CN109503633A - Compound and organic electroluminescence device - Google Patents

Compound and organic electroluminescence device Download PDF

Info

Publication number
CN109503633A
CN109503633A CN201710826229.4A CN201710826229A CN109503633A CN 109503633 A CN109503633 A CN 109503633A CN 201710826229 A CN201710826229 A CN 201710826229A CN 109503633 A CN109503633 A CN 109503633A
Authority
CN
China
Prior art keywords
base
group
substituted
compound
unsubstituted
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.)
Pending
Application number
CN201710826229.4A
Other languages
Chinese (zh)
Inventor
范洪涛
张亚光
张向慧
任雪艳
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.)
Beijing Eternal Material Technology Co Ltd
Guan Eternal Material Technology Co Ltd
Original Assignee
Beijing Eternal Material Technology Co Ltd
Guan Eternal Material 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 Beijing Eternal Material Technology Co Ltd, Guan Eternal Material Technology Co Ltd filed Critical Beijing Eternal Material Technology Co Ltd
Priority to CN201710826229.4A priority Critical patent/CN109503633A/en
Publication of CN109503633A publication Critical patent/CN109503633A/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
    • C07F5/02—Boron compounds
    • 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
    • H10K50/00—Organic light-emitting devices
    • 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
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • 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
    • 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • 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
    • C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other 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
    • 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
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/301—Details of OLEDs

Abstract

The present invention relates to shown in a kind of general formula compound such as following formula (I):Wherein Ar is selected from C6~C30Substituted or unsubstituted aromatic hydrocarbon group, C10~C30Substituted or unsubstituted condensed-nuclei aromatics group, C4~C30Substituted or unsubstituted heterocyclic arene group, C8~C30Substituted or unsubstituted condensed hetero ring aromatic hydrocarbon group, C6~C30Substituted or unsubstituted fragrant amino group；R1To R12It is respectively and independently selected from hydrogen, C6~C20Substituted or unsubstituted aromatic hydrocarbon group, C10~C20Substituted or unsubstituted condensed-nuclei aromatics group, C4~C20Substituted or unsubstituted heterocyclic arene group, C8~C20Substituted or unsubstituted condensed hetero ring aromatic hydrocarbon group, C6~C20Substituted or unsubstituted fragrant amino group.The invention further relates to a kind of organic electroluminescence devices using the general formula compound.

Description

Compound and organic electroluminescence device
Technical field
The present invention relates to organic chemistry fileds, and in particular, to a kind of compound and application thereof and organic electroluminescence Part
Background technique
Display of organic electroluminescence (hereinafter referred to as OLED) has from main light emission, low-voltage direct-current driving, all solidstate, view The a series of advantages such as angular width, light-weight, composition and simple process, compared with liquid crystal display, display of organic electroluminescence Backlight is not needed, visual angle is big, and power is low, and up to 1000 times of liquid crystal display, manufacturing cost is but lower than response speed The liquid crystal display of same resolution ratio, therefore, organic electroluminescence device has broad application prospects.
What the generation of organic electroluminescent was leaned on is the weight of the carrier (electrons and holes) transmitted in organic electroluminescence material Group, it is well known that the electric conductivity of organic material is very poor, does not have continuity unlike inorganic semiconductor, in organic semiconductor Energy band, the transmission of carrier is commonly used jump theory and is described, i.e., under the driving of an electric field, electronics is being excited or is injected into point In the lumo energy of son, achieve the purpose that charge is transmitted via the lumo energy for jumping to another molecule.In order to make have Organic electroluminescence devices reach breakthrough in application aspect, it is necessary to overcome the difficulty of the injection of organic material charge and transmittability difference. Scientists are by the adjustment of device architecture, such as increase the number of device organic material layer, and play the part of different organic layers Different roles is drilled, such as the functional material having helps electronics to inject from cathode and hole from anode, some materials help electricity The transmission of lotus, the material played the role of, which then plays, stops electronics and hole transport, most important certainly in organic electroluminescent The luminescent material of various colors will also achieve the purpose that match with adjacent functional material, the Organic Electricity of excellent in efficiency service life length Electroluminescence device is usually the optimization collocation of device architecture and various organic materials as a result, this is just that chemists design out The functionalization material for sending out structure various provides great opportunities and challenges.
As OLED technology is in the continuous propulsion for illuminating and showing two big fields, people are for influencing OLED device performance The research of efficient organic material focuses more on, an excellent in efficiency service life long organic electroluminescence device be usually device architecture with The result of the optimization collocation of various organic materials.In the most common OLED device structure, the organic of following type is generally included Material: hole-injecting material, hole mobile material, electron transport material, and assorted luminescent material (dyestuff or doping visitor Body material) and corresponding material of main part etc..
Currently, hole mobile material and hole-injecting material are mostly aromatic multi-amine class compound, as NPB, TPD, TCTA, TNATA, copper phthalocyanine (CuPc).Although these materials play critically important effect in the development process of OLED technology, some Material is still widely used so far in laboratory and PMOLED producing line, but with display and lighting area pair The continuous promotion in OLED device photoelectric properties and service life, these materials are no longer satisfied requirement, at present using existing organic The luminescent device of material, perhaps need higher driving voltage or will lead to organic electroluminescence device luminous efficiency it is low, And device lifetime can not be satisfactory.
Summary of the invention
The object of the present invention is to provide a kind of new compound, such compound can solve existing organic light-emitting compound Object is applied to the technology for needing the luminous efficiency of organic electroluminescence device caused by higher driving voltage low when luminescent device Problem.
To achieve the goals above, the present invention provides a kind of general formula compound, which has as shown in following formula (I) Structure:
In formula (I), Ar is selected from C6~C30Substituted or unsubstituted aromatic hydrocarbon group, C10~C30It is substituted or unsubstituted Condensed-nuclei aromatics group, C4~C30Substituted or unsubstituted heterocyclic arene group, C8~C30It is substituted or unsubstituted thick miscellaneous Aromatic hydrocarbon group, C6~C30Substituted or unsubstituted fragrant amino group；
When Ar is selected from the aromatic hydrocarbon group replaced, condensed-nuclei aromatics group, heterocyclic arene group, condensed hetero ring aromatic hydrocarbon group or fragrant ammonia When group, the substituent group thereon is independently selected from halogen, cyano, nitro, or is selected from C1~C30Alkyl or cycloalkyl, alkene Base, C1~C6Alkoxy or thio alkoxy, or be independently selected from monocycle with 4~60 ring carbon atoms or fused ring aryl, Containing the hetero atom selected from N, O, S, Si and with the monocycle or fused ring aryl of 4~60 ring carbon atoms；
R1To R12It is respectively and independently selected from hydrogen, C6~C20Substituted or unsubstituted aromatic hydrocarbon group, C10~C20Substitution or not Substituted condensed-nuclei aromatics group, C4~C20Substituted or unsubstituted heterocyclic arene group, C8~C20It is substituted or unsubstituted Condensed hetero ring aromatic hydrocarbon group, C6~C20Substituted or unsubstituted fragrant amino group；
Work as R1To R12Selected from substituted aromatic hydrocarbon group, condensed-nuclei aromatics group, heterocyclic arene group, condensed hetero ring aromatic hydrocarbon group or When fragrant amino group, the substituent group thereon is independently selected from halogen, cyano, nitro, or is selected from C1~C10Alkyl or cycloalkanes Base, alkenyl, C1~C6Alkoxy or thio alkoxy, or be independently selected from monocycle or condensed ring with 4~20 ring carbon atoms Aryl, containing selected from N, O, S, Si hetero atom and with 4~20 ring carbon atoms monocycle or fused ring aryl.
Specifically, as definition above-mentioned Ar, R1To R12When being respectively and independently selected from aryl, refer to selected from certain amount ring bone Aromatics ring system of frame carbon atom, including single ring architecture substituent group such as phenyl etc. also take including being covalently attached the aromatic ring of structure For group such as xenyl, terphenyl etc..
Specifically, as definition above-mentioned Ar, R1To R12Refer to when being respectively and independently selected from condensed-nuclei aromatics group with certain amount Aromatics ring system of ring skeleton carbon atom, including condensed cyclic structure substituent group such as naphthalene, anthryl etc. also include that condensed cyclic structure replaces Building stone that group is connected with single ring architecture aryl such as benzene binaphthyl, naphthalene xenyl, biphenyl dianthranide base etc. further includes altogether The thick aromatic ring substituents of valence connection structure are rolled into a ball such as binaphthyl.
Specifically, as definition above-mentioned Ar, R1To R12Refer to packet when being respectively and independently selected from heteroaryl hydrocarbon or condensed hetero ring aromatic hydrocarbon group Containing one or more selected from B, N, O, S, P (=O), the hetero atom of Si and P and with the monocycle or fused ring aryl of ring carbon atom.
Further, in formula (I), Ar is selected from C6~C15Substituted or unsubstituted aromatic hydrocarbon group, C10~C15Substitution Or unsubstituted condensed-nuclei aromatics group, C4~C15Substituted or unsubstituted heterocyclic arene group, C8~C15Substitution or do not take Condensed hetero ring aromatic hydrocarbon group, the C in generation6~C15Substituted or unsubstituted fragrant amino group；When Ar is selected from the aryl replaced, condensed-nuclei aromatics When group, heteroaryl, condensed hetero ring aromatic hydrocarbon group or fragrant amino are rolled into a ball, the substituent group thereon is independently selected from F, cyano, or is selected from C1~C10Alkyl or cycloalkyl, alkenyl, alkoxy or thio alkoxy group, or be independently selected from 4~15 ring carbons The monocycle or fused ring aryl of atom contain the hetero atom selected from N, O, S and monocycle or condensed ring virtue with 4~15 ring carbon atoms Base
Further, when Ar is selected from aryl, condensed-nuclei aromatics group, heteroaryl, condensed hetero ring aromatic hydrocarbons or the fragrant amino replaced When group, the substituent group thereon preferably independently is selected from F, cyano, methyl, ethyl, isopropyl, alkoxy, phenyl, naphthalene, pyridine Base, pyrrole radicals.
Further, in formula (I), Ar be selected from following aryl or fused ring aryl group: phenyl, xenyl, terphenyl, Naphthalene, anthryl, phenanthryl, indenyl, fluoranthene base, 9,9- dimethyl fluorenyl, fluorenyl, indeno fluorenyl, triphenylene, pyrenyl, base, Base or aphthacene base；The phenyl replaced by furyl, thienyl, pyrrole radicals and/or pyridyl group.
Above-mentioned xenyl is preferably 2- xenyl, 3- xenyl and 4- xenyl, and above-mentioned terphenyl is preferably p- three Phenyl -4- base, p- terphenyl -3- base, p- terphenyl -2- base, m- terphenyl -4- base, m- terphenyl -3- base With m- terphenyl -2- base；Above-mentioned naphthalene is preferably 1- naphthalene and/or 2- naphthalene；Above-mentioned anthryl is preferably 1- anthryl, 2- anthracene Base or 9- anthryl；Above-mentioned pyrenyl is preferably 1- pyrenyl, 2- pyrenyl or 4- pyrenyl；Above-mentioned aphthacene base be preferably 1- aphthacene base, 2- aphthacene base or 9- aphthacene base.
Further, in formula (I), Ar be selected from following heteroaryls or thick heteroaryl groups: furyl, benzofurane base, Thienyl, tolylthiophene base, pyrrole radicals, phenylpyrrole base, pyridyl group, phenylpyridyl, pyrazinyl, quinoline, triazine radical, benzo Furyl, benzothienyl, phentriazine, benzopyrazines, isobenzofuran-base, indyl, benzoquinoline, dibenzofurans Diazole, coffee quinoline base, coffee quinoline and the thiophene that base, dibenzothiophene, dibenzopyrrole base, carbazyl and its derivative, phenyl replace At least one of oxazolyl and benzodioxole group, wherein the carbazole radical derivative can include but is not limited to At least one of 9- phenyl carbazole, 9- naphthyl carbazole benzo carbazole, dibenzo-carbazole and indolocarbazole.
Further, in formula (I), Ar be selected from following fragrant amino groups: diphenylamino, two naphthylaminos, phenyl napthyl amino, Tri- phenylamino of 4-, tri- phenylamino of 3-.
Further, in formula (I), R1To R12Independently it preferably is selected from hydrogen, C6~C15Substituted or unsubstituted aromatic hydrocarbons Group, C10~C15Substituted or unsubstituted condensed-nuclei aromatics group, C4~C15Substituted or unsubstituted heterocyclic arene group, C8 ~C15Substituted or unsubstituted condensed hetero ring aromatic hydrocarbon group, C6~C15Substituted or unsubstituted fragrant amino group；Work as R1To R10Point Be not independently selected from substituted aryl, when condensed-nuclei aromatics group, heteroaryl, condensed hetero ring aromatic hydrocarbon group or fragrant amino are rolled into a ball, it is described thereon Substituent group independent preferably F, cyano, or be selected from C1~C10Alkyl or cycloalkyl, alkenyl, alkoxy or thio alkoxy base Group, or be independently selected from monocycle with 4~15 ring carbon atoms or fused ring aryl, containing the hetero atom selected from N, O, S, Si and Monocycle or fused ring aryl with 4~15 ring carbon atoms.
Further, in formula (I), R1To R12Be respectively and independently selected from following radicals: hydrogen, phenyl, naphthalene, triphenylene, 9,9 dimethyl fluorenes, two fluorenyl of spiral shell, furyl, benzofurane base, thienyl, tolylthiophene base, pyrrole radicals, phenylpyrrole base, pyrrole Piperidinyl, phenylpyridyl, pyrazinyl, fluorenyl, indeno fluorenyl, quinoline, triazine radical, benzofuranyl, benzothienyl, benzo three Piperazine, benzopyrazines, isobenzofuran-base, indyl, benzoquinoline, dibenzofuran group, dibenzothiophene, dibenzopyrrole Diazole, coffee quinoline base, coffee quinoline benzothiazolyl and the benzodioxole group that base, carbazyl and its derivative, phenyl replace At least one of, wherein the carbazole radical derivative can include but is not limited to 9- phenyl carbazole, 9- naphthyl carbazole benzo click Dioxane between diazole, coffee quinoline base, coffee quinoline benzothiazolyl or benzo that azoles, dibenzo-carbazole and indolocarbazole, phenyl replace At least one of pentenyl, diphenylamino, two naphthylaminos, phenyl napthyl amino, tri- phenylamino of 4-, tri- phenylamino of 3-.
Further, formula (I) is preferably indicated by following formula (II -1), (II -2), (II -3) or (II -4):
In formula (II -1), (II -2), (II -3) and (II -4):
Ar is identical as the definition in general formula (I)；R2、R3、R6、R10And R11It is identical as the definition in general formula (I) and not be hydrogen.
Specifically, R2、R3、R6、R10And R11Independently it preferably is selected from C6~C15Substituted or unsubstituted aromatic hydrocarbon group, C10~C15Substituted or unsubstituted condensed-nuclei aromatics group, C4~C15Substituted or unsubstituted heterocyclic arene group, C8~C15 Substituted or unsubstituted condensed hetero ring aromatic hydrocarbon group, C6~C15Substituted or unsubstituted fragrant amino group；
Work as R2、R3、R6、R10And R11It is respectively and independently selected from substituted aryl, condensed-nuclei aromatics group, heteroaryl, condensed hetero ring virtue When hydrocarbyl group or fragrant amino are rolled into a ball, the substituent group thereon independent preferably F, cyano, or it is selected from C1~C10Alkyl or cycloalkyl, Alkenyl, alkoxy or thio alkoxy group, or be independently selected from monocycle with 4~15 ring carbon atoms or fused ring aryl, Containing the hetero atom selected from N, O, S, Si and with the monocycle or fused ring aryl of 4~15 ring carbon atoms.
Further, in formula (II -2) and (II -3), preferably R3And R10It is identical and not be hydrogen；In formula (II -4), preferably R2And R11It is identical and not be hydrogen.
The expression way of above-mentioned Ca~Cb represents the carbon atom number that the group has as a~b, unless specifically indicated, generally For the carbon atom number do not include substituent group carbon atom number.
The above-mentioned statement for chemical element includes the concept of the identical isotope of chemical property, such as the statement of " hydrogen ", It also include the concept of chemical property identical " deuterium ", " tritium ".
In a preferred embodiment of the present invention, for filming performance and processing performance aspect the considerations of, described The molecular weight of compound is between 400~1200, between preferably 450~1100.
Further, following specific structure compounds: A1~A61 can preferably be gone out in conjunction with general formula of the invention, these Compound is only representative:
The present invention also provides above-mentioned organic electroluminescent compounds to prepare the purposes in organic electroluminescence device.Have Organic electroluminescence devices generally comprise first electrode, second electrode and one layer between the first electrode and second electrode Or multilayer organic function layer usually has electron injecting layer, electron-transport as the organic layer between first electrode and second electrode The organic layers such as layer, luminescent layer, hole transmission layer, hole injection layer.The compound of the present invention may be used as but be not limited to the master that shines Body material, is also used as hole mobile material.
The present invention also provides a kind of organic electroluminescence device, which includes first electrode, second electrode and is located at One or more layers organic layer between the first electrode and second electrode includes at least one in the organic layer by general formula (I) compound indicated:
In formula (I), Ar is selected from C6~C30Substituted or unsubstituted aromatic hydrocarbon group, C10~C30It is substituted or unsubstituted Condensed-nuclei aromatics group, C4~C30Substituted or unsubstituted heterocyclic arene group, C8~C30It is substituted or unsubstituted thick miscellaneous Aromatic hydrocarbon group, C6~C30Substituted or unsubstituted fragrant amino group；
When Ar is selected from the aromatic hydrocarbon group replaced, condensed-nuclei aromatics group, heterocyclic arene group, condensed hetero ring aromatic hydrocarbon group or fragrant ammonia When group, the substituent group thereon is independently selected from halogen, cyano, nitro, or is selected from C1~C30Alkyl or cycloalkyl, alkene Base, C1~C6Alkoxy or thio alkoxy, or be independently selected from monocycle with 4~60 ring carbon atoms or fused ring aryl, Containing the hetero atom selected from N, O, S, Si and with the monocycle or fused ring aryl of 4~60 ring carbon atoms；
R1To R12It is respectively and independently selected from hydrogen, C6~C20Substituted or unsubstituted aromatic hydrocarbon group, C10~C20Substitution or not Substituted condensed-nuclei aromatics group, C4~C20Substituted or unsubstituted heterocyclic arene group, C8~C20It is substituted or unsubstituted Condensed hetero ring aromatic hydrocarbon group, C6~C20Substituted or unsubstituted fragrant amino group；
Work as R1To R12Selected from substituted aromatic hydrocarbon group, condensed-nuclei aromatics group, heterocyclic arene group, condensed hetero ring aromatic hydrocarbon group or When fragrant amino group, the substituent group thereon is independently selected from halogen, cyano, nitro, or is selected from C1~C10Alkyl or cycloalkanes Base, alkenyl, C1~C6Alkoxy or thio alkoxy, or be independently selected from monocycle or condensed ring with 4~20 ring carbon atoms Aryl, containing selected from N, O, S, Si hetero atom and with 4~20 ring carbon atoms monocycle or fused ring aryl.
Further, the present invention provides a kind of organic electroluminescence device and includes first electrode, second electrode and be located at institute One or more layers organic layer between first electrode and second electrode is stated, includes at least one in the organic layer by following formula (II- 1), the compound that (II -2), (II -3) or (II -4) indicate:
In formula (II -1), (II -2), (II -3) and (II -4):
Ar is identical as the definition in general formula (I)；R2、R3、R6、R10And R11It is identical as the definition in general formula (I) and not be hydrogen.
Specifically, R2、R3、R6、R10And R11Independently it preferably is selected from C6~C15Substituted or unsubstituted aromatic hydrocarbon group, C10~C15Substituted or unsubstituted condensed-nuclei aromatics group, C4~C15Substituted or unsubstituted heterocyclic arene group, C8~C15 Substituted or unsubstituted condensed hetero ring aromatic hydrocarbon group, C6~C15Substituted or unsubstituted fragrant amino group；
Work as R2、R3、R6、R10And R11It is respectively and independently selected from substituted aryl, condensed-nuclei aromatics group, heteroaryl, condensed hetero ring virtue When hydrocarbyl group or fragrant amino are rolled into a ball, the substituent group thereon independent preferably F, cyano, or it is selected from C1~C10Alkyl or cycloalkyl, Alkenyl, alkoxy or thio alkoxy group, or be independently selected from monocycle with 4~15 ring carbon atoms or fused ring aryl, Containing the hetero atom selected from N, O, S, Si and with the monocycle or fused ring aryl of 4~15 ring carbon atoms.
Further, in formula (II -2) and (II -3), preferably R3And R10It is identical and not be hydrogen；In formula (II -4), preferably R2And R11It is identical and not be hydrogen.
General formula compound of the invention is with the miscellaneous boron six of two N of double N anion and boron atom formation in carbazole and carbazole Member ring is mother nucleus structure, since intramolecular tool is there are two the carbazole unit of electron rich property, is formed in conjunction with the boron atom of electron deficient Parent nucleus center, with significantly having Intramolecular electron transfer property, thus assign the entire lesser singlet S1 of molecule with The energy level difference of triplet state T1, be used as phosphorescent light body material when, guarantee have sufficiently high triplet while, keep compared with Small singlet energy level and lesser molecule energy gap, can reduce significantly and use material of the present invention as phosphorescence host The driving voltage of OLED has very great significance for reducing energy consumption tool；Additionally by the substituent group for parent compound The adjustment and modification of type, position and quantity, the HOMO and lumo energy of adjustable entire molecule and corresponding molecule The phosphorescent coloring of the carrier transmission material for arranging in pairs or groups different and different luminescent colors may be implemented in energy gap.
Specific embodiment
In order to make those skilled in the art more fully understand the present invention, With reference to embodiment to the present invention make into One step is described in detail.
The compound for the synthetic method that do not mention in the present invention is all the raw produce being obtained through commercial channels.Implement Various chemicals such as petroleum ether, ethyl acetate, n-hexane, toluene, tetrahydrofuran, methylene chloride, four chlorinations used in example Bis- (bromomethyl) benzene of carbon, acetone, 1,2-, CuI, o-phthaloyl chloride, phenylhydrazine hydrochloride, trifluoroacetic acid, acetic acid, trans--diamino Hexamethylene, iodobenzene, cesium carbonate, potassium phosphate, ethylenediamine, benzophenone, cyclopentanone, 9-Fluorenone, sodium tert-butoxide, Loprazolam, 1- Bromo- 2- methyl naphthalene, o-dibromobenzene, butyl lithium, Bromofume, o-dibromobenzene, benzoyl peroxide, 1- (2- bromophenyl) -2- first Base naphthalene, N- bromo-succinimide, methoxyl methyl San Jia Ji phosphonium chloride, tris(dibenzylideneacetone) dipalladium, four (triphenylphosphines) Palladium, 1,3- pairs of 2-phenyl-phosphine oxide nickel chloride, carbazole, 3,6- di-t-butyl carbazole, N- phenyl carbazole -3- bromine, 2- bromine Fluorenone, The basic chemical industries raw materials such as 2- (4- bromobenzene) -4,6- diphenyl triazine chemical products can be commercially available at home.
The analysis detection of intermediate and compound in the present invention uses ABSCIEX mass spectrograph (4000QTRAP) He Bulu Gram Nuclear Magnetic Resonance (400M).
The synthetic example of compound:
Representative synthesis path:
The synthesis of main intermediate
The synthesis of main intermediate:
Synthetic example 1:
Dinaphthyl ketone (16.6g, 0.1mol) is added in 1000ml four-hole bottle, hydrazinobenzene hydrochloride salt (31.8g, 0.22mol), ethyl alcohol (500ml), stirring and dissolving, nitrogen replace 3 times, the concentrated sulfuric acid (1.5g, 0.015mol) are put in constant pressure funnel, and 5min is left The right side is added drop-wise in reaction solution, and reaction solution increases the temperature to 65 DEG C, reacts 4h.It is cooled to room temperature, there is the crystal of puce in system It is precipitated, filtering, with twice of filter cake of 500ml ethanol rinse.It is dried under reduced pressure to obtain the puce solid product total 28g of M1, yield 80.8%.
Obtained puce solid M1 (28g, 0.081mol) is put in 1000ml four-hole bottle, is added acetic acid (280g), Trifluoroacetic acid (28g), opens stirring, and mixture is warming up to 100 DEG C, stirs 15h at such a temperature.Mixture is cooled to room temperature, There are a large amount of yellow crystals to be precipitated, filtering, filter cake is rinsed one time with 60ml acetic acid, is rinsed one time with 60ml n-hexane, and decompression is dry It is dry to obtain the total 13.5g of white powder M2, yield 54.4%.
M2 (13.5g, 0.044mol) is added in 500ml four-hole bottle, bromine is added dropwise in DMF (135ml), stirring and dissolving at room temperature DMF (30ml) solution of plain (7.04g, 0.044mol), the temperature of whole process control reaction react 5h, instead at 20 DEG C or so It should complete, stop reaction.Reaction solution is slowly poured into 800ml deionized water, there is white solid precipitation, it is small slowly to stir half When, filtering, filter cake is washed with water twice.Ethanol washing one time, re crystallization from toluene obtains the total 9.8g of white solid powder M3, purity 99%, yield 58.0%.
M3 nuclear magnetic data:1H NMR (500MHz, Chloroform) δ 9.06 (s, 1H), 8.76 (s, 1H), 8.18 (d, J= 10.0Hz, 3H), 7.63 (s, 1H), 7.40 (s, 2H), 7.19 (d, J=10.0Hz, 4H), 7.08 (s, 1H)
M3 Elemental analysis data: C, 68.59；H,3.40；Br,20.74；N,7.27
Synthetic example 2:
Dinaphthyl ketone (16.6g, 0.1mol) is added in 1000ml four-hole bottle, para-bromophenyl-hydrazine hydrochloride (49.2g, 0.22mol), Ethyl alcohol (500ml), stirring and dissolving, nitrogen replace 3 times, the concentrated sulfuric acid (1.5g, 0.015mol) are put in constant pressure funnel, 5min or so is added drop-wise in reaction solution, and reaction solution increases the temperature to 65 DEG C, reacts 4h.It is cooled to room temperature, has puce in system Crystal be precipitated, filtering, with twice of filter cake of 500ml ethanol rinse.It is dried under reduced pressure to obtain the puce solid product total 41g of M4, receive Rate 81.3%.
Obtained puce solid M4 (41g, 0.081mol) is put in 1000ml four-hole bottle, is added acetic acid (410g), Trifluoroacetic acid (41g), opens stirring, and mixture is warming up to 100 DEG C, stirs 15h at such a temperature.Mixture is cooled to room temperature, There are a large amount of yellow crystals to be precipitated, filtering, filter cake is rinsed one time with 60ml acetic acid, is rinsed one time with 60ml n-hexane, and decompression is dry It is dry to obtain the total 23.5g of white powder M5, yield 62.3%.
M5 nuclear magnetic data:1H NMR(500MHz,Chloroform)δ8.87(s,2H),8.05(s,2H),7.63(s, 2H),7.42(s,2H),7.29(s,2H),7.08(s,2H).
M5 Elemental analysis data: C, 56.93；H,2.61；Br,34.43；N,6.04
Synthetic example 3:
M5 (23.5g, 0.051mol) is added in 500ml four-hole bottle, bromine is added dropwise in DMF (200ml), stirring and dissolving at room temperature DMF (30ml) solution of plain (8.1g, 0.051mol), the temperature of whole process control reaction react 5h, reaction at 20 DEG C or so It completes, stops reaction.Reaction solution is slowly poured into 800ml deionized water, there is white solid precipitation, it is small slowly to stir half When, filtering, filter cake is washed with water twice.Ethanol washing one time, re crystallization from toluene obtains the total 16.5g of white solid powder M6, pure Degree 99%, yield 59.6%.
M6 nuclear magnetic data:1H NMR(500MHz,Chloroform)δ9.05(s,1H),8.75(s,1H),8.17(s, 1H),8.05(s,2H),7.63(s,1H),7.42(s,2H),7.29(s,2H),7.08(s,1H).
M6 Elemental analysis data: C, 48.66；H,2.04；Br,44.14；N,5.16
Synthetic example 4:
Synthetic method is with synthetic example 2, the difference is that raw material para-bromophenyl-hydrazine hydrochloride is replaced with bromophenyl-hydrazine hydrochloric acid Salt obtains the total 21.2g of intermediate M5, yield 45.6%.
Synthetic example 5: the synthesis of compound A1:
In 1000ml four-hole boiling flask, it is added intermediate M3 (38.5g, 0.1mol), dibenzofurans -2- boric acid (23.3g, 0.11mol), toluene (500ml), ethyl alcohol (100ml), water (100ml), potassium carbonate (30.4g, 0.22mol), four or three Phenylphosphine palladium (1.16g), nitrogen are replaced three times, nitrogen protection, return stirring 6h.
Stop reaction, ethyl acetate be added in reaction solution and moisture liquid, water phase are washed one time with ethyl acetate (300ml), Merge organic phase to be washed one time with deionized water (300ml), organic phase anhydrous sodium sulfate dries, filters.Filtrate receives dry, dichloromethane Alkane dissolution, is purified with silica gel column chromatography method.Eluent is ethyl acetate: petroleum ether=1:10, and it is solid to obtain white powder Body 35.3g, yield 74.7%.
By obtained A1-1 (35.3g, 0.0747mol), 2,4,6- trimethylbenzene boric acid (13.5g, 0.0822mol), first Base sulfonic acid (1g), toluene (400ml) are added in 1000ml four-hole bottle, are warming up to back flow reaction, utilize water segregator in reaction process A point water is carried out, 5h is reacted, is not having moisture to come out stopping reaction.
Solvent is removed under reduced pressure in reaction solution, is isolated and purified using silica gel column chromatography, eluent is ethyl acetate: stone Oily ether=1:10, obtains class color powder solid 40.1g, yield 89.3%, and two steps add up to total recovery to be 66.7%.
A1 nuclear magnetic data:1H NMR(500MHz,Chloroform)δ8.55(s,2H),8.30(s,1H),8.06(s, 1H), 7.98 (s, 1H), 7.66 (d, J=30.0Hz, 3H), 7.53 (d, J=10.0Hz, 3H), 7.35 (d, J=40.0Hz, 2H),7.23–7.05(m,5H),2.34(s,6H),2.27(s,3H).
A1 Elemental analysis data: C, 86.00；H,4.87；B,1.80；N,4.66；
Synthetic example 6: the synthesis of compound A2:
Compound A2 is identical as the synthetic method of A1, and difference is to replace the dibenzofurans -2- boric acid in compound A1 It is changed to the A2-1 of equivalent, obtains off-white powder solid 41.5g, yield 62.3%.
Synthetic example 7: the synthesis of compound A-13:
Compound A-13 is identical as the synthetic method of A1, and difference is to replace the dibenzofurans -2- boric acid in compound A1 It is changed to the 1- pyrene boric acid of equivalent, obtains off-white powder solid 40.5g, yield 63.8%.
Synthetic example 8: the synthesis of compound A4:
Compound A4 is identical as the synthetic method of A1, and difference is to replace the dibenzofurans -2- boric acid in compound A1 It is changed to 3, the 5- diphenyl benzene boric acid of equivalent, obtains off-white powder solid 39.5g, yield 59.6%.
Synthetic example 9: the synthesis of compound A-45:
Compound A-45 is identical as the synthetic method of A1, and difference is to replace the dibenzofurans -2- boric acid in compound A1 It is changed to 9,9- spiral shell, the two fluorenes -2- boric acid of equivalent, obtains off-white powder solid 44.5g, yield 59.4%.
Synthetic example 10: the synthesis of compound A6:
Compound A6 is identical as the synthetic method of A1, and difference is to replace the dibenzofurans -2- boric acid in compound A1 It is changed to the 1- isoquinolin boric acid of equivalent, 2,4,6- trimethylbenzene boric acid are replaced with to 2, the 6- dimethyl -4- phenyl of equivalent Phenyl boric acid obtains off-white powder solid 40.8g, yield 65.4%.
Synthetic example 11: the synthesis of compound A7:
Compound A7 is identical as the synthetic method of A1, and difference is to replace the dibenzofurans -2- boric acid in compound A1 It is changed to the 9- fluoranthene boronic acid of equivalent, 2,4,6- trimethylbenzene boric acid are replaced with to the 2- methyl 4-phenyl phenyl boric acid of equivalent, Obtain off-white powder solid 41.8g, yield 61.2%.
Synthetic example 12: the synthesis of compound A-28:
Compound A-28 is identical as the synthetic method of A1, and difference is to replace the dibenzofurans -2- boric acid in compound A1 It is changed to the N- phenyl -3- carbazole boric acid of equivalent, 2,4,6- trimethylbenzene boric acid are replaced with to the 2- methyl 4-phenyl of equivalent Phenyl boric acid obtains off-white powder solid 43.8g, yield 60.5%.
Synthetic example 13: the synthesis of compound A9:
Compound A9 is identical as the synthetic method of A1, and difference is to replace the dibenzofurans -2- boric acid in compound A1 It is changed to 4- (9H- carbazole -9- base) phenyl boric acid of equivalent, 2,4,6- trimethylbenzene boric acid are replaced with to the 2- methyl-of equivalent 4- phenyl phenyl boric acid obtains off-white powder solid 43.5g, yield 60.1%.
Synthetic example 14: the synthesis of compound A10:
Compound A10 is identical as the synthetic method of A1, and difference is to replace the dibenzofurans -2- boric acid in compound A1 It is changed to the A10-1 of equivalent, 2,4,6- trimethylbenzene boric acid are replaced with to 3, the 5- diphenyl benzene boric acid of equivalent, it is white to obtain class Color powder solid 43.7g, yield 56.7%.
Synthetic example 15: the synthesis of compound A11:
Compound A11 is identical as the synthetic method of A1, and difference is to replace the dibenzofurans -2- boric acid in compound A1 It is changed to 1, the 10- ferrosin -5- borate of equivalent, 2,4,6- trimethylbenzene boric acid are replaced with to the 1- naphthalene boronic acids of equivalent, Obtain off-white powder solid 36.7g, yield 59.1%.
Synthetic example 16: the synthesis of compound A12:
Compound A12 is identical as the synthetic method of A1, and difference is to replace the dibenzofurans -2- boric acid in compound A1 It is changed to the A12-1 of equivalent, 2,4,6- trimethylbenzene boric acid are replaced with to the 1- naphthalene boronic acids of equivalent, it is solid to obtain off-white powder Body 43.7g, yield 61.5%.
Synthetic example 17: the synthesis of compound A13:
Compound A13 is identical as the synthetic method of A1, and difference is to replace the dibenzofurans -2- boric acid in compound A1 It is changed to the A13-1 of equivalent, 2,4,6- trimethylbenzene boric acid are replaced with to the 1- naphthalene boronic acids of equivalent, it is solid to obtain off-white powder Body 40.7g, yield 61.8%.
Synthetic example 18: the synthesis of compound A14:
Compound A14 is identical as the synthetic method of A1, and 2,4,6- trimethylbenzene boric acid are replaced with to 9, the 9- bis- of equivalent Methyl fluorenes -2- boric acid, obtains off-white powder solid 38.5g, yield 57.1%.
Synthetic example 19: the synthesis of compound A15:
Compound A15 is identical as the synthetic method of A1, and difference is to replace the dibenzofurans -2- boric acid in compound A1 It is changed to 2, the 6- dimethylphenyl boronic acid of equivalent, 2,4,6- trimethylbenzene boric acid are replaced with to the 9- phenanthrene boric acid of equivalent, are obtained Off-white powder solid 34.7g, yield 58.2%.
Synthetic example 20: the synthesis of compound A16:
Compound A16 is identical as the synthetic method of A1, and difference is to replace the dibenzofurans -2- boric acid in compound A1 It is changed to the quinoline -2- boric acid of equivalent, 2,4,6- trimethylbenzene boric acid are replaced with to the 9- phenanthrene boric acid of equivalent, obtain off-white color Powder solid 40.1g, yield 64.7%.
Synthetic example 21: the synthesis of compound A17:
Compound A15 is identical as the synthetic method of A1, and difference is to replace the dibenzofurans -2- boric acid in compound A1 It is changed to the phenyl boric acid of equivalent, 2,4,6- trimethylbenzene boric acid are replaced with to the 9- phenanthrene boric acid of equivalent, obtain off-white powder Solid 34.7g, yield 61.0%.
Synthetic example 22: the synthesis of compound A18:
By intermediate M3 (33.5g, 0.1mol), 2,4,6- trimethylbenzene boric acid (18.1g, 0.11mol), methane sulfonic acid (1g), toluene (400ml) are added in 1000ml four-hole bottle, are warming up to back flow reaction, are divided in reaction process using water segregator Water reacts 5h, is not having moisture to come out stopping reaction.
Solvent is removed under reduced pressure in reaction solution, is isolated and purified using silica gel column chromatography, eluent is ethyl acetate: stone Oily ether=1:10 obtains white powder solid 42.3g, yield 82.5%.
By A8-1 (42.3g, 0.0825mol), N- phenyl -4- benzidine (24.3g, 0.099mol), Pd2 (dba) 3 (0.8g), tri-tert-butylphosphine (50% toluene solution, 1.5ml), sodium tert-butoxide (15.8g, 0.165mol) toluene (500ml) add Enter into 1000ml four-hole bottle, nitrogen protection, be warming up to back flow reaction, react 30h, stops reaction, be down to room temperature, liquid separation has Solvent is mutually removed under reduced pressure in machine, is isolated and purified using silica gel column chromatography, and eluent is ethyl acetate: petroleum ether=1:10, Obtain white powder solid 33.9g, total recovery 50.0%.
Synthetic example 23:
The synthesis of compound A19:
Compound A19 is identical as the synthetic method of A18, and difference is 2 in compound A18,4,6- trimethylbenzene boron Acid replaces with the 2- methyl 4-phenyl phenyl boric acid of equivalent, and the N- phenyl -4- benzidine in compound A18 is replaced with etc. and is worked as 1, the 1- dinaphthylamine of amount, obtains off-white powder solid 37.1g, yield 55.3%.
Synthetic example 24: the synthesis of compound A20:
Compound A20 is identical as the synthetic method of A18, and difference is 2 in compound A18,4,6- trimethylbenzene boron Acid replaces with the 2- phenyl phenyl boric acid of equivalent, and the N- phenyl -4- benzidine in compound A18 is replaced with to the N- benzene of equivalent Base-naphthalidine obtains off-white powder solid 37.1g, yield 55.3%.
Synthetic example 25: the synthesis of compound A21:
In 1000ml four-hole boiling flask, it is added intermediate M5 (46.4g, 0.1mol), 1- naphthalene boronic acids (37.8g, 0.22mol), toluene (500ml), ethyl alcohol (100ml), water (100ml), potassium carbonate (30.4g, 0.22mol), tetra-triphenylphosphine palladium (1.16g), nitrogen are replaced three times, nitrogen protection, return stirring 6h.
Stop reaction, ethyl acetate be added in reaction solution and moisture liquid, water phase are washed one time with ethyl acetate (300ml), Merge organic phase to be washed one time with deionized water (300ml), organic phase anhydrous sodium sulfate dries, filters.Filtrate receives dry, dichloromethane Alkane dissolution, is purified with silica gel column chromatography method.Eluent is ethyl acetate: petroleum ether=1:10, and it is solid to obtain white powder Body 40.2g, yield 71.9%.
By obtained A21-1 (40.2g, 0.0719mol), 2,4,6- trimethylbenzene boric acid (13.0g, 0.079mol), first Base sulfonic acid (1g), toluene (400ml) are added in 1000ml four-hole bottle, are warming up to back flow reaction, utilize water segregator in reaction process A point water is carried out, 5h is reacted, is not having moisture to come out stopping reaction.
Solvent is removed under reduced pressure in reaction solution, is isolated and purified using silica gel column chromatography, eluent is ethyl acetate: stone Oily ether=1:10, obtains class color powder solid 38.1g, yield 77.1%, and two steps add up to total recovery to be 55.4%.
A21 nuclear magnetic data:1H NMR (500MHz, Chloroform) δ 8.95 (s, 2H), 8.54 (d, J=41.5Hz, 4H), 7.88 (d, J=10.0Hz, 4H), 7.78 (d, J=5.0Hz, 4H), 7.71 (s, 2H), 7.63 (s, 2H), 7.40 (s, 2H),7.34(s,2H),7.08(s,2H),6.72(s,2H),2.34(s,6H),2.27(s,3H).
A21 Elemental analysis data: C, 89.21；H,5.14；B,1.57；N,4.08
Synthetic example 26: the synthesis of compound A22:
Compound A22 is identical as the synthetic method of A21, and difference is to replace with the 1- naphthalene boronic acids in compound A21 The 4- isopropyl benzene boronic acid of equivalent obtains off-white powder solid 37.1g, yield 55.3%.
Synthetic example 27: the synthesis of compound A23:
Compound A23 is identical as the synthetic method of A21, and difference is to replace with the 1- naphthalene boronic acids in compound A21 Fluoranthene -9- the boric acid of equivalent, obtains off-white powder solid 42.2g, yield 50.6%.
Synthetic example 28: the synthesis of compound A24:
Compound A24 is identical as the synthetic method of A21, and difference is to replace with the 1- naphthalene boronic acids in compound A24 The 4- biphenylboronic acid of equivalent obtains off-white powder solid 38.5g, yield 52.1%.
Synthetic example 29: the synthesis of compound A25:
Compound A25 is identical as the synthetic method of A21, and difference is to replace with the 1- naphthalene boronic acids in compound A21 Quinoline -4- the boric acid of equivalent, obtains off-white powder solid 37.6g, yield 54.6%.
Synthetic example 30: the synthesis of compound A26:
Compound A26 is identical as the synthetic method of A21, and difference is to replace with the 1- naphthalene boronic acids in compound A21 2,4,6- trimethylbenzene boric acid are replaced with 2, the 6- dimethyl -4- phenyl phenyl boric acid of equivalent by the pyridine -3- boric acid of equivalent, Obtain off-white powder solid 36.7g, yield 56.4%.
Synthetic example 31: the synthesis of compound A27:
Compound A27 is identical as the synthetic method of A21, and difference is to replace with the 1- naphthalene boronic acids in compound A21 2,4,6- trimethylbenzene boric acid are replaced with 2, the 6- dimethyl -4- phenyl phenyl boric acid of equivalent by the pyridine -4- boric acid of equivalent, Obtain off-white powder solid 36.1g, yield 55.5%.
Synthetic example 32: the synthesis of compound A28:
Compound A28 is identical as the synthetic method of A21, and difference is to replace with the 1- naphthalene boronic acids in compound A21 2,4,6- trimethylbenzene boric acid are replaced with 2, the 6- diphenyl benzene boric acid of equivalent, it is white to obtain class by the 3- biphenylboronic acid of equivalent Color powder solid 41.2g, yield 48.5%.
Synthetic example 33: the synthesis of compound A29:
Compound A29 is identical as the synthetic method of A21, and difference is to replace with the 1- naphthalene boronic acids in compound A21 2,4,6- trimethylbenzene boric acid are replaced with the 2- biphenylboronic acid of equivalent by the 2- naphthalene boronic acids of equivalent, and it is solid to obtain off-white powder Body 36.8g, yield 51.1%.
Synthetic example 34: the synthesis of compound A-13 0:
Compound A-13 0 is identical as the synthetic method of A21, and difference is to replace with the 1- naphthalene boronic acids in compound A21 2,4,6- trimethylbenzene boric acid, are replaced with the 2- biphenylboronic acid of equivalent, obtain off-white color by the 1- methyl 2- naphthalene boronic acids of equivalent Powder solid 35.6g, yield 49.4%.
Synthetic example 35: the synthesis of compound A-13 1:
Compound A-13 1 is identical as the synthetic method of A21, and difference is to replace with the 1- naphthalene boronic acids in compound A21 2,4,6- trimethylbenzene boric acid are replaced with the 2- methyl 4-phenyl phenyl boric acid of equivalent by 2, the 6- dimethylphenyl boronic acid of equivalent, Obtain off-white powder solid 32.1g, yield 46.5%.
Synthetic example 36: the synthesis of compound A-13 2:
Compound A-13 2 is identical as the synthetic method of A21, and difference is to replace with the 1- naphthalene boronic acids in compound A21 2,4,6- trimethylbenzene boric acid are replaced with the 2- methyl 4-phenyl phenyl boric acid of equivalent, it is white to obtain class by the 9- phenanthrene boric acid of equivalent Color powder solid 41.5g, yield 49.7%.
Synthetic example 37: the synthesis of compound A-13 3:
Compound A29 is identical as the synthetic method of A21, and difference is to replace with the 1- naphthalene boronic acids in compound A21 2,4,6- trimethylbenzene boric acid, are replaced with the 2- methyl-of equivalent by 6- (pyridine -2- base) pyridin-3-yl -3- boric acid of equivalent 4- phenyl phenyl boric acid obtains off-white powder solid 39.7g, yield 50.2%.
Synthetic example 38: the synthesis of compound A-13 4:
Compound A-13 4 is identical as the synthetic method of A21, and difference is to replace with the 1- naphthalene boronic acids in compound A21 2,4,6- trimethylbenzene boric acid, are replaced with the 2- methyl 4-phenyl benzene boron of equivalent by 4- (4- pyridyl group) phenyl boric acid of equivalent Acid obtains off-white powder solid 36.8g, yield 46.7%.
Synthetic example 39: the synthesis of compound A-13 5:
Compound A-13 5 is identical as the synthetic method of A21, and difference is to replace with the 1- naphthalene boronic acids in compound A21 2,4,6- trimethylbenzene boric acid, are replaced with the 1- naphthalene boronic acids of equivalent, obtain off-white color by the dibenzofurans -4- boric acid of equivalent Powder solid 31.2g, yield 40.3%.
Synthetic example 40: the synthesis of compound A-13 6:
Compound A-13 6 is identical as the synthetic method of A21, and difference is to replace with the 1- naphthalene boronic acids in compound A21 2,4,6- trimethylbenzene boric acid, are replaced with the 1- naphthalene boronic acids of equivalent, obtain off-white color by the dibenzothiophenes -4- boric acid of equivalent Powder solid 39.7g, yield 49.2%.
Synthetic example 41: the synthesis of compound A-13 7:
Compound A-13 7 is identical as the synthetic method of A21, and difference is to replace with the 1- naphthalene boronic acids in compound A21 2,4,6- trimethylbenzene boric acid are replaced with the 9- phenanthrene boric acid of equivalent, obtain off-white powder by the 3- methylphenylboronic acid of equivalent Solid 30.8g, yield 45.8%.
Synthetic example 42: the synthesis of compound A-13 8:
Compound A-13 8 is identical as the synthetic method of A21, and difference is to replace with the 1- naphthalene boronic acids in compound A21 2,4,6- trimethylbenzene boric acid are replaced with 2,4,6- triisopropyl phenyl boric acids of equivalent, it is white to obtain class by the phenyl boric acid of equivalent Color powder solid 35.9g, yield 53.5%.
Synthetic example 43: the synthesis of compound A-13 9:
Compound A-13 9 is identical as the synthetic method of A21, and difference is to replace with the 1- naphthalene boronic acids in compound A21 2,4,6- trimethylbenzene boric acid, are replaced with 2, the 6- diisopropyl benzene boron of equivalent by (10- phenylanthracene -9- base) boric acid of equivalent Acid obtains off-white powder solid 45.8g, yield 46.7%.
Synthetic example 44: the synthesis of compound A40:
Compound A40 is identical as the synthetic method of A21, and difference is to replace with the 1- naphthalene boronic acids in compound A21 2,4,6- trimethylbenzene boric acid are replaced with 2, the 6- diisopropyl phenyl boric acid of equivalent, obtain class by the quinoline -5- boric acid of equivalent White powder solid 39.6g, yield 54.2%.
Synthetic example 45: the synthesis of compound A41:
Compound A41 is identical as the synthetic method of A21, and difference is to replace with the 1- naphthalene boronic acids in compound A21 2,4,6- trimethylbenzene boric acid are replaced with the 3- methyl -4- pyridine boronic acid of equivalent, obtain class by the quinoline -5- boric acid of equivalent White powder solid 35.1g, yield 53.1%.
Synthetic example 46: the synthesis of compound A42:
Compound A42 is identical as the synthetic method of A21, and difference is to replace with the 1- naphthalene boronic acids in compound A21 2,4,6- trimethylbenzene boric acid are replaced with the quinoline -4- boric acid of equivalent, obtain off-white color powder by the quinoline -5- boric acid of equivalent Last solid 39.1g, yield 56.1%.
Synthetic example 47: the synthesis of compound A43:
Compound A43 is identical as the synthetic method of A21, and difference is to replace with the 1- naphthalene boronic acids in compound A21 2,4,6- trimethylbenzene boric acid are replaced with the dibenzofurans -4- boric acid of equivalent, obtain off-white color powder by the phenyl boric acid of equivalent Last solid 33.8g, yield 53.3%.
Synthetic example 48: the synthesis of compound A44:
Compound A44 is identical as the synthetic method of A21, and difference is to replace with the 1- naphthalene boronic acids in compound A21 2,4,6- trimethylbenzene boric acid are replaced with the dibenzothiophenes -4- boric acid of equivalent, obtain off-white color powder by the phenyl boric acid of equivalent Last solid 38.7g, yield 59.5%.
Synthetic example 49: the synthesis of compound A45:
Compound A45 is identical as the synthetic method of A21, and difference is to replace with the 1- naphthalene boronic acids in compound A21 2,4,6- trimethylbenzene boric acid are replaced with 2,4,6- triisopropyl phenyl boric acids of equivalent, it is white to obtain class by the phenyl boric acid of equivalent Color powder solid 43.5g, yield 51.4%.
Synthetic example 50: the synthesis of compound A46:
By intermediate M5 (46.4g, 0.1mol), 2,4,6- trimethylbenzene boric acid (18.1g, 0.11mol), methane sulfonic acid (1g), toluene (400ml) are added in 1000ml four-hole bottle, are warming up to back flow reaction, are divided in reaction process using water segregator Water reacts 5h, is not having moisture to come out stopping reaction.
Solvent is removed under reduced pressure in reaction solution, is isolated and purified using silica gel column chromatography, eluent is ethyl acetate: stone Oily ether=1:10 obtains white powder solid 52.8g, yield 89.2%.
By A46-1 (52.8g, 0.0892mol), carbazole (36.2g, 0.2165mol), Pd2 (dba) 3 (1.65g), three uncles Butyl phosphine (50% toluene solution, 3.6ml), sodium tert-butoxide (34.7g, 0.3608mol) toluene (500ml), is added to 1000ml In four-hole bottle, nitrogen protection is warming up to back flow reaction, reacts 30h, stops reaction, is down to room temperature, liquid separation, and organic phase decompression removes Remove solvent, isolated and purified using silica gel column chromatography, eluent is ethyl acetate: petroleum ether=1:10 obtains white powder Last solid 38.9g, total recovery 50.9%.
Synthetic example 51: the synthesis of compound A47:
Compound A47 is identical as compound A46 synthetic method, and difference, which is to change into the carbazole in compound A46, etc. works as The diphenylamines of amount obtains product 37.5g, yield 48.8%.
Synthetic example 52: the synthesis of compound A48:
Compound A48 is identical as compound A46 synthetic method, and difference is 2 in compound A46,4,6- trimethyls Phenyl boric acid replaces the 2- methyl 4-phenyl phenyl boric acid of flower equivalent, and carbazole changes the N- phenyl-2-naphthylamine of equivalent into, produced Product 45.5g, yield 49.6%.
Synthetic example 53: the synthesis of compound A49:
Compound A49 is identical as compound A46 synthetic method, and difference, which is to change into the carbazole in compound A46, etc. works as The naphthocarbazole of amount obtains product 39.0g, yield 45.2%.
Synthetic example 54: the synthesis of compound A-45 0:
In 1000ml four-hole boiling flask, it is added intermediate M5 (46.4g, 0.1mol), phenyl boric acid (12.2g, 0.1mol), first Benzene (500ml), ethyl alcohol (100ml), water (100ml), potassium carbonate (27.6g, 0.2mol), tetra-triphenylphosphine palladium (1.16g), nitrogen It replaces three times, nitrogen protection, return stirring 6h.
Stop reaction, ethyl acetate be added in reaction solution and moisture liquid, water phase are washed one time with ethyl acetate (300ml), Merge organic phase to be washed one time with deionized water (300ml), organic phase anhydrous sodium sulfate dries, filters.Filtrate receives dry, dichloromethane Alkane dissolution, is purified with silica gel column chromatography method.Eluent is ethyl acetate: petroleum ether=1:10, and it is solid to obtain white powder Body 32.2g, yield 69.8%.
In 1000ml four-hole boiling flask, it is added intermediate A 50-1 (32.2g, 0.07mol), 1- naphthalene boronic acids (13.8g, 0.08mol), toluene (300ml), ethyl alcohol (80ml), water (80ml), potassium carbonate (19.3g, 0.14mol), tetra-triphenylphosphine palladium (0.7g), nitrogen are replaced three times, nitrogen protection, return stirring 6h.
Stop reaction, ethyl acetate be added in reaction solution and moisture liquid, water phase are washed one time with ethyl acetate (300ml), Merge organic phase to be washed one time with deionized water (300ml), organic phase anhydrous sodium sulfate dries, filters.Filtrate receives dry, dichloromethane Alkane dissolution, is purified with silica gel column chromatography method.Eluent is ethyl acetate: petroleum ether=1:10, and it is solid to obtain white powder Body 28.4g, yield 79.8%.
By obtained A50-2 (28.4g, 0.056mol), 2,6- diphenyl benzene boric acid (16.8g, 0.062mol), methyl sulphur Sour (1g), toluene (300ml) are added in 1000ml four-hole bottle, are warming up to back flow reaction, are carried out in reaction process using water segregator Divide water, react 5h, does not there is moisture to come out stopping reaction.
Solvent is removed under reduced pressure in reaction solution, is isolated and purified using silica gel column chromatography, eluent is ethyl acetate: stone Oily ether=1:10, obtains class color powder solid 34.1g, yield 81.6%, and three steps add up to total recovery to be 45.5%.
A50 nuclear magnetic data:1H NMR(500MHz,Chloroform)δ8.95(s,1H),8.69(s,1H),8.50(d,J =1.8Hz, 2H), 7.88 (d, J=10.0Hz, 5H), 7.78 (d, J=5.0Hz, 3H), 7.70 (d, J=5.0Hz, 4H), 7.63 (s, 2H), 7.50 (d, J=10.0Hz, 6H), 7.46 (s, 3H), 7.38 (t, J=17.5Hz, 6H), 7.08 (s, 2H)
A50 Elemental analysis data: C, 90.08；H,4.72；B,1.45；N,3.75
Synthetic example 55: the synthesis of compound A-45 1:
Compound A-45 1 is identical as the synthetic method of A50, and difference is to replace with the 1- naphthalene boronic acids in compound A-45 0 2,6- diphenyl benzene boric acid is replaced with the 2- phenyl phenyl boric acid of equivalent by the 9- phenanthrene boric acid of equivalent, and it is solid to obtain off-white powder Body 34.8g, yield 48.3%.
Synthetic example 56: the synthesis of compound A-45 2:
Compound A-45 2 is identical as the synthetic method of A50, and difference is to replace with the 1- naphthalene boronic acids in compound A-45 0 Pyridine -4- the boric acid of equivalent, obtains off-white powder solid 29.6g, yield 47.6%.
Synthetic example 57: the synthesis of compound A-45 3:
Compound A-45 3 is identical as the synthetic method of A50, and difference is to replace with the 1- naphthalene boronic acids in compound A-45 0 4- (4- pyridyl group) phenyl boric acid of equivalent, obtains off-white powder solid 29.8g, yield 42.7%.
Synthetic example 58: the synthesis of compound A-45 4:
Compound A-45 4 is identical as the synthetic method of A50, and difference is to replace with the 1- naphthalene boronic acids in compound A-45 0 2,6- diphenyl benzene boric acid, is replaced with the 1- naphthalene boronic acids of equivalent, obtains off-white powder solid by the pyridine -4- boric acid of equivalent 28.2g, yield 47.4%.
Synthetic example 59: the synthesis of compound A-45 5:
Compound A-45 5 is identical as the synthetic method of A50, and difference is 2, the 6- diphenyl benzene boric acid in compound A-45 0 The 1- naphthalene boronic acids for replacing with equivalent obtain off-white powder solid 31.7g, yield 49.2%.
Synthetic example 60: the synthesis of compound A-45 6:
Compound A-45 6 is identical as the synthetic method of A50, and difference is to replace with the 1- naphthalene boronic acids in compound A-45 0 Quinoline -5- the boric acid of equivalent, obtains off-white powder solid 28.2g, yield 47.4%.
Synthetic example 61: the synthesis of compound A-45 7:
Compound A-45 7 is identical as the synthetic method of A50, and difference is to replace with the 1- naphthalene boronic acids in compound A-45 0 2,6- diphenyl benzene boric acid is replaced with the 9- phenanthrene boric acid of equivalent by the 4- methylphenylboronic acid of equivalent, and it is solid to obtain off-white powder Body 31.5g, yield 47.8%.
Synthetic example 62: the synthesis of compound A-45 8:
Compound A-45 8 is identical as the synthetic method of compound A21, and difference is to replace the intermediate M5 in compound A21 It is changed to the M8 of equivalent, 1- naphthalene boronic acids are replaced with to the phenyl boric acid of equivalent, obtains white powder solid 27.6g, yield 47.1%.
Synthetic example 63: the synthesis of compound A-45 9:
Compound A-45 9 is identical as the synthetic method of compound A21, and difference is to replace the intermediate M5 in compound A21 It is changed to the M8 of equivalent, 1- naphthalene boronic acids are replaced with to the 2- pyridine boronic acid of equivalent, 2,4,6- trimethylbenzene boric acid are replaced with The 2 of equivalent, 4,6- triisopropyl phenyl boric acids obtain white powder solid 29.6g, yield 44.0%.
Synthetic example 64: the synthesis of compound A60:
In 1000ml four-hole boiling flask, it is added intermediate M6 (54.3g, 0.1mol), phenyl boric acid (43.9g, 0.36mol), Toluene (550ml), ethyl alcohol (100ml), water (100ml), potassium carbonate (99.4g, 0.72mol), tetra-triphenylphosphine palladium (3.47g), Nitrogen is replaced three times, nitrogen protection, return stirring 6h.
Stop reaction, ethyl acetate be added in reaction solution and moisture liquid, water phase are washed one time with ethyl acetate (400ml), Merge organic phase to be washed one time with deionized water (400ml), organic phase anhydrous sodium sulfate dries, filters.Filtrate receives dry, dichloromethane Alkane dissolution, is purified with silica gel column chromatography method.Eluent is ethyl acetate: petroleum ether=1:10, and it is solid to obtain white powder Body 41.2g, yield 77.1%.
By obtained A60-1 (28.4g, 0.077mol), 2,4,6- trimethylbenzene boric acid (13.9g, 0.085mol), methyl Sulfonic acid (1g), toluene (300ml) are added in 1000ml four-hole bottle, are warming up to back flow reaction, in reaction process using water segregator into Row divides water, reacts 5h, is not having moisture to come out stopping reaction.
Solvent is removed under reduced pressure in reaction solution, is isolated and purified using silica gel column chromatography, eluent is ethyl acetate: stone Oily ether=1:10, obtains class color powder solid 42.4g, yield 83.2%, and two steps add up to total recovery to be 64.2%.
Synthetic example 65: the synthesis of compound A61:
Compound A61 is identical as the synthetic method of compound A60, and difference is the phenyl boric acid replacement in compound A60 For the 2- methylphenylboronic acid of equivalent, 2,4,6- trimethylbenzene boric acid are replaced with to the 1- naphthalene boronic acids of equivalent, obtain white powder Last solid 45.6g, yield 63.9%.
The structure of organic electroluminescence device in comparative example of the present invention are as follows:
ITO/2-TNATA(40nm)/NPB(10nm)/EML(20nm)/Bphen(50nm)/LiF(1nm)/Al。
Each functional layer material molecular structure is as follows:
Device comparative example 1:
The glass substrate that surface is coated with transparent conductive film is cleaned by ultrasonic in cleaning solution, in deionized water Ultrasonic treatment, in acetone: ultrasonic oil removing in alcohol mixed solvent (volume ratio 1: 1) mixed solution is baked under clean environment Moisture is completely removed, is performed etching with ultraviolet lamp and ozone treatment, and with low energy cation beam bombarded surface；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned Vacuum evaporation 2-TNATA is as hole injection layer on anode tunic, and evaporation rate 0.1nm/s, vapor deposition total film thickness is 40nm；So Hole transmission layer NPB, evaporation rate 0.1nm/s are deposited afterwards, vapor deposition film thickness is 10nm；
Luminescent layer of the vacuum evaporation EML as device on hole transmission layer, EML include material of main part and dyestuff material CBP as luminous layer main body is placed in the cell of vacuum phase deposition equipment by material, the method steamed altogether using multi-source, will (ppy) as dopant3Ir is placed in another room of vacuum phase deposition equipment, adjusts material of main part CBP evaporation rate For 0.1nm/s, the concentration of Ir (ppy) 3 is 10%, and vapor deposition total film thickness is 20nm；
Vacuum evaporation Bphen forms the electron transfer layer that film thickness is 50nm, evaporation rate 0.1nm/ on the light-emitting layer s；
On the electron transport layer successively vacuum evaporation with a thickness of 1nm LiF as electron injecting layer, with a thickness of 150nm's The Al layers of cathode as device.
Device embodiments 1: the compounds of this invention is as green phosphorescent material of main part
Organic electroluminescence device is prepared using method identical with device comparative example 1, difference is compound CBP replaces with compound A6.
Device embodiments 2: the compounds of this invention is as green phosphorescent material of main part
Organic electroluminescence device is prepared using method identical with device comparative example 1, difference is compound CBP replaces with compound A11.
Device embodiments 3: the compounds of this invention is as green phosphorescent material of main part
Organic electroluminescence device is prepared using method identical with device comparative example 1, difference is compound CBP replaces with compound A12.
Device embodiments 4: the compounds of this invention is as green phosphorescent material of main part
Organic electroluminescence device is prepared using method identical with device comparative example 1, difference is compound CBP replaces with compound A16.
Device embodiments 5: the compounds of this invention is as green phosphorescent material of main part
Organic electroluminescence device is prepared using method identical with device comparative example 1, difference is compound CBP replaces with compound A25.
Device embodiments 6: the compounds of this invention is as green phosphorescent material of main part
Organic electroluminescence device is prepared using method identical with device comparative example 1, difference is compound CBP replaces with compound A26.
Device embodiments 7: the compounds of this invention is as green phosphorescent material of main part
Organic electroluminescence device is prepared using method identical with device comparative example 1, difference is compound CBP replaces with compound A27.
Device embodiments 8: the compounds of this invention is as green phosphorescent material of main part
Organic electroluminescence device is prepared using method identical with device comparative example 1, difference is compound CBP replaces with compound A-13 3.
Device embodiments 9: the compounds of this invention is as green phosphorescent material of main part
Organic electroluminescence device is prepared using method identical with device comparative example 1, difference is compound CBP replaces with compound A-13 4.
Device embodiments 10: the compounds of this invention is as green phosphorescent material of main part
Organic electroluminescence device is prepared using method identical with device comparative example 1, difference is compound CBP replaces with compound A40.
Device embodiments 11: the compounds of this invention is as green phosphorescent material of main part
Organic electroluminescence device is prepared using method identical with device comparative example 1, difference is compound CBP replaces with compound A42.
Device embodiments 12: the compounds of this invention is as green phosphorescent material of main part
Organic electroluminescence device is prepared using method identical with device comparative example 1, difference is compound CBP replaces with compound A41.
Device embodiments 13: the compounds of this invention is as green phosphorescent material of main part
Organic electroluminescence device is prepared using method identical with device comparative example 1, difference is compound CBP replaces with compound A-45 2.
Device embodiments 14: the compounds of this invention is as green phosphorescent material of main part
Organic electroluminescence device is prepared using method identical with device comparative example 1, difference is compound CBP replaces with compound A-45 6.
Organic electroluminescence device performance see the table below 1:
1 device performance result of table
It is required that brightness cd/m2 Voltage V Current efficiency cd/A
Comparative example 2000.00 5.1 29
Embodiment 1 2000.00 4.4 36
Embodiment 2 2000.00 4.6 37
Embodiment 3 2000.00 4.5 38
Embodiment 4 2000.00 4.6 36
Embodiment 5 2000.00 4.5 37
Embodiment 6 2000.00 4.5 36
Embodiment 7 2000.00 4.5 40
Embodiment 8 2000.00 4.4 39
Embodiment 9 2000.00 4.5 36
Embodiment 10 2000.00 4.5 36
Embodiment 11 2000.00 4.4 37
Embodiment 12 2000.00 4.5 38
Embodiment 13 2000.00 4.6 36
Embodiment 14 2000.00 4.5 38
The above result shows that new organic materials of the invention are used for organic electroluminescence device, can effectively reduce Bright voltage improves current efficiency, is green phosphorescent material of main part of good performance.
Device embodiments 15: the compounds of this invention is as hole mobile material
Organic electroluminescence device is prepared using method identical with device comparative example 1, difference is compound NPB replaces with compound A-28.
Device embodiments 16: the compounds of this invention is as hole mobile material
Organic electroluminescence device is prepared using method identical with device comparative example 1, difference is compound NPB replaces with compound A9.
Device embodiments 17: the compounds of this invention is as hole mobile material
Organic electroluminescence device is prepared using method identical with device comparative example 1, difference is compound NPB replaces with compound A18.
Device embodiments 18: the compounds of this invention is as hole mobile material
Organic electroluminescence device is prepared using method identical with device comparative example 1, difference is compound NPB replaces with compound A19.
Device embodiments 19: the compounds of this invention is as hole mobile material
Organic electroluminescence device is prepared using method identical with device comparative example 1, difference is compound NPB replaces with compound A20.
Device embodiments 20: the compounds of this invention is as hole mobile material
Organic electroluminescence device is prepared using method identical with device comparative example 1, difference is compound NPB replaces with compound A46.
Device embodiments 21: the compounds of this invention is as hole mobile material
Organic electroluminescence device is prepared using method identical with device comparative example 1, difference is compound NPB replaces with compound A47.
Device embodiments 22: the compounds of this invention is as hole mobile material
Organic electroluminescence device is prepared using method identical with device comparative example 1, difference is compound NPB replaces with compound A48.
Device embodiments 23: the compounds of this invention is as hole mobile material
Organic electroluminescence device is prepared using method identical with device comparative example 1, difference is compound NPB replaces with compound A49.
Organic electroluminescence device performance see the table below:
2 device performance result of table
It is required that brightness cd/m2 Voltage V Current efficiency cd/A
Comparative example 2000.00 5.1 29
Embodiment 15 2000.00 4.8 35
Embodiment 16 2000.00 4.7 34
Embodiment 17 2000.00 4.6 35
Embodiment 18 2000.00 4.7 35
Embodiment 19 2000.00 4.8 36
Embodiment 20 2000.00 4.8 36
Embodiment 21 2000.00 4.7 36
Embodiment 22 2000.00 4.8 35
Embodiment 23 2000.00 4.7 36
The above result shows that new organic materials of the invention are used for organic electroluminescence device, can effectively reduce Bright voltage improves current efficiency, is hole mobile material of good performance.
The preferred embodiment of the present invention has been described above in detail, still, during present invention is not limited to the embodiments described above Detail within the scope of the technical concept of the present invention can be with various simple variants of the technical solution of the present invention are made, this A little simple variants all belong to the scope of protection of the present invention.
It is further to note that specific technical features described in the above specific embodiments, in not lance In the case where shield, can be combined in any appropriate way, in order to avoid unnecessary repetition, the present invention to it is various can No further explanation will be given for the combination of energy.
In addition, various embodiments of the present invention can be combined randomly, as long as it is without prejudice to originally The thought of invention, it should also be regarded as the disclosure of the present invention.

Claims (10)

1. shown in a kind of general formula compound such as following formula (I):
In formula (I):
Ar is selected from C6~C30Substituted or unsubstituted aromatic hydrocarbon group, C10~C30Substituted or unsubstituted condensed-nuclei aromatics base Group, C4~C30Substituted or unsubstituted heterocyclic arene group, C8~C30Substituted or unsubstituted condensed hetero ring aromatic hydrocarbon group, C6 ~C30Substituted or unsubstituted fragrant amino group；
When Ar is selected from aromatic hydrocarbon group, condensed-nuclei aromatics group, heterocyclic arene group, condensed hetero ring aromatic hydrocarbon group or the fragrant amino group replaced When, the substituent group thereon is independently selected from halogen, cyano, nitro, or is selected from C1~C30Alkyl or cycloalkyl, alkenyl, C1~C6Alkoxy or thio alkoxy, or be independently selected from monocycle or fused ring aryl with 4~60 ring carbon atoms, contain There are the hetero atom selected from N, O, S, Si and monocycle or fused ring aryl with 4~60 ring carbon atoms；
R1To R12It is respectively and independently selected from hydrogen, C6~C20Substituted or unsubstituted aromatic hydrocarbon group, C10~C20It is substituted or unsubstituted Condensed-nuclei aromatics group, C4~C20Substituted or unsubstituted heterocyclic arene group, C8~C20It is substituted or unsubstituted thick miscellaneous Aromatic hydrocarbon group, C6~C20Substituted or unsubstituted fragrant amino group；
Work as R1To R12Selected from substituted aromatic hydrocarbon group, condensed-nuclei aromatics group, heterocyclic arene group, condensed hetero ring aromatic hydrocarbon group or fragrant ammonia When group, the substituent group thereon is independently selected from halogen, cyano, nitro, or is selected from C1~C10Alkyl or cycloalkyl, alkene Base, C1~C6Alkoxy or thio alkoxy, or be independently selected from monocycle with 4~20 ring carbon atoms or fused ring aryl, Containing the hetero atom selected from N, O, S, Si and with the monocycle or fused ring aryl of 4~20 ring carbon atoms.
2. compound according to claim 1, in which:
Ar is selected from C6~C15Substituted or unsubstituted aromatic hydrocarbon group, C10~C15Substituted or unsubstituted condensed-nuclei aromatics base Group, C4~C15Substituted or unsubstituted heterocyclic arene group, C8~C15Substituted or unsubstituted condensed hetero ring aromatic hydrocarbon group, C6 ~C15Substituted or unsubstituted fragrant amino group；
When Ar is selected from the aryl replaced, condensed-nuclei aromatics group, heteroaryl, condensed hetero ring aromatic hydrocarbon group or fragrant amino are rolled into a ball, it is described its On substituent group be independently selected from F, cyano, or be selected from C1~C10Alkyl or cycloalkyl, alkenyl, alkoxy or thio alkoxy base Group, or it is independently selected from monocycle with 4~15 ring carbon atoms or fused ring aryl, containing the hetero atom and tool for being selected from N, O, S There are the monocycle or fused ring aryl of 4~15 ring carbon atoms；
R1To R12It is respectively and independently selected from hydrogen, C6~C15Substituted or unsubstituted aromatic hydrocarbon group, C10~C15Substitution or do not take Condensed-nuclei aromatics group, the C in generation4~C15Substituted or unsubstituted heterocyclic arene group, C8~C15It is substituted or unsubstituted thick Heterocyclic arene group, C6~C15Substituted or unsubstituted fragrant amino group；
Work as R1To R12It is respectively and independently selected from substituted aryl, condensed-nuclei aromatics group, heteroaryl, condensed hetero ring aromatic hydrocarbon group or fragrant amino When group, the substituent group thereon is independently selected from F, cyano, or is selected from C1~C10Alkyl or cycloalkyl, alkenyl, alkoxy or Thio alkoxy group, or be independently selected from monocycle with 4~15 ring carbon atoms or fused ring aryl, containing selected from N, O, S, The hetero atom of Si and the monocycle or fused ring aryl with 4~15 ring carbon atoms.
3. compound according to claim 1, in which:
Ar be selected from phenyl, 2- xenyl, 3- xenyl and 4- xenyl, p- terphenyl -4- base, p- terphenyl -3- base, P- terphenyl -2- base, m- terphenyl -4- base, m- terphenyl -3- base and m- terphenyl -2- base, naphthalene, anthracene Base, phenanthryl, indenyl, fluoranthene base, 9,9- dimethyl fluorenyl, fluorenyl, indeno fluorenyl, triphenylene, pyrenyl, base,Base, 1- are simultaneously Tetraphenyl, 2- aphthacene base or 9- aphthacene base aphthacene base, or selected from by furyl, thienyl, pyrrole radicals and/or pyridyl group Substituted phenyl；Or it is respectively and independently selected from furyl, benzofurane base, thienyl, tolylthiophene base, pyrrole radicals, phenylpyrrole Base, pyridyl group, pyrimidine radicals, triazine radical, phenylpyridyl, pyrazinyl, quinoline, benzofuranyl, benzothienyl, benzo three Piperazine, benzopyrazines, isobenzofuran-base, indyl, benzoquinoline, dibenzofuran group, dibenzothiophene, dibenzopyrrole Base, 9- phenyl carbazole, 9- naphthyl carbazole benzo carbazole, dibenzo-carbazole, indolocarbazole, phenyl replace diazole, coffee quinoline base, Coffee quinoline benzothiazolyl, benzodioxole group, diphenylamino, two naphthylaminos, phenyl napthyl amino, tri- phenylamino of 4-, Tri- phenylamino of 3-；
R1To R12Be respectively and independently selected from hydrogen, phenyl, xenyl, terphenyl, naphthalene, anthryl, fluoranthene base, phenanthryl, pyrenyl, Base, Qu Ji, triphenylene, 9,9 dimethyl fluorenes, two fluorenyl of spiral shell, indeno fluorenyl, furyl, benzofurane base, thienyl, phenyl Thienyl, pyrrole radicals, phenylpyrrole base, pyridyl group, pyrimidine radicals, triazine radical, phenylpyridyl, pyrazinyl, fluorenyl, indenofluorene Base, phenylpyrrole base, phenylpyridyl, quinolyl, isoquinolyl, quinazolyl, triazine radical, benzofuranyl, benzothiophene Base, benzothiazolyl, phentriazine, benzopyrazines, isobenzofuran-base, indyl, benzoquinoline, dibenzofuran group, two Diazole, the coffee quinoline base, Phen base, a word used for translation that benzothienyl, dibenzopyrrole base, carbazyl and its derivative, phenyl replace Piperidinyl, phenazinyl, phenothiazinyl, phenoxazine base, phenoxazine thiophene base, 9- phenyl carbazole, 9- naphthyl carbazole benzo carbazole, dibenzo click Diazole, coffee quinoline base, coffee quinoline benzothiazolyl or the benzodioxole group, hexichol that azoles and indolocarbazole, phenyl replace Amino, two naphthylaminos, phenyl napthyl amino, tri- phenylamino of 4-, tri- phenylamino of 3-.
4. compound according to claim 1 is indicated by following formula (II -1), (II -2), (II -3) or (II -4):
In formula (II -1), (II -2), (II -3) and (II -4):
Ar is identical as the definition in general formula (I)；R2、R3、R6、R10And R11It is identical as the definition in general formula (I) and not be hydrogen.
5. compound according to claim 4, in which:
Ar be selected from phenyl, 2- xenyl, 3- xenyl and 4- xenyl, p- terphenyl -4- base, p- terphenyl -3- base, P- terphenyl -2- base, m- terphenyl -4- base, m- terphenyl -3- base and m- terphenyl -2- base, naphthalene, anthracene Base, phenanthryl, indenyl, fluoranthene base, 9,9- dimethyl fluorenyl, fluorenyl, indeno fluorenyl, triphenylene, pyrenyl, base,Base, 1- are simultaneously Tetraphenyl, 2- aphthacene base or 9- aphthacene base aphthacene base, or selected from by furyl, thienyl, pyrrole radicals and/or pyridyl group Substituted phenyl；Or it is respectively and independently selected from furyl, benzofurane base, thienyl, tolylthiophene base, pyrrole radicals, phenylpyrrole Base, pyridyl group, pyrimidine radicals, triazine radical, phenylpyridyl, pyrazinyl, quinoline, benzofuranyl, benzothienyl, benzo three Piperazine, benzopyrazines, isobenzofuran-base, indyl, benzoquinoline, dibenzofuran group, dibenzothiophene, dibenzopyrrole Base, 9- phenyl carbazole, 9- naphthyl carbazole benzo carbazole, dibenzo-carbazole, indolocarbazole, phenyl replace diazole, coffee quinoline base, Coffee quinoline benzothiazolyl, benzodioxole group, diphenylamino, two naphthylaminos, phenyl napthyl amino, tri- phenylamino of 4-, Tri- phenylamino of 3-；
R2、R3、R6、R10And R11It is respectively and independently selected from phenyl, xenyl, terphenyl, naphthalene, anthryl, fluoranthene base, phenanthryl, pyrene Base, base, Qu Ji, triphenylene, 9,9 dimethyl fluorenes, two fluorenyl of spiral shell, indeno fluorenyl, furyl, benzofurane base, thienyl, Tolylthiophene base, pyrrole radicals, phenylpyrrole base, pyridyl group, pyrimidine radicals, triazine radical, phenylpyridyl, pyrazinyl, fluorenyl, indeno Fluorenyl, phenylpyrrole base, phenylpyridyl, quinolyl, isoquinolyl, quinazolyl, triazine radical, benzofuranyl, benzo thiophene Pheno base, benzothiazolyl, phentriazine, benzopyrazines, isobenzofuran-base, indyl, benzoquinoline, dibenzofuran group, Dibenzothiophene, dibenzopyrrole base, carbazyl and its derivative, phenyl replace diazole, coffee quinoline base, Phen base, Acridinyl, phenazinyl, phenothiazinyl, phenoxazine base, phenoxazine thiophene base, 9- phenyl carbazole, 9- naphthyl carbazole benzo carbazole, dibenzo Diazole, coffee quinoline base, coffee quinoline benzothiazolyl or the benzodioxole group, two that carbazole and indolocarbazole, phenyl replace Phenylamino, two naphthylaminos, phenyl napthyl amino, tri- phenylamino of 4-, tri- phenylamino of 3-.
6. compound according to claim 1 or 4 is selected from following concrete structure formulas:
7. application of the compound described in any one of claims 1 to 5 in organic electroluminescence device, is preferably used as hole Transmission material and/or be used as light emitting host material.
8. application of the compound as claimed in claim 6 in organic electroluminescence device, be preferably used as hole mobile material and/ Or it is used as light emitting host material.
9. a kind of organic electroluminescence device, which includes first electrode, second electrode and is located at the first electrode and the One or more layers organic layer between two electrodes, which is characterized in that include at least one in the organic layer by general formula (I) expression Compound:
In formula (I):
Ar is selected from C6~C30Substituted or unsubstituted aromatic hydrocarbon group, C10~C30Substituted or unsubstituted condensed-nuclei aromatics base Group, C4~C30Substituted or unsubstituted heterocyclic arene group, C8~C30Substituted or unsubstituted condensed hetero ring aromatic hydrocarbon group, C6 ~C30Substituted or unsubstituted fragrant amino group；
When Ar is selected from aromatic hydrocarbon group, condensed-nuclei aromatics group, heterocyclic arene group, condensed hetero ring aromatic hydrocarbon group or the fragrant amino group replaced When, the substituent group thereon is independently selected from halogen, cyano, nitro, or is selected from C1~C30Alkyl or cycloalkyl, alkenyl, C1~C6Alkoxy or thio alkoxy, or be independently selected from monocycle or fused ring aryl with 4~60 ring carbon atoms, contain There are the hetero atom selected from N, O, S, Si and monocycle or fused ring aryl with 4~60 ring carbon atoms；
R1To R12It is respectively and independently selected from hydrogen, C6~C20Substituted or unsubstituted aromatic hydrocarbon group, C10~C20It is substituted or unsubstituted Condensed-nuclei aromatics group, C4~C20Substituted or unsubstituted heterocyclic arene group, C8~C20It is substituted or unsubstituted thick miscellaneous Aromatic hydrocarbon group, C6~C20Substituted or unsubstituted fragrant amino group；
Work as R1To R12Selected from substituted aromatic hydrocarbon group, condensed-nuclei aromatics group, heterocyclic arene group, condensed hetero ring aromatic hydrocarbon group or fragrant ammonia When group, the substituent group thereon is independently selected from halogen, cyano, nitro, or is selected from C1~C10Alkyl or cycloalkyl, alkene Base, C1~C6Alkoxy or thio alkoxy, or be independently selected from monocycle with 4~20 ring carbon atoms or fused ring aryl, Containing the hetero atom selected from N, O, S, Si and with the monocycle or fused ring aryl of 4~20 ring carbon atoms.
10. a kind of organic electroluminescence device, which includes first electrode, second electrode and is located at the first electrode and the One or more layers organic layer between two electrodes, which is characterized in that include in the organic layer it is at least one by general formula (II -1), The compound that (II -2), (II -3) or (II -4) indicate:
In formula (II -1), (II -2), (II -3) and (II -4):
Ar is identical as the definition in general formula (I)；R2、R3、R6、R10And R11It is identical as the definition in general formula (I) and not be hydrogen.
CN201710826229.4A 2017-09-14 2017-09-14 Compound and organic electroluminescence device Pending CN109503633A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201710826229.4A CN109503633A (en) 2017-09-14 2017-09-14 Compound and organic electroluminescence device

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201710826229.4A CN109503633A (en) 2017-09-14 2017-09-14 Compound and organic electroluminescence device

Publications (1)

Publication Number Publication Date
CN109503633A true CN109503633A (en) 2019-03-22

Family

ID=65744343

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201710826229.4A Pending CN109503633A (en) 2017-09-14 2017-09-14 Compound and organic electroluminescence device

Country Status (1)

Country Link
CN (1) CN109503633A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109485665A (en) * 2017-09-13 2019-03-19 北京鼎材科技有限公司 Compound and application thereof and organic electroluminescence device
CN109535187A (en) * 2017-09-22 2019-03-29 北京鼎材科技有限公司 Compound and application thereof and organic electroluminescence device
CN109535188A (en) * 2017-09-22 2019-03-29 北京鼎材科技有限公司 Fused heterocyclic compound and application thereof and organic electroluminescence device

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105409020A (en) * 2012-05-15 2016-03-16 密歇根大学董事会 Dipyrrin based materials for photovoltaics, compounds capable of undergoing symmetry breaking intramolecular charge transfer in a polarizing medium and organic photovoltaic devices comprising the same
CN109485665A (en) * 2017-09-13 2019-03-19 北京鼎材科技有限公司 Compound and application thereof and organic electroluminescence device
CN109535187A (en) * 2017-09-22 2019-03-29 北京鼎材科技有限公司 Compound and application thereof and organic electroluminescence device
CN109535188A (en) * 2017-09-22 2019-03-29 北京鼎材科技有限公司 Fused heterocyclic compound and application thereof and organic electroluminescence device

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105409020A (en) * 2012-05-15 2016-03-16 密歇根大学董事会 Dipyrrin based materials for photovoltaics, compounds capable of undergoing symmetry breaking intramolecular charge transfer in a polarizing medium and organic photovoltaic devices comprising the same
CN109485665A (en) * 2017-09-13 2019-03-19 北京鼎材科技有限公司 Compound and application thereof and organic electroluminescence device
CN109535187A (en) * 2017-09-22 2019-03-29 北京鼎材科技有限公司 Compound and application thereof and organic electroluminescence device
CN109535188A (en) * 2017-09-22 2019-03-29 北京鼎材科技有限公司 Fused heterocyclic compound and application thereof and organic electroluminescence device

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
SUNG, JOOYOUNG ET AL: "S2 Fluorescence Dynamics of meso-Aryl-Substituted Subporphyrins", 《ANGEWANDTE CHEMIE, INTERNATIONAL EDITION》 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109485665A (en) * 2017-09-13 2019-03-19 北京鼎材科技有限公司 Compound and application thereof and organic electroluminescence device
CN109535187A (en) * 2017-09-22 2019-03-29 北京鼎材科技有限公司 Compound and application thereof and organic electroluminescence device
CN109535188A (en) * 2017-09-22 2019-03-29 北京鼎材科技有限公司 Fused heterocyclic compound and application thereof and organic electroluminescence device

Similar Documents

Publication Publication Date Title
CN102439111B (en) Carbazole-based phosphine oxide compound, and organic electroluminescent device including the same
CN102958906B (en) Novel organic electroluminescent compounds and use the Organnic electroluminescent device of this compound
CN109251176B (en) Organic electroluminescent device
CN104662010B (en) Aromatic amine derivative and organic electroluminescent element using same
CN106518603B (en) Organic material and organic electroluminescent module using the same
CN107833974B (en) A kind of novel electroluminescent device
CN107954942B (en) Benzopyrazines replaces anthracene derivant and organic electroluminescence device
CN109608453B (en) Compound taking 4, 7-phenanthroline as receptor and application thereof
CN109485665A (en) Compound and application thereof and organic electroluminescence device
CN108440543A (en) Perimidine derivative
CN109776542A (en) A kind of electroluminescent organic material and its application
CN111747970B (en) Containing SO2Polyheterocyclic compounds and their use
CN113929709A (en) Boron-nitrogen-containing organic compound and organic electroluminescent device comprising same
CN109535187A (en) Compound and application thereof and organic electroluminescence device
CN109503633A (en) Compound and organic electroluminescence device
CN109535188A (en) Fused heterocyclic compound and application thereof and organic electroluminescence device
CN109553620A (en) General formula compound and organic electroluminescence device
CN111423390A (en) Novel structural compound and application thereof
CN109309166B (en) Organic electroluminescent device and anthracene compound containing 2,6,9, 10-tetra-substitution
CN111377966A (en) Compound, application thereof and organic electroluminescent device comprising compound
CN108329271A (en) A kind of electroluminescent organic material and its organic luminescent device containing anthracene and benzimidazole structure
CN109400603A (en) Compound and its application in organic light emission field
CN112745321B (en) Compound containing indoloquinazolinedione structure and application thereof
CN112745322B (en) Organic material and application thereof in organic electroluminescent device
CN111675714B (en) Organic electroluminescent compound with balanced carrier transmission performance and application thereof

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
WD01 Invention patent application deemed withdrawn after publication

Application publication date: 20190322

WD01 Invention patent application deemed withdrawn after publication