CN106146538B - A kind of amine compounds and preparation method thereof and luminescent device - Google Patents

A kind of amine compounds and preparation method thereof and luminescent device Download PDF

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CN106146538B
CN106146538B CN201610505367.8A CN201610505367A CN106146538B CN 106146538 B CN106146538 B CN 106146538B CN 201610505367 A CN201610505367 A CN 201610505367A CN 106146538 B CN106146538 B CN 106146538B
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present
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amine compounds
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CN106146538A (en
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崔敦洙
高春吉
王辉
马晓宇
赵贺
李明
李文军
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Jilin Optical and Electronic Materials Co Ltd
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    • 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
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    • 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
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • 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
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    • 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
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    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • 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
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom

Abstract

The present invention provides a kind of amine compounds, have structure shown in formula 1-1 or formula 1-2；Wherein, Ar1For substituted or non-substituted C6~C60Aryl, substituted or non-substituted C5~C60Condensed ring radical；Y is carbon or nitrogen；RaAnd RbIt is independent to be selected from hydrogen, substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C6~C60Aryl；RcFor hydrogen, substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C1~C60Alkoxy；RdFor substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C6~C60Aryl.Amine compounds provided by the invention are in luminous efficiency and have preferable performance in terms of the service life.The present invention also provides a kind of preparation method of amine compounds and a kind of luminescent devices.

Description

A kind of amine compounds and preparation method thereof and luminescent device
Technical field
The present invention relates to electroluminescent technology field more particularly to a kind of amine compounds and preparation method thereof and photophores Part.
Background technique
General organic luminescent device (OLED) is the organic matter layer by being inserted between cathode, anode and cathode and anode It constitutes.As the composition of device can be transparent ITO anode, hole injection layer (TIL), hole transmission layer (HTL), luminescent layer (EL, hole blocking layer (HBL), electron transfer layer (ETL), electron injecting layer (EIL), LiAl cathode, can also omit 1 as needed ~2 organic layers.Voltage is formed between two electrodes of luminescent device, is injected on one side from cathode electronics, anode injection in another side is empty Cave, electrons and holes are in luminescent layer in conjunction with excitation state is formed, and then excitation state returns to stable ground state.
Luminescent material in luminescent device is divided into fluorescent material and phosphor material, and the forming method of luminescent layer is fluorescent host Phosphor material (organic metal) and fluorescent host material doping fluorescent (organic matter comprising nitrogen) dopant and hair are adulterated in material Using dopant (DCM, Rubrene, DCJTB etc.) etc. in body of light, doping in this way can improve emission wavelength, efficiency, The factors such as driving voltage, service life.Generally forming emitting layer material is with centers such as benzene, naphthalene, fluorenes, two fluorenes of spiral shell, anthracene, pyrene, carbazoles Structure, the ligands such as benzene, biphenyl, naphthalene, heterocycle, contraposition, meta position, ortho position binding site；And cyano, fluorine, methyl, tert-butyl etc. take For structure.
Oled panel develops to enlargement and needs finer and smoother and the distincter material of color, predominantly blue material, especially Being that needs are light blue moves on to navy blue high performance material, and the luminescent material that present technology provides is in luminous efficiency and in terms of the service life There is still a need for further increase to meet requirement.
Summary of the invention
In view of this, the purpose of the present invention is to provide a kind of amine compounds and preparation method thereof and luminescent device, this hair The aminate of bright offer is in luminous efficiency and has preferable performance in terms of the service life.
The present invention provides a kind of amine compounds, have structure shown in formula 1-1 or formula 1-2:
Wherein, Ar1For substituted or non-substituted C6~C60Aryl, substituted or non-substituted C5~C60Condensed ring radical, take Generation or non-substituted C5~C60Heterocycle；
Y is carbon or nitrogen；
RaAnd RbIt is independent to be selected from hydrogen, substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C6~C60Virtue Base, substituted or non-substituted C5~C60Condensed ring radical, substituted or non-substituted C5~C60Heterocycle；
RcFor hydrogen, substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C1~C60Alkoxy, replace or Non-substituted C1~C60Ether；
RdFor substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C6~C60Aryl, substitution or non-take The C in generation5~C60Condensed ring radical, substituted or non-substituted C5~C60Heterocycle.
Preferably, the amine compounds have structure shown in formula 2-1, formula 2-2 or formula 2-3:
Wherein, Ar2For substituted or non-substituted C6~C60Aryl, substituted or non-substituted C5~C60Condensed ring radical, take Generation or non-substituted C5~C60Heterocycle, substituted or non-substituted C6~C60Aryl amine；
Y is carbon or nitrogen；
RaAnd RbIt is independent to be selected from hydrogen, substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C6~C60Virtue Base, substituted or non-substituted C5~C60Condensed ring radical, substituted or non-substituted C5~C60Heterocycle.
Preferably, the amine compounds have structure shown in formula 3-1, formula 3-2 or formula 3-3:
Wherein, Ar3For substituted or non-substituted C6~C60Aryl, substituted or non-substituted C5~C60Condensed ring radical, take Generation or non-substituted C5~C60Heterocycle, substituted or non-substituted C6~C60Aryl amine；
Y is carbon or nitrogen；
RcFor hydrogen, substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C1~C60Alkoxy, replace or Non-substituted C1~C60Ether；
RdFor substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C6~C60Aryl, substitution or non-take The C in generation5~C60Condensed ring radical, substituted or non-substituted C5~C60Heterocycle.
Preferably, the amine compounds have formula 4-1 structure shown in any one into formula 4-5:
Wherein, RaAnd RbIt is independent to be selected from hydrogen, substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C6~ C60Aryl, substituted or non-substituted C5~C60Condensed ring radical, substituted or non-substituted C5~C60Heterocycle；
Y is carbon or nitrogen；
RcFor hydrogen, substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C1~C60Alkoxy, replace or Non-substituted C1~C60Ether；
RdFor substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C6~C60Aryl, substitution or non-take The C in generation5~C60Condensed ring radical, substituted or non-substituted C5~C60Heterocycle.
Preferably, the amine compounds have formula 5-1 structure shown in any one into formula 5-5:
Wherein, Ar5For substituted or non-substituted C6~C60Aryl, substituted or non-substituted C5~C60Condensed ring radical, take Generation or non-substituted C5~C60Heterocycle, substituted or non-substituted C6~C60Aryl amine；
Y is carbon or nitrogen；
RaAnd RbIt is independent to be selected from hydrogen, substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C6~C60Virtue Base, substituted or non-substituted C5~C60Condensed ring radical, substituted or non-substituted C5~C60Heterocycle；
RcFor hydrogen, substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C1~C60Alkoxy, replace or Non-substituted C1~C60Ether；
RdFor substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C6~C60Aryl, substitution or non-take The C in generation5~C60Condensed ring radical, substituted or non-substituted C5~C60Heterocycle.
Preferably, the amine compounds have structure shown in formula 6-1:
Wherein, Ar6For substituted or non-substituted C6~C60Arlydene；
Y is carbon or nitrogen；
ReAnd RfIt is independent to be selected from hydrogen, substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C1~C60Alkane Oxygroup, substituted or non-substituted C1~C60Ether.
Preferably, Ra、RbAnd RdIt is independent to be selected from H, methyl, ethyl, the fluoro- ethyl of 2-, 2- cyano-propyl, isopropyl, uncle Butyl, pentyl, heptane base, dodecyl, methoxyl group, ethyoxyl, propoxyl group, isopropoxy, dodecyloxy or formula a-1 are extremely Structure shown in any one of formula a-19；
Wherein, RgFor halogen, amino, cyano, nitro, hydroxyl or sulfydryl；RgAny position on substituent group, Rg? Number is 0~5；At scission of link.
Preferably, Rc、ReAnd RfIt is independent to be selected from H, methyl, ethyl, the fluoro- ethyl of 2-, 2- cyano-propyl, isopropyl, uncle Butyl, pentyl, heptane base, dodecyl, methoxyl group, ethyoxyl, propoxyl group, isopropoxy, dodecyloxy or formula a-20 To structure shown in any one of formula a-30:
Wherein, RhFor halogen, amino, cyano, nitro, hydroxyl or sulfydryl；RgAny position on substituent group, Rh? Number is 0~5；At scission of link.
Preferably, the amine compounds have structure shown in any one of formula 7-1 to formula 7-69:
Wherein, the end group not provided is methyl.
Amine compounds provided by the invention are in luminous efficiency and have preferable performance in terms of the service life.
The present invention provides a kind of preparation methods of amine compounds, comprising:
The compound of the compound of Formulas I structure and Formula II structure is reacted, the amine compounds of formula 1-1 structure are obtained； Or,
The compound of the compound of Formulas I structure and formula III structure is reacted, the amine compounds of formula 1-2 structure are obtained；
Wherein, Ar1For substituted or non-substituted C6~C60Aryl, substituted or non-substituted C5~C60Condensed ring radical, take Generation or non-substituted C5~C60Heterocycle；
Y is carbon or nitrogen；
RaAnd RbIt is independent to be selected from hydrogen, substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C6~C60Virtue Base, substituted or non-substituted C5~C60Condensed ring radical, substituted or non-substituted C5~C60Heterocycle；
RcFor hydrogen, substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C1~C60Alkoxy, replace or Non-substituted C1~C60Ether；
RdFor substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C6~C60Aryl, substitution or non-take The C in generation5~C60Condensed ring radical, substituted or non-substituted C5~C60Heterocycle.
Preferably, the compound of structure shown in the Formula II the preparation method comprises the following steps:
The compound of structure shown in the compound of structure shown in formula IV and Formula V is reacted, structure shown in Formula II is obtained Compound；
Compound shown in the formula III the preparation method comprises the following steps:
The compound of structure shown in the compound of structure shown in Formula IV and Formula VII is reacted, knot shown in formula III is obtained The compound of structure；
Wherein, Y is carbon or nitrogen；
RaAnd RbIt is independent to be selected from hydrogen, substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C6~C60Virtue Base, substituted or non-substituted C5~C60Condensed ring radical, substituted or non-substituted C5~C60Heterocycle；
RcFor hydrogen, substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C1~C60Alkoxy, replace or Non-substituted C1~C60Ether；
RdFor substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C6~C60Aryl, substitution or non-take The C in generation5~C60Condensed ring radical, substituted or non-substituted C5~C60Heterocycle.
The preparation process of aminate provided by the invention is simple, and has in luminous efficiency and in terms of the service life preferable property Energy.
The present invention provides a kind of luminescent devices, including amine compounds described in above-mentioned technical proposal.
Amine compounds provided by the invention can be used for preparing at or it is non-to at luminescent device, this luminescent device has Preferable luminescent properties.
Specific embodiment
The technical scheme in the embodiments of the invention will be clearly and completely described below, it is clear that described implementation Example is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, this field is common Technical staff it is improved or retouching all other example, shall fall within the protection scope of the present invention.
The present invention provides a kind of amine compounds, have structure shown in formula 1-1 or formula 1-2:
Wherein, Ar1For substituted or non-substituted C6~C60Aryl, substituted or non-substituted C5~C60Condensed ring radical, take Generation or non-substituted C5~C60Heterocycle；Preferably substituted or non-substituted C10~C50Aryl, substituted or non-substituted C10 ~C50Condensed ring radical, substituted or non-substituted C10~C50Heterocycle；More preferably substituted or non-substituted C20~C40Virtue Base, substituted or non-substituted C20~C40Condensed ring radical, substituted or non-substituted C20~C40Heterocycle；Most preferably replace or Non-substituted C25~C35Aryl, substituted or non-substituted C25~C35Condensed ring radical, substituted or non-substituted C25~C35It is miscellaneous Ring group.
Y is carbon or nitrogen.
RaAnd RbIt is independent to be selected from hydrogen, substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C6~C60Virtue Base, substituted or non-substituted C5~C60Condensed ring radical, substituted or non-substituted C5~C60Heterocycle；Preferably hydrogen, replace or Non-substituted C5~C50Alkyl, substituted or non-substituted C10~C50Aryl, substituted or non-substituted C10~C50Condensed ring Base, substituted or non-substituted C10~C50Heterocycle；More preferably hydrogen, substituted or non-substituted C10~C40Alkyl, replace or Non-substituted C20~C40Aryl, substituted or non-substituted C20~C40Condensed ring radical, substituted or non-substituted C20~C40It is miscellaneous Ring group；Most preferably hydrogen, substituted or non-substituted C20~C30Alkyl, substituted or non-substituted C25~C35Aryl, replace or Non-substituted C25~C35Condensed ring radical, substituted or non-substituted C25~C35Heterocycle.
RcFor hydrogen, substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C1~C60Alkoxy, replace or Non-substituted C1~C60Ether；Preferably hydrogen, substituted or non-substituted C5~C50Alkyl, substituted or non-substituted C5~C50 Alkoxy, substituted or non-substituted C5~C50Ether, more preferably hydrogen, substituted or non-substituted C10~C40Alkyl, take Generation or non-substituted C10~C40Alkoxy, substituted or non-substituted C10~C40Ether, most preferably hydrogen, substitution or non-take The C in generation20~C30Alkyl, substituted or non-substituted C20~C30Alkoxy, substituted or non-substituted C20~C30Ether.
RdFor substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C6~C60Aryl, substitution or non-take The C in generation5~C60Condensed ring radical, substituted or non-substituted C5~C60Heterocycle, preferably substituted or non-substituted C5~C50's Alkyl, substituted or non-substituted C10~C50Aryl, substituted or non-substituted C10~C50Condensed ring radical, substituted or non-substituted C10~C50Heterocycle；More preferably substituted or non-substituted C10~C40Alkyl, substituted or non-substituted C20~C40Virtue Base, substituted or non-substituted C20~C40Condensed ring radical, substituted or non-substituted C20~C40Heterocycle, most preferably replace or Non-substituted C20~C30Alkyl, substituted or non-substituted C25~C35Aryl, substituted or non-substituted C25~C35Condensed ring Base, substituted or non-substituted C25~C35Heterocycle.
In the present invention, the amine compounds preferably have structure shown in formula 2-1, formula 2-2 or formula 2-3:
In the present invention, the amine compounds preferably have structure shown in formula 3-1, formula 3-2 or formula 3-3:
In the present invention, the amine compounds more preferably have formula 4-1 structure shown in any one into formula 4-5:
In the present invention, the amine compounds more preferably have formula 5-1 structure shown in any one into formula 5-5:
In the present invention, the amine compounds more preferably have structure shown in formula 6-1:
In the present invention, the amine compounds most preferably have structure shown in any one of formula 7-1 to formula 7-69:
In the present invention, the Ar1、Y、Ra、Rb、Rc、RdWith Ar described in above-mentioned technical proposal1、Y、Ra、Rb、Rc、RdUnanimously, Details are not described herein.In the present invention, the Ar2For substituted or non-substituted C6~C60Aryl, substituted or non-substituted C5~ C60Condensed ring radical, substituted or non-substituted C5~C60Heterocycle, substituted or non-substituted C6~C60Aryl amine；Preferably take Generation or non-substituted C10~C50Aryl, substituted or non-substituted C10~C50Condensed ring radical, substituted or non-substituted C10~C50 Heterocycle, substituted or non-substituted C10~C50Aryl amine；More preferably substituted or non-substituted C20~C40Aryl, take Generation or non-substituted C20~C40Condensed ring radical, substituted or non-substituted C20~C40Heterocycle, substituted or non-substituted C20~ C40Aryl amine；Most preferably substituted or non-substituted C25~C35Aryl, substituted or non-substituted C25~C35Condensed ring radical, Substituted or non-substituted C25~C35Heterocycle, substituted or non-substituted C25~C35Aryl amine.In the present invention, the Ar3 For substituted or non-substituted C6~C60Aryl, substituted or non-substituted C5~C60Condensed ring radical, substituted or non-substituted C5~ C60Heterocycle, substituted or non-substituted C6~C60Aryl amine；Preferably substituted or non-substituted C10~C50Aryl, take Generation or non-substituted C10~C50Condensed ring radical, substituted or non-substituted C10~C50Heterocycle, substituted or non-substituted C10~ C50Aryl amine；More preferably substituted or non-substituted C20~C40Aryl, substituted or non-substituted C20~C40Condensed ring radical, Substituted or non-substituted C20~C40Heterocycle, substituted or non-substituted C20~C40Aryl amine；Most preferably replaces or non-take The C in generation25~C35Aryl, substituted or non-substituted C25~C35Condensed ring radical, substituted or non-substituted C25~C35Heterocycle, Substituted or non-substituted C25~C35Aryl amine.In the present invention, the Ar5For substituted or non-substituted C6~C60Aryl, Substituted or non-substituted C5~C60Condensed ring radical, substituted or non-substituted C5~C60Heterocycle, substituted or non-substituted C6~ C60Aryl amine；Preferably substituted or non-substituted C10~C50Aryl, substituted or non-substituted C10~C50Condensed ring radical, take Generation or non-substituted C10~C50Heterocycle, substituted or non-substituted C10~C50Aryl amine, it is more preferably substituted or non-substituted C20~C40Aryl, substituted or non-substituted C20~C40Condensed ring radical, substituted or non-substituted C20~C40Heterocycle, take Generation or non-substituted C20~C40Aryl amine, most preferably substituted or non-substituted C25~C35Aryl, substituted or non-substituted C25~C35Condensed ring radical, substituted or non-substituted C25~C35Heterocycle, substituted or non-substituted C25~C35Aryl amine.? In the present invention, the Ar6For substituted or non-substituted C6~C60Arlydene, preferably substituted or non-substituted C10~C50Asia Aryl, more preferably substituted or non-substituted C20~C40Arlydene, most preferably substituted or non-substituted C25~C35Asia virtue Base.In the present invention, ReAnd RfIt is independent to be selected from hydrogen, substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C1~ C60Alkoxy, substituted or non-substituted C1~C60Ether；Preferably hydrogen, substituted or non-substituted C5~C50Alkyl, take Generation or non-substituted C5~C50Alkoxy, substituted or non-substituted C5~C50Ether；More preferably hydrogen, substituted or non-substituted C10~C40Alkyl, substituted or non-substituted C10~C40Alkoxy, substituted or non-substituted C10~C40Ether；It is optimal It is selected as hydrogen, substituted or non-substituted C20~C30Alkyl, substituted or non-substituted C20~C30Alkoxy, substituted or non-substituted C20~C30Ether.The end group that formula 7-1 is not provided into 7-69 structure is methyl.
In the present invention, Ra、RbAnd RdIndependent preferably H, methyl, ethyl, the fluoro- ethyl of 2-, 2- cyano-propyl, isopropyl Structure shown in base, tert-butyl, pentyl, heptane base, dodecyl or formula a-1 to any one of formula a-19；
Wherein, RgFor halogen, amino, cyano, nitro, hydroxyl or sulfydryl；RgAny position on substituent group, preferably Neighbour is；RgNumber be 0~5 preferably 0,1 or 2；At scission of link.
In the present invention, Rc、ReAnd RfIndependent preferably H, methyl, ethyl, the fluoro- ethyl of 2-, 2- cyano-propyl, isopropyl Base, tert-butyl, pentyl, heptane base, dodecyl, methoxyl group, ethyoxyl, propoxyl group, isopropoxy, dodecyloxy or formula Structure shown in any one of a-20 to formula a-30:
Wherein, RhFor halogen, amino, cyano, nitro, hydroxyl or sulfydryl；RgAny position on substituent group, preferably Ortho position；RhNumber be 0~5, preferably 0,1 or 2；At scission of link.
In the present invention, the amine compounds are preferably the compound of formula 1-2 structure, RcPreferably hydrogen；RdPreferably C1~ C60Alkyl, more preferably C1~C30Alkyl, more preferably C1~C10Alkyl, more preferably C1~C5Alkyl, it is more excellent It is selected as methyl, ethyl or propyl, most preferably methyl；Ar1The C preferably replaced5~C60Condensed ring radical, more preferably replace C10~C20Condensed ring radical.
In the present invention, the amine compounds are preferably the compound of formula 3-3 structure, and Y is preferably carbon, RcPreferably hydrogen；Rd Preferably C1~C60Alkyl, more preferably C1~C30Alkyl, more preferably C1~C10Alkyl, more preferably C1~C5's Alkyl, more preferably methyl, ethyl or propyl, most preferably methyl；Ar3The C preferably replaced5~C60Condensed ring radical, it is more excellent It is selected as the C replaced10~C20Condensed ring radical.
In the present invention, the amine compounds are preferably the compound of formula 4-5 structure, and Y is preferably carbon；RdPreferably C1~ C60Alkyl, more preferably C1~C30Alkyl, more preferably C1~C10Alkyl, more preferably C1~C5Alkyl, it is more excellent It is selected as methyl, ethyl or propyl, most preferably methyl.In the present invention, the amine compounds be preferably formula 7-18, formula 7-19 or The compound of structure shown in formula 7-20.
The present invention provides a kind of preparation methods of amine compounds, comprising:
The compound of the compound of Formulas I structure and Formula II structure is reacted, the amine compounds of formula 1-1 structure are obtained； Or,
The compound of the compound of Formulas I structure and formula III structure is reacted, the amine compounds of formula 1-2 structure are obtained；
Wherein, Ar1For substituted or non-substituted C6~C60Aryl, substituted or non-substituted C5~C60Condensed ring radical, take Generation or non-substituted C5~C60Heterocycle；
Y is carbon or nitrogen；
RaAnd RbIt is independent to be selected from hydrogen, substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C6~C60Virtue Base, substituted or non-substituted C5~C60Condensed ring radical, substituted or non-substituted C5~C60Heterocycle；
RcFor hydrogen, substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C1~C60Alkoxy, replace or Non-substituted C1~C60Ether；
RdFor substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C6~C60Aryl, substitution or non-take The C in generation5~C60Condensed ring radical, substituted or non-substituted C5~C60Heterocycle.
The present invention reacts the compound of the compound of Formulas I structure and Formula II structure, obtains the amination of formula 1-1 structure Close object.In the present invention, the temperature that Formulas I is reacted with Formula II compound is preferably 90 DEG C~110 DEG C, more preferably 95 DEG C~ 105 DEG C, most preferably 100 DEG C.In the present invention, the time that Formulas I is reacted with Formula II compound is preferably 20 hours~30 Hour, more preferably 24 hours~26 hours.In the present invention, it is preferred under stirring conditions by Formulas I and Formula II compound into Row reaction.In the present invention, it is preferred to which Formulas I and Formula II compound are reacted under the protection of nitrogen.In the present invention, it is preferred to The compound of Formulas I and Formula II is reacted in a solvent, the solvent is preferably toluene.In the present invention, it is preferred to three (two Sub- benzyl group acetone) compound of Formulas I and Formula II structure is reacted under the action of two palladiums, tri-tert-butylphosphine and sodium tert-butoxide. In the present invention, the Formulas I and the molar ratio of Formula II structural compounds are preferably (0.1~0.15): (0.8~0.12), more excellent It is selected as (0.11~0.13): (0.9~0.11), most preferably 0.12:0.1.
After reaction, the present invention preferably cools down reaction system for Formulas I and Formula II compound, and water is added to terminate reaction；Will Reaction product filtering, the liquid separation arrived, are dissolved, last column separation obtains aminate after removing solvent therein.In this hair In bright, the method for removing solvent is preferably rotarily dried.In the present invention, the reagent of dissolution is preferably methylene chloride.In this hair In bright, the reagent of the column separation is preferably petroleum ether and methylene chloride, and the volume ratio of the petroleum ether and methylene chloride is excellent It is selected as (2~4): (0.8~1.2), more preferably 3:1.
The present invention does not have special limitation to the source of the compound of the Formulas I structure, ripe using those skilled in the art The method known is prepared.In the present invention, the preparation method of the compound of structure shown in the Formula II is preferred are as follows:
The compound of structure shown in the compound of structure shown in formula IV and Formula V is reacted, structure shown in Formula II is obtained Compound；
In the present invention, the temperature that formula IV is reacted with Formula V compound is preferably 90 DEG C~110 DEG C, more preferably 95 DEG C~105 DEG C, most preferably 100 DEG C.In the present invention, the time that formula IV is reacted with Formula V compound is preferably 20 hours ~30 hours, more preferably 24 hours~26 hours.In the present invention, it is preferred under stirring conditions by formula IV and Formula V chemical combination Object is reacted.In the present invention, it is preferred to which formula IV and Formula V compound are reacted under the protection of nitrogen.In the present invention, It is preferred that in a solvent reacting the compound of formula IV and Formula V, the solvent is preferably toluene.In the present invention, it is preferred to Formula IV and Formula V compound are reacted under the action of three (dibenzylideneacetone) two palladiums, tri-tert-butylphosphine and sodium tert-butoxide.? In the present invention, the molar ratio of the formula IV and Formula V compound is preferably (0.1~0.15): (0.8~0.12), more preferably (0.11~0.13): (0.9~0.11), most preferably 0.12:0.1.
After reaction, the present invention preferably cools down reaction system for formula IV and Formula V compound, and water is added to terminate reaction；Will Reaction product filtering, the liquid separation arrived, are dissolved, last column separation obtains Formula II structure chemical combination after removing solvent therein Object.In the present invention, the method for removing solvent preferably rotarily dries.In the present invention, the reagent of dissolution is preferably dichloromethane Alkane.In the present invention, the reagent of the column separation is preferably petroleum ether and methylene chloride, the petroleum ether and methylene chloride Volume ratio is preferably (2~4): (0.8~1.2), more preferably 3:1.
The present invention does not have special limitation to the source of formula IV and Formula V structural compounds, can be bought and be obtained by market, can also It is prepared according to method well known to those skilled in the art.In the present invention, the system of the compound of structure shown in the formula IV Preparation Method is preferred are as follows:
The compound of structure shown in Formula VIII is subjected to cyclization, obtains the compound of structure shown in formula IV；
In the present invention, the cyclization preferably carries out under the conditions of protecting gas, and the protection gas is preferably nitrogen.? In the present invention, the temperature of the cyclization is preferably 130 DEG C~160 DEG C, more preferably 140 DEG C~150 DEG C.In the present invention In, the time of the cyclization is preferably 15 hours~25 hours, more preferably 18 hours~22 hours.In the present invention, The cyclization preferably carries out in a solvent, and the solvent is preferably toluene.
In the present invention, the cyclization is preferably in 1,8- diazabicylo, 11 carbon -7- alkene, palladium acetate and three tertiary fourths It is carried out in the presence of base phosphine.In the present invention, 1,8- diazabicylo, the 11 carbon -7- alkene, palladium acetate and tri-tert-butylphosphine Molar ratio be preferably (0.08~0.12): (0.002~0.005): (0.02~0.04), more preferably (0.1~0.11): (0.003~0.004): (0.025~0.03).
After the completion of the cyclization, obtained reaction solution is preferably added extraction, liquid separation after water by the present invention, is had what is obtained Machine recrystallizes after being mutually concentrated, and obtains the compound of structure shown in formula IV.In the present invention, the reagent of the recrystallization is toluene.
In the present invention, the preparation method of the compound of structure shown in the Formula VIII is preferred are as follows:
The compound of structure shown in the compound of structure shown in Formula IX and Formula XI is reacted, structure shown in Formula VIII is obtained Compound:
In the present invention, it is carried out in the reaction preferred solvent that the compound of structure shown in preparation formula VIII carries out, it is described molten Agent is preferably tetrahydrofuran, more preferably anhydrous tetrahydro furan.In the present invention, the compound of structure shown in preparation formula VIII into Capable reaction preferably carries out under alkaline condition, and sodium hydride can be added into reaction system.In the present invention, preparation formula VIII institute The temperature for showing the reaction that the compound of structure carries out is preferably 20 DEG C~30 DEG C, more preferably 25 DEG C.In the present invention, preparation formula The time that structural compounds shown in VIII are reacted preferably is stayed overnight, more preferably 15 hours~30 hours, most preferably 20 Hour~25 hours.
In the present invention, the reaction product mistake that the compound of structure shown in preparation formula VIII will preferably obtain after the reaction was completed It filters, dries, dissolves, rushing column, obtain the compound of structure shown in Formula VIII.In the present invention, the method for the drying is preferably It is spin-dried for.In the present invention, the solvent of the dissolution is preferably methylene chloride.In the present invention, the reagent for rushing column is preferably Volume ratio is the petroleum ether and ethyl acetate of 1:5.
In the present invention, the Ar1、Y、Ra、RbWith Ar described in above-mentioned technical proposal1、Y、Ra、RbUnanimously, no longer superfluous herein It states.
The present invention reacts the compound of the compound of Formulas I structure and formula III structure, obtains the amine of formula 1-2 structure Compound.In the present invention, the temperature that Formulas I is reacted with formula III compound is preferably 90 DEG C~110 DEG C, more preferably 95 DEG C~105 DEG C, most preferably 100 DEG C.In the present invention, the time that Formulas I is reacted with formula III compound is preferably 20 hours ~30 hours, more preferably 24 hours~26 hours.In the present invention, it is preferred under stirring conditions by Formulas I and formula III chemical combination Object is reacted.In the present invention, it is preferred to which Formulas I and formula III compound are reacted under the protection of nitrogen.In the present invention In, preferably the compound of Formulas I and formula III is reacted in a solvent, the solvent is preferably toluene.In the present invention, excellent It is selected under the action of three (dibenzylideneacetone) two palladiums, tri-tert-butylphosphine and sodium tert-butoxide and carries out the compound of Formulas I and formula III Reaction.In the present invention, the Formulas I and the molar ratio of formula III structural compounds are preferably (0.1~0.15): (0.8~ 0.12), more preferably (0.11~0.13): (0.9~0.11), most preferably 0.12:0.1.
The present invention does not have special limitation to the source of Formulas I and formula III compound, can be bought and be obtained by market, can also pressed It is prepared according to method well known to those skilled in the art.In the present invention, the preparation method of compound shown in the formula III is excellent It is selected as:
The compound of structure shown in the compound of structure shown in Formula IV and Formula VII is reacted, knot shown in formula III is obtained The compound of structure；
In the present invention, the temperature that Formula IV is reacted with Formula VII compound is preferably 90 DEG C~110 DEG C, more preferably 95 DEG C~105 DEG C, most preferably 100 DEG C.In the present invention, the time that Formula IV is reacted with Formula VII compound is preferably 20 Hour~30 hours, more preferably 24 hours~26 hours.In the present invention, it is preferred under stirring conditions by Formula IV and formula VII compound is reacted.In the present invention, it is preferred to which Formula IV and Formula VII compound are reacted under the protection of nitrogen.? In the present invention, preferably the compound of Formula IV and Formula VII is reacted in a solvent, the solvent is preferably toluene.In this hair In bright, preferably by Formula IV and Formula VII chemical combination under the action of three (dibenzylideneacetone) two palladiums, tri-tert-butylphosphine and sodium tert-butoxide Object is reacted.In the present invention, the Formula IV and the molar ratio of Formula VII compound are preferably (0.1~0.15): (0.8~ 0.12), more preferably (0.11~0.13): (0.9~0.11), most preferably 0.12:0.1.
After reaction, the present invention preferably cools down reaction system for Formula IV and Formula VII compound, and water is added to terminate reaction；It will Obtained reaction product filtering, liquid separation, is dissolved, last column separation obtains formula III structuring after removing solvent therein Close object.In the present invention, the method for removing solvent preferably rotarily dries.In the present invention, the reagent of dissolution is preferably dichloro Methane.In the present invention, the reagent of the column separation is preferably petroleum ether and methylene chloride, the petroleum ether and methylene chloride Volume ratio be preferably (2~4): (0.8~1.2), more preferably 3:1.
The present invention does not have special limitation to the source of the compound of Formula IV and Formula VII structure, can be bought and be obtained by market, It can also be prepared according to method well known to those skilled in the art.In the present invention, the system of the compound of the Formula IV structure Preparation Method is preferred are as follows:
The compound of structure shown in Formula X is subjected to cyclization, obtains the compound of structure shown in Formula IV；
In the present invention, the cyclization preferably carries out under the conditions of protecting gas, and the protection gas is preferably nitrogen.? In the present invention, the temperature of the cyclization is preferably 130 DEG C~160 DEG C, more preferably 140 DEG C~150 DEG C.In the present invention In, the time of the cyclization is preferably 15 hours~25 hours, more preferably 18 hours~22 hours.In the present invention, The cyclization preferably carries out in a solvent, and the solvent is preferably toluene.
In the present invention, the cyclization is preferably in 1,8- diazabicylo, 11 carbon -7- alkene, palladium acetate and three tertiary fourths It is carried out in the presence of base phosphine.In the present invention, 1,8- diazabicylo, the 11 carbon -7- alkene, palladium acetate and tri-tert-butylphosphine Molar ratio be preferably (0.08~0.12): (0.002~0.005): (0.02~0.04), more preferably (0.1~0.11): (0.003~0.004): (0.025~0.03).
After the completion of the cyclization, obtained reaction solution is preferably added extraction, liquid separation after water by the present invention, is had what is obtained Machine recrystallizes after being mutually concentrated, and obtains the compound of structure shown in Formula IV.In the present invention, the reagent of the recrystallization is toluene.
In the present invention, the preparation method of the compound of structure shown in the Formula X is preferred are as follows:
The compound of structure shown in the compound of structure shown in Formula XII and Formula XI is reacted, the change of structure shown in Formula X is obtained Close object:
In the present invention, it is carried out in the reaction preferred solvent that the compound of structure shown in preparation formula X carries out, the solvent is excellent It is selected as tetrahydrofuran, more preferably anhydrous tetrahydro furan.In the present invention, what the compound of structure shown in preparation formula X carried out is anti- It should preferably carry out under alkaline condition, sodium hydride can be added into reaction system.In the present invention, structure shown in preparation formula X The temperature for the reaction that compound carries out is preferably 20 DEG C~30 DEG C, more preferably 25 DEG C.In the present invention, knot shown in preparation formula X The time that structure compound is reacted, more preferably 15 hours~30 hours, most preferably 20 hours~25 is small preferably overnight When.In the present invention, the compound of structure shown in preparation formula X after the reaction was completed preferably by the filtering of obtained reaction product, it is dry, It dissolves, rush column, obtain the compound of structure shown in Formula X.In the present invention, the method for the drying is preferably spin-dried for.In this hair In bright, the solvent of the dissolution is preferably methylene chloride.In the present invention, it is 1:5 that the reagent for rushing column, which is preferably volume ratio, Petroleum ether and ethyl acetate.
In the present invention, the Ar1、Y、RcAnd RdWith Ar described in above-mentioned technical proposal1、Y、RcAnd RdUnanimously, herein no longer It repeats.
The preparation process of aminate provided by the invention is simple, and has in luminous efficiency and in terms of the service life preferable property Energy.
The present invention provides a kind of luminescent devices, including amine compounds described in above-mentioned technical proposal.In the present invention, institute It is consistent with amine compounds described in above-mentioned technical proposal to state amine compounds, details are not described herein.In the present invention, the photophore Part preferably includes cathode, anode and the one or more compound layers being arranged between the cathode and anode, the compound Layer includes amine compounds described in above-mentioned technical proposal.In the present invention, the compound layer can be completely by amine compounds group At can also be made of the mixture of amine compounds and other substances.In the present invention, the compound layer includes hole injection Layer, hole transmission layer had both had hole injection but also with technical ability layer, electronic barrier layer, luminescent layer, the hole barrier of hole transport Layer, electron injecting layer, had both had electron-transport but also with one or more of technical ability layer of electron injection at electron transfer layer. In the present invention, the hole injection layer, hole transmission layer, both had hole injection but also with can in the technical ability layer of hole transport With using conventional hole injecting material, hole transporting material, both have hole injection but also with the substance of hole transport technical ability, It can also be using the substance of electron-transporting material production.
In the present invention, the compound layer preferably includes luminescent layer, and the luminescent layer includes described in above-mentioned technical proposal Amine compounds.In the present invention, the luminescent layer includes in phosphorescence host, fluorescent host, phosphorescence doping and fluorescence doping It is one or more of.In the present invention, fluorescence doping can be can also be used as using the amine compounds as fluorescent host, with And it is adulterated simultaneously as fluorescent host and fluorescence.In the present invention, the luminescent layer can shine for red, yellow or cyan Layer.In the present invention, it when the luminescent layer is cyan luminescent layer, is mixed using above-mentioned amine compounds as cyan main body or cyan It is miscellaneous, high efficiency, high-resolution, high brightness and the luminescent device of long-life can be obtained.
In the present invention, the compound layer preferably includes electron transfer layer, and the electron transfer layer includes above-mentioned technology Amine compounds described in scheme.In the present invention, it is also preferable to include metallic compounds for the electron transfer layer.
In the present invention, the compound layer preferably includes luminescent layer and electron transfer layer, and the luminescent layer and electronics pass For defeated layer containing amine compounds described in above-mentioned technical proposal, the amine compounds in the luminescent layer and electron transfer layer can phase It is same to can also be different.
The present invention does not have special limitation to the preparation method of the luminescent device, and use is well known to those skilled in the art The preparation method of luminescent device is prepared.In the present invention, film vapor deposition, electron beam evaporation, physics gas be can use Mutually the methods of deposition evaporation metal, conductive oxide and their alloy on substrate forms anode；Cathode Preparation method is consistent with anode preparation method；Hole injection layer, hole transport are deposited in order in the cathode surface being prepared Layer, luminescent layer, air barrier and electron transfer layer.In the present invention, prepare hole injection layer, hole transmission layer, luminescent layer, High molecular material solvent engineering can be used during the multilayered structures such as hole blocking layer and electron transfer layer instead of spin-coating (spin-coating), strip forms (tape-casting), scraping blade method (doctor-blading), silk-screen printing (Screen- Printing), the evaporation coating methods such as ink jet printing or thermal imaging (Thermal-Imaging) reduce the preparation of the number of plies.
The amine compounds are prepared luminescent device provided by the invention by adopting the above technical scheme.This photophore Part has preferable luminescent properties, can front shine, back side illuminated or lighting at two sides.
In the present invention, the luminescent device can be used for organic luminescent device (OLED), organic photovoltaic cell (OSC), electricity The philosophical works (e-Paper), Organophotoreceptor (OPC), organic transistor or polycrystalline organic thin film.
Raw materials used following embodiment of the present invention is commercial goods.
0 intermediate A -1 of Examples 1 to 2 to A-20 preparation:
2- isopropyl-phenol 0.1mol is taken, is dissolved in 100mL anhydrous tetrahydro furan, is stirred, precise 0.4mol hydrogenation Sodium is added in reaction flask in batches, should not be too fast, prevents too many bubble from generating, and adds rear solution and yellow is presented, add 1,3- Two bromo- 2- fluorobenzene 0.11mol, will also be added portionwise, and room temperature reaction is overnight.
Obtained reaction product is filtered, solid matter is removed, filtrate is spin-dried for, and methylene chloride dissolution, Guo Zhuyong stone is added Oily ether: ethyl acetate=1:5 (volume ratio) rushes column, obtains the bromo- 2- of 1,3- bis- (2- cumene oxygroup) benzene (intermediate A -1) (0.05mol, y=50%).
The method by adopting the above technical scheme, according to the reaction raw materials provided in table 1 be prepared intermediate A -2 to A-20, table 1 are the reaction mass for preparing intermediate A -1 to A-20.
Table 1 prepares the reaction mass of intermediate A -1 to A-20
21~34 intermediate B -1 of embodiment to B-13 preparation
Under the conditions of nitrogen protection, the bromo- 2- of 1,3- bis- (2- cumene oxygroup) benzene is added in the there-necked flask of 500ml 0.1mmol, 1,8- diazabicylo 11 carbon -7- alkene (DBU) 0.11mmol, palladium acetate 0.003mmol, tri-tert-butylphosphine After 0.025mmol, xylene solution 200ml are added, heating temperature reacts 18 hours, obtains reaction solution to 140 DEG C；Institute It states and is extracted after water is added in reaction solution, liquid separation uses re crystallization from toluene after obtaining organic phase concentration, obtains the bromo- 6- isopropyl of 4- Dibenzo [b, d] furans (intermediate B -1), yield 48%, reaction conversion ratio 100%.
By adopting the above technical scheme prepared by the method to be prepared intermediate B-according to the reaction raw materials provided in table 2 2 to B-13, table 2 is the reaction mass for preparing intermediate B -1 to B-13.
Table 2 prepares the reaction mass of intermediate B -1 to B-13
The preparation of 34~72 intermediate C-1 to C-39 of embodiment
By 4- isopropylamine 0.10mol and sodium tert-butoxide 0.30mol, toluene 400mL is added in reaction flask, stirs 30 points Then clock, nitrogen protection are added 4- bromine dibenzofurans 0.12mol, three (dibenzylideneacetone) two palladium 1.5g, are eventually adding three Tert-butyl phosphine 4g is warming up to 100 DEG C and reacts 24 hours.
Reaction system is cooled down after the reaction was completed, water is added and terminates reaction, filtering by filtrate liquid separation, is spin-dried for toluene, is added A small amount of methylene chloride dissolution is spin-dried for rear product, and using petroleum ether: methylene chloride=3:1 (volume ratio) column separation obtains N- (4- Isopropyl phenyl) dibenzo [b, d] furans -4- amine (intermediate C-1) (0.05mol, y=50%).
The method by adopting the above technical scheme, is prepared intermediate C-1 to C- according to the reaction raw materials that table 3 provides 39,3, table prepare the reaction raw materials of intermediate C-1 to C-39.
Table 3 prepares the reaction mass of intermediate C-1 to C-39
The preparation of 73~98 intermediate D-1 to D-26 of embodiment
(2- methoxyphenyl) boric acid 0.20mol, 9,10- dibromoanthracene 0.10mol and tetra-triphenylphosphine palladium 7.0g is added Into reaction flask, toluene 600mL, aqueous sodium carbonate (2N, 250mL) is added, is carried out instead for 90 DEG C of oil bath under the protection of nitrogen It answers, overnight.
By after reaction system cooling, liquid separation, be spin-dried for toluene, obtained residue is entirely molten with methylene chloride, add The petroleum ether of equivalent crosses silica gel funnel, and with methylene chloride: petroleum ether=1:2 (volume ratio) rinses, until no product point stream Out, filtrate is collected, and is spin-dried for solvent, obtains the bromo- 10- of 9- (2- methoxyphenyl) anthracene (intermediate D-1) (0.081mol, y= 81%).
The method by adopting the above technical scheme, is prepared intermediate D-2 extremely according to the reaction raw materials provided in table 4 D-26, table 4 are the reaction mass for preparing intermediate D-1 to D-26.
Table 4 prepares the reaction mass of intermediate D-1 to D-26
The preparation of 99~167 amine compounds E-1 to E-69 of embodiment
By N- phenyl benzofurans simultaneously [3,2-c] pyridine -6- amine 0.10mol and sodium tert-butoxide 0.30mol, toluene 400mL It is added in reaction flask, stirs 30 minutes, nitrogen protection, bromo- 1, the 1'- biphenyl 0.12mol of 4,4'- bis-, three (two Asias is then added Benzyl group acetone) two palladium 1.5g, it is eventually adding tri-tert-butylphosphine 4g, 100 DEG C is warming up to and reacts 24 hours.
Obtained system is cooled down, water is added and terminates reaction, filtering, the filtrate liquid separation that will be obtained is spin-dried for toluene, is added few Methylene chloride dissolved solid is measured, using petroleum ether: methylene chloride=3:1 (volume ratio) column separation obtains amine compounds E-1 (0.05mol, y=50%).
Nuclear magnetic resonance is carried out to the amine compounds being prepared and Mass Spectrometer Method, testing result are the embodiment of the present invention 99 The amine compounds being prepared have the structure of E-1 in table 5.
The method by adopting the above technical scheme, is prepared amine compounds E-2 according to the reaction raw materials provided in table 5 To E-69, table 5 is the reaction mass for preparing amine compounds E-1 to E-69.
Table 5 prepares the reaction mass of amine compounds E-1 to E-69
The result for the product mass spectra detection that the embodiment of the present invention obtains are as follows:
E-2,754.91；E-4,776.96；E-13,718.80；E-17,778.85；E-20,583.71；E-26, 633.73；E-32,783.95；E-38,876.10；E-40,787.01；E-53,771.90；E-57,833.97；E-60, 864.02；E-66,886.11；E-69,832.96.
The preparation of 168~187 luminescent device of embodiment
It is by Fisher Co., Ltd's coating layer thicknessIto glass substrate be placed in distilled water and clean 2 times, ultrasonic wave Washing 30 minutes, then cleaned repeatedly with distilled water 2 times, ultrasonic washing 10 minutes, after distilled water cleans, using isopropyl Alcohol, acetone, methanol solvate carry out drying after ultrasonic washing in order, and the substrate after drying is transferred to plasma washing machine In, aforesaid substrate washing is sent in evaporator after five minutes.
Hole injection layer 2-TNATA evaporation thickness is successively deposited on cleaned ito transparent electrode is Hole transmission layer a-NPD evaporation thickness isAminate in ADN (9,10- bis- (2- naphthalene) anthracene) and 5% table 6 steams Plating with a thickness ofHole blocking layer and hole transmission layer TPBi evaporation thickness areCathode is that LiF evaporation thickness isAnode is that Al evaporation thickness isAbove process organic matter vaporization plating speed is keptThe vapor deposition speed of LiF Degree isThe evaporation rate of Al isTable 6 is embodiment and the luminescent device that comparative example is prepared Performance test results.
Using 2400 type source measuring unit of KEITHLEY Keithley, CS-2000 spectroradio luminance meter detects embodiment In current density, color, efficiency and the service life of 168~187 luminescent devices being prepared, the results are shown in Table 6.
Comparative example 1
Luminescent device is prepared according to the preparation method of luminescent device described in embodiment 168, difference is, uses DPAP- DPPA replaces amine compounds；
According to method described in above-mentioned technical proposal, current density, the face of the luminescent device that comparative example 1 is prepared are detected Color, efficiency and service life, the results are shown in Table 6.
The performance test results for the luminescent device that 6 embodiment of table and comparative example are prepared
As shown in Table 6, luminescent device, the luminous efficiency of luminescent device and longevity are prepared using amine compounds provided by the invention Life significantly improves.
As seen from the above embodiment, the present invention provides a kind of amine compounds, have structure shown in formula 1-1 or formula 1-2； Wherein, Ar1For substituted or non-substituted C6~C60Aryl, substituted or non-substituted C5~C60Condensed ring radical；Y is carbon or nitrogen；Ra And RbIt is independent to be selected from hydrogen, substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C6~C60Aryl；RcFor hydrogen, Substituted or non-substituted C1~C60Alkyl, substituted or non-substituted C1~C60Alkoxy；RdFor substituted or non-substituted C1~ C60Alkyl, substituted or non-substituted C6~C60Aryl.Amine compounds provided by the invention are in emission wavelength and luminance side Face has preferable performance.
What has been described above is only a preferred embodiment of the present invention, it is noted that for the ordinary skill of the art For personnel, various improvements and modifications may be made without departing from the principle of the present invention, these improvements and modifications It should be regarded as protection scope of the present invention.

Claims (3)

1. a kind of amine compounds, which is characterized in that the amine compounds have structure shown in following any one:
Formula 7-50；
Formula 7-51；Formula 7-52；
Formula 7-53；Formula 7-54；
Formula 7-55；Formula 7-56；
Formula 7-57；Formula 7-58；
Formula 7-59；Formula 7-60；
Formula 7-61；Formula 7-62；
Formula 7-63；Formula 7-64；
Formula 7-65；Formula 7-66；
Formula 7-67；Formula 7-68；
Formula 7-69.
2. a kind of preparation method of amine compounds described in claim 1, comprising:
The compound of the compound of Formulas I structure and Formula II structure is reacted, the amine compounds of formula 1-1 structure are obtained；Or,
The compound of the compound of Formulas I structure and formula III structure is reacted, the amine compounds of formula 1-2 structure are obtained；
Formulas I；Formula II；Formula III；
Formula 1-1；Formula 1-2；
Ar1、X、Ra、Rb、Rc、Rd, Y such as group corresponding in claim 1 particular compound defines.
3. a kind of luminescent device, including amine compounds described in claim 1.
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