CN108997201A - A kind of miscellaneous anthracene compound of spiro fluorene and its organic electroluminescence device - Google Patents

A kind of miscellaneous anthracene compound of spiro fluorene and its organic electroluminescence device Download PDF

Info

Publication number
CN108997201A
CN108997201A CN201810885299.1A CN201810885299A CN108997201A CN 108997201 A CN108997201 A CN 108997201A CN 201810885299 A CN201810885299 A CN 201810885299A CN 108997201 A CN108997201 A CN 108997201A
Authority
CN
China
Prior art keywords
unsubstituted
substituted
compound
aryl
heteroaryl
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.)
Withdrawn
Application number
CN201810885299.1A
Other languages
Chinese (zh)
Inventor
张弘
蔡辉
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.)
Changchun Haipurunsi Technology Co Ltd
Original Assignee
Changchun Haipurunsi Technology 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 Changchun Haipurunsi Technology Co Ltd filed Critical Changchun Haipurunsi Technology Co Ltd
Priority to CN201810885299.1A priority Critical patent/CN108997201A/en
Publication of CN108997201A publication Critical patent/CN108997201A/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • C07D213/16—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 containing only one pyridine ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • 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
    • C07D401/02—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 two hetero rings
    • C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D401/02—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 two hetero rings
    • C07D401/10—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 two hetero rings linked by a carbon chain containing aromatic 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
    • 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
    • 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
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • 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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • 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
    • 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
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • 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
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom

Abstract

The present invention provides a kind of miscellaneous anthracene compound of spiro fluorene and its organic electroluminescence device, belongs to organic photoelectrical material technical field.The compound has structure shown in formula (I), part A in the present invention has the ability in acceptant hole, introduce bridged linkage, on the one hand it can increase compound molecular weight, the material made has the function of high glass-transition temperature and can prevent crystallization, on the other hand make this kind of compound have certain distortion on stereoeffect, improve its film forming.The other end introduces the structure of the acceptant electronics of B class in specific position, increases the transporting of carrier.Using the compound as the material of main part or hole blocking layer materials'use in luminescent layer manufactured organic electroluminescence device, show the advantage that driving voltage is low, luminous efficiency is high, be the luminous organic material of function admirable.

Description

A kind of miscellaneous anthracene compound of spiro fluorene and its organic electroluminescence device
Technical field
The present invention relates to organic photoelectrical material technical fields, and in particular to a kind of miscellaneous anthracene compound of spiro fluorene and its organic electroluminescence Luminescent device.
Background technique
With the progress of information industry, traditional display has been unable to meet the requirement of people, such as: cathode-ray tube (cathode ray tube, CRT) display volume is big, driving voltage is high；Liquid crystal display (liquid crystal Display, LCD) brightness is low, narrow viewing angle, operating temperature range are small；Plasma display (plasma display panel, PDP it) involves great expense, resolution ratio is not high, power consumption is big.
Organic electroluminescent LED (organic light-emitting diodes, OLEDs) is with organic matter for hair The novel electroluminescent device of luminescent material, as a kind of completely new display technology possess in various performances existing display technology without With the advantage of rival, it is simple by feat of its preparation process, have it is all solid state, wide from main light emission, brightness height, high-resolution, visual angle (170 degree or more), fast response time, thin, small in size, light-weight, the usable flexible base board of thickness, low-voltage direct-current drive (3- 10V), low in energy consumption, operating temperature range is wide etc. so that its application market is very extensive, such as lighting system, communication system, vehicle Load display, portable electronic device, fine definition show even military field.
Electroluminescent organic material is constantly realized in recent years to be broken through, and the progress to attract people's attention is achieved, to traditional Display material constitutes strong challenge.After flexible OLED commercialization, associated scientific research and business in the world at present Strength is all in the work for the development this respect done one's utmost.Although electroluminescent organic material research have been achieved with it is huge at Fruit, but there are also some urgent problems to be solved during commercialized by OLED.
OLED material is a kind of electroluminescent material, its structure is to be put into organic matter layer between a cathode and an anode, is had Machine nitride layer includes luminescent layer and optional auxiliary layer, and auxiliary layer includes: hole injection layer, hole transmission layer, hole blocking layer, electricity Sub- barrier layer, electron transfer layer, electron injecting layer, wherein hole blocking layer can improve the efficiency and stability of OLED device, Therefore cause the very big concern of those skilled in the art.
Summary of the invention
Spiral shell the object of the present invention is to provide a kind of miscellaneous anthracene compound of spiro fluorene and its organic electroluminescence device, in the present invention The miscellaneous anthracene compound of fluorenes can effectively receive hole, and introduce bridged linkage, increase compound molecular weight, the material tool made There is high glass-transition temperature and crystallization can be prevented；Triazine class formation is introduced beside overseas Chinese federation's structure, is increased and is carried Sub- transmittability is flowed, triplet is increased, energy gap difference becomes larger.Using the compound as the material of main part or sky in luminescent layer Cave barrier layer uses and manufactured organic electroluminescence device, shows the advantage that driving voltage is low, luminous efficiency is high, is performance Excellent luminous organic material.
Present invention firstly provides a kind of miscellaneous anthracene compounds of spiro fluorene, have structure shown in following general formula (I):
A is indicated by general formula (II):
Wherein R1、R2The independent virtue selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 One of base, heteroaryl of substituted or unsubstituted C3~C30；X it is same or different be selected from CR3Or N, wherein R3Choosing From hydrogen, substituted or unsubstituted C1-C30 alkyl, the aryl of substituted or unsubstituted C6-C30, substituted or unsubstituted C3~ One of heteroaryl of C30, and at least one is N.
L is selected from the divalent of singly-bound, the divalent aryl of substituted or unsubstituted C6-C30, substituted or unsubstituted C3~C30 One of heteroaryl.
B is indicated by general formula (III):
Wherein X1Selected from CR6R7、NR8, O or S, wherein R6、R7Selected from hydrogen, substituted or unsubstituted C1-C30 alkyl, One of the aryl of substituted or unsubstituted C6-C30, heteroaryl of substituted or unsubstituted C3~C30；Wherein R4、R5、R8 The aryl of alkyl, substituted or unsubstituted C6-C30 selected from substituted or unsubstituted C1-C30, substituted or unsubstituted C3~ One of heteroaryl of C30.
Preferably, any one of the A in general formula as follows:
Wherein R1、R2、R3Independently selected from hydrogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C15 Aryl, one of the heteroaryl of substituted or unsubstituted C3~C15.
Preferably, any one of the L in singly-bound or structure as follows:
Preferably, any one of the B in general formula as follows:
Wherein R6、R7Selected from hydrogen, the alkyl of substituted or unsubstituted C1-C15, substituted or unsubstituted C6-C15 aryl, One of the heteroaryl of substituted or unsubstituted C3~C15；Wherein R4、R5、R8Alkane selected from substituted or unsubstituted C1-C15 One of base, the aryl of substituted or unsubstituted C6-C15, heteroaryl of substituted or unsubstituted C3~C15.
Preferably, any one of the miscellaneous anthracene compound of the spiro fluorene in structure as follows:
。
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device include anode, cathode with And several organic function layers between the anode and the cathode, the organic function layer contain the spiro fluorene Miscellaneous anthracene compound any one or at least two combination.
Preferably, the organic function layer includes hair hole blocking layer, and the hole blocking layer includes appointing in claim The miscellaneous anthracene compound of spiro fluorene described in one any one or at least two combination.
Preferably, the organic function layer includes luminescent layer, and the luminescent layer includes the miscellaneous anthracene compound of spiro fluorene Any one or at least two combination.
Preferably, the miscellaneous anthracene compound of the spiro fluorene is used as material of main part in luminescent layer.
Beneficial effects of the present invention:
In order to improve the efficiency and stability of OLED device in the prior art, the problems such as service life is short, the present invention is first A kind of simple compounds is provided, which has structure shown in formula (I).The miscellaneous anthracene compound of azepine spiro fluorene in the present invention has The ability in acceptant hole introduces bridged linkage, on the one hand can increase compound molecular weight, make to obtain in specific position Material have the function of high glass-transition temperature and can prevent crystallization, on the other hand make this kind of compound in space There is certain distortion in stereochemical structure, improves its film forming.Pyridine, pyrimidine and triazines are being introduced in the other end of overseas Chinese federation's structure The structure of acceptant electronics increases the transporting of carrier.In addition, overseas Chinese federation's structure has interrupted two parts interaction, make two A electrophilic and drawing electronic section localization, and the flowing of conjugated system is controlled, so that compound has bipolarity, so that swashing The minimum that son is spread to other adjacent organic matter layers, using the compound as the hole blocking layer or main body material in luminescent layer Material uses and manufactured organic electroluminescence device, shows the advantage that driving voltage is low, luminous efficiency is high, is function admirable Luminous organic material.
Specific embodiment
For a further understanding of the present invention, the preferred embodiment of the invention is described below with reference to embodiment, still It should be appreciated that these descriptions are only further explanation the features and advantages of the present invention, rather than to the claims in the present invention Limitation.
It should be noted that unless otherwise prescribed, the meaning of scientific and technical terminology used in the present invention and those skilled in the art The meaning that member is generally understood is identical.
Alkyl of the present invention refers to alkyl made of minusing a hydrogen atom in alkane molecule, can be straight chain alkane Base, branched alkyl or naphthenic base, example may include methyl, ethyl, propyl, isopropyl, normal-butyl, isobutyl group, sec-butyl, tertiary fourth Base, amyl, isopentyl, cyclopenta, cyclohexyl etc., but not limited to this.
Aryl of the present invention refers to remove a hydrogen atom on the aromatic core carbon of aromatic hydrocarbon molecule after, be left the total of univalent perssad Claiming, can be monocyclic aryl or fused ring aryl, example may include phenyl, xenyl, naphthalene, anthryl, phenanthryl or pyrenyl etc., but It is without being limited thereto.
Heteroaryl of the present invention refers to the total of the group that one or more aromatic core carbon are substituted by hetero atom in aryl Claim, the hetero atom includes but is not limited to oxygen, sulphur, nitrogen or silicon atom, and the heteroaryl can be monocycle or condensed ring, and example can wrap Include pyridyl group, phenothiazinyl, phenoxazine base, pyrimidine radicals, benzo pyrimidine radicals, carbazyl, triazine radical, benzothiazolyl, benzo miaow Oxazolyl, acridinyl etc., but not limited to this.
Divalent aryl of the present invention refers to respectively remove a hydrogen atom on two aromatic core carbon of aromatic hydrocarbon molecule after, be left Bivalent group general name, can be valentbivalent monocyclic aryl or divalent fused ring aryl, such as can be selected from phenylene, sub- biphenyl Base, sub- terphenyl, naphthylene, anthrylene, phenanthrylene, sub- pyrenyl, fluorenylidene or sub- benzo phenanthryl etc., but not limited to this.
Divalent heteroaryl radical of the present invention refers to that one or more aromatic core carbon in divalent aryl are replaced to obtain by hetero atom Group general name, the hetero atom includes but is not limited to oxygen, sulphur or nitrogen-atoms, and the divalent heteroaryl radical can be valentbivalent monocyclic Heteroaryl or divalent fused ring heteroaryl, such as can be selected from sub-pyridyl group, sub- quinolyl, sub- carbazyl, sub- thienyl, sub- benzo Thienyl, furylidene, sub- benzofuranyl, sub- pyrimidine radicals, sub- benzo pyrimidine radicals, sub- imidazole radicals or sub- benzimidazolyl etc., But not limited to this.
In substituted alkyl of the present invention, substituted aryl, substituted heteroaryl etc., the substituent group can be independent Selected from D-atom, cyano, nitro, halogen atom, the alkyl of C1-C10, the alkoxy of C1-C10, the alkylthio group of C1-C10, C1- The aryl of C30, the aryloxy group of C1-C30, the arylthio of C1-C30, C3-C30 heteroaryl, the silylation of C1~C30, C2~ Alkylamino radical, aryl amine of C6~C30 of C10 etc., such as D-atom, cyano, nitro, halogen, methyl, ethyl, propyl, isopropyl Base, tert-butyl, methoxyl group, methyl mercapto, phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, benzo phenanthryl, base, pyrene Base, fluorenyl, 9,9- dimethyl fluorenyl, benzyl, phenoxy group, thiophenyl, hexichol amido, dimethylamino, carbazyl, 9- phenyl click Oxazolyl, furyl, thienyl, triphenyl silicon substrate, trimethyl silicon substrate, trifluoromethyl, phenothiazinyl, phenoxazine base, acridinyl, piperazine Piperidinyl, pyridyl group, pyrazinyl, triazine radical, pyrimidine radicals etc., but not limited to this.
Present invention firstly provides a kind of miscellaneous anthracene compounds of spiro fluorene, have the structural formula as shown in formula (I):
A is indicated by general formula (II):
Wherein R1、R2The independent virtue selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 One of base, heteroaryl of substituted or unsubstituted C3~C30；X it is same or different be selected from CR3Or N, wherein R3Choosing From hydrogen, substituted or unsubstituted C1-C30 alkyl, the aryl of substituted or unsubstituted C6-C30, substituted or unsubstituted C3~ One of heteroaryl of C30, and at least one is N.
L is selected from the divalent of singly-bound, the divalent aryl of substituted or unsubstituted C6-C30, substituted or unsubstituted C3~C30 One of heteroaryl；
B is indicated by general formula (III):
Wherein X1Selected from CR6R7、NR8, O or S, wherein R6、R7Selected from hydrogen, substituted or unsubstituted C1-C30 alkyl, One of the aryl of substituted or unsubstituted C6-C30, heteroaryl of substituted or unsubstituted C3~C30；Wherein R4、R5、R8 The aryl of alkyl, substituted or unsubstituted C6-C30 selected from substituted or unsubstituted C1-C30, substituted or unsubstituted C3~ One of heteroaryl of C30.
Preferably, any one of the A in general formula as follows:
Wherein R1、R2、R3Independently selected from hydrogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C15 Aryl, one of the heteroaryl of substituted or unsubstituted C3~C15.
Preferably, any one of the L in singly-bound or structure as follows:
Preferably, any one of the B in general formula as follows:
Wherein R6、R7Selected from hydrogen, the alkyl of substituted or unsubstituted C1-C15, substituted or unsubstituted C6-C15 aryl, One of the heteroaryl of substituted or unsubstituted C3~C15；Wherein R4、R5、R8Alkane selected from substituted or unsubstituted C1-C15 One of base, the aryl of substituted or unsubstituted C6-C15, heteroaryl of substituted or unsubstituted C3~C15.
Preferably, any one of the miscellaneous anthracene compound of the spiro fluorene in structure as follows:
。
It is enumerated above some specific structure types of the miscellaneous anthracene compound of spiro fluorene of the present invention, but the present invention not office It is limited to these listed chemical structures, all based on structure shown in formula (I), various substituent groups are group as defined above It should all be included.
The miscellaneous anthracene compound of spiro fluorene of the present invention, preparation method are as follows:
Dibromide containing A and the coupling of the boric acid ester compound containing L, the bromide of gained compound and B are coupled Obtain the miscellaneous anthracene compound of the spiro fluorene.
The present invention limitation not special to above-mentioned reaction be using popular response well-known to those skilled in the art Can, the preparation method is easy to operate, is readily produced.
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device is those skilled in the art Known organic electroluminescence device, organic electroluminescence device of the present invention include anode, cathode and are located at Several organic function layers between the anode and cathode include the miscellaneous anthracene compound of spiro fluorene in the organic function layer Any one or at least two combination.The organic function layer may include hole injection layer, hole transmission layer, electronic blocking At least one layer in layer, luminescent layer, hole blocking layer, electron transfer layer and electron injecting layer, the preferably described organic function layer packet Include hole blocking layer, the hole blocking layer include the miscellaneous anthracene compound of spiro fluorene any one or at least two group It closes, the preferably described organic function layer includes luminescent layer, and the luminescent layer includes any one of the miscellaneous anthracene compound of spiro fluorene Or at least two combination, the more preferable miscellaneous anthracene compound of spiro fluorene is used as material of main part in luminescent layer.
The present invention is not particularly limited the source of raw material employed in following embodiment, can for commercial product or It is prepared using preparation method well-known to those skilled in the art.
Embodiment 1:
The preparation of compound 1
The preparation of compound 1-3
Under argon atmospher, by compound 1-1 (6.53g, 15mmol), to bromo-iodobenzene (4.05g, 14.3mmol), four (triphenyls Phosphine) palladium (0.35g, 0.3mmol), toluene (43ml), aqueous sodium carbonate (2M, 21ml) be added flask in, back flow reaction 8 is small When, it being cooled to room temperature, is extracted with toluene, organic phase saturated common salt water washing is purified after organic phase is dry with column chromatography, Obtain bromide 1-3 5.69g, yield 82%.
The preparation of compound 1
By gained bromide 1-3 (9.26g, 20mmol), connection boric acid pinacol ester (6.22g, 24mmol), 1,1 '-bis- (two Phenylphosphine)-ferrocene-palladium chloride (II) dichloromethane complex (0.49g, 0.6mmol), potassium acetate (5.90g, 60mmol) It is reacted under reflux 16 hours with 79ml toluene, it is cooling, 26ml water is added, stirs 30 minutes, isolates organic phase, pass through short silicon The filtering of diatomaceous earth bed, then evaporates organic solvent, gained crude product recrystallizes in heptane/toluene；Under argon atmospher, by obtained solid 1-4 (10.22g, 15mmol), compound 1-5 (5.86g, 14.3mmol), tetrakis triphenylphosphine palladium (0.35g, 0.3mmol), first Benzene (43ml), aqueous sodium carbonate (2M, 21ml) are added in flask, back flow reaction 8 hours, are cooled to room temperature, are extracted with toluene, Organic phase saturated common salt water washing is purified with column chromatography after organic phase is dry, obtains 1 11.16g of compound, yield 78%.Mass spectrum m/z:715.26 (calculated value: 715.27).Theoretical elemental content (%) C37H22N6O:C, 87.25；H, 4.65；N, 5.87；O, 2.23 actual measurement constituent content (%): C, 87.26；H, 4.66；N, 5.86；O, it is mesh that 2.22 above-mentioned confirmations, which obtain product, Mark product 1.
Embodiment 2:
The preparation of compound 12
The preparation of compound 12
1-3 in embodiment 1 is replaced with into 12-3 as shown above, 1-5 replaces with 12-5 as shown above, obtains compound 12.Mass spectrum m/z:769.35 (calculated value: 769.36).Theoretical elemental content (%) C57H43N3: C, 88.91；H, 5.63；N, 5.46 Survey constituent content (%): C, 88.92；H, 5.62；N, it is target product 12 that 5.45 above-mentioned confirmations, which obtain product,.
Embodiment 3:
The preparation of compound 22
The preparation of compound 22
1-3 in embodiment 1 is replaced with into 22-3 as shown above, 1-5 replaces with 22-5 as shown above, obtains compound 22.Mass spectrum m/z:826.29 (calculated value: 826.28).Theoretical elemental content (%) C58H36F2N4: C, 84.24；H, 4.39；F, 4.59；N, 6.78 actual measurement constituent content (%): C, 84.25；H, 4.38；F, 4.58；N, 6.77.It is mesh that above-mentioned confirmation, which obtains product, Mark product 22.
Embodiment 4:
The preparation of compound 35
The preparation of compound 35
1-3 in embodiment 1 is replaced with into 35-3 as shown above, 1-5 replaces with 35-5 as shown above, obtains compound 35.Mass spectrum m/z:742.30 (calculated value: 742.31).Theoretical elemental content (%) C55H38N2O:C, 88.92；H, 5.16；N, 3.77；O, 2.15 actual measurement constituent content (%): C, 88.91；H, 5.15；N, 3.76；O, 2.16.It is mesh that above-mentioned confirmation, which obtains product, Mark product 35.
Embodiment 5:
The preparation of compound 46
The preparation of compound 46
1-3 in embodiment 1 is replaced with into 46-3 as shown above, 1-5 replaces with 46-5 as shown above, obtains compound 46.Mass spectrum m/z:714.25 (calculated value: 714.26).Theoretical elemental content (%) C50H30N6: C, 84.01；H, 4.23；N, 11.76 actual measurement constituent content (%): C, 84.01；H, 4.22；N, 11.77.It is target product 46 that above-mentioned confirmation, which obtains product,.
Embodiment 6:
The preparation of compound 59
The preparation of compound 59
1-3 in embodiment 1 is replaced with into 59-3 as shown above, 1-5 replaces with 59-5 as shown above, obtains compound 59.Mass spectrum m/z:741.30 (calculated value: 741.31).Theoretical elemental content (%) C56H39NO:C, 90.66；H, 5.30；N, 1.89；O, 2.16 actual measurement constituent content (%): C, 90.65；H, 5.31；N, 1.88；O, 2.15.It is mesh that above-mentioned confirmation, which obtains product, Mark product 59.
Embodiment 7:
The preparation of compound 76
The preparation of compound 76
1-3 in embodiment 1 is replaced with into 76-3 as shown above, 1-5 replaces with 76-5 as shown above, obtains compound 76.Mass spectrum m/z:712.29 (calculated value: 712.28).Theoretical elemental content (%) C54H36N2: C, 90.98；H, 5.09；N, 3.93 Survey constituent content (%): C, 90.97；H, 5.08；N, 3.92.It is target product 76 that above-mentioned confirmation, which obtains product,.
Embodiment 8:
The preparation of compound 93
The preparation of compound 93
1-3 in embodiment 1 is replaced with into 93-3 as shown above, 1-5 replaces with 93-5 as shown above, obtains compound 93.Mass spectrum m/z:663.29 (calculated value: 663.28).Theoretical elemental content (%) C51H37N:C, 92.27；H, 5.62；N, 2.11 Survey constituent content (%): C, 92.27；H, 5.62；N, 2.11.It is target product 93 that above-mentioned confirmation, which obtains product,.
Embodiment 9:
The preparation of compound 103
The preparation of compound 103
1-3 in embodiment 1 is replaced with into 103-3 as shown above, 1-5 replaces with 103-5 as shown above, obtains compound 103.Mass spectrum m/z:715.30 (calculated value: 715.31).Theoretical elemental content (%) C53H37N3: C, 88.92；H, 5.21；N, 5.87 actual measurement constituent content (%): C, 88.93；H, 5.22；N, 5.88.It is target product 103 that above-mentioned confirmation, which obtains product,.
Embodiment 10:
The preparation of compound 116
The preparation of compound 116
1-3 in embodiment 1 is replaced with into 116-3 as shown above, 1-5 replaces with 116-5 as shown above, obtains compound 116.Mass spectrum m/z:639.23 (calculated value: 639.24).Theoretical elemental content (%) C46H29N3O:C, 86.36；H, 4.57；N, 6.57；O, 2.50 actual measurement constituent content (%): C, 86.35；H, 4.56；N, 6.56；O, 2.51.It is mesh that above-mentioned confirmation, which obtains product, Mark product 116.
Embodiment 11:
The preparation of compound 130
The preparation of compound 130
1-3 in embodiment 1 is replaced with into 130-3 as shown above, 1-5 replaces with 130-5 as shown above, obtain chemical combination Object 130.Mass spectrum m/z:638.24 (calculated value: 638.25).Theoretical elemental content (%) C47H30N2O:C, 88.38；H, 4.73；N, 4.39；O, 2.50 actual measurement constituent content (%): C, 88.37；H, 4.72；N, 4.38；O, 2.51.It is mesh that above-mentioned confirmation, which obtains product, Mark product 130.
Embodiment 12:
The preparation of compound 144
The preparation of compound 144
1-3 in embodiment 1 is replaced with into 144-3 as shown above, 1-5 replaces with 144-5 as shown above, obtains compound 144.Mass spectrum m/z:688.25 (calculated value: 688.26).Theoretical elemental content (%) C51H32N2O:C, 88.93；H, 4.68；N, 4.07；O, 2.32 actual measurement constituent content (%): C, 88.92；H, 4.67；N, 4.06；O, 2.31.It is mesh that above-mentioned confirmation, which obtains product, Mark product 144.
[comparison Application Example]
Transparent anode electrode ito substrate is cleaned each 15 minutes with deionized water, acetone, EtOH Sonicate respectively, is then existed It is cleaned 2 minutes in plasma cleaning device, dry and is evacuated to 5 × 10-5Pa.Then by treated, ito substrate steams Plating.Successively vapor deposition hole injection layer HAT-CN/50nm, vapor deposition hole transmission layer NPB/30nm, vapor deposition main body CBP: doping Ir (ppy)310% mixing/30nm, then vapor deposition electron transfer layer TPBi/30nm, electron injecting layer LiF/0.5nm, cathode Al/ 200nm。
[Application Example 1-12]
To compare the CBP in Application Example change into shown compound 1 in embodiment 1-12,12,22,35,46,59, 76、93、103、116、130、144。
Table 1 is the compound of preparation of the embodiment of the present invention and the characteristics of luminescence test for comparing luminescent device prepared by substance As a result.
The characteristics of luminescence of [table 1] luminescent device is tested
[Application Example 13-24]
Hole blocking layer will be increased in the luminescent layer and electron transfer layer that compare Application Example, the compound used is real Apply the shown compound 1,12,22,35,46,59,76,93,103,116,130,144 in a 1-12.
Table 2 is the compound of preparation of the embodiment of the present invention and the characteristics of luminescence test for comparing luminescent device prepared by substance As a result.
The characteristics of luminescence of [table 2] luminescent device is tested
The above result shows that the compound of the present invention is as green light material of main part or hole barrier materials, applied to having In organic electroluminescence devices, it is luminous organic material of good performance that luminous efficiency is high.
Although the present invention has carried out special description with exemplary embodiment, but it is understood that without departing from claim Defined by the case where spirit and scope of the invention, those of ordinary skill in the art can carry out various forms and details to it On change.

Claims (9)

1. a kind of miscellaneous anthracene compound of spiro fluorene, which is characterized in that have structure shown in following general formula (I):
A is indicated by general formula (II):
Wherein R1、R2Independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, take One of generation or the heteroaryl of unsubstituted C3~C30；X it is same or different be selected from CR3Or N, wherein R3Selected from hydrogen, Substituted or unsubstituted C1-C30 alkyl, the aryl of substituted or unsubstituted C6-C30, substituted or unsubstituted C3~C30 it is miscellaneous One of aryl, and at least one is N；
L is selected from the divalent heteroaryl of singly-bound, the divalent aryl of substituted or unsubstituted C6-C30, substituted or unsubstituted C3~C30 One of base；
B is indicated by general formula (III):
(Ⅲ)
Wherein X1Selected from CR6R7、NR8, O or S, wherein R6、R7Selected from hydrogen, the alkyl of substituted or unsubstituted C1-C30, substitution Or one of the aryl of unsubstituted C6-C30, heteroaryl of substituted or unsubstituted C3~C30；Wherein R4、R5、R8It is selected from The alkyl of substituted or unsubstituted C1-C30, the aryl of substituted or unsubstituted C6-C30, substituted or unsubstituted C3~C30 One of heteroaryl.
2. the miscellaneous anthracene compound of spiro fluorene according to claim 1, which is characterized in that the A is in general formula as follows Any one:
Wherein R1、R2、R3Independently selected from hydrogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C15 virtue One of base, heteroaryl of substituted or unsubstituted C3~C15.
3. the miscellaneous anthracene compound of spiro fluorene according to claim 1, which is characterized in that the L is selected from singly-bound or as follows Any one in structure:
4. the miscellaneous anthracene compound of spiro fluorene according to claim 1, which is characterized in that the B is in general formula as follows Any one:
Wherein R6、R7Selected from hydrogen, the alkyl of substituted or unsubstituted C1-C15, the aryl of substituted or unsubstituted C6-C15, substitution Or one of heteroaryl of unsubstituted C3~C15；Wherein R4、R5、R8Alkyl selected from substituted or unsubstituted C1-C15, One of the aryl of substituted or unsubstituted C6-C15, heteroaryl of substituted or unsubstituted C3~C15.
5. the miscellaneous anthracene compound of spiro fluorene according to claim 1, it is characterised in that the miscellaneous anthracene compound of the spiro fluorene is selected from as follows Any one in shown structure:
6. a kind of organic electroluminescence device, including anode, cathode and several between the anode and the cathode A organic function layer, which is characterized in that include the miscellaneous anthracene of the described in any item spiro fluorenes of Claims 1 to 5 in the organic function layer Compound any one or at least two combination.
7. a kind of organic electroluminescence device according to claim 6, which is characterized in that the organic function layer includes hair Hole blocking layer, the hole blocking layer include any one of the miscellaneous anthracene compound of the described in any item spiro fluorenes of Claims 1 to 5 Or at least two combination.
8. a kind of organic electroluminescence device according to claim 5, which is characterized in that the organic function layer includes hair Photosphere, the luminescent layer include the miscellaneous anthracene compound of the described in any item spiro fluorenes of Claims 1 to 5 any one or at least two Combination.
9. a kind of organic electroluminescence device according to claim 7, which is characterized in that the miscellaneous anthracene compound of spiro fluorene exists It is used as material of main part in luminescent layer.
CN201810885299.1A 2018-08-06 2018-08-06 A kind of miscellaneous anthracene compound of spiro fluorene and its organic electroluminescence device Withdrawn CN108997201A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201810885299.1A CN108997201A (en) 2018-08-06 2018-08-06 A kind of miscellaneous anthracene compound of spiro fluorene and its organic electroluminescence device

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201810885299.1A CN108997201A (en) 2018-08-06 2018-08-06 A kind of miscellaneous anthracene compound of spiro fluorene and its organic electroluminescence device

Publications (1)

Publication Number Publication Date
CN108997201A true CN108997201A (en) 2018-12-14

Family

ID=64594974

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201810885299.1A Withdrawn CN108997201A (en) 2018-08-06 2018-08-06 A kind of miscellaneous anthracene compound of spiro fluorene and its organic electroluminescence device

Country Status (1)

Country Link
CN (1) CN108997201A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020231021A1 (en) * 2019-05-10 2020-11-19 주식회사 엘지화학 Organic light emitting device
WO2020231214A1 (en) * 2019-05-15 2020-11-19 주식회사 엘지화학 Organic light-emitting device
JP2022503628A (en) * 2018-12-14 2022-01-12 エルジー・ケム・リミテッド Condensation ring compound and organic light emitting device containing it
CN116969928A (en) * 2022-06-30 2023-10-31 江苏三月科技股份有限公司 Compound with nitrogen-containing heterocyclic structure and application thereof in organic electroluminescent device

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2022503628A (en) * 2018-12-14 2022-01-12 エルジー・ケム・リミテッド Condensation ring compound and organic light emitting device containing it
JP7164249B2 (en) 2018-12-14 2022-11-01 エルジー・ケム・リミテッド Condensed ring compound and organic light-emitting device containing the same
WO2020231021A1 (en) * 2019-05-10 2020-11-19 주식회사 엘지화학 Organic light emitting device
WO2020231214A1 (en) * 2019-05-15 2020-11-19 주식회사 엘지화학 Organic light-emitting device
KR20200132752A (en) * 2019-05-15 2020-11-25 주식회사 엘지화학 Organic light emitting diode
KR20210060406A (en) * 2019-05-15 2021-05-26 주식회사 엘지화학 Organic light emitting diode
CN113678275A (en) * 2019-05-15 2021-11-19 株式会社Lg化学 Organic light emitting device
KR102344341B1 (en) 2019-05-15 2021-12-28 주식회사 엘지화학 Organic light emitting diode
KR102344208B1 (en) * 2019-05-15 2021-12-28 주식회사 엘지화학 Organic light emitting diode
CN116969928A (en) * 2022-06-30 2023-10-31 江苏三月科技股份有限公司 Compound with nitrogen-containing heterocyclic structure and application thereof in organic electroluminescent device
CN116969928B (en) * 2022-06-30 2024-04-19 江苏三月科技股份有限公司 Compound with nitrogen-containing heterocyclic structure and application thereof in organic electroluminescent device

Similar Documents

Publication Publication Date Title
CN108912063A (en) One kind containing phenanthrene compound and its organic electroluminescence device
KR20100028154A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN108997201A (en) A kind of miscellaneous anthracene compound of spiro fluorene and its organic electroluminescence device
CN108440524A (en) A kind of Sanya benzene derivative and its organic electroluminescence device
CN112375071B (en) Organic light-emitting compound and preparation method and application thereof
CN108358918A (en) A kind of pyrene derivatives and its organic electroluminescence device
CN108358919A (en) A kind of phenanthrene derivative and its organic electroluminescence device
CN109456203A (en) A kind of triarylamine derivative and its organic electroluminescence device
CN111662190A (en) Organic compound containing pyrene or aza-pyrene and application thereof
CN110577488A (en) Compound with carbazole as core and application thereof in organic electroluminescent device
CN108530418A (en) A kind of and fluorene derivative and its organic electroluminescence device
CN109503427B (en) D-A type organic blue fluorescent material and preparation method and application thereof
CN108727260A (en) A kind of and fluorene derivative and its organic electroluminescence device
CN108530469A (en) A kind of and fluorene compound and its organic electroluminescence device
CN108530336A (en) A kind of and fluorene compound and its organic electroluminescence device
CN108440525A (en) A kind of derivative and its organic electroluminescence device
CN110156777A (en) A kind of pyrrolotriazine derivatives and its organic electroluminescence device
CN108774233A (en) A kind of benzazolyl compounds and its organic electroluminescence device
CN112979535A (en) Compound and application thereof
CN108774236A (en) A kind of heterocyclic compound and its organic electroluminescence device
CN114560870B (en) Sulfur-containing polycyclic aromatic compound and application thereof
CN108912064A (en) A kind of triphenylene compound and its organic electroluminescence device
CN109180559A (en) A kind of condensed ring carbazole derivates and its organic electroluminescence device
CN108997314A (en) A kind of carbazole derivates and its organic electroluminescence device
CN108727358A (en) A kind of heterocyclic compound and its organic electroluminescence device

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
WW01 Invention patent application withdrawn after publication
WW01 Invention patent application withdrawn after publication

Application publication date: 20181214