CN106467543A - A kind of organic compound with dimethylanthracene as core and its application - Google Patents

A kind of organic compound with dimethylanthracene as core and its application Download PDF

Info

Publication number
CN106467543A
CN106467543A CN201610738755.0A CN201610738755A CN106467543A CN 106467543 A CN106467543 A CN 106467543A CN 201610738755 A CN201610738755 A CN 201610738755A CN 106467543 A CN106467543 A CN 106467543A
Authority
CN
China
Prior art keywords
formula
expressed
dimethylanthracene
organic compound
layer
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201610738755.0A
Other languages
Chinese (zh)
Other versions
CN106467543B (en
Inventor
王立春
张兆超
李崇
叶中华
张小庆
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.)
Jiangsu Sunera Technology Co Ltd
Original Assignee
Jiangsu Sanyue Optoelectronic 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 Jiangsu Sanyue Optoelectronic Technology Co Ltd filed Critical Jiangsu Sanyue Optoelectronic Technology Co Ltd
Priority to CN201610738755.0A priority Critical patent/CN106467543B/en
Publication of CN106467543A publication Critical patent/CN106467543A/en
Application granted granted Critical
Publication of CN106467543B publication Critical patent/CN106467543B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-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
    • 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
    • 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
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic 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
    • H10K85/657—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
    • 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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—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

Landscapes

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

Abstract

The invention discloses a kind of organic compound with dimethylanthracene as core and its application, shown in the structural formula formula such as formula (1) of this organic compound.The compounds of this invention has higher vitrification point and molecule heat stability, suitable HOMO and lumo energy, higher Eg, is optimized by device architecture, can effectively lift the photoelectric properties of OLED and the life-span of OLED.

Description

A kind of organic compound with dimethylanthracene as core and its application
Technical field
The present invention relates to organic photoelectrical material technical field, especially relate to one kind containing bone centered on dimethylanthracene structure The compound-material of frame and its application in OLED field.
Background technology
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology both can be used to make Make new display product it is also possible to be used for making novel illumination product, be expected to substitute existing liquid crystal display and fluorescent lighting, Application prospect is quite varied.
OLED luminescent device just as the structure of sandwich, including electrode material film layer, and be clipped in Different electrodes film layer it Between organic functional material, various difference in functionality materials are overlapped mutually according to purposes and collectively constitute OLED luminescent device together. As current device, when the two end electrodes applied voltage to OLED luminescent device, and pass through electric field action organic layer functional material Positive and negative charge in film layer, positive and negative charge is compound in luminescent layer further, that is, produce OLED electroluminescent.
Currently, in smart mobile phone, the field such as panel computer obtains application to OLED Display Technique, further also will be to electricity Depending on etc. the extension of large scale application, but, require to compare with the products application of reality, the luminous efficiency of OLED, use The performances such as life-span also need to be lifted further.
High performance research is carried for OLED luminescent device include：Reduce the driving voltage of device, improve the luminous of device Efficiency, improves service life of device etc..In order to realize the continuous lifting of the performance of OLED, not only need from OLED Structure and the innovation of processing technology, constantly study with greater need for oled light sulfate ferroelectric functional material and innovate, formulate out higher performance OLED Functional material.
The oled light sulfate ferroelectric functional material being applied to OLED can be divided into two big class from purposes, i.e. electric charge injection transmission Material and luminescent material, further, also can inject charge into transmission material and be divided into electron injection transmission material, electronic blocking material Luminescent material can also be divided into main body luminescent material and dopant material by material, hole injection transmission material and hole barrier materials.
In order to make high performance OLED luminescent device it is desirable to various organic functional material possesses good photoelectric characteristic, Such as, as charge transport materials it is desirable to have good carrier mobility, high-vitrification conversion temperature etc., as luminous The material of main part of layer requires material to have good bipolarity, suitable HOMO/LUMO energy rank etc..
The oled light sulfate ferroelectric functional material film layer constituting OLED at least includes the above structure of two-layer, application in industry OLED structure, then include hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electronics biography Multiple film layer such as defeated layer, electron injecting layer is that is to say, that the photoelectric functional material being applied to OLED includes at least hole note Enter material, hole mobile material, luminescent material, electron transport material etc., material type and collocation form have rich and many The feature of sample.In addition, for the OLED of different structure is arranged in pairs or groups, the photoelectric functional material that used has stronger Selectivity, performance in different structure device for the identical material is it is also possible to completely totally different.
Therefore, for the industry application requirement of current OLED, and the difference in functionality film layer of OLED, device Photoelectric characteristic demand, it is necessary to select to be more suitable for, has high performance OLED functional material or combination of materials, just enables device The overall characteristic of high efficiency, long-life and low-voltage.For the actual demand that current OLED shows Lighting Industry, current OLED The development of material is also far from enough, lags behind the requirement of panel manufacturing enterprise, organic as material enterprise development higher performance Functional material is particularly important.
Content of the invention
The problems referred to above existing for prior art, the applicant provides a kind of organic compound containing dimethylanthracene And its apply on organic electroluminescence device.The compounds of this invention contains dimethylanthracene structure, has higher vitrification temperature Degree and molecule heat stability, suitable HOMO and lumo energy, higher Eg, optimized by device architecture, can effectively lift OLED The photoelectric properties of device and the life-span of OLED.
Technical scheme is as follows：
The applicant provides a kind of organic compound containing dimethylanthracene, the general structure such as formula of described compound (1) shown in：
Wherein, Ar1、Ar2Independently be expressed as phenyl, xenyl or naphthyl；
R1、R2Independently be expressed as formula (2) or structure shown in formula (3)；R1With R2Can be identical or different；R1Also Hydrogen atom can be expressed as；
Wherein,
R3It is expressed as hydrogen atom, formula (4) or structure shown in formula (5)；
In formula (4), a is selected fromX1、X2、X3Independently to be expressed as oxygen former Son, sulphur atom, C1-10The uncle that the alkylidene of straight or branched alkyl replacement, the alkylidene of aryl replacement, alkyl or aryl replace One of amido；
Formula (4), structure shown in formula (5) pass through CL1-CL2Key, CL2-CL3Key or CL3-CL4Key is connected with formula (2)；
R4、R5Independently be expressed as C1-10Straight or branched alkyl, phenyl, naphthyl, xenyl, formula (6), formula (7), formula (8) or structure shown in formula (9)；R5It is also denoted as hydrogen atom or halogen atom；
Wherein,
X is oxygen atom, sulphur atom, C1-10The alkylidene of straight or branched alkyl replacement, the alkylidene of aryl replacement, alkyl One of or the tertiary amine groups of aryl replacement；
R7、R8Independently be expressed as phenyl, naphthyl, dibiphenylyl, terphenyl, dibenzofurans, dibenzo thiophene Fen or 9,9- dimethyl fluorene or carbazole.
Preferably, described R1、R2Being expressed as independently：
In any one.
Preferably, the concrete structure formula of the described organic compound containing dimethylanthracene is：
In Any one.
The applicant additionally provides a kind of method preparing described organic compound, the reactional equation occurring in preparation process Formula is：
R1When being expressed as hydrogen atom,
R1Be expressed as formula (2) or formula (3) structure when,
Specifically preparation process is：
Weigh dimethylanthracene bromo-derivative and H-R2Or H-R1With H-R2Mixture, dissolved with toluene；Add Pd2 (dba)3, tri-butyl phosphine, sodium tert-butoxide；Under an inert atmosphere, by the mixed solution of above-mentioned reactant in reaction temperature 95～ 110 DEG C, react 10～24 hours, cooling simultaneously filtering reacting solution, filtrate revolving, cross silicagel column, obtain target product；
Described dimethylanthracene bromo-derivative and H-R1And H-R2Mol ratio be respectively 1:1.2～3.0, Pd2(dba)3With diformazan The mol ratio of base anthracene bromo-derivative is 0.006～0.02:1, the mol ratio of tri-butyl phosphine and dimethylanthracene bromo-derivative is 0.006～ 0.02:1, sodium tert-butoxide is 2.0～5.0 with the mol ratio of dimethylanthracene bromo-derivative:1.
The applicant additionally provides a kind of organic electroluminescence device, and described organic electroluminescence device includes at least one of which Functional layer contains the described organic compound containing dimethylanthracene.
Beneficial the having technical effect that of the present invention：
The compounds of this invention with dimethylanthracene as parent nucleus, connected symmetrical dendrimer or asymmetrical rigid radical, the knot of saboteur Crystalline substance, it is to avoid intermolecular aggregation, has high vitrification point, and material, when OLED is applied, can keep high Membranous layer stability, improves OLED service life.
The compounds of this invention structure makes electronics and hole more balance in the distribution of luminescent layer, in appropriate HOMO energy level Under, improve hole injection/transmission performance；Under suitable lumo energy, serve the effect of electronic blocking again, lift exciton Combined efficiency in luminescent layer；As OLED luminescent device light emitting functional layer materials'use when, aryl replace dimethyl The side chain that anthracene is arranged in pairs or groups in the scope of the invention can effectively improve exciton utilization rate and high fluorescent radiation efficiency, reduces under high current density Efficiency roll-off, reduce device voltage, improve the current efficiency of device and life-span.
The special construction of compound of the present invention designs so that material also has while having high decomposition temperature Low sublimation temperature or vacuum evaporation temperature, have higher temperature difference window between sublimation temperature or evaporation temperature and decomposition temperature Mouth, so that material has higher operation controllability in commercial Application, is applied beneficial to material volume production.
Compound of the present invention has good application effect in OLED luminescent device, before having good industrialization Scape.
Brief description
Materials application cited by the present invention for the Fig. 1 is in the structural representation of OLED；
Wherein, 1 is transparent substrate layer, and 2 is ito anode layer, and 3 is hole injection layer, and 4 is hole transport/electronic barrier layer, 5 is luminescent layer, and 6 is electric transmission/hole blocking layer, and 7 is electron injecting layer, and 8 is negative electrode reflection electrode layer.
Specific embodiment
With reference to the accompanying drawings and examples, the present invention is specifically described.
Embodiment 1：The synthesis of compound 1：
Synthetic route：
In the there-necked flask of 250ml, under logical nitrogen protection, addition 0.01mol raw material A 1,0.012mol raw material B1, 0.03mol sodium tert-butoxide, 5 × 10-5molpd2(dba)3, 5 × 10-5Mol tri-tert phosphorus, 150ml toluene, it is heated to reflux 24 little When, sample point plate, reaction is completely；Natural cooling, filters, filtrate revolving, column chromatography obtains target product, HPLC purity 98.9%, yield 64.7%；
Elementary analysiss structure (molecular formula C64H45N3)：Theoretical value C, 89.79；H,5.30；N,4.91；Test value：C, 89.79；H,5.31；N,4.90.
HPLC-MS：Material molecule amount is 856.06, surveys molecular weight 856.45.
Embodiment 2：The synthesis of compound 3：
Synthetic route：
In the there-necked flask of 250ml, under logical nitrogen protection, addition 0.01mol raw material A 1,0.012mol raw material B2, 0.03mol sodium tert-butoxide, 5 × 10-5mol pd2(dba)3, 5 × 10-5Mol tri-tert phosphorus, 150ml toluene, it is heated to reflux 24 Hour, sample point plate, reaction is completely；Natural cooling, filters, filtrate revolving, column chromatography obtains target product, HPLC purity 99.5%, yield 67.3%；
Elementary analysiss structure (molecular formula C61H48N2)：Theoretical value C, 90.56；H,5.98；N,3.46；Test value：C, 90.59；H,5.96；N,3.45.
HPLC-MS：Material molecule amount is 809.05, surveys molecular weight 809.48.
Embodiment 3：The synthesis of compound 11：
Synthetic route：
In the there-necked flask of 250ml, under logical nitrogen protection, addition 0.01mol raw material A 1,0.012mol raw material C1, 0.03mol sodium tert-butoxide, 5 × 10-5mol pd2(dba)3, 5 × 10-5Mol tri-tert phosphorus, 150ml toluene, it is heated to reflux 24 Hour, sample point plate, reaction is completely；Natural cooling, filters, filtrate revolving, column chromatography obtains target product, HPLC purity 99.4%, yield 70.2%；
Elementary analysiss structure (molecular formula C56H40N2)：Theoretical value C, 90.78；H,5.44；N,3.78；Test value：C, 90.78；H,5.45；N,3.77.
HPLC-MS：Material molecule amount is 740.93, surveys molecular weight 741.25.
Embodiment 4：The synthesis of compound 16：
Synthetic route：
In the there-necked flask of 250ml, under logical nitrogen protection, addition 0.01mol raw material A 2,0.012mol raw material B3, 0.03mol sodium tert-butoxide, 5 × 10-5mol pd2(dba)3, 5 × 10-5Mol tri-tert phosphorus, 150ml toluene, it is heated to reflux 24 Hour, sample point plate, reaction is completely；Natural cooling, filters, filtrate revolving, column chromatography obtains target product, HPLC purity 99.1%, yield 68.5%；
Elementary analysiss structure (molecular formula C56H39NS)：Theoretical value C, 88.74；H,5.19；N,1.85；S,4.23；Test Value：C,88.73；H,5.20；N,1.86；S,4.21.
HPLC-MS：Material molecule amount is 757.98, surveys molecular weight 758.36.
Embodiment 5：The synthesis of compound 17：
Synthetic route：
By the synthetic method preparation of compound 1 in embodiment 1, difference is to replace raw material B1 with raw material B4；
Elementary analysiss structure (molecular formula C64H52N2)：Theoretical value C, 90.53；H,6.17；N,3.30；Test value：C, 90.54；H,6.15；N,3.31.
HPLC-MS：Material molecule amount is 849.11, surveys molecular weight 849.52.
Embodiment 6：The synthesis of compound 24：
Synthetic route：
By the synthetic method preparation of compound 1 in embodiment 1, difference is to replace raw material B1 with raw material C2；
Elementary analysiss structure (molecular formula C59H46N2)：Theoretical value C, 90.50；H,5.92；N,3.58；Test value：C, 90.52；H,5.91；N,3.57.
HPLC-MS：Material molecule amount is 783.01, surveys molecular weight 783.39.
Embodiment 7：The synthesis of compound 35：
Synthetic route：
By the synthetic method preparation of compound 1 in embodiment 1, difference is to replace raw material B1 with raw material D1；
Elementary analysiss structure (molecular formula C67H53N3)：Theoretical value C, 89.40；H,5.93；N,4.67；Test value：C, 89.43；H,5.92；N,4.65.
HPLC-MS：Material molecule amount is 900.16, surveys molecular weight 900.59.
Embodiment 8：The synthesis of compound 37：
Synthetic route：
By the synthetic method preparation of compound 1 in embodiment 1, difference is to replace raw material B1 with raw material D2；
Elementary analysiss structure (molecular formula C64H52N2O)：Theoretical value C, 88.85；H,6.06；N,3.24；O,1.85；Test Value：C,88.86；H,6.05；N,3.25；O,1.84.
HPLC-MS：Material molecule amount is 865.11, surveys molecular weight 865.48.
Embodiment 9：The synthesis of compound 42：
Synthetic route：
In the there-necked flask of 250ml, under logical nitrogen protection, addition 0.01mol raw material A 3,0.024mol raw material E1, 0.04mol sodium tert-butoxide, 1 × 10-4mol pd2(dba)3, 1 × 10-4Mol tri-tert phosphorus, 250ml toluene, it is heated to reflux 24 Hour, sample point plate, reaction is completely；Natural cooling, filters, filtrate revolving, column chromatography obtains target product, HPLC purity 99.5%, yield 68.9%；
Elementary analysiss structure (molecular formula C68H70N2)：Theoretical value C, 89.23；H,7.71；N,3.06；Test value：C, 89.25；H,7.70；N,3.05.
HPLC-MS：Material molecule amount is 915.30, surveys molecular weight 915.78.
Embodiment 10：The synthesis of compound 48：
Synthetic route：
In the there-necked flask of 250ml, under logical nitrogen protection, addition 0.01mol raw material A 4,0.012mol raw material E2, 0.03mol sodium tert-butoxide, 5 × 10-5mol pd2(dba)3, 5 × 10-5Mol tri-tert phosphorus, 250ml toluene, it is heated to reflux 24 Hour, sample point plate, reaction is completely；Natural cooling, filters, filtrate revolving, column chromatography obtains target product, HPLC purity 99.1%, yield 72.7%；
Elementary analysiss structure (molecular formula C58H44N2)：Theoretical value C, 90.59；H,5.77；N,3.64；Test value：C, 90.60；H,5.75；N,3.65.
HPLC-MS：Material molecule amount is 768.98, surveys molecular weight 769.31.
Embodiment 11：The synthesis of compound 61：
Synthetic route：
By the synthetic method preparation of compound 1 in embodiment 1, difference is to replace raw material B1 with raw material E3；
Elementary analysiss structure (molecular formula C64H45N3)：Theoretical value C, 89.79；H,5.30；N,4.91；Test value：C, 89.80；H,5.30；N,4.90.
HPLC-MS：Material molecule amount is 856.06, surveys molecular weight 856.42.
Embodiment 12：The synthesis of compound 69：
Synthetic route：
By the synthetic method preparation of compound 1 in embodiment 1, difference is to replace raw material B1 with raw material E4；
Elementary analysiss structure (molecular formula C70H57N3)：Theoretical value C, 89.42；H,6.11；N,4.47；Test value：C, 89.43；H,6.12；N,4.45.
HPLC-MS：Material molecule amount is 940.22, surveys molecular weight 940.69.
Embodiment 13：The synthesis of compound 72：
Synthetic route：
By the synthetic method preparation of compound 1 in embodiment 1, difference is to replace raw material B1 with raw material E5；
Elementary analysiss structure (molecular formula C64H49N3)：Theoretical value C, 89.37；H,5.74；N,4.89；Test value：C, 89.35；H,5.75；N,4.90.
HPLC-MS：Material molecule amount is 860.09, surveys molecular weight 860.51.
The compounds of this invention uses in luminescent device, can be as hole transport/electronic blocking layer material it is also possible to make For luminescent layer Subjective and Objective materials'use.The compounds of this invention has high operability and practicality, major embodiment in application For having high glass transition temperature, low sublimation temperature, high decomposition temperature and film forming stability.
The compounds of this invention 17, compound 44, compound 60 and current material CBP are carried out respectively with hot property, luminous light Spectrum, the test of HOMO energy level, testing result is as shown in table 1.
Table 1
Note：Vitrification point Tg is by differential scanning calorimetry (DSC, German Nai Chi company DSC204F1 differential scanning calorimetry Instrument) measure, 10 DEG C/min of heating rate；Evaporation temperature is using SUNIC evaporated device, vacuum ＜ 1E-5Pa, material rate ForWhen evaporation temperature；Thermal weight loss temperature Td is in nitrogen atmosphere weightless 1% temperature, in Japanese Shimadzu Corporation It is measured on TGA-50H thermogravimetric analyzer, nitrogen flow is 20mL/min；Film forming stability refers to, using SUNIC evaporator Platform, is deposited with to glass substrate 100nm thickness thin film material, envelope in glove box environment (water oxygen content equal ＜ 1PPm) Dress, after encapsulation, glass sample under the conditions of double 80 (humidity 80%, 80 DEG C of temperature) places test 240 hours, uses micro- sem observation The crystal property of sample film；Highest occupied molecular orbital HOMO energy level and minimum occupied molecular orbital lumo energy are by photoelectron Transmitting spectrometer (AC-2 type PESA) test, tests as atmospheric environment.
From upper table data, the compounds of this invention has adjustable HOMO energy level, is suitable as difference in functionality layer material Use；Low evaporation temperature can make material in commercial Application, reduces heat radiation to Fine-mask influence of crust deformation in evaporation board, Improve OLED PPI grade, improve producing line yield；High film forming stability energy, ensure that material is being applied to OLED device During use after part, keep film morphology, do not formed local-crystalized, cause device electrode short circuit, improving OLED makes Use the life-span.
The OLED material describing present invention synthesis in detail below by way of device embodiments 1～10 and comparative example 1 is in the devices Application effect.The making work of device embodiments 2～10 of the present invention, comparative example 1 described device compared with device embodiments 1 Skill is identical, and employed identical baseplate material and electrode material, and the thickness of electrode material is also consistent, and institute is not Same is that the material of main part of the luminescent layer 5 in device or hole transport/electronic barrier layer are changed.Each embodiment gained device The performance test results of part are as shown in table 2.
Device embodiments 1
A kind of electroluminescent device, its preparation process includes：
A) the ito anode layer 2 on cleaning transparent substrate layer 1, deionized water, acetone, EtOH Sonicate cleaning each 15 respectively Minute, then process 2 minutes in plasma cleaner；
B) on ito anode layer 2, hole injection layer material HAT-CN is deposited with by vacuum evaporation mode, thickness is 10nm, This layer is as hole injection layer 3；
C) on hole injection layer 3, hole mobile material NPB is deposited with by vacuum evaporation mode, thickness is 80nm, this layer For hole transmission layer/electronic barrier layer 4；
D) it is deposited with luminescent layer 5 on hole transport/electronic barrier layer 4, the compounds of this invention 1 is used as main body Material, Ir (ppy)3As dopant material, material doped mass ratio is 10%, and thickness is 30nm；
E) on luminescent layer 5, electron transport material TPBI is deposited with by vacuum evaporation mode, thickness is 40nm, this layer Organic material uses as hole barrier/electron transfer layer 6；
F) on hole barrier/electron transfer layer 6, vacuum evaporation electron injecting layer LiF, thickness is 1nm, and this layer is electricity Sub- implanted layer 7；
G) on electron injecting layer 7, vacuum evaporation negative electrode Mg:Ag/Ag layer, Mg:Ag doping ratio is 9:1, thickness 15nm, Ag thickness 3nm, this layer is negative electrode reflection electrode layer 8；
Complete the making of electroluminescent device according to above-mentioned steps after, the current efficiency of measurement device and life-span, its result It is shown in Table 2.
The molecular machinery formula of associated materials is as follows：
Device embodiments 2
The present embodiment is with the difference of device embodiments 1：The luminescent layer material of main part of electroluminescent device is changed into The compounds of this invention 13, dopant material is Ir (ppy)3, doping mass ratio is 10%, the detection data of gained electroluminescent device It is shown in Table 2.
Device embodiments 3
The present embodiment is with the difference of device embodiments 1：The luminescent layer material of main part of electroluminescent device is changed into The compounds of this invention 17, dopant material is Ir (ppy)3, doping mass ratio is 10%, the detection data of gained electroluminescent device It is shown in Table 2.
Device embodiments 4
The present embodiment is with the difference of device embodiments 1：Hole transport/the electronic barrier layer of electroluminescent device 4 material is changed into the compounds of this invention 35, and the material of main part of luminescent layer 5 is known compound CBP, and dopant material is Ir (ppy)3, doping mass ratio is 10%, and the detection data of gained electroluminescent device is shown in Table 2.
Device embodiments 5
The present embodiment is with the difference of device embodiments 1：Hole transport/the electronic barrier layer of electroluminescent device 4 material is changed into the compounds of this invention 44, and the material of main part of luminescent layer 5 is known compound CBP, and dopant material is Ir (ppy)3, doping mass ratio is 10%, and the detection data of gained electroluminescent device is shown in Table 2.
Device embodiments 6
The present embodiment is with the difference of device embodiments 1：Hole transport/the electronic barrier layer of electroluminescent device 4 material is changed into the compounds of this invention 48, and the material of main part of luminescent layer 5 is known compound CBP, and dopant material is Ir (ppy)3, doping mass ratio is 10%, and the detection data of gained electroluminescent device is shown in Table 2.
Device embodiments 7
The present embodiment is with the difference of device embodiments 1：Hole transport/the electronic barrier layer of electroluminescent device 4 material is changed into the compounds of this invention 60, and the material of main part of luminescent layer 5 is known compound CBP, and dopant material is Ir (ppy)3, doping mass ratio is 10%, and the detection data of gained electroluminescent device is shown in Table 2.
Device embodiments 8
The present embodiment is with the difference of device embodiments 1：Hole transport/the electronic barrier layer of electroluminescent device 4 material is changed into the compounds of this invention 65, and the material of main part of luminescent layer 5 is known compound CBP, and dopant material is Ir (ppy)3, doping mass ratio is 10%, and the detection data of gained electroluminescent device is shown in Table 2.
Device embodiments 9
The present embodiment is with the difference of device embodiments 1：The luminescent layer material of main part of electroluminescent device is changed into The compounds of this invention 61 and compound GHN, dopant material is Ir (ppy)3, the blending mass ratio of three kinds of materials is 60:30:10, The detection data of gained electroluminescent device is shown in Table 2.
Device embodiments 10
The present embodiment is with the difference of device embodiments 1：The luminescent layer material of main part of electroluminescent device is changed into The compounds of this invention 69 and compound GHN, dopant material is Ir (ppy)3, the blending mass ratio of three kinds of materials is 60:30:10, The detection data of gained electroluminescent device is shown in Table 2.
Device comparative example 1
The present embodiment is with the difference of device embodiments 1：The luminescent layer material of main part of electroluminescent device is changed into Known compound CBP, the detection data of gained electroluminescent device is shown in Table 2.
Table 2
Note：Using device comparative example 1 as reference, comparative example 1 device property indices are set to 1.0 to device detection performance. The current efficiency of comparative example 1 is 28cd/A (@10mA/cm2)；CIE chromaticity coordinates is (0.33,0.63)；The LT95 longevity under 5000 brightness Life decays to 2.5Hr.
Can be seen that the machine compound containing dimethylanthracene structure of the present invention can be applicable to OLED and sends out by the result of table 2 Optical device makes, and compared with comparative example, either efficiency or life-span all ratio known OLED material larger changes of acquisition, special It is not the larger lifting of the life time decay acquisition of device.
To sum up, the foregoing is only presently preferred embodiments of the present invention, not in order to limit the present invention, all essences in the present invention Within god and principle, any modification, equivalent substitution and improvement made etc., should be included within the scope of the present invention.

Claims (5)

1. a kind of organic compound containing dimethylanthracene is it is characterised in that general structure such as formula (1) institute of described compound Show：
Wherein, Ar1、Ar2Independently be expressed as phenyl, xenyl or naphthyl；
R1、R2Independently be expressed as formula (2) or structure shown in formula (3)；R1With R2Can be identical or different；R1Acceptable It is expressed as hydrogen atom；
Wherein,
R3It is expressed as hydrogen atom, formula (4) or structure shown in formula (5)；
In formula (4), a is selected fromX1、X2、X3Independently be expressed as oxygen atom, sulfur Atom, C1-10In the tertiary amine groups that the alkylidene of straight or branched alkyl replacement, the alkylidene of aryl replacement, alkyl or aryl replace One kind；
Formula (4), structure shown in formula (5) pass through CL1-CL2Key, CL2-CL3Key or CL3-CL4Key is connected with formula (2)；
R4、R5Independently be expressed as C1-10Straight or branched alkyl, phenyl, naphthyl, xenyl, formula (6), formula (7), Formula (8) or structure shown in formula (9)；R5It is also denoted as hydrogen atom or halogen atom；
Wherein,
X is oxygen atom, sulphur atom, C1-10Alkylidene, the alkylidene of aryl replacement, alkyl or virtue that straight or branched alkyl replaces One of tertiary amine groups that base replaces；
R7、R8Independently be expressed as phenyl, naphthyl, dibiphenylyl, terphenyl, dibenzofurans, dibenzothiophenes or 9,9- dimethyl fluorene or carbazole.
2. organic compound according to claim 1 is it is characterised in that described R1、R2Being expressed as independently：
In any one.
3. organic compound according to claim 1 is it is characterised in that the described organic compound containing dimethylanthracene Concrete structure formula is：
In any one.
4. a kind of method preparing organic compound described in claim 1 it is characterised in that in preparation process occur reaction side Formula is：
R1When being expressed as hydrogen atom,
R1Be expressed as formula (2) or formula (3) structure when,
Specifically preparation process is：
Weigh dimethylanthracene bromo-derivative and H-R2Or H-R1With H-R2Mixture, dissolved with toluene；Add Pd2(dba)3, three Tert-butyl group phosphine, sodium tert-butoxide；Under an inert atmosphere, by the mixed solution of above-mentioned reactant in 95～110 DEG C of reaction temperature, reaction 10～24 hours, cooling simultaneously filtering reacting solution, filtrate revolving, cross silicagel column, obtain target product；
Described dimethylanthracene bromo-derivative and H-R1And H-R2Mol ratio be respectively 1:1.2～3.0, Pd2(dba)3With dimethylanthracene The mol ratio of bromo-derivative is 0.006～0.02:1, the mol ratio of tri-butyl phosphine and dimethylanthracene bromo-derivative is 0.006～ 0.02:1, sodium tert-butoxide is 2.0～5.0 with the mol ratio of dimethylanthracene bromo-derivative:1.
5. a kind of organic electroluminescence device is it is characterised in that described organic electroluminescence device includes at least one of which functional layer Containing the organic compound containing dimethylanthracene any one of Claims 1 to 4.
CN201610738755.0A 2016-08-26 2016-08-26 It is a kind of using dimethylanthracene as the organic compound of core and its application Active CN106467543B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201610738755.0A CN106467543B (en) 2016-08-26 2016-08-26 It is a kind of using dimethylanthracene as the organic compound of core and its application

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201610738755.0A CN106467543B (en) 2016-08-26 2016-08-26 It is a kind of using dimethylanthracene as the organic compound of core and its application

Publications (2)

Publication Number Publication Date
CN106467543A true CN106467543A (en) 2017-03-01
CN106467543B CN106467543B (en) 2019-02-22

Family

ID=58230040

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201610738755.0A Active CN106467543B (en) 2016-08-26 2016-08-26 It is a kind of using dimethylanthracene as the organic compound of core and its application

Country Status (1)

Country Link
CN (1) CN106467543B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107513034A (en) * 2017-09-29 2017-12-26 江苏三月光电科技有限公司 A kind of dimethylanthracene class organic compound and its application
CN107686487A (en) * 2017-09-29 2018-02-13 江苏三月光电科技有限公司 A kind of dimethylanthracene class organic compound and its application on organic electroluminescence device

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004342391A (en) * 2003-05-14 2004-12-02 Konica Minolta Holdings Inc Organic electroluminescent device, lighting equipment and display unit
CN104693105A (en) * 2013-12-05 2015-06-10 乐金显示有限公司 Organic compound and organic light emitting diode using the same
CN105837498A (en) * 2016-04-25 2016-08-10 中节能万润股份有限公司 Organic compound containing dimethylanthracene structure and application thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004342391A (en) * 2003-05-14 2004-12-02 Konica Minolta Holdings Inc Organic electroluminescent device, lighting equipment and display unit
CN104693105A (en) * 2013-12-05 2015-06-10 乐金显示有限公司 Organic compound and organic light emitting diode using the same
CN105837498A (en) * 2016-04-25 2016-08-10 中节能万润股份有限公司 Organic compound containing dimethylanthracene structure and application thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107513034A (en) * 2017-09-29 2017-12-26 江苏三月光电科技有限公司 A kind of dimethylanthracene class organic compound and its application
CN107686487A (en) * 2017-09-29 2018-02-13 江苏三月光电科技有限公司 A kind of dimethylanthracene class organic compound and its application on organic electroluminescence device
CN107513034B (en) * 2017-09-29 2020-11-03 中节能万润股份有限公司 Dimethyl anthracene organic compound and application thereof

Also Published As

Publication number Publication date
CN106467543B (en) 2019-02-22

Similar Documents

Publication Publication Date Title
CN106467553B (en) A kind of boracic organic electroluminescent compounds and its application in OLED device
CN106467542B (en) It is a kind of using anthrone as the compound of core and its application
CN106478611B (en) It is a kind of using xanthene as the organic compound of core and its application
CN106467526B (en) A kind of organic compound containing xanthene and its application
CN106478610B (en) A kind of organic compound containing xanthene and its application in OLED device
CN106467486A (en) A kind of organic compound containing dimethylanthracene and its application
CN106220619B (en) A kind of organic compound containing xanthene structure and its application
CN106467523B (en) A kind of organic aromatic compound and its application
CN106543205B (en) A kind of compound containing benzimidazole and its application on OLED
CN105837498B (en) Organic compound containing dimethylanthracene structure and application thereof
CN107057681A (en) A kind of photoelectric material containing xanthene structure and its application in OLED fields
CN106220609A (en) A kind of compound with pyridine as core and the application on organic electroluminescence device thereof
CN106220649A (en) Diaryl ketone-based compound and application thereof in organic electroluminescent device
CN109956962A (en) It is a kind of fluorene structured for the compound of parent nucleus and its application on organic electroluminescence device with azaspiro
CN107056809B (en) It a kind of organic compound containing dimethylanthracene and its is applied on organic electroluminescence device
CN107056737B (en) Photoelectric material containing dimethyl anthracene structure and application thereof
CN110294663B (en) Compound with anthracene as core and application thereof in organic electroluminescent device
CN106543071B (en) Compound with dibenzoheptenone as core and application of compound in OLED
CN107868031A (en) One kind is using the fluorenes of 9,9 ' spiral shell two as the organic compound of core and its application on organic electroluminescence device
CN107021925B (en) Compound with aza-dibenzosuberone as core and application thereof in OLED
CN107056763A (en) A kind of electroluminescent organic material and its application using xanthene as core
CN110577488A (en) Compound with carbazole as core and application thereof in organic electroluminescent device
CN106467524B (en) A kind of organic aromatic compound and its application on organic electroluminescence device
CN106467511B (en) It is a kind of using acridone as the compound of core and its application on organic electroluminescence device
CN106467543B (en) It is a kind of using dimethylanthracene as the organic compound of core and its application

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
GR01 Patent grant
GR01 Patent grant
TR01 Transfer of patent right

Effective date of registration: 20200212

Address after: 264006 No. 11 Wuzhishan Road, Yantai economic and Technological Development Zone, Shandong

Patentee after: VALIANT Co.,Ltd.

Address before: 214112 No. 210, Xinzhou Road, New District, Jiangsu, Wuxi

Patentee before: JIANGSU SUNERA TECHNOLOGY Co.,Ltd.

TR01 Transfer of patent right
TR01 Transfer of patent right

Effective date of registration: 20211130

Address after: 214112 No.210 Xinzhou Road, Wuxi City, Jiangsu Province

Patentee after: Jiangsu March Technology Co., Ltd

Address before: 264006 No. 11 Wuzhishan Road, Yantai economic and Technological Development Zone, Shandong

Patentee before: VALIANT Co.,Ltd.

TR01 Transfer of patent right