CN107915732A - Naphthyridines substitutes anthracene derivant and organic electroluminescence device - Google Patents
Naphthyridines substitutes anthracene derivant and organic electroluminescence device Download PDFInfo
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- CN107915732A CN107915732A CN201711297038.XA CN201711297038A CN107915732A CN 107915732 A CN107915732 A CN 107915732A CN 201711297038 A CN201711297038 A CN 201711297038A CN 107915732 A CN107915732 A CN 107915732A
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- 0 CIc(cc1)cc2c1c([Al]*)c(cccc1)c1c2[Al]I Chemical compound CIc(cc1)cc2c1c([Al]*)c(cccc1)c1c2[Al]I 0.000 description 2
- MWIWWWKNWMUUNM-UHFFFAOYSA-N Brc1nc(nccc2)c2cc1-c1ccccc1 Chemical compound Brc1nc(nccc2)c2cc1-c1ccccc1 MWIWWWKNWMUUNM-UHFFFAOYSA-N 0.000 description 1
- QGVHVMOAPXYPKF-UHFFFAOYSA-N CC1(C)OB(C(C=C2C(c3ccccc33)=O)=CC=CC2C3=O)OC1(C)C Chemical compound CC1(C)OB(C(C=C2C(c3ccccc33)=O)=CC=CC2C3=O)OC1(C)C QGVHVMOAPXYPKF-UHFFFAOYSA-N 0.000 description 1
- LSBDFXRDZJMBSC-UHFFFAOYSA-N NC(Cc1ccccc1)=O Chemical compound NC(Cc1ccccc1)=O LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 1
- PDUINDAMJWUPTI-UHFFFAOYSA-N Nc1c(C=O)ccc(Br)n1 Chemical compound Nc1c(C=O)ccc(Br)n1 PDUINDAMJWUPTI-UHFFFAOYSA-N 0.000 description 1
- QRSYLLYRBIBENS-UHFFFAOYSA-N O=C(c1c2cccc1)c(ccc(C1=Nc3ncccc3CC1c1ccccc1)c1)c1C2=O Chemical compound O=C(c1c2cccc1)c(ccc(C1=Nc3ncccc3CC1c1ccccc1)c1)c1C2=O QRSYLLYRBIBENS-UHFFFAOYSA-N 0.000 description 1
- VTSDGYDTWADUJQ-UHFFFAOYSA-N O=C(c1ccccc1C(c1c2)=O)c1ccc2Br Chemical compound O=C(c1ccccc1C(c1c2)=O)c1ccc2Br VTSDGYDTWADUJQ-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- 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
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- 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
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- 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
Abstract
The present invention provides a kind of naphthyridines substitution anthracene derivant, has the structure shown in below formula (I)：.Wherein, L is selected from chemical bond, substituted or unsubstituted C6~C12Arlydene or sub- condensed-nuclei aromatics group, substituted or unsubstituted C3~C12Inferior heteroaryl or sub- condensed hetero ring aromatic hydrocarbon group；Ar1、Ar2It is respectively and independently selected from substituted or non-substituted C6~C30Aryl or condensed-nuclei aromatics group, substituted or non-substituted C3~C30Heteroaryl or condensed hetero ring aromatic hydrocarbon group；R1、R2、R3、R4It is respectively and independently selected from hydrogen, C1~C10Alkyl, halogen, cyano group, nitro, substituted or unsubstituted C6~C30Aryl or condensed-nuclei aromatics group, substituted or unsubstituted C3~C30Heteroaryl or condensed hetero ring aromatic hydrocarbon group.When naphthyridines substitution anthracene derivant is used for organic electroluminescent, electron mobility is higher, stability is preferable, while is beneficial to evaporation film-forming.
Description
Technical field
The present invention relates to be related to organic field of photovoltaic materials, more particularly to a kind of naphthyridines substitution anthracene derivant and organic electroluminescence
Luminescent device.
Background technology
As OLED technology is illuminating and showing the continuous propulsion in two big fields, people are for influencing OLED device performances
The research of efficient organic material focus more on.The OLED device of one excellent in efficiency long lifespan is typically that device architecture has with various
The result of the optimization collocation of machine material.In most common OLED device structure, the organic material of following species is generally included：It is empty
Hole injection material, hole mobile material, electron transport material, and assorted luminescent material (dyestuff or doping guest materials)
With corresponding material of main part etc..
The electron transport material that tradition uses in electroluminescent device is Alq3(three (8-hydroxyquinoline) aluminium), but Alq3
Electron mobility than relatively low (about in 10-6cm2/Vs).In order to improve the electronic transmission performance of electroluminescence device, people is studied
Member has done substantial amounts of pilot study work.But the problem of luminous efficiency is with the OLED device service life cannot be taken into account at present by still suffering from.
The content of the invention
A kind of electron mobility of the embodiment of the present invention offer is higher, stability is preferable, while beneficial to the electricity of evaporation film-forming
Sub- transmission material, and a kind of operating voltage of offer is low, luminous efficiency is high, the organic electroluminescence device of long lifespan.
In order to achieve the above object, present invention employs following technical scheme.
In a first aspect, the present invention provides a kind of naphthyridines to substitute anthracene derivant, there is the structure shown in below formula (I)：
Wherein, L is selected from chemical bond, substituted or unsubstituted C6~C12Arlydene or sub- condensed-nuclei aromatics group, substitution or
Unsubstituted C3~C12Inferior heteroaryl or sub- condensed hetero ring aromatic hydrocarbon group；
Ar1、Ar2It is respectively and independently selected from substituted or non-substituted C6~C30Aryl or condensed-nuclei aromatics group, substitution or non-take
The C in generation3~C30Heteroaryl or condensed hetero ring aromatic hydrocarbon group；
R1、R2、R3、R4It is respectively and independently selected from hydrogen, C1~C10Alkyl, halogen, cyano group, nitro, substituted or unsubstituted C6
~C30Aryl or condensed-nuclei aromatics group, substituted or unsubstituted C3~C30Heteroaryl or condensed hetero ring aromatic hydrocarbon group.
Second aspect, the embodiment of the present invention provide a kind of organic electroluminescence device, including electron transfer layer, the electronics
Transport layer includes at least one naphthyridines provided by the invention and substitutes anthracene derivant as electron transport material.
Naphthyridines provided by the invention substitutes anthracene derivant, and precursor structure has good coplanarity so that the derivative
With higher carrier transport, luminous efficiency ensure that, and be conducive to the film forming of molecule.2 of naphthyridines and anthracene nucleus
It is connected, the active site of parent nucleus can be protected, beneficial to the stability for keeping compound.
OLED device of the above-mentioned naphthyridines substitution anthracene derivant as electron transport layer materials is employed, is accordingly had higher
Luminous efficiency and longer service life..
Brief description of the drawings
From the detailed description to the embodiment of the present invention below in conjunction with the accompanying drawings, of the invention these and/or other side and
Advantage will become clearer and be easier to understand, wherein：
Fig. 1 is highest occupied molecular orbital HOMO (the Highest Occupied Molecular of the compounds of this invention A8
Orbital, HOMO highest occupied molecular orbital)；
Fig. 2 is lowest unoccupied molecular orbital LUMO (the Lowest Unoccupied Molecular of the compounds of this invention A8
Orbital, lowest unoccupied molecular orbital)；
Fig. 3 is the highest occupied molecular orbital HOMO of the compounds of this invention A17；
Fig. 4 is the lowest unoccupied molecular orbital LUMO of the compounds of this invention A17.
Embodiment
An embodiment of the present invention provides a kind of naphthyridines to substitute anthracene derivant, the structure with general formula (I)：
Wherein：
L is selected from chemical bond, substituted or unsubstituted C6~C12Arlydene or sub- condensed-nuclei aromatics group, substitution or unsubstituted
C3~C12Inferior heteroaryl or sub- condensed hetero ring aromatic hydrocarbon group；
Ar1、Ar2It is respectively and independently selected from substituted or non-substituted C6~C30Aryl or condensed-nuclei aromatics group, substitution or non-take
The C in generation3~C30Heteroaryl or condensed hetero ring aromatic hydrocarbon group；Ar1、Ar2It may be the same or different；
R1、R2、R3、R4It is respectively and independently selected from hydrogen, C1~C10Alkyl, halogen, cyano group, nitro, substituted or unsubstituted C6
~C30Aryl or condensed-nuclei aromatics group, substituted or unsubstituted C3~C30Heteroaryl or condensed hetero ring aromatic hydrocarbon group.
Specifically, as the above-mentioned Ar of definition1、Ar2With R3And R4When being respectively and independently selected from aryl, referring to be selected from has a fixed number
The aromatics ring system of mesh ring skeleton carbon atom, including single ring architecture substituted radical also include being covalently attached structure such as phenyl
Aromatic ring substituents group is such as xenyl, terphenyl.
R1、R2、R3And R4Hydrogen, C can be respectively and independently selected from1~C5Alkyl, halogen, cyano group, nitro, C6~C15Take
Generation or unsubstituted aryl or condensed-nuclei aromatics group, C3~C15Substituted or unsubstituted heteroaryl or condensed hetero ring aromatic hydrocarbon group.
R1、R2、R3、R4It is being respectively and independently selected from substituted aryl or condensed-nuclei aromatics group, heteroaryl or condensed hetero ring aryl
During group, substituted radical thereon can be independently selected from by halogen, cyano group, nitro, C1~C10Alkyl or cycloalkyl, C2~C10Alkene
Base, C1~C6Alkoxy or thio alkoxy group, C6~C30Mononuclear aromatics or condensed-nuclei aromatics group, containing selected from N, O,
S, the hetero atom and C of Si6~C30Mononuclear aromatics or condensed-nuclei aromatics group and Si (R5)3The group of composition.Wherein, R5Selected from C1~C6
Alkyl.Further, above-mentioned substituted radical can be independently selected from by F, cyano group, C1~C5Alkyl or cycloalkyl, Si
(CH3)3, C2~C5Alkenyl, C2~C5Alkoxy or thio alkoxy group.
Work as R1、R2、R3And R4When being respectively and independently selected from substituted or non-substituted heteroaryl or condensed hetero ring aromatic hydrocarbon group, thereon
Hetero atom can be one or more O, S and/or N.
L is selected from substituted C6~C12Arlydene or sub- condensed-nuclei aromatics group, C3~C12Inferior heteroaryl or sub- thick miscellaneous
During aromatic hydrocarbon group, substituted radical thereon can be independently selected from by halogen, cyano group, nitro, C1~C10Alkyl or cycloalkanes
Base, C2~C10Alkenyl, C1~C6Alkoxy or thio alkoxy group, C6~C30Mononuclear aromatics or condensed-nuclei aromatics base
Group, contains hetero atom and C selected from N, O, S, Si6~C30Mononuclear aromatics or condensed-nuclei aromatics group, and Si (R5)3Composition
Group.Wherein, R5Selected from C1~C6Alkyl.
Ar1、Ar2C can preferably independently be selected from6~C20Substituted or non-substituted aryl or condensed-nuclei aromatics group, C5~
C20Substituted or non-substituted heteroaryl or condensed hetero ring aromatic hydrocarbon group.
Work as Ar1、Ar2It is respectively and independently selected from substituted or non-substituted C3~C30Heteroaryl or condensed hetero ring aromatic hydrocarbon group when, its
On hetero atom can be one or more O, S and/or N.
Work as Ar1、Ar2It is respectively and independently selected from substituted aryl or condensed-nuclei aromatics group, heteroaryl or condensed hetero ring aromatic hydrocarbon group
When, substituted radical thereon is independently selected from by halogen, cyano group, nitro, C1~C10Alkyl or cycloalkyl, C2~C10Alkenyl, C1
~C6Alkoxy or thio alkoxy group, C6~C30Mononuclear aromatics or condensed-nuclei aromatics group, containing selected from N, O, S, Si
Hetero atom and C6~C30Mononuclear aromatics or condensed-nuclei aromatics group and Si (R5)3The group of composition.Wherein, the R5Selected from C1~C6's
Alkyl.Further, above-mentioned substituent can be independently selected from by F, cyano group, C1~C5Alkyl or cycloalkyl, Si (CH3)3, C2~
C5Alkenyl, C1~C5Alkoxy or thio alkoxy group, C6~C15Mononuclear aromatics or condensed-nuclei aromatics group, contain choosing
From the hetero atom and C of N or O6~C15Mononuclear aromatics or condensed-nuclei aromatics group composition group.
Ar1、Ar2When being respectively and independently selected from substituted or non-substituted aryl or fused ring aryl group, it can be respectively and independently selected from
By phenyl, xenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluoranthene base, fluorenyl, indeno fluorenyl, triphenylene, pyrene
Base, base,Base, aphthacene base, the phenyl substituted by furyl, thienyl, pyrrole radicals and/or pyridine radicals, benzene binaphthyl, 4-
Naphthylphenyl, 6- phenyl napthyls, 7- phenyl phenanthryl.Wherein, above-mentioned xenyl, which can be selected from, 2- xenyls, 3- xenyls, 4-
The group of xenyl composition；Above-mentioned terphenyl can be selected from by p- terphenyl -4- bases, p- terphenyl -3- bases, p- three
The group that xenyl -2- bases, m- terphenyl -4- bases, m- terphenyl -3- bases and m- terphenyl -2- bases form；It is above-mentioned
Naphthyl can be selected from the group being made of 1- naphthyls and 2- naphthyls；Above-mentioned anthryl can be selected from by 1- anthryls, 2- anthryls and 9- anthracenes
The group that base is formed；Above-mentioned fluorenyl is selected from the group being made of 1- fluorenyls, 2- fluorenyls, 3- fluorenyls, 4- fluorenyls and 9- fluorenyls；It is above-mentioned
Fluorenyl derivative is selected from by 9,9 '-dimethyl fluorene, and 9, the group that 9 '-spiral shell, two fluorenes and benzfluorene are formed；Above-mentioned pyrenyl is selected from by 1-
The group that pyrenyl, 2- pyrenyls and 4- pyrenyls are formed；Above-mentioned aphthacene base is selected from by 1- aphthacenes base, 2- aphthacenes base and 9- and four
The group that phenyl is formed.
Ar1、Ar2In the heteroaryl groups or condensed hetero ring aromatic hydrocarbon group being respectively and independently selected from, can be independently selected from by furans
Base, benzofurane base, thienyl, tolylthiophene base, pyrrole radicals, phenylpyrrole base, pyridine radicals, phenylpyridyl, naphthyridines base, quinoline
Quinoline, triazine radical, benzofuranyl, benzothienyl, phentriazine, benzo naphthyridines, isobenzofuran-base, indyl, benzo quinoline
Quinoline, dibenzofuran group, dibenzothiophene, dibenzopyrrole base, carbazyl and its derivative, diazole, the coffee of phenyl substitution
The group of quinoline base, coffee quinoline benzothiazolyl and benzodioxole group composition.Wherein, above-mentioned carbazole radical derivative can be selected from
The group being made of 9- phenyl carbazoles, 9- naphthyl carbazoles benzo carbazole, dibenzo-carbazole and indolocarbazole.
Further, Ar1、Ar2Phenyl, xenyl, naphthyl, phenyl, the phenyl of pyridine radicals substitution can be respectively and independently selected from
Pyridine radicals, anthryl, phenanthryl, furyl, benzofurane base, thienyl, tolylthiophene base, pyrrole radicals, phenylpyrrole base or pyridine
Base.
R1、R2、R3And R4Following radicals can be respectively and independently selected from：Methyl, ethyl, propyl group, isopropyl, the tert-butyl group, ring penta
Base, cyclohexyl, cyano group, nitro, phenyl, naphthyl, triphenylene, 9,9 dimethyl fluorenes, two fluorenyl of spiral shell, furyl, benzofurane
Base, thienyl, tolylthiophene base, pyrrole radicals, phenylpyrrole base, pyridine radicals, phenylpyridyl, naphthyridines base, fluorenyl, indenofluorene
Base, quinoline, triazine radical, benzofuranyl, benzothienyl, phentriazine, benzo naphthyridines, isobenzofuran-base, indyl, benzene
And quinoline, dibenzofuran group, dibenzothiophene, dibenzopyrrole base, carbazyl and its derivative, the two of phenyl substitution
Azoles, coffee quinoline base, coffee quinoline benzothiazolyl or benzodioxole group.Wherein, above-mentioned carbazole radical derivative can be selected from by
The group that 9- phenyl carbazoles, 9- naphthyl carbazoles benzo carbazole, dibenzo-carbazole and indolocarbazole form.
Further, R1、R2、R3And R4Methyl, ethyl, propyl group, isopropyl, the tert-butyl group, benzene can be respectively and independently selected from
Base, naphthyl, pyridine radicals, phenylpyridyl, dibenzofuran group or xenyl.
Compared with prior art, embodied in the following areas the advantages of the naphthyridines substitution anthracene derivant of general formula (I) of the present invention：
Body structure has good coplanarity so that and the derivative has higher carrier transport, so as to
Significantly reduce the operating voltage of the device using such material.2 of naphthyridines and anthracene nucleus are connected, and so design can protect mother
The active site of core, beneficial to keeping the stability of compound, while may insure Cloud Distribution on parent nucleus, LUMO distributions with
Cloud Distribution is consistent.
Precursor structure has deeper LUMO, realizes the performance of good transmission electronics, while keeps coplanar knot
Structure is conducive to the film forming of molecule；Substitute the change of ground level and electronic property, the energy of final goal compound can be finely tuned
Level and transmission performance, such compound are used as electron transport layer materials, can significantly increase the luminous efficiency of device.
In an embodiment of the present invention, the naphthyridines substitution anthracene derivant of general formula (I), its molecular weight is less than 1000.It is excellent
Elect 450~900 as.More preferably 600~800.Suitable substituted radical can be selected based on the setting of molecular weight.
The naphthyridines substitution anthracene derivant of the general formula (I) of molecular weight control in the above range, its molecular weight is sufficiently large, ensures
With higher Tg (glass transition temperature), so that with good heat endurance；Meanwhile molecular weight is again no excessive, can be beneficial to
Vacuum evaporation forms a film.
Specifically, the naphthyridines substitution anthracene derivant of general formula (I) can be selected from the compound group that following structural formula is A1-A21
Into group：
Corresponding with above-mentioned naphthyridines substitution anthracene derivant provided by the invention, the embodiment of the present invention, which additionally provides one kind, to be had
Organic electroluminescence devices, the electron transfer layer of the organic electroluminescence device include above-mentioned naphthyridines substitution anthracene derivant.
In addition, the device may also include first electrode, second electrode and between the first electrode and second electrode
One or more layers organic layer.The organic layer includes electron transfer layer, is included in electron transfer layer provided by the invention above-mentioned
At least one above-mentioned logical formula (I) shown in compound.
Organic electroluminescence device provided by the invention, its electron transport layer materials select the naphthyridines of above-mentioned logical formula (I)
Substitute anthracene derivant, can effectively reduce device operating voltages and improve device light emitting efficiency, extend device lifetime.
Further, OLED device provided in an embodiment of the present invention can have such as lower structure on substrate：
(1) anode/hole injection layer (HIL)/hole transmission layer (HTL)/luminescent layer (EML)/electron transfer layer (ETL)/
Electron injecting layer (EIL)/cathode；
(2) anode/hole transmission layer (HTL)/luminescent layer (EML)/hole blocking layer (HBL)/electron transfer layer (ETL)/
Electron injecting layer (EIL)/cathode.
Above-mentioned "/" represents to be laminated in order between difference in functionality layer.
Substrate can use tradition to have the substrate in OLED device, such as：Glass or plastics.Anode material can use saturating
Bright high conductivity material, such as indium tin oxygen (ITO), indium zinc oxygen (IZO), stannic oxide (SnO2), zinc oxide (ZnO) etc..
The OLED device of one embodiment of the invention selects glass substrate in making, and selects ITO to make anode material.
Hole-injecting material has CuPc, TNATA and PEDT：PSS etc..The present invention's has in an embodiment, hole injection layer
Using 2-TNATA.
Hole transmission layer can use N, N '-two (3- tolyls)-N, N '-diphenyl-[1,1- xenyls] -4,4 '-two
Amine (TPD) or N, N ' the tri-arylamine group material such as-diphenyl-N, N '-two (1- naphthyls)-(1,1 '-xenyl) -4,4 '-diamines (NPB)
Material.The present invention's has in an embodiment, and hole mobile material selects NPB.
OLED device structure can be that single-shot photosphere can also be multi-luminescent layer structure.Employed in one embodiment of the invention
The structure of single-shot photosphere.Luminescent layer includes light emitting host material and luminescent dye, wherein luminescent dye and light emitting host material
Mass ratio controlled by regulating and controlling both evaporation rates in device fabrication process, usually control luminescent dye and the master that shines
The evaporation rate ratio of body material is 1% to 8%, such as 1%, 2%, 3%, 3.5%, 4%, 4.5%, 5%, 6%, 7%, 8%
Deng preferably 3% to 5%.
Wherein, luminescent dye can include metal iridium complex Ir (ppy), FIrpic, and pure organic molecule, red glimmering
Alkene, DPP, DCJ, DCM etc..Light emitting host material can be including BAlq, AND, CBP, mCP, TBPe etc..
In the OLED device of the embodiment of the present invention, the thickness of luminescent layer is 5nm-50nm, for example, 5nm, 6nm, 8nm,
10nm, 12nm, 15nm, 20nm, 25nm, 28nm, 30nm, 35nm, 38nm, 40nm, 45nm, 50nm etc..Preferably 10nm-
30nm.The electron transfer layer of the present invention can be used alone a kind of electron transport material provided by the invention, can also coordinate this
The other kinds of electron transport material provided is provided or other conventional electron transport material doping of this area use.It is common
Electron transport material have Alq3, code name is material of CA, CC-1 etc. in Bphen, BCP, PBD, and following formula.In a tool
In body embodiment, use can be doped with electron transport material using the present invention and 8-hydroxyquinoline lithium.
When a kind of electron transport material of the present invention coordinates another electron transport material of the present invention or coordinates other
Conventional electron transport material doping is in use, both part by weight can be 90:10-10:90, such as 10:90、20:80、
30:70、40:60、50:50、60:40、70:30、80:20、90:10。
The thickness of electron transfer layer can be 5-100nm, for example, 5nm, 6nm, 8nm, 10nm, 12nm, 15nm, 20nm,
30nm, 35nm, 38nm, 40nm, 50nm, 60nm, 80nm, 90nm, 95nm, 100nm etc..Preferably 10-40nm.
The electron injecting layer of OLED device/cathode material selects LiF/Al.
The concrete structure of different materials in materials set forth above is seen below：
The present invention organic electroluminescence device possess excellent photoelectricity performance, have relatively low device rise it is bright and
Operating voltage, while there is of a relatively high luminous efficiency, and device lasts a long time.
In order to better illustrate naphthyridines substitution anthracene derivant provided by the invention and OLED device, specific implementation is set forth below
Example is explained.
Explanation：Various chemicals used chemical products can be commercially available at home in synthetic example；The present invention
In the compound of synthetic method do not mentioned be all the raw produce obtained by commercial sources；Intermediate in the present invention and
The analysis detection of compound uses AB SCIEX mass spectrographs (4000QTRAP) and Brooker Nuclear Magnetic Resonance (400M).
The synthesis of 1 compound A1 of synthetic example
Raw material N1 (13.5g, 0.01mol) and N2 (19.9g, 0.01mol) is placed in toluene, adds catalytic amount (3%eq)
P-methyl benzenesulfonic acid, is heated to reflux a point water, reacts about 12h, reaction solution concentration, adds ethanol, there is yellow powder precipitation, filter, obtain
To intermediate N3.
Intermediate N3 (22.1g, 0.01mol) is placed in dilute hydrochloric acid, adds hydrogen bromide (30g, 0.012mol), room temperature stirs
Mix, react 12h, reaction solution is added to the water, and ethyl acetate extraction, organic phase concentration, by column chromatography for separation, obtains intermediate
N4。
Under nitrogen protection, 2- bromo anthraquinones M1 (26.5g, 0.01mol), pinacol borate (0.015mol), Pd (dppf)
Cl2(1%), potassium carbonate mixing is dissolved in 500ml toluene, is heated to flowing back, and overnight, reaction solution column chromatography, concentrates, petroleum ether for reaction
Boil and wash, obtain intermediate M2 (20.1g, yield 89.6%).
Under nitrogen protection, added into the there-necked flask equipped with mechanical stirring device intermediate M2 (6.7g, 22mmol,
1.1eq), intermediate N4 (1eq), potassium carbonate (5eq), Pd (Pph3)4(2%), toluene 1000ml+ ethanol 500ml+300ml water,
Stirring is opened, is heated to flowing back, reacts 8h.Organic phase silica gel column chromatography, concentration, yellow powder M3 is obtained with re crystallization from toluene
(9.0g, 93.7%).
Under nitrogen protection, (25mmol) 2- bromonaphthalenes are dissolved in tetrahydrofuran, and ice ethanol bath is down to -78 DEG C, and n-BuLi is added dropwise
Solution, keeps cryogenic conditions, is added dropwise, temperature control 30min, intermediate M3 (4.8g, 10mmol) is dissolved in tetrahydrofuran, drips
Add in reaction bulb, be added dropwise, heat up naturally, react 8h.Dilute hydrochloric acid is added in reaction solution, is extracted with ethyl acetate, it is organic
Mutually concentrate, solid separates out, and intermediate M4 (4.8g, 93.1%) is obtained by filtration.
Intermediate M4 (5.1g, 10mmol), adds in reaction bulb, adds 100ml glacial acetic acid, adds potassium iodide
(20mmol), adds hypophosphorous acid hydrogen sodium (20mmol), is heated to flowing back, and reacts 5h.Filtering, with water, ethanol rinse, collection obtains
Yellow powder A1 (5.3g, 79.1%).
The magnetic resonance spectroscopy data of compound A1：
1H NMR(400MHz,CDCl3) δ 8.79 (d, J=12.0Hz, 2H), 8.39 (d, J=2.6Hz, 2H), 8.31
(s,1H),8.20(s,2H),8.16–8.04(m,5H),7.99(s,2H),7.63(s,2H),7.60– 7.51(m,6H),7.39
(d, J=12.0Hz, 4H), 7.19 (s, 4H)
The synthesis of 2. compound A4 of synthetic example
Under nitrogen protection, added into the there-necked flask equipped with mechanical stirring device intermediate M (9.4g, 22mmol,
1.1eq), intermediate N4 (1eq), potassium carbonate (5eq), Pd (Pph3)4(2%), toluene 1000ml+ ethanol 500ml+300ml water,
Stirring is opened, is heated to flowing back, reacts 8h.Organic phase silica gel column chromatography, concentration, yellow powder M1 is obtained with re crystallization from toluene
(9.0g, 93.7%).
Under nitrogen protection, intermediate M1 (4.6g, 10mmol, 1eq) is dissolved in 100ml chloroforms, adds 1.1eqNBS (N- bromines
For succinimide), stirring at normal temperature, reacts about 30min, water is added in reaction solution, stir, liquid separation, organic phase concentration, in obtaining
Mesosome M2.
Under nitrogen protection, intermediate M2 (10mmol, 1eq), 1- naphthalenes are added into the there-necked flask equipped with mechanical stirring device
Boric acid (1eq), potassium carbonate (5eq), Pd (Pph3) 4 (2%), toluene 1000ml+ ethanol 500ml+300ml water, open stirring,
It is heated to flowing back, reacts 8h.Organic phase silica gel column chromatography, concentration, yellow powder A4 is obtained with re crystallization from toluene
The magnetic resonance spectroscopy data of compound A4：
1H NMR(400MHz,CDCl3) δ 8.91 (d, J=8.0Hz, 2H), 8.50 (s, 1H), 8.32 (d, J=8.0Hz,
3H), 8.20 (s, 2H), 8.15-8.02 (m, 4H), 8.00 (s, 2H), 7.92 (dd, J=12.4,6.8 Hz, 4H), 7.78 (d, J
=4.0Hz, 2H), 7.63 (s, 1H), 7.60-7.46 (m, 6H), 7.43-7.31 (m, 3H)
The synthesis of 3 compound A11 of synthetic example
Under nitrogen protection, intermediate N1 (28.7g, 0.1mol, 1eq), intermediate ethyl-boron dihydroxide are added in there-necked flask
(1eq), potassium carbonate (5eq), Pd (Pph3)4(2%), toluene 1000ml+ ethanol 500ml+300ml water, opens stirring, is heated to
Reflux, reacts 8h.Organic phase silica gel column chromatography, concentration, yellow powder N2 (25.8g, 92.6%) is obtained with re crystallization from toluene.
Nitrogen protection under, in there-necked flask add intermediate N2 (0.1mol, 1eq), 2- phenyl -4- bromobenzeneboronic acids (1eq),
Potassium carbonate (5eq), Pd (Pph3)4(2%), toluene 1000ml+ ethanol 500ml+300ml water, opens stirring, is heated to flowing back, instead
Answer 8h.Organic phase silica gel column chromatography, concentration, yellow powder N3 (15.3g, 75.1%) is obtained with re crystallization from toluene.
Under nitrogen protection, 2- bromo anthraquinones M1 (26.5g, 0.01mol), pinacol borate (0.015mol), Pd (dppf)
Cl2(1%), potassium carbonate mixing is dissolved in 500ml toluene, is heated to flowing back, and overnight, reaction solution column chromatography, concentrates, petroleum ether for reaction
Boil and wash, obtain intermediate M2 (20.1g, yield 89.6%).
Under nitrogen protection, added into the there-necked flask equipped with mechanical stirring device intermediate M2 (6.7g, 22mmol,
1.1eq), intermediate N3 (1eq), potassium carbonate (5eq), Pd (Pph3)4(2%), toluene 1000ml+ ethanol 500ml+300ml water,
Stirring is opened, is heated to flowing back, reacts 8h.Organic phase silica gel column chromatography, concentration, yellow powder M3 is obtained with re crystallization from toluene
(9.0g, 93.7%).
Under nitrogen protection, bromobenzene (25mmol) is dissolved in tetrahydrofuran, ice ethanol bath is down to -78 DEG C, and n-BuLi is added dropwise
Solution, keeps cryogenic conditions, is added dropwise, temperature control 30min, intermediate M3 (4.8g, 10mmol) is dissolved in tetrahydrofuran, drips
Add in reaction bulb, be added dropwise, heat up naturally, react 8h.Dilute hydrochloric acid is added in reaction solution, is extracted with ethyl acetate, it is organic
Mutually concentrate, solid separates out, and intermediate M4 (4.8g, 93.1%) is obtained by filtration.
Intermediate M4 (5.1g, 10mmol), adds in reaction bulb, adds 100ml glacial acetic acid, adds potassium iodide
(20mmol), adds hypophosphorous acid hydrogen sodium (20mmol), is heated to flowing back, and reacts 5h.Filtering, with water, ethanol rinse, collection obtains
Yellow powder A11 (5.3g, 79.1%).
The magnetic resonance spectroscopy data of compound A11：
1H NMR(400MHz,CDCl3) δ 8.99 (s, 2H), 8.54 (s, 2H), 8.37 (s, 2H), 8.24 (t, J=
22.0Hz, 7H), 8.18 (d, J=4.1Hz, 1H), 8.11 (s, 2H), 7.79 (s, 4H), 7.63 (d, J=14.4 Hz, 10H),
7.59–7.37(m,26H),7.35(s,2H),3.40(t,4H),1.30(t,6H).
The synthesis of 4 compound A17 of synthetic example
Under nitrogen protection, intermediate N1 (1eq), 2- pyridine boronic acids are added into the there-necked flask equipped with mechanical stirring device
(1eq), potassium carbonate (5eq), Pd (Pph3)4(2%), toluene 1000ml+ ethanol 500ml+ water 300ml, open stirring, are heated to
Reflux, reacts 8h.Organic phase silica gel column chromatography, concentration, yellow powder N2 (9.0g, 93.7%) is obtained with re crystallization from toluene.
Under nitrogen protection, by N2 (26.5g, 0.01mol), pinacol borate (0.015mol), Pd (dppf) Cl2
(1%), potassium carbonate mixing is dissolved in 500ml toluene, is heated to flowing back, and reaction is overnight.Reaction solution column chromatography, concentration, petroleum ether boil
Wash, obtain intermediate N3 (20.1g, yield 89.6%).
Under nitrogen protection, intermediate 2- bromo anthraquinones (1eq), phenyl boric acid are added into the there-necked flask equipped with mechanical stirring device
(1eq), potassium carbonate 5eq, Pd (Pph3)4(2%), toluene 1000ml+ ethanol 500ml+ water 300ml, open stirring, are heated to back
Stream, reacts 8h.Organic phase silica gel column chromatography, concentration, yellow powder M1 (9.0g, 93.7%) is obtained with re crystallization from toluene.
Under nitrogen protection, intermediate M1 (4.6g, 10mmol, 1eq) is dissolved in 100ml chloroforms, adds 1.1eqNBS, and room temperature stirs
Mix, react about 30min, water is added in reaction solution, stir, liquid separation, organic phase concentration, obtains intermediate M2.
Under nitrogen protection, intermediate M2 (1eq), intermediate N3 are added into the there-necked flask equipped with mechanical stirring device
(1eq), potassium carbonate (5eq), Pd (Pph3)4(2%), toluene 1000ml+ ethanol 500ml+ water 300ml, open stirring, are heated to
Reflux, reacts 8h.Organic phase silica gel column chromatography, concentration, yellow powder M3 (9.0g, 93.7%) is obtained with re crystallization from toluene.
Under nitrogen protection, 2- bromonaphthalenes (25mmol) are dissolved in tetrahydrofuran, ice ethanol bath is down to -78 DEG C, and normal-butyl is added dropwise
Lithium solution, keeps cryogenic conditions, is added dropwise, temperature control 30min, intermediate M3 (4.8g, 10 mmol) is dissolved in tetrahydrofuran,
It is added dropwise in reaction bulb, is added dropwise, heat up naturally, reacts 8h.Dilute hydrochloric acid is added in reaction solution, is extracted with ethyl acetate, is had
Machine mutually concentrates, and solid separates out, and intermediate M4 (4.8g, 93.1%) is obtained by filtration.
Intermediate M4 (5.1g, 10mmol) is added in reaction bulb, add 100ml glacial acetic acid, add potassium iodide
(20mmol), adds hypophosphorous acid hydrogen sodium (20mmol), is heated to flowing back, and reacts 5h.Filtering, with water, ethanol rinse, collection obtains
Yellow powder A17 (5.3g, 79.1%).
The magnetic resonance spectroscopy data of compound A17：
1H NMR(400MHz,CDCl3) δ 9.15 (dd, J=12.4,8.0Hz, 4H), 8.96 (s, 1H), 8.96 (s,
1H), 8.58-8.52 (m, 2H), 8.39-8.20 (m, 4H), 8.08 (d, J=12.0Hz, 4H), 7.99 (s, 3H), 7.77-
7.69 (m, 3H), 7.67-7.57 (m, 5H), 7.52 (d, J=24.0Hz, 4H), 7.39 (d, J=12.0Hz, 3H), 7.23 (s,
1H).
The Elemental analysis data of compound A1-A21
Using above-mentioned synthetic method and similar synthetic method, the compound of above-mentioned A1-A21 is synthesized, their element
Analysis detecting data arranges in table 1 below：
The elemental analysis result of 1 compound A1-A21 of table
The device embodiments 1-9 of OLED
The structure of this OLED device embodiment 1-9 is, according to " hole injection layer (HIL)/hole transmission layer on substrate
(HTL)/luminescent layer (EML)/electron transfer layer (ETL)/electron injecting layer (EIL)/cathode " order stacking, each layer it is specific
Material is：
ITO/2-TNATA(30nm)/NPB(20nm)/CBP：Ir(ppy)3(5%) (20nm)/electron transport material
(50nm)/LiF(1nm)/Al。
Wherein, as shown in table 2, electron transport material can only select one or more electric transmissions provided by the invention
Material, can also use the electron transport material of the present invention and the doping of other kinds of electron transport material.
Device comparative example 1-4
If table 2 with above-mentioned device embodiments 1-9 in order to be contrasted, present invention also offers device comparative example 1-4.Device
The structure of part comparative example 1-4 is identical with device embodiments 1-9, and difference is only selecting the prior art with electron transport material
In common electron transport material.
OLED device embodiment 1-9 and the preparation process of device comparative example 1-4 are as follows：
The glass substrate that surface is coated with to transparent conductive film is cleaned by ultrasonic in cleaning solution, in deionized water
It is ultrasonically treated, in ethanol：Ultrasonic oil removing, is baked under clean environment and removes moisture removal completely, use is ultraviolet in acetone mixed solution
Lamp performs etching 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 on anode tunic, adjusting evaporation rate are 0.1nm/s, form the hole injection layer that thickness is 30nm.
The vacuum evaporation compound N PB on hole injection layer, forms the hole transmission layer that thickness is 20nm, and evaporation rate is
0.1nm/s.Luminescent layers of the vacuum evaporation EML as device on hole transmission layer, EML include material of main part and dyestuff material
Material, the method steamed altogether using multi-source, it is 0.1nm/s, dye materials Ir (ppy) to adjust material of main part CBP evaporation rates3Evaporation speed
Rate is set according to doping ratio, and evaporation total film thickness is 20nm.
Total film thickness is deposited as described above, its evaporation rate is 0.1nm/s in material solution when preparing device electron transfer layer
For 50nm.
For the LiF that vacuum evaporation thickness is 1nm on electron transfer layer (ETL) as electron injecting layer, thickness is 150nm's
The Al layers of cathode as device.
To gained organic electroluminescence device in same brightness (10000cd/m2) under measure driving voltage and current efficiency,
Performance is shown in Table 2.
Driving voltage, current efficiency and LT90s of the ETL of 2 each OLED device of table under same brightness
By table 2 as it can be seen that other materials is identical in OLED device structure in the case of, ETL materials in device are not using
Same compound, compared with device comparative example 1-4, device embodiments 1-9 of the invention significantly decreases the operating voltage of device,
And device current efficiency is increased substantially, so as to improve the luminous efficiency of device；The brightness of OLED decays to 90% from 100%
The time LT90 of Shi Suoyong is significantly improved, that is, extends the service life of OLED device layer.
Above-mentioned significantly higher performance is derived from the electron transfer layer material that it is used possessed by the device embodiments of the present invention
The characteristic of material.Preferable electron transport material, it should which there is the characteristic of following several respects：First, HOMO and lumo energy close
Suitable, electron mobility is high；Secondth, heat endurance is high, it is necessary to which molecular weight is sufficiently large, and guarantee has higher Tg；3rd, film forming
Good, i.e., in order to form a film beneficial to vacuum evaporation, molecular weight cannot be too big.First, relative to Alq3And CA, electronics provided by the invention
Layer material is transmitted, coplanarity is good, so that electric transmission rate is high.Secondly, in CC-1,2 and 6, the active site of anthracene nucleus does not have
Substituted base protection so that the material is perishable under the high temperature conditions, so as to influence luminous efficiency and service life；It is and of the invention
The electron transport material of offer, protects active site in 2 or 2 and 6 substds, heat endurance is improved, so as to send out
Light efficiency is higher, lasts a long time.
In addition, material of the present invention doping or is adulterated in use, under the conditions of different doping ratios mutually from LiQ, and not
Doping embodiment, which is compared, achieves lower device voltage, while can keep under efficiency unanimous circumstances, the service life during which
There is obvious extension.
The above description is merely a specific embodiment, but protection scope of the present invention is not limited thereto, any
Those familiar with the art the invention discloses technical scope in, the change or replacement that can readily occur in, all should
It is included within the scope of the present invention.Therefore, protection scope of the present invention should be subject to scope of the claims.
It is further to note that each particular technique feature described in above-mentioned embodiment, in not lance
In the case of shield, can be combined by any suitable means, in order to avoid unnecessary repetition, the present invention to it is various can
The combination of energy no longer separately illustrates.In addition, any group can also be carried out between a variety of embodiments of the present invention
Close, as long as it without prejudice to the thought of the present invention, it should equally be considered as content disclosed in this invention.
Claims (14)
1. a kind of naphthyridines substitutes anthracene derivant, it is characterised in that has the structure shown in below formula (I)：
Wherein, L is selected from chemical bond, substituted or unsubstituted C6~C12Arlydene or sub- condensed-nuclei aromatics group, substitution or do not take
The C in generation3~C12Inferior heteroaryl or sub- condensed hetero ring aromatic hydrocarbon group；
Ar1、Ar2It is respectively and independently selected from substituted or non-substituted C6~C30Aryl or condensed-nuclei aromatics group, substituted or non-substituted
C3~C30Heteroaryl or condensed hetero ring aromatic hydrocarbon group；
R1、R2、R3、R4It is respectively and independently selected from hydrogen, C1~C10Alkyl, halogen, cyano group, nitro, substituted or unsubstituted C6~C30
Aryl or condensed-nuclei aromatics group, substituted or unsubstituted C3~C30Heteroaryl or condensed hetero ring aromatic hydrocarbon group.
2. naphthyridines according to claim 1 substitutes anthracene derivant, it is characterised in that point of the naphthyridines substitution anthracene derivant
Son amount is less than 1000.
3. naphthyridines according to claim 2 substitutes anthracene derivant, it is characterised in that point of the naphthyridines substitution anthracene derivant
Son amount is 450~900.
4. naphthyridines according to claim 3 substitutes anthracene derivant, it is characterised in that point of the naphthyridines substitution anthracene derivant
Son amount is 600~800.
5. naphthyridines according to claim 1 substitutes anthracene derivant, it is characterised in that R1、R2、R3And R4It is respectively and independently selected from
Hydrogen, C1~C5Alkyl, halogen, cyano group, nitro, C6~C15Substituted or unsubstituted aryl or condensed-nuclei aromatics group, C3~C15
Substituted or unsubstituted heteroaryl or condensed hetero ring aromatic hydrocarbon group.
6. naphthyridines according to claim 1 substitutes anthracene derivant, it is characterised in that the L is selected from the C of substitution6~C12's
Arlydene or sub- condensed-nuclei aromatics group, C3~C12Inferior heteroaryl or sub- condensed hetero ring aromatic hydrocarbon group,
Wherein, the C6~C12Arlydene or sub- condensed-nuclei aromatics group, C3~C12Inferior heteroaryl or sub- condensed hetero ring aryl
Substituted radical in group is independently selected from by halogen, cyano group, nitro, C1~C10Alkyl or cycloalkyl, C2~C10Alkenyl, C1~
C6Alkoxy or thio alkoxy group, C6~C30Mononuclear aromatics or condensed-nuclei aromatics group, containing selected from N, O, S, Si
Hetero atom and C6~C30Mononuclear aromatics or condensed-nuclei aromatics group, and Si (R5)3The group of composition,
Wherein, R5Selected from C1~C6Alkyl.
7. naphthyridines according to claim 1 substitutes anthracene derivant, it is characterised in that the Ar1、Ar2Independently it preferably is selected from
C6~C20Substituted or non-substituted aryl or condensed-nuclei aromatics group, C5~C20Substituted or non-substituted heteroaryl or condensed hetero ring
Aromatic hydrocarbon group.
8. naphthyridines according to claim 1 substitutes anthracene derivant, it is characterised in that the Ar1、Ar2It is respectively and independently selected from and takes
Generation or non-substituted C3~C30Heteroaryl or condensed hetero ring aromatic hydrocarbon group, wherein on the heteroaryl or condensed hetero ring aromatic hydrocarbon group
Hetero atom is one or more O, S and/or N.
9. naphthyridines according to claim 7 substitutes anthracene derivant, it is characterised in that the Ar1、Ar2It is respectively and independently selected from benzene
Base, xenyl, naphthyl, phenyl, phenylpyridyl, anthryl, phenanthryl, furyl, benzofurane base, the thiophene of pyridine radicals substitution
Base, tolylthiophene base, pyrrole radicals, phenylpyrrole base or pyridine radicals.
10. naphthyridines according to claim 5 substitutes anthracene derivant, it is characterised in that the R1、R2、R3And R4Independently
Selected from methyl, ethyl, propyl group, isopropyl, the tert-butyl group, phenyl, naphthyl, pyridine radicals, phenylpyridyl, dibenzofuran group or connection
Phenyl.
11. naphthyridines according to claim 1 substitutes anthracene derivant, it is characterised in that the naphthyridines substitution anthracene derivant choosing
The group that the compound that free following structural formula is A1-A21 forms：
12. a kind of organic electroluminescence device, including electron transfer layer, it is characterised in that the electron transfer layer include to
A kind of few naphthyridines as any one of claim 1-10 substitutes anthracene derivant as electron transport material.
13. according to claim 12 any one of them organic electroluminescence device, it is characterised in that the electron transfer layer is also
Including 8-hydroxyquinoline lithium.
14. organic electroluminescence device according to claim 13, it is characterised in that the naphthyridines in the electron transfer layer
The doping part by weight for substituting anthracene derivant and 8-hydroxyquinoline lithium is 90:10-10:90.
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| KR20140082437A (en) * | 2012-12-24 | 2014-07-02 | 에스에프씨 주식회사 | Antracene derivatives having heteroaryl substituted phenyl group and organic light-emitting diode including the same |
| CN105143186A (en) * | 2013-02-22 | 2015-12-09 | 出光兴产株式会社 | Anthracene derivative, material for organic electroluminescent element, and electronic device |
| CN105321984A (en) * | 2014-08-01 | 2016-02-10 | 乐金显示有限公司 | Organic light emitting display device |
| CN106279148A (en) * | 2015-05-22 | 2017-01-04 | 上海和辉光电有限公司 | Promote OLED high temperature, the material of high current density performance and application thereof |
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| KR20140082437A (en) * | 2012-12-24 | 2014-07-02 | 에스에프씨 주식회사 | Antracene derivatives having heteroaryl substituted phenyl group and organic light-emitting diode including the same |
| CN105143186A (en) * | 2013-02-22 | 2015-12-09 | 出光兴产株式会社 | Anthracene derivative, material for organic electroluminescent element, and electronic device |
| CN105321984A (en) * | 2014-08-01 | 2016-02-10 | 乐金显示有限公司 | Organic light emitting display device |
| CN106279148A (en) * | 2015-05-22 | 2017-01-04 | 上海和辉光电有限公司 | Promote OLED high temperature, the material of high current density performance and application thereof |
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| WO2019011261A1 (en) * | 2017-07-12 | 2019-01-17 | 北京鼎材科技有限公司 | Naphthyridine substituted anthracene derivative and organic electroluminescent device |
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