CN104744346A - Dianthracene compounds containing pyridyl at terminals and application thereof - Google Patents

Dianthracene compounds containing pyridyl at terminals and application thereof Download PDF

Info

Publication number
CN104744346A
CN104744346A CN201410111136.XA CN201410111136A CN104744346A CN 104744346 A CN104744346 A CN 104744346A CN 201410111136 A CN201410111136 A CN 201410111136A CN 104744346 A CN104744346 A CN 104744346A
Authority
CN
China
Prior art keywords
compound
formula
anthracene compounds
aromatic group
replacement
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201410111136.XA
Other languages
Chinese (zh)
Other versions
CN104744346B (en
Inventor
黄达
圣磊
阮群奇
谭玉东
靳灿辉
孙仲猛
曹林法
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Anhui Jingkai Electronic Materials Co.,Ltd.
Original Assignee
JIANGSU HECHENG NEW MATERIALS Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by JIANGSU HECHENG NEW MATERIALS Co Ltd filed Critical JIANGSU HECHENG NEW MATERIALS Co Ltd
Priority to CN201410111136.XA priority Critical patent/CN104744346B/en
Publication of CN104744346A publication Critical patent/CN104744346A/en
Application granted granted Critical
Publication of CN104744346B publication Critical patent/CN104744346B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/127—Preparation from compounds containing pyridine rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Pyridine Compounds (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The invention provides dianthracene compounds shown in a general formula I in the specification. In the general formula I, L1 and L2 independently represent single bonds, substituted or unsubstituted heterocyclic aromatic groups of C2-C60 or substituted or unsubstituted hydrocarbon aromatic groups of C6-C60; L3 represents a substituted or unsubstituted heterocyclic aromatic group of C2-C60 or a substituted or unsubstituted hydrocarbon aromatic group of C6-C60; R10, R11, R12, R13, R14, R15, R16, R17, R18, R21, R23, R24, R25, R26, R27 and R28 independently represent hydrogen, halogen and substituted or unsubstituted alkyl or alkoxy of C1-C10. The compounds have good luminescence properties, high electron transport capacities and terrific solubility and can be used in luminescent materials, electron transport materials and hole-blocking materials in the electroluminescence field. The invention also provides an organic electroluminescence device at least comprising a pair of electrodes and organic luminescent media between the electrodes. The organic luminescent media at least comprise the dianthracene compounds.

Description

End is containing two anthracene compounds and application thereof of pyridyl
Technical field
The present invention relates to the two anthracene compounds of a kind of end containing pyridyl, this two anthracenes compounds can be applied to electroluminescent field.
Background technology
Organic electroluminescent LED (OLED) from Deng Qingyun in 1987 at Applied Physics bulletin (Appl.Phys.Lett., 1987,51,913) since publishing an article on, because its drive from main light emission, low-voltage direct-current, the advantage of all solidstate, be subject to academia and industry member is paid attention to greatly.In display field, OLED has the feature of cathode tube and liquid-crystal display concurrently, and visual angle is large, low in energy consumption, bright in luster, is described as dreamlike indicating meter of future generation.At lighting field, OLED, as the technology that uniquely really can realize area source, has luminous soft not dazzling, environmental protection, the healthy light source of the light that gets close to nature most, to be described as in human development history the lighting source of most energy-saving health.
High performance luminescent material is adopted to be the important foundation preparing OLED.Present OLED material is mainly divided into small molecule material and macromolecular material, the easy crystallization of small molecule material, and poorly soluble, macromolecular material luminous efficiency is low, is unfavorable for suitability for industrialized production.So find one and have higher photoluminescence efficiency, the organic materials with good solubility becomes the key issue of OLED material technical field.
The anthracene compounds found now, is typical luminescence system, compares the compound being suitable as electroluminescent material.9,10-diaryl anthracene has satisfactory stability and luminous efficiency, is excellent blue emitting material.2,9 '-two anthracene compounds is due to splendid steric hindrance effect, and make such compound film spectrum compare the red shift of PL solution spectrum very little, light emitting main peak remains on about 450nm.Meanwhile, document (Chem.Lett., 2008,37,1150-1151) also reports that this compounds has splendid thermostability.
But, in existing bibliographical information, 2,9 '-two anthracene compounds mostly is hydrocarbon type compound, and only possess single luminescent properties, transmission performance is poor, being applied to electroluminescent field can cause device power consumption to increase, the problems such as product life shortens, chromaticity distortion, are badly in need of the material that exploitation has luminescent properties and transmission performance concurrently.CN101395105A reports the two anthracene compounds that a class contains carbazole and benzoglyoxaline group, but complex synthetic route, the low purification difficult of solubleness, is unfavorable for suitability for industrialized production.
Compound containing pyridyl is typical electron deficiency system, has good to accept electronic capability.The class that document (Chem.Mater., 2011,23,621-630) is reported contains the electron transport material of pyridine groups, shows very high thermostability, excellent hole barrier and exciton blocking capability, splendid electron transport ability.Document (Adv.Funct.Mater., 2011,21, the electron-like transport material containing pyridine groups 1881-1886) reported, show excellent electronic transmission performance and electron injection performance, such material has good electrochemical stability simultaneously, increases the service life.
The present invention, on the basis with twist structured two anthracene derivatives, introduces the pyridyl of electron deficiency, makes compound of the present invention have good luminescent properties and good transmission performance concurrently.Overcome the shortcoming of traditional hydrocarbon type two anthracene compounds transmission performance difference.
In addition, consider the difficulty or ease of suitability for industrialized production, compound of the present invention is many containing alkyl group.
Summary of the invention
The object of the invention is the fluorescent chemicals that proposition one class is novel, described fluorescent chemicals is on the basis with twist structured two anthracene derivatives, introduce the pyridyl of electron deficiency, compound of the present invention is made to have good luminescent properties and good transmission performance concurrently, can as the luminescent layer in organic light emitting medium, electron transfer layer and hole blocking layer.
In order to complete foregoing invention object, the invention provides a kind of two anthracene compounds as shown in formula I:
Wherein,
L 1and L 2identical or different, represent the replacement of singly-bound, C2-C60 or the replacement of unsubstituting heterocycle type aromatic group or C6-C60 with being mutually independent or not replacing hydrocarbon type aromatic group;
L 3represent the replacement of C2-C60 or the replacement of unsubstituting heterocycle type aromatic group or C6-C60 independently or do not replace hydrocarbon type aromatic group;
R 10, R 11, R 12, R 13, R 14, R 15, R 16, R 17, R 18, R 21, R 23, R 24, R 25, R 26, R 27and R 28identical or different, represent hydrogen with being mutually independent, halogen, the substituted or unsubstituted alkyl of C1-C10, or the substituted or unsubstituted alkoxyl group of C1-C10.
In some embodiments, described L 1with L 2identical, represent singly-bound, the replacement of C2-C60 or the replacement of unsubstituting heterocycle type aromatic group or C6-C60 or do not replace hydrocarbon type aromatic group.
In some embodiments, described L 1, L 2and L 3be expressed as follows aromatic group with being mutually independent:
Wherein,
Ra, Rb, Rc, Rd are identical or different, represent hydrogen with being mutually independent, halogen, the replacement of C1-C30 or unsubstituted alkyl, or the replacement of C1-C30 or unsubstituted alkoxyl group.
In some embodiments, described L 1, L 2and L 3be expressed as follows aromatic group with being mutually independent:
Wherein,
Ra, Rb, Rc can be hydrogen, halogen, the substituted or unsubstituted alkyl of C1-C30, or the substituted or unsubstituted alkoxyl group of C1-C30.
In some embodiments, described L1 and L2 is independently from each other
Described L3 is selected from
In some embodiments, R 10be selected from hydrogen, methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-or the tertiary butyl.
In some embodiments, R 26and R 27be selected from methyl, ethyl or the tertiary butyl independently of one another.
Due to the compound containing pyridyl, be typical electron deficiency system, have and good accept electronic capability.Therefore, the present invention, on the basis with twist structured two anthracene derivatives, introduces the pyridyl of electron deficiency, makes, in compound hinge structure of the present invention, to have good luminescent properties and good transmission performance.Overcome the shortcoming of traditional hydrocarbon type two anthracene compounds transmission performance difference.Further, compound of the present invention is many containing alkyl group, is more conducive to suitability for industrialized production.
Organic compound of the present invention is used as luminescent material in organic electroluminescence device, electron transport material or hole barrier materials.
On the other hand, present invention also offers the two kinds of synthetic methods providing generalformulaⅰcompound.
A kind of method one: method preparing two anthracene compounds of the present invention, comprising:
1) by formula 4 compound
With formula 5 compound
By being obtained by reacting formula 2 compound
2) by formula 6 compound
With formula 7 compound
The intermediate of formula 8 is obtained through suzuki linked reaction
The intermediate of described formula 8 is obtained by reacting formula 3 compound by boration
3) described formula 2 compound and described formula 3 compound are obtained the two anthracene compounds of described end as shown in formula I containing pyridyl by suzuki linked reaction
Wherein,
X 1, X 2, X 3for halogen.
Method two: a kind of method preparing two anthracene compounds of the present invention, comprising:
1) by formula 2 compound
With formula 9 compound
Formula 10 compound is obtained by linked reaction
Formula 11 compound is obtained through bromination reaction
2) described formula 11 compound and formula 12 compound
Formula 13 compound is obtained by linked reaction
Formula 14 compound is obtained through bromination reaction
3) described formula 14 compound and formula 15 compound
The two anthracene compounds of the end as shown in formula I containing pyridyl are obtained by linked reaction
Wherein,
X 4for halogen.
Another aspect of the present invention provides is preparing in organic electroluminescence device according to two anthracene compounds as shown in formula I of the present invention the purposes be used as in luminescent material, electron transport material or hole barrier materials.
Another aspect of the present invention provides a kind of organic electroluminescence device, comprises the organic light emitting medium between pair of electrodes and electrode, comprises at least one two anthracene compounds of the present invention in described organic light emitting medium.
In some embodiments, described two anthracene compounds are arranged in the electron transfer layer of described organic light emitting medium.
In some embodiments, described two anthracene compounds are arranged in the luminescent layer of described organic light emitting medium.
In some embodiments, described two anthracene compounds are as blue emitting material.
In some embodiments, described two anthracene compounds are as the main body luminescent material of described luminescent layer.
The invention provides a kind of comparative approach of material electronics transmission performance, adopt the method for quantum chemistry, in certain accuracy rating, by the electron recombination energy of comparative compound, obtain the difference of the electronic transmission performance between compound.
Organic compound of the present invention has good transmission performance and luminescent properties, can be used as luminescent layer, electron transfer layer and hole blocking layer in organic electroluminescence device.
Accompanying drawing explanation
Fig. 1 shows the NMR data according to compound of the present invention of synthesis in embodiment 34.
Fig. 2 shows the NMR data according to compound of the present invention of synthesis in embodiment 35.
Fig. 3 shows the NMR data according to compound of the present invention of synthesis in embodiment 36.
Fig. 4 shows the NMR data according to compound of the present invention of synthesis in embodiment 37.
Fig. 5 shows the NMR data according to compound of the present invention of synthesis in embodiment 38.
Fig. 6 shows the NMR data according to compound of the present invention of synthesis in embodiment 41.
Fig. 7 shows the NMR data according to compound of the present invention of synthesis in embodiment 42.
Fig. 8 shows the NMR data according to compound of the present invention of synthesis in embodiment 43.
Fig. 9 shows the NMR data according to compound of the present invention of synthesis in embodiment 44.
Figure 10 shows the NMR data according to compound of the present invention of synthesis in embodiment 47.
Figure 11 shows the NMR data according to compound of the present invention of synthesis in embodiment 48.
Figure 12 shows the NMR data according to compound of the present invention of synthesis in embodiment 49.
Figure 13 shows the spectroscopic data according to compound of the present invention of synthesis in embodiment 41.
Figure 14 shows the spectroscopic data according to compound of the present invention of synthesis in embodiment 44.
Embodiment
Embodiment 1
The preparation of compound H P-NP14-PY4
Isosorbide-5-Nitrae-dibromine naphthalene (4mmol, 1.14g), pyridine-4-boric acid (4mmol, 0.49g) and tetrakis triphenylphosphine palladium (100mg) are mixed, adds toluene (6ml)/ethanol (6ml)/2M Na 2cO 3(1ml) mixing solutions.This reaction system is stirred 4 hours under 100 degrees Celsius, is then cooled to room temperature.By water (50ml) diluting reaction system also with ethyl acetate (3*50ml) extraction.Organic phase anhydrous magnesium sulfate drying, concentrated organic phase also crosses post with silica gel, obtains shallow white solid HP-NP14-PY4(0.56g, productive rate 50%).
Embodiment 2
The preparation of compound H P-NP14-PY3
Replace pyridine-4-boric acid except with pyridine-3-boric acid, through the reaction identical with embodiment 1, obtain compound H P-NP14-PY3.
Embodiment 3
The preparation of compound H P-NP14-PY2
Replace pyridine-4-boric acid except with pyridine-2-boric acid, through the reaction identical with embodiment 1, obtain compound H P-NP14-PY2.
Embodiment 4
The preparation of compound H P-2PH44-PY4
Replace Isosorbide-5-Nitrae-dibromine naphthalene except with 4,4-'-dibromobiphenyl, through the reaction identical with embodiment 1, obtain compound H P-2PH44-PY4.
Embodiment 5
The preparation of compound H P-2PH44-PY3
Replace Isosorbide-5-Nitrae-dibromine naphthalene except with 4,4-'-dibromobiphenyl, replace pyridine-4-boric acid with pyridine-3-boric acid, through the reaction identical with embodiment 1, obtain compound H P-2PH44-PY3.
Embodiment 6
The preparation of compound H P-2PH44-PY2
Replace Isosorbide-5-Nitrae-dibromine naphthalene except with 4,4-'-dibromobiphenyl, replace pyridine-4-boric acid with pyridine-2-boric acid, through the reaction identical with embodiment 1, obtain compound H P-2PH44-PY3.
Embodiment 7
The preparation of compound H P-PH44-PY4
Isosorbide-5-Nitrae-dibromine naphthalene is replaced except with Isosorbide-5-Nitrae-dibromobenzene, through the reaction identical with embodiment 1, obtain compound H P-PH44-PY4.
Embodiment 8
The preparation of compound H P-PH44-PY3
Replace Isosorbide-5-Nitrae-dibromine naphthalene except with 4,4-'-dibromobiphenyl, replace pyridine-4-boric acid with pyridine-3-boric acid, through the reaction identical with embodiment 1, obtain compound H P-PH44-PY3.
Embodiment 9
The preparation of compound H P-PH44-PY2
Replace Isosorbide-5-Nitrae-dibromine naphthalene except with 4,4-'-dibromobiphenyl, replace pyridine-4-boric acid with pyridine-2-boric acid, through the reaction identical with embodiment 1, obtain compound H P-PH44-PY2.
Embodiment 10
The preparation of compound H P-AN-NP14-PY4
By HP-NP14-PY4(1mmol, 284mg) be dissolved into anhydrous tetrahydrofuran solution (10ml), 1.6M butyl lithium solution (1mmol is dripped under-78 degrees Celsius, 0.63ml), 2-bromo anthraquinone (0.5mmol, 144mg) is then added, be warming up to stirring at room temperature 2 hours, add water (20ml) and extract with methylene dichloride (3*40ml), anhydrous magnesium sulfate drying organic phase, concentrating and obtain dark solid.Dark solid be dissolved in acetic acid (30ml), and add potassiumiodide (3mmol, 500mg), a hydration sodium hypophosphite (6mmol, 1.1g), 120 degrees Celsius are stirred 3 hours, are then cooled to room temperature, have solid to separate out.Solid cold water (3*20ml) after filtering is washed, dries to obtain white solid HP-AN-NP14-PY4(300mg, productive rate 90%).
Embodiment 11
Compound H P -aN -nP14 -the preparation of PY3
Except replacing HP-NP14-PY4 with HP-NP14-PY3, through the reaction identical with embodiment 10, obtain compound H P-AN-NP14-PY3.
Embodiment 12
The preparation of compound H P-AN-NP14-PY2
Except replacing HP-NP14-PY4 with HP-NP14-PY2, through the reaction identical with embodiment 10, obtain compound H P-AN-NP14-PY2.
Embodiment 13
Compound H P -aN -pH44 -the preparation of PY4
Except replacing HP-NP14-PY4 with HP-PH44-PY4, through the reaction identical with embodiment 10, obtain compound H P-AN-PH44-PY4.
Embodiment 14
The preparation of compound H P-AN-PH44-PY3
Except replacing HP-NP14-PY4 with HP-PH44-PY3, through the reaction identical with embodiment 10, obtain compound H P-AN-PH44-PY3.
Embodiment 15
Compound H P -aN -2PH44 -the preparation of PY4
Except replacing HP-NP14-PY4 with HP-2PH44-PY4, through the reaction identical with embodiment 10, obtain compound H P-AN-2PH44-PY4.
Embodiment 16
The preparation of compound H P-AN-2PH44-PY3
Except replacing HP-NP14-PY4 with HP-2PH44-PY3, through the reaction identical with embodiment 10, obtain compound H P-AN-2PH44-PY3.
Embodiment 17
The preparation of compound H P-ANme-PH44-PY4
Except replacing HP-NP14-PY4 with HP-PH44-PY4, replacing 2-bromo anthraquinone with bromo-6 tectoquinones of 2-, through the reaction identical with embodiment 10, obtaining compound H P-ANme-PH44-PY4.
Embodiment 18
The preparation of compound H P-ANme-PH44-PY3
Except replacing HP-NP14-PY4 with HP-PH44-PY3, replacing 2-bromo anthraquinone with bromo-6 tectoquinones of 2-, through the reaction identical with embodiment 10, obtaining compound H P-ANme-PH44-PY3.
Embodiment 19
The preparation of compound H P-ANet-2PH44-PY4
Except replacing HP-NP14-PY4 with HP-2PH44-PY4, replacing 2-bromo anthraquinone by bromo-6 EAQ of 2-, through the reaction identical with embodiment 10, obtaining compound H P-ANet-2PH44-PY4.
Embodiment 20
The preparation of compound H P-AN9-PH
By Isosorbide-5-Nitrae-dibromoanthracene (4mmol, 1.34g), phenylo boric acid (4mmol, 0.49g) and tetrakis triphenylphosphine palladium (100mg) mixing, add the mixing solutions of toluene (6ml)/ethanol (6ml)/2M Na2CO3 (1ml).This reaction system is stirred 4 hours 100 degrees Celsius of lower nitrogen protections, is then cooled to room temperature.By water (50ml) diluting reaction system also with ethyl acetate (3*50ml) extraction.Organic phase anhydrous magnesium sulfate drying, concentrated organic phase also crosses post with silica gel, obtains yellow solid HP-AN9-PH(1.06, productive rate 80%).
Embodiment 21
The preparation of compound H P-AN9-PH44-1
Replace phenylo boric acid except with 4-methylphenylboronic acid, through the reaction identical with embodiment 20, obtain compound H P-AN9-PH44-1.
Embodiment 22
The preparation of compound H P-AN9-PH43-1
Replace phenylo boric acid except with 3-methylphenylboronic acid, through the reaction identical with embodiment 20, obtain compound H P-AN9-PH43-1.
Embodiment 23
Compound H P -aN9 -pH42 -the preparation of 1
Replace phenylo boric acid except with 2-methylphenylboronic acid, through the reaction identical with embodiment 20, obtain compound H P-AN9-PH42-1.
Embodiment 24
The preparation of compound H P-AN9-PH44-4t
Replace phenylo boric acid except with 4-tert-butylbenzeneboronic acid, through the reaction identical with embodiment 20, obtain compound H P-AN9-PH44-4t.
Embodiment 25
The preparation of compound H P-AN9-2PH
Replace phenylo boric acid except with biphenyl-4-boric acid, through the reaction identical with embodiment 20, obtain compound H P-AN9-2PH.Embodiment 26
The preparation of compound H P-AN9-N
Except using 4-(N Phenyl-benzoimidazol)-4-boric acid replacement phenylo boric acid, through the reaction identical with embodiment 20, obtain compound H P-AN9-N.
Embodiment 27
The preparation of compound H P-AN9B-PH
By compound H P-AN9-PH(3mmol; 1.00g) be dissolved in anhydrous tetrahydro furan (25ml), under-78 degrees Celsius, drip 1.6M butyl lithium solution (3.6mmol, 2.3ml); nitrogen protection is stirred 2 and was as a child dripped trimethyl borate (4.5mmol; 0.5ml), continue nitrogen protection and stir 2 hours, 1M hydrochloric acid soln (30ml) quencher is reacted; add water (100ml) precipitation precipitation; wash solid with normal hexane (3*20ml), obtain white powder HP-AN9B-PH(0.72g, productive rate 81%).Embodiment 28
The preparation of compound H P-AN9B-PH44-1
Except replacing HP-AN9-PH with HP-AN9-PH44-1, through the reaction identical with embodiment 27, obtain compound H P-AN9B-PH44-1.
Embodiment 29
Compound H P -aN9B -pH43 -the preparation of 1
Except replacing HP-AN9-PH with HP-AN9-PH43-1, through the reaction identical with embodiment 27, obtain compound H P-AN9B-PH43-1.
Embodiment 30
The preparation of compound H P-AN9B-PH42-1
Except replacing HP-AN9-PH with HP-AN9-PH42-1, through the reaction identical with embodiment 27, obtain compound H P-AN9B-PH42-1.
Embodiment 31
The preparation of compound H P-AN9B-PH44-4t
Except replacing HP-AN9-PH with HP-AN9-PH44-4t, through the reaction identical with embodiment 27, obtain compound H P-AN9B-PH44-4t.
Embodiment 32
The preparation of compound H P-AN9B-2PH
Except replacing HP-AN9-PH with HP-AN9-2PH, through the reaction identical with embodiment 27, obtain compound H P-AN9B-2PH.
Embodiment 33
The preparation of compound H P-AN9B-N
Except replacing HP-AN9-PH with HP-AN9-N, through the reaction identical with embodiment 27, obtain compound H P-AN9B-N.
Embodiment 34
The preparation of compound H P-L-NP14-PY4-L-PH43-1
By [HP-AN-NP14-PY4] (1mmol, 663mg), [HP-AN9B-PH43-1] (1mmol, 312mg) and tetrakis triphenylphosphine palladium (25mg) mixing, add toluene (2ml)/ethanol (2ml)/2M Na 2cO 3(0.5ml) mixing solutions.This reaction system is stirred 4 hours under 100 degrees Celsius, is then cooled to room temperature.By water (40ml) diluting reaction system also with ethyl acetate (3*40ml) extraction.Organic phase anhydrous magnesium sulfate drying, concentrated organic phase also crosses post with silica gel, obtains shallow white solid HP-L-NP14-PY4-L-PH43-1(680mg, productive rate 80%).
The NMR data of product are shown in Figure 1.
Embodiment 35
The preparation of compound H P-L-NP14-PY4-L-PH44-1
Except replacing HP-AN9B-PH43-1 with HP-AN9B-PH44-1, through the reaction identical with embodiment 34, obtain compound H P-L-NP14-PY4-L-PH44-1.
The NMR data of product are shown in Figure 2.
Embodiment 36
The preparation of compound H P-L-NP14-PY3-L-PH43-1
Except replacing HP-AN-NP14-PY4 with HP-AN-NP14-PY3, through the reaction identical with embodiment 34, obtain compound H P-L-NP14-PY3-L-PH43-1.
The NMR data of product are shown in Figure 3.
Embodiment 37
The preparation of compound H P-L-NP14-PY2-L-PH43-1
Except replacing HP-AN-NP14-PY4 with HP-AN-NP14-PY2, through the reaction identical with embodiment 34, obtain compound H P-L-NP14-PY2-L-PH43-1.
The NMR data of product are shown in Figure 4.
Embodiment 38
The preparation of compound H P-L-2PH44-PY4-L-PH44-4t
Except replacing HP-AN9B-PH43-1 with HP-AN9B-PH44-4t, replacing HP-AN-NP14-PY4 with HP-AN-2PH44-PY4, through the reaction identical with embodiment 34, obtaining compound H P-L-NP14-PY4-L-PH44-1.
The NMR data of product are shown in Figure 5.
Embodiment 39
The preparation of compound H P-L-2PH44-PY3-L-PH44-4t
Except replacing HP-AN9B-PH43-1 with HP-AN9B-PH44-4t, replacing HP-AN-NP14-PY4 with HP-AN-2PH44-PY3, through the reaction identical with embodiment 34, obtaining compound H P-L-2PH44-PY3-L-PH44-4t.MS(EI)m/z=944.41（M +）
Embodiment 40
The preparation of compound H P-L2-2PH44-PY4-L-2PH
Except replacing HP-AN9B-PH43-1 with HP-AN9B-2PH, replacing HP-AN-NP14-PY4 with HP-ANet-2PH44-PY4, through the reaction identical with embodiment 34, obtaining compound H P-L2-2PH44-PY4-L-2PH.MS(EI)m/z=992.41（M +）
Embodiment 41
The preparation of compound H P-L2-2PH44-PY4-L-N
Except replacing HP-AN9B-PH43-1 with HP-AN9B-N, replacing HP-AN-NP14-PY4 with HP-ANet-2PH44-PY4, through the reaction identical with embodiment 34, obtaining compound H P-L2-2PH44-PY4-L-N.
The NMR data of product are shown in Figure 6.
The spectroscopic data of product is shown in Figure 13.
Embodiment 42
The preparation of compound H P-L-PH44-PY4-L-PH
Except replacing HP-AN9B-PH43-1 with HP-AN9B-PH, replacing HP-AN-NP14-PY4 with HP-AN-PH44-PY4, through the reaction identical with embodiment 34, obtaining compound H P-L-PH44-PY4-L-PH.
The NMR data of product are shown in Figure 7.
Embodiment 43
The preparation of compound H P-L-PH44-PY3-L-PH
Except replacing HP-AN9B-PH43-1 with HP-AN9B-PH, replacing HP-AN-NP14-PY4 with HP-AN-PH44-PY3, through the reaction identical with embodiment 34, obtaining compound H P-L-PH44-PY3-L-PH.
The NMR data of product are shown in Figure 8.
Embodiment 44
The preparation of compound H P-L-PH44-PY4-L-PH43-1
Except replacing HP-AN-NP14-PY4 with HP-AN-PH44-PY4, through the reaction identical with embodiment 34, obtain compound H P-L-PH44-PY4-L-PH43-1.
The NMR data of product are shown in Figure 9.
The spectroscopic data of product is shown in Figure 14.
Embodiment 45
Compound H P -l -pH44 -pY4 -l -pH42 -the preparation of 1
Except replacing HP-AN9B-PH43-1 with HP-AN9B-PH42-1, replacing HP-AN-NP14-PY4 with HP-AN-PH44-PY4, through the reaction identical with embodiment 34, obtaining compound H P-L-PH44-PY4-L-PH42-1.MS(EI)m/z=750.30（M +）
Embodiment 46
The preparation of compound H P-L-PH44-PY4-L-2PH
Except replacing HP-AN9B-PH43-1 with HP-AN9B-2PH, replacing HP-AN-NP14-PY4 with HP-AN-PH44-PY4, through the reaction identical with embodiment 34, obtaining compound H P-L-PH44-PY4-L-2PH.
MS(EI)m/z=812.32（M +）
Embodiment 47
The preparation of compound H P-L-PH44-PY4-L-PH44-4t
Except replacing HP-AN9B-PH43-1 with HP-AN9B-PH44-4t, replacing HP-AN-NP14-PY4 with HP-AN-PH44-PY4, through the reaction identical with embodiment 34, obtaining compound H P-L-PH44-PY4-L-PH44-4t.
The NMR data of product are shown in Figure 10.
Embodiment 48
The preparation of compound H P-L1-PH44-PY4-L-PH44-4t
Except replacing HP-AN9B-PH43-1 with HP-AN9B-PH44-4t, replacing HP-AN-NP14-PY4 with HP-ANme-PH44-PY4, through the reaction identical with embodiment 34, obtaining compound H P-L1-PH44-PY4-L-PH44-4t.
The NMR data of product are shown in Figure 11.
Embodiment 49
The preparation of compound H P-L1-PH44-PY3-L-PH44-4t
Except replacing HP-AN9B-PH43-1 with HP-AN9B-PH44-4t, replacing HP-AN-NP14-PY4 with HP-ANme-PH44-PY3, through the reaction identical with embodiment 34, obtaining compound H P-L1-PH44-PY3-L-PH44-4t.
The NMR data of product are shown in Figure 12.
Embodiment 50
The acquisition of the compound H P-L-NP14-PY4-L-PH43-1 electron recombination energy that embodiment 34 obtains
The molecular coordinates of compound [HP-L-NP14-PY4-L-PH43-1] is input in quantum chemistry software, at b3lyp/6-31G (d, p) optimize under, obtain the ground state energy (E1) of compound respectively, containing the vertical excited energy (E2) of an electronics, containing the adiabatic excited energy (E3) of an electronics, based on the neutral molecule energy (E4) of adiabatic excited state configuration, obtained the electron recombination energy E of this compound by Reorganization Energy calculation formula E=|E1-E4|+|E2-E3|.
Embodiment 51
The acquisition of the compound H P-L1-PH44-PY3-L-PH44-4t electron recombination energy that embodiment 49 obtains
Replace HP-L-NP14-PY4-L-PH43-1 except with the molecular coordinates of compound [HP-L1-PH44-PY3-L-PH44-4t], through the operation identical with embodiment 48, obtain compound [HP-L1-PH44-PY3-L-PH44-4t] electron recombination energy.
Comparative example
The acquisition of compd A ND electron recombination energy
Except substituting HP-L-NPl4-PY4-L-PH43-l with the molecular coordinates of AND, through the operation identical with embodiment 48, obtain compd A ND electron recombination energy.
Electron recombination energy data obtained above are as shown in following table says:
El(a.u.) E2(a.u.) E3(a.u.) E4(a.u.) E(a.u.)
Embodiment 50 1771.0603463 1771.0806258 1771.0887808 1771.0556912 0.0128l
Embodiment 51 2464.2517535 2464.2772045 2464.2834156 2464.2467387 0.01123
Comparative example 1308.9535859 1308.9672428 1308.9751160 1308.9472085 0.01425
According to document (J.Phvs.Chem.A2003,107,524l-5251), electron recombination can be less, and electronic mobility is higher.Can see from upper table, the electron recombination of embodiment 50 and embodiment 5l can be better than conventional AND, shows that compound of the present invention also can be applied in electroluminescent field as electron transport material.
Although describe the present invention in conjunction with the embodiments, the present invention is not limited to above-described embodiment, should be appreciated that, under the guiding of the present invention's design, those skilled in the art can carry out various amendment and improvement, and claims summarise scope of the present invention.

Claims (16)

1. two anthracene compounds as shown in formula I:
Wherein,
L 1and L 2identical or different, represent the replacement of singly-bound, C2-C60 or the replacement of unsubstituting heterocycle type aromatic group or C6-C60 with being mutually independent or not replacing hydrocarbon type aromatic group;
L 3represent the replacement of C2-C60 or the replacement of unsubstituting heterocycle type aromatic group or C6-C60 independently or do not replace hydrocarbon type aromatic group;
R 10, R 11, R 12, R 13, R 14, R 15, R 16, R 17, R 18, R 21, R 23, R 24, R 25, R 26, R 27and R 28identical or different, represent hydrogen with being mutually independent, halogen, the substituted or unsubstituted alkyl of C1-C10, or the substituted or unsubstituted alkoxyl group of C1-C10.
2. two anthracene compounds according to claim 1, is characterized in that, described L 1with L 2identical, represent singly-bound, the replacement of C2-C60 or the replacement of unsubstituting heterocycle type aromatic group or C6-C60 or do not replace hydrocarbon type aromatic group.
3. two anthracene compounds according to any one of claim 1 to 2, is characterized in that, described L 1, L 2and L 3be expressed as follows aromatic group with being mutually independent:
Wherein,
Ra, Rb, Rc, Rd, identical or different, represent hydrogen with being mutually independent, halogen, the replacement of D1-C30 or unsubstituted alkyl, or the replacement of C1-C30 or unsubstituted alkoxyl group.
4. two anthracene compounds according to any one of claim 1 to 2, described L 1, L 2and L 3be expressed as follows aromatic group with being mutually independent:
Wherein,
Ra, Rb, Rc can be hydrogen, halogen, the substituted or unsubstituted alkyl of C1-C30, or the substituted or unsubstituted alkoxyl group of C1-C30.
5. two anthracene compounds according to claim 1 and 2, wherein, described L1 and L2 is independently from each other
L711 or L723;
Described L3 is selected from
6. two anthracene compounds, wherein R according to claim 1 and 2 10be selected from hydrogen, methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-or the tertiary butyl.
7. two anthracene compounds, wherein R according to claim 1 and 2 26and R 27be selected from methyl, ethyl or the tertiary butyl independently of one another.
8. two anthracene compounds according to claim 1 and 2, described two anthracene compounds be selected from by
the group of composition.
9. prepare a method for two anthracene compounds according to any one of claim 2 and 5-8, comprising:
1) by formula 4 compound
With formula 5 compound
By being obtained by reacting formula 2 compound
2) by formula 6 compound
With formula 7 compound
The intermediate of formula 8 is obtained through suzuki linked reaction
the intermediate of described formula 8 is obtained by reacting formula 3 compound by boration
3) described formula 2 compound and described formula 3 compound are obtained the two anthracene compounds of described end as shown in formula I containing pyridyl by suzuki linked reaction
Wherein,
X 1, X 2, X 3for halogen.
10. prepare a method for the two anthracene compounds as shown in formula I according to any one of claim 1-6, comprising:
1) by formula 2 compound
With formula 9 compound
Formula 10 compound is obtained by linked reaction
formula 11 compound is obtained through bromination reaction
2) described formula 11 compound and formula 12 compound
Formula 13 compound is obtained by linked reaction
Formula 14 compound is obtained through bromination reaction
3) described formula 14 compound and formula 15 compound
The two anthracene compounds of the end as shown in formula I containing pyridyl are obtained by linked reaction
Wherein,
X 4for halogen.
11. two anthracene compounds as shown in formula I according to any one of claim 1-6 are preparing in organic electroluminescence device the purposes be used as in luminescent material, electron transport material or hole barrier materials.
12. 1 kinds of organic electroluminescence devices, comprise the organic light emitting medium between pair of electrodes and electrode, comprise at least one by two anthracene compounds one of claim 1-6 Suo Shu in described organic light emitting medium.
13. organic electroluminescence devices according to claim 10, is characterized in that, described two anthracene compounds are arranged in the electron transfer layer of described organic light emitting medium.
14. organic electroluminescence devices according to claim 10, is characterized in that, described two anthracene compounds are arranged in the luminescent layer of described organic light emitting medium.
15. organic electroluminescence devices according to claim 12, is characterized in that, described two anthracene compounds are as blue emitting material.
16. organic electroluminescence devices according to claim 12, is characterized in that, described two anthracene compounds are as the main body luminescent material of described luminescent layer.
CN201410111136.XA 2013-12-27 2014-03-24 Dianthracene compound with pyridyl at tail end and application thereof Active CN104744346B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201410111136.XA CN104744346B (en) 2013-12-27 2014-03-24 Dianthracene compound with pyridyl at tail end and application thereof

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CN201310738926 2013-12-27
CN2013107389266 2013-12-27
CN201410111136.XA CN104744346B (en) 2013-12-27 2014-03-24 Dianthracene compound with pyridyl at tail end and application thereof

Publications (2)

Publication Number Publication Date
CN104744346A true CN104744346A (en) 2015-07-01
CN104744346B CN104744346B (en) 2021-03-02

Family

ID=53584699

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201410111136.XA Active CN104744346B (en) 2013-12-27 2014-03-24 Dianthracene compound with pyridyl at tail end and application thereof

Country Status (1)

Country Link
CN (1) CN104744346B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109251176A (en) * 2017-07-12 2019-01-22 北京鼎材科技有限公司 A kind of organic electroluminescence device

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5935721A (en) * 1998-03-20 1999-08-10 Eastman Kodak Company Organic electroluminescent elements for stable electroluminescent
CN101395105A (en) * 2006-03-06 2009-03-25 Lg化学株式会社 Novel anthracene derivative and organic electronic device using the same
CN101967079A (en) * 2009-07-28 2011-02-09 靳焕改 Organic material and application thereof to organic electroluminescent devices
CN102742042A (en) * 2010-01-29 2012-10-17 住友化学株式会社 Luminescent composition and light-emitting element using said composition

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5935721A (en) * 1998-03-20 1999-08-10 Eastman Kodak Company Organic electroluminescent elements for stable electroluminescent
CN101395105A (en) * 2006-03-06 2009-03-25 Lg化学株式会社 Novel anthracene derivative and organic electronic device using the same
CN101967079A (en) * 2009-07-28 2011-02-09 靳焕改 Organic material and application thereof to organic electroluminescent devices
CN102742042A (en) * 2010-01-29 2012-10-17 住友化学株式会社 Luminescent composition and light-emitting element using said composition

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109251176A (en) * 2017-07-12 2019-01-22 北京鼎材科技有限公司 A kind of organic electroluminescence device
CN109251176B (en) * 2017-07-12 2020-11-13 北京鼎材科技有限公司 Organic electroluminescent device

Also Published As

Publication number Publication date
CN104744346B (en) 2021-03-02

Similar Documents

Publication Publication Date Title
CN103601614B (en) Tetraphenyl ethylene derivative and white organic electroluminescent apparatus containing same
Tang et al. Two novel orange cationic iridium (III) complexes with multifunctional ancillary ligands used for polymer light-emitting diodes
CN106967060A (en) Serial carbazole derivates and application
CN109761879B (en) Organic blue fluorescent material, preparation method thereof and organic electroluminescent device
CN104498025A (en) Polyphenyl benzene structured cyanogroup-containing luminescent molecule and preparation method and purpose thereof
Shen et al. Naphthyridine-based thermally activated delayed fluorescence emitters for highly efficient blue OLEDs
Ye et al. Imidazole derivatives for efficient organic light-emitting diodes
CN104447566A (en) N1 biphenyl linked phenanthroimidazole compound, preparation method and application thereof
Wang et al. Blue AIEgens bearing triphenylethylene peripheral: adjustable intramolecular conjugation and good device performance
CN110615782A (en) Organic compound and organic electroluminescent device containing the same
CN108342192A (en) A kind of double boron fluorescent materials and preparation method thereof, OLED device
CN105482813A (en) Novel fluorene bipolar fluorescent material based on anthraquinone group and application of novel fluorene bipolar fluorescent material in organic light emitting diodes
CN105481901B (en) The metal complex of feux rouges containing iridium, preparation method and the organic electroluminescence device using the complex
Zhao et al. Photo-and electro-luminescence properties of the organic bipolar molecules containing phenothiazine and phenanthoimidazole moieties
CN107337630A (en) The tetraphenylethylene electroluminescent organic material and its organic luminescent device of a kind of structure containing fluorenes ring
Ye et al. Efficient blue-emitting molecules by incorporating sulfur-containing moieties into triarylcyclopentadiene: Synthesis, crystal structures and photophysical properties
CN106008501A (en) Bipolar compound containing pyridopyrazine unit and preparation method and application of compound
CN103923637A (en) Truxene-based star-shaped symmetric organic electroluminescence material and preparation method thereof
Liu et al. A quinoxaline-based charge-transfer compound for efficient deep-red organic light emitting diodes
CN108191847A (en) It is a kind of asymmetric to the organic red fluorescent small molecule material of receptor type and its application in organic electroluminescence device
CN115850187B (en) Organic electroluminescent material based on dibenzo-xenoimidazole derivative, preparation method and application thereof
CN107698487A (en) A kind of dibenzo-carbazole class fused ring compound and its organic electroluminescence device
CN104744346A (en) Dianthracene compounds containing pyridyl at terminals and application thereof
CN103525401B (en) Spirobifluorene derivative organic electroluminescence material as well as preparation method thereof
CN102850320B (en) Compound containing dibenzothiophene sulfone and preparation method and application thereof

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
TR01 Transfer of patent right
TR01 Transfer of patent right

Effective date of registration: 20210526

Address after: No.210 Zhongshan Avenue, Yixiu District, Anqing City, Anhui Province

Patentee after: Anhui Jingkai Electronic Materials Co.,Ltd.

Address before: Room 112, No.1, Taiyuan East Road, new materials Industrial Park, Nanjing Chemical Industrial Park, Nanjing, Jiangsu 210000

Patentee before: JIANGSU HECHENG ADVANCED MATERIALS Co.,Ltd.