CN107311987A - Compound and the organic electronic element comprising it - Google Patents

Compound and the organic electronic element comprising it Download PDF

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CN107311987A
CN107311987A CN201710270412.0A CN201710270412A CN107311987A CN 107311987 A CN107311987 A CN 107311987A CN 201710270412 A CN201710270412 A CN 201710270412A CN 107311987 A CN107311987 A CN 107311987A
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CN107311987B (en
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郑珉祐
李东勋
许净午
张焚在
许东旭
姜敏英
韩美连
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LG Chem Ltd
LG Corp
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Abstract

A kind of organic electronic element the present invention relates to compound and comprising it.The compound of the present invention is used for organic electronic element using organic illuminating element as representative, can reduce the driving voltage of organic electronic element, improves light efficiency, and improves using the heat endurance of compound the life characteristic of element.

Description

Compound and the organic electronic element comprising it
Technical field
The application advocates the korean patent application 10-2016- submitted on April 25th, 2016 in Koran Office The priority of No. 0050216, its content is integrally incorporated in this specification.
This specification is related to a kind of compound and the organic electronic element comprising it.
Background technology
As the typical example of organic electronic element, there is organic illuminating element.In general, organic light emission phenomenon refers to, profit Electric energy is set to be changed into the phenomenon of luminous energy with organic substance.Generally have using the organic illuminating element of organic light emission phenomenon and include sun Pole and negative electrode and the structure positioned at the organic matter layer between them.Wherein, in order to improve the efficiency of organic illuminating element and steady Qualitative, the sandwich construction being often made up of each different materials forms organic matter layer, for example, can be by hole injection layer, sky The formation such as cave transport layer, luminescent layer, electron transfer layer, electron injecting layer.For the structure of such organic illuminating element, If applying voltage between electrodes, hole is injected into organic matter layer from anode, and electronics is injected into organic matter layer from negative electrode, Exciton (exciton) is formed when institute's injected holes and electronics meet, light will be sent when the exciton transits to ground state again.
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
The application provides a kind of compound and the organic electronic element comprising it.
The application provides the compound represented by following chemical formula 1.
[chemical formula 1]
In above-mentioned chemical formula 1,
R1 to R4 is same to each other or different to each other, and be each independently hydrogen, deuterium, halogen group, substituted or unsubstituted alkyl, Substituted or unsubstituted cycloalkyl, substituted or unsubstituted oxidation phosphino-, substituted or unsubstituted aryl or substitution do not take The heteroaryl in generation,
A is 1 to 3 integer,
B is 1 to 3 integer,
When a is more than 2, multiple R3 are same to each other or different to each other,
When b is more than 2, multiple R4 are same to each other or different to each other,
A1 and A2 are same to each other or different to each other, and any for what is selected from following structures,
Z1 into Z3 at least one be N, remaining is same to each other or different to each other, and is each independently N or CR,
X be NAr1, O or S,
Q is substituted or unsubstituted monocyclic or polycyclic aromatic ring or substituted or unsubstituted monocyclic or polycyclic Heterocycle,
L1Be same to each other or different to each other to L6, and be each independently Direct Bonding, substituted or unsubstituted arlydene or Substituted or unsubstituted heteroarylidene,
Ar1 be substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl,
Ar2 to Ar5 is same to each other or different to each other, and is each independently hydrogen, deuterium, halogen group, substituted or unsubstituted alkane Base, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl or substitution do not take The heteroaryl in generation,
R and R5 to R10 is same to each other or different to each other, and be each independently hydrogen, it is deuterium, halogen group, substituted or unsubstituted Alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted oxidation phosphino-, substituted or unsubstituted aryl or substitution Or unsubstituted heterocyclic radical,
R5 is 1 to 4 integer,
R6 is 1 to 4 integer,
R7 is 1 to 4 integer,
R8 is 1 to 2 integer,
R9 is 1 to 4 integer,
R10 is 1 to 6 integer,
When r5 is more than 2, multiple R5 are same to each other or different to each other,
When r6 is more than 2, multiple R6 are same to each other or different to each other,
When r7 is more than 2, multiple R7 are same to each other or different to each other,
When r8 is 2, multiple R8 are same to each other or different to each other,
When r9 is more than 2, multiple R9 are same to each other or different to each other,
When r10 is more than 2, multiple R10 are 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 the 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 1 layer of foregoing compound contained above in layer, 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 improve using the heat endurance of compound The life characteristic of element.
Brief description of the drawings
Fig. 1 shows the organic illuminating element 10 of an embodiment according to this specification.
Fig. 2 shows the organic illuminating 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.
The compound that the offer of this specification is represented by above-mentioned chemical formula 1.
The example of substituent in this specification is described below, but is 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 commutable position of position, i.e. substituent that substituted position hydrogen atom can be substituted just is not limited, 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, be selected from deuterium, halogen group, cyano group, nitro, Hydroxyl, carbonyl, alkyl, cycloalkyl, oxidation phosphino-, aryl, silicyl and include 1 in N, O, S, Se and Si atom 1 in heterocyclic radical above or more than 2 substituents substitutions, or taking by more than 2 in foregoing illustrative substituent The substituent substitution that Dai Ji 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, alkyl can be straight or branched, and carbon number is not particularly limited, but preferably 1 to 50.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, 4- methylhexyls, 5- methylhexyls 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 60, 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, silicyl is the substitution being directly connected to comprising Si and above-mentioned Si atoms as free radical Base, and with-SiR201R202R203Represent, R201To R203It is same to each other or different to each other, can is by hydrogen, deuterium, halogen radical independently of one another At least one substituent constituted in group, alkyl, alkenyl, alkoxy, cycloalkyl, aryl and heterocyclic radical.It is used as silicyl Concrete example, have trimethyl silyl, triethylsilyl, t-butyldimethylsilyl, vinyl-dimethyl Ji Jia Silylation, propyl-dimethyl silicyl, triphenyl-silyl, diphenylsilyl group, phenyl silyl groups etc., but not It is limited to this.
In this specification, in the case where aryl is monocyclic aryl, carbon number is not particularly limited, but preferably carbon is former The monocyclic aryl of subnumber 6 to 50.Specifically, can be phenyl, xenyl, terphenyl, tetrad phenyl as monocyclic aryl Deng, but it is not limited to this.
In the case where above-mentioned aryl is polyaromatic, carbon number is not particularly limited, but preferably carbon number 10 To 50 polyaromatic.Specifically, as polyaromatic, can for naphthyl, anthryl, phenanthryl, pyrenyl, perylene base,Base, fluorenyl Deng, but it is not 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 the preferably heterocyclic radical of carbon number 2 to 60.As the example of heterocyclic radical, there are thienyl, furan Mutter base, pyrrole radicals, imidazole radicals, thiazolyl,Oxazolyl,Di azoly, triazolyl, pyridine radicals, bipyridyl, pyrimidine radicals, triazine Base, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolyl, quinoxalinyl, phthalazinyl, Pyridopyrimidine base, pyrido pyrrole Piperazine base, pyrazine and pyrazinyl, isoquinolyl, indyl, carbazyl, benzoOxazolyl, benzimidazolyl, benzothiazolyl, benzene And carbazyl, benzothienyl, dibenzothiophenes base, benzofuranyl, phenanthroline (phenanthroline) base, thiazolyl, It is differentOxazolyl,Di azoly, thiadiazolyl group and dibenzofuran group etc., but it is not limited to this.
In this specification, heteroaryl is aromatic series ring group, in addition, can be selected from the example of above-mentioned heterocyclic radical, But it is not limited to this.
In this specification, the aromatic series ring groups of 2 to 4 valencys can be monocyclic or polycyclic, refer to have on above-mentioned aryl 2 to The group of the group of 4 binding sites, i.e. 2 to 4 valencys.They are in addition to being respectively the group of 2 to 4 valencys, applicable above-mentioned virtue The explanation of base.
In this specification, arlydene refers to, the group on aryl with two basic change position, i.e. divalent group.They are removed It is respectively beyond divalent group, the explanation of applicable above-mentioned aryl.
In this specification, heteroarylidene refers to, the group on heteroaryl with two basic change position, i.e. divalent group.It In addition to being respectively divalent group, the explanation of applicable above-mentioned heteroaryl.
According to this specification embodiment, R1 to R4 is same to each other or different to each other, and be each independently hydrogen, deuterium, Halogen group, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted oxidation phosphino-, substitution Or unsubstituted aryl or substituted or unsubstituted heteroaryl.
According to this specification embodiment, R1 to R4 is same to each other or different to each other, and be each independently substitution or The alkyl of unsubstituted carbon number 1 to 30.
According to this specification embodiment, R1 to R4 is same to each other or different to each other, and be each independently substitution or Unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl group, substituted or unsubstituted butyl, substitution or Unsubstituted amyl group, substituted or unsubstituted isopropyl or the substituted or unsubstituted tert-butyl group.
According to this specification embodiment, R1 to R4 is same to each other or different to each other, and is each independently methyl, second Base, propyl group, butyl, amyl group, isopropyl or the tert-butyl group.
According to this specification embodiment, R1 and R2 are substituted or unsubstituted methyl.
According to this specification embodiment, R1 and R2 are methyl.
According to this specification embodiment, R3 and R4 are hydrogen.
According to this specification embodiment, A1 and A2 are same to each other or different to each other, and to be selected from following structures It is any.
According to this specification embodiment, Z1 into Z3 at least one be N, remaining is same to each other or different to each other, and It is each independently N or CR.
According to this specification embodiment, X is NAr1, O or S.
According to this specification embodiment, X is NAr1.
According to this specification embodiment, X is O.
According to this specification embodiment, X is S.
According to this specification embodiment, Q for substituted or unsubstituted monocyclic or polycyclic aromatic ring or Substituted or unsubstituted monocyclic or polycyclic heterocycle.
According to this specification embodiment, Q is substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substitution Or unsubstituted anthracene, substituted or unsubstituted luxuriant and rich with fragrance or substituted or unsubstituted pyrene.
According to this specification embodiment, Q is benzene, naphthalene, anthracene, phenanthrene or pyrene.
According to this specification embodiment, Q is benzene.
According to this specification embodiment, Q is naphthalene.
According to this specification embodiment, L1 to L6 is same to each other or different to each other, and is each independently direct key Conjunction, substituted or unsubstituted arlydene or substituted or unsubstituted heteroarylidene.
According to this specification embodiment, L1 to L6 is same to each other or different to each other, and is each independently direct key Close.
According to this specification embodiment, L1 to L6 is same to each other or different to each other, and be each independently substitution or Unsubstituted arlydene.
According to this specification embodiment, L1 to L6 is same to each other or different to each other, and be each independently substitution or It is unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted sub- terphenyl, substituted or unsubstituted Naphthylene, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted Sanya phenyl, substitution Or unsubstituted sub- pyrenyl or substituted or unsubstituted fluorenylidene.
According to this specification embodiment, L1 to L6 is same to each other or different to each other, and be each independently phenylene, Biphenylene, sub- terphenyl, naphthylene, anthrylene, phenanthrylene, Sanya phenyl, sub- pyrenyl or fluorenylidene.
According to this specification embodiment, L1 to L6 is same to each other or different to each other, and is each independently phenylene.
According to this specification embodiment, L1 to L6 is same to each other or different to each other, and is each independently sub- biphenyl Base.
According to this specification embodiment, L1 to L6 is same to each other or different to each other, and is each independently anthrylene.
According to this specification embodiment, L1 to L6 is same to each other or different to each other, and is each independently naphthylene.
According to this specification embodiment, L1 to L6 is same to each other or different to each other, and be each independently substitution or Unsubstituted heteroarylidene.
According to this specification embodiment, L1 to L6 is same to each other or different to each other, and be each independently substitution or Unsubstituted divalent carbazyl, substituted or unsubstituted divalent dibenzo-carbazole base, substituted or unsubstituted divalent dibenzofurans Base, substituted or unsubstituted divalent dibenzothiophenes base, substituted or unsubstituted divalent pyridine radicals, substituted or unsubstituted divalent are phonetic Piperidinyl or substituted or unsubstituted divalent triazine radical.
According to this specification embodiment, L1 to L6 is same to each other or different to each other, and is each independently divalent carbazole Base, divalent dibenzo-carbazole base, divalent dibenzofuran group, divalent dibenzothiophenes base, divalent pyridine radicals, divalent pyrimidine radicals or divalent three Piperazine base.
According to this specification embodiment, Ar1 is substituted or unsubstituted aryl or substituted or unsubstituted Heteroaryl.
According to this specification embodiment, Ar1 is the aryl of substituted or unsubstituted carbon number 6 to 30.
According to this specification embodiment, Ar1 is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl Base, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substitution or unsubstituted Phenanthryl, substituted or unsubstituted triphenyl or substituted or unsubstituted fluorenyl.
According to this specification embodiment, Ar1 is phenyl.
According to this specification embodiment, Ar1 is xenyl.
According to this specification embodiment, Ar1 is terphenyl.
According to this specification embodiment, Ar1 is naphthyl.
According to this specification embodiment, Ar1 is the heteroaryl of substituted or unsubstituted carbon number 2 to 30.
According to this specification embodiment, Ar1 is substituted or unsubstituted pyridine radicals, substituted or unsubstituted phonetic Piperidinyl or substituted or unsubstituted triazine radical.
According to this specification embodiment, Ar1 is pyridine radicals, pyrimidine radicals or triazine radical.
According to this specification embodiment, Ar2 to Ar5 is same to each other or different to each other, and be each independently hydrogen, Deuterium, halogen group, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substitution or Unsubstituted aryl or substituted or unsubstituted heteroaryl.
According to this specification embodiment, Ar2 to Ar5 is same to each other or different to each other, and is each independently substitution Or the alkyl of unsubstituted carbon number 1 to 30.
According to this specification embodiment, Ar2 to Ar5 is same to each other or different to each other, and is each independently substitution Or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl or substituted or unsubstituted tertiary fourth Base.
According to this specification embodiment, Ar2 to Ar5 is same to each other or different to each other, and be each independently methyl, Ethyl, isopropyl or the tert-butyl group.
According to this specification embodiment, Ar2 to Ar5 is same to each other or different to each other, and is each independently substitution Or the aryl of unsubstituted carbon number 6 to 30.
According to this specification embodiment, Ar2 to Ar5 is same to each other or different to each other, and is each independently substitution Or unsubstituted phenyl, substituted or unsubstituted xenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthalene Base, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenyl or substitution do not take The fluorenyl in generation.
According to this specification embodiment, Ar2 to Ar5 is same to each other or different to each other, and is each independently phenyl.
According to this specification embodiment, Ar2 to Ar5 is same to each other or different to each other, and is each independently biphenyl Base.
According to this specification embodiment, Ar2 to Ar5 is same to each other or different to each other, and is each independently three Phenyl.
According to this specification embodiment, Ar2 to Ar5 is same to each other or different to each other, and is each independently naphthyl.
According to this specification embodiment, Ar2 to Ar5 is same to each other or different to each other, and is each independently substitution Or the heteroaryl of unsubstituted carbon number 2 to 30.
According to this specification embodiment, Ar2 to Ar5 is same to each other or different to each other, and is each independently substitution Or unsubstituted pyridine radicals, substituted or unsubstituted pyrimidine radicals or substituted or unsubstituted triazine radical.
According to this specification embodiment, Ar2 to Ar5 is same to each other or different to each other, and is each independently pyridine Base, pyrimidine radicals or triazine radical.
According to this specification embodiment, R and R5 to R10 are same to each other or different to each other, and be each independently hydrogen, Deuterium, halogen group, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted oxidation phosphino-, take Generation or unsubstituted aryl or substituted or unsubstituted heterocyclic radical.
According to this specification embodiment, R and R5 to R10 are same to each other or different to each other, and are each independently and take Generation or the aryl of unsubstituted carbon number 6 to 30.
According to this specification embodiment, R and R5 to R10 are same to each other or different to each other, and are each independently and take Generation or unsubstituted phenyl, substituted or unsubstituted xenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthalene Base, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenyl or substitution do not take The fluorenyl in generation.
According to this specification embodiment, R and R5 to R10 are same to each other or different to each other, and are each independently benzene Base.
According to this specification embodiment, R and R5 to R10 are same to each other or different to each other, and are each independently connection Phenyl.
According to this specification embodiment, R and R5 to R10 are same to each other or different to each other, and are each independently three Xenyl.
According to this specification embodiment, R and R5 to R10 are same to each other or different to each other, and are each independently naphthalene Base.
According to this specification embodiment, R and R5 to R9 are hydrogen.
According to this specification embodiment, R10 is the aryl of substituted or unsubstituted carbon number 6 to 30.
According to this specification embodiment, R10 is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl Base or substituted or unsubstituted naphthyl.
According to this specification embodiment, R10 is phenyl.
According to this specification embodiment, A1 and A2 are same to each other or different to each other, and can be each independently from What is selected in following structures is any.
According to this specification embodiment, the compound represented by above-mentioned chemical formula 1 is selected from following compounds Any of.
It can be manufactured according to the compound of this specification embodiment using following manufacture methods.Following manufactures In example, although describe representational example, but can add or delete as needed substituent, substituent can also be changed Position.In addition, 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-claimed cpd.
There is provided a kind of organic electronic element in one embodiment of this specification, wherein, including：First electrode and institute State that first electrode is opposed and the second electrode that possesses and possess 1 layer between above-mentioned first electrode and above-mentioned second electrode 1 layer of above-claimed cpd contained above in organic matter layer above, 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 there is a situation where other components between two components.
In this specification, when pointing out a certain inscape of certain a part of "comprising", as long as no especially opposite record, Then this means can further include other inscapes, rather than by except other inscapes.
The organic matter layer of the organic electronic 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 this specification, organic Light-emitting component can have comprising hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer, electronics resistance Barrier, hole blocking layer etc. as organic matter layer structure.But, the structure of organic electronic element is not limited to this, can wrap Containing the less organic layer of quantity.
According to this specification embodiment, above-mentioned organic electronic element can be selected from organic illuminating element, organic Phosphorescent element, organic solar batteries, Organophotoreceptor (OPC) and organic transistor.
Hereinafter, organic illuminating element is enumerated.
In one embodiment of this specification, above-mentioned organic matter layer includes luminescent layer, and above-mentioned luminescent layer includes above-mentionedization Compound represented by formula 1.
In one embodiment of this specification, above-mentioned organic matter layer includes luminescent layer, and above-mentioned luminescent layer includes above-mentionedization Compound represented by formula 1 as luminescent layer main body.
According to this specification embodiment, above-mentioned organic matter layer includes luminescent layer, and above-mentioned luminescent layer is comprising above-mentioned Compound represented by chemical formula 1 as luminescent layer phosphorescence host or fluorescent host.
In one embodiment of this specification, above-mentioned organic matter layer is made comprising the compound represented by above-mentioned chemical formula 1 For the main body of luminescent layer, dopant is used as comprising other organic compounds, metal or metallic compound.
In one embodiment of this specification, above-mentioned organic matter layer is made comprising the compound represented by above-mentioned chemical formula 1 For the main body of luminescent layer, dopant is used as comprising complex of iridium.
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 the compound represented by above-mentioned chemical formula 1.
In one embodiment of this specification, above-mentioned organic matter layer can include multiple hole transmission layers.
In one embodiment of this specification, above-mentioned organic matter layer includes electron transfer layer, electron injecting layer or simultaneously Carry out the layer of electron injection and transmission, above-mentioned electron transfer layer, electron injecting layer or carry out electron injection simultaneously and electronics is passed Defeated layer includes above-claimed cpd.
In one embodiment of this specification, above-mentioned organic matter layer can include multiple electron transfer layers.
In one embodiment of this specification, above-mentioned organic matter layer includes electronic barrier layer, above-mentioned electronic barrier layer bag Containing the compound represented by above-mentioned chemical formula 1.
In one embodiment of this specification, above-mentioned organic matter layer is further included to be passed selected from hole injection layer, hole Defeated layer, luminescent layer, electron transfer layer, electron injecting layer, electron injection and transport layer, hole blocking layer and electronic barrier layer In 1 layer or more than 2 layers.
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 It is at least one layer of in layer, above-mentioned more than 2 layers of organic matter layer to include above-claimed cpd.In one embodiment of this specification, on The organic matter layer for stating more than 2 layers can be from electron transfer layer, electron injecting layer, while carrying out electric transmission and electron injection Two or more is 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 It is at least one layer of in electron transfer layer above to include above-claimed cpd.Specifically, can in an embodiment of this specification Above-claimed cpd or above-mentioned more than 2 layers of electronics biography are included to be 1 layer in above-mentioned more than 2 layers of electron transfer layer Defeated 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, the hole injection layer or hole transmission layer further comprising the compound containing arylamino, carbazyl or benzo carbazole base.
In another embodiment, organic illuminating element can for 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, for example, can make With metal or metal complex.According to one, the electron transfer layer of the compound comprising above-mentioned chemical formula 1 can be included further LiQ。
In another embodiment, organic illuminating element can for 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 electronic 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 the exemplary architecture of the embodiment according to 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 is possible to use material known in the art and method are manufactured..
In the case that above-mentioned organic illuminating element includes multiple organic matter layers, 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 contained above, i.e. above-mentionedization in organic matter layer Beyond compound represented by formula 1, it is possible to use material known in the art and method are manufactured.
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 following manufacture：Utilize sputtering (sputtering) or electron-beam vapor deposition method (e-beam ) etc evaporation PVD (physical Vapor Deposition, physical vapour deposition (PVD)) method, steams on substrate Plate metal or conductive metal oxide or their alloy and form anode, then formed on the anode comprising sky Cave implanted layer, hole transmission layer, the organic matter layer of luminescent layer and electron transfer layer, are deposited on the organic matter layer can be used as afterwards The material of negative electrode.In addition to such method, also can on substrate evaporation cathode material, organic matter layer, anode material successively To manufacture organic illuminating element.
In addition, the compound on above-mentioned chemical formula 1, when manufacturing organic illuminating element, can not only be steamed using vacuum Plating method, can also form organic matter layer 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 the electroconductive polymer such as polyaniline etc., but it is not limited only to this.
As above-mentioned cathode substance, generally for enabling electronics easily to be injected to organic matter layer, preferably work function Small material.As the concrete example of cathode substance, there are the metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminium, silver, tin and lead Or their 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, as hole injecting material, is preferably followingization Compound：Possesses the ability of transporting holes, with the hole injection effect from anode, for the excellent of luminescent layer or luminescent material Hole injection effect, the exciton produced by preventing in luminescent layer migrates to electron injecting layer or electron injection material, and thin Film Forming ability is excellent.It is preferred that HOMO (the highest occupied molecular orbital, highest of hole injecting material Occupy molecular orbit) between the work function of anode material and the HOMO of surrounding organic matter layer.It is used as hole injecting material Concrete example, has metalloporphyrin (porphyrin), Oligopoly thiophene, aryl amine system organic matter, the azepine benzophenanthrene system of six nitrile six organic Thing, quinacridone (quinacridone) are that organic matter, perylenes (perylene) are organic matter, anthraquinone and polyaniline and polythiophene system Electroconductive polymer etc., but it 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, is the material that can be received the hole from anode or hole injection layer and transfer them to luminescent layer, empty Mobility big material in cave is suitable.As concrete example, there are aryl amine system organic matter, electroconductive polymer and while deposit In block copolymer of conjugate moiety and non-conjugated portion etc., but it is not limited only to this.
Above-mentioned electronic barrier layer be prevent from hole injection layer injected holes by luminescent layer enter electron injecting layer and The life-span of element and the layer of efficiency can be improved, if necessary, known material formation can be used in luminescent layer and electron injection Suitable part between layer.
Above-mentioned hole blocking layer be prevent from hole injection layer injected holes by luminescent layer enter electron injecting layer and The life-span of element and the layer of efficiency can be improved, if necessary, known material formation can be used in luminescent layer and electron injection Suitable part between layer.
In this specification, the organic matter layer beyond luminescent layer includes the compound or tool represented by above-mentioned chemical formula 1 It is to receive respectively from hole transmission layer as the luminescent substance of above-mentioned luminescent layer in the case of standby additional luminescent layer With the hole of electron transfer layer and electronics and combine it and send the material of the light of visible region, be preferably for fluorescence or The high material of the quantum efficiency of phosphorescence.As concrete example, there is 8-hydroxyquinoline aluminum complex (Alq3)；Carbazole based compound；Two 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) chemical combination Thing；Polyfluorene, rubrene 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 is carbazole derivates compound, dibenzofurans Derivative, 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, it is with substituted or unsubstituted arylamino as aromatic amine derivative Aromatic fused ring derivative, have the pyrene with arylamino, anthracene,Two indeno pyrenes (Periflanthene) etc., are used as benzene second Alkenyl amines, is the compound that substitution has at least one aryl vinyl on substituted or unsubstituted arylamine, selected from virtue 1 in base, silicyl, alkyl, cycloalkyl and arylamino or more than 2 substituents are substituted 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, making 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, is used as electronics Transport materials, are 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.In the case of specially caesium, barium, calcium, ytterbium and samarium, each material, along with aluminium lamination or Silver layer.
Above-mentioned electron injecting layer is the layer for the electronics that injection carrys out self-electrode, preferably following compound：With transmission electronics Ability, with the electron injection effect from negative electrode, for the excellent electron injection effect of luminescent layer or luminescent material, prevent Only exciton produced in luminescent layer is migrated to hole injection layer, and film Forming ability is excellent.Specifically, have Fluorenone, Anthraquinone bismethane (Anthraquinodimethane), diphenoquinone, thiopyrandioxide,Azoles,Diazole, triazole, imidazoles, Perylene tetracarboxylic 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 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.
The organic illuminating element of this specification according to used in material, can for 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 electrode or The compound represented by above-mentioned chemical formula 1 is included in organic transistor.
Similar principle when can also be by with applied to organic illuminating element according to the compound of this specification and apply In with the organic electronic element for representative such as Phosphorescent element, organic solar batteries, Organophotoreceptor, organic transistor. For example, above-mentioned organic solar batteries can live for the light arranged comprising negative electrode, anode and between above-mentioned negative electrode and anode Property layer structure, above-mentioned photoactive layer can include above-claimed cpd.
Hereinafter, in order to illustrate this specification, enumerate embodiment and comparative example etc. to describe in detail.However, this explanation The embodiment and comparative example of book can be changed to various other forms, and this specification scope will not be interpreted by with The embodiment of lower detailed description and the restriction of comparative example.The embodiment and comparative example of this specification be in order to those skilled in the art more Intactly illustrate this specification and provide.
<Production Example>
<Synthesis example 1>The manufacture of-intermediate 1
In a nitrogen atmosphere, chemical formula 1A (50g, 238mmol) is put into chloroform 500ml and stirred, be subsequently cooled to 0 ℃.Afterwards, N- bromo-succinimides (NBS) (93g, 523mol) are slowly added dropwise with solid state.React within 30 minutes Afterwards, temperature is promoted to normal temperature, further carries out reaction 2 hours, then heat, carried out stirring in 3 hours and flow back.Afterwards, drop Water is added dropwise after low temperature, then terminating reaction.Afterwards, organic layer is separated with water layer, then uses sodium thiosulfateSaturated solution is extracted 2 times.Organic layer is separated with water layer, then organic layer is utilized Magnesium sulfate is dried.Afterwards, organic layer is distilled, then recrystallizing by ethyl acetate and ethanol, manufactures intermediate 1 (69g, 79%).
<Synthesis example 2>The manufacture of-intermediate 2
In a nitrogen atmosphere, by above-mentioned intermediate 1 (69g, 188mmol), pinacol diborane (105g, 413mmol) and potassium acetate (111g, 1126mmol) are mixed, and are added in tetrahydrofuran 200ml, then while stirring Mix while heating.At reflux, be put into [1,1 '-bis- (diphenylphosphino) ferrocene] palladium chloride (II) (0.8g, 1.1mmol), carry out heating in 3 hours and stir.After reaction terminates, temperature is reduced to normal temperature and filtered.Added into filtrate Water, after chloroform recovery, organic layer is dried and vacuum distillation with anhydrous magnesium sulfate, then recrystallized with ethanol, made Make intermediate 2 (79g, 91%).
<Synthesis example 3>The manufacture of-compound 1
In a nitrogen atmosphere, chemical formula 3A (10g, 37mmol) and intermediate 2 (8.6g, 19mmol) are put into tetrahydrofuran (THF) in 100ml, it is stirred and flows back.Afterwards, by potassium carbonate (K2CO3) (16g, 112mmol) be dissolved in water (H2O)50ml After put into, be sufficiently stirred for, then put into tetra-triphenylphosphine palladium (TTP) (1.3g, 1mmol).Afterwards, carry out reacting for 12 hours, will Temperature is reduced to normal temperature, is then filtered.After filtrate chloroform and water are extracted, organic layer is dried with magnesium sulfate.It Afterwards, by organic layer vacuum distillation, recrystallized using ethyl acetate.Dried after the solid generated is filtered, manufactureization Compound 1 (10g, 81%).
MS[M+H]+=672
<Synthesis example 4>The manufacture of-compound 2
In a nitrogen atmosphere, chemical formula 4A (10g, 37mmol) and intermediate 2 (8.6g, 19mmol) are put into tetrahydrofuran (THF) in 100ml, it is stirred and flows back.Afterwards, by potassium carbonate (K2CO3) (16g, 112mmol) be dissolved in water (H2O)50ml After put into, be sufficiently stirred for, then put into tetra-triphenylphosphine palladium (TTP) (1.3g, 1mmol).Afterwards, carry out reacting for 12 hours, will Temperature is reduced to normal temperature, is then filtered.After filtrate chloroform and water are extracted, organic layer is dried with magnesium sulfate.It Afterwards, by organic layer vacuum distillation, recrystallized using ethyl acetate.Dried after the solid generated is filtered, manufactureization Compound 2 (9g, 71%).
MS[M+H]+=670
<Synthesis example 5>The manufacture of-compound 3
In a nitrogen atmosphere, chemical formula 5A (10g, 37mmol) and intermediate 2 (8.6g, 19mmol) are put into tetrahydrofuran (THF) in 100ml, it is stirred and flows back.Afterwards, by potassium carbonate (K2CO3) (16g, 112mmol) be dissolved in water (H2O)50ml After put into, be sufficiently stirred for, then put into tetra-triphenylphosphine palladium (TTP) (1.3g, 1mmol).Afterwards, carry out reacting for 12 hours, will Temperature is reduced to normal temperature, is then filtered.After filtrate chloroform and water are extracted, organic layer is dried with magnesium sulfate.It Afterwards, by organic layer vacuum distillation, recrystallized using ethyl acetate.Dried after the solid generated is filtered, manufactureization Compound 3 (9.5g, 75%).
MS[M+H]+=670
<Synthesis example 6>The manufacture of-compound 4
In a nitrogen atmosphere, chemical formula 6A (10g, 37mmol) and intermediate 2 (6g, 13mmol) are put into tetrahydrofuran (THF) in 100ml, it is stirred and flows back.Afterwards, by potassium carbonate (K2CO3) (11g, 77mmol) be dissolved in water (H2O)50ml After put into, be sufficiently stirred for, then put into tetra-triphenylphosphine palladium (TTP) (1.3g, 1mmol).Afterwards, carry out reacting for 12 hours, will Temperature is reduced to normal temperature, is then filtered.After filtrate chloroform and water are extracted, organic layer is dried with magnesium sulfate.It Afterwards, by organic layer vacuum distillation, recrystallized using ethyl acetate.Dried after the solid generated is filtered, manufactureization Compound 4 (11g, 70%).
MS[M+H]+=824
<Synthesis example 7>The manufacture of-compound 5
In a nitrogen atmosphere, chemical formula 7A (10g, 35mmol) and intermediate 2 (8g, 17.2mmol) are put into tetrahydrofuran (THF) in 100ml, it is stirred and flows back.Afterwards, by potassium carbonate (K2CO3) (14g, 103mmol) be dissolved in water (H2O)50ml After put into, be sufficiently stirred for, then put into tetra-triphenylphosphine palladium (TTP) (1.2g, 1mmol).Afterwards, carry out reacting for 12 hours, will Temperature is reduced to normal temperature, is then filtered.After filtrate chloroform and water are extracted, organic layer is dried with magnesium sulfate.It Afterwards, by organic layer vacuum distillation, recrystallized using ethyl acetate.Dried after the solid generated is filtered, manufactureization Compound 5 (9g, 60%).
MS[M+H]+=672
<Synthesis example 8>The manufacture of-compound 6
In a nitrogen atmosphere, chemical formula 8A (10g, 47mmol) and intermediate 2 (11g, 23mmol) are put into tetrahydrofuran (THF) in 100ml, it is stirred and flows back.Afterwards, by potassium carbonate (K2CO3) (19g, 140mmol) be dissolved in (H2O) after 60ml Input, is sufficiently stirred for, and then puts into tetra-triphenylphosphine palladium (TTP) (1.6g, 1mmol).Afterwards, carry out reacting for 12 hours, by temperature Degree is reduced to normal temperature, is then filtered.After filtrate chloroform and water are extracted, organic layer is dried with magnesium sulfate.Afterwards, By organic layer vacuum distillation, recrystallized using ethyl acetate.Dried after the solid generated is filtered, manufacture compound 6 (9g, 70%).
MS[M+H]+=566
<Synthesis example 9>The manufacture of-compound 7
In a nitrogen atmosphere, by intermediate 1 (11.0g, 30mmol), chemical formula 8A (carbazole) (10g, 60mmol) and tertiary fourth Sodium alkoxide (12g, 120mmol) is put into dimethylbenzene (xylene) 100ml, is stirred and is flowed back.Afterwards, double (three tertiary fourths are put into Base phosphine) palladium (0.6g, 1.2mmol).Carry out after reaction in 8 hours, temperature is reduced to normal temperature and filtered.By above-mentioned filtrate chlorine After imitative and water is extracted, organic layer is dried with magnesium sulfate.Afterwards, by after organic layer vacuum distillation, column chromatography (chloroform is utilized：Oneself Alkane) it is refined, then concentrate is recrystallized with chloroform and ethyl acetate again.Dried after the solid generated is filtered, Manufacture compound 7 (13g, 60%).
MS[M+H]+=540
<Synthesis example 10>The manufacture of-compound 8
In a nitrogen atmosphere, by above-mentioned intermediate 1 (8.5g, 23mmol), chemical formula 9A (10g, 46mmol) and the tert-butyl alcohol Sodium (9g, 92mmol) is put into dimethylbenzene (xylene) 100ml, is stirred and is flowed back.Afterwards, put into double (tri-butyl phosphines) Palladium (0.5g, 1mmol).Carry out after reaction in 8 hours, temperature is reduced to normal temperature and filtered.By above-mentioned filtrate chloroform and water After extraction, organic layer is dried with magnesium sulfate.Afterwards, by after organic layer vacuum distillation, column chromatography (chloroform is utilized：Hexane) essence System, is then recrystallized concentrate with chloroform and ethyl acetate again.Dried after the solid generated is filtered, manufactureization Compound 8 (8g, 50%).
MS[M+H]+=640
<Synthesis example 11>The manufacture of-compound 9
In a nitrogen atmosphere, chemical formula 11A (10g, 44mmol) and intermediate 2 (14g, 22mmol) are put into tetrahydrofuran (THF) in 100ml, it is stirred and flows back.Afterwards, by potassium carbonate (K2CO3) (18g, 130mmol) be dissolved in water (H2O)60ml After put into, be sufficiently stirred for, then put into tetra-triphenylphosphine palladium (TTP) (0.3g, 0.2mol).Afterwards, carry out reacting for 12 hours, will Temperature is reduced to normal temperature, is then filtered.After filtrate chloroform and water are extracted, organic layer is dried with magnesium sulfate.It Afterwards, by organic layer vacuum distillation, recrystallized using ethyl acetate.Dried after the solid generated is filtered, manufactureization Compound 9 (9g, 71%).
MS[M+H]+=594
<Embodiment>
<Experimental example 1-1>
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 by Millipore Corp. (Millipore Co.) manufacture filter (Filter) filter 2 times after distillation Water.After ITO is washed 30 minutes, the ultrasonic washing for carrying out 10 minutes 2 times repeatedly with distilled water.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 the azepine benzophenanthrene of six nitrile six (hexanitrile hexaazatriphenylene, HAT) and form hole injection layer.Vacuum is steamed over the hole-injecting layer Plating is used as the material of transporting holesAfterwards, withThickness vacuum evaporation main body H1 and dopant D1 Compound is used as luminescent layer.With 1 on above-mentioned luminescent layer:1 weight is than the He of compound 1 that is manufactured in vacuum evaporation synthesis example 3 LiQ (Lithium Quinolate, quinoline lithium) and formedThe electron injection and transport layer of thickness.In above-mentioned electronics note Enter and transport layer on be deposited successivelyThe lithium fluoride (LiF) of thickness andThe aluminium of thickness and form negative electrode, so as to make Make organic illuminating element.
In said process, the evaporation rate of organic matter maintain 0.4 toThe lithium fluoride of negative electrode is maintainedEvaporation rate, aluminium maintainEvaporation rate, during evaporation vacuum maintain 2 × 10-7To 5 × 10- 6Torr, so as to make organic illuminating element.
[HT1]
<Experimental example 1-2 to 1-9>
In above-mentioned experimental example 1-1, as electron injection and transport layer, compound 1 is replaced using compound 2 to 9, except this with Outside, similarly tested.
<Comparative example 1-1>
In above-mentioned experimental example 1-1, using following ET1 compound replace compound 1, in addition, using with above-mentioned reality Test a 1-1 identicals method and make organic illuminating element.
[ET1]
<Comparative example 1-2>
In above-mentioned experimental example 1-1, using ET2 compound replace compound 1, in addition, using with above-mentioned experimental example 1-1 identicals method makes organic illuminating element.
[ET2]
<Comparative example 1-3>
In above-mentioned experimental example 1-1, using ET3 compound replace compound 1, in addition, using with above-mentioned experimental example 1-1 identicals method makes organic illuminating element.
[ET3]
<Comparative example 1-4>
In above-mentioned experimental example 1-1, using ET4 compound replace compound 1, in addition, using with above-mentioned experimental example 1-1 identicals method makes organic illuminating element.
[ET4]
For using each compound as electron injection as above-mentioned experimental example 1-1 to 1-8 and comparative example 1-1 to 1-4 And transport layer material and the organic illuminating element that manufactures, in 10mA/cm2Current density under determine driving voltage and luminous effect Rate, in 20mA/cm2Current density under determine time (LT when reaching the 95% of original intensity95).It the results are shown in following In table 1.
[table 1]
As shown in Table 1 above, it is known that noted in the compound represented by the chemical formula 1 to 8 using this specification as electronics Enter and transport layer and in the case of the organic illuminating element that manufactures, in the efficiency of organic illuminating element, driving voltage and/or stably Property aspect show excellent characteristic.
In addition, as shown in Table 1 above, it is known that in the compound 9 and comparative example 1-4 ET4 compounds using this specification In the case of the organic illuminating element manufactured as electron injection and transport layer, efficiency, the driving voltage class of organic light emission member Seemingly, but in terms of stability excellent characteristic is shown, it follows that compared with substitution has the situation of alkyl on imidazoles, taking In generation, shows more excellent life characteristic in the case of having aryl.
By above content, the preferred experimental example (electron injection and transport layer) of the present invention is illustrated, but this Invention is not limited by this, and can carry out various changes in the range of right and the embodiment of invention Implement after shape, this falls within scope of the invention.

Claims (8)

1. a kind of compound, it is represented by following chemical formula 1,
Chemical formula 1
In the chemical formula 1,
R1 to R4 is same to each other or different to each other, and is each independently hydrogen, deuterium, halogen group, substituted or unsubstituted alkyl, substitution Or unsubstituted cycloalkyl, substituted or unsubstituted oxidation phosphino-, substituted or unsubstituted aryl or substituted or unsubstituted Heteroaryl,
A is 1 to 3 integer,
B is 1 to 3 integer,
When a is more than 2, multiple R3 are same to each other or different to each other,
When b is more than 2, multiple R4 are same to each other or different to each other,
A1 and A2 are same to each other or different to each other, and any for what is selected from following structures,
Z1 into Z3 at least one be N, remaining is same to each other or different to each other, and is each independently N or CR,
X be NAr1, O or S,
Q be substituted or unsubstituted monocyclic or polycyclic aromatic ring or substituted or unsubstituted monocyclic or polycyclic heterocycle,
L1 to L6 is same to each other or different to each other, and is each independently Direct Bonding, substituted or unsubstituted arlydene or substitution Or unsubstituted heteroarylidene,
Ar1 be substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl,
Ar2 to Ar5 is same to each other or different to each other, and is each independently hydrogen, deuterium, halogen group, substituted or unsubstituted alkyl, takes Generation or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl or substituted or unsubstituted miscellaneous Aryl,
R and R5 to R10 is same to each other or different to each other, and be each independently hydrogen, deuterium, halogen group, substituted or unsubstituted alkyl, Substituted or unsubstituted cycloalkyl, substituted or unsubstituted oxidation phosphino-, substituted or unsubstituted aryl or substitution do not take The heterocyclic radical in generation,
R5 is 1 to 4 integer,
R6 is 1 to 4 integer,
R7 is 1 to 4 integer,
R8 is 1 to 2 integer,
R9 is 1 to 4 integer,
R10 is 1 to 6 integer,
When r5 is more than 2, multiple R5 are same to each other or different to each other,
When r6 is more than 2, multiple R6 are same to each other or different to each other,
When r7 is more than 2, multiple R7 are same to each other or different to each other,
When r8 is 2, multiple R8 are same to each other or different to each other,
When r9 is more than 2, multiple R9 are same to each other or different to each other,
When r10 is more than 2, multiple R10 are same to each other or different to each other.
2. compound according to claim 1, wherein, the compound represented by chemical formula 1 is selected from following chemical combination Any of thing,
3. a kind of organic electronic element, wherein, including：First electrode, it is opposed with the first electrode and possess second electrode, And possess in more than 1 layer of organic matter layer between the first electrode and the second electrode, the organic matter layer 1 Compound described in layer claim 1 or 2 contained above.
4. organic electronic element according to claim 3, wherein, the organic matter layer includes luminescent layer, the luminescent layer Include the compound.
5. organic electronic element according to claim 3, wherein, the organic matter layer is passed comprising hole injection layer or hole Defeated layer, the hole injection layer or hole transmission layer include the compound.
6. organic electronic element according to claim 3, wherein, the organic matter layer is noted comprising electron transfer layer, electronics Enter layer or carry out the layer of electron injection and electric transmission simultaneously, the electron transfer layer, electron injecting layer or enter simultaneously The layer of row electron injection and electric transmission includes the compound.
7. organic electronic element according to claim 3, wherein, the organic matter layer hinders comprising electronic barrier layer or hole Barrier, the electronic barrier layer or hole blocking layer include the compound.
8. organic electronic element according to claim 3, wherein, the organic electronic element also include selected from luminescent layer, Hole injection layer, hole transmission layer, electron transfer layer, electron injecting layer, electron injection and transport layer, electronic barrier layer and 1 layer in hole blocking layer or more than 2 layers.
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