CN108929234A - A kind of preparation of aromatic amine derivatives and its organic electroluminescence device - Google Patents

A kind of preparation of aromatic amine derivatives and its organic electroluminescence device Download PDF

Info

Publication number
CN108929234A
CN108929234A CN201810728147.0A CN201810728147A CN108929234A CN 108929234 A CN108929234 A CN 108929234A CN 201810728147 A CN201810728147 A CN 201810728147A CN 108929234 A CN108929234 A CN 108929234A
Authority
CN
China
Prior art keywords
unsubstituted
substituted
preparation
aromatic amine
amine derivatives
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
CN201810728147.0A
Other languages
Chinese (zh)
Other versions
CN108929234B (en
Inventor
周雯庭
蔡辉
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Changchun Haipurunsi Technology Co Ltd
Original Assignee
Changchun Haipurunsi Technology Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Changchun Haipurunsi Technology Co Ltd filed Critical Changchun Haipurunsi Technology Co Ltd
Priority to CN201810728147.0A priority Critical patent/CN108929234B/en
Publication of CN108929234A publication Critical patent/CN108929234A/en
Application granted granted Critical
Publication of CN108929234B publication Critical patent/CN108929234B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • C07D471/06—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/58—Naphthylamines; N-substituted derivatives thereof
    • 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
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • 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
    • C07D209/88—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
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • 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
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D491/06—Peri-condensed systems
    • 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
    • C07D495/06—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a kind of preparation of aromatic amine derivatives and its organic electroluminescence devices, are related to organic optoelectronic materials technology.Preparation of aromatic amine derivatives of the invention is electron rich system, and has biggish conjugated structure, therefore hole mobility with higher, shows preferable hole transport performance.In addition preparation of aromatic amine derivatives of the invention due to bulky group introducing therefore there is biggish rigid structure, effectively raise the glass transition temperature and thermal stability of material, be conducive to material filming.Organic electroluminescence device of the invention includes anode, cathode and one or more organic matter layers, and for organic matter layer between anode and cathode, at least one layer in organic matter layer contains preparation of aromatic amine derivatives of the invention.Organic electroluminescence device of the invention has lower driving voltage, higher luminous efficiency and luminous brightness, and has longer service life.

Description

A kind of preparation of aromatic amine derivatives and its organic electroluminescence device
Technical field
The present invention relates to organic photoelectrical material technical fields, and in particular to a kind of preparation of aromatic amine derivatives and its organic electroluminescence Luminescent device.
Background technique
Organic photoelectrical material is the organic material of the generation with photon and electronics, conversion and transmission characteristic.Currently, organic Photoelectric material has been applied to organic electroluminescence device (Organic Light-Emitting Diode, OLED).OLED is Refer to the device that organic photoelectrical material shines under the action of electric current or electric field, electric energy can be converted into luminous energy by it.In recent years Carry out OLED just to receive more and more attention as FPD of new generation and solid state lighting technology.Compared to liquid crystal display skill Art, OLED are shone with its low-power consumption, actively, fast response time, high contrast, no angle limit, can make the spies such as Flexible Displays Point is increasingly used in display and lighting area.
Usual OLED has a multilayered structure, including tin indium oxide (ITO) anode and metallic cathode and be placed in ito anode with Several organic matter layers between metallic cathode, such as hole injection layer (HIL), hole transmission layer (HTL), luminescent layer (EML), electronics Transport layer (ETL) and electron injecting layer (EIL) etc..Under certain voltage driving, hole and electronics are infused by anode and cathode respectively Entering to hole transmission layer and electron transfer layer, the two passes through hole transmission layer respectively and electron transfer layer moves to luminescent layer, when The two is met in luminescent layer forms hole-electron compound exciton when combining, exciton returns to ground state by way of luminescence relaxation, It is luminous to achieve the purpose that.
As the hole transmission layer in OLED, basic role is the efficiency of transmission of raising hole in the devices, and will be electric Son is effectively blocked in luminescent layer, realizes that the maximum of carrier is compound；Energy wall of the hole in injection process is reduced simultaneously It builds, the injection efficiency in hole is improved, to improve the brightness of device, efficiency and service life.
Currently, usually there is the problems such as operation voltage is high, luminous efficiency is low, service life is short in organic electroluminescence device. Thus, exploring the new organic photoelectrical material for organic electroluminescence device is that those skilled in the art study all the time Emphasis direction.For hole transmission layer, traditionally material used, can not usually provide the satisfactory characteristics of luminescence, Therefore, it is still necessary to design the better hole mobile material of new performance to improve the service performance of organic electroluminescence device.
Summary of the invention
Goal of the invention: in view of the above-mentioned problems, the object of the present invention is to provide a kind of preparation of aromatic amine derivatives and its Organic Electricities Electroluminescence device, which applies in organic electroluminescence device as hole mobile material, to reduce The driving voltage of organic electroluminescence device, improves the luminous efficiency and brightness of organic electroluminescence device, and extend The service life of organic electroluminescence device.
Above-mentioned technical purpose of the invention is achieved through the following technical solutions: a kind of preparation of aromatic amine derivatives, the virtue Fragrant amine derivant has the general structure as shown in structural formula I:
Wherein, the Ar1、Ar4The independent alkyl selected from substituted or unsubstituted C1~C30, substituted or unsubstituted C6 One of the aryl of~C60, heteroaryl of substituted or unsubstituted C3~C60；
The Ar2、Ar3It is independent to be selected from one of following group,
The X is selected from C (R1)2、N(R1), O or S, the R1Alkyl selected from substituted or unsubstituted C1~C10 takes One of generation or the aryl of unsubstituted C6~C24, heteroaryl of substituted or unsubstituted C3~C24, the A be selected from hydrogen, Substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted naphthalene Base, substituted or unsubstituted quinolyl, substituted or unsubstituted phenanthryl or following group,The Y is selected from N (R2), O or S, the R2The aryl of alkyl, substituted or unsubstituted C6~C24 selected from substituted or unsubstituted C1~C10, One of the heteroaryl of substituted or unsubstituted C3~C24；
The X1、X2、X3、X4、X5、X6It is independent to be selected from C (R3) or N, the R3Selected from hydrogen, substituted or unsubstituted C1 The alkyl of~C10, the aryl of substituted or unsubstituted C6~C24, substituted or unsubstituted C3~C24 heteroaryl in one Kind, the B be selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, Substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted naphthalene, substituted or unsubstituted quinoline One of quinoline base, substituted or unsubstituted phenanthryl.
Preferably, the X is selected from N (R1), O or S, the R1Alkyl selected from substituted or unsubstituted C1~C10 takes One of the aryl of generation or unsubstituted C6~C18, heteroaryl of substituted or unsubstituted C3~C18.
Preferably, the Y is selected from N (R2), the R2Alkyl selected from substituted or unsubstituted C1~C10 replaces or does not take One of the aryl of the C6~C18 in generation, heteroaryl of substituted or unsubstituted C3~C18.
Preferably, the Ar1、Ar4It is the independent aryl selected from substituted or unsubstituted C6~C30, substituted or unsubstituted One of heteroaryl of C3~C30.
Preferably, the Ar1、Ar4It is independent to be selected from one of following group,
Wherein, the Z is selected from C (R4)2、N(R4), O or S, the R4Alkane selected from substituted or unsubstituted C1~C10 One of base, the aryl of substituted or unsubstituted C6~C24, heteroaryl of substituted or unsubstituted C3~C24；
The L is selected from the Asia of singly-bound, the arlydene of substituted or unsubstituted C6~C24, substituted or unsubstituted C3~C24 One of heteroaryl；
The Y1、Y2、Y3、Y4、Y5、Y6、Y7、Y8It is independent to be selected from C (R5) or N, the R5Selected from hydrogen, replaces or do not take The alkyl of the C1~C10 in generation, the aryl of substituted or unsubstituted C6~C24, substituted or unsubstituted C3~C24 heteroaryl in One kind.
Preferably, the L is selected from singly-bound, substituted or unsubstituted phenylene, substituted or unsubstituted sub-pyridyl group, substitution Or it is unsubstituted sub- pyrimidine radicals, substituted or unsubstituted naphthylene, substituted or unsubstituted sub- quinolyl, substituted or unsubstituted Phenanthrylene, substituted or unsubstituted fluorenylidene, substituted or unsubstituted sub- carbazyl, substituted or unsubstituted sub- dibenzofurans One of base, substituted or unsubstituted sub- dibenzothiophene.
Most preferably, preparation of aromatic amine derivatives of the invention is selected from one of chemical structure as follows,
Further, the present invention also provides a kind of organic electroluminescence device, which includes sun Pole, cathode and one or more organic matter layers, at least one layer of the organic matter layer between anode and cathode, in organic matter layer Preparation of aromatic amine derivatives containing aforementioned present invention.
Preferably, organic matter layer includes hole transmission layer, and the hole transmission layer is containing preparation of aromatic amine derivatives of the invention.
The utility model has the advantages that preparation of aromatic amine derivatives of the invention is electron rich system, and there is biggish conjugated structure, because This hole mobility with higher shows preferable hole transport performance.In addition preparation of aromatic amine derivatives of the invention by Therefore there is biggish rigid structure in the introducing of bulky group, effectively raise the glass transition temperature and thermostabilization of material Property, be conducive to material filming.
Organic electroluminescence device using preparation of aromatic amine derivatives of the invention as organic matter layer has lower drive Dynamic voltage, higher luminous efficiency and luminous brightness, and there is longer service life.
Specific embodiment
Combined with specific embodiments below, the present invention is furture elucidated, it should be understood that these embodiments are merely to illustrate the present invention Rather than limit the scope of the invention, after the present invention has been read, those skilled in the art are to various equivalences of the invention The modification of form falls within the application range as defined in the appended claims.
A kind of preparation of aromatic amine derivatives, the preparation of aromatic amine derivatives have the general structure as shown in structural formula I:
Wherein, the Ar1、Ar4The independent alkyl selected from substituted or unsubstituted C1~C30, substituted or unsubstituted C6 One of the aryl of~C60, heteroaryl of substituted or unsubstituted C3~C60；
The Ar2、Ar3It is independent to be selected from one of following group,
The X is selected from C (R1)2、N(R1), O or S, the R1Alkyl selected from substituted or unsubstituted C1~C10 takes One of generation or the aryl of unsubstituted C6~C24, heteroaryl of substituted or unsubstituted C3~C24, the A be selected from hydrogen, Substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted naphthalene Base, substituted or unsubstituted quinolyl, substituted or unsubstituted phenanthryl or following group,The Y is selected from N (R2)、 O or S, the R2The aryl of alkyl, substituted or unsubstituted C6~C24 selected from substituted or unsubstituted C1~C10 replaces Or one of heteroaryl of unsubstituted C3~C24；
The X1、X2、X3、X4、X5、X6It is independent to be selected from C (R3) or N, the R3Selected from hydrogen, substituted or unsubstituted C1 The alkyl of~C10, the aryl of substituted or unsubstituted C6~C24, substituted or unsubstituted C3~C24 heteroaryl in one Kind, the B be selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, Substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted naphthalene, substituted or unsubstituted quinoline One of quinoline base, substituted or unsubstituted phenanthryl.
Preferably, the X is selected from N (R1), O or S, the R1Alkyl selected from substituted or unsubstituted C1~C10 takes One of the aryl of generation or unsubstituted C6~C18, heteroaryl of substituted or unsubstituted C3~C18.
Preferably, the Y is selected from N (R2), the R2Alkyl selected from substituted or unsubstituted C1~C10 replaces or does not take One of the aryl of the C6~C18 in generation, heteroaryl of substituted or unsubstituted C3~C18.
Preferably, the Ar1、Ar4It is the independent aryl selected from substituted or unsubstituted C6~C30, substituted or unsubstituted One of heteroaryl of C3~C30.
Preferably, the Ar1、Ar4It is independent to be selected from one of following group,
Wherein, the Z is selected from C (R4)2、N(R4), O or S, the R4Alkane selected from substituted or unsubstituted C1~C10 One of base, the aryl of substituted or unsubstituted C6~C24, heteroaryl of substituted or unsubstituted C3~C24；
The L is selected from the Asia of singly-bound, the arlydene of substituted or unsubstituted C6~C24, substituted or unsubstituted C3~C24 One of heteroaryl；
The Y1、Y2、Y3、Y4、Y5、Y6、Y7、Y8It is independent to be selected from C (R5) or N, the R5Selected from hydrogen, replaces or do not take The alkyl of the C1~C10 in generation, the aryl of substituted or unsubstituted C6~C24, substituted or unsubstituted C3~C24 heteroaryl in One kind.
Preferably, the L is selected from singly-bound, substituted or unsubstituted phenylene, substituted or unsubstituted sub-pyridyl group, substitution Or it is unsubstituted sub- pyrimidine radicals, substituted or unsubstituted naphthylene, substituted or unsubstituted sub- quinolyl, substituted or unsubstituted Phenanthrylene, substituted or unsubstituted fluorenylidene, substituted or unsubstituted sub- carbazyl, substituted or unsubstituted sub- dibenzofurans One of base, substituted or unsubstituted sub- dibenzothiophene.
According to the present invention, substituent group on abovementioned alkyl is independent selected from hydrogen, deuterium, cyano, trifluoromethyl, C1~C10 Alkyl, the alkoxy of C1~C10, the aryl of C6~C24 or C3~C24 heteroaryl；
Substituent group on above-mentioned aryl, heteroaryl it is independent selected from hydrogen, deuterium, cyano, trifluoromethyl, C1~C10 alkyl, The heteroaryl of the alkoxy of C1~C10, the aryl of C6~C24 or C3~C24.
Alkyl of the present invention refers to alkyl made of minusing a hydrogen atom in alkane molecule, can be straight chain alkane Base, branched alkyl, naphthenic base, example may include methyl, ethyl, propyl, isopropyl, normal-butyl, isobutyl group, sec-butyl, tertiary fourth Base, amyl, isopentyl, cyclopenta, cyclohexyl etc., but not limited to this.
Aryl of the present invention refers to remove a hydrogen atom on the aromatic core carbon of aromatic hydrocarbon molecule after, be left the total of univalent perssad Claiming, can be monocyclic aryl or fused ring aryl, example may include phenyl, xenyl, naphthalene, anthryl, phenanthryl or pyrenyl etc., but It is without being limited thereto.
Heteroaryl of the present invention refers to the group that one or more aromatic core carbon in aryl are substituted by hetero atom General name, the hetero atom include but is not limited to oxygen, sulphur or nitrogen-atoms, and the heteroaryl can be bicyclic heteroaryl or condensed ring heteroaryl Base, example may include pyridyl group, pyrrole radicals, pyridyl group, thienyl, furyl, indyl, quinolyl, isoquinolyl, benzo thiophene Pheno base, benzofuranyl, dibenzofuran group, dibenzothiophene, carbazyl etc., but not limited to this.
Arlydene of the present invention refers to remove two hydrogen atoms on the aromatic core carbon of aromatic hydrocarbon molecule after, be left univalent perssad General name, can be monocycle arlydene or condensed ring arlydene, example may include phenylene, biphenylene, naphthylene, anthrylene, Phenanthrylene or sub- pyrenyl etc., but not limited to this.
Heteroarylidene of the present invention refers to the base that one or more aromatic core carbon in arlydene are substituted by hetero atom The general name of group, the hetero atom include but is not limited to oxygen, sulphur or nitrogen-atoms, the heteroarylidene can for monocycle heteroarylidene or Condensed ring heteroarylidene, example may include sub-pyridyl group, sub- pyrrole radicals, sub-pyridyl group, sub- thienyl, furylidene, sub- indyl, Sub- quinolyl, sub- isoquinolyl, sub- benzothienyl, sub- benzofuranyl, sub- dibenzofuran group, sub- dibenzothiophene, Sub- carbazyl etc., but not limited to this.
The alkyl of substituted or unsubstituted C1~C10 of the present invention, substituted or unsubstituted C6~C24 aryl, take The heteroaryl of generation or unsubstituted C3~C24 refer to be substituted before alkyl, aryl, heteroaryl the total number of carbon atoms be respectively 1~ 10,6~24,3~24, and so on.
As an example, it is not particularly limited, preparation of aromatic amine derivatives of the invention is in chemical structure as follows One kind,
The synthetic route of preparation of aromatic amine derivatives of the invention is as follows:
Wherein, the Ar1、Ar4The independent alkyl selected from substituted or unsubstituted C1~C30, substituted or unsubstituted C6 One of the aryl of~C60, heteroaryl of substituted or unsubstituted C3~C60；
The Ar2、Ar3It is independent to be selected from one of following group,
The X is selected from C (R1)2、N(R1), O or S, the R1Alkyl selected from substituted or unsubstituted C1~C10 takes One of generation or the aryl of unsubstituted C6~C24, heteroaryl of substituted or unsubstituted C3~C24, the A be selected from hydrogen, Substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted naphthalene Base, substituted or unsubstituted quinolyl, substituted or unsubstituted phenanthryl or following group,The Y is selected from N (R2), O or S, the R2The aryl of alkyl, substituted or unsubstituted C6~C24 selected from substituted or unsubstituted C1~C10, One of the heteroaryl of substituted or unsubstituted C3~C24；
The X1、X2、X3、X4、X5、X6It is independent to be selected from C (R3) or N, the R3Selected from hydrogen, substituted or unsubstituted C1 The alkyl of~C10, the aryl of substituted or unsubstituted C6~C24, substituted or unsubstituted C3~C24 heteroaryl in one Kind, the B be selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, Substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted naphthalene, substituted or unsubstituted quinoline One of quinoline base, substituted or unsubstituted phenanthryl.
4- bromine 4- iodine biphenyl and compound pass through carbon nitrogen coupling reaction generation compound Sub II, compound Sub II and change It closes object SubI and product shown in structural formula I is generated by carbon nitrogen coupling reaction.
The synthetic route of preparation of aromatic amine derivatives of the invention is not particularly limited, those skilled in the art can be used Known popular response.
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device include anode, cathode with And one or more organic matter layers, between anode and cathode, at least one layer in organic matter layer contains above-mentioned organic matter layer Preparation of aromatic amine derivatives of the invention.
The organic matter layer of organic electroluminescence device of the invention can have single layer structure, or with two layers or more Multilayered structure.The organic matter layer of organic electroluminescence device of the invention may include hole injection layer, hole transmission layer, shine Layer, electron transfer layer, any one layer in electron injecting layer or any multilayer.Contain preparation of aromatic amine derivatives of the invention The thickness of organic matter layer is not higher than 6 μm, preferably not higher than 0.3 μm, and more preferably 0.002~0.3 μm.If desired, containing There is the organic matter layer of preparation of aromatic amine derivatives of the invention to can further include the hole as known in the art that can be carried out inject, is empty Cave transmission shines, the other materials of electron-transport and electron injection.
Preparation of aromatic amine derivatives of the invention specifically can be used as the hole mobile material for preparing organic electroluminescence device. The organic electroluminescence device of use is preferred are as follows: is attached to the ITO on transparent glass as anode, hole injection layer, hole passes Defeated layer, luminescent layer (material of main part: guest materials), electron transfer layer, electron injecting layer, metallic cathode.
Organic electroluminescence device of the invention can be used known materials and be prepared by known methods, however, Organic Electricity The structure of electroluminescence device is without being limited thereto.
Organic electroluminescence device of the invention can be widely applied to FPD, solid state lighting, Organophotoreceptor or have The fields such as machine thin film transistor (TFT).
The present invention is not particularly limited raw material employed in following embodiment, can be for commercial product or using this Preparation method known to the technical staff of field is prepared.
Embodiment 1: the preparation of compound TM5
The preparation of compound A1:
Under protection of argon gas, the chloro- 1H- indoles -2- boric acid (10.2g, 52.3mmol) of 5-, iodine are sequentially added into reaction flask Benzene (21.3g, 104.7mmol), CuI (5g, 26.2mmol), ethylenediamine (1.8ml, 26.2mmol), Cs2CO3(51.2g, 157.0mmol) with toluene (250ml), which is stirred one day.Organic phase is extracted with ethyl acetate, and is concentrated organic Phase obtains compound a 1 (7.1g, 50%) by column chromatographic purifying.
Under protection of argon gas, the bromo- naphthalidine of 8- (13.3g, 60.0mmol), compound a 1 are sequentially added into reaction flask (17.9g,66mmol)、NaOH(7.2g,180mmol)、Pd(PPh3)4(3.47g, 3mmol) and THF/H2O (80ml/40ml), Reaction mixture is stirred 12 hours under conditions of 80 DEG C, after reaction, is cooled to room temperature, is extracted with toluene, is closed And organic phase, by organic phase saturated common salt water washing, organic phase, by column chromatographic purifying, obtains chemical combination after drying, concentration Object b1 (17.7g, 80%).
Compound b1 (16.6g, 45.0mmol) is poured slowly into 5% hydrochloric acid (150ml), after stirring 30 minutes, at 0 DEG C Under sequentially add NaNO2The aqueous solution (30ml) of (3.7g, 54.0mmol), NaN3The aqueous solution of (3.5g, 54.0mmol) (30ml) is stirred 1 hour, after reaction, is extracted with toluene, merge organic phase, organic phase is successively used unsaturated carbonate The washing of hydrogen sodium solution, saturated common salt water washing, distillation water washing, organic phase, by column chromatographic purifying, obtain after drying, concentration To compound c1 (12.4g, 70%).
Compound c1 (16.6g, 30.0mmol) and 1,2- dichloro-benzenes (100ml), at 180 DEG C are sequentially added into reaction flask Under conditions of stir 2 hours, after reaction, be cooled to room temperature, extracted with toluene, merge organic phase, organic phase concentration Afterwards, by column chromatographic purifying, compound d1 (6.1g, 55%) is obtained.
Under protection of argon gas, sequentially added into reaction flask compound d1 (8.4g, 23.0mmol), iodobenzene (14.1g, 69.0mmol)、Cu(0.15g,2.3mmol)、K2CO3(6.3g,46.0mmol)、Na2SO4(6.5g, 46.0mmol) and nitrobenzene (150ml) is stirred 2 hours under conditions of 200 DEG C, after reaction, is cooled to room temperature, is extracted with toluene, is associated with Machine phase, by organic phase saturated common salt water washing, organic phase, by column chromatographic purifying, obtains compound A1 after drying, concentration (7.6g, 75%).
The preparation of compound Sub I-1:
Under protection of argon gas, into flask be added aniline (14.0g, 150mmol), compound A1 (44.3g, 100mmol), Sodium tert-butoxide (28.8g, 300mmol), tris(dibenzylideneacetone) dipalladium (1.4g, 1.5mmol), 1,1'- dinaphthalene -2,2'- are double Diphenyl phosphine (1.9g, 3mmol) and toluene (350ml) react 24 hours under conditions of 130 DEG C.After cooling, mixture is carried out Filtering, filtrate is concentrated under reduced pressure.Resulting crude product is subjected to column purification, is recrystallized with toluene, after being filtered, It is dried, as a result obtains intermediate Sub1-1 (42.5g, 85%).
The preparation of compound Sub II-1:
Under protection of argon gas, into flask be added diphenylamines (5.2g, 31mmol), 4- bromine 4- iodine biphenyl (11.1g, 31mmol), sodium tert-butoxide (3g, 31mmol), bis- (triphenylphosphine) palladium chlorides (II) (0.5g, 0.71mmol) and dimethylbenzene (500ml) reacts 24 hours under conditions of 130 DEG C.After cooling, it is added water (1000ml), mixture is filtered, will be filtered Liquid is extracted with toluene, and organic phase is dry with anhydrous magnesium sulfate.It is concentrated under reduced pressure, it is pure that resulting crude product is carried out column Change, is recrystallized with toluene, after being filtered, be dried, as a result obtain intermediate Sub II-1 (8.1g, 65%).
The preparation of compound TM5
Under protection of argon gas, into flask be added intermediate Sub1-1 (5.0g, 10mmol), intermediate Sub2-1 (4.0g, 10mmol), sodium tert-butoxide (1.3g, 13.5mmol), tris(dibenzylideneacetone) dipalladium (0.046g, 0.05mmol), three tertiary fourths Base phosphine (0.021g, 0.1mmol) and dehydrated toluene (50ml) react 2 hours at 80 DEG C.After cooling, it is added water (500ml), Mixture is filtered, filtrate is extracted with toluene, organic phase is dry with anhydrous magnesium sulfate.It is concentrated under reduced pressure, it will Resulting crude product carries out column purification, is recrystallized with toluene, after being filtered, is dried, as a result obtains product TM5 (5.7g, 70%).Mass spectrum m/z: theoretical value: 819.02；Measured value: 821.63.Theoretical elemental content (%) C60H42N4: C, 87.99；H,5.17；N,6.84；Survey constituent content (%): C, 87.96；H,5.22；N,6.82.The above results confirmation is produced Object is target product.
Embodiment 2: the preparation of compound TM13
Change the iodobenzene in embodiment 1 into equimolar 1- ethyl -4- iodobenzene, synthesis of other steps with embodiment 1 It is identical, obtain compound TM13 (6.6g, 75%).Mass spectrum m/z: theoretical value: 875.13；Measured value: 877.31.Theoretical elemental contains Measure (%) C64H50N4:, 87.84；H,5.76；N,6.40；It surveys constituent content (%):, 87.81；H,5.83；N,6.36.It is above-mentioned As a result confirm that obtaining product is target product.
Embodiment 3: the preparation of compound TM61
Change the diphenylamines in embodiment 1 into equimolar N- phenyl -4- benzidine, other steps with embodiment 1 It synthesizes identical, obtains compound TM61 (6.4g, 72%).Mass spectrum m/z: theoretical value: 895.12；Measured value: 896.73.Theoretical member Cellulose content (%) C66H46N4: C, 88.56；H,5.18；N,6.26；Survey constituent content (%): C, 88.54；H,5.23；N, 6.23.The above results confirm that obtaining product is target product.
Embodiment 4: the preparation of compound TM83
Change the chloro- 1H- indoles -2- boric acid of 5- in embodiment 1 into the chloro- 1H- indoles -2- boric acid of equimolar 6-, iodobenzene Change equimolar 4- iodine pyridine into, other steps are identical as the synthesis of embodiment 1, obtain compound TM83 (5.3g, 65%). Mass spectrum m/z: theoretical value: 821.00；Measured value: 823.51.Theoretical elemental content (%) C58H40N6: C, 84.85；H,4.91；N, 10.24；Survey constituent content (%): C, 84.82；H,4.97；N,10.21.The above results confirm that obtaining product is target product.
Embodiment 5: the preparation of compound TM109
Change the iodobenzene in embodiment 1 into equimolar iodomethane, diphenylamines changes equimolar N- phenyl dibenzo furan into It mutters -2- amine, other steps are identical as the synthesis of embodiment 1, obtain compound TM109 (5.4g, 69%).Mass spectrum m/z: theoretical Value: 784.96；Measured value: 786.03.Theoretical elemental content (%) C56H40N4O:C, 85.69；H,5.14；N,7.14；O,2.04； Survey constituent content (%): C, 85.66；H,5.21；N,7.12；O,2.02.The above results confirm that obtaining product is target product.
Embodiment 6: the preparation of compound TM125
Change the chloro- 1H- indoles -2- boric acid of 5- in embodiment 1 into the chloro- 1H- indoles -2- boric acid of equimolar 6-, hexichol Amine changes equimolar N- phenyl-2-naphthylamine into, other steps are identical as the synthesis of embodiment 1, obtains compound TM1125 (6.2g, 72%).Mass spectrum m/z: theoretical value: 869.08；Measured value: 870.42.Theoretical elemental content (%) C64H44N4: C, 88.45；H,5.10；N,6.45；Survey constituent content (%): C, 88.42；H,5.17；N,6.41.The above results confirmation is produced Object is target product.
Embodiment 7: the preparation of compound TM150
Change the iodobenzene in embodiment 1 into equimolar iodomethane, aniline changes equimolar benzidine into, and diphenylamines changes into - 9 hydrogen of equimolar 9,9- dimethyl-N-phenyl-fluorenes -3- amine, other steps are identical as the synthesis of embodiment 1, obtain chemical combination Object TM150 (6.2g, 70%).Mass spectrum m/z: theoretical value: 887.14；Measured value: 889.22.Theoretical elemental content (%) C65H50N4: C, 88.00；H,5.68；N,6.32；Survey constituent content (%): C, 87.97；H,5.72；N,6.31.The above results Confirm that obtaining product is target product.
Embodiment 8: the preparation of compound TM165
Change the chloro- 1H- indoles -2- boric acid of 5- in embodiment 1 into equimolar (6- bromobenzofuran -2- base) boric acid, Diphenylamines changes equimolar N- phenyl-2-naphthylamine into, other steps are identical as the synthesis of embodiment 1, obtains compound TM165 (4.9g, 62%).Mass spectrum m/z: theoretical value: 793.97；Measured value: 795.43.Theoretical elemental content (%) C58H39N3O:C, 87.74；H,4.95；N,5.29；O,2.02；Survey constituent content (%): C, 87.71；H,5.01；N,5.27；O,2.01.It is above-mentioned As a result confirm that obtaining product is target product.
Embodiment 9: the preparation of compound TM222
Change the chloro- 1H- indoles -2- boric acid of 5- in embodiment 1 into equimolar (the bromo- 1- benzothiophene -2- base of 5-) boron Acid, other steps are identical as the synthesis of embodiment 1, obtain compound TM222 (4.9g, 60%).Mass spectrum m/z: theoretical value: 759.97；Measured value: 760.62.Theoretical elemental content (%) C54H37N3S:C, 85.34；H,4.91；N,5.53；S,4.22；It is real Survey constituent content (%): C, 85.31；H,4.97；N,5.51；S,4.21.The above results confirm that obtaining product is target product.
Embodiment 10: the preparation of compound TM227
Change the chloro- 1H- indoles -2- boric acid of 5- in embodiment 1 into equimolar (the bromo- 1- benzothiophene -2- base of 5-) boron Acid, iodobenzene change equimolar iodomethane into, and aniline changes equimolar benzidine into, other steps with the synthesis phase of embodiment 1 Together, compound TM227 (4.9g, 63%) is obtained.Mass spectrum m/z: theoretical value: 774.00；Measured value: 775.41.Theoretical elemental contains Measure (%) C55H39N3S:C, 85.35；H,5.08；N,5.43；S,4.14；Survey constituent content (%): C, 85.31；H,5.15；N, 5.41；S,4.13.The above results confirm that obtaining product is target product.
Other target products are synthesized referring to the synthetic method of above-described embodiment 1-10.
Application Example 1: the preparation of luminescent device 1
Selection ito glass is anode, dries after ultrasonic cleaning as in vacuum chamber, is evacuated to 5 × 10-5Pa, above-mentioned Vacuum evaporation 2T-NATA is as hole injection layer, evaporation thickness 10nm in anode grid substrate.The vacuum evaporation on hole injection layer The compound of the present invention TM5 is as hole transmission layer, evaporation thickness 30nm.Vacuum evaporation ADN conduct on the hole transport layer Luminescent material layer main body, 2% DPAVBi is as doping, evaporation thickness 45nm.The vacuum evaporation vacuum on luminous material layer Evaporating Al q3As electron transfer layer, evaporation thickness 40nm.Vapor deposition LiF is steamed as electron injecting layer on the electron transport layer Plating is with a thickness of 0.2nm.Vacuum evaporation Al is as cathode, evaporation thickness 150nm on electron injecting layer.
Application Example 2: the preparation of luminescent device 2
Change the compound TM1 in Application Example 1 into compound TM13.
Application Example 3: the preparation of luminescent device 3
Change the compound TM1 in Application Example 1 into compound TM61.
Application Example 4: the preparation of luminescent device 4
Change the compound TM1 in Application Example 1 into compound TM83.
Application Example 5: the preparation of luminescent device 5
Change the compound TM1 in Application Example 1 into compound TM109.
Application Example 6: the preparation of luminescent device 6
Change the compound TM1 in Application Example 1 into compound TM125.
Application Example 7: the preparation of luminescent device 7
Change the compound TM1 in Application Example 1 into compound TM150.
Application Example 8: the preparation of luminescent device 8
Change the compound TM1 in Application Example 1 into compound TM165.
Application Example 9: the preparation of luminescent device 9
Change the compound TM1 in Application Example 1 into compound TM222.
Application Example 10: the preparation of luminescent device 10
Change the compound TM1 in Application Example 1 into compound TM227.
Comparative example 1
Selection ito glass is anode, dries after ultrasonic cleaning as in vacuum chamber, is evacuated to 5 × 10-5Pa, above-mentioned Vacuum evaporation 2T-NATA is as hole injection layer, evaporation thickness 10nm in anode grid substrate.The vacuum evaporation on hole injection layer NPB is as hole transmission layer, evaporation thickness 30nm.Vacuum evaporation AND is as luminescent material layer main body on the hole transport layer, 2% DPAVBi is as doping, evaporation thickness 45nm.The vacuum evaporation vacuum evaporation Alq on luminous material layer3As electronics Transport layer, evaporation thickness 40nm.Vapor deposition LiF is as electron injecting layer, evaporation thickness 0.2nm on the electron transport layer.? Vacuum evaporation Al is as cathode, evaporation thickness 150nm on electron injecting layer.
The characteristics of luminescence of organic electroluminescence device prepared by Application Example 1-10 of the present invention and comparative example 1 Test result is as shown in table 1.
Table 1
From table 1 it follows that preparation of aromatic amine derivatives of the invention is applied to organic electroluminescence as hole mobile material In luminescent device, which shows lower driving voltage, higher luminous efficiency and longer use Service life, and there is preferable durability and reliability.

Claims (9)

1. a kind of preparation of aromatic amine derivatives, which is characterized in that the preparation of aromatic amine derivatives has the structure as shown in structural formula I General formula:
Wherein, the Ar1、Ar4The independent alkyl selected from substituted or unsubstituted C1~C30, substituted or unsubstituted C6~ One of the aryl of C60, heteroaryl of substituted or unsubstituted C3~C60；
The Ar2、Ar3It is independent to be selected from one of following group,
The X is selected from C (R1)2、N(R1), O or S, the R1Alkyl selected from substituted or unsubstituted C1~C10 replaces or not One of the aryl of substituted C6~C24, heteroaryl of substituted or unsubstituted C3~C24, the A be selected from hydrogen, replace or Unsubstituted phenyl, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted naphthalene, takes substituted or unsubstituted pyridyl group Generation or unsubstituted quinolines base, substituted or unsubstituted phenanthryl or following group,The Y is selected from N (R2), O or Person S, the R2The aryl of alkyl, substituted or unsubstituted C6~C24 selected from substituted or unsubstituted C1~C10, replace or One of the heteroaryl of unsubstituted C3~C24；
The X1、X2、X3、X4、X5、X6It is independent to be selected from C (R3) or N, the R3Selected from hydrogen, substituted or unsubstituted C1~C10 Alkyl, the aryl of substituted or unsubstituted C6~C24, one of the heteroaryl of substituted or unsubstituted C3~C24, it is described B is selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substitution or not Substituted pyrazinyl, substituted or unsubstituted naphthalene, substituted or unsubstituted quinolyl, takes substituted or unsubstituted pyridazinyl One of generation or unsubstituted phenanthryl.
2. a kind of preparation of aromatic amine derivatives according to claim 1, which is characterized in that the X is selected from N (R1), O or S, The R1The aryl of alkyl, substituted or unsubstituted C6~C18 selected from substituted or unsubstituted C1~C10 replaces or does not take One of the heteroaryl of C3~C18 in generation.
3. a kind of preparation of aromatic amine derivatives according to claim 1, which is characterized in that the Y is selected from N (R2), the R2Choosing From the alkyl of substituted or unsubstituted C1~C10, the aryl of substituted or unsubstituted C6~C18, substituted or unsubstituted C3~ One of heteroaryl of C18.
4. a kind of preparation of aromatic amine derivatives according to claim 1, which is characterized in that the Ar1、Ar4Independent be selected from takes One of the aryl of generation or unsubstituted C6~C30, heteroaryl of substituted or unsubstituted C3~C30.
5. a kind of preparation of aromatic amine derivatives according to claim 1, which is characterized in that the Ar1、Ar4It is independent selected from One of lower group,
Wherein, the Z is selected from C (R4)2、N(R4), O or S, the R4Alkyl selected from substituted or unsubstituted C1~C10 takes One of the aryl of generation or unsubstituted C6~C24, heteroaryl of substituted or unsubstituted C3~C24；
The L is selected from the sub- heteroaryl of singly-bound, the arlydene of substituted or unsubstituted C6~C24, substituted or unsubstituted C3~C24 One of base；
The Y1、Y2、Y3、Y4、Y5、Y6、Y7、Y8It is independent to be selected from C (R5) or N, the R5Selected from hydrogen, substituted or unsubstituted C1 The alkyl of~C10, the aryl of substituted or unsubstituted C6~C24, substituted or unsubstituted C3~C24 heteroaryl in one Kind.
6. a kind of preparation of aromatic amine derivatives according to claim 5, which is characterized in that the L be selected from singly-bound, replace or not Substituted phenylene, substituted or unsubstituted sub-pyridyl group, substituted or unsubstituted sub- pyrimidine radicals, substituted or unsubstituted sub- naphthalene Base, substituted or unsubstituted sub- quinolyl, substituted or unsubstituted phenanthrylene, substituted or unsubstituted fluorenylidene, substitution or not Substituted sub- carbazyl, substituted or unsubstituted sub- dibenzofuran group, in substituted or unsubstituted sub- dibenzothiophene It is a kind of.
7. a kind of preparation of aromatic amine derivatives according to claim 1, which is characterized in that the preparation of aromatic amine derivatives is selected from One of chemical structure as follows,
8. a kind of organic electroluminescence device, which is characterized in that the organic electroluminescence device includes anode, cathode and one A or multiple organic matter layers, between anode and cathode, at least one layer in the organic matter layer contains the organic matter layer Preparation of aromatic amine derivatives described in claim 1-7 any one.
9. a kind of organic electroluminescence device according to claim 8, which is characterized in that the organic matter layer includes hole Transport layer, the hole transmission layer include preparation of aromatic amine derivatives described in claim 1-7 any one.
CN201810728147.0A 2018-07-05 2018-07-05 Aromatic amine derivative and organic electroluminescent device thereof Active CN108929234B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201810728147.0A CN108929234B (en) 2018-07-05 2018-07-05 Aromatic amine derivative and organic electroluminescent device thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201810728147.0A CN108929234B (en) 2018-07-05 2018-07-05 Aromatic amine derivative and organic electroluminescent device thereof

Publications (2)

Publication Number Publication Date
CN108929234A true CN108929234A (en) 2018-12-04
CN108929234B CN108929234B (en) 2021-12-14

Family

ID=64447114

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201810728147.0A Active CN108929234B (en) 2018-07-05 2018-07-05 Aromatic amine derivative and organic electroluminescent device thereof

Country Status (1)

Country Link
CN (1) CN108929234B (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020132549A (en) * 2019-02-15 2020-08-31 東ソー株式会社 Triphenylene compound and use therefor
CN111909134A (en) * 2019-05-07 2020-11-10 北京鼎材科技有限公司 Compound, application thereof and organic electroluminescent device comprising compound
CN113461547A (en) * 2020-03-31 2021-10-01 江苏三月科技股份有限公司 Diamine derivative for organic electroluminescent device
US20210399222A1 (en) * 2020-06-19 2021-12-23 Samsung Display Co., Ltd. Light-emitting device, method of manufacturing the same, and electronic apparatus including the light-emitting device
CN115636755A (en) * 2022-12-26 2023-01-24 烟台显华科技集团股份有限公司 Naphthyl substituted diarylamine compound and application thereof

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005037797A1 (en) * 2003-10-21 2005-04-28 Pharmacia Corporation Substituted pyrazole urea compounds for the treatment of inflammation
EP1997799A1 (en) * 2006-03-07 2008-12-03 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent device using same
KR20100071723A (en) * 2008-12-19 2010-06-29 엘지디스플레이 주식회사 Amine derivatives and organic light emitting diode device comprising the same
CN102334210A (en) * 2009-02-27 2012-01-25 出光兴产株式会社 Organic electroluminescent element
WO2015041428A1 (en) * 2013-09-17 2015-03-26 덕산네오룩스 주식회사 Organic electronic element using compound for organic electronic element and electronic device thereof
WO2016072691A1 (en) * 2014-11-05 2016-05-12 덕산네오룩스 주식회사 Organic electronic device and display device using composition for organic electronic device
CN108129380A (en) * 2018-01-17 2018-06-08 长春海谱润斯科技有限公司 A kind of aromatic amine compounds and its organic luminescent device

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005037797A1 (en) * 2003-10-21 2005-04-28 Pharmacia Corporation Substituted pyrazole urea compounds for the treatment of inflammation
EP1997799A1 (en) * 2006-03-07 2008-12-03 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent device using same
KR20100071723A (en) * 2008-12-19 2010-06-29 엘지디스플레이 주식회사 Amine derivatives and organic light emitting diode device comprising the same
CN102334210A (en) * 2009-02-27 2012-01-25 出光兴产株式会社 Organic electroluminescent element
WO2015041428A1 (en) * 2013-09-17 2015-03-26 덕산네오룩스 주식회사 Organic electronic element using compound for organic electronic element and electronic device thereof
WO2016072691A1 (en) * 2014-11-05 2016-05-12 덕산네오룩스 주식회사 Organic electronic device and display device using composition for organic electronic device
CN108129380A (en) * 2018-01-17 2018-06-08 长春海谱润斯科技有限公司 A kind of aromatic amine compounds and its organic luminescent device

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
孙妍妍: "铜催化苄基请电视机与芳基硼试剂的suzuki交叉偶联反应", 《中国优秀硕士学位论文全文数据库（电子期刊）工程科技I辑》 *
张贞发，等: "钯等过渡金属催化的卤代芳烃和胺的偶联反应", 《有机化学》 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020132549A (en) * 2019-02-15 2020-08-31 東ソー株式会社 Triphenylene compound and use therefor
JP7363045B2 (en) 2019-02-15 2023-10-18 東ソー株式会社 Triphenylene compounds and their uses
CN111909134A (en) * 2019-05-07 2020-11-10 北京鼎材科技有限公司 Compound, application thereof and organic electroluminescent device comprising compound
CN111909134B (en) * 2019-05-07 2024-04-26 北京鼎材科技有限公司 Compound and application thereof, and organic electroluminescent device comprising compound
CN113461547A (en) * 2020-03-31 2021-10-01 江苏三月科技股份有限公司 Diamine derivative for organic electroluminescent device
CN113461547B (en) * 2020-03-31 2023-11-21 江苏三月科技股份有限公司 Diamine derivative for organic electroluminescent device
US20210399222A1 (en) * 2020-06-19 2021-12-23 Samsung Display Co., Ltd. Light-emitting device, method of manufacturing the same, and electronic apparatus including the light-emitting device
CN115636755A (en) * 2022-12-26 2023-01-24 烟台显华科技集团股份有限公司 Naphthyl substituted diarylamine compound and application thereof

Also Published As

Publication number Publication date
CN108929234B (en) 2021-12-14

Similar Documents

Publication Publication Date Title
CN111138298B (en) Nitrogen-containing compound, electronic component, and electronic device
CN108929234A (en) A kind of preparation of aromatic amine derivatives and its organic electroluminescence device
CN111808085B (en) Compound and application thereof, and organic electroluminescent device comprising compound
CN110099902B (en) Novel compound and organic light-emitting element comprising same
KR20220007898A (en) Organic compounds, organic electroluminescent devices and electronic devices
CN108329286A (en) A kind of dopant material and its organic electroluminescence device
CN108822020A (en) A kind of benzidine derivative and its organic electroluminescence device
CN109020903A (en) A kind of triarylamine derivative and its organic electroluminescence device
CN109360905A (en) A kind of organic electroluminescence device
CN114805179B (en) Nitrogen-containing compound, organic electroluminescent device and electronic device
CN115745977A (en) Electron transport material, preparation method thereof and organic electroluminescent device
CN109251194A (en) A kind of triaizine compounds and its organic luminescent device of the class formation containing fluorenes
CN113214280B (en) Organic compound, and electronic device and electronic apparatus including the same
CN109400487A (en) A kind of fluorene kind derivative and its organic electroluminescence device
CN109096277A (en) A kind of derivative of phenanthroline and its organic electroluminescence device
CN109020901A (en) A kind of preparation of aromatic amine derivatives and its organic electroluminescence device
CN108807707A (en) A kind of organic luminescent device
KR101968353B1 (en) 1, 2, 4, 5-substituted phenyl derivative, production method for same, and organic electroluminescent element
CN108948015A (en) A kind of pyrene derivatives and its organic electroluminescence device
CN109053555A (en) A kind of compound and its organic luminescent device of cyano-containing structure
CN108503636A (en) A kind of electron transport material and its organic luminescent device
CN109180528A (en) A kind of triarylamine derivative and its organic electroluminescence device
CN113321649B (en) Compound, electron transport material and organic electroluminescent device
CN113380954B (en) Organic electroluminescent device and electronic apparatus
CN109180569A (en) A kind of compound and its organic luminescent device of the class formation containing pyrene

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
CB02 Change of applicant information
CB02 Change of applicant information

Address after: 130000 A5, North Lake Science and Technology Park, 3333 North Sheng street, Beihu science and Technology Development Zone, Jilin, Changchun

Applicant after: Changchun hiprunsi Technology Co., Ltd

Address before: 130000 A5, North Lake Science and Technology Park, 3333 North Sheng street, Beihu science and Technology Development Zone, Jilin, Changchun

Applicant before: CHANGCHUN HAIPURUNSI TECHNOLOGY Co.,Ltd.

GR01 Patent grant
GR01 Patent grant