CN107459478A - 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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CN107459478A
CN107459478A CN201710397726.7A CN201710397726A CN107459478A CN 107459478 A CN107459478 A CN 107459478A CN 201710397726 A CN201710397726 A CN 201710397726A CN 107459478 A CN107459478 A CN 107459478A
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CN107459478B (en
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车龙范
金性昭
金振珠
洪性佶
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LG Chem Ltd
LG Corp
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LG Chemical Co Ltd
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    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
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    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
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    • 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
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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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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    • 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
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    • H10K50/14—Carrier transporting 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—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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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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Abstract

The present invention relates to compound and include its organic electronic element.The compound of the present invention 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
This specification advocates the korean patent application 10-2016- submitted on June 2nd, 2016 to Koran Office The priority of No. 0068890, its content all belong to this specification.
This specification is related to 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.
[chemical formula 1]
In above-mentioned chemical formula 1,
R1To R14It 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 (Alkyl Thioxy), substituted or unsubstituted artyl sulfo (Aryl thioxy), substituted or unsubstituted alkyl Sulfoxide group (Alkyl sulfoxy), substituted or unsubstituted alkenyl, substituted or unsubstituted monosilane Base, substituted or unsubstituted boryl, substituted or unsubstituted oxidation phosphino-, substituted or unsubstituted amido, substitution or unsubstituted Arylamine group, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl,
R1To R4It can be bonded to each other with adjacent group and form ring,
Ar1For substituted or unsubstituted terphenyl,
Ar2For substituted or unsubstituted aryl,
A is 1 to 4 integer,
B is 1 to 4 integer,
When a is more than 2, multiple R9It is same to each other or different to each other,
When b is more than 2, multiple R10It 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 one layer of organic matter between above-mentioned first electrode and above-mentioned second electrode Layer, one 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 more detail.
This specification provides the compound represented by above-mentioned chemical formula 1.
In compound represented by above-mentioned chemical formula 1, Ar1 has nuclear structure as terphenyl, thus with phenyl or Xenyl is compared, and Tg values raise more than 10 DEG C, and hole transmission layer and electronic barrier layer are particularly used as in organic illuminating element When, show long-life characteristics.In addition, when Ar2 is substituted with aryl, and electronic barrier layer is used as in organic illuminating element, the longevity Life can maintain peer-level, and show the characteristic of improved efficiency more than 5%.This is considered as, and in (meta) position With to R corresponding to (para) position11To R13The material that substituting has aryl is compared, and has deeper HOMO values, thus is reduced and lighted The barrier of layer, improve efficiency.
The illustration of substituent in this specification is described below, but not limited to this.
In this specification,Refer 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 position that position, the i.e. substituent that substituted position hydrogen atom can be substituted can substitute just does not limit, when When substituting more than 2, 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 is meant, by selected from deuterium, halogen group, itrile group, nitre Base, hydroxyl, carbonyl, ester group, imide, amide groups, alkyl, cycloalkyl, alkoxy, aryloxy group, alkyl sulfenyl, aryl sulphur Base, alkyl sulfoxide base, alkenyl, silicyl, boryl, oxidation phosphino-, amido, arylamine group, aryl and include N, O, S, Se Substitute with 1 in the heteroaryl of more than 1 in Si atoms or more than 2 substituents, or by foregoing illustrative substituent In the substituent substitution that is formed by connecting of the substituent of more than 2, or without any substituent.
In this specification, as the example of halogen group, including 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, Can be the compound of following structure, but 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, Can be the compound of following structural formula, but 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, can be following structure compound, but 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 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 not limited to this.
In this specification, cycloalkyl is not particularly limited, but the preferably cycloalkyl of carbon number 3 to 40, specifically, Including cyclopropyl, cyclobutyl, cyclopenta, 3- methylcyclopentyls, 2,3- dimethylcyclopentyls, cyclohexyl, 3- methylcyclohexyls, 4- Methylcyclohexyl, 2,3- Dimethylcyclohexyls, 3,4,5- trimethylcyclohexyls, 4- tert-butylcyclohexyls, suberyl, cyclooctyl Deng, but 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 and to methylbenzyloxy etc., but it is 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, including vinyl, 1- acrylic, isopropenyl, 1- cyclobutenyls, 2- cyclobutenyls, 3- cyclobutenyls, 1- pentenyls, 2- Pentenyl, 3- pentenyls, 3-methyl-1-butene base, 1,3- butadienyls, pi-allyl, 1- phenyl vinyl -1- bases, 2- phenyl Double (the hexichol of vinyl -1- bases, 2,2- diphenylacetylene -1- bases, 2- phenyl -2- (naphthyl -1- bases) vinyl -1- bases, 2,2- Base -1- bases) vinyl -1- bases, stilbenyl and styryl etc., but not limited to this.
In this specification, silicyl is the substituent being connected directly comprising Si and above-mentioned Si atoms as free radical, It is expressed as-SiR104R105R106, R104To R106Be same to each other or different to each other, and independently of one another can be by hydrogen, deuterium, halogen group, The substituent of at least one composition in alkyl, alkenyl, alkoxy, cycloalkyl, aryl and heterocyclic radical.Tool as silicyl Style, there are trimethyl silyl, triethylsilyl, t-butyldimethylsilyl, vinyl-dimethyl base monosilane Base, propyl-dimethyl silicyl, triphenyl-silyl, diphenylsilyl group and phenyl silyl groups etc., but be 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 The monocyclic or polycyclic heteroaryl of the base of more cyclophanes and substituted or unsubstituted carbon number 2 to 30.
This specification, in the case where aryl is monocyclic aryl, carbon number is not particularly limited, but preferred carbon number For 6 to 50.Specifically, can be phenyl, xenyl, terphenyl, tetrad phenyl etc., but be not limited to as monocyclic aryl 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 it is unlimited In 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 that above-mentioned fluorenyl is substituted, Ke Yiwei Deng, but not limited to this.
In this specification, heteroaryl 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 only 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, It is expressed as-NR107R108, 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 fluorenyl amidos and N- xenyl fluorenyl amidos etc., but not limited to this.
In this specification, as oxidation phosphino-, specifically, there are diphenyl phosphine oxide base, dinaphthyl phosphine oxide etc., but not It is limited to this.
In this specification, aryloxy group and 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, including 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, including phenyl amine, naphthylamine, xenylamine, anthryl amine, 3- methylphenyls amine, 4- methyl- Naphthylamine, 2- Methvl-biphenyls amine, 9- methyl-anthryl amine, diphenyl amido, phenyl napthyl amido, xylyl amido, benzene Base tolyl amido, carbazole and triphenyl amido etc., but 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 above-mentioned aryl can be applicable.
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, R1To R14It 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 boryl, it is substituted or unsubstituted oxidation phosphino-, substituted or unsubstituted amido, take Generation or unsubstituted arylamine group, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl.
In one embodiment of this specification, R1To R14It is same to each other or different to each other, and is each independently hydrogen.
In one embodiment of this specification, Ar1For substituted or unsubstituted terphenyl.
In one embodiment of this specification, Ar1Can be any one in following structural formula.
In one embodiment of this specification, Ar2For substituted or unsubstituted aryl.
In one embodiment of this specification, Ar2For substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl Base, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl or substituted or unsubstituted fluorenyl.
In one embodiment of this specification, Ar2For phenyl, xenyl, naphthyl, terphenyl or fluorenyl.
In one embodiment of this specification, above-mentioned chemical formula 1 can be represented by following chemical formula 2 or 3.
[chemical formula 2]
[chemical formula 3]
In above-mentioned chemical formula 2 and 3,
For R1To R14、Ar1、Ar2, a and b definition, it is identical with the definition in above-mentioned chemical formula 1.
In one embodiment of this specification, above-claimed cpd can be any one in following structural formula.
It can be manufactured according to the compound of this specification embodiment by manufacture method described later.It is described later In Production Example, although describing representational illustration, as needed, substituent can be added or delete, and can change and take Dai Ji position.In addition, being based on technology as known in the art, initial substance, reactive material, reaction condition etc. can be changed.
For example, the compound of above-mentioned chemical formula 1 can be by reacting to manufacture as following reaction equations 1 to 5.Substitution Base can be combined by methods known in the art, and species, position or the number of substituent can be according to known in the art Technology changes.Specific manufacture method will be aftermentioned.
[reaction equation 1]
[reaction equation 2]
[reaction equation 3]
[reaction equation 4]
[reaction equation 5]
In addition, this specification provides the organic electronic element for including above-claimed cpd.
The compound of one embodiment of this specification can be manufactured by manufacture method described later.Manufacture described later In example, although describing representational illustration, as needed, substituent can be added or delete, and substituent can be changed Position.In addition, being based on technology as known in the art, initial substance, reactive material, reaction condition etc. can be changed.
In addition, this specification provides the organic illuminating element for including above-claimed cpd.
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 possess one layer between above-mentioned first electrode and above-mentioned second electrode More than organic matter layer, one 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 two 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 Less organic layer.
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 One layer or two in layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer, hole blocking layer and electronic barrier layer It is more than layer.
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 two 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 two layers of organic matter layer includes above-claimed cpd.In one embodiment of this specification, Above-mentioned more than two layers of organic matter layer from electron transfer layer, electron injecting layer while can carry out electric transmission and electron injection Layer and hole blocking layer in select more than two layers.
In one embodiment of this specification, above-mentioned organic matter layer includes more than two layers of electron transfer layer, and above-mentioned two At least one layer in electron transfer layer more than layer includes above-claimed cpd.Specifically, an embodiment of this specification In, it can be one layer in above-mentioned more than two layers of electron transfer layer and include above-claimed cpd or above-mentioned more than two layers Electron transfer layer include above-claimed cpd respectively.
In addition, in an embodiment of this specification, above-mentioned more than two layers of electron transfer layer includes above-mentionedization respectively In the case of compound, 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 one layer The organic illuminating element of the structure of organic matter layer and 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 another embodiment, organic illuminating element can be sequentially laminated with substrate negative electrode, more than one layer The organic illuminating element of the reverse structure of organic matter layer and 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 it is unlimited In 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 structure of the organic illuminating element of an embodiment of this specification, Other organic matter layers can further be included.
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 the exemplary structure 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 one 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 where above-mentioned organic illuminating element includes multilayer organic matter layer, above-mentioned organic matter layer can be by same substance Or different material is formed.
The organic illuminating element of this specification is except one 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 by 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 (sputtering) or electron-beam vapor deposition method (e-beam ) etc evaporation PVD (physical vapor deposition method, Physical Vapor Deposition), the gold evaporation on substrate Category or conductive metal oxide or their alloy and form anode, formed on the anode and injected comprising hole Layer, hole transmission layer, the organic matter layer of luminescent layer and electron transfer layer, then evaporation can be used as negative electrode on the organic matter layer Material., also can evaporation cathode material, organic matter layer, anode material manufacture successively on substrate in addition to such method 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.Here, 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 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 is big Material.As the concrete example for the anode material that can be used 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, the preferred small thing of work function Matter.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 they 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, have for luminescent layer or luminescent material excellent Different hole injection effect；Prevent that caused exciton migrates to electron injecting layer or electron injection material in luminescent layer；And 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, luminescent layer and electronics can be formed at using known material Suitable part between implanted 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；Dimer styryl (dimerized styryl) compound；BAlq；10- hydroxy benzo quinoline metal compounds；BenzoAzoles, benzothiazole and Benzimidazole based compound；Poly- (to phenylene vinylidene) (PPV) is macromolecule；It is loop coil (spiro) compound, 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 and 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 dibenzofuran derivative, ladder type furans Compound Pyrimidine derivatives etc., but not limited to this.
As above-mentioned dopant material, there are aromatic amine derivative, styrylamine compounds, boron complexes, fluoranthene Compound and 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, there is styryl amine, styryl diamines, styryl triamine, styryl tetramine etc., but not limited to this.In addition, conduct Metal complex, there are complex of iridium, platinum complex etc., but 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 as used in conventional art It is used together with the cathode substance of any desired.Particularly, the example of suitable cathode substance is with low work function and adjoint The common material of aluminium lamination or silver layer.Specially caesium, barium, calcium, ytterbium and samarium, for 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, there is the electron injection effect from negative electrode, there is excellent electron injection effect for luminescent layer or luminescent material, Prevent that caused exciton migrates to hole injection layer in luminescent layer, and film Forming ability is excellent.Specifically, there is fluorenes Ketone, anthraquinone bismethane (Anthraquinodimethane), diphenoquinone, thiopyrandioxide,Azoles,Diazole, triazole, miaow Azoles, tetrabasic carboxylic acid, fluorenylidene-methane, anthrone etc. and its derivative, metal complex, and nitrogenous 5 membered ring derivatives etc., but it is unlimited In 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 not limited to this.
Above-mentioned hole blocking layer be prevent hole reach negative electrode layer, typically can by with hole injection layer identical bar Part is formed.Specifically, haveOxadiazole derivative or triazole derivative, phenanthroline derivative, BCP, aluminum complex (aluminum complex) etc., but not limited to this.
The organic illuminating element of this specification material used in, 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.
The compound of this specification principle similar when can be by with applied to organic illuminating element is and applied to have Machine phosphorescent element, organic solar batteries, Organophotoreceptor, organic transistor etc. are the organic electronic element of 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 deformed into 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.
<Embodiment>
[reaction equation 1]
[reaction equation 2]
[reaction equation 3]
[reaction equation 4]
<Production Example 1>
1) following compound A synthesis
Under nitrogen atmosphere, in 2L round-bottomed flasks, by compound 9- (4- bromophenyls) -9H- carbazoles (100.0g, 311.53mmol), after (4- chlorphenyls) boric acid (53.46g, 342.68mmol) is dissolved completely in tetrahydrofuran 600ml, addition 2M wet chemicals (300ml), after adding four-(triphenylphosphine) palladiums (10.80g, 9.35mmol), carry out heating in 5 hours and stir Mix.Temperature is reduced to normal temperature, water layer is removed, after being dried using anhydrous magnesium sulfate, is concentrated under reduced pressure, utilizes tetrahydrofuran 260ml is recrystallized, manufacture compound A (88.54g, 80%).
MS[M+H]+=354
2) synthesis of following compounds 1
Under nitrogen atmosphere, in 500ml round-bottomed flasks, by above-claimed cpd A (8.67g, 24.49mmol), N- ([1,1'- Biphenyl] -2- bases)-[1,1':4', 1 "-terphenyl] -4- amine (10.70g, 26.94mmol) is dissolved completely in dimethylbenzene (Xylene) after in 220ml, sodium tert-butoxide (3.06g, 31.84mmol) is added, adds double (tri-butyl phosphine) palladiums (0) After (0.13g, 0.24mmol), 3 hours heating stirrings are carried out.Temperature is reduced to normal temperature, filtering and after salt is removed, make diformazan Benzene (Xylene) is concentrated under reduced pressure, and is recrystallized using ethyl acetate 260ml, manufactures compound 1 (13.34g, yield：76%).
MS[M+H]+=715
<Production Example 2>The synthesis of-following compounds 2
Under nitrogen atmosphere, in 500ml round-bottomed flasks, by compound A (7.26g, 20.51mmol), N- ([1,1'- connection Benzene] -2- bases)-[1,1':3', 1 "-terphenyl] -5'- amine (8.96g, 22.56mmol) is dissolved completely in dimethylbenzene (Xylene) After in 180ml, addition sodium tert-butoxide (2.56g, 26.66mmol), double (tri-butyl phosphine) palladiums (0) of addition (0.10g, After 0.21mmol), 3 hours heating stirrings are carried out.Temperature is reduced to normal temperature, filtering and after salt is removed, make dimethylbenzene (Xylene) it is concentrated under reduced pressure, is recrystallized using ethanol 340ml, manufactures compound 2 (10.16g, yield：69%).
MS[M+H]+=715
<Production Example 3>The synthesis of-following compounds 3
Under nitrogen atmosphere, in 500ml round-bottomed flasks, by compound A (6.55g, 18.50mmol), N- ([1,1'- connection Benzene] -2- bases)-[1,1':4', 1 "-terphenyl] -2- amine (8.08g, 20.35mmol) is dissolved completely in dimethylbenzene (Xylene) After in 210ml, addition sodium tert-butoxide (2.31g, 24.05mmol), double (tri-butyl phosphine) palladiums (0) of addition (0.09g, After 0.19mmol), 3 hours heating stirrings are carried out.Temperature is reduced to normal temperature, filtering and after salt is removed, make dimethylbenzene (Xylene) it is concentrated under reduced pressure, is recrystallized using ethanol 300ml, manufactures compound 3 (7.69g, yield：58%).
MS[M+H]+=715
<Production Example 4>The synthesis of-following compounds 4
Under nitrogen atmosphere, in 500ml round-bottomed flasks, by compound A (5.29g, 14.94mmol), N- ([1,1':4', 1 "-terphenyl] -4- bases)-[1,1':4', 1 "-terphenyl] -2- amine (7.78g, 16.44mmol) is dissolved completely in dimethylbenzene (Xylene) after in 260ml, sodium tert-butoxide (1.87g, 19.43mmol) is added, adds double (tri-butyl phosphine) palladiums (0) After (0.08g, 0.15mmol), 3 hours heating stirrings are carried out.Temperature is reduced to normal temperature, filtering and after salt is removed, make diformazan Benzene (Xylene) is concentrated under reduced pressure, and is recrystallized using ethyl acetate 240ml, manufactures compound 4 (6.44g, yield：54%).
MS[M+H]+=791
<Production Example 5>
1) following compound B synthesis
Under nitrogen atmosphere, in 1L round-bottomed flasks, by compound 7- (4- bromophenyls) -7H- benzos [c] carbazole (30.0g, 80.86mmol), after (4- chlorphenyls) boric acid (13.88g, 88.95mmol) is dissolved completely in tetrahydrofuran 200ml, 2M is added Wet chemical (100ml), after adding four-(triphenylphosphine) palladiums (2.80g, 2.43mmol), carry out 5 hours heating stirrings. Temperature is reduced to normal temperature, water layer is removed, after being dried using anhydrous magnesium sulfate, is concentrated under reduced pressure, utilizes tetrahydrofuran 260ml is recrystallized, manufacture compound B (24.45g, 75%).
MS[M+H]+=404
2) synthesis of following compounds 5
Under nitrogen atmosphere, in 500ml round-bottomed flasks, by compound B (9.41g, 21.34mmol), N- ([1,1'- connection Benzene] -2- bases)-[1,1':4', 1 "-terphenyl] -4- amine (9.32g, 23.47mmol) is dissolved completely in dimethylbenzene (Xylene) After in 280ml, addition sodium tert-butoxide (2.67g, 27.74mmol), double (tri-butyl phosphine) palladiums (0) of addition (0.22g, After 0.43mmol), 3 hours heating stirrings are carried out.Temperature is reduced to normal temperature, filtering and after salt is removed, make dimethylbenzene (Xylene) it is concentrated under reduced pressure, is recrystallized using tetrahydrofuran 230ml, manufactures compound 5 (9.86g, yield：60%).
MS[M+H]+=764
<Production Example 6>
1) following compound C synthesis
Under nitrogen atmosphere, in 1L round-bottomed flasks, by compound 11- (4- bromophenyls) -11H- benzos [a] carbazole (50.0g, 134.77mmol), (4- chlorphenyls) boric acid (23.13g, 148.25mmol) are dissolved completely in tetrahydrofuran 400ml Afterwards, 2M wet chemicals (200ml) are added, after adding four-(triphenylphosphine) palladiums (1.38g, 2.70mmol), are carried out 7 hours Heating stirring.Temperature is reduced to normal temperature, water layer is removed, after being dried using anhydrous magnesium sulfate, is concentrated under reduced pressure, utilizes second Alcohol 450ml is recrystallized, manufacture compound C (38.84g, 71%).
MS[M+H]+=404
2) synthesis of following compounds 6
Under nitrogen atmosphere, in 500ml round-bottomed flasks, by compound C (6.29g, 14.26mmol), N- ([1,1'- connection Benzene] -2- bases)-[1,1':4', 1 "-terphenyl] -4- amine (6.23g, 15.69mmol) is dissolved completely in dimethylbenzene (Xylene) After in 220ml, addition sodium tert-butoxide (1.78g, 18.54mmol), double (tri-butyl phosphine) palladiums (0) of addition (0.15g, After 0.29mmol), 2 hours heating stirrings are carried out.Temperature is reduced to normal temperature, filtering and after salt is removed, make dimethylbenzene (Xylene) it is concentrated under reduced pressure, is recrystallized using tetrahydrofuran 200ml, manufactures above-claimed cpd 6 (6.75g, yield： 62%).
MS[M+H]+=764
<Production Example 7>
1) following compound D synthesis
Under nitrogen atmosphere, in 1L round-bottomed flasks, by compound 9- (2- bromophenyls) -9H- carbazoles (20.0g, 62.31mmol), after (4- chlorphenyls) boric acid (10.21g, 65.42mmol) is dissolved completely in tetrahydrofuran 360ml, 2M is added Wet chemical (180ml), after adding four-(triphenylphosphine) palladiums (2.16g, 1.87mmol), carry out 6 hours heating stirrings. Temperature is reduced to normal temperature, water layer is removed, after being dried using anhydrous magnesium sulfate, is concentrated under reduced pressure, utilizes tetrahydrofuran 240ml is recrystallized, manufacture compound D (15.79g, 72%).
MS[M+H]+=354
2) synthesis of following compounds 7
Under nitrogen atmosphere, in 500ml round-bottomed flasks, by compound A (15.79g, 44.73mmol), N- ([1,1'- connection Benzene] -2- bases)-[1,1':4', 1 "-terphenyl] -4- amine (18.65g, 46.97mmol) is dissolved completely in dimethylbenzene (Xylene) After in 320ml, addition sodium tert-butoxide (5.59g, 58.15mmol), double (tri-butyl phosphine) palladiums (0) of addition (0.46g, After 0.89mmol), 5 hours heating stirrings are carried out.Temperature is reduced to normal temperature, filtering and after salt is removed, make dimethylbenzene (Xylene) it is concentrated under reduced pressure, is recrystallized using tetrahydrofuran 260ml, manufactures compound 7 (21.12g, yield：66%).
MS[M+H]+=715
<Experimental example 1-1>
Will be withThickness thin film put coated with ITO (tin indium oxide, indium tin oxide) glass substrate Enter in the distilled water dissolved with detergent, washed using ultrasonic wave.Now, as detergent, Fei Xier companies are used (Fischer Co.) product, as distilled water, use the filter manufactured by Millipore Corp. (Millipore Co.) (Filter) distilled water after filtering 2 times.By ITO wash 30 minutes after, using distilled water repeatedly 2 times and carry out 10 minutes ultrasounds Ripple washs.After distillation water washing terminates, ultrasonic washing is carried out and after drying using the solvent of isopropanol, acetone, methanol, transfer Into plasma washing machine.Then, after aforesaid substrate is cleaned 5 minutes using oxygen plasma, by base plate transfer to vacuum In evaporator.
On the ito transparent electrode so prepared withThickness thermal vacuum evaporation following chemical formula the nitrogen of six nitrile six Miscellaneous benzophenanthrene (hexanitrile hexaazatriphenylene；HAT hole injection layer) is formed.
[HAT]
Following compound N 4, N4, N4's of the vacuum evaporation as the material of transporting holes on above-mentioned hole injection layer, N4'- tetra- ([1,1'- biphenyl] -4- bases)-[1,1'- biphenyl] -4,4'- diaminesAnd form hole transmission layer.
[HT1]
Then, with film thickness on above-mentioned hole transmission layerThe following compounds 1 of vacuum evaporation and formed electronics resistance Barrier.
[compound 1]
Then, with film thickness on above-mentioned electronic barrier layerBy following BH and BD with 25:1 weight is trueer than carrying out Sky is deposited and forms luminescent layer.
[BH]
[BD]
[ET1]
[LiQ]
With 1 on above-mentioned luminescent layer:1 weight is than vacuum evaporation above-claimed cpd ET1 and above-claimed cpd LiQ (hydroxyls Quinoline lithium, Lithium Quinolate) and withThickness form electron injection and transport layer.In above-mentioned electron injection With in transport layer successively withThickness evaporation lithium fluoride (LiF), withThickness AM aluminum metallization and form negative electrode.
In said process, the evaporation rate of organic matter maintain 0.4 toThe lithium fluoride of negative electrode maintainsEvaporation rate, aluminium maintainEvaporation rate, vacuum maintains 2 × 10 during evaporation-7To 5 × 10- 6Torr, so as to make organic illuminating element.
<Experimental example 1-2>
In above-mentioned experimental example 1-1, using above-claimed cpd 2 replace compound 1, in addition, using with experimental example 1-1 phases Same method makes organic illuminating element.
<Experimental example 1-3>
In above-mentioned experimental example 1-1, using above-claimed cpd 3 replace compound 1, in addition, using with experimental example 1-1 phases Same method makes organic illuminating element.
<Experimental example 1-4>
In above-mentioned experimental example 1-1, using above-claimed cpd 4 replace compound 1, in addition, using with experimental example 1-1 phases Same method makes organic illuminating element.
<Experimental example 1-5>
In above-mentioned experimental example 1-1, using above-claimed cpd 5 replace compound 1, in addition, using with experimental example 1-1 phases Same method makes organic illuminating element.
<Experimental example 1-6>
In above-mentioned experimental example 1-1, using above-claimed cpd 6 replace compound 1, in addition, using with experimental example 1-1 phases Same method makes organic illuminating element.
<Experimental example 1-7>
In above-mentioned experimental example 1-1, using above-claimed cpd 7 replace compound 1, in addition, using with experimental example 1-1 phases Same method makes organic illuminating element.
<Comparative example 1-1>
In above-mentioned experimental example 1-1, compound 1, in addition, utilization and experimental example are replaced using following EB1 compound 1-1 identicals method makes organic illuminating element.
[EB1]
<Comparative example 1-2>
In above-mentioned experimental example 1-1, compound 1, in addition, utilization and experimental example are replaced using following EB2 compound 1-1 identicals method makes organic illuminating element.
[EB2]
<Comparative example 1-3>
In above-mentioned experimental example 1-1, compound 1, in addition, utilization and experimental example are replaced using following EB3 compound 1-1 identicals method makes organic illuminating element.
[EB3]
<Comparative example 1-4>
In above-mentioned experimental example 1-1, compound 1, in addition, utilization and experimental example are replaced using following EB4 compound 1-1 identicals method makes organic illuminating element.
[EB4]
The vitrifying that measure passes through above-mentioned experimental example 1-1 to 1-7 and comparative example 1-1 to the 1-4 organic illuminating element made Transition temperature (Tg) value, and carry out sublimation purifying and physical property is shown in table 1 below.
[table 1]
As shown in Table 1 above, structures of the comparative example 1-1 EB1 due to being symmetrically connected with xenyl with amine both sides, therefore Sublimation temperature is up to 380 DEG C, and distillation type is L to S.This may induce blocking (Clogging) when making organic illuminating element Phenomenon.Above-mentioned so-called distillation type (Sub Type), refer to the physical change for confirming material, there is L to L, L to S, S to tri- kinds of S Type.Above-mentioned L to L refers to liquid to liquid, and L to S refers to liquid to solid-state, and S to S refers to solid-state to solid-state, as L to L is to S Promoted to S, improve and can be lowered and the purity obtained by sublimation purifying.In addition, as comparative example 1-2 EB2, in Ar2 Position connection phenyl is used as substituent, is made so as to want to make sublimation temperature reduction while by the raising of the solubility of material Material due to HOMO values it is deeper, therefore obtain reducing and result that efficiency uprises with the potential barrier of luminescent layer (barrier).But It is, due to as little as 116 DEG C of glass transition temperature (Tg) value, thus it is shown that because being impacted and the life-span to the stability of element The characteristic substantially reduced.
Therefore, the compound represented by the chemical formula 1 of the present application passes through in Ar2Position connect substituent, and make Ar1 The terphenyl for the molecular weight being substituted by more than with biphenyl, so as to also put forward high tg values while efficiency is improved, improve element Stability.
Using the experimental example 1-1 of above-claimed cpd 1 to 7 into 1-7, as observing, Tg values be 130 DEG C with On, between sublimation temperature is 330 to 360 DEG C, the distillation type of measure is L to L.
In addition, measure applies electricity to the organic illuminating element made by experimental example 1-1 to 1-7 and comparative example 1-1 to 1-4 Voltage, efficiency, EL peaks and life-span during stream, and show the result in following [tables 2].T95 means, brightness is from original intensity (5000nit) is reduced to the time required when 95%.
[table 2]
It was found from above-mentioned table 2, the having for manufacturing using the compound represented by the application chemical formula 1 as electronic barrier layer Machine light-emitting component is compared with comparative example 1-1 to comparative example 1-4, and organic illuminating element is in efficiency, driving voltage and/or stability side Face show by the electronic blocking zone of action of the compound represented by the application chemical formula 1 Lai excellent characteristic.Particularly, from The result of above-mentioned table 2 is observed, using the experimental example 1-1 of the compound represented by the application chemical formula 1 into 1-7, is shown Voltage reduces 10% to 20%, and efficiency improves more than 10% characteristic.
Furthermore, it is possible to confirm, the compound represented by the application chemical formula 1 is in Ar2Connect substituent and improve material Solubility, while maintain low driving voltage and efficient characteristic, on the other hand, connect Ar1 with terphenyl and improve member The stability of part, also maintains long-life characteristics, so as to applied to organic illuminating element.
By the above, a preferred embodiment of the present invention (electronic barrier layer) is illustrated, but the present invention is simultaneously Not limited to this, it can implement in the range of the scope of protection of present invention and the embodiment of invention various Change, this falls within the category of invention.

Claims (11)

1. a kind of compound, it is represented by following chemical formula 1,
Chemical formula 1
In the chemical formula 1,
R1To R14It 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 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,
R1To R4It can be bonded to each other with adjacent group and form ring,
Ar1For substituted or unsubstituted terphenyl,
Ar2For substituted or unsubstituted aryl,
A is 1 to 4 integer,
B is 1 to 4 integer,
When a is more than 2, multiple R9It is same to each other or different to each other,
When b is more than 2, multiple R10It is same to each other or different to each other.
2. compound according to claim 1, wherein, the chemical formula 1 is represented by following chemical formula 2 or chemical formula 3,
Chemical formula 2
Chemical formula 3
In the chemical formula 2 and chemical formula 3,
For R1To R14、Ar1、Ar2, a and b define it is identical with defined in the chemical formula 1.
3. compound according to claim 1, wherein, Ar1For any one in following structural formula：
4. compound according to claim 1, wherein, the chemical formula 1 is any one in following compounds：
5. 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 one layer of organic matter layer between the first electrode and the second electrode, in the organic matter layer One layer of compound according to any one of claims 1 to 4 contained above.
6. organic electronic element according to claim 5, wherein, the organic matter layer includes luminescent layer, the luminescent layer Include the compound.
7. organic electronic element according to claim 5, wherein, the organic matter layer includes hole injection layer or hole passes Defeated layer, the hole injection layer or hole transmission layer include the compound.
8. organic electronic element according to claim 5, wherein, the organic matter layer includes electron injecting layer or electronics passes Defeated layer, the electron transfer layer or electron injecting layer include the compound.
9. organic electronic element according to claim 5, wherein, the organic matter layer includes electronic barrier layer or hole hinders Barrier, the electronic barrier layer or hole blocking layer include the compound.
10. organic electronic element according to claim 5, wherein, the organic electronic element is further included selected from hair One in photosphere, hole injection layer, hole transmission layer, electron injecting layer, electron transfer layer, electronic barrier layer or hole blocking layer Layer or more than two layers.
11. organic electronic element according to claim 5, it is characterised in that the organic electronic element is selected from organic hair Optical element, Phosphorescent element, organic solar batteries, Organophotoreceptor are OPC and organic transistor.
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