CN107459466A - Compound and the organic electronic element for including it - Google Patents

Compound and the organic electronic element for including it Download PDF

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CN107459466A
CN107459466A CN201710407382.3A CN201710407382A CN107459466A CN 107459466 A CN107459466 A CN 107459466A CN 201710407382 A CN201710407382 A CN 201710407382A CN 107459466 A CN107459466 A CN 107459466A
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chemical formula
compound
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CN107459466B (en
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河宰承
洪性佶
李成宰
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LG Chem Ltd
LG Corp
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LG Chemical Co Ltd
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    • 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
    • C07C211/61—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 with at least one of the condensed ring systems formed by three or more rings
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    • 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
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    • 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
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    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
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    • H10K50/14—Carrier transporting layers
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    • H10K50/00—Organic light-emitting devices
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    • H10K50/17—Carrier injection layers
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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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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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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    • H10K85/60—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
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    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Abstract

The present invention relates to compound and include its organic electronic element.The compound of this specification is used for the organic electronic element using organic illuminating element as representative, can reduce the driving voltage of organic electronic element, improves light efficiency, and the life characteristic of element can be improved by the heat endurance of compound.

Description

Compound and the organic electronic element for including it
Technical field
The application is advocated on 06 02nd, the 2016 korean patent application 10-2016- submitted to Koran Office The priority of No. 0069087, its content all belong to this specification.
This specification is related to a kind of compound and includes its organic electronic element.
Background technology
As the representational example of organic electronic element, there is organic illuminating element.In general, organic light emission phenomenon is Refer to, electric energy is changed into the phenomenon of luminous energy using organic substance.Generally have using the organic illuminating element of organic light emission phenomenon Include anode and negative electrode and the structure positioned at the organic matter layer between them.Wherein, in order to improve the effect of organic illuminating element Rate and stability, organic matter layer is often formed by the sandwich construction formed using each different materials, for example, can be by sky The formation such as cave implanted layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer.For such organic illuminating element Structure for, if applying voltage between electrodes, hole is injected into organic matter layer from anode, and electronics injects from negative electrode To organic matter layer, exciton (exciton) is formed when institute's injected holes and electronics meet, when the exciton transits to ground state again Light will be sent.
The lasting new material for requiring exploitation for organic illuminating element as described above.
Prior art literature
Patent document
International Patent Application Publication the 2003-012890th
The content of the invention
This specification provides a kind of compound and includes its organic electronic element.
This specification provides the compound represented by following chemical formula 1 or 2.
[chemical formula 1]
[chemical formula 2]
In above-mentioned chemical formula 1 or 2,
Q is substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring,
L1 is Direct Bonding, substituted or unsubstituted arlydene or substituted or unsubstituted heteroarylidene,
Ar1 is hydrogen, deuterium, halogen group, itrile group, nitro, hydroxyl, carbonyl, ester group, imide, amide groups, substitution or not Substituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy group, take Generation or unsubstituted alkyl sulfenyl (Alkyl thioxy), substituted or unsubstituted artyl sulfo (Aryl thioxy), substituted or unsubstituted alkyl sulfoxide base (Alkyl Sulfoxy), substituted or unsubstituted alkenyl, substituted or unsubstituted silicyl, substituted or unsubstituted boryl, substitution or Unsubstituted oxidation phosphino-, substituted or unsubstituted amido, substituted or unsubstituted arylamine group, substituted or unsubstituted virtue Base or substituted or unsubstituted heteroaryl,
R1 to R6 is same to each other or different to each other, and is each independently hydrogen, deuterium, halogen group, itrile group, nitro, hydroxyl, carbonyl Base, ester group, imide, amide groups, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substitution or unsubstituted Alkoxy, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkyl sulfenyl, substituted or unsubstituted artyl sulfo, Substituted or unsubstituted alkyl sulfoxide base, substituted or unsubstituted alkenyl, substituted or unsubstituted silicyl, substitution do not take The oxidation phosphino- in generation, substituted or unsubstituted amido, substituted or unsubstituted arylamine group, substituted or unsubstituted aryl or The substituted or unsubstituted heteroaryl of person,
N1 is 1 to 5 integer,
N2 is 1 to 5 integer,
N3 is 1 to 4 integer,
N4 is 1 to 3 integer,
N5 is 1 to 3 integer,
N6 is 1 to 4 integer,
When n1 to n6 is more than 2, the structure in more than 2 brackets is same to each other or different to each other.
In addition, this specification provides a kind of organic electronic element, wherein, including：First electrode and above-mentioned first electrode pair The second electrode putting and possess and possesses more than 1 layer of organic matter between above-mentioned first electrode and above-mentioned second electrode Layer, 1 layer of above-claimed cpd contained above in above-mentioned organic matter layer.
Organic electronic using organic illuminating element as representative is used for according to the compound of this specification embodiment Element, can reduce the driving voltage of organic electronic element, improve light efficiency, and can by the heat endurance of compound and Improve the life characteristic of element.
Brief description of the drawings
Fig. 1 shows the organic electronic element 10 of an embodiment according to this specification.
Fig. 2 shows the organic electronic element 11 according to another embodiment of this specification.
Symbol description
10、11：Organic illuminating element
20：Substrate
30：First electrode
40：Luminescent layer
50：Second electrode
60：Hole injection layer
70：Hole transmission layer
80：Electronic barrier layer
90：Electron transfer layer
100：Electron injecting layer
Embodiment
Hereinafter, this specification is described in detail.
This specification provides the compound represented by above-mentioned chemical formula 1.
Compound represented by the above-mentioned chemical formula 1 and 2 aliphatic hydrocarbon ring monocyclic or polycyclic because Q has, therefore improve Triplet energies, make cavity transmission ability good, so as to the effect with the performance for improving element.
The example of substituent in this specification is described below, but is not limited to this.
In this specificationRefer to connecting portion.
Above-mentioned " substitution " this term refers to that the hydrogen atom for being incorporated into the carbon atom of compound is substituted by other substituents, As long as the commutable position of position, i.e. substituent that substituted position hydrogen atom can be substituted just does not limit, when substitution 2 During the individual above, the substituent of more than 2 can be same to each other or different to each other.
In this specification, " substituted or unsubstituted " this term refers to, by selected from deuterium, halogen group, itrile group, nitro, Hydroxyl, carbonyl, ester group, imide, amide groups, alkyl, cycloalkyl, alkoxy, aryloxy group, alkyl sulfenyl, artyl sulfo, alkane Base sulfoxide group, alkenyl, silicyl, boryl, oxidation phosphino-, amido, arylamine group, aryl and to include N, O, S, Se and Si former 1 or more than 2 substituent substitutions in the heteroaryl of more than 1 in son, or by 2 in foregoing illustrative substituent The substituent substitution that substituent above is formed by connecting, or without any substituent.
In this specification, as the example of halogen group, there are fluorine, chlorine, bromine or iodine.
In this specification, the carbon number of carbonyl is not particularly limited, but preferably carbon number is 1 to 50.Specifically, It can be the compound of following structure, but be not limited to this.
In this specification, the carbon number of ester group is not particularly limited, but preferably carbon number is 1 to 50.Specifically, It can be the compound of following structural formula, but be not limited to this.
In this specification, the carbon number of imide is not particularly limited, but preferably carbon number is 1 to 50.Specifically For, it can be the compound of following structure, but be not limited to this.
In this specification, on amino, the nitrogen of amino can be by hydrogen, the straight chain of carbon number 1 to 30, side chain or cyclic alkyl Or the aryl substitution of carbon number 6 to 30.Specifically, it can be the compound of following structural formula, but be not limited to this.
In this specification, alkyl can be straight or branched, and carbon number is not particularly limited, but preferably 1 to 40.Make For concrete example, there are methyl, ethyl, propyl group, n-propyl, isopropyl, butyl, normal-butyl, isobutyl group, the tert-butyl group, sec-butyl, 1- first Base-butyl, 1- Ethyl-butyls, amyl group, n-pentyl, isopentyl, neopentyl, tertiary pentyl, hexyl, n-hexyl, 1- methyl amyls, 2- methyl amyls, 4- methyl -2- amyl groups, 3,3- dimethylbutyls, 2- ethyl-butyls, heptyl, n-heptyl, 1- methylhexyls, ring Phenyl-methyl, cyclohexyl methyl, octyl group, n-octyl, t-octyl, 1- methylheptyls, 2- ethylhexyls, 2- propylpentyls, positive nonyl Base, 2,2- dimethyl heptyl, 1- Ethyl-propyls, 1,1- Dimethyl-propyls, isohesyl, 2- methyl amyls, 4- methylhexyls, 5- Methylhexyl etc., but it is not limited to this.
In this specification, cycloalkyl is not particularly limited, but the preferably cycloalkyl of carbon number 3 to 40, specifically, There are cyclopropyl, cyclobutyl, cyclopenta, 3- methylcyclopentyls, 2,3- dimethylcyclopentyls, cyclohexyl, 3- methylcyclohexyls, 4- first Butylcyclohexyl, 2,3- Dimethylcyclohexyls, 3,4,5- trimethylcyclohexyls, 4- tert-butylcyclohexyls, suberyl, cyclooctyl etc., But it is not limited to this.
In this specification, alkoxy can be straight chain, side chain or ring-type.The carbon number of alkoxy is not particularly limited, But it is preferred that carbon number is 1 to 20.Specifically, it can be methoxyl group, ethyoxyl, positive propoxy, isopropoxy, positive fourth oxygen Base, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyl oxygen, isoamoxy, positive hexyloxy, 3,3- dimethyl Butoxy, 2- ethyl-butoxies, n-octyloxy, positive nonyl epoxide, n-decyloxy, benzyloxy, to methylbenzyloxy etc., it is but and unlimited In this.
In this specification, alkenyl can be straight or branched, and carbon number is not particularly limited, but preferably 2 to 40.Make For concrete example, there are vinyl, 1- acrylic, isopropenyl, 1- cyclobutenyls, 2- cyclobutenyls, 3- cyclobutenyls, 1- pentenyls, 2- penta Alkenyl, 3- pentenyls, 3-methyl-1-butene base, 1,3- butadienyls, pi-allyl, 1- phenylethylene -1- bases, 2- phenylethylenes - Double (hexichol -1- bases) ethene -1- of 1- bases, 2,2- diphenylethlene -1- bases, 2- phenyl -2- (naphthalene -1- bases) ethene -1- bases, 2,2- Base, stilbenyl, styryl etc., but it is not limited to this.
In this specification, silicyl is the substitution being directly connected to comprising Si and above-mentioned Si atoms as free radical Base, and with-SiR104R105R106Represent, R104To R106It is same to each other or different to each other, and can is by hydrogen, deuterium, halogen independently of one another The substituent of at least one composition in group, alkyl, alkenyl, alkoxy, cycloalkyl, aryl and heterocyclic radical.As monosilane The concrete example of base, there are trimethyl silyl, triethylsilyl, t-butyldimethylsilyl, vinyl-dimethyl base Silicyl, propyl-dimethyl silicyl, triphenyl-silyl, diphenylsilyl group, phenyl silyl groups etc., but simultaneously Not limited to this.
In this specification, boryl can be-BR100R101, above-mentioned R100And R101It is same to each other or different to each other, and independently of one another Hydrogen, deuterium, halogen, itrile group, the monocyclic or polycyclic cycloalkyl of substituted or unsubstituted carbon number 3 to 30, substitution can be selected from Or the alkyl of the straight or branched of unsubstituted carbon number 1 to 30, the monocyclic of substituted or unsubstituted carbon number 6 to 30 or Polycyclic aryl and the monocyclic or polycyclic heteroaryl of substituted or unsubstituted carbon number 2 to 30.
In this specification, in the case where aryl is monocyclic aryl, carbon number is not particularly limited, but preferred carbon atom Number is 6 to 50.Specifically, can be phenyl, xenyl, terphenyl, tetrad phenyl etc. as monocyclic aryl, but not It is limited to this.
In the case where above-mentioned aryl is polyaromatic, carbon number is not particularly limited, but preferably carbon number is 10 To 40.Specifically, as polyaromatic, can be naphthyl, anthryl, phenanthryl, pyrenyl, base,Base, fluorenyl etc., but not It is limited to this.
In this specification, above-mentioned fluorenyl can be substituted, and adjacent substituents can be bonded to each other and form ring.
In the case where above-mentioned fluorenyl is substituted, Ke Yiwei Deng, but it is not limited to this.
In this specification, heterocyclic radical is included as the heterocyclic radical of more than 1 in heteroatomic N, O, S, Si and Se, carbon Atomicity is not particularly limited, but preferably carbon number is 6 to 50.As the example of heteroaryl, there are thienyl, furyl, pyrrole Cough up base, imidazole radicals, thiazolyl,Oxazolyl,Di azoly, triazolyl, pyridine radicals, bipyridyl, pyrimidine radicals, triazine radical, three Oxazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolyl, quinoxalinyl, phthalazinyl, Pyridopyrimidine base, pyrido Pyrazinyl, pyrazine and pyrazinyl, isoquinolyl, indyl, carbazyl, benzoOxazolyl, benzimidazolyl, benzothiazolyl, Benzo carbazole base, benzothienyl, dibenzothiophenes base, benzofuranyl, phenanthroline (phenanthroline) base, thiazole It is base, differentOxazolyl,Di azoly, thiadiazolyl group, benzothiazolyl and dibenzofuran group etc., but it is not limited to this.
In this specification, amido refers to amino (- NH2) the 1 valency amine that is substituted by other substituents of at least one hydrogen atom, And with-NR107R108Represent, R107And R108It is same to each other or different to each other, and can is by hydrogen, deuterium, halogen group, alkane independently of one another Substituent (wherein, the R of at least one composition in base, alkenyl, alkoxy, cycloalkyl, aryl and heterocyclic radical107And R108In At least one is not hydrogen).For example ,-NH can be selected from2, monoalkyl amido, dialkyl amino, N- alkylaryls amido, single aryl Amido, diaryl amido, N- aryl heteroaryls amido, N- miscellaneous alkyl aryls amido, single heteroaryl amido and di (hetero) arylamine group, Carbon number is not particularly limited, but preferably 1 to 30.As the concrete example of amido, there are methylamino, dimethyl amido, second Base amido, diethyl amido, phenyl amido, naphthyl amido, xenyl amido, anthryl amido, 9- methyl-anthryl amido, hexichol Base amido, xylyl amido, N- phenyltoluene bases amido, triphenyl amido, N- phenylbiphenylyls amido, N- phenyl naphthyl amines Base, N- xenyl naphthyls amido, N- naphthyl fluorenyls amido, N- phenyl phenanthryl amido, N- xenyl phenanthryl amido, N- phenylfluorenyls Amido, N- phenyl terphenyls amido, N- phenanthryl fluorenyls amido, N- xenyl fluorenyl amidos etc., but it is not limited to this.
In this specification, as oxidation phosphino-, specifically, there are diphenyl phosphine oxide base, dinaphthyl oxidation phosphino- etc., but It is not limited to this.
In this specification, aryloxy group, artyl sulfo (Aryl thioxy) in aryl with it is above-mentioned The illustration of aryl is identical.Specifically, as aryloxy group, have phenoxy group, to toloxyl, a toloxyl, 3,5- dimethyl- Phenoxy group, 2,4,6- trimethylbenzenes epoxide, to tert-butyl benzene epoxide, 3- biphenylyloxies, 4- biphenylyloxies, 1- naphthoxys, 2- naphthalenes Epoxide, 4- methyl isophthalic acids-naphthoxy, 5- methyl -2- naphthoxys, 1- anthracenes epoxide, 2- anthracenes epoxide, 9- anthracenes epoxide, 1- phenanthrene epoxide, 3- are luxuriant and rich with fragrance Epoxide, 9- phenanthrene epoxides etc., as artyl sulfo, there are phenylsulfartyl, 2- aminomethyl phenyls sulfenyl, 4- tert-butyl-phenyl sulfenyls etc., but Not limited to this.
In this specification, as the example of arylamine group, substituted or unsubstituted monoarylamine base, substitution or unsubstituted Diaryl amido or substituted or unsubstituted triaryl amido.Aryl in above-mentioned arylamine group can be monocyclic aryl, It can also be polyaromatic.Arylamine group comprising more than 2 above-mentioned aryl can include monocyclic aryl, polyaromatic or same When include monocyclic aryl and polyaromatic.For example, the aryl in above-mentioned arylamine group can select from the illustration of above-mentioned aryl. As the concrete example of arylamine group, there are phenyl amine, naphthylamine, xenylamine, anthryl amine, 3- methylphenyls amine, 4- methyl-naphthalene Base amine, 2- Methvl-biphenyls amine, 9- methyl-anthryl amine, diphenyl amido, phenyl napthyl amido, xylyl amido, phenyl Tolyl amido, carbazole and triphenyl amido etc., but it is not limited to this.
In this specification, arlydene refers to, has the group at two basic change position, i.e. divalent group on aryl.They are removed It is respectively beyond divalent group, the explanation of applicable above-mentioned aryl.
In this specification, heteroarylidene refers to, has the group at two basic change position, i.e. divalent group on heteroaryl.It In addition to being respectively divalent group, the explanation of applicable above-mentioned heteroaryl.
In one embodiment of this specification, Q is substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring.
In one embodiment of this specification, Q is substituted or unsubstituted pentamethylene, substituted or unsubstituted hexamethylene Alkane, substituted or unsubstituted cycloheptane, substituted or unsubstituted cyclooctane, substituted or unsubstituted bicycloheptane, substitution or not Substituted tricycloheptane or substituted or unsubstituted decahydronaphthalenes.
In one embodiment of this specification, Q is by the substituted or unsubstituted pentamethylene of alkyl or aryl.
In one embodiment of this specification, Q is to be substituted or do not taken by methyl, ethyl, isopropyl, the tert-butyl group or phenyl The pentamethylene in generation.
In one embodiment of this specification, Q is pentamethylene.
In one embodiment of this specification, Q is by the substituted or unsubstituted hexamethylene of alkyl or aryl.
In one embodiment of this specification, Q is to be substituted or do not taken by methyl, ethyl, isopropyl, the tert-butyl group or phenyl The hexamethylene in generation.
In one embodiment of this specification, Q is hexamethylene.
In one embodiment of this specification, Q is by the substituted or unsubstituted cycloheptane of alkyl or aryl.
In one embodiment of this specification, Q is to be substituted or do not taken by methyl, ethyl, isopropyl, the tert-butyl group or phenyl The cycloheptane in generation.
In one embodiment of this specification, Q is cycloheptane.
In one embodiment of this specification, Q is by the substituted or unsubstituted cyclooctane of alkyl or aryl.
In one embodiment of this specification, Q is to be substituted or do not taken by methyl, ethyl, isopropyl, the tert-butyl group or phenyl The cyclooctane in generation.
In one embodiment of this specification, Q is cyclooctane.
In one embodiment of this specification, Q is by the substituted or unsubstituted bicycloheptane of alkyl or aryl.
In one embodiment of this specification, Q is to be substituted or do not taken by methyl, ethyl, isopropyl, the tert-butyl group or phenyl The bicycloheptane in generation.
In one embodiment of this specification, Q is bicycloheptane.
In one embodiment of this specification, Q is by the substituted or unsubstituted tricycloheptane of alkyl or aryl.
In one embodiment of this specification, Q is to be substituted or do not taken by methyl, ethyl, isopropyl, the tert-butyl group or phenyl The tricycloheptane in generation.
In one embodiment of this specification, Q is tricycloheptane.
In one embodiment of this specification, Q is by the substituted or unsubstituted decahydronaphthalenes of alkyl or aryl.
In one embodiment of this specification, Q is to be substituted or do not taken by methyl, ethyl, isopropyl, the tert-butyl group or phenyl The decahydronaphthalenes in generation.
In one embodiment of this specification, Q is decahydronaphthalenes.
In one embodiment of this specification, Q can be any one in following structural formula.
In one embodiment of this specification, L1 be Direct Bonding, substituted or unsubstituted arlydene or substitution or Unsubstituted heteroarylidene.
In one embodiment of this specification, L1 is Direct Bonding.
In one embodiment of this specification, L1 is substituted or unsubstituted phenylene, substituted or unsubstituted sub- connection Phenyl, substituted or unsubstituted naphthylene, substituted or unsubstituted sub- terphenyl or substituted or unsubstituted fluorenylidene (fluorenylene group)。
In one embodiment of this specification, L1 is by methyl, ethyl or the substituted or unsubstituted divalent Asia fluorenes of the tert-butyl group Base.
In one embodiment of this specification, L1 is phenylene, biphenylene, naphthylene, sub- terphenyl or sub- fluorenes Base.
In one embodiment of this specification, L1 is substituted or unsubstituted divalent dibenzofuran group, substitution or not taken The divalent dibenzothiophenes base in generation or substituted or unsubstituted divalent carbazyl.
In one embodiment of this specification, L1 is is substituted by phenyl or unsubstituted divalent carbazyl.
In one embodiment of this specification, L1 is divalent dibenzofuran group, divalent dibenzothiophenes base or divalent click Oxazolyl.
In one embodiment of this specification, L1 is can be selected from any one in following structural formula.
In one embodiment of this specification, Ar1 is hydrogen, deuterium, halogen group, itrile group, nitro, hydroxyl, carbonyl, ester Base, imide, amide groups, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alcoxyl Base, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkyl sulfenyl, substituted or unsubstituted artyl sulfo, substitution or Unsubstituted alkyl sulfoxide base, substituted or unsubstituted alkenyl, substituted or unsubstituted silicyl, substituted or unsubstituted boron Base, substituted or unsubstituted oxidation phosphino-, substituted or unsubstituted amido, substituted or unsubstituted arylamine group, substitution or not Substituted aryl or substituted or unsubstituted heteroaryl.
In one embodiment of this specification, Ar1 is the substituted or unsubstituted aryl of carbon number 6 to 50.
In one embodiment of this specification, Ar1 is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl Base, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrad phenyl, substituted or unsubstituted naphthyl, substitution or not Substituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenyl, substituted or unsubstituted pyrenyl, substitution or It is unsubstituted base, substituted or unsubstitutedBase or substituted or unsubstituted fluorenyl.
In one embodiment of this specification, Ar1 is phenyl, xenyl, terphenyl, tetrad phenyl, naphthyl, anthracene Base, phenanthryl, triphenyl, pyrenyl, base,Base or fluorenyl.
In one embodiment of this specification, Ar1 is the substituted or unsubstituted heteroaryl of carbon number 6 to 50.
In one embodiment of this specification, Ar1 is for substituted or unsubstituted dibenzofuran group or substitution or not Substituted dibenzothiophenes base.
In one embodiment of this specification, Ar1 is is substituted by phenyl or unsubstituted dibenzofuran group.
In one embodiment of this specification, Ar1 is is substituted by phenyl or unsubstituted dibenzothiophenes base.
In one embodiment of this specification, Ar1 is dibenzofuran group or dibenzothiophenes base.
In one embodiment of this specification, Ar1 is any one in following structural formula.
In one embodiment of this specification, above-mentioned R ' and R " is same to each other or different to each other, and be each independently hydrogen, Deuterium, halogen group, itrile group, nitro, hydroxyl, carbonyl, ester group, imide, amide groups, substituted or unsubstituted alkyl, substitution Or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkyl Sulfenyl, substituted or unsubstituted artyl sulfo, substituted or unsubstituted alkyl sulfoxide base, substituted or unsubstituted alkenyl, substitution Or unsubstituted silicyl, substituted or unsubstituted oxidation phosphino-, substituted or unsubstituted amido, substituted or unsubstituted virtue Base amido, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl.
In one embodiment of this specification, R1 to R6 is same to each other or different to each other, and is each independently hydrogen, deuterium, halogen Plain group, itrile group, nitro, hydroxyl, carbonyl, ester group, imide, amide groups, substituted or unsubstituted alkyl, substitution do not take The cycloalkyl in generation, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkyl sulfenyl, Substituted or unsubstituted artyl sulfo, substituted or unsubstituted alkyl sulfoxide base, substituted or unsubstituted alkenyl, substitution do not take The silicyl in generation, substituted or unsubstituted oxidation phosphino-, substituted or unsubstituted amido, substituted or unsubstituted arylamine Base, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl.
In one embodiment of this specification, R1 to R6 is same to each other or different to each other, and is each independently hydrogen.
In one embodiment of this specification, above-mentioned chemical formula 1 can be represented by following chemical formula 3 to 6.
[chemical formula 3]
[chemical formula 4]
[chemical formula 5]
[chemical formula 6]
In above-mentioned chemical formula 3 to 6,
Definition on Q, L1, Ar1, R1 to R6 and n1 to n6 is identical with the definition in above-mentioned chemical formula 1.
In one embodiment of this specification, above-mentioned chemical formula 2 can be represented by following chemical formula 7 to 10.
[chemical formula 7]
[chemical formula 8]
[chemical formula 9]
[chemical formula 10]
In above-mentioned chemical formula 7 to 10,
Definition on Q, L1, Ar1, R1 to R6 and n1 to n6 is identical with the definition in above-mentioned chemical formula 2.
In one embodiment of this specification, above-mentioned chemical formula 1 is any one in following compounds.
In one embodiment of this specification, above-mentioned chemical formula 2 can be any one in following compounds.
Manufacture method described later can be utilized to manufacture according to the compound of this specification embodiment.It is described later In Production Example, although describing representational example, substituent can be added or deleted as needed, substitution can also be changed The position of base.In addition, it is based on technology as known in the art, thus it is possible to vary initial substance, reactive material, reaction condition etc..
In addition, this specification provides the organic electronic element for including above-mentioned compound.
In one embodiment of this specification, there is provided a kind of organic illuminating element, wherein, including：First electrode, with it is upper State that first electrode is opposed and the second electrode that possesses；And possesses 1 layer between above-mentioned first electrode and above-mentioned second electrode More than organic matter layer, 1 layer of above-claimed cpd contained above in above-mentioned organic matter layer.
In this specification, when point out a certain component be located at another component " on " when, its not only include a certain component with it is another The situation of component contact, in addition to other components between two components be present.
In this specification, when pointing out a certain inscape of certain a part of "comprising", as long as no especially opposite record, Then mean further include other inscapes, rather than other inscapes are excluded.
The organic matter layer of the organic illuminating element of this specification can be formed by single layer structure, can also be by being laminated with 2 layers The sandwich construction of above organic matter layer is formed.For example, the representational example of the organic electronic element as the present invention, You Jifa Optical element, which can have, includes hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer, electronic blocking The structure as organic matter layer such as layer, hole blocking layer.But the structure of organic electronic element is not limited to this, can include The less organic layer of quantity.
According to this specification embodiment, above-mentioned organic illuminating element can be selected from Phosphorescent element, organic Solar cell, Organophotoreceptor (OPC) and organic transistor.
In one embodiment of this specification, above-mentioned organic matter layer includes luminescent layer, and above-mentioned luminescent layer includes above-mentionedization Compound.
In one embodiment of this specification, above-mentioned organic matter layer includes hole injection layer or hole transmission layer, above-mentioned Hole injection layer or hole transmission layer include above-claimed cpd.
In one embodiment of this specification, above-mentioned organic matter layer includes electron transfer layer or electron injecting layer, above-mentioned Electron transfer layer or electron injecting layer include above-claimed cpd.
In one embodiment of this specification, above-mentioned organic matter layer includes electronic barrier layer, above-mentioned electronic barrier layer bag Containing above-claimed cpd.
In one embodiment of this specification, above-mentioned organic illuminating element can be included further to be injected selected from hole 1 layer in layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer, hole blocking layer and electronic barrier layer or 2 layers More than.
In one embodiment of this specification, above-mentioned organic illuminating element includes first electrode and above-mentioned first electrode It is opposed and possess second electrode, possess the luminescent layer between above-mentioned first electrode and above-mentioned second electrode and possess More than 2 layers of organic matter between above-mentioned luminescent layer and above-mentioned first electrode or between above-mentioned luminescent layer and above-mentioned second electrode Layer, at least one layer in above-mentioned more than 2 layers of organic matter layer includes above-claimed cpd.In one embodiment of this specification, Above-mentioned more than 2 layers of organic matter layer from electron transfer layer, electron injecting layer while can carry out electric transmission and electron injection More than 2 layers are selected in layer and hole blocking layer.
In one embodiment of this specification, above-mentioned organic matter layer includes more than 2 layers of electron transfer layer, above-mentioned 2 layers At least one layer in electron transfer layer above includes above-claimed cpd.Specifically, in an embodiment of this specification, Can be that 1 layer in above-mentioned more than 2 layers of electron transfer layer includes above-claimed cpd or above-mentioned more than 2 layers of electronics Transport layer includes above-claimed cpd respectively.
In addition, in an embodiment of this specification, above-mentioned more than 2 layers of electron transfer layer includes above-mentioned chemical combination respectively In the case of thing, the other materials beyond above-claimed cpd can be same to each other or different to each other.
In one embodiment of this specification, above-mentioned organic matter layer except the organic matter layer comprising above-claimed cpd with Outside, further comprising hole injection layer or hole transmission layer, the hole injection layer or hole transmission layer include containing arylamine group, The compound of carbazyl or benzo carbazole base.
In another embodiment, organic illuminating element can be sequentially laminated with substrate anode, more than 1 layer have The organic illuminating element of machine nitride layer and the structure of negative electrode (standard type (normal type)).
In the case that the organic matter layer of compound comprising above-mentioned chemical formula 1 is electron transfer layer, above-mentioned electron transfer layer N-type dopant can further be included.Above-mentioned n-type dopant can use n-type dopant known in the art, such as can make With metal or metal complex.According to an example, the electron transfer layer of the compound comprising above-mentioned chemical formula 1 can be further Include LiQ.
In one embodiment of this specification, above-mentioned organic illuminating element includes first electrode and above-mentioned first electrode It is opposed and possess second electrode, possess the luminescent layer between above-mentioned first electrode and above-mentioned second electrode and possess More than 2 layers of organic matter between above-mentioned luminescent layer and above-mentioned first electrode or between above-mentioned luminescent layer and above-mentioned second electrode Layer, at least one layer in above-mentioned more than 2 layers of organic matter layer includes above-claimed cpd.In one embodiment of this specification, Above-mentioned more than 2 layers of organic matter layer from hole transmission layer, hole injection layer while can carry out hole transport and electron injection More than 2 layers are selected in layer and hole blocking layer.
In one embodiment of this specification, above-mentioned organic matter layer can include the stepped construction of p-type doped layer.
In this specification, p-type doped layer refers to the layer doped with p-type dopant.P-type dopant is to instigate main substance to have There is the material of p-type semiconductor characteristic.P-type semiconductor characteristic refers to, according to HOMO (highest occupied molecular orbital(HOMO), highest Occupied molecular orbital) energy level reception hole injects or the characteristic of transporting holes, the i.e. conductivity in hole are big Material characteristic.
In one embodiment of this specification, noted in the organic matter layer of the compound comprising above-mentioned chemical formula 1 for hole In the case of entering layer, above-mentioned hole injection layer can be adulterated by p-type dopant.
In one embodiment of this specification, above-mentioned p-type dopant can utilize material as known in the art, above-mentioned The concentration of doped layer can be 0.01wt% to 50wt%.
In one embodiment of this specification, it can be included between luminescent layer and anode by p-type dopant doping Hole transmission layer.According to an example, luminescent layer is may be embodied in containing compound 1 and doped with the hole transmission layer of dopant Between anode.More specifically, it may be embodied in hole regulation containing compound 1 and doped with the hole transmission layer of dopant Between layer and hole injection layer.
In another embodiment, organic illuminating element can be sequentially laminated with substrate negative electrode, more than 1 layer have The organic illuminating element of machine nitride layer and the reverse structure of anode (inversion type (inverted type)).
For example, the structure of the organic illuminating element of this specification can have the structure shown in Fig. 1 and Fig. 2, but not It is only limitted to this.
Exemplified with being sequentially laminated with the organic of first electrode 30, luminescent layer 40 and second electrode 50 on the base plate 20 in Fig. 1 The structure of light-emitting component 10.Above-mentioned Fig. 1 is the exemplary architecture of the organic illuminating element of an embodiment of this specification, can Further to include other organic matter layers.
In Fig. 2 exemplified be sequentially laminated with the base plate 20 first electrode 30, hole injection layer 60, hole transmission layer 70, Electronic barrier layer 80, luminescent layer 40, electron transfer layer 90, the organic illuminating element of electron injecting layer 100 and second electrode 50 Structure.Above-mentioned Fig. 2 is according to the exemplary architecture of the embodiment of this specification, can further include other organic matter layers.
The organic illuminating element of this specification is except the compound, i.e. of 1 layer of this specification contained above in organic matter layer Beyond above-claimed cpd, it can be manufactured using material known in the art and method.
In the case that above-mentioned organic illuminating element includes multilayer organic matter layer, above-mentioned organic matter layer can by same substance or Different material is formed.
The organic illuminating element of this specification is except 1 layer of above-claimed cpd, i.e. above-mentionedization contained above in organic matter layer Beyond compound represented by formula 1, it can be manufactured using material known in the art and method.
For example, the organic illuminating element of this specification can be by stacking gradually first electrode, organic matter layer on substrate Manufactured with second electrode.At this point it is possible to manufacture as follows：Utilize sputtering method (sputtering) or electron-beam vapor deposition method (e- Beam evaporation) etc PVD (physical vapor deposition method, physical Vapor Deposition), steamed on substrate Plate metal or conductive metal oxide or their alloy and form anode, formed on the anode and noted comprising hole Enter the organic matter layer of layer, hole transmission layer, luminescent layer and electron transfer layer, then evaporation can be used as negative electrode on the organic matter layer Material.In addition to such method, can also on substrate successively evaporation cathode material, organic matter layer, anode material come Manufacture organic illuminating element.
In addition, the compound on above-mentioned chemical formula 1, when manufacturing organic illuminating element, can not only utilize vacuum to steam Plating method, organic matter layer can also be formed using solution coating method.Wherein, so-called solution coating method refers to, spin-coating method, dip-coating Method, knife coating, ink jet printing method, silk screen print method, spray-on process, rolling method etc., but it is not limited only to this.
In addition to method as described above, can also on substrate evaporation cathode material, organic matter layer, anode material successively And manufacture organic illuminating element (International Patent Application Publication the 2003-012890th).But manufacture method is not limited to this.
In one embodiment of this specification, above-mentioned first electrode is anode, and above-mentioned second electrode is negative electrode.
In another embodiment, above-mentioned first electrode is negative electrode, and above-mentioned second electrode is anode.
As above-mentioned anode material, generally for enabling hole successfully to be injected to organic matter layer, preferably work function Big material.As the concrete example of workable anode material in the present invention, have the metals such as vanadium, chromium, copper, zinc, gold or they Alloy；The metal oxides such as zinc oxide, indium oxide, tin indium oxide (ITO), indium zinc oxide (IZO)；ZnO:Al or SnO2:Sb etc. The combination of metal and oxide；Poly- (3 methyl thiophene), poly- [3,4- (ethylidene -1,2- dioxies) thiophene] (PEDOT), polypyrrole And electroconductive polymer such as polyaniline etc., but it is not limited only to this.
As above-mentioned cathode substance, generally for making electronics easily be injected to organic matter layer, preferably work function is small Material.As the concrete example of cathode substance, have the metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminium, silver, tin and lead or it Alloy；LiF/Al or LiO2Sandwich construction material such as/Al etc., but it is not limited only to this.
Above-mentioned hole injection layer is the layer in the hole that injection carrys out self-electrode, is preferably followingization as hole injecting material Compound：Possess the ability of transporting holes, there is the hole injection effect from anode, for the excellent of luminescent layer or luminescent material Hole injection effect, prevent in luminescent layer caused exciton to be migrated to electron injecting layer or electron injection material, and thin Film Forming ability is excellent.It is preferred that HOMO (highest occupied molecular orbital(HOMO), the highest occupied of hole injecting material Molecular orbital) between the work function of anode material and the HOMO of surrounding organic matter layer.As hole infusion The concrete example of matter, there are metalloporphyrin (porphyrin), Oligopoly thiophene, aryl amine system organic matter, the azepine benzophenanthrene system of six nitrile six to have Machine thing, quinacridone (quinacridone) are that organic matter, (perylene) are organic matter, anthraquinone and polyaniline and polythiophene It is electroconductive polymer etc., but is not limited only to this.
Above-mentioned hole transmission layer is to receive the hole from hole injection layer and by the layer of hole transport to luminescent layer, as Hole transporting material, it is that can receive the hole from anode or hole injection layer and transfer them to the material of luminescent layer, it is empty Mobility big material in cave is suitable.As concrete example, there are aryl amine system organic matter, electroconductive polymer and deposit simultaneously In block copolymer of conjugate moiety and non-conjugated portion etc., but it is not limited only to this.
Above-mentioned electronic barrier layer is to prevent from entering electron injecting layer from hole injection layer injected holes by luminescent layer And the life-span of element and the layer of efficiency can be improved, if necessary, known material can be used to be formed and noted in luminescent layer and electronics Enter the suitable part between layer.
It is that can receive the sky from hole transmission layer and electron transfer layer respectively as the luminescent substance of above-mentioned luminescent layer Cave and electronics and make its with reference to and send the material of the light of visible region, it is preferably high for the quantum efficiency of fluorescence or phosphorescence Material.As concrete example, there is 8-hydroxyquinoline aluminum complex (Alq3)；Carbazole based compound；Two is polystyrene-based (dimerized styryl) compound；BAlq；10- hydroxy benzo quinoline metal compounds；BenzoAzoles, benzothiazole and Benzimidazole based compound；Poly- (to phenylene vinylidene) (PPV) is macromolecule；Loop coil (spiro) compound；It is polyfluorene, red Glimmering alkene etc., but it is not limited only to this.
Above-mentioned luminescent layer can include material of main part and dopant material.Material of main part has aromatic fused ring derivative or contained Heterocyclic compound etc..Specifically, as aromatic fused ring derivative, there are anthracene derivant, pyrene derivatives, naphthalene derivatives and five Benzene derivative, phenanthrene compound, fluoranthene compound etc., as nitrogen-containing heterocgcies, there are carbazole derivates, dibenzofurans to derive Thing, ladder type furan compoundPyrimidine derivatives etc., but it is not limited to this.
As above-mentioned dopant material, there are aromatic amine derivative, styrylamine compounds, boron complexes, fluoranthene Compound, metal complex etc..Specifically, as aromatic amine derivative, there is substituted or unsubstituted arylamine group Aromatic fused ring derivative, have the pyrene with arylamine group, anthracene,Two indeno pyrenes (Periflanthene) etc., as benzene second Alkenyl amines, be that substitution has the compound of at least one aryl vinyl on substituted or unsubstituted arylamine, by selected from 1 in aryl, silicyl, alkyl, cycloalkyl and arylamine group or more than 2 substituent substitutions or unsubstituted.It is specific and Speech, has styryl amine, styryl diamines, styryl triamine, styryl tetramine etc., but be not limited to this.In addition, make For metal complex, there are complex of iridium, platinum complex etc., but be not limited to this.
Above-mentioned electron transfer layer is to receive electronics and by the layer of electric transmission to luminescent layer from electron injecting layer, as electronics Transport materials, it is that can receive electronics well from negative electrode and transfer them to the material of luminescent layer, the big thing of electron mobility Matter is suitable.As concrete example, there are the Al complexs of 8-hydroxyquinoline, comprising Alq3Complex, organic free radical chemical combination Thing, flavonol-metal complex etc., but it is not limited only to this.Electron transfer layer can be such as that used in conventional art Sample and the cathode substance of any desired are used together.Particularly, the example of suitable cathode substance is with low work function and companion With aluminium lamination or the common material of silver layer.Specially caesium, barium, calcium, ytterbium and samarium, in the case of each material, along with aluminium lamination or Silver layer.
Above-mentioned electron injecting layer be injection come self-electrode electronics layer, preferably following compound：With transmission electronics Ability, have the electron injection effect from negative electrode, the excellent electron injection effect for luminescent layer or luminescent material, prevent Only caused exciton migrates to hole injection layer in luminescent layer, and film Forming ability is excellent.Specifically, have Fluorenone, Anthraquinone bismethane (Anthraquinodimethane), diphenoquinone, thiopyrandioxide,Azoles,Diazole, triazole, imidazoles, Tetrabasic carboxylic acid, fluorenylidene-methane, anthrone etc. and their derivative, metal complex and nitrogenous 5 membered ring derivatives etc., but simultaneously Not limited to this.
As above-mentioned metal complex, have 8-hydroxyquinoline lithium, double (8-hydroxyquinoline) zinc, double (8-hydroxyquinoline) copper, It is double (8-hydroxyquinoline) manganese, three (8-hydroxyquinoline) aluminium, three (2- methyl -8-hydroxyquinoline) aluminium, three (8-hydroxyquinoline) galliums, double (10- hydroxy benzos [h] quinoline) beryllium, double (10- hydroxy benzos [h] quinoline) zinc, double (2- methyl -8- quinoline) gallium chlorides, double (2- Methyl -8- quinoline) (orthoresol) gallium, double (2- methyl -8- quinoline) (1- naphthols) aluminium, double (2- methyl -8- quinoline) (beta naphthals) Gallium etc., but it is not limited to this.
Above-mentioned hole regulating course is to be efficiently received hole from hole transmission layer, plays the effect of regulation hole mobility, So as to play the effect that the amount to the hole of luminescent layer is transmitted in regulation.Furthermore, it is possible to performing simultaneously does not make from luminescent layer supply ELECTRONIC COVER as electron transition to hole transmission layer acts on.Its luminescent layer make hole it is balanced with electronics maximization and energy Enough increase luminous efficiency, the life-span of element can be improved by the electronic stability of hole regulating course, this technology can be used Known material in field.
Above-mentioned hole blocking layer is the layer for preventing hole from reaching negative electrode, can typically be utilized and hole injection layer identical bar Part is formed.Specifically, haveOxadiazole derivative or triazole derivative, phenanthroline derivative, BCP, aluminum complex (aluminum complex) etc., but it is not limited to this.
According to the organic illuminating element of this specification used in material, can be top emission type, bottom-emission Type or bidirectional luminescence type.
In one embodiment of this specification, in addition to organic illuminating element can also in organic solar batteries or The compound represented by above-mentioned chemical formula 1 is included in organic transistor.
Similar principle is applied to when can be by with applied to organic illuminating element according to the compound of this specification Organic electronic element with Phosphorescent element, organic solar batteries, Organophotoreceptor, organic transistor etc. for representative.
Hereinafter, in order to illustrate this specification, embodiment and comparative example etc. are enumerated to describe in detail.However, this explanation The embodiment and comparative example of book can be changed to various other forms, and the scope of this specification should not be construed as limited to following The embodiment and comparative example of detailed description.The embodiment and comparative example of this specification are to more completely be said to those skilled in the art Bright this specification and provide.
<Production Example>
<Production Example 1>- A1 to A4, B1 and B2 synthesis
(1) A1 synthesis
The bromo- 9H- fluorenes (100g, 407.96mmol) of 2- and 50wt% sodium hydrate aqueous solutions (70g, 897.51mol) are added After adding to dimethyl sulfoxide (DMSO) (1000ml), Isosorbide-5-Nitrae-dibromobutane (88.09g, 407.96mmol) is added dropwise at 160 DEG C, then heats Stirring 3 hours.Temperature is reduced to normal temperature after terminating reaction, extracted with toluene (toluene) and water, then upper prop refines, Manufacture above-claimed cpd is the A1 (120g, yield 98%) of ivory white liquid.
MS[M+H]+=299.14
(2) A2 synthesis
By A1 (10g, 33.55mmol), 9,9 '-diphenyl -9H- fluorenes -2- amine (11.29g, 33.89mmol) and the tert-butyl alcohol Sodium (4.5g, 46.97mol) is put into toluene (toluene), heating stirring, is then flowed back and is put into [1,1'- double (hexichol Base phosphino-) ferrocene] palladium chloride (490mg, 2mmol%).Temperature is reduced to normal temperature and after terminating reaction, using chloroform and Ethyl acetate is recrystallized, and manufactures A2.
MS[M+H]+=552.26
(3) A3 synthesis
By A1 (10g, 40.79mmol), 9,9 '-diphenyl -9H- fluorenes -2- amine (13.87g, 41.61mmol) and the tert-butyl alcohol Sodium (4.5g, 46.97mol) is put into toluene (toluene), heating stirring, is then flowed back and is put into [1,1'- double (hexichol Base phosphino-) ferrocene] palladium chloride (490mg, 2mmol%).Temperature is reduced to normal temperature and after terminating reaction, using chloroform and Ethyl acetate is recrystallized, and manufactures A3.
MS[M+H]+=498.64
(4) A4 synthesis
By A1 (10g, 25.17mmol), 9,9 '-diphenyl -9H- fluorenes -2- amine (5.92g, 25.17mmol) and sodium tert-butoxide (4.5g, 46.97mol) is put into toluene (toluene), heating stirring, is then flowed back and is put into [1,1'- double (diphenyl Phosphino-) ferrocene] palladium chloride (490mg.2mmol%).After temperature is reduced into normal temperature and terminates reaction, ethyl acetate is utilized Recrystallized with hexane (hexane), manufacture A4.
MS[M+H]+=552.73
(5) B1 synthesis
In above-mentioned A1 synthesis, using 1, pentamethylene bromide replaces Isosorbide-5-Nitrae-dibromobutane, in addition, utilizes identical side Method manufactures B1 to synthesize.
MS[M+H]+=313.05
(6) B2 synthesis
In above-mentioned A2 synthesis, A1 is replaced using B1, in addition, B1 is manufactured to synthesize using identical method.
MS[M+H]+=566.28
<Production Example 2>The synthesis of-compound 1
By A2 (15g, 27.16mmol), 4- iodine biphenyl (7.75g, 27.7mmol) and sodium tert-butoxide (3.57g, 38.02mmol) it is put into toluene (toluene), heating stirring, is then flowed back and be put into double (tri-butyl phosphine) palladiums (277mg.2mmol%).After temperature is reduced into normal temperature and terminates reaction, tied again using tetrahydrofuran and ethyl acetate Crystalline substance, manufacture compound 1.
MS[M+H]+=713.32
<Production Example 3>The synthesis of-compound 2
In the synthesis of above-claimed cpd 1,4- iodine biphenyl is replaced using bromo- 9, the 9- dimethyl -9H- fluorenes of 2-, in addition, profit With identical method compound 2 is manufactured to synthesize.
MS[M+H]+=744.36
<Production Example 4>The synthesis of-compound 3
In the synthesis of above-claimed cpd 1,4- iodine biphenyl is replaced using bromo- 9, the 9- diphenyl -9H- fluorenes of 2-, in addition, profit With identical method compound 3 is manufactured to synthesize.
MS[M+H]+=868.39
<Production Example 5>The synthesis of-compound 4
In the synthesis of above-claimed cpd 1,4- iodine biphenyl is replaced using 4- (4- chlorphenyls) dibenzo [b, d] furans, except this Outside, manufacture compound 4 using identical method to synthesize.
MS[M+H]+=794.33
<Production Example 6>The synthesis of-compound 5
In the synthesis of above-claimed cpd 1, A2 is replaced using B2,4- iodine biphenyl is replaced using 4- bromines terphenyl, in addition, Using identical method compound 5 is manufactured to synthesize.
MS[M+H]+=794.37
<Production Example 7>The synthesis of-compound 6
In the synthesis of above-claimed cpd 1, A2 is replaced using B2, uses 4- chloro- 1,1:2,1 "-terphenyl joins instead of 4- iodine Benzene, in addition, compound 6 is manufactured to synthesize using identical method.
MS[M+H]+=794.37
<Production Example 8>The synthesis of-compound 7
In the synthesis of above-claimed cpd 3, A2 is replaced using B2, in addition, is manufactured using identical method to synthesize Compound 7.
MS[M+H]+=882.40
<Production Example 9>The synthesis of-compound 8
In the synthesis of above-claimed cpd 1, A2 is replaced using B2, is replaced using 4- (4- chlorphenyls) dibenzo [b, d] thiophene 4- iodine biphenyl, in addition, compound 8 is manufactured to synthesize using identical method.
MS[M+H]+=824.33
<Production Example 10>The synthesis of-compound 9
By A2 (15g, 27.21mmol), 3- (4- iodophenyls) -9- phenyl carbazoles (9.82g, 27.75mmol) and the tert-butyl alcohol Sodium (3.57g, 38.02mmol) is put into toluene (toluene), heating stirring, is then flowed back and is put into [double (three tertiary fourths Base phosphine)] palladium (277mg, 2mmol%).After temperature is reduced into normal temperature and terminates reaction, entered using tetrahydrofuran and ethyl acetate Row recrystallization, manufactures compound 9.
MS[M+H]+=870.12
<Production Example 11>The synthesis of-compound 10
By A3 (15g, 30.17mmol), 4- iodine biphenyl (10.26g, 30.77mmol) and sodium tert-butoxide (3.57g, 38.02mmol) it is put into toluene (toluene), heating stirring, is then flowed back and be put into [double (tri-butyl phosphines)] palladium (277mg.2mmol%).After temperature is reduced into normal temperature and terminates reaction, tied again using tetrahydrofuran and ethyl acetate Crystalline substance, manufacture compound 10.
MS[M+H]+=650.84
<Production Example 12>The synthesis of-compound 11
By A4 (15g, 27.18mmol), 4- iodine biphenyl (7.76g, 27.73mmol) and sodium tert-butoxide (3.57g, 38.02mmol) it is put into toluene (toluene), heating stirring, is then flowed back and be put into [double (tri-butyl phosphines)] palladium (277mg.2mmol%).After temperature is reduced into normal temperature and terminates reaction, tied again using tetrahydrofuran and ethyl acetate Crystalline substance, manufacture compound 11.
MS[M+H]+=704.93
<Embodiment>
<Embodiment 1>
Will be withThickness thin film be coated with ITO (tin indium oxide) glass substrate (healthy and free from worry 7059 glass) be put into it is molten Solution has in the distilled water of dispersant, is washed using ultrasonic wave.Detergent uses the system of Fei Xier companies (Fischer Co.) Product, distilled water use the distillation after being filtered 2 times by the filter (Filter) of Millipore Corp. (Millipore Co.) manufacture Water.After ITO is washed 30 minutes, with distilled water 2 ultrasonic washings for carrying out 10 minutes repeatedly.After distillation water washing terminates, Successively ultrasonic washing and drying are carried out with isopropanol, acetone, methanol solvate.
On the ito transparent electrode so prepared withThickness thermal vacuum evaporation X1 (hexanitrile Hexaazatriphenylene, the azepine benzophenanthrene of six nitrile six) and form hole injection layer.Vacuum is steamed over the hole-injecting layer PlatingAfter the compound 1 synthesized in above-mentioned Production Example 2 as the material of transporting holes, then, passed in above-mentioned hole On defeated layer withThickness vacuum evaporation HT2 and form hole regulating course.As compound light-emitting layer, withThickness Vacuum evaporation main body H1 and dopant D1 compounds (H1 is with 98% volume ratio of layer, D1 with 2% volume ratio presence of layer).So Afterwards, using E1 compounds and LiQ with 1:1 volume ratioAfter being formed as electron transfer layer, it is deposited successivelyThickness Lithium fluoride (LiF) andThe aluminium of thickness forms negative electrode, so as to manufacturing organic illuminating element.
In said process, the evaporation rate of organic matter maintainsLithium fluoride maintainsEvaporation speed Degree, aluminium maintainEvaporation rate.
<Embodiment 2>
In above-described embodiment 1, as hole transmission layer, the compound 1 for replacing synthesizing in Production Example 2 using compound 3, remove Outside this, similarly tested.
<Embodiment 3>
In above-described embodiment 1, as hole transmission layer, the compound 1 for replacing synthesizing in Production Example 2 using compound 6, remove Outside this, similarly tested.
<Embodiment 4>
In above-described embodiment 1, as hole transmission layer, the compound 1 for replacing synthesizing in Production Example 2 using compound 9, remove Outside this, similarly tested.
<Embodiment 5>
In above-described embodiment 1, as hole transmission layer, the compound 1 for replacing synthesizing in Production Example 2 using HT1, as sky Cave regulating course, HT2 is replaced using compound 5, in addition, is similarly tested.
<Embodiment 6>
In above-described embodiment 5, as hole regulating course, the compound 5 for replacing synthesizing in Production Example 6 using compound 7, remove Outside this, similarly tested.
<Embodiment 7>
In above-described embodiment 5, as hole regulating course, the compound 5 for replacing synthesizing in Production Example 6 using compound 11, In addition, similarly tested.
<Embodiment 8>
In above-described embodiment 5, as hole regulating course, the compound 5 for replacing synthesizing in Production Example 6 using compound 10, In addition, similarly tested.
<Embodiment 9>
On the ito transparent electrode prepared similarly to Example 1 withCompound 3 and shape is deposited in thickness thermal vacuum Into hole injection layerAlso, with 5% doping concentration, (compound 3 is present in layer with 95% volume ratio by X2 In, X2 is present in layer with 5% volume ratio) doping, material of the vacuum evaporation as transporting holes over the hole-injecting layer Above-claimed cpd 3Afterwards, then on above-mentioned hole transmission layer withThickness vacuum evaporation HT2, so as to Form hole regulating course.As compound light-emitting layer, withThickness vacuum evaporation main body H1 and dopant D1 compound (layers In, H1 exists with 98% volume ratio, and D1 is with 2% volume ratio presence).Then, using E1 compounds and LiQ with 1:1 volume ThanAfter being formed as electron transfer layer, it is deposited successivelyThe lithium fluoride (LiF) of thickness andThe aluminium of thickness comes Negative electrode is formed, so as to manufacture organic illuminating element.
<Embodiment 10>
In above-described embodiment 9, as hole injection layer and hole transmission layer, replace synthesizing in Production Example 4 using compound 4 Compound 3, in addition, similarly tested.
<Embodiment 11>
In above-described embodiment 9, as hole injection layer and hole transmission layer, compound 3 is replaced using HT1, as hole Regulating course, HT2 is replaced using compound 3, in addition, is similarly tested.
<Embodiment 12>
In above-described embodiment 10, as hole regulating course, the compound 3 for replacing synthesizing in Production Example 4 using compound 7, In addition, similarly tested.
<Comparative example 1>
In above-described embodiment 1, as hole transmission layer, the compound 1 that replaces synthesizing in Production Example 2 using HT1, except this it Outside, similarly tested.
<Comparative example 2>
In above-mentioned comparative example 1, as hole regulating course, HT2 is replaced using HT3, in addition, is similarly tested.
<Comparative example 3>
In above-mentioned comparative example 1, as hole transmission layer, HT1 is replaced using HT4, in addition, is similarly tested.
<Comparative example 4>
In above-described embodiment 11, as hole regulating course, the compound 3 for replacing synthesizing in Production Example 4 using HT2, except this Outside, similarly tested.
<Comparative example 5>
In above-described embodiment 1, as hole transmission layer, the compound 1 for replacing synthesizing in Production Example 2 using compound 10, In addition, similarly tested.
<Comparative example 6>
In above-described embodiment 9, as hole regulating course, the compound 3 for replacing synthesizing in Production Example 4 using compound 10, In addition, similarly tested.
[table 1]
<Embodiment 13>
On the ito transparent electrode so prepared withThickness thermal vacuum above-mentioned X1 is deposited and forms hole injection Layer.Compound 1 of the vacuum evaporation as the material of transporting holes over the hole-injecting layerAnd form hole transport Layer, utilizes HT2 over the hole-transporting layerAnd after forming hole regulating course, withThickness vacuum evaporation successively Main body H2 and dopant D2 (4 weight %).Then, using E1 compounds and LiQ with 1:1 volume ratioBe formed as electricity After sub- transport layer, it is deposited successivelyThe lithium fluoride (LiF) of thickness andThe aluminium of thickness forms negative electrode, so as to having manufactured Machine light-emitting component.
In said process, the evaporation rate of organic matter maintainsLithium fluoride maintainsAluminium maintainsEvaporation rate.
<Embodiment 14>
In above-described embodiment 13, as hole transmission layer, the compound 1 for replacing synthesizing in Production Example 2 using compound 3, In addition, similarly tested.
<Embodiment 15>
In above-described embodiment 13, as hole transmission layer, the compound 1 for replacing synthesizing in Production Example 2 using compound 8, In addition, similarly tested.
<Embodiment 16>
On the ito transparent electrode prepared similarly to Example 1 withCompound 2 and shape is deposited in thickness thermal vacuum Into hole injection layer, also, by compound X2 with 10% doping concentration (in layer, compound 2 with 90% volume ratio exist, X2 is with 10% volume ratio presence) doping, withThickness vacuum evaporation compound 2 and form hole transmission layer, at this Compound 5 is utilized on hole transmission layerAfter forming hole regulating course, withThickness vacuum evaporation main body successively H2 and dopant D2 (4 weight %).Then, using E1 compounds and LiQ with 1:1 volume ratioBe formed as electronics biography After defeated layer, it is deposited successivelyThe lithium fluoride (LiF) of thickness andThe aluminium of thickness forms negative electrode, organic so as to manufacture Light-emitting component.
<Embodiment 17>
In above-described embodiment 16, as hole injection layer and hole transmission layer, compound 2 is replaced using compound 5, as Hole regulating course, compound 5 is replaced using compound 7, in addition, is similarly tested.
<Embodiment 18>
In above-described embodiment 16, as hole injection layer and hole transmission layer, compound 2 is replaced using compound 9, as Hole regulating course, compound 5 is replaced using compound 7, in addition, is similarly tested.
<Embodiment 19>
In above-described embodiment 16, as hole injection layer and hole transmission layer, compound 2 is replaced using HT1, as hole Regulating course, compound 5 is replaced using compound 6, in addition, is similarly tested.
<Comparative example 5>
In above-described embodiment 13, as hole transmission layer, the compound 1 for replacing synthesizing in Production Example 2 using HT1, except this Outside, similarly tested.
<Comparative example 6>
In above-described embodiment 16, as hole injection layer and hole transmission layer, compound 2 is replaced using HT1, as hole Regulating course, compound 5 is replaced using HT2, in addition, is similarly tested.
<Comparative example 7>
In above-described embodiment 13, as hole transmission layer, the compound 1 for replacing synthesizing in Production Example 2 using compound 10, In addition, similarly tested.
[table 2]
As shown in above-mentioned Tables 1 and 2, the compound used in embodiment 1 to 19 is used as hole in organic illuminating element Implanted layer and hole transmission layer, hole regulating course, it is known that cavity transmission ability is more excellent compared with other materials, thus shows Low-voltage, efficient characteristic.

Claims (15)

1. the compound represented by following chemical formula 1 or 2：
Chemical formula 1
Chemical formula 2
In the chemical formula 1 or 2,
Q is substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring,
L1 is Direct Bonding, substituted or unsubstituted arlydene or substituted or unsubstituted heteroarylidene,
Ar1 is hydrogen, deuterium, halogen group, itrile group, nitro, hydroxyl, carbonyl, ester group, imide, amide groups, substitution or unsubstituted Alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy group, substitution or Unsubstituted alkyl sulfenyl, substituted or unsubstituted artyl sulfo, substituted or unsubstituted alkyl sulfoxide base, substitution or unsubstituted Alkenyl, substituted or unsubstituted silicyl, substituted or unsubstituted boryl, it is substituted or unsubstituted oxidation phosphino-, substitution Or unsubstituted amido, substituted or unsubstituted arylamine group, substituted or unsubstituted aryl or substituted or unsubstituted miscellaneous Aryl,
R1 to R6 is same to each other or different to each other, and is each independently hydrogen, deuterium, halogen group, itrile group, nitro, hydroxyl, carbonyl, ester Base, imide, amide groups, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alcoxyl Base, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkyl sulfenyl, substituted or unsubstituted artyl sulfo, substitution or Unsubstituted alkyl sulfoxide base, substituted or unsubstituted alkenyl, substituted or unsubstituted silicyl, substituted or unsubstituted oxygen Change phosphino-, substituted or unsubstituted amido, substituted or unsubstituted arylamine group, substituted or unsubstituted aryl or substitution Or unsubstituted heteroaryl,
N1 is 1 to 5 integer,
N2 is 1 to 5 integer,
N3 is 1 to 4 integer,
N4 is 1 to 3 integer,
N5 is 1 to 3 integer,
N6 is 1 to 4 integer,
When n1 to n6 is more than 2, the structure in more than 2 brackets is same to each other or different to each other.
2. compound according to claim 1, wherein, the Q is in following structures：
3. compound according to claim 1, wherein, the L1 that states is in following structures：
4. compound according to claim 1, wherein, the Ar1 is in following structures：
The R ' and R " is same to each other or different to each other, and is each independently hydrogen, deuterium, halogen group, itrile group, nitro, hydroxyl, carbonyl Base, ester group, imide, amide groups, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substitution or unsubstituted Alkoxy, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkyl sulfenyl, substituted or unsubstituted artyl sulfo, Substituted or unsubstituted alkyl sulfoxide base, substituted or unsubstituted alkenyl, substituted or unsubstituted silicyl, substitution do not take The oxidation phosphino- in generation, substituted or unsubstituted amido, substituted or unsubstituted arylamine group, substituted or unsubstituted aryl or The substituted or unsubstituted heteroaryl of person.
5. compound according to claim 1, wherein, the chemical formula 1 is represented by following chemical formula 3 to 6：
Chemical formula 3
Chemical formula 4
Chemical formula 5
Chemical formula 6
In the chemical formula 3 to 6,
Definition on Q, L1, Ar1, R1 to R6 and n1 to n6 is identical with the definition in above-mentioned chemical formula 1.
6. compound according to claim 1, wherein, the chemical formula 2 is represented by following chemical formula 7 to 10:
Chemical formula 7
Chemical formula 8
Chemical formula 9
Chemical formula 10
In the chemical formula 7 to 10,
Definition on Q, L1, Ar1, R1 to R6 and n1 to n6 is identical with the definition in above-mentioned chemical formula 2.
7. compound according to claim 1, wherein, the chemical formula 1 is any one in following compounds：
8. compound according to claim 1, wherein, the chemical formula 2 is any one in following compounds：
9. a kind of organic electronic element, wherein, including：First electrode, it is opposed with the first electrode and possess second electrode, And possess more than 1 layer of organic matter layer between the first electrode and the second electrode, 1 in the organic matter layer Layer compound according to any one of claims 1 to 8 contained above.
10. organic electronic element according to claim 9, wherein, the organic matter layer includes luminescent layer, the luminescent layer Include the compound.
11. organic electronic element according to claim 9, wherein, the organic matter layer includes hole injection layer or hole Transport layer, the hole injection layer or hole transmission layer include the compound.
12. organic electronic element according to claim 9, wherein, the organic matter layer includes electron injecting layer or electronics Transport layer, the electron transfer layer or electron injecting layer include the compound.
13. organic electronic element according to claim 9, wherein, the organic matter layer electronic barrier layer or hole barrier Layer, the electronic barrier layer or hole blocking layer include the compound.
14. organic electronic element according to claim 9, wherein, the organic electronic element is further included selected from hair 1 in photosphere, hole injection layer, hole transmission layer, electron injecting layer, electron transfer layer, electronic barrier layer and hole blocking layer Layer or more than 2 layers.
15. organic electronic element according to claim 9, wherein, the organic electronic element be selected from organic illuminating element, Phosphorescent element, organic solar batteries, Organophotoreceptor are OPC and organic transistor.
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