CN107973786A - New compound and utilize its organic illuminating element - Google Patents

New compound and utilize its organic illuminating element Download PDF

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Publication number
CN107973786A
CN107973786A CN201710995225.9A CN201710995225A CN107973786A CN 107973786 A CN107973786 A CN 107973786A CN 201710995225 A CN201710995225 A CN 201710995225A CN 107973786 A CN107973786 A CN 107973786A
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compound
layer
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CN107973786B (en
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文程昱
郑珉祐
李东勋
朴胎润
赵圣美
李征夏
李周泳
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LG Chem Ltd
LG Corp
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LG Chemical Co Ltd
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Abstract

The present invention provides the compound represented by chemical formula 1 and utilizes its organic illuminating element.In formula, X1For O or S, Y1To Y3For N or CR3, Y1To Y3In it is at least one be N, L1And L2For key, C6‑60Arlydene or C2‑60Heteroarylidene, Ar1And Ar2For C6‑60Aryl or C2‑60Heteroaryl, Ar3For N (Ar11)(Ar12) or C2‑60Heteroaryl, with L2With reference to atom be hetero atom, Ar11And Ar12For C6‑60Aryl or C2‑60Heteroaryl, R1To R3For hydrogen, deuterium, halogen, cyano group, amino, C1‑60Alkyl, C1‑60Haloalkyl, C1‑60Alkoxy, C1‑60Halogenated alkoxy, C3‑60Cycloalkyl, C2‑60Alkenyl, C6‑60Aryl, C6‑60Aryloxy group or C2‑60Heterocyclic radical, a1 and a2 are 0 to 3 integer.Chemical formula 1

Description

New compound and utilize its organic illuminating element
Technical field
Mutual with related application is quoted
This application claims the korean patent application the 10-2016-0139260th based on October 25th, 2016 and 2017 The priority of year September korean patent application of 29 days the 10-2017-0128262nd, includes public in the korean patent application document The full content as part of this specification opened.
The present invention relates to a kind of new compound and the organic illuminating element for including it.
Background technology
Under normal conditions, organic light emission phenomenon refers to the phenomenon for making electric energy be converted to luminous energy using organic substance.Using having The organic illuminating element of machine luminescence phenomenon have wide viewing angle, excellent contrast, fast response time, brightness, driving voltage and Response speed excellent, so as to largely be studied.
Organic illuminating element usually has the organic matter comprising anode and cathode and between above-mentioned anode and cathode The structure of layer.In order to improve the efficiency of organic illuminating element and stability, often formed by utilizing each different materials Sandwich construction forms organic matter layer, for example, can be by hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electronics The formation such as implanted layer.It is empty if applying voltage between two electrodes for the structure of such organic illuminating element Cave is injected into organic matter layer from anode, and electronics is injected into organic matter layer from cathode, the meeting when institute's injected holes and electronics meet Exciton (exciton) is formed, and light will be sent when the exciton transits to ground state again.
It is lasting to require exploitation new material for the organic matter used in organic illuminating element as described above.
The content of the invention
The present invention relates to a kind of new compound and the organic illuminating element for including it.
The present invention provides the compound represented by following chemical formula 1：
[chemical formula 1]
In above-mentioned chemical formula 1,
X1For O or S,
Y1To Y3It is each independently N or CR3, Y1To Y3In it is at least one be N,
L1And L2It is each independently key, substituted or unsubstituted C6-60Arlydene or substituted or unsubstituted include one Heteroatomic C more than a in O, N, Si and S2-60Heteroarylidene,
Ar1And Ar2It is each independently substituted or unsubstituted C6-60Aryl or substituted or unsubstituted include 1 extremely 3 heteroatomic C in N, O and S2-60Heteroaryl,
Ar3For N (Ar11)(Ar12) or it is substituted or unsubstituted include 1 to 3 it is heteroatomic in N, O and S C2-60Heteroaryl, with above-mentioned L2With reference to atom be hetero atom,
Wherein, Ar11And Ar12It is each independently substituted or unsubstituted C6-60Aryl or substituted or unsubstituted bag Heteroatomic C containing 1 to 3 in N, O and S2-60Heteroaryl,
R1To R3It is each independently hydrogen, deuterium, halogen, cyano group, amino, substituted or unsubstituted C1-60Alkyl, C1-60Halo Alkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C1-60Halogenated alkoxy, substituted or unsubstituted C3-60 Cycloalkyl, substituted or unsubstituted C2-60Alkenyl, substituted or unsubstituted C6-60Aryl, substituted or unsubstituted C6-60Aryloxy group, It is or substituted or unsubstituted comprising moreing than one the heteroatomic C in N, O and S2-60Heterocyclic radical,
A1 and a2 is each independently 0 to 3 integer.
In addition, the present invention a kind of organic illuminating element is provided comprising：It is first electrode, opposed with above-mentioned first electrode And the second electrode that possesses and possess more than one layer of organic matter layer between above-mentioned first electrode and second electrode, on State one in organic matter layer layer of compound contained above represented by above-mentioned chemical formula 1.
The compound represented by above-mentioned chemical formula 1 can as the materials'use of the organic matter layer of organic illuminating element, So as to realize the raising of efficiency, low driving voltage and/or the raising of life characteristic in organic illuminating element.Especially, The compound represented by above-mentioned chemical formula 1 can be used as hole injection, hole transport, hole injection and transmission, shine, electronics Transmission or electron injection material use.
Brief description of the drawings
Fig. 1 illustrates the example for the organic illuminating element being made of substrate 1, anode 2, luminescent layer 3, cathode 4.
Fig. 2 is illustrated by substrate 1, anode 2, hole injection layer 5, hole transmission layer 6, luminescent layer 7,8 and of electron transfer layer The example for the organic illuminating element that cathode 4 is formed.
Brief description of the drawings
1：Substrate 2：Anode
3：Luminescent layer 4：Cathode
5：Hole injection layer 6：Hole transmission layer
7：Luminescent layer 8：Electron transfer layer.
Embodiment
In the following, in order to help to understand the present invention, illustrate in more detail.
In this specification,Represent the key being connected with other substituents, singly-bound refers to that the part represented by L is not present The situation of other atom.
" substituted or unsubstituted " this term refers in this specification, by selected from deuterium, halogen group, cyano group, nitro, hydroxyl Base, carbonyl, ester group, imide, amino, oxidation phosphino-, alkoxy, aryloxy group, alkyl sulfenyl ( Alkyl thioxy), artyl sulfo ( Aryl thioxy), alkyl sulfoxide base ( Alkyl sulfoxy), aryl sulfoxid es base (Aryl sulfoxy), silicyl, boryl, alkyl, ring Alkyl, alkenyl, aryl, aralkyl, arylalkenyl, alkylaryl, alkyl amine group, aralkyl amido, heteroaryl amido, arylamine Base, aryl phosphino- or comprising in the more than one heterocyclic radical in N, O and S atom more than one substituent substitution or not Substitution, or the substituent being formed by connecting by the substituent of more than 2 in foregoing illustrative substituent substitute or unsubstituted.Example Such as, " substituent that the substituent of more than 2 is formed by connecting " can be xenyl.That is, xenyl can be aryl, can also solve It is interpreted as the substituent that 2 phenyl are formed by connecting.
In this specification, the carbon number of carbonyl is not particularly limited, but preferably carbon number is 1 to 40.Specifically, Can be the compound of structure as described below, but it's not limited to that.
In this specification, for ester group, oxygen atom in ester group can by the straight chain of carbon number 1 to 25, side chain or The aryl of cyclic alkyl or carbon number 6 to 25 substitutes.Specifically, can be the compound of following structural formula, but it is and unlimited Due to this.
In this specification, the carbon number of imide is not particularly limited, but preferably carbon number is 1 to 25.Specifically For, can be the compound of following structure, but it's not limited to that.
In this specification, silicyl specifically has trimethyl silyl, triethylsilyl, tertbutyldimethylsilyl chloride Silylation, vinyldimethylsilyl, propyl-dimethyl silicyl, triphenyl-silyl, diphenylsilyl group, Phenyl silyl groups etc., but it's not limited to that.
In this specification, boryl specifically has trimethyl boryl, triethyl group boryl, fert-butyidimethylsilyl boryl, triphenyl borine Base, phenyl boryl etc., but it's not limited to that.
In this specification, as the example of halogen group, there are fluorine, chlorine, bromine or iodine.
In this specification, abovementioned alkyl can be straight or branched, and carbon number is not particularly limited, but preferably 1 to 40.According to an embodiment, the carbon number of abovementioned alkyl is 1 to 20.According to another embodiment, the carbon atom of abovementioned alkyl Number is 1 to 10.According to another embodiment, the carbon number of abovementioned alkyl is 1 to 6.As the specific example of alkyl, there is first Base, ethyl, propyl group, n-propyl, isopropyl, butyl, normal-butyl, isobutyl group, the tert-butyl group, sec-butyl, 1- methyl-butvls, 1- second Base-butyl, 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, cyclopentyl-methyl, hexamethylene Ylmethyl, octyl group, n-octyl, t-octyl, 1- methylheptyls, 2- ethylhexyls, 2- propylpentyls, n-nonyl, 2,2- dimethyl Heptyl, 1- Ethyl-propyls, 1,1- Dimethyl-propyls, isohesyl, 2- methyl amyls, 4- methylhexyls, 5- methylhexyls etc., but It's not limited to that.
In this specification, above-mentioned alkenyl can be straight or branched, and carbon number is not particularly limited, but preferably 2 to 40.According to an embodiment, the carbon number of above-mentioned alkenyl is 2 to 20.According to another embodiment, the carbon atom of above-mentioned alkenyl Number is 2 to 10.According to another embodiment, the carbon number of above-mentioned alkenyl is 2 to 6.As concrete example, there are vinyl, 1- third Alkenyl, isopropenyl, 1- cyclobutenyls, 2- cyclobutenyls, 3- cyclobutenyls, 1- pentenyls, 2- pentenyls, 3- pentenyls, 3- methyl isophthalic acids- Cyclobutenyl, 1,3- butadiene, pi-allyl, 1- phenylethylene -1- bases, 2- phenylethylene -1- bases, 2,2- talan -1- bases, 2- Double (hexichol -1- bases) ethene -1- bases, Stilbene base, styryls of phenyl -2- (naphthalene -1- bases) ethene -1- bases, 2,2- etc., but it is and unlimited Due to this.
In this specification, cycloalkyl is not particularly limited, but the preferably cycloalkyl of carbon number 3 to 60, real according to one Mode is applied, the carbon number of above-mentioned cycloalkyl is 3 to 30.According to another embodiment, the carbon number of above-mentioned cycloalkyl for 3 to 20.According to another embodiment, the carbon number of above-mentioned cycloalkyl is 3 to 6.Specifically, there are cyclopropyl, cyclobutyl, ring penta Base, 3- methylcyclopentyls, 2,3- dimethylcyclopentyls, cyclohexyl, 3- methylcyclohexyls, 4- methylcyclohexyls, 2,3- dimethyl Cyclohexyl, 3,4,5- trimethylcyclohexyls, 4- tert-butylcyclohexyls, suberyl, cyclooctyl etc., but it's not limited to that.
In this specification, aryl is not particularly limited, but the preferably aryl of carbon number 6 to 60, can be monocyclic virtue Base or polyaromatic.According to an embodiment, the carbon number of above-mentioned aryl is 6 to 30.According to an embodiment, above-mentioned aryl Carbon number be 6 to 20.Can be phenyl, xenyl, terphenyl etc. as monocyclic aryl on above-mentioned aryl, but simultaneously It is not limited to this.As above-mentioned polyaromatic, can be naphthyl, anthryl, phenanthryl, pyrenyl, base,Base, fluorenyl etc., but not It is defined in this.
In this specification, fluorenyl can be substituted, and 2 substituents can be bonded to each other and form spiro structure.In above-mentioned fluorenes In the case of base is substituted, Ke Yiwei
Deng.But it's not limited to that.
In this specification, heterocyclic radical is as heteroatomic heterocyclic radical, carbon atom comprising more than one in O, N, Si and S Number is not particularly limited, but preferably carbon number is 2 to 60.As the example of heterocyclic radical, have thienyl, furyl, pyrrole radicals, Imidazole radicals, thiazolyl,Oxazolyl,Di azoly, triazolyl, pyridine radicals, bipyridyl, pyrimidine radicals, triazine radical, acridinyl, rattle away Piperazine base, pyrazinyl, quinolyl, quinazolyl, quinoxalinyl, phthalazinyl, Pyridopyrimidine base, pyrido-pyrazine base, pyrazine are simultaneously Pyrazinyl, isoquinolyl, indyl, carbazyl, benzoOxazolyl, benzimidazolyl, benzothiazolyl, benzo carbazole base, benzene It is bithiophene base, dibenzothiophene, benzofuranyl, phenanthroline (phenanthroline), differentOxazolyl, thiadiazolyl group, Phenothiazinyl and dibenzofuran group etc., but it's not limited to that.
In this specification, the example phase of aryl and above-mentioned aryl in aralkyl, arylalkenyl, alkylaryl, arylamine group Together.In this specification, the alkyl in aralkyl, alkylaryl, alkyl amine group is identical with the example of abovementioned alkyl.This specification In, the heteroaryl in heteroaryl amine can apply with respect to the explanation of above-mentioned heterocyclic radical.In this specification, alkenyl in arylalkenyl with The example of above-mentioned alkenyl is identical.In this specification, arlydene is divalent group, in addition, can be applicable in above-mentioned on aryl Explanation.In this specification, heteroarylidene is divalent group, in addition, can be applicable in the above-mentioned explanation on heterocyclic radical.This In specification, hydrocarbon ring is not 1 valency group, and is that 2 substituents are combined into, and in addition, can be applicable in above-mentioned on virtue The explanation of base or cycloalkyl.In this specification, heterocycle is not 1 valency group, and is that 2 substituents are combined into, in addition, The above-mentioned explanation on heterocyclic radical can be applicable in.
In addition, the present invention provides the compound represented by a kind of above-mentioned chemical formula 1.
In above-mentioned chemical formula 1,
Y1And Y2For N, Y3For CR3；Or
Y1And Y3For N, Y2For CR3；Or
Y1、Y2And Y3Can be N.
For example,
Y1And Y2For N, Y3For CH；Or
Y1And Y3For N, Y2For CH；Or
Y1、Y2And Y3Can be N.
In addition, L1And L2Can be key, substituted or unsubstituted phenylene, substituted or unsubstituted biphenyl independently of one another Alkenyl or substituted or unsubstituted naphthylene.
For example, L1And L2Can be key or any one in following radicals independently of one another:
Specifically, such as L1And L2Can be key or any one in following radicals independently of one another:
In addition, Ar1And Ar2Can be any one in following radicals independently of one another:
In above-mentioned,
Z1And Z2It is each independently hydrogen, deuterium, halogen group, cyano group, amino, C1-20Alkyl, C1-20Haloalkyl or C6-20 Aryl,
C1 and c2 is each independently 0 to 3 integer..
Wherein, Z1And Z2Can be hydrogen or phenyl independently of one another, c1 and c2 can be 0 or 1 independently of one another.
For example, Ar1And Ar2Can be any one in following radicals independently of one another:
In addition, Ar3For N (Ar11)(Ar12) or it is substituted or unsubstituted include 1 to 3 it is miscellaneous in N, O and S The C of atom2-60Heteroaryl, with above-mentioned L2The atom of bonding can be hetero atom, can be N more specifically.
More specifically, above-mentioned Ar3Can be any one in following radicals:
In above-mentioned group,
X2And X3It is each independently O, S, NZ13Or CZ14Z15,
Ar11And Ar12It is each independently substituted or unsubstituted C6-20Aryl or substituted or unsubstituted include 1 To 3 heteroatomic C in N, O and S2-20Heteroaryl,
Z11To Z15It is each independently hydrogen, deuterium, halogen, cyano group, amino, C1-20Alkyl, C1-20Haloalkyl or C6-20Virtue Base,
N1 and n2 is each independently 0 to 3 integer.
Wherein, Ar11And Ar12For phenyl, Z11To Z15Can be independently of one another hydrogen, methyl or phenyl, n1 and n2 are each Can be independently 0 or 1.
For example, Ar3Can be any one in following radicals:
In addition, R1To R3Can be hydrogen, deuterium, halogen group, cyano group, amino, methyl or phenyl independently of one another, a1 and a2 Can be 0 or 1 independently of one another.
For example, R1To R3Can be hydrogen.
At this moment, a1 represents R1Number, a1 be more than 2 when, the R of more than 21It may be same to each other or different to each other.For a2, The explanation of c1, c2, n1 and n2 are referred to understand the explanation of above-mentioned a1 and the structure of above-mentioned chemical formula.
In addition, above-claimed cpd can be any one in following compounds：
Compound represented by above-mentioned chemical formula 1 has to be connected in the specific location of dibenzofurans or the core of dibenzothiophenes The structure for being connected to the 6 circle heterocycles bases comprising more than one N atom and Ar3 substituents as described above and being formed, should so as to utilize The organic illuminating element of compound can have high efficiency, low driving voltage, high brightness and long-life etc..
Compound represented by above-mentioned chemical formula 1 can be manufactured for example, by the manufacture method of following reaction equations.Above-mentioned system The method of making can further embody in Production Example described later.
[reaction equation 1]
In above-mentioned reaction equation 1,
A and E is each independently the halogen groups such as chlorine, bromine,
D contains for such as boronate, boric acid ester group or pinacol borate (boronic acid pinacol ester) base Boron (B) organic group,
X1、Y1To Y3、L1、L2、R1、R2、a1And a2It is as defined above.
Specifically, the compound (I) of above-mentioned chemical formula 1 can be manufactured by the following method manufacture.Above-mentioned manufacture method Including：Make above-mentioned organoboron compound (II) in the presence of alkali and palladium series catalyst, it is even to carry out Suzuki with above-mentioned halide (III) The step of connection reacts and manufactures the compound of chemical formula (IV) (S1)；And make the compound and chemistry of above-mentioned chemical formula (IV) The step of compound of formula (V) is reacted (S2).
The compound for manufacturing above-mentioned chemical formula (IV) the step of in (S1), as above-mentioned alkali, carbonic acid can be used Sodium, potassium carbonate, sodium hydroxide or potassium hydroxide etc., in addition, as above-mentioned palladium series catalyst, can use tetrakis triphenylphosphine palladium (Pd(PPH3)4), acid chloride etc..In addition, above-mentioned reaction can be in tetrahydrofuran (THF), n,N-Dimethylformamide (DMF), two Implement in the organic solvent such as methyl sulfoxide (DMSO) or toluene.
In addition, above-mentioned Suzuki coupling reaction can be implemented in 80 DEG C to 120 DEG C scopes.
In addition, the compound for manufacturing above-mentioned chemical formula (I) the step of in (S2), or can also be in such as Pd (Pt- Bu3)2[M (Pt- such as (double (tri-butyl phosphine) palladiums (0), Bis (tri-tert-butylphosphine) palladium (0)) Bu3)2] (M=Pd, Pt) catalyst in the presence of, implement in the nonpolar solvents such as dimethylbenzene.In addition, during above-mentioned reaction, may be used also To add alkali, specifically, the non-nucleophilic such as NaOt-Bu (sodium tert-butoxide, Sodium terc-butoxide) can also be added Alkali.
With reference to the structure of above-mentioned reaction equation 1 and chemical formula 1, by suitably replace being used as initial substance compound (II) and Compound (III) and compound (V), so as to manufacture the organometallic represented by the above-mentioned chemical formula 1 for wanting manufacture Compound (I).
In addition, the present invention provides the organic illuminating element for including the compound represented by above-mentioned chemical formula 1.As an example, The present invention a kind of organic illuminating element is provided comprising：First electrode, it is opposed with above-mentioned first electrode and possess second Electrode and possesses more than 1 layer of organic matter layer between above-mentioned first electrode and above-mentioned second electrode, above-mentioned organic matter layer In one layer of above-mentioned chemical formula 1 contained above represented by compound.
The organic matter layer of organic illuminating element of the present invention can be formed by single layer structure, can also by be laminated with two layers with On the sandwich construction of organic matter layer formed.For example, the organic illuminating element of the present invention, which can have, includes hole injection layer, sky The structure as organic matter layer such as cave transport layer, luminescent layer, electron transfer layer, electron injecting layer.But organic illuminating element It's not limited to that for structure, can include the organic layer of fewer layers.
In addition, above-mentioned organic matter layer include hole injection layer, hole transmission layer or be carried out at the same time hole injection and transmission Layer, above-mentioned hole injection layer, hole transmission layer or be carried out at the same time hole injection and transmission layer include above-mentioned chemical formula 1 represented by Compound.
In addition, above-mentioned organic matter layer can include luminescent layer, above-mentioned luminescent layer can be included represented by above-mentioned chemical formula 1 Compound.
Furthermore it is possible to comprising above-mentioned electron transfer layer, electron injecting layer or it is carried out at the same time electric transmission and electron injection Layer, above-mentioned electron transfer layer, electron injecting layer or is carried out at the same time electric transmission and the layer of electron injection and can include above-mentioned chemistry Compound represented by formula 1.
In addition, above-mentioned organic matter layer includes luminescent layer and electron transfer layer, above-mentioned electron transfer layer can include above-mentionedization Compound represented by formula 1.
The organic matter layer of organic illuminating element of the present invention can be formed by single layer structure, can also by be laminated with two layers with On the sandwich construction of organic matter layer formed.For example, the organic illuminating element of the present invention can have in addition to luminescent layer also Comprising the hole injection layer and hole transmission layer between above-mentioned first electrode and above-mentioned luminescent layer, and above-mentioned luminescent layer with it is above-mentioned The structure of electron transfer layer and electron injecting layer as organic matter layer between second electrode.But the knot of organic illuminating element It's not limited to that for structure, can include the organic layer of less or more layer.
In addition, the organic illuminating element of the present invention can be that anode, more than one layer organic are sequentially laminated with substrate The organic illuminating element of nitride layer and the structure of cathode (standard type (normal type)).In addition, the organic light emission member of the present invention Part can be the reverse structure (inversion type that cathode, more than one layer of organic matter layer and anode are sequentially laminated with substrate (inverted type)) organic illuminating element.For example, the knot of the organic illuminating element involved by one embodiment of the invention Structure is illustrated in Fig. 1 and Fig. 2.
Fig. 1 illustrates the example for the organic illuminating element being made of substrate 1, anode 2, luminescent layer 3, cathode 4.In this knot In structure, the compound represented by above-mentioned chemical formula 1 may be embodied in above-mentioned luminescent layer.
Fig. 2 is illustrated by substrate 1, anode 2, hole injection layer 5, hole transmission layer 6, luminescent layer 7,8 and of electron transfer layer The example for the organic illuminating element that cathode 4 is formed.In this configuration, the compound represented by above-mentioned chemical formula 1 can include In more than 1 layer in above-mentioned hole injection layer, hole transmission layer, luminescent layer and electron transfer layer.
For organic illuminating element according to the present invention, 1 layer of above-mentioned chemistry contained above in above-mentioned organic matter layer Compound represented by formula 1, in addition, can be manufactured by material known to the technical field and method.In addition, above-mentioned have In the case that machine light-emitting component includes multiple organic matter layers, above-mentioned organic matter layer can be by identical material or different material shapes Into.
For example, the present invention organic illuminating element can by stacked gradually on substrate first electrode, organic matter layer with And second electrode and manufacture.At this moment, can manufacture as follows：Utilize sputtering (sputtering) or electron-beam vapor deposition method (e-beam ) etc evaporation PVD (physical Vapor Deposition：Physical vapor deposition method) method, steamed 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 then deposited on organic matter layer and can be used as The material of cathode and manufacture.In addition to this method, can also on substrate evaporation cathode material, organic matter layer, sun successively Pole material and manufacture organic illuminating element.
In addition, the compound represented on above-mentioned chemical formula 1, when manufacturing organic illuminating element, can not only utilize true Empty vapour deposition method, can also form organic matter layer using solution coating method.Here, so-called solution coating method refers to, spin-coating method, leaching Coating, knife coating, ink jet printing method, silk screen print method, spray-on process, rolling method etc., but it's not limited to that.
In addition to this method, can on substrate successively evaporation cathode material, organic matter layer, anode material and manufacture Organic illuminating element (WO 2003/012890).But it's not limited to that for manufacture method.
As an example, above-mentioned first electrode is anode, and above-mentioned second electrode is cathode；Or above-mentioned first electrode is Cathode, above-mentioned second electrode are anode.
It is preferably work function generally for enabling hole successfully to be injected to organic matter layer as above-mentioned anode material Big material.As the concrete example of above-mentioned anode material, there are the metals such as vanadium, chromium, copper, zinc, gold or their alloy；Zinc oxide, The metal oxides such as indium oxide, tin indium oxide (ITO), indium zinc oxide (IZO)；ZnO:Al or SNO2:The metals such as Sb and oxide Combination；Poly- (3 methyl thiophene), poly- [3,4- (ethylidene -1,2- dioxies) thiophene] (PEDOT), polypyrrole and polyaniline etc. are led Electrical macromolecule etc., but it's not limited to that.
It is preferably that work function is small generally for making electronics easily be injected to organic matter layer as above-mentioned cathode substance Material.As the concrete example of above-mentioned 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's not limited to that.
Above-mentioned hole injection layer is the layer in the hole that injection carrys out self-electrode, is preferably followingization as hole injecting material Compound：Possess the ability of transporting holes, there is the hole injection effect from anode, for the excellent of luminescent layer or luminescent material Hole injection effect, prevent in luminescent layer caused exciton to be migrated to electron injecting layer or electron injection material, and thin Film Forming ability is excellent.It is preferred that HOMO (highest occupied molecular orbital(HOMO), the highest occupied of hole injecting material Molecular orbital) between the work function of anode material and the HOMO of surrounding organic matter layer.As hole infusion The concrete example of matter, has metalloporphyrin (porphyrin), Oligopoly thiophene, aryl amine system organic matter, six nitriles, six azepine benzophenanthrene system 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 it's not limited to that.
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 that can receive the hole from anode or hole injection layer and transfer them to the material of luminescent layer, right The material that the mobility in hole is big is suitable.As concrete example, there are aryl amine system organic matter, electroconductive polymer, Yi Jitong When there are block copolymer of conjugate moiety and non-conjugated portion etc., but it's not limited to that.
It is that can receive hole and electronics respectively from hole transmission layer and electron transfer layer and make as above-mentioned luminescent substance They with reference to and send the material of the light of visible region, preferably for the high material of the quantum efficiency of fluorescence or phosphorescence.As Concrete example, there is 8- Hydroxy-quinolin aluminum complexes (Alq3)；Carbazole based compound；Two polystyrene-based (dimerized Styryl) compound；BAlq；10- hydroxy benzo quinoline metal compounds；BenzoAzoles, benzothiazole and benzimidazole system Compound；Poly- (to phenylenevinylenes) (PPV) is macromolecule；Loop coil (spiro) compound；Polyfluorene, rubrene etc., but it is and unlimited Due to this.
Above-mentioned luminescent layer can include material of main part and dopant material as described above.Material of main part is except above-mentioned chemical formula Beyond compound represented by 1, aromatic fused ring derivative or nitrogen-containing heterocgcies etc. can also be further included.It is specific and Speech, as aromatic fused ring derivative, there is anthracene derivant, pyrene derivatives, naphthalene derivatives, pentacene derivative, phenanthrene compound, glimmering Anthracene compound etc., as nitrogen-containing heterocgcies, there is carbazole derivates, dibenzofuran derivative, ladder type furan compoundPyrimidine derivatives etc., but it's not limited to that.
More specifically, following compounds (H2) can be by 10:90 to 90:10 mixing ratio is used in mixed way, it is more specific and Speech, can be by 40:60 to 60:40 mixing ratio is used in mixed way.
As dopant material, have aromatic amine derivative, styrylamine compounds, boron complexes, fluoranthene compound, Metal complex etc..Specifically, it is the aromatic series with substituted or unsubstituted arylamino as aromatic amine derivative Fused-ring derivatives, have the pyrene with arylamino, anthracene,, two indeno pyrenes (Periflanthene) etc., as styryl amine Compound, is that substitution has the compound of at least one aryl vinyl on substituted or unsubstituted arylamine, by selected from aryl, One or more substituent substitution or unsubstituted in silicyl, alkyl, cycloalkyl and arylamino.It is specific and Speech, has styryl amine, styryl diamines, styryl triamine, styryl tetramine etc., but it's not limited to that.In addition, As metal complex, there are complex of iridium, platinum complex etc., but it's not limited to that.
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, are that can receive electronics well from cathode and transfer them to the material of luminescent layer, big to the mobility of electronics Material be suitable.As concrete example, there are the Al complexs of 8-hydroxyquinoline, comprising Alq3Complex, organic free radical Compound, hydroxyl brass-metal complex etc., but it's not limited to that.Electron transfer layer can be as used in the prior art As be used together with the cathode substance of any desired.Particularly, the example of suitable cathode substance is with low work function And with aluminium lamination or the common material of silver layer.Specifically, it is caesium, barium, calcium, ytterbium and samarium, for each material, and aluminium Layer or silver layer accompany.
Above-mentioned electron injecting layer is the layer for the electronics that injection carrys out self-electrode, is preferably following compound：With transmission electronics Ability, have the electron injection effect from cathode, the excellent electron injection effect for luminescent layer or luminescent material, prevent Only caused exciton is migrated to hole injection layer in luminescent layer, and film Forming ability is excellent.Specifically, have Fluorenone, Anthraquinone bismethane (Anthraquinodimethane), diphenoquinone, thiopyrandioxide,Azoles,Diazole, triazole, imidazoles, Tetrabasic carboxylic acid, fluorenylidene-methane, anthrone etc. and their derivative, metal complex and nitrogenous 5 membered ring derivatives etc., but simultaneously It is 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) (o-cresol) gallium, double (2- methyl -8- quinoline) (1- naphthols) aluminium, double (2- methyl -8- quinoline) (beta naphthals) Gallium etc., but it's not limited to that.
The organic illuminating element of the present invention can be top emission type, bottom emission type or double according to used material To light emitting-type.
In addition, the compound represented by above-mentioned chemical formula 1 in addition to organic illuminating element, be further included in it is organic too Positive energy battery or organic transistor.
Compound represented by above-mentioned chemical formula 1 and the manufacture comprising its organic illuminating element have in the examples below Illustrate body.But following embodiments are illustrative for the present invention, it's not limited to that for the scope of the present invention.
[Production Example]
Production Example 1：The compound of synthetic intermediate A1 and A2
(1) manufacture of intermediate A 1
Under nitrogen atmosphere, in 2000mL round-bottomed flasks, by 2- iodobenzene -1,3- glycol (2-iodobenzene-1,3- Diol) (100g, 0.42mol) and (the chloro- 2- fluorophenyls of 3-) boric acid ((3-chloro-2-fluorophenyl) boronic Acid after) (81.3g, 0.47mol) is dissolved in the tetrahydrofuran of 1000mL, addition be dissolved in water 500ml potassium carbonate (175g, 1.27mol) aqueous solution, then adds double (tri-butyl phosphine) palladium (0) (Bis (tri-tert-butylphosphine) Palladium (0)) after (2.17g, 4.23mmol), when heating stirring 1 is small.Room temperature is cooled the temperature to, then separates water removal Layer, after then being dried with anhydrous magnesium sulfate, is concentrated under reduced pressure, and is then recrystallized using hexane, is dry, so as to manufacture above-mentioned intermediate A1 (80.2g, yield 79%, MS:[M+H]+=239).
(2) manufacture of intermediate A 2
Intermediate A 1 (80.2g, 0.33mol) and potassium carbonate (139g, 1.01mol) are dissolved in the N- methyl -2- pyrroles of 400mL After pyrrolidone (N-methyl-2-pyrrolidone), when heating stirring 1 is small.Room temperature is cooled the temperature to, anti-precipitationInto water and filter.After being completely dissolved in dichloromethane, it is washed with water, after being dried with anhydrous magnesium sulfate, decompression is dense Contracting, is recrystallized using ethanol, is dry, so as to manufacture above-mentioned intermediate A 2 (53.2g, yield 72%, MS:[M+H]+=219).
Production Example 2：The compound of synthetic intermediate A3 and A4
(1) manufacture of intermediate A 3
After intermediate A 2 (53.2g, 0.23mol) is dissolved in acetonitrile (Acetonitrile) 75mL, by calcium carbonate After (47.3g, 0.34mol) is dissolved in the water of 100mL, nine fluorine butane sulfuryl fluorides are slowly added dropwise at 0 DEG C (nonafluorobutanesulfonyl fluoride) (45.2mL, 0.25mol) 25 minutes.Then, it is small that 3 are stirred at room temperature When.Filter, after being then completely dissolved in dichloromethane, be washed with water after reaction, after being dried with anhydrous magnesium sulfate, decompression is dense Contracting, is recrystallized using ethanol, is dry, so as to manufacture above-mentioned intermediate A 3 (83.3g, yield 73%, MS:[M+H]+=501).
(2) manufacture of intermediate A 4
By intermediate A 3 (83.3g, 0.17mol), 4,4,5,5- tetramethyls-[1,3,2]-dioxaborinate (4,4,5,5- tetramethyl-[1,3,2]-dioxaboralane)(46.5g,0.18mol)、Pd(dppf)Cl2(1.22g, 1.66mmol), KOAc (49.0g, 0.50mol) is added to the two of 900mLIn alkane (dioxane), then under reflux conditions Stir 10 it is small when.Room temperature is cooled the temperature to, is then concentrated under reduced pressure to solvent.Concentrate is completely dissolved in CHCl3Afterwards, water is used Washing, to the solution decompression concentration dissolved with product, is then purified, so as to obtain intermediate A 4, (95.2g, is received using column chromatography Rate 86%, MS:[M+H]+=329).
Production Example 3：The compound of synthetic intermediate A5
By intermediate A 4 (30.0g, 0.09mol) and the chloro- 4,6- diphenyl triazine (2-chloro-4,6-diphenyl- of 2- 1,3,5-triazine) after (24.4g, 0.091mmol) is dissolved in the tetrahydrofuran of 300mL, the carbonic acid for the water for being dissolved in 120mL is added Potassium (37.9g, 0.27mol), after adding tetrakis triphenylphosphine palladium (1.05g, 0.91mmol), when heating stirring 9 is small.By temperature After being down to room temperature, separate except water layer, after then being dried with anhydrous magnesium sulfate, be concentrated under reduced pressure, utilize dichloro-benzenes (dichlorobenzene) recrystallize, is dry, so as to manufacture above-mentioned intermediate A 5 (32.1g, yield 81%, MS:[M+H]+ =433).
Production Example 4：The compound of synthetic intermediate A6
Use the chloro- 4- of 2- (dibenzo [b, d] furans -4- bases) -6- phenyl -1,3,5- triazines (2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine) chloro- 4, the 6- diphenyl triazines of 2- are replaced, except this In addition, intermediate A 6 has been manufactured by the identical method of the method with manufacturing intermediate A 5.
Production Example 5：The compound of synthetic intermediate A7
Use the chloro- 4- of 2- (dibenzo [b, d] furans -1- bases) -6- phenyl -1,3,5- triazines (2-chloro-4- (dibenzo [b, d] furan-1-yl) -6-phenyl-1,3,5-triazine) chloro- 4, the 6- diphenyl triazines of 2- are replaced, except this In addition, intermediate A 7 is manufactured by the identical method of the method with manufacturing intermediate A 5.
Production Example 6：The compound of synthetic intermediate A8
Use the chloro- 4- of 2- (dibenzo [b, d] furans -2- bases) -6- phenyl -1,3,5- triazines (2-chloro-4- (dibenzo [b, d] furan-2-yl) -6-phenyl-1,3,5-triazine) chloro- 4, the 6- diphenyl triazines of 2- are replaced, except this In addition, intermediate A 8 is manufactured by the identical method of the method with manufacturing intermediate A 5.
Production Example 7：The compound of synthetic intermediate A9
Use the chloro- 4- of 2- (dibenzo [b, d] furans -3- bases) -6- phenyl -1,3,5- triazines (2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine) chloro- 4, the 6- diphenyl triazines of 2- are replaced, except this In addition, intermediate A 9 is manufactured by the identical method of the method with manufacturing intermediate A 5.
Production Example 8：The compound of synthetic intermediate A10
Use the chloro- 4- of 2- (dibenzo [b, d] thiophene -4- bases) -6- phenyl -1,3,5- triazines (2-chloro-4- (dibenzo [b, d] thiophen-4-yl) -6-phenyl-1,3,5-triazine) chloro- 4, the 6- diphenyl triazines of 2- are replaced, In addition, intermediate A 10 is manufactured by the identical method of the method with manufacturing intermediate A 5.
Production Example 9：The compound of synthetic intermediate A11
Use the chloro- 4- of 2- (dibenzo [b, d] thiene-3-yl) -6- phenyl -1,3,5- triazines (2-chloro-4- (dibenzo [b, d] thiophen-3-yl) -6-phenyl-1,3,5-triazine) chloro- 4, the 6- diphenyl triazines of 2- are replaced, In addition, intermediate A 11 is manufactured by the identical method of the method with manufacturing intermediate A 5.
Production Example 10：The compound of synthetic intermediate A12
Use 2- (4- bromophenyls) -4,6- diphenyl -1,3,5- triazines (2- (4-bromophenyl) -4,6- Diphenyl-1,3,5-triazine) chloro- 4, the 6- diphenyl triazines of 2- are replaced, in addition, by with manufacturing intermediate A 5 The identical method manufacture intermediate A 12 of method.
Production Example 11：The compound of synthetic intermediate A13
Use 2- (3- bromophenyls) -4,6- diphenyl -1,3,5- triazines (2- (3-bromophenyl) -4,6- Diphenyl-1,3,5-triazine) chloro- 4, the 6- diphenyl triazines of 2- are replaced, in addition, by with manufacturing intermediate A 5 The identical method manufacture intermediate A 13 of method.
Production Example 12：The compound of synthetic intermediate A14
The chloro- 4,6- of 2- are replaced using the chloro- 4,6- diphenylpyrimidins (2-chloro-4,6-diphenylpyrimidine) of 2- Diphenyl triazine, in addition, intermediate A 14 is manufactured by the identical method of the method with manufacturing intermediate A 5.
Production Example 13：The compound of synthetic intermediate A15
The chloro- 4,6- of 2- are replaced using the chloro- 2,6- diphenylpyrimidins (4-chloro-2,6-diphenylpyrimidine) of 4- Diphenyl triazine, in addition, intermediate A 15 is manufactured by the identical method of the method with manufacturing intermediate A 5.
[embodiment]
Embodiment 1：The synthesis of compound 1
Under nitrogen atmosphere, by intermediate A 5 (10.0g, 0.023mol) and diphenylamines (3.90g, 0.19mol), double (three uncles Butyl phosphine) palladium (0) (Bis (tri-tert-butylphosphine) palladium (0)) (0.12g, 0.23mmol), tert-butyl alcohol Sodium (sodium tert-butoxide) (3.32g, 0.035mol) is added in the dimethylbenzene of 110ml, when heating stirring 9 is small. Room temperature is cooled the temperature to, after filtering off desalination, paraxylene is concentrated under reduced pressure, and then utilizes dichloro-benzenes (dichlorobenzene) after dissolving, after being washed with water, MgSO is used4Go to remove water and remove solvent.Then, N- methyl -2- is utilized Pyrrolidones recrystallizes, so as to manufacture above-claimed cpd 1.(9.2g, yield 70%, MS:[M+H]+=567)
Embodiment 2：The synthesis of compound 2
Hexichol is replaced using two ([1,1 '-xenyl] -4- bases) amine (di ([1,1'-biphenyl] -4-yl) amine) Amine, in addition, compound 2 has been manufactured by the identical method of the method with manufacturing compound 1.(yield 74%, MS:[M+H ]+=719)
Embodiment 3：The synthesis of compound 3
Use N- ([1,1 '-xenyl] -4- bases) -9,9- dimethyl -9H- fluorenes -2- amine) (N- ([1,1'-biphenyl] - Diphenylamines 4-yl) -9,9-dimethyl-9H-fluoren-2-amine) is replaced, in addition, by with manufacturing compound 1 The identical method of method has manufactured compound 3.(yield 72%, MS:[M+H]+=759)
Embodiment 4：The synthesis of compound 4
Diphenylamines is replaced using 9H- carbazoles, in addition, is manufactured by the identical method of the method with manufacturing compound 1 Compound 4.(yield 72%, MS:[M+H]+=565)
Embodiment 5：The synthesis of compound 5
Replace diphenylamines using 7H- benzos [c] carbazole (7H-benzo [c] carbazole), in addition, by with system The method that the method for good fortune compound 1 is identical has manufactured compound 5.(yield 77%, MS:[M+H]+=615)
Embodiment 6：The synthesis of compound 6
Use 7,7- dimethyl -5,7- dihydros indeno [2,1-b] carbazoles (7,7-dimethyl-5,7-dihydroindeno [2,1-b] carbazole) diphenylamines is replaced, in addition, manufactured by the identical method of the method with manufacturing compound 1 Compound 6.(yield 80%, MS:[M+H]+=681)
Embodiment 7：The synthesis of compound 7
Use 12,12- dimethyl -11,12- dihydros indeno [2,1-a] carbazoles (12,12-dimethyl-11,12- Dihydroindeno [2,1-a] carbazole replaces diphenylamines, in addition, identical by the method with manufacturing compound 1 Method manufactured compound 7.(yield 82%, MS:[M+H]+=681)
Embodiment 8：The synthesis of compound 8
Use 11- phenyl -11,12- dihydros indeno [2,3-a] carbazoles (11-phenyl-11,12-dihydroindolo [2,3-a] carbazole) diphenylamines is replaced, in addition, manufactured by the identical method of the method with manufacturing compound 1 Compound 8.(yield 82%, MS:[M+H]+=730)
Embodiment 9：The synthesis of compound 9
Use 5- phenyl -5,12- dihydros indeno [3,2-a] carbazoles (5-phenyl-5,12-dihydroindolo [3,2- A] carbazole) diphenylamines is replaced, in addition, compound is manufactured by the identical method of the method with manufacturing compound 1 9.(yield 79%, MS:[M+H]+=730)
Embodiment 10：The synthesis of compound 10
Intermediate A 5 is replaced using intermediate A 6, in addition, passes through the identical method system of the method with manufacturing compound 1 Compound 10 is made.(yield 74%, MS:[M+H]+=657)
Embodiment 11：The synthesis of compound 11
Use intermediate A 6 and N- phenyl-[1,1'- xenyls] -4- amine (N-phenyl- [1,1'-biphenyl] -4- Amine intermediate A 5 and diphenylamines) are replaced, in addition, change has been manufactured by the identical method of the method with manufacturing compound 1 Compound 11.(yield 75%, MS:[M+H]+=733)
Embodiment 12：The synthesis of compound 12
Intermediate A 5 and diphenylamines are replaced using intermediate A 6 and 9H- carbazoles, in addition, by with manufacturing compound 1 The identical method of method manufactured compound 12.(yield 77%, MS:[M+H]+=655)
Embodiment 13：The synthesis of compound 13
Intermediate A 5 and two is replaced using intermediate A 6 and 11H- benzos [a] carbazole (11H-benzo [a] carbazole) Aniline, in addition, compound 13 has been manufactured by the identical method of the method with manufacturing compound 1.(yield 82%, MS:[M +H]+=705)
Embodiment 14：The synthesis of compound 14
Use intermediate A 6 and 7,7- dimethyl -5,7- dihydros indeno [2,1-b] carbazoles (7,7-dimethyl-5,7- Dihydroindeno [2,1-b] carbazole) intermediate A 5 and diphenylamines are replaced, in addition, by with manufacturing compound 1 The identical method of method manufactured compound 14.(yield 84%, MS:[M+H]+=771)
Embodiment 15：The synthesis of compound 15
Use intermediate A 6 and 12- phenyl -5,12- indoline simultaneously [3,2-a] carbazole (12-phenyl-5,12- Dihydroindolo [3,2-a] carbazole) intermediate A 5 and diphenylamines are replaced, in addition, by with manufacturing compound 1 The identical method of method manufactured compound 15.(yield 84%, MS:[M+H]+=820)
Embodiment 16：The synthesis of compound 16
Intermediate A 5 is replaced using intermediate A 7, in addition, passes through the identical method system of the method with manufacturing compound 1 Compound 16 is made.(yield 71%, MS:[M+H]+=657)
Embodiment 17：The synthesis of compound 17
Use intermediate A 7 and N- ([1,1'- xenyls] -4- bases)-[1,1'- xenyls] -3- amine (N- ([1,1'- Biphenyl] -4-yl)-[1,1'-biphenyl] -3-amine) replace intermediate A 5 and diphenylamines, in addition, by with The method that the method for manufacture compound 1 is identical has manufactured compound 17.(yield 74%, MS:[M+H]+=809)
Embodiment 18：The synthesis of compound 18
Intermediate A 5 and diphenylamines are replaced using intermediate A 7 and 9H- carbazoles, in addition, by by with manufacturing chemical combination The method that the method for thing 1 is identical has manufactured compound 18.(yield 77%, MS:[M+H]+=657)
Embodiment 19：The synthesis of compound 19
Intermediate A 5 and hexichol are replaced using intermediate A 7 and 7H- benzos [c] carbazole (7H-benzo [c] carbazole) Amine, in addition, compound 19 has been manufactured by the identical method of the method with manufacturing compound 1.(yield 79%, MS:[M+ H]+=705)
Embodiment 20：The synthesis of compound 20
Use intermediate A 7 and 7,7- dimethyl -5,7- dihydros indeno [2,1-b] carbazoles (7,7-dimethyl-5,7- Dihydroindeno [2,1-b] carbazole) intermediate A 5 and diphenylamines are replaced, in addition, by with manufacturing compound 1 The identical method of method manufactured compound 20.(yield 83%, MS:[M+H]+=771)
Embodiment 21：The synthesis of compound 21
Use intermediate A 7 and 5- phenyl -5,12- dihydros indeno [3,2-a] carbazoles (5-phenyl-5,12- Dihydroindolo [3,2-a] carbazole) intermediate A 5 and diphenylamines are replaced, in addition, by with manufacturing compound 1 The identical method of method manufactured compound 21.(yield 83%, MS:[M+H]+=820)
Embodiment 22：The synthesis of compound 22
Use intermediate A 8 and two ([1,1'- xenyls] -4- bases) amine (di ([1,1'-biphenyl] -4-yl) amine) Instead of intermediate A 5 and diphenylamines, in addition, compound is manufactured by the identical method of the method with manufacturing compound 1 22.(yield 73%, MS:[M+H]+=809)
Embodiment 23：The synthesis of compound 23
Intermediate A 5 and diphenylamines are replaced using intermediate A 8 and 9H- carbazoles, in addition, by with manufacturing compound 1 The identical method of method manufactured compound 23.(yield 72%, MS:[M+H]+=655)
Embodiment 24：The synthesis of compound 24
Intermediate A 5 and hexichol are replaced using intermediate A 8 and 5H- benzos [b] carbazole (5H-benzo [b] carbazole) Amine, in addition, compound 24 has been manufactured by the identical method of the method with manufacturing compound 1.(yield 79%, MS:[M+ H]+=705)
Embodiment 25：The synthesis of compound 25
Use intermediate A 8 and 7,7- dimethyl -7,12- dihydros indeno [1,2-a] carbazoles (7,7-dimethyl-7,12- Dihydroindeno [1,2-a] carbazole) intermediate A 5 and diphenylamines are replaced, in addition, by with manufacturing compound 1 The identical method of method manufactured compound 25.(yield 79%, MS:[M+H]+=771)
Embodiment 26：The synthesis of compound 26
Use intermediate A 8 and 12- phenyl -5,12- dihydros indeno [3,2-a] carbazoles (12-phenyl-5,12- Dihydroindolo [3,2-a] carbazole) intermediate A 5 and diphenylamines are replaced, in addition, by with manufacturing compound 1 The identical method of method manufactured compound 26.(yield 85%, MS:[M+H]+=820)
Embodiment 27：The synthesis of compound 27
Use intermediate A 8 and 13,13- dimethyl -11,13- dihydrobenzopyrans simultaneously [3,2-b] carbazole (13,13- Dimethyl-11,13-dihydrochromeno [3,2-b] carbazole) intermediate A 5 and diphenylamines are replaced, in addition, Compound 27 has been manufactured by the identical method of the method with manufacturing compound 1.(yield 80%, MS:[M+H]+=787)
Embodiment 28：The synthesis of compound 28
Use intermediate A 9 and N- ([1,1'- xenyls] -4- bases) -9,9- dimethyl -9H- fluorenes -2- amine (N- ([1,1'- Biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine) replace intermediate A 5 and diphenylamines, except this with Outside, compound 28 has been manufactured by the identical method of the method with manufacturing compound 1.(yield 77%, MS:[M+H]+=849)
Embodiment 29：The synthesis of compound 29
Using intermediate A 9 and 12,12- dimethyl -5,12- dihydros indeno [1,2-c] carbazole (12,12-dimethyl-5, 12-dihydroindeno [1,2-c] carbazole) intermediate A 5 and diphenylamines are replaced, in addition, by with manufacturing chemical combination The identical method of the method for thing 1, has manufactured compound 29.(yield 79%, MS:[M+H]+=771)
Embodiment 30：The synthesis of compound 30
Use intermediate A 9 and 12- phenyl -5,12- dihydros indeno [3,2-a] carbazoles (12-phenyl-5,12- Dihydroindolo [3,2-a] carbazole) intermediate A 5 and diphenylamines are replaced, in addition, by with manufacturing compound 1 The identical method of method manufactured compound 30.(yield 80%, MS:[M+H]+=820)
Embodiment 31：The synthesis of compound 31
Use intermediate A 9 and 13,13- dimethyl -7,13- dihydrobenzopyrans simultaneously [2,3-b] carbazole (13,13- Dimethyl-7,13-dihydrochromeno [2,3-b] carbazole) intermediate A 5 and diphenylamines are replaced, in addition, Compound 31 has been manufactured by the identical method of the method with manufacturing compound 1.(yield 82%, MS:[M+H]+=787)
Embodiment 32：The synthesis of compound 32
Use intermediate A 10 and two ([1,1'- xenyls] -4- bases) amine (di ([1,1'-biphenyl] -4-yl) Amine intermediate A 5 and diphenylamines) are replaced, in addition, change has been manufactured by the identical method of the method with manufacturing compound 1 Compound 32.(yield 73%, MS:[M+H]+=825)
Embodiment 33：The synthesis of compound 33
Intermediate A 5 and hexichol are replaced using intermediate A 10 and 5H- benzos [b] carbazole (5H-benzo [b] carbazole) Amine, in addition, compound 33 has been manufactured by the identical method of the method with manufacturing compound 1.(yield 77%, MS:[M+ H]+=721)
Embodiment 34：The synthesis of compound 34
Use intermediate A 10 and 11,11- dimethyl -5,11- dihydros indeno [1,2-b] carbazoles (11,11-dimethyl- 5,11-dihydroindeno [1,2-b] carbazole) replace intermediate A 5 and diphenylamines, in addition, by with manufactureization The method that the method for compound 1 is identical has manufactured compound 34.(yield 75%, MS:[M+H]+=787)
Embodiment 35：The synthesis of compound 35
Use intermediate A 10 and 5- phenyl -5,12- dihydros indeno [3,2-a] carbazoles (5-phenyl-5,12- Dihydroindolo [3,2-a] carbazole) intermediate A 5 and diphenylamines are replaced, in addition, by with manufacturing compound 1 The identical method of method manufactured compound 35.(yield 79%, MS:[M+H]+=836)
Embodiment 36：The synthesis of compound 36
Use intermediate A 11 and N- phenyl-[1,1'- xenyls] -4- amine (N-phenyl- [1,1'-biphenyl] -4- Amine intermediate A 5 and diphenylamines) are replaced, in addition, change has been manufactured by the identical method of the method with manufacturing compound 1 Compound 36.(yield 70%, MS:[M+H]+=749)
Embodiment 37：The synthesis of compound 37
Intermediate A 5 and diphenylamines are replaced using intermediate A 11 and 9H- carbazoles, in addition, by with manufacturing compound 1 The identical method of method manufactured compound 37.(yield 73%, MS:[M+H]+=671)
Embodiment 38：The synthesis of compound 38
Use intermediate A 11 and 7,7- dimethyl -5,7- dihydros indeno [2,1-b] carbazoles (7,7-dimethyl-5,7- Dihydroindeno [2,1-b] carbazole) intermediate A 5 and diphenylamines are replaced, in addition, by with manufacturing compound 1 The identical method of method manufactured compound 38.(yield 76%, MS:[M+H]+=787)
Embodiment 39：The synthesis of compound 39
Use intermediate A 11 and 8,8- dimethyl -5,8- dihydros indeno [2,1-c] carbazoles (8,8-dimethyl-5,8- Dihydroindeno [2,1-c] carbazole) intermediate A 5 and diphenylamines are replaced, in addition, by with manufacturing compound 1 The identical method of method manufactured compound 39.(yield 79%, MS:[M+H]+=787)
Embodiment 40：The synthesis of compound 40
Use intermediate A 11 and 5- phenyl -5,12- dihydros indeno [3,2-a] carbazoles (5-phenyl-5,12- Dihydroindolo [3,2-a] carbazole) intermediate A 5 and diphenylamines are replaced, in addition, by with manufacturing compound 1 The identical method of method manufactured compound 40.(yield 77%, MS:[M+H]+=836)
Embodiment 41：The synthesis of compound 41
Intermediate A 5 is replaced using intermediate A 12, in addition, passes through the identical method of the method with manufacturing compound 1 Compound 41 is manufactured.(yield 69%, MS:[M+H]+=643)
Embodiment 42：The synthesis of compound 42
Use intermediate A 12 and N- ([1,1'- xenyls] -4- bases)-[1,1'- xenyls] -3- amine (N- ([1,1'- Biphenyl] -4-yl)-[1,1'-biphenyl] -3-amine) replace intermediate A 5 and diphenylamines, in addition, by with The method that the method for manufacture compound 1 is identical has manufactured compound 42.(yield 75%, MS:[M+H]+=795)
Embodiment 43：The synthesis of compound 43
Intermediate A 5 and diphenylamines are replaced using intermediate A 12 and 9H- carbazoles, in addition, by with manufacturing compound 1 The identical method of method manufactured compound 43.(yield 74%, MS:[M+H]+=641)
Embodiment 44：The synthesis of compound 44
Use intermediate A 12 and 7,7- dimethyl -5,7- dihydros indeno [2,1-b] carbazoles (7,7-dimethyl-5,7- Dihydroindeno [2,1-b] carbazole) intermediate A 5 and diphenylamines are replaced, in addition, by with manufacturing compound 1 The identical method of method manufactured compound 44.(yield 79%, MS:[M+H]+=757)
Embodiment 45：The synthesis of compound 45
Use intermediate A 12 and 5- phenyl -5,12- dihydros indeno [3,2-a] carbazoles (5-phenyl-5,12- Dihydroindolo [3,2-a] carbazole) intermediate A 5 and diphenylamines are replaced, in addition, by with manufacturing compound 1 The identical method of method manufactured compound 45.(yield 77%, MS:[M+H]+=806)
Embodiment 46：The synthesis of compound 46
Intermediate A 5 is replaced using intermediate A 13, in addition, passes through the identical method of the method with manufacturing compound 1 Compound 46 is manufactured.(yield 70%, MS:[M+H]+=643)
Embodiment 47：The synthesis of compound 47
Use intermediate A 13 and N- ([1,1'- xenyls] -4- bases) -9,9- dimethyl -9H- fluorenes -2- amine (N- ([1,1'- Biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine) replace intermediate A 5 and diphenylamines, except this with Outside, compound 47 has been manufactured by the identical method of the method with manufacturing compound 1.(yield 73%, MS:[M+H]+=835)
Embodiment 48：The synthesis of compound 48
Intermediate A 5 and diphenylamines are replaced using intermediate A 13 and 9H- carbazoles, in addition, by with manufacturing compound 1 The identical method of method manufactured compound 48.(yield 75%, MS:[M+H]+=641)
Embodiment 49：The synthesis of compound 49
Use intermediate A 13 and 12,12- dimethyl -11,12- dihydros indeno [2,1-a] carbazoles (12,12-dimethyl- 11,12-dihydroindeno [2,1-a] carbazole) replace intermediate A 5 and diphenylamines, in addition, by with manufacture The method that the method for compound 1 is identical has manufactured compound 49.(yield 77%, MS:[M+H]+=757)
Embodiment 50：The synthesis of compound 50
Use intermediate A 13 and 5- phenyl -5,7- indoline simultaneously [2,3-b] carbazole (5-phenyl-5,7- Dihydroindolo [2,3-b] carbazole) intermediate A 5 and diphenylamines are replaced, in addition, by with manufacturing compound 1 The identical method of method manufactured compound 50.(yield 75%, MS:[M+H]+=806)
Embodiment 51：The synthesis of compound 51
Use intermediate A 14 and two ([1,1'- xenyls] -4- bases) amine (di ([1,1'-biphenyl] -4-yl) Amine intermediate A 5 and diphenylamines) are replaced, in addition, change has been manufactured by the identical method of the method with manufacturing compound 1 Compound 51.(yield 70%, MS:[M+H]+=718)
Embodiment 52：The synthesis of compound 52
Intermediate A 5 and diphenylamines are replaced using intermediate A 14 and 9H- carbazoles, in addition, by with manufacturing compound 1 The identical method of method manufactured compound 52.(yield 73%, MS:[M+H]+=564)
Embodiment 53：The synthesis of compound 53
Intermediate A 5 and hexichol are replaced using intermediate A 14 and 7H- benzos [c] carbazole (7H-benzo [c] carbazole) Amine, in addition, compound 53 has been manufactured by the identical method of the method with manufacturing compound 1.(yield 72%, MS:[M+ H]+=614)
Embodiment 54：The synthesis of compound 54
Use intermediate A 14 and 7,7- dimethyl -5,7- dihydros indeno [2,1-b] carbazoles (7,7-dimethyl-5,7- Dihydroindeno [2,1-b] carbazole) intermediate A 5 and diphenylamines are replaced, in addition, by with manufacturing compound 1 The identical method of method manufactured compound 54.(yield 76%, MS:[M+H]+=680)
Embodiment 55：The synthesis of compound 55
Use intermediate A 14 and 5- phenyl -5,12- indoline simultaneously [3,2-a] carbazole (5-phenyl-5,12- Dihydroindolo [3,2-a] carbazole) intermediate A 5 and diphenylamines are replaced, in addition, by with manufacturing compound 1 The identical method of method manufactured compound 55.(yield 79%, MS:[M+H]+=729)
Embodiment 56：The synthesis of compound 56
Use intermediate A 15 and N- ([1,1'- xenyls] -4- bases) -9,9- dimethyl -9H- fluorenes -2- amine (N- ([1,1'- Biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine) replace intermediate A 5 and diphenylamines, except this with Outside, compound 56 has been manufactured by the identical method of the method with manufacturing compound 1.(yield 73%, MS:[M+H]+=758)
Embodiment 57：The synthesis of compound 57
Intermediate A 5 and diphenylamines are replaced using intermediate A 15 and 9H- carbazoles, in addition, by with manufacturing compound 1 The identical method of method manufactured compound 57.(yield 74%, MS:[M+H]+=564)
Embodiment 58：The synthesis of compound 58
Use intermediate A 15 and 12,12- dimethyl -11,12- dihydros indeno [2,1-a] carbazoles (12,12-dimethyl- 11,12-dihydroindeno [2,1-a] carbazole) replace intermediate A 5 and diphenylamines, in addition, by with manufacture The method that the method for compound 1 is identical has manufactured compound 58.(yield 72%, MS:[M+H]+=680)
Embodiment 59：The synthesis of compound 59
Use intermediate A 15 and 5- phenyl -5,12- indoline simultaneously [3,2-a] carbazole (5-phenyl-5,12- Dihydroindolo [3,2-a] carbazole) intermediate A 5 and diphenylamines are replaced, in addition, by with manufacturing compound 1 The identical method of method manufactured compound 59.(yield 72%, MS:[M+H]+=729)
Experimental example 1
Will be withThickness thin film be coated with the glass substrate of ITO (tin indium oxide, indium tin oxide) and put Enter in the distilled water dissolved with detergent, washed using ultrasonic wave.At this time, as detergent, Fei Xier companies are used (Fischer Co.) product, as distilled water, has used the filtering manufactured by using Millipore Corp. (Millipore Co.) Device (Filter) filter 2 times after distilled water.After ITO is washed 30 minutes, using distilled water repeatedly 2 times and carry out 10 minutes it is super Sonic washing.After distilling water washing, ultrasonic washing is carried out using isopropanol, acetone, methanol solvate, is transferred to after dry In plasma washing machine.In addition, being cleaned aforesaid substrate after five minutes using oxygen plasma, base plate transfer to vacuum is steamed In plating machine.
On the ito transparent electrode so prepared withThickness thermal vacuum following six nitriles, six azepine benzo is deposited Phenanthrene (hexanitrile hexaazatriphenylene；HAT) compound and form hole injection layer.Injected in above-mentioned hole Layer onThickness thermal vacuum evaporation HT1 compounds, and withThickness vacuum evaporation HT2 compounds successively And form hole transmission layer.Then, on above-mentioned hole transmission layer, using the compound 1 of embodiment 1 and compound H2 as master Body, as the weight ratio described in table 1, is deposited and is formed altogether with phosphorescent dopants DpThe luminescent layer of thickness.In above-mentioned hair On photosphere withThickness vacuum evaporation ET1 materials and form hole blocking layer.With 1 on above-mentioned hole blocking layer:1 Weight ratio vacuum evaporation ET2 materials and LiQ (quinoline lithium, Lithium Quinolate) and formedElectron transfer layer. It is deposited successively on above-mentioned electron transfer layerThe lithium fluoride (LiF) of thickness, on it withThickness AM aluminum metallization and Form cathode.
In the above process, the evaporation rate of organic matter maintains/ sec, the lithium fluoride of cathode maintain/ The evaporation rate of sec, aluminium maintainThe evaporation rate of/sec, vacuum maintains 1 × 10 during evaporation-7~5 × 10-8torr。
Electric current, measure voltage, efficiency and service life are applied to the organic illuminating element of manufacture, and the results are shown in following tables In 1.
Experimental example 2 to 16
When forming luminescent layer, as phosphorescent dopants, above-mentioned implementation is replaced using the compound described in table 1 below respectively The compound 1 of example 1, in addition, is implemented by the method identical with above-mentioned experimental example 1, thus made respectively experimental example 2 to 16 organic illuminating element.When at this moment, using the mixture of 2 kinds of compounds as main body, bracket is represented between host compound Weight ratio, H2 materials are same as described above.
For the organic illuminating element of manufacture, electric current, measure voltage, efficiency are applied by the method identical with experimental example 1 And the service life, and the results are shown in table 1 below.
Comparative experiments example 1 to 5
Listed in Table 1 content replaces the compound 1 of above-described embodiment 1 using the compound described in table 1 below, In addition, implemented by the method identical with above-mentioned experimental example 1 to have made organic illuminating element.C1 to C3 in table 1 below Following compounds is represented respectively.When at this moment, using the mixture of 2 kinds of compounds as main body, bracket represents host compound Between weight ratio.
Electric current, measure voltage, efficiency and longevity are applied by the method identical with experimental example 1 to the organic illuminating element of manufacture Life, and recorded a demerit and be shown in table 1 below.
【Table 1】
In above-mentioned table 1, T95 represents that brightness reaches the time required during the 95% of original intensity.
As shown in Table 1 above, compared with the compound C1 as green emitting main substance in the past, it can confirm that this hair Bright involved compound is the main substance with more excellent high efficiency and long-life characteristics.In addition, with compound C2 phases Than when, show more than about 2 times of life characteristic of increase, when compared with compound C3, show low-voltage and long-life characteristics. It is possible thereby to confirm, the position of substitution of the dibenzofurans of compound according to the embodiment and voltage and service life have differences.
In addition, compared with comparative example 3 or 4, it has been confirmed that the triazine as miscellaneous substituent, positioned at the 1 of dibenzofurans During number position when positioned at No. 2 positions compared with, show in efficiency and in terms of the service life advantage.Moreover, by comparative example 5 with the present invention Compound when comparing, according to the position of substituent, show very big voltage differences, this can receive the neighbour from element The hole of layer and the aspect of the stability of electronics and balance are connect, substituent is located at No. 1 and No. 6 positions of dibenzofurans in structure When positioned at No. 4 and No. 6 positions compared with, show the advantage of element.
Through the above, the optimization experiment example of the present invention is illustrated, but the present invention is not limited to this, weighed It can implement various deformations in the range of sharp claimed range and detailed description of the invention, this falls within the category of invention.

Claims (13)

  1. A kind of 1. compound represented by following chemical formula 1:
    Chemical formula 1
    In above-mentioned chemical formula 1,
    X1For O or S,
    Y1To Y3It is each independently N or CR3, Y1To Y3In it is at least one be N,
    L1And L2It is each independently key, substituted or unsubstituted C6-60Arlydene or it is substituted or unsubstituted include one with On heteroatomic C in O, N, Si and S2-60Heteroarylidene,
    Ar1And Ar2It is each independently substituted or unsubstituted C6-60Aryl or substituted or unsubstituted include 1 to 3 Heteroatomic C in N, O and S2-60Heteroaryl,
    Ar3For N (Ar11)(Ar12) or substituted or unsubstituted include 1 to the 3 heteroatomic C in N, O and S2-60 Heteroaryl, with the L2With reference to atom be hetero atom,
    Wherein, Ar11And Ar12It is each independently substituted or unsubstituted C6-60Aryl or substituted or unsubstituted include 1 To 3 heteroatomic C in N, O and S2-60Heteroaryl,
    R1To R3It is each independently hydrogen, deuterium, halogen, cyano group, amino, substituted or unsubstituted C1-60Alkyl, C1-60Haloalkyl, Substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C1-60Halogenated alkoxy, substituted or unsubstituted C3-60Cycloalkanes Base, substituted or unsubstituted C2-60Alkenyl, substituted or unsubstituted C6-60Aryl, substituted or unsubstituted C6-60Aryloxy group or It is substituted or unsubstituted comprising moreing than one the heteroatomic C in N, O and S2-60Heterocyclic radical,
    A1 and a2 is each independently 0 to 3 integer.
  2. 2. compound according to claim 1, wherein,
    Y1And Y2For N, Y3For CH；
    Y1And Y3For N, Y2For CH；Or
    Y1、Y2And Y3For N.
  3. 3. compound according to claim 1, wherein, L1And L2It is each independently key or in following radicals It is any:
  4. 4. compound according to claim 1, wherein, Ar1And Ar2It is each independently any in following radicals Kind:
    In above-mentioned group,
    Z1And Z2It is each independently hydrogen, deuterium, halogen, cyano group, amino, C1-20Alkyl, C1-20Haloalkyl or C6-20Aryl,
    C1 and c2 is each independently 0 to 3 integer.
  5. 5. compound according to claim 4, wherein, Ar1And Ar2It is each independently any in following radicals Kind:
  6. 6. compound according to claim 1, wherein, Ar3For selected from any of following radicals:
    In above-mentioned group,
    X2And X3It is each independently O, S, NZ13Or CZ14Z15,
    Ar11And Ar12It is each independently substituted or unsubstituted C6-20Aryl or substituted or unsubstituted include 1 to 3 Heteroatomic C in N, O and S2-20Heteroaryl,
    Z11To Z15It is each independently hydrogen, deuterium, halogen, cyano group, amino, C1-20Alkyl, C1-20Haloalkyl or C6-20Aryl,
    N1 and n2 is each independently 0 to 3 integer.
  7. 7. compound according to claim 6, wherein, Ar3For selected from any of following radicals:
  8. 8. compound according to claim 1, wherein, R1To R3For hydrogen.
  9. 9. compound according to claim 1, wherein, the compound is selected from any of following compounds:
  10. 10. a kind of organic illuminating element comprising：First electrode, it is opposed with the first electrode and possess second electricity Pole and possess more than 1 layer of organic matter layer between the first electrode and the second electrode,
    Compound described in any one of 1 layer of claim 1 to 9 contained above in the organic matter layer.
  11. 11. organic illuminating element according to claim 10 is comprising the organic matter layer of the compound is noted for hole Enter layer, hole transmission layer or the layer for being carried out at the same time hole injection and hole transport.
  12. 12. organic illuminating element according to claim 10 is comprising the organic matter layer of the compound is noted for electronics Enter layer, electron transfer layer or the layer for being carried out at the same time electron injection and electric transmission.
  13. 13. organic illuminating element according to claim 10 is comprising the organic matter layer of the compound is luminous Layer.
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