized in that azacyclo- chemical combination described in claim 1 Object is used alone, or is used in mixed way with other compounds.
8. organic electroluminescence device as claimed in claim 5, which is characterized in that be used alone a kind of selected from such as claim The nitrogen heterocyclic of structural formula 1-118 described in 3, or simultaneously structure as claimed in claim 3 is selected from using two or more The nitrogen heterocyclic of formula 1-118.
9. organic electroluminescence device as claimed in claim 5, which is characterized in that the device include anode, hole injection layer, Hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and cathode contain one or more wherein in luminescent layer Nitrogen heterocyclic selected from structural formula 1-118 as claimed in claim 3.
10. organic electroluminescence device as claimed in claim 5, which is characterized in that the overall thickness of the organic layer is 1- 1000nm。
CN201810122941.0A 2018-02-07 2018-02-07 A kind of nitrogen heterocyclic and application thereof and organic electroluminescence device Pending CN108358932A (en)

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CN112940013A (en) * 2019-12-11 2021-06-11 广东阿格蕾雅光电材料有限公司 Arylamine compound of imidazopyridine and application thereof
CN113831343A (en) * 2021-07-23 2021-12-24 安徽秀朗新材料科技有限公司 Thermal activity delayed fluorescent material based on imidazopyrazine receptor material, preparation method and application thereof
CN116554207A (en) * 2023-05-18 2023-08-08 烟台先进材料与绿色制造山东省实验室 Organic compound containing imidazo-aza-phenyl group, and preparation method and application thereof

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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

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CN106518893A (en) * 2015-09-09 2017-03-22 三星电子株式会社 Condensed cyclic comopund and organic light-emitting device including the same
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

Cited By (7)

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Publication number Priority date Publication date Assignee Title
CN112940013A (en) * 2019-12-11 2021-06-11 广东阿格蕾雅光电材料有限公司 Arylamine compound of imidazopyridine and application thereof
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CN112940013B (en) * 2019-12-11 2024-03-26 广东阿格蕾雅光电材料有限公司 Aromatic amine compound of imidazopyridine and application thereof
CN113831343A (en) * 2021-07-23 2021-12-24 安徽秀朗新材料科技有限公司 Thermal activity delayed fluorescent material based on imidazopyrazine receptor material, preparation method and application thereof
CN113831343B (en) * 2021-07-23 2023-09-05 安徽秀朗新材料科技有限公司 Thermal activity delayed fluorescent material based on imidazopyrazine receptor material, preparation method and application thereof
CN116554207A (en) * 2023-05-18 2023-08-08 烟台先进材料与绿色制造山东省实验室 Organic compound containing imidazo-aza-phenyl group, and preparation method and application thereof

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Application publication date: 20180803