CN109311922A - Iridium complex and the organic illuminating element for utilizing it - Google Patents
Iridium complex and the organic illuminating element for utilizing it Download PDFInfo
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- CN109311922A CN109311922A CN201880002136.2A CN201880002136A CN109311922A CN 109311922 A CN109311922 A CN 109311922A CN 201880002136 A CN201880002136 A CN 201880002136A CN 109311922 A CN109311922 A CN 109311922A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0033—Iridium compounds
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
Abstract
The present invention provides a kind of iridium complex and the organic illuminating element using it.
Description
Technical field
Cross reference to related applications
This application claims be somebody's turn to do based on South Korea patent application the 10-2017-0001324th priority on January 4th, 2017
Full content as part of this specification disclosed in the document of South Korea patent application and include.
The present invention relates to iridium complex and utilize its organic illuminating element.
Background technique
Under normal conditions, organic light emission phenomenon refers to the phenomenon that converting electrical energy into 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, to largely be studied.
Organic illuminating element usually has the organic matter layer comprising anode and cathode and between anode and cathode
Structure.In order to improve the efficiency and stability of organic illuminating element, above-mentioned organic matter layer is formed by multilayered structure in most cases,
And above-mentioned multilayered structure is made of different substance, for example, can be by hole injection layer, hole transmission layer, luminescent layer, electricity
The formation such as sub- transport layer, electron injecting layer.For the structure of such organic electroluminescent device, if two electrodes it
Between apply voltage, then hole is injected into organic matter layer from anode, and electronics is injected into organic matter layer from cathode, when institute's injected holes
It will form exciton (exciton) when meeting with electronics, and light will be issued when the exciton transits to ground state again.
It is lasting to require exploitation new material for the organic matter for organic illuminating element as described above.
[existing technical literature]
[patent document]
(patent document 0001) Korean Patent Publication No. the 10-2000-0051826th
Summary of the invention
The present invention relates to a kind of iridium complex and utilize its organic illuminating element.
The present invention provides the compound indicated by following chemical formula 1 or following chemical formula 2:
[chemical formula 1]
[chemical formula 2]
In above-mentioned chemical formula 1 and 2,
X is O or S,
R1For C that is unsubstituted or being replaced by deuterium1-60Alkyl, the silicyl of carbon atom number 1 to 60 or substitution do not take
The C in generation6-60Aryl,
R2And R3It is each independently hydrogen or C that is unsubstituted or being replaced by deuterium1-60Alkyl,
N is 1 or 2.
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 has and has one layer or more of organic matter between above-mentioned first electrode and above-mentioned second electrode
Layer, above-mentioned organic matter layer include luminescent layer, and above-mentioned luminescent layer includes above compound.
The above-mentioned compound indicated by chemical formula 1 or 2 can be used as the organic matter layer of organic illuminating element and use, especially
Its material that can be used as luminescent layer and use, so as to realized in organic illuminating element efficiency to propose high and low driving electric
The raising of pressure and/or life characteristic.
Detailed description of the invention
Fig. 1 illustrates the examples for the organic illuminating element being made of substrate 1, anode 2, luminescent layer 3, cathode 4.
Fig. 2 illustrate by substrate 1, anode 2, hole injection layer 5, hole transmission layer 6, luminescent layer 7, electron transfer layer 8 with
And the example of the organic illuminating element of the composition of cathode 4.
Specific embodiment
In the following, being illustrated in more details to help to understand the present invention.
In this specification,Indicate the key connecting with other substituent groups.
In this specification, " substituted or unsubstituted " this term refers to by selected from deuterium, halogen group, itrile 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), first silicon
It is alkyl, boryl, alkyl, naphthenic base, alkenyl, aryl, aralkyl, arylalkenyl, alkylaryl, alkyl amine group, aralkyl amido, miscellaneous
Arylamine group, arylamine group, aryl phosphino- take comprising more than one in the more than one heterocycle in N, O and S atom
It is substituted or unsubstituted for base, or taken by the substituent group that 2 or more substituent groups in foregoing illustrative substituent group are formed by connecting
In generation, is unsubstituted.For example, " substituent group that 2 or more substituent groups are formed by connecting " can be xenyl.That is, xenyl can be
Aryl can also be construed to the substituent group that 2 phenyl are formed by connecting.
In this specification, the carbon atom number of carbonyl is not particularly limited, but preferably carbon atom number is 1 to 40.Specifically,
It can be the compound of following structures, but not limited to this.
In this specification, in ester group, the oxygen atom of ester group can be by the straight chain of carbon atom number 1 to 25, branch or cyclic annular alkane
Base or the aryl of carbon atom number 6 to 25 replace.Specifically, can be the compound of following structural formula, but not limited to this.
In this specification, the carbon atom number of imide is not particularly limited, but preferably carbon atom number is 1 to 25.Specifically
For, it can be the compound of following structures, but not limited to this.
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 not limited to this.
In this specification, boryl specifically has trimethyl boryl, triethyl group boryl, fert-butyidimethylsilyl boryl, triphenyl borine
Base, phenyl boryl etc., but not limited to this.
In this specification, as the example of halogen group, there are fluorine, chlorine, bromine or iodine.
In this specification, abovementioned alkyl can be linear chain or branched chain, and carbon atom number is not particularly limited, but preferably 1 to
40.According to an embodiment, the carbon atom 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 atom number of abovementioned alkyl is 1 to 6.As the specific example of alkyl, there is first
Base, ethyl, propyl, n-propyl, isopropyl, butyl, normal-butyl, isobutyl group, tert-butyl, sec-butyl, 1- methyl-butvl, 1- second
Base-butyl, amyl, n-pentyl, isopentyl, neopentyl, tertiary pentyl, hexyl, n-hexyl, 1- methyl amyl, 2- methyl amyl, 4-
Methyl -2- amyl, 3,3- dimethylbutyl, 2- ethyl-butyl, heptyl, n-heptyl, 1- methylhexyl, cyclopentyl-methyl, hexamethylene
Ylmethyl, octyl, n-octyl, t-octyl, 1- methylheptyl, 2- ethylhexyl, 2- propylpentyl, n-nonyl, 2,2- dimethyl
Heptyl, 1- Ethyl-propyl, 1,1- Dimethyl-propyl, isohesyl, 2- methyl amyl, 4- methylhexyl, 5- methylhexyl etc., but
It's not limited to that.
In this specification, above-mentioned alkenyl can be linear chain or branched chain, and carbon atom number is not particularly limited, but preferably 2 to
40.According to an embodiment, the carbon atom 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 atom number of above-mentioned alkenyl is 2 to 6.As concrete example, there are vinyl, 1- third
Alkenyl, isopropenyl, 1- cyclobutenyl, 2- cyclobutenyl, 3- cyclobutenyl, 1- pentenyl, 2- pentenyl, 3- pentenyl, 3- methyl-1-
Cyclobutenyl, 1,3- butadiene, allyl, 1- phenylethylene -1- base, 2- phenylethylene -1- base, 2,2- diphenylethlene -1- base,
2- phenyl -2- (naphthalene -1- base) ethylene -1- base, 2,2- bis- (diphenyl -1- base) ethylene -1- base, Stilbene base, styryls etc., but simultaneously
It is not limited to this.
In this specification, naphthenic base is not particularly limited, but the naphthenic base of preferably carbon atom number 3 to 60, real according to one
Mode is applied, the carbon atom number of above-mentioned naphthenic base is 3 to 30.According to another embodiment, the carbon atom number of above-mentioned naphthenic base be 3 to
20.According to another embodiment, the carbon atom number of above-mentioned naphthenic base is 3 to 6.Specifically, having cyclopropyl, cyclobutyl, ring penta
Base, 3- methylcyclopentyl, 2,3- dimethylcyclopentyl, cyclohexyl, 3- methylcyclohexyl, 4- methylcyclohexyl, 2,3- dimethyl
Cyclohexyl, 3,4,5- trimethylcyclohexyls, 4- tert-butylcyclohexyl, suberyl, cyclooctyl etc., but not limited to this.
In this specification, aryl is not particularly limited, but the aryl of preferably carbon atom number 6 to 60, can be monocycle virtue
Base or polyaromatic.According to an embodiment, the carbon atom number of above-mentioned aryl is 6 to 30.According to an embodiment, above-mentioned aryl
Carbon atom number be 6 to 20.It can be phenyl, xenyl, terphenyl etc. as monocyclic aryl, but simultaneously about above-mentioned aryl
It is not limited to this.As above-mentioned polyaromatic, can for naphthalene, anthryl, phenanthryl, pyrenyl, base,Base, fluorenyl etc., but simultaneously
It is not limited to this.
In this specification, fluorenyl can be substituted, and 2 substituent groups can be bonded to each other and form spiro structure.In above-mentioned fluorenes
In the substituted situation of base, Ke Yiwei Deng but not limited to this.
In this specification, heterocycle is comprising more than one in O, N, Si and S as heteroatomic heterocycle, carbon atom
Number is not particularly limited, but preferably carbon atom number is 2 to 60.As the example of heterocycle, have thienyl, furyl, pyrrole radicals,
Imidazole radicals, thiazolyl,Oxazolyl,Di azoly, triazolyl, pyridyl group, bipyridyl, pyrimidine radicals, triazine radical, acridinyl,
Pyridazinyl, pyrazinyl, quinolyl, quinazolyl, quinoxalinyl, phthalazinyl, Pyridopyrimidine base, pyrido-pyrazine base, pyrazine
And pyrazinyl, isoquinolyl, indyl, carbazyl, benzoOxazolyl, benzimidazolyl, benzothiazolyl, benzo carbazole base,
It is benzothienyl, dibenzothiophene, benzofuranyl, phenanthroline (phenanthrol ine), differentOxazolyl, thiadiazoles
Base, phenothiazinyl and dibenzofuran group etc., but not limited to this.
In this specification, the example phase of aralkyl, arylalkenyl, alkylaryl, aryl and above-mentioned aryl in arylamine group
Together.In this specification, aralkyl, alkylaryl, the alkyl in alkyl amine group are identical as the illustration of abovementioned alkyl.This specification
In, the heteroaryl in heteroaryl amine can apply with respect to the explanation of above-mentioned heterocycle.Alkenyl in this specification, in arylalkenyl
It is identical as the illustration of above-mentioned alkenyl.In this specification, arlydene is that divalent group can be applicable in above-mentioned about aryl in addition to this
Explanation.In this specification, heteroarylidene is that divalent group can be applicable in the above-mentioned explanation about heterocycle in addition to this.This
In specification, hydrocarbon ring not instead of 1 valence group, 2 substituent groups are combined into, and in addition to this, can be applicable in above-mentioned about aryl
Or the explanation of naphthenic base.In this specification, heterocycle not instead of 1 valence group, 2 substituent groups are combined into, in addition to this, can be with
It is applicable in the above-mentioned explanation about heterocycle.
In above-mentioned chemical formula 1 or 2, it is preferable that R1For C that is unsubstituted or being replaced by deuterium1-5Alkyl, carbon atom number 3 to 10
Silicyl or substituted or unsubstituted C6-10Aryl.It is highly preferred that R1For methyl, ethyl, propyl, isopropyl, butyl, different
Butyl, tert-butyl, amyl, isopentyl, tertiary pentyl, neopentyl, sec-amyl, 3- amyl, CD3、Si(CH3)3Or phenyl.
Preferably, R2And R3It is each independently hydrogen or C that is unsubstituted or being replaced by deuterium1-5Alkyl.More preferably, R2
And R3It is each independently hydrogen, methyl or CD3。
Typical example by the compound of above-mentioned chemical formula 1 or 2 expression is as follows:
In addition, the present invention provides the change indicated by the above-mentioned chemical formula 1 or 2 of such as following reaction equations 1 as an example
The manufacturing method for closing object (the case where n is 2), is readily applicable to the case where n is 1:
[reaction equation 1]
Above-mentioned manufacturing method can embody in the later-described embodiments.
In addition, the present invention provides the organic illuminating element of the compound comprising being indicated by above-mentioned chemical formula 1 or 2.As one
A example, the present invention a kind of organic illuminating element is provided comprising: it is first electrode, opposed with above-mentioned first electrode and have
Second electrode and have one layer or more of organic matter layer between above-mentioned first electrode and above-mentioned second electrode, it is above-mentioned
Organic matter layer includes luminescent layer, and above-mentioned luminescent layer includes the compound indicated by above-mentioned chemical formula 1 or 2.
The organic matter layer of organic illuminating element of the invention can be formed by single layer structure, can also by be laminated with two layers with
On the multilayered structure of organic matter layer formed.For example, organic illuminating element of the invention can have comprising 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, may include less organic layer.
In addition, organic illuminating element according to the present invention can be to be sequentially laminated with anode, one layer or more on substrate
The organic illuminating element of the structure (standard type, normal type) of organic matter layer and cathode.In addition, according to the present invention have
Machine light-emitting component can be to be sequentially laminated with the organic matter layer of cathode, one layer or more and the reverse structure of anode on substrate
The organic illuminating element of (inversion type, inverted type).For example, the organic illuminating element of an embodiment according to the present invention
Structure be illustrated in Fig. 1 and Fig. 2.
Fig. 1 illustrates the examples of the organic illuminating element formed by substrate 1, anode 2, luminescent layer 3, cathode 4.In this knot
In structure, it may be embodied in above-mentioned luminescent layer by the compound that above-mentioned chemical formula 1 or 2 indicates.
Fig. 2 illustrate by substrate 1, anode 2, hole injection layer 5, hole transmission layer 6, luminescent layer 7, electron transfer layer 8 with
And the example of the organic illuminating element of the formation of cathode 4.It in this configuration, can be with by the compound that above-mentioned chemical formula 1 or 2 indicates
Included in luminescent layer.
Organic illuminating element according to the present invention includes in addition to this can by the compound that above-mentioned chemical formula 1 or 2 indicates
To be manufactured by material well-known in the art and method.In addition, including multiple organic matters in above-mentioned organic illuminating element
In the case where layer, above-mentioned organic matter layer can be formed by identical substance or different substances.
For example, organic illuminating element according to the present invention can be by stacking gradually first electrode, organic matter on substrate
Layer and second electrode and manufacture.At this moment, it can manufacture as follows: utilize sputtering (sputtering) or electron beam evaporation method (e-
Beam evaporation) etc PVD (physical Vapor Deposition: physical vapor deposition method) method, in substrate
Upper evaporation metal or conductive metal oxide or their alloy and form anode, then on the anode formed packet
Organic matter layer containing hole injection layer, hole transmission layer, luminescent layer and electron transfer layer, vapor deposition can be used as the object of cathode later
Matter and manufacture.Other than this method, can also on substrate successively evaporation cathode substance, organic matter layer, anode material and
Manufacture organic illuminating element.
In addition, the compound indicated by above-mentioned chemical formula 1 or 2 when manufacturing organic illuminating element, not only can use very
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 not limited to this.
Other than this method, can also on substrate successively evaporation cathode substance, organic matter layer, anode material and make
Make organic illuminating element (WO 2003/012890).But it's not limited to that for manufacturing 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.
As above-mentioned anode material, generally for enabling hole successfully to inject to organic matter layer, preferably work function
Big substance.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- dioxy) thiophene] (PEDOT), polypyrrole and polyaniline etc. are led
Electrical macromolecule etc., but not limited to this.
As above-mentioned cathode substance, generally for electronics is injected easily to organic matter layer, preferably work function is small
Substance.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 LiO2Multilayered structures substance such as/Al etc., but not limited to this.
Above-mentioned hole injection layer is the layer in the hole that injection carrys out self-electrode, as hole injecting material, preferably followingization
It closes object: having the ability of transporting holes, there is hole injection effect from anode, for the excellent of luminescent layer or luminescent material
Hole inject effect, prevent in luminescent layer generated exciton to migrate 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
It is organic matter, anthraquinone and polyaniline and polythiophene that machine object, quinacridone (quinacridone), which are organic matter, (perylene),
It is electroconductive polymer etc., but not limited 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 substance that can be received the hole from anode or hole injection layer and transfer them to luminescent layer, right
The big substance of the mobility in hole is suitable.As concrete example, there are aryl amine system organic matter, electroconductive polymer, Yi Jitong
When there are conjugate moiety and the block copolymer of non-conjugated portion etc., but not limited to this.
Above-mentioned luminescent layer is can to receive respectively hole and electronics from hole transmission layer and electron transfer layer and tie them
Close and issue the layer of the light of visible light region.Above-mentioned luminescent layer may include material of main part and dopant material, mix as above-mentioned
Miscellaneous agent material can be used by the compound of the above-mentioned expression of chemical formula 1 or 2.
Aforementioned body material has aromatic fused ring derivative or nitrogen-containing heterocgcies etc..Specifically, thick as aromatic series
Ring derivatives have anthracene derivant, pyrene derivatives, naphthalene derivatives, pentacene derivative, phenanthrene compound, fluoranthene compound etc., as
Nitrogen-containing heterocgcies have carbazole derivates, dibenzofuran derivative, ladder type furan compoundPyrimidine derivatives etc., but not limited to this.
Above-mentioned electron transfer layer is from electron injecting layer reception electronics and by the layer of electron-transport to luminescent layer, as electronics
Transport materials are can to receive well electronics from cathode and transfer them to the substance of luminescent layer, big to the mobility of electronics
Substance be suitable.As concrete example, there is the Al complex of 8-hydroxyquinoline, comprising Alq3Complex, organic free radical
Compound, hydroxyl brass-metal complex etc., but not limited to this.Electron transfer layer can be as used in the prior art
As be used together with the cathode substance of any desired.In particular, the example of suitable cathode substance is with low work function
And with aluminium layer or the common substance of silver layer.Specially caesium, barium, calcium, ytterbium and samarium, for each substance, with aluminium layer or
Silver layer accompanies.
Above-mentioned electron injecting layer is the layer for the electronics that injection carrys out self-electrode, preferably following compound: has transmission electronics
Ability, there is electron injection effect from cathode, for the excellent electron injection effect of luminescent layer or luminescent material, prevent
Only generated 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, bis- (8-hydroxyquinoline) zinc, bis- (8-hydroxyquinoline) copper,
It is bis- (8-hydroxyquinoline) manganese, three (8-hydroxyquinoline) aluminium, three (2- methyl -8-hydroxyquinoline) aluminium, three (8-hydroxyquinoline) galliums, double
(10- hydroxy benzo [h] quinoline) beryllium, bis- (10- hydroxy benzo [h] quinoline) zinc, bis- (2- methyl -8- quinoline) gallium chlorides, bis- (2-
Methyl -8- quinoline) (o-cresol) gallium, bis- (2- methyl -8- quinoline) (1- naphthols) aluminium, bis- (2- methyl -8- quinoline) (beta naphthals)
Gallium etc., but not limited to this.
Organic illuminating element according to the present invention can be top emission type, bottom emission type according to used material
Or bidirectional luminescence type.
In addition, the compound indicated by above-mentioned chemical formula 1 or 2 has been further included in other than organic illuminating element
In machine solar battery or organic transistor.
To the compound that is indicated by above-mentioned chemical formula 1 or 2 and include its organic illuminating element in the examples below
Manufacture is concretely demonstrated.But following embodiments are for illustrating the present invention, it's not limited to that for the scope of the present invention.
[Production Example]
Production Example 1: the manufacture of intermediate 1
1) manufacture of intermediate 1-1
In three-neck flask, by 4- iodine dibenzo [b, d] furans (30.0g, 102.0mmol), potassium phosphate (65.0g,
It 306.0mmol) is dissolved into toluene (600ml) and water (60ml).20 minutes nitrogen purgings are carried out to reactant, are added 2,4,6-
Trimethyl -1,3,5,2,4,6- trioxa, three borine (14.1g, 112.2mmol), Pd2(dba)3(0.9g, 1.0mmol) and S-
Phos (1.7g, 4.1mmol), at argon atmospher stirred at reflux condition 18 hours.It is cooled to room temperature, is then added after reaction
Water (200ml), moves on to separatory funnel and has extracted organic layer.Use MgSO4After dry extract liquor, filters and be concentrated, then use silica gel
Column chromatography, which is purified sample, has obtained intermediate 1-1.(18.0g, yield 91%, MS:[M+H]+=182).
2) manufacture of intermediate 1-2
In three-neck flask, intermediate 1-1 (15.0g, 82.3mmol), sodium carbonate (9.2g, 86.4mmol) are dissolved in
In n-hexane (150ml), bromine (4.4ml, 86.4mmol) is added dropwise thereto, at stirring at normal temperature 72 hours.At the end of reaction, it is added dropwise
After sodium thiosulfate solution, reaction solution is moved into separatory funnel and extracts organic layer.Use MgSO4After dry extract liquor, filtering
And be concentrated, then sample is purified with silica gel column chromatography and has obtained intermediate 1-2 (15.5g, yield 72%, MS:[M+
H]+=261).
3) manufacture of intermediate 1-3
In three-neck flask be added intermediate 1-2 (15.0g, 57.4mmol), bis- (pinacol conjunctions) two boron (17.5g,
68.9mmol)、Pd(dba)2(0.7g, 1.1mmol), tricyclohexyl phosphine (0.6g, 2.3mmol), KOAc (11.3g,
114.9mmol) and 1,4- bis-Alkane (225ml), at argon atmospher stirred at reflux condition 12 hours.It is cooled to after reaction
Then reaction solution is moved to separatory funnel by room temperature, be added water (200mL), be extracted with ethyl acetate.Use MgSO4Dry extract liquor
Afterwards, filter and be concentrated, then sample is purified with silica gel column chromatography obtained intermediate 1-3 (20.5g, yield 78%,
MS:[M+H]+=384).
4) manufacture of intermediate 1
In three-neck flask, intermediate 1-3 (14.0g, 45.4mmol), 2- bromopyridine (7.9g.50.0mmol) are dissolved
In THF (210ml), by K2CO3(25.1g, 181.7mmol) is dissolved in water (105ml).Pd (PPh is added thereto3)4
(2.1g.1.8mmol), at argon atmospher stirred at reflux condition 8 hours.It is cooled to room temperature after reaction, then by reaction solution
Separatory funnel is moved to, is extracted with water and ethyl acetate.Use MgSO4It after dry extract liquor, filters and is concentrated, then use silicagel column color
Spectrum sample is purified obtained intermediate 1 (8.6g, yield 73%, MS:[M+H]+=259).
Production Example 2: the manufacture of intermediate 2
In double-neck flask, intermediate 1 (8.0g, 30.9mmol), sodium ethoxide (4.2g.61.7m mol) and ethyl alcohol-is added
D6 (130ml) is stirred 72 hours under reflux conditions.It is cooled to room temperature after reaction, after concentrate solution, water and acetic acid is added
Ethyl ester moves to separatory funnel, extracts organic layer.With M gSO4After dry extract liquor, filters and be concentrated, then use silica gel column chromatography
Sample is purified obtained intermediate 2 (6.1g, yield 75%, MS:[M+H]+=262).
Production Example 3: the manufacture of intermediate 3
1) manufacture of intermediate 3-1
In three-neck flask, by 1- iodine dibenzo [b, d] furans -2- alcohol (20.0g, 64.5mmol), phenylboric acid
(8.7g, 70.9mmol) is dissolved in THF (300ml), by K2CO3(35.7g, 258.0mol) is dissolved in water (150ml).Xiang Qi
Middle addition Pd (PPh3)4(3.0g, 2.6mmol), at argon atmospher stirred at reflux condition 8 hours.It is cooled to after reaction often
Then reaction solution is moved to separatory funnel by temperature, extracted with water and ethyl acetate.Use MgSO4After dry extract liquor, filter and dense
Contracting, then sample is purified with silica gel column chromatography obtained intermediate 3-1 (12.9g, yield 77%, MS:[M+H]+=
260)。
2) manufacture of intermediate 3-2
In three-neck flask, after intermediate 3-1 (12.0g, 46.1mmol) is dissolved in acetonitrile (340ml), three second are added
Amine (20ml, 73.8mmol), perfluor -1- butane sulfuryl fluoride (12ml, 69.2mmol), are stirred overnight at normal temperature.Reaction terminates
Afterwards, it is diluted with ethyl acetate, moves to separatory funnel, after the washing of 0.5M sodium bisulphate solution, extract organic layer.With
MgSO4After dry extract liquor, filters and be concentrated, then sample is purified with silica gel column chromatography and has obtained intermediate 3-2
(18.8g, yield 75%, MS:[M+H]+=542).
3) manufacture of intermediate 3
In three-neck flask, by intermediate 3-2 (18.0g, 33.2mmol), pyridine -2- ylboronic acid (4.5g, 36.5mmol)
It is dissolved in THF (270ml), by K2CO3(18.3g, 132.8mmol) is dissolved in water (135ml).Pd (PPh is added thereto3)4
(1.5g, 1.3mmol), at argon atmospher stirred at reflux condition 8 hours.It is cooled to room temperature after reaction, then by reaction solution
Separatory funnel is moved to, is extracted with water and ethyl acetate.Use MgSO4It after dry extract liquor, filters and is concentrated, then use silicagel column color
Spectrum sample is purified obtained intermediate 3-3 (8.3g, yield 78%.MS:[M+H]+=321).
Production Example 4: the manufacture of intermediate 4
1) manufacture of intermediate 4-1
In three-neck flask, by the iodo- 3- methylbenzene (25.0g, 105.9mmol) of the fluoro- 2- of 1-, (2- hydroxy phenyl) boric acid
(16.1g, 116.5mmol) is dissolved in THF (375ml), by K2CO3(58.6g, 423.7m mol) is dissolved in water (190ml)
In.Pd (PPh is added thereto3)4(4.9g, 4.2mmol), at argon atmospher stirred at reflux condition 8 hours.It is cold after reaction
But to room temperature, reaction solution is then moved into separatory funnel, is extracted with water and ethyl acetate.Use MgSO4After dry extract liquor, filtering
And be concentrated, then sample is purified with silica gel column chromatography and has obtained intermediate 4-1 (15.2g, yield 71%, MS:[M+
H]+=202).
2) manufacture of intermediate 4-2
In three-neck flask, intermediate 4-1 (15.0g, 74.2mmol), K is added2CO3(20.5g,148.3mmol)、NMP
(200ml) is stirred overnight at 120 DEG C.It is cooled to room temperature after reaction, water is then added dropwise bit by bit into reaction solution
(150ml).Then reaction solution is moved into separatory funnel, extracts organic layer with water and ethyl acetate.Use MgSO4Dry extract liquor,
After filtering and being concentrated, sample is purified with silica gel column chromatography and has obtained intermediate 4-2 (11.6g, yield 86%, MS:[M
+H]+=182).
3) manufacture of intermediate 4-3
In double-neck flask, intermediate 4-2 (10.0g, 54.9mmol), NBS (10.3g, 57.6mmol) and DMF is added
(200ml), under an argon, at stirring at normal temperature 8 hours.After reaction, reaction solution is moved into separatory funnel, with water and acetic acid
Ethyl ester extracts organic layer.Use MgSO4Sample is purified with silica gel column chromatography and is obtained after filtering and being concentrated by dry extract liquor
Arrived intermediate 4-3 (12.2g. yield 85%, MS:[M+H]+=261).
4) manufacture of intermediate 4-4
In three-neck flask be added intermediate 4-3 (12.0g, 46.0mmol), bis- (pinacol conjunctions) two boron (14.0g,
55.1mmol)、Pd(dba)2(0.5g, 0.9mmol), tricyclohexyl phosphine (0.5g, 0.9mmol), KOAc (9.0g, 91.9mmol)
With 1,4- bis-Alkane (180ml), at argon atmospher stirred at reflux condition 12 hours.It is cooled to room temperature, then will after reaction
Reaction solution moves to separatory funnel, is added water (200mL), is extracted with ethyl acetate.Use MgSO4After dry extract liquor, filter and dense
Contracting, then sample is purified with silica gel column chromatography obtained intermediate 4-4 (11.6g. yield 82%, MS:[M+H]+=
308)。
5) manufacture of intermediate 4
In three-neck flask, by the bromo- 5- picoline of intermediate 4-4 (11.0g, 35.7mmol), 2- (6.8g,
It 39.3mmol) is dissolved in THF (165ml), by K2CO3(19.7g, 142.8mmol) is dissolved in water (83ml).Pd is wherein added
(PPh3)4(1.6g, 1.4mmol), at argon atmospher stirred at reflux condition 8 hours.It is cooled to room temperature, then will after reaction
Reaction solution moves to separatory funnel, is extracted with water and ethyl acetate.Use MgSO4After dry extract liquor, filters and be concentrated, then use silicon
Rubber column gel column chromatography sample is purified obtained intermediate 4 (7.0g, yield 72%, MS:[M+H]+=273).
Production Example 5: the manufacture of intermediate 5
In double-neck flask, by intermediate 4 (7.0g, 25.6mmol), sodium ethoxide (7.0g, 102.4mm ol), ethyl alcohol-D6
(220ml) is stirred 72 hours under reflux conditions.It is cooled to room temperature after reaction, after concentrated solvent, water and acetic acid second is added
Ester moves to separatory funnel, has extracted organic layer.With Mg SO4After dry extract liquor, filters and be concentrated, then use silica gel column chromatography
Sample is purified obtained intermediate 5 (4.4g, yield 62%, MS:[M+H]+=279).
Production Example 6: the manufacture of intermediate A
1) manufacture of intermediate A -1
In three-neck flask, by iridous chloride (III) hydrate (15.0g, 42.5mmol) and 2- phenylpyridine (2.2g,
It 14.0mmol) is added together with cellosolvo (140ml), water (47ml), at argon atmospher stirred at reflux condition 18 hours.
It is cooled to room temperature, filtering precipitate, after washing drying with methanol and hexane, it is used for without further purification after reaction
Next reaction (21.7g, yield 95%).
2) manufacture of intermediate A
In three-neck flask, intermediate A -1 (20.0g, 18.7mmol) is added to CH2C12(1120ml) is stirred in room temperature
It mixes, is slowly added dropwise thereto and silver trifluoromethanesulfonate (10.1g, 39.2mmol) is dissolved in solution made of methanol (560ml),
And it is stirred overnight.After reaction, sellaite plug is utilizedAfter filtering reacting liquid, thickening filtration
Obtained solid is used in next reaction (25.8g. yield 97%) by liquid in the case where not being further purified.
Production Example 7: the manufacture of intermediate B
2- phenylpyridine is replaced to pass through the manufacturing method with intermediate A in addition to this using 5- methyl -2- phenylpyridine
Identical method has manufactured intermediate B.
Production Example 8: the manufacture of intermediate C
2- phenylpyridine is replaced to pass through the manufacture with intermediate A in addition to this using 5- (methyl-d3) -2- phenylpyridine
The identical method of method manufactures intermediate C.
[embodiment]
Embodiment 1: the manufacture of compound 1
In three-neck flask, intermediate A (20.0g, 28.0mmol), intermediate 1 (18.2g, 70.1mmol), ethyl alcohol is added
(140ml) and methanol (140ml), at argon atmospher stirred at reflux condition 20 hours.It is cooled to room temperature after reaction, uses ethyl alcohol
After dilution, sellaite is added and stirs 10 minutes.Then, in silica gel plugUpper filtering mixture, uses second
After pure and mild hexane washing, filtered fluid is discarded.Sellaite/silica gel plug CH2C12It washs and dissolves product, utilize isopropanol precipitating
And it filters.After the sediment of filtering isopropanol and hexane are washed and dried, sample is carried out after purification, most with silica gel column chromatography
Eventually by sublimation purification obtained compound 1 (4.3g, yield 10%, MS:[M+H]+=759).
Embodiment 2: the manufacture of compound 2
Intermediate 1 is replaced using intermediate 2, in addition to this, is manufactured by method identical with the manufacturing method of compound 1
Compound 2.
MS:[M+H]+=762
Embodiment 3: the manufacture of compound 3
Using intermediate B replace intermediate A, using intermediate 3 replace intermediate 1, in addition to this, by with compound 1
The identical method of manufacturing method manufactured compound 3.
MS:[M+H]+=849
Embodiment 4: the manufacture of compound 4
Using intermediate B replace intermediate A, using intermediate 4 replace intermediate 1, in addition to this, by with compound 1
The identical method of manufacturing method manufactured compound 4.
MS:[M+H]+=800
Embodiment 5: the manufacture of compound 5
Using intermediate C replace intermediate A, using intermediate 2 replace intermediate 1, in addition to this, by with compound 1
The identical method of manufacturing method manufactured compound 5.
MS:[M+H]+=796
Embodiment 6: the manufacture of compound 6
Using intermediate C replace intermediate A, using intermediate 5 replace intermediate 1, in addition to this, by with compound 1
The identical method of manufacturing method manufactured compound 6.
MS:[M+H] +=813
[experimental example]
Experimental example 1
It 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, is washed using ultrasonic wave.At this moment, Fei Xier company is used as detergent
The Decon of (Fischer Co.)TMCON705 product is made as distilled water using by Millipore Corp. (Millipore Co.)
The distilled water of 0.22 μm of sterilizing filter (sterilizing filter) filtering made twice.After ITO is washed 30 minutes, use
Distilled water is repeated twice and carries out 10 minutes ultrasonic washings.After distilling water washing, with isopropyl alcohol, acetone and first
After the solvent of alcohol carries out 10 minutes ultrasonic washings respectively and dries, it is delivered to plasma washing machine.In addition, utilizing oxygen etc.
Gas ions after five minutes by aforesaid substrate cleaning deliver the substrate to vacuum evaporation plating machine.
In the Π ' O transparent electrode prepared in this way withThickness thermal vacuum following 95 weights of HT-A compound are deposited
Measure % and following 5 weight of P-DOPANT compound mixture, then withThickness following HT-A compounds are only deposited
And form hole transmission layer.On above-mentioned hole transmission layer withThickness thermal vacuum be deposited following HT-B compounds and
Form electronic barrier layer.Then, on above-mentioned electronic barrier layer, by following GH compound (94 weights as material of main part
Measure %) and the above-mentioned manufacture as dopant compound 1 (6 weight %) mixture withThickness vacuum evaporation and
Form luminescent layer.Then, on above-mentioned luminescent layer, withThe following ET-A compounds of thickness vacuum evaporation and form
Hole blocking layer.Following ET-B compounds and following Liq compounds are mixed with the weight ratio of 2:1, and in above-mentioned hole
On barrier layer withThickness thermal vacuum vapor deposition and form electron transfer layer, then by LiF and magnesium with the weight ratio of 1:1 into
Row mixing, withThickness vacuum evaporation and form electron injecting layer.After magnesium and silver are mixed with the weight ratio of 1:4,
On above-mentioned electron injecting layer withThickness vapor deposition and form cathode, to manufacture organic illuminating element.
Experimental example 2 to 6
Compound 1 is replaced using the compound recorded in following table 1, in addition to this, using identical with above-mentioned experimental example 1
Method has made organic illuminating element respectively.
Comparative experiments example 1 to 5
Compound 1 is replaced using the compound recorded in following table 1, in addition to this, by identical with above-mentioned experimental example 1
Method has made organic illuminating element respectively.In following table 1, GD-1 to GD-5 difference is as follows.
Electric current is applied to the organic illuminating element by manufacturing in above-mentioned experimental example and comparative experiments example, respectively measurement electricity
It pressure, efficiency and service life (T95), the results are shown in following table 1.At this moment, voltage and efficiency are by applying 10mA/cm2's
Current density and measure, the service life (T95) indicate in 20mA/cm2Current density under time of original intensity when being reduced to 95%.
[table 1]
As shown in Table 1 above, with the R of chemical formula 1 of the invention1Position the case where being hydrogen compare, with chemical formula 1
The substance of structure makes the electron density of the phenyl ring bound directly with iridium change, this increases luminous efficiency.Therefore, work as use
In the case where luminescent layer dopant of the compound of chemical formula 1 of the invention as organic illuminating element, high efficiency can be obtained
With the organic illuminating element of long-life.
Symbol description
1: substrate 2: anode
3: luminescent layer 4: cathode
5: hole injection layer 6: hole transmission layer
7: luminescent layer 8: electron transfer layer.
Claims (7)
1. a kind of compound indicated by following chemical formula 1 or following chemical formula 2:
Chemical formula 1
Chemical formula 2
In the chemical formula 1 and 2,
X is O or S,
R1It is C that is unsubstituted or being replaced by deuterium1-60Alkyl, the silicyl of carbon atom number 1 to 60 or substituted or unsubstituted
C6-60Aryl,
R2And R3It is each independently hydrogen or C that is unsubstituted or being replaced by deuterium1-60Alkyl,
N is 1 or 2.
2. compound according to claim 1, wherein R1It is C that is unsubstituted or being replaced by deuterium1-5Alkyl, carbon atom number 3 to
10 silicyl or substituted or unsubstituted C6-10Aryl.
3. compound according to claim 1, wherein R1It is methyl, ethyl, propyl, isopropyl, butyl, isobutyl group, uncle
Butyl, amyl, isopentyl, tertiary pentyl, neopentyl, sec-amyl, 3- amyl, CD3、Si(CH3)3Or phenyl.
4. compound according to claim 1, wherein R2And R3It is each independently hydrogen or unsubstituted or replaced by deuterium
C1-5Alkyl.
5. compound according to claim 1, wherein R2And R3It is each independently hydrogen, methyl or CD3。
6. compound according to claim 1, wherein the compound is selected from any of following structures:
7. a kind of organic illuminating element comprising: first electrode, it is opposed with the first electrode and have second electrode,
And having 1 layer or more of organic matter layer between the first electrode and the second electrode, the organic matter layer includes
Luminescent layer, the luminescent layer include compound described in any one of claims 1 to 6.
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| CN111655705A (en) * | 2018-05-14 | 2020-09-11 | 株式会社Lg化学 | Organometallic compound and organic light emitting device including the same |
| EP4328285A1 (en) * | 2022-08-25 | 2024-02-28 | Beijing Summer Sprout Technology Co., Ltd. | Organic electroluminescent material and device thereof |
Citations (5)
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|---|---|---|---|---|
| CN103102371A (en) * | 2011-11-15 | 2013-05-15 | 通用显示公司 | Heteroleptic iridium complex |
| CN103936791A (en) * | 2013-12-12 | 2014-07-23 | 石家庄诚志永华显示材料有限公司 | Series organic electrophosphorescent material |
| CN104292272A (en) * | 2013-02-21 | 2015-01-21 | 环球展览公司 | A metal iridium complexes, devices containing the same, and formulations |
| CN105636971A (en) * | 2013-10-18 | 2016-06-01 | 罗门哈斯电子材料韩国有限公司 | Combination of a host compound and a dopant compound and organic electroluminescent device comprising the same |
| CN105646590A (en) * | 2014-11-28 | 2016-06-08 | 三星电子株式会社 | Organometallic compound and organic light-emitting device including the same |
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| KR100430549B1 (en) | 1999-01-27 | 2004-05-10 | 주식회사 엘지화학 | New organomattalic complex molecule for the fabrication of organic light emitting diodes |
| US8946697B1 (en) * | 2012-11-09 | 2015-02-03 | Universal Display Corporation | Iridium complexes with aza-benzo fused ligands |
| JP6582540B2 (en) * | 2015-05-15 | 2019-10-02 | コニカミノルタ株式会社 | ORGANIC ELECTROLUMINESCENT ELEMENT, METHOD FOR PRODUCING ORGANIC ELECTROLUMINESCENT ELEMENT, DISPLAY DEVICE AND LIGHTING DEVICE |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103102371A (en) * | 2011-11-15 | 2013-05-15 | 通用显示公司 | Heteroleptic iridium complex |
| CN104292272A (en) * | 2013-02-21 | 2015-01-21 | 环球展览公司 | A metal iridium complexes, devices containing the same, and formulations |
| CN105636971A (en) * | 2013-10-18 | 2016-06-01 | 罗门哈斯电子材料韩国有限公司 | Combination of a host compound and a dopant compound and organic electroluminescent device comprising the same |
| CN103936791A (en) * | 2013-12-12 | 2014-07-23 | 石家庄诚志永华显示材料有限公司 | Series organic electrophosphorescent material |
| CN105646590A (en) * | 2014-11-28 | 2016-06-08 | 三星电子株式会社 | Organometallic compound and organic light-emitting device including the same |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111655705A (en) * | 2018-05-14 | 2020-09-11 | 株式会社Lg化学 | Organometallic compound and organic light emitting device including the same |
| CN111655705B (en) * | 2018-05-14 | 2023-11-07 | 株式会社Lg化学 | Organometallic compound and organic light emitting device including the same |
| EP4328285A1 (en) * | 2022-08-25 | 2024-02-28 | Beijing Summer Sprout Technology Co., Ltd. | Organic electroluminescent material and device thereof |
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| KR20180080699A (en) | 2018-07-12 |
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