CN109836419A - Novel heterocyclic compounds and the organic illuminating element for utilizing it - Google Patents

Novel heterocyclic compounds and the organic illuminating element for utilizing it Download PDF

Info

Publication number
CN109836419A
CN109836419A CN201811228645.5A CN201811228645A CN109836419A CN 109836419 A CN109836419 A CN 109836419A CN 201811228645 A CN201811228645 A CN 201811228645A CN 109836419 A CN109836419 A CN 109836419A
Authority
CN
China
Prior art keywords
unsubstituted
substituted
chemical formula
alkyl
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201811228645.5A
Other languages
Chinese (zh)
Other versions
CN109836419B9 (en
CN109836419B (en
Inventor
河宰承
金渊焕
吴重锡
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LG Corp
Original Assignee
LG Chemical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by LG Chemical Co Ltd filed Critical LG Chemical Co Ltd
Publication of CN109836419A publication Critical patent/CN109836419A/en
Application granted granted Critical
Publication of CN109836419B publication Critical patent/CN109836419B/en
Publication of CN109836419B9 publication Critical patent/CN109836419B9/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Abstract

The present invention provides novel heterocyclic compounds and the organic illuminating element using it.

Description

Novel heterocyclic compounds and the organic illuminating element for utilizing it
Technical field
Cross reference to related applications
This application claims based on South Korea patent application the 10-2017-0158930th priority on November 24th, 2017, Full content as part of this specification disclosed in document comprising the South Korea patent application.
The present invention relates to novel heterocyclic compounds and include 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 and quick response time, and brightness, Driving voltage and response speed excellent, therefore carrying out numerous studies.
Organic illuminating element usually has the organic matter comprising anode and cathode and between above-mentioned anode and cathode The structure of layer.Wherein, in order to improve the efficiency and stability of organic illuminating element, above-mentioned organic matter layer is in most cases by multilayer Structure composition, and above-mentioned multilayered structure is made of respectively different substance, for example, can by hole injection layer, hole transmission layer, The formation such as luminescent layer, electron transfer layer, electron injecting layer.For the structure of such organic electroluminescent device, if Apply voltage between electrodes, then hole is injected into organic matter layer from anode, and electronics is injected into organic matter layer from cathode, works as institute Injected holes and electronics will form exciton (exciton) when meeting, and will send out when the exciton transits to ground state again Light out.
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 1: Korean Patent Publication No. the 10-2013-073537th
Summary of the invention
The present invention relates to comprising novel heterocyclic compounds compound and include its organic illuminating element.
The present invention provides the compound indicated by following chemical formula 1.
[chemical formula 1]
In above-mentioned chemical formula 1,
X1And X2It is each independently O or S,
L1Direct Bonding, substituted or unsubstituted C are each independently in recurring unit6-60Arlydene or comprising N, More than one substituted or unsubstituted C in O and S5-60Heteroarylidene,
R1To R3It is each independently hydrogen, deuterium, halogen group, cyano, three (C1-60Alkyl) it silicyl, substitution or does not take The C in generation1-60Alkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C1-60It is alkylthio, substituted or unsubstituted C3-60Naphthenic base, substituted or unsubstituted C6-60Aryl or comprising more than one substituted or unsubstituted in N, O and S C5-60Heteroaryl,
R4It is each independently comprising the more than one substituted or unsubstituted C in N, O and S5-60Heteroaryl, by cyano Substituted C6-60Aryl or three (C6-60Aryl) silicyl,
n1、n20 to 4 integer is each independently with m,
The integer that p is 0 to 4,
The integer that q is 1 to 4,
Wherein, 1≤p+q≤4,
When p and q are respectively 2 or more, the structure in 2 or more brackets is same or different to each other.
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, one layer or more in above-mentioned organic matter layer includes above-mentioned the compound of the present invention.
The above-mentioned compound indicated by chemical formula 1 may be used as the material of the organic matter layer of organic illuminating element, have The mention high and low driving voltage and/or life characteristic that efficiency may be implemented in machine light-emitting component improve.In particular, it is above-mentioned by The compound that chemical formula 1 indicates may be used as hole injection, hole transport, hole injection and transmission, luminous, electron-transport or Electron injection material.
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 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 constituted.
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
Specific embodiment
In the following, being illustrated in more details to help to understand the present invention.
The present invention provides the compound indicated by following chemical formula 1.
[chemical formula 1]
In above-mentioned chemical formula 1,
X1And X2It is each independently O or S,
L1Direct Bonding, substituted or unsubstituted C are each independently in recurring unit6-60Arlydene or comprising N, More than one substituted or unsubstituted C in O and S5-60Heteroarylidene.
R1To R3It is each independently hydrogen, deuterium, halogen group, cyano, three (C1-60Alkyl) it silicyl, substitution or does not take The C in generation1-60Alkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C1-60It is alkylthio, substituted or unsubstituted C3-60Naphthenic base, substituted or unsubstituted C6-60Aryl or comprising more than one substituted or unsubstituted in N, O and S C5-60Heteroaryl,
R4It is each independently comprising the more than one substituted or unsubstituted C in N, O and S5-60Heteroaryl, by cyano Substituted C6-60Aryl or three (C6-60Aryl) silicyl,
n1、n20 to 4 integer is each independently with m,
The integer that p is 0 to 4,
The integer that q is 1 to 4,
Wherein, 1≤p+q≤4,
When p and q are respectively 2 or more, the structure in 2 or more brackets is same or different to each other.
In this specification,Refer to 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- or comprising more than one in the more than one heterocycle in N, O and S atom Substituent group is substituted or unsubstituted, or the substituent group being formed by connecting by more than two substituent groups in foregoing illustrative substituent group Replace.For example, " substituent group that more than two substituent groups are formed by connecting " can be xenyl.That is, xenyl can be aryl, It 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 structure as described below, but not limited to this.
In this specification, for ester group, the oxygen of ester group can be by the straight chain of carbon atom number 1 to 25, branch or cricoid Alkyl or the aryl of carbon atom number 6 to 25 replace.Specifically, can be the compound of following structural formula, but it is 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 structure, 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- (hexichol -1- base) ethylene -1- base, Stilbene base, styryls etc., but not It is defined in 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, above-mentioned fluorenyl can be substituted, and adjacent group can be bonded to each other and form ring.
In the substituted situation of above-mentioned fluorenyl, Ke Yiwei Deng but not limited to this.
In this specification, " adjacent " group can refer to be taken on the atom that the atom replaced with the substituent group is directly connected to Replace on the substituent group in generation, stereochemical structure in the substituent group with the immediate position of the substituent group or in the substituent group Other substituent groups replaced on atom.For example, same in the adjacent position (ortho) replaces in phenyl ring 2 substituent groups and aliphatic ring 2 substituent groups replaced on carbon can be construed to " adjacent " group each other.
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, triazolyl, Acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolyl, quinoxalinyl, phthalazinyl, Pyridopyrimidine base, pyrido-pyrazine Base, pyrazine and pyrazinyl, isoquinolyl, indyl, carbazyl, benzoOxazolyl, benzimidazolyl, benzothiazolyl, benzo It is carbazyl, benzothienyl, dibenzothiophene, benzofuranyl, phenanthroline (phenanthroline), thiazolyl, differentOxazolyl,Di azoly, thiadiazolyl group, benzothiazolyl, phenothiazinyl and dibenzofuran group etc., it is 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 example of abovementioned alkyl.This specification In, the heteroaryl in heteroaryl amine can apply with respect to the explanation of above-mentioned heterocycle.In this specification, alkenyl in arylalkenyl with The example of above-mentioned alkenyl is identical.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.
Preferably, it can be by the compound that above-mentioned chemical formula 1 indicates by any of following chemical formula 1-1 and 1-2 table The compound shown.
[chemical formula 1-1]
[chemical formula 1-2]
In above-mentioned chemical formula 1-1 and 1-2,
X1、X2、L1、R1、R2、R3、R4、n1、n2It is as defined above with m.
Preferably, X1And X2It can be O.
Preferably, L1And L2Direct Bonding can be each independently or selected from any one of following radicals.
It is highly preferred that L1And L2Can be each independently Direct Bonding,
Preferably, R1、R2And R3Hydrogen can be each independently.
Preferably, R4It can be indicated by any of following chemical formula 2 to 10.
[chemical formula 2]
[chemical formula 3]
[chemical formula 4]
[chemical formula 5]
[chemical formula 6]
[chemical formula 7]
[chemical formula 8]
[chemical formula 9]
[chemical formula 10]
In above-mentioned chemical formula 2 to 6,
G1To G30In include either one or two of in each chemical formula for the L with chemical formula 11The position of bonding,
In addition to the L with chemical formula 11Remaining G except the position of bonding1To G30It is each independently hydrogen, deuterium, itrile group, nitre Base, hydroxyl, carbonyl, ester group, imide, amide groups, substituted or unsubstituted C1-60Alkyl, substituted or unsubstituted C3-60Ring Alkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C6-60Aryloxy group, substituted or unsubstituted C1-60Alkyl Sulfenyl, substituted or unsubstituted C6-60Artyl sulfo, substituted or unsubstituted C2-60Alkenyl, substituted or unsubstituted C1-60Alkyl Silicyl, substituted or unsubstituted C1-60Alkyl boryl, substituted or unsubstituted C1-60It is alkyl amine group, substituted or unsubstituted C6-60Aryl includes the more than one substituted or unsubstituted C in N, O and S5-60Heteroaryl,
In above-mentioned chemical formula 7,
X1' to X3' it is each independently N or CR1',
G31To G33And R1' any of be L with chemical formula 11The position of bonding,
In addition to the L with chemical formula 11Remaining G except the position of bonding31To G33And R1' it is each independently hydrogen, deuterium, nitrile Base, nitro, hydroxyl, carbonyl, ester group, imide, amide groups, substituted or unsubstituted C1-60It is alkyl, substituted or unsubstituted C3-60Naphthenic base, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C6-60It is aryloxy group, substituted or unsubstituted C1-60Alkyl sulfenyl, substituted or unsubstituted C6-60Artyl sulfo, substituted or unsubstituted C2-60It is alkenyl, substituted or unsubstituted C1-60AIkylsilyl groups, substituted or unsubstituted C1-60Alkyl boryl, substituted or unsubstituted C1-60Alkyl amine group, substitution or Unsubstituted C6-60Aryl includes the more than one substituted or unsubstituted C in N, O and S5-60Heteroaryl, wherein X1' extremely X3' it is all CR1' when, R1' any of be itrile group,
In above-mentioned chemical formula 8,
X4' to X7' it is each independently N or CR2', wherein X4' to X7' at least one be N,
G34To G39And R2' any of for L with chemical formula 11The position of bonding,
In addition to the L with chemical formula 11G except the position of bonding34To G39And R2' it is each independently hydrogen, deuterium, itrile group, nitre Base, hydroxyl, carbonyl, ester group, imide, amide groups, substituted or unsubstituted C1-60Alkyl, substituted or unsubstituted C3-60Ring Alkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C6-60Aryloxy group, substituted or unsubstituted C1-60Alkyl Sulfenyl, substituted or unsubstituted C6-60Artyl sulfo, substituted or unsubstituted C2-60Alkenyl, substituted or unsubstituted C1-60Alkyl Silicyl, substituted or unsubstituted C1-60Alkyl boryl, substituted or unsubstituted C1-60It is alkyl amine group, substituted or unsubstituted C6-60Aryl includes the more than one substituted or unsubstituted C in N, O and S5-60Heteroaryl,
In above-mentioned chemical formula 9,
Y1' it is O, S, NR3' or CR4’R5',
G40To G44And R3' to R5' any of for L with chemical formula 11The position of bonding,
In addition to the L with chemical formula 11G except the position of bonding40To G44And R3' to R5' it is each independently hydrogen, deuterium, nitrile Base, nitro, hydroxyl, carbonyl, ester group, imide, amide groups, substituted or unsubstituted C1-60It is alkyl, substituted or unsubstituted C3-60Naphthenic base, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C6-60It is aryloxy group, substituted or unsubstituted C1-60Alkyl sulfenyl, substituted or unsubstituted C6-60Artyl sulfo, substituted or unsubstituted C2-60It is alkenyl, substituted or unsubstituted C1-60AIkylsilyl groups, substituted or unsubstituted C1-60Alkyl boryl, substituted or unsubstituted C1-60Alkyl amine group, substitution or Unsubstituted C6-60Aryl includes the more than one substituted or unsubstituted C in N, O and S5-60Heteroaryl, adjacent group can Substituted or unsubstituted ring is formed to be bonded to each other,
In above-mentioned chemical formula 10,
Y2' it is O, S, NR6' or CR7’R8',
X8' and X9' it is each independently N or CR9',
G45、G46And R6' to R9' any of for L with chemical formula 11The position of bonding,
In addition to the L with chemical formula 11G except the position of bonding45、G46And R6' to R9' it is each independently hydrogen, deuterium, nitrile Base, nitro, hydroxyl, carbonyl, ester group, imide, amide groups, substituted or unsubstituted C1-60It is alkyl, substituted or unsubstituted C3-60Naphthenic base, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C6-60It is aryloxy group, substituted or unsubstituted C1-60Alkyl sulfenyl, substituted or unsubstituted C6-60Artyl sulfo, substituted or unsubstituted C2-60It is alkenyl, substituted or unsubstituted C1-60AIkylsilyl groups, substituted or unsubstituted C1-60Alkyl boryl, substituted or unsubstituted C1-60Alkyl amine group, substitution or Unsubstituted C6-60Aryl includes the more than one substituted or unsubstituted C in N, O and S5-60Heteroaryl.
Preferably, in the compound indicated by above-mentioned chemical formula 2 to 6, G1To G30In be included in each chemical formula in Either one or two of for L with chemical formula 11The position of bonding, in addition to the L with chemical formula 11G except the position of bonding1To G30Respectively It independently is hydrogen, substituted or unsubstituted C6-60Aryl or include the substituted or unsubstituted of 1 or more in N, O and S C5-60Heteroaryl.
Preferably, the compound indicated by above-mentioned chemical formula 7 can be any selected from following chemical formula 7-1 into 7-4 It is a.
In formula, G31To G33And R1' as defined above, it is highly preferred that G31To G33And R1' any of be and chemistry The L of formula 11The position of bonding, in addition to the L with chemical formula 11Remaining G except the position of bonding31To G33And R1It is each independently Hydrogen, substituted or unsubstituted C6-60Aryl or include the more than one substituted or unsubstituted C in N, O and S5-60Heteroaryl Base.
Preferably, the compound indicated by above-mentioned chemical formula 8 is appointing into chemical formula 8-8 selected from following chemical formula 8-1 One.
In formula, G34To G39And R2' as defined above, it is highly preferred that G34To G39And R2' any of be and chemistry The L of formula 11The position of bonding, in addition to the L with chemical formula 11Remaining G except the position of bonding34To G39And R2' each independently For hydrogen, substituted or unsubstituted C6-60Aryl or include 1 or more substituted or unsubstituted C in N, O and S5-60Heteroaryl Base.
Preferably, the compound indicated by above-mentioned chemical formula 9 can for selected from following chemical formula 9-1 into chemical formula 9-5 Either one or two of.
Above-mentioned chemical formula 9-1 is into chemical formula 9-4, G40To G43And R3' to R5' as defined above, it is highly preferred that G40 To G43And R3' to R5' any of for L with chemical formula 11The position of bonding, in addition to the L with chemical formula 11The position of bonding it Remaining outer G40To G43And R3' to R5' it is each independently hydrogen or substituted or unsubstituted aryl.
In above-mentioned chemical formula 9-5, G40To G43And G1' to G8' any of for L with chemical formula 11The position of bonding, is removed L with chemical formula 11Remaining G except the position of bonding40To G43And G1' to G8' it is each independently hydrogen, deuterium, itrile group, nitre Base, hydroxyl, carbonyl, ester group, imide, amide groups, substituted or unsubstituted C1-60Alkyl, substituted or unsubstituted C3-60Ring Alkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C6-60Aryloxy group, substituted or unsubstituted C1-60Alkyl Sulfenyl, substituted or unsubstituted C6-60Artyl sulfo, substituted or unsubstituted C2-60Alkenyl, substituted or unsubstituted C1-60Alkyl Silicyl, substituted or unsubstituted C1-60Alkyl boryl, substituted or unsubstituted C1-60It is alkyl amine group, substituted or unsubstituted C6-60Aryl includes the more than one substituted or unsubstituted C in N, O and S5-60Heteroaryl.
It is highly preferred that G40To G43And G1' to G8' any of for L with chemical formula 11The position of bonding, in addition to change The L of formula 11Remaining G except the position of bonding40To G43And G1' to G8' it is each independently hydrogen, substituted or unsubstituted C6-60Aryl or include the more than one substituted or unsubstituted C in N, O and S5-60Heteroaryl.
Preferably, the compound indicated by above-mentioned chemical formula 10 can be for selected from following chemical formula 10-1 to chemical formula 10-9 Any of.
In formula, G45、G46And R6' and R9' as defined above, it is highly preferred that G45、G46And R6' and R9' in it is any A L for chemical formula 11The position of bonding, in addition to the L with chemical formula 11Remaining G except the position of bonding45、G46And R6’ And R9' it is each independently hydrogen, substituted or unsubstituted C6-60Aryl or comprising in N, O and S more than one substitution or Unsubstituted C5-60Heteroaryl.
Preferably, R4It can be for selected from any of following radicals.
In above-mentioned group,
R5It is each independently hydrogen, substituted or unsubstituted C6-60It aryl or is taken comprising more than one in N, O and S Generation or unsubstituted C5-60Heteroaryl.
Preferably, m can be 0 or 1.
Preferably, the compound indicated by above-mentioned chemical formula 1 can be for selected from any of following radicals.
The compound indicated by above-mentioned chemical formula 1 can be by manufacturing methods such as such as following reaction equation 1-A or reaction equation 1-B Manufacture.Above-mentioned manufacturing method can be more specific in aftermentioned Production Example.
[reaction equation 1-A]
[reaction equation 1-B]
In above-mentioned reaction equation 1-A or reaction equation 1-B,
X1、X2、R4Deng identical as the definition in chemical formula 1.
Reactant used in above-mentioned reaction equation, catalyst, solvent etc. and reaction condition etc. can be according to the present invention It changes and uses to the type of the substituent group of chemical formula 1 and location-appropriate, specifically, aftermentioned Production Example can be embodied as 1 to 4.
In addition, the present invention provides the organic illuminating element of the compound comprising being indicated by above-mentioned chemical formula 1.As an example Son, the present invention a kind of organic illuminating element is provided comprising: first electrode, it is opposed with above-mentioned first electrode and have Two electrodes 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 One layer or more the compound comprising being indicated by above-mentioned chemical formula 1 in nitride layer.
The organic matter layer of organic illuminating element of the invention can be formed by single layer structure, can also by be laminated with 2 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 lesser amount of organic layer.
In addition, above-mentioned organic matter layer may include hole injection layer, hole transmission layer or carry out hole injection and biography simultaneously Defeated layer, above-mentioned hole injection layer, hole transmission layer or to carry out the layer of hole injection and transmission simultaneously include by above-mentioned chemical formula 1 compound indicated.
In addition, above-mentioned organic matter layer may include luminescent layer, above-mentioned luminescent layer includes the chemical combination indicated by above-mentioned chemical formula 1 Object.
In addition, above-mentioned organic matter layer may include electron transfer layer or electron injecting layer, above-mentioned electron transfer layer or electronics Implanted layer includes the compound indicated by above-mentioned chemical formula 1.
In addition, above-mentioned electron transfer layer, electron injecting layer or carry out simultaneously electron injection and electron-transport layer include by The compound that above-mentioned chemical formula 1 indicates.In particular, the thermal stability of the compound according to the present invention indicated by chemical formula 1 is excellent Different, deep HOMO energy level, high triplet with 6.0eV or more can (ET) and hole stability.In addition, will be by above-mentionedization When the compound that formula 1 indicates for that can carry out the organic matter layer of electron injection and electron-transport simultaneously, ability can be mixed N-type dopant used in domain and use.
In addition, above-mentioned organic matter layer includes luminescent layer and electron transfer layer, above-mentioned electron transfer layer be may include by above-mentioned The compound that chemical formula 1 indicates.
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 organic Light-emitting component (can be inverted for the reverse structure of the organic matter layer and anode that are sequentially laminated with cathode, one layer or more on substrate Type, inverted type) organic illuminating element.For example, the structure of the organic illuminating element of an embodiment according to the present invention It is illustrated in Fig. 1 and 2.
Fig. 1 illustrates the examples for the organic illuminating element being made of 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 indicates.
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 constituted.In this configuration, it may include by the compound that above-mentioned chemical formula 1 indicates One layer or more in above-mentioned hole injection layer, hole transmission layer, luminescent layer and electron transfer layer.
Organic illuminating element according to the present invention includes by above-mentioned chemical formula 1 in addition to one layer or more in above-mentioned organic matter layer Other than the compound of expression, material well known to the technical field and method manufacture can use.In addition, when above-mentioned organic light emission member In the case that part includes multiple organic matter layers, 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 method (sputtering) or electron beam evaporation method (e- Beam evaporation) etc PVD (physical vapor deposition, physical Vapor Deposition) method, steamed on substrate Plating metal or conductive metal oxide or their alloy and form anode, then on the anode formed comprising sky Cave implanted layer, hole transmission layer, luminescent layer and electron transfer layer organic matter layer, later on organic matter layer vapor deposition can be used as yin The substance of pole and manufacture.In addition to this approach, can also on substrate successively evaporation cathode substance, organic matter layer, anode Substance and manufacture organic illuminating element.
In addition, when manufacturing organic illuminating element, not only can use true about the compound that above-mentioned chemical formula 1 indicates 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.
In addition to this approach, can also on substrate successively evaporation cathode substance, organic matter layer, anode material and make Make organic illuminating element (WO2003/012890).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 cathode substance, have the metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminium, silver, tin and lead or it Alloy；LiF/Al or LiO2Multilayered structures substance such as/Al etc., it is 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, have the organic matter of aryl amine system, electroconductive polymer and The block copolymer etc. of conjugate moiety and non-conjugated portion is existed simultaneously, it is not limited to this.
It is that can receive respectively hole and electronics from hole transmission layer and electron transfer layer and make as above-mentioned luminescent substance They in conjunction with and issue the substance of the light of visible light region, preferably for the high substance of the quantum efficiency of fluorescence or phosphorescence.As Concrete example has 8- Hydroxy-quinolin aluminum complex (Alq3)；Carbazole based compound；Two polystyrene-based (dimerized Styryl) compound；BAlq；10- hydroxy benzo quinoline-metallic compound；BenzoAzoles, benzothiazole and benzimidazole system Compound；Poly- (to phenylene vinylidene) (PPV) is macromolecule；Loop coil (spiro) compound；Polyfluorene, rubrene etc., but simultaneously It is not limited only to this.
Above-mentioned luminescent layer may include material of main part and dopant material.Material of main part has aromatic fused ring derivative or contains Heterocyclic compound etc..Specifically, having anthracene derivant, pyrene derivatives, naphthalene derivatives and five as aromatic fused ring derivative Benzene derivative, phenanthrene compound, fluoranthene compound etc. have carbazole derivates, dibenzofurans derivative as nitrogen-containing heterocgcies Object, ladder type furan compoundPyrimidine derivatives etc., but not limited to this.
Dopant material has aromatic amine derivative, styrylamine compound, boron complexes, fluoranthene compound, metal to match Close object etc..Specifically, being that there is the aromatic fused ring of substituted or unsubstituted arylamino to spread out as aromatic amine derivative Biology, have pyrene with arylamino, anthracene,Two indeno pyrenes (Periflanthene) etc., as styryl amine compounds Object is to replace the compound for having at least one aryl vinyl on substituted or unsubstituted arylamine, is selected from aryl, first silicon Substituent group more than one or two of alkyl, alkyl, naphthenic base and arylamino is substituted or unsubstituted.Specifically, There are styryl amine, styryl diamines, styryl triamine, styryl tetramine etc., but not limited to this.In addition, making For metal complex, there are complex of iridium, platinum complex etc., but not limited to this.
Above-mentioned electron-transport is to pass from electron injecting layer reception electronics and by the layer of electron-transport to luminescent layer as electronics Defeated substance is can to receive well electronics from cathode and transfer them to the substance of luminescent layer, the big substance of electron mobility It is suitable.As concrete example, there is the Al complex of 8-hydroxyquinoline, comprising Alq3Complex, organic free radical compound, Flavonol-metal complex etc., but not limited to this.Electron transfer layer can as used in the prior art like that with The cathode substance of any desired is used together.In particular, the example of suitable cathode substance is with low work function and with aluminium The common substance of layer or silver layer.Specially caesium, barium, calcium, ytterbium and samarium, for above-mentioned each substance, with aluminium layer or silver Layer.
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 five-membered ring derivative Deng but not limited to this.
As above-mentioned metal complex, there are 8-hydroxyquinoline lithium, bis- (8-hydroxyquinoline) zinc, bis- (8-hydroxyquinolines) Copper, bis- (8-hydroxyquinoline) manganese, three (8-hydroxyquinoline) aluminium, three (2- methyl -8-hydroxyquinoline) aluminium, three (8-hydroxyquinolines) Gallium, bis- (10- hydroxy benzo [h] quinoline) berylliums, bis- (10- hydroxy benzo [h] quinoline) zinc, bis- (2- methyl -8- quinoline) gallium chlorides, Bis- (2- methyl -8- quinoline) (o-cresol) galliums, bis- (2- methyl -8- quinoline) (1- naphthols) aluminium, bis- (2- methyl -8- quinoline) (2- Naphthols) 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 other than organic illuminating element, be further included in it is organic too Positive energy battery or organic transistor.
The compound indicated by above-mentioned chemical formula 1 and the manufacture comprising its organic illuminating element have in the examples below Body it is illustrated.But following embodiments are for illustrating the present invention, it's not limited to that for the scope of the present invention.
Production Example 1 (synthesis of B1 to B4)
[reaction equation 1-1]
The synthesis of B1
According to above-mentioned reaction equation 1-1, by bromo- 1, the 2- difluorobenzene of A1 (30g, 64.8mmol), 4- (18.76g, 97.20mmol), potassium carbonate (37.61,272.2mmol) is added to DMF (300ml), return stirring.After reaction, it is cooled to Room temperature, filtering.After room temperature water and chloroform (chlroform) are extracted, by white solid ethyl acetate and hexane column Chromatography, to manufacture above-mentioned B1 (18.82g, yield 80%).
MS[M+H]+=364.21
The synthesis of B2
In the synthesis of above-mentioned B1, bromo- 1, the 2- difluorobenzene of 4- is replaced to pass through in addition to this using bromo- 2, the 3- difluorobenzene of 1- Identical method synthesizes and has manufactured B2.
MS[M+H]+=364.21
The synthesis of B3
In the synthesis of above-mentioned B1, bromo- 1, the 2- difluorobenzene of 4- is replaced using chloro- 4, the 5- difluorobenzene of 1,2- bis-, in addition to this, It is synthesized by identical method and has manufactured B3.
MS[M+H]+=354.20
The synthesis of B4
In the synthesis of above-mentioned B1, bromo- 1, the 2- difluorobenzene of 4- is replaced using chloro- 2, the 3- difluorobenzene of Isosorbide-5-Nitrae-two, in addition to this, It is synthesized by identical method and has manufactured B4.
MS[M+H]+=354.20
Production Example 2 (synthesis of C1 to C8)
The synthesis of C1 to C2
[reaction equation 2-1]
The synthesis of C1
Under nitrogen atmosphere, by above compound B1 (25g, 68.83mmol), bis- (pinacol combined) two boron (20.97g, It 82.59mmol) is mixed with potassium acetate (23.65g, 240.9mmol), addition twoAlkane (300ml), is heated while stirring. At reflux, bis- (dibenzalacetone) palladiums (1.19g, 3mol%) and tricyclohexyl phosphine (1.13g, 6mol%) is added, Heating, stirring 3 hours.After reaction, room temperature is cooled the temperature to, is then filtered.Water is poured into filtered fluid, is extracted with chloroform, Organic layer has been dried with anhydrous magnesium sulfate.After vacuum distillation, recrystallized with tetrahydrofuran and ethyl acetate, to manufacture above-mentioned C1 (28.23g, 83%).
MS[M+H]+=411.28
The synthesis of C2
B1 is replaced to synthesize by identical method in addition to this and manufactured C2 using B2 in the synthesis of above-mentioned C1.
MS[M+H]+=411.28
The synthesis of C3 to C5
[reaction equation 2-2]
The synthesis of B1-1
According to above-mentioned reaction equation 2-2, B1 (25g, 68.83mmol) and 4- chlorophenylboronic acid (11.30g, 72.27mmol) are added After being added to tetrahydrofuran (300ml), add 2M wet chemical (150ml), addition tetrakis triphenylphosphine palladium (1.59g, After 2mol%), heating stirring 10 hours.Room temperature is cooled the temperature to, after reaction was completed, wet chemical is removed and carries out layer point From.After removing solvent, white solid ethyl acetate is recrystallized and has manufactured above-mentioned B1-1 (23.1g, yield 85%).
MS[M+H]+=395.85
The synthesis of B1-2
In the synthesis of above-mentioned B1-1,4- chlorophenylboronic acid is replaced to pass through identical side in addition to this using 3- chlorophenylboronic acid Method synthesizes and has manufactured B1-2.
MS[M+H]+=395.85
The synthesis of B1-3
In the synthesis of above-mentioned B1-1,4- chlorophenylboronic acid is replaced to pass through identical side in addition to this using 2- chlorophenylboronic acid Method synthesizes and has manufactured B1-3.
MS[M+H]+=395.85
The synthesis of C3
In the synthesis of above-mentioned C1, B1 is replaced to synthesize and manufacture by identical method in addition to this using B1-1 C3。
MS[M+H]+=487.37
The synthesis of C4
In the synthesis of above-mentioned C3, B1-1 is replaced to synthesize and manufacture by identical method in addition to this using B1-2 C4。
MS[M+H]+=487.37
The synthesis of C5
In the synthesis of above-mentioned C3, B1-1 is replaced to synthesize and manufacture by identical method in addition to this using B1-3 C5。
MS[M+H]+=487.37
The synthesis of C6 to C8
[reaction equation 2-3]
The synthesis of B2-1
According to above-mentioned reaction equation 2-3, in the synthesis of above-mentioned B1-1, B1 is replaced using B2, in addition to this, by identical Method synthesizes and has manufactured B2-1.
MS[M+H]+=395.85
The synthesis of B2-2
In the synthesis of above-mentioned B2-1,4- chlorophenylboronic acid is replaced to pass through identical side in addition to this using 3- chlorophenylboronic acid Method synthesizes and has manufactured B2-2.
MS[M+H]+=395.85
The synthesis of B2-3
In the synthesis of above-mentioned B2-1,4- chlorophenylboronic acid is replaced to pass through identical side in addition to this using 2- chlorophenylboronic acid Method synthesizes and has manufactured B2-3.
MS[M+H]+=395.85
The synthesis of C6
In the synthesis of above-mentioned C3, B1-1 is replaced to synthesize and manufacture by identical method in addition to this using B2-1 C6。
MS[M+H]+=487.37
The synthesis of C7
In the synthesis of above-mentioned C6, B2-1 is replaced to synthesize and manufacture by identical method in addition to this using B2-2 C7。
MS[M+H]+=487.37
The synthesis of C8
In the synthesis of above-mentioned C6, B2-1 is replaced to synthesize and manufacture by identical method in addition to this using B2-3 C8。
MS[M+H]+=487.37
Production Example 3 (synthesis of D1 to D2)
[reaction equation 3-1]
The synthesis of D1-1
According to above-mentioned reaction equation 3-1, in the synthesis of above-mentioned B1-1, the chloro- 4- phenyl -6- of 2- (3- (pyridine -2- base) is used Phenyl -1,3,5-triazines replaces B1, uses (6- hydroxyl naphthalene -2- base) boric acid to replace 4- chlorophenylboronic acid, in addition to this, by identical Method synthesis and manufactured D1-1.
MS[M+H]+=453.52
The synthesis of D1
Chloroform (400ml) is added in D1-1 (30g, 110.9mmol) after dissolution, and perfluoro butyl is slowly added dropwise in room temperature Sulfuryl fluoride (36.85g, 121.9mmol) is stirred at room temperature 3 hours.In room temperature, after water and chloroform (chlroform) extraction, White solid hexane is recrystallized and has manufactured above compound B2-2 (56.97g, yield 93%).
MS[M+H]+=735-60
[reaction equation 3-2]
The synthesis of D2-1
According to above-mentioned reaction equation 3-2, in the synthesis of above-mentioned B1-1,2- chloro- 4,6- diphenyl -1,3,5-triazines generation is used For B1, (7- hydroxyl -9,9- dimethyl -9H- fluorenes -2- base) boric acid is used to replace 4- chlorophenylboronic acid, in addition to this, by identical Method synthesizes and has manufactured D2-1.
MS[M+H]+=442.53
The synthesis of D2
In the synthesis of above-mentioned D1, D1-1 is replaced to synthesize and manufacture by identical method in addition to this using D2-1 D2。
MS[M+H]+=724.61
Production Example 4 (synthesis of compound 1 to 21)
The synthesis of compound 1
[reaction equation 4-1]
By C1 (25g, 68.83mmol) and 2- ([1,1'- xenyl] -4- base) -4- chloro-6-phenyl -1,3,5- triazine It after (11.30g, 72.27mmol) is added to tetrahydrofuran (300ml), adds 2M wet chemical (150ml), is added four (three Phenylphosphine) after palladium (1.59g, 2mol%), heating stirring 10 hours.Room temperature is cooled the temperature to, after reaction was completed, removes potassium carbonate Aqueous solution and carry out layer separation.After removing solvent, white solid is recrystallized with ethyl acetate, to manufacture above compound 1 (23.1g, yield 85%).
MS[M+H]+=592.67
The synthesis of compound 2
[reaction equation 4-2]
In the synthesis of above compound 1, use 2,4- bis- (1,1 '-xenyl) 4- yl) -6- chlorine pyrimidine replace 2- ([1, 1 '-xenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines synthesized by identical method in addition to this and manufactured change Close object 2.
MS[M+H]+=667.78
The synthesis of compound 3
[reaction equation 4-3]
In the synthesis of above compound 1, C1 is replaced using C2, using the chloro- 4- phenyl -6- of 2- (triphenylene -2- base) -1, 3,5- triazines replace 2- ([1,1 '-xenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines, in addition to this, by identical Method synthesizes and has manufactured compound 3.
MS[M+H]+=666.75
The synthesis of compound 4
[reaction equation 4-4]
In the synthesis of above compound 1, C1 is replaced using C3, uses 2- ([1,1 '-xenyl] -3- base) the chloro- 6- of -4- Phenyl -1,3,5-triazines replaces 2- ([1,1 '-xenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines, in addition to this, leads to It crosses identical method synthesis and has manufactured compound 4.
MS[M+H]+=668.77
The synthesis of compound 5
[reaction equation 4-5]
In the synthesis of above compound 1, using C3 replace C1, using chloro- 4, the 6- diphenylpyrimidin of 2- replace 2- ([1, 1 '-xenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines synthesized by identical method in addition to this and manufactured change Close object 5.
MS[M+H]+=591.68
The synthesis of compound 6
[reaction equation 4-6]
In the synthesis of above compound 1, C1 is replaced using C4, using the chloro- 4- of 2- (4- chlorphenyl) -6- phenyl -1,3, 5- triazine replaces 2- ([1,1 '-xenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines to pass through identical side in addition to this Method synthesizes and has manufactured int.1.
MS[M+H]+=627.11
Secondly, replacing C1 in the synthesis of above compound 1 using the int.1 of above-mentioned manufacture, using dibenzofurans- 4- boric acid replaces 2- ([1,1 '-xenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines to pass through identical side in addition to this Method synthesizes and has manufactured compound 6.
MS[M+H]+=758.85
The synthesis of compound 7
[reaction equation 4-7]
In the synthesis of above compound 1, C1 is replaced using C4, uses the chloro- 2- of 4- (naphthalene -1- base) -6- phenyl pyrimidine generation It is synthesized in addition to this by identical method for 2- ([1,1 '-xenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines Compound 7 is manufactured.
MS[M+H]+=641.74
The synthesis of compound 8
[reaction equation 4-8]
C1 is replaced using C5 in the synthesis of above compound 1, uses the chloro- 4- of 2- (4- chlorphenyl) -6- phenyl -1,3,5- Triazine replaces 2- ([1,1 '-xenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines to pass through identical method in addition to this It synthesizes and has manufactured int.2.
MS[M+H]+=627.11
By the Int.2 (15g, 26.4mmol), 9H- carbazole (15g, 27.3mmol), sodium tert-butoxide of above-mentioned manufacture (4.56g, It 59.2mol) is added in dimethylbenzene, flows back after heating stirring, [bis- (tri-tert-butylphosphines)] palladium (269mg.2mmol%) is added. Room temperature is cooled the temperature to, after reaction was completed, is recrystallized using tetrahydrofuran and ethyl acetate, to manufacture compound 8 (15.08g, 82%).
MS[M+H]+=757.87
The synthesis of compound 9
[reaction equation 4-9]
In the synthesis of above compound 1,2- ([1,1 '-is replaced using 4- chloro-6-phenyl -2- (pyridine -2- base) pyrimidine Xenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines is synthesized by identical method in addition to this, to manufacture change Close object 9.
MS[M+H]+=592.67
The synthesis of compound 10
[reaction equation 4-10]
In the synthesis of above compound 1, C1 is replaced using C6, uses 4- ([1,1 '-xenyl] -3- base) the chloro- 6- of -2- Phenyl pyrimidine replaces 2- ([1,1 '-xenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines, in addition to this, by identical Method synthesis, to manufacture compound 10.
MS[M+H]+=667.78
The synthesis of compound 11
[reaction equation 4-11]
In the synthesis of above compound 1, C1 is replaced using C6, uses the chloro- 4- of 2- (9,9- dimethyl -9H- fluorenes -2- Base) -6- phenyl -1,3,5-triazines replace 2- ([1,1 '-xenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines, except this with Outside, it is synthesized by identical method and has manufactured compound 11.
MS[M+H]+=708.83
The synthesis of compound 12
[reaction equation 4-12]
In the synthesis of above compound 1, C1 is replaced using C7, uses the chloro- 4- of 2- (phenanthrene -2- base) -6- phenyl pyrimidine generation It is synthesized in addition to this by identical method for 2- ([1,1 '-xenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines Compound 12 is manufactured.
MS[M+H]+=691.81
The synthesis of compound 13
[reaction equation 4-13]
In the synthesis of above compound 1, C1 is replaced using C7, uses 2- ([1,1 '-xenyl] -3- base) the chloro- 6- of -4- Phenyl -1,3,5-triazines replaces 2- ([1,1 '-xenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines, in addition to this, leads to It crosses identical method synthesis and has manufactured compound 13.
MS[M+H]+=668.77
The synthesis of compound 14
[reaction equation 4-14]
In the synthesis of above compound 1, C1 is replaced using C8, uses 2- ([1,1 '-xenyl] -2- base) the chloro- 6- of -4- Phenyl -1,3,5-triazines replaces 2- ([1,1 '-xenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines, in addition to this, leads to It crosses identical method synthesis and has manufactured compound 14.
MS[M+H]+=667.78
The synthesis of compound 15
[reaction equation 4-15]
In the synthesis of above compound 1, C1 is replaced using C8, using the chloro- 4- of 2- (3- chlorphenyl) -6- phenyl -1,3, 5- triazine replaces 2- ([1,1 '-xenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines to pass through identical side in addition to this Method synthesizes and has manufactured int.3.
MS[M+H]+=627.11
In the synthesis of above compound 1, C1 is replaced using the int.3 of above-mentioned manufacture, uses (3- cyano-phenyl) boric acid It is synthesized in addition to this by identical method instead of 2- ([1,1 '-xenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines And compound 15 is manufactured.
MS[M+H]+=693.78
The synthesis of compound 16
[reaction equation 4-16]
In the synthesis of above compound 1,2- ([1,1 '-xenyl]-4- base) chloro-6-phenyl-1-4- is replaced using D1, 3,5- triazines are synthesized by identical method in addition to this and have manufactured compound 16.
MS[M+H]+=719.82
The synthesis of compound 17
[reaction equation 4-17]
In the synthesis of above compound 1, C1 is replaced using C7, uses 2- ([1.1 '-xenyl] -4- base) -4- (3- chlorine Phenyl) -6- phenyl -1,3,5-triazines is instead of 2- ([1,1 '-xenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines, except this In addition, it is synthesized by identical method and has manufactured compound 17.
MS[M+H]+=744.87
The synthesis of compound 18
[reaction equation 4-18]
In the synthesis of above compound 1, C1 is replaced using B4, uses 2,4- diphenyl -6- (3- (4,4,5,5- tetramethyls Penta ring -2- base of base -1,3,2- dioxy boron) phenyl) -1,3,5- triazine replace 2- ([1,1 '-xenyl] -4- base) chloro- 6- benzene of -4- Base -1,3,5-triazines is synthesized by identical method in addition to this and has manufactured compound 18.
MS[M+H]+=900.03
The synthesis of compound 19
[reaction equation 4-19]
In the synthesis of above compound 1, C1 is replaced using B3, uses 2,4- diphenyl -6- (4- (4,4,5,5- tetramethyls Penta ring -2- base of base -1,3,2- dioxy boron) phenyl) -1,3,5- triazine replace 2- ([1,1 '-xenyl] -4- base) chloro- 6- benzene of -4- Base -1,3,5-triazines is synthesized by identical method in addition to this and has manufactured compound 19.
MS[M+H]+=900.03
The synthesis of compound 20
[reaction equation 4-20]
In the synthesis of above compound 1, C1 is replaced using C2, replaces 2- ([1,1 '-xenyl] -4- base)-using D2 4- chloro-6-phenyl -1,3,5-triazines is synthesized by identical method in addition to this and has manufactured compound 20.
MS[M+H]+=708.83
The synthesis of compound 21
[reaction equation 4-21]
In the synthesis of above compound 1, C1 is replaced using C2, uses 4- ([1,1 '-xenyl] -4- base) -2- chloroquine Oxazoline replaces 2- ([1,1 '-xenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines to pass through identical method in addition to this It synthesizes and has manufactured compound 21.
MS[M+H]+=565.64
Embodiment 1
It will be withThickness thin film be coated with the glass substrate of ITO (tin indium oxide (indium tin oxide)) (healthy and free from worry 7059 glass) is put into the distilled water dissolved with dispersing agent, utilizes ultrasonic washing.As detergent, Fei Xier has been used The product of company (Fischer Co.) has used as distilled water and has utilized Millipore Corp. (Millipore Co.) manufacture Distilled water after filter (Filter) filtering 2 times.By ITO wash 30 minutes after, using distilled water repeatedly 2 times and carry out 10 points Clock ultrasonic washing.After distilling water washing, ultrasonic washing is carried out with the solvent sequence of isopropanol, acetone, methanol and is done It is dry.
On the ito transparent electrode prepared in this way withThickness thermal vacuum be deposited six nitriles, six azepine benzophenanthrene (hexanitrile hexaazatriphenylene, HI-1) and form hole injection layer.The vacuum on above-mentioned hole injection layer The HT1 of the substance as transporting holes is depositedAfterwards, then on above-mentioned hole transmission layer withFilm thickness it is true Sky is deposited HT2 and forms hole regulating course.As compound light-emitting layer, by material of main part BH1 and dopant material BD1 chemical combination Object (25:1) withThickness vacuum evaporation.Then, ETM1 compound is formedAs electrical adjustment layer, it is used in system Make the compound 1 synthesized in example 4 and LiQ (1:1,) carry out total vapor deposition and sequentially form electron transfer layer.In above-mentioned electricity Successively will in sub- transport layerThe lithium fluoride (LiF) of thickness, Mg and Ag (10:1,) be deposited, it is deposited The aluminium of thickness and form cathode, to manufacture organic illuminating element.
In above process, the evaporation rate of organic matter maintainsLithium fluoride maintainsVapor deposition speed Degree, aluminium maintain 3 toEvaporation rate.
Embodiment 2 to 11 and comparative example 1 to 4
In above-described embodiment 1, as electron transfer layer, compound 1, electronics are replaced using compound recorded in table 1 Transport layer and the ratio of LiQ use ratio recorded in table 1, in addition to this, manufacture organic illuminating element by identical method.
Test example 1: the performance evaluation of organic illuminating element
Apply electric current (20mA/cm to the organic illuminating element made in above-described embodiment 2 to 11 and comparative example 1 to 42) When, measurement voltage, efficiency, brightness, chromaticity coordinates and service life, it the results are shown in following table 2.
[table 1]
Embodiment 12
It will be withThickness thin film be coated with the glass substrate of ITO (tin indium oxide (indium tin oxide)) (healthy and free from worry 7059 glass) is put into the distilled water dissolved with dispersing agent, utilizes ultrasonic washing.As detergent, Fei Xier has been used The product of company (Fischer Co.) has used as distilled water and has utilized Millipore Corp. (Millipore Co.) manufacture Distilled water after filter (Filter) filtering 2 times.By ITO wash 30 minutes after, using distilled water repeatedly 2 times and carry out 10 points Clock ultrasonic washing.After distilling water washing, ultrasonic washing is carried out with the solvent sequence of isopropanol, acetone, methanol and is done It is dry.
On the ito transparent electrode prepared in this way withThickness thermal vacuum be deposited six nitriles, six azepine benzophenanthrene (hexanitrile hexaazatriphenylene, HI-1) and form hole injection layer.The vacuum on above-mentioned hole injection layer The HT1 of the substance as transporting holes is depositedAfterwards, then on above-mentioned hole transmission layer withFilm thickness it is true Sky is deposited HT2 and forms hole regulating course.As compound light-emitting layer, by material of main part BH1 and dopant material BD1 chemical combination Object (25:1) withThickness vacuum evaporation.Then, the compound 1 that will be synthesized in Production Example 4Be formed as electricity Sub- regulating course, with ETM2 and LiQ (1:1,) carry out total vapor deposition and sequentially form electron transfer layer.In above-mentioned electron-transport Successively will on layerThe lithium fluoride (LiF) of thickness, Mg and Ag (10:1,) be deposited, it is depositedThickness Aluminium and form cathode, to manufacture organic illuminating element.
In above process, the evaporation rate of organic matter maintainsLithium fluoride maintainsVapor deposition speed Degree, aluminium maintain 3 toEvaporation rate.
Embodiment 13 to 29 and comparative example 5 to 8
In above-described embodiment 12, as electrical adjustment layer, ETM 1 is replaced using the compound recorded in table 2, electronics passes The ratio of defeated layer and LiQ are using the ratio recorded in table 2, in addition to this, manufacture organic illuminating element by identical method.
Test example 2: the performance evaluation of organic illuminating element
Apply electric current (20mA/ to the organic illuminating element made in above-described embodiment 13 to 29 and comparative example 5 to 8 cm2) when, measurement voltage, efficiency, brightness, chromaticity coordinates and service life, it the results are shown in following table 2.
[table 2]
As shown in above-mentioned Tables 1 and 2, the compound derivatives of chemical formula according to the present invention are being with organic illuminating element It can play the role of electron-transport and electrical adjustment in the organic electronic element of representative, element according to the present invention is in efficiency, drive Excellent characteristic is shown in terms of dynamic voltage, stability, life characteristic.
In the case where the compound used as comparative example, it can be confirmed compared with the compound of the present application, the longevity Ordering characteristic significantly reduces.

Claims (12)

1. a kind of compound indicated by following chemical formula 1:
Chemical formula 1
In the chemical formula 1,
X1And X2It is each independently O or S,
L1Direct Bonding, substituted or unsubstituted C are each independently in recurring unit6-60Arlydene or include N, O and S In more than one substituted or unsubstituted C5-60Heteroarylidene,
R1To R3It is each independently hydrogen, deuterium, halogen group, cyano, three (C1-60Alkyl) it is silicyl, substituted or unsubstituted C1-60Alkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C1-60It is alkylthio, substituted or unsubstituted C3-60Naphthenic base, substituted or unsubstituted C6-60Aryl or comprising more than one substituted or unsubstituted in N, O and S C5-60Heteroaryl,
R4It is each independently comprising the more than one substituted or unsubstituted C in N, O and S5-60Heteroaryl is replaced by cyano C6-60Aryl or three (C6-60Aryl) silicyl,
n1、n20 to 4 integer is each independently with m,
The integer that p is 0 to 4,
The integer that q is 1 to 4,
Wherein, 1≤p+q≤4,
When p and q are respectively 2 or more, the structure in 2 or more brackets is same or different to each other.
2. compound according to claim 1, wherein the compound indicated by the chemical formula 1 is selected from by followingization Any of the compound that formula 1-1 and 1-2 are indicated:
Chemical formula 1-1
Chemical formula 1-2
In the chemical formula 1-1 and 1-2,
X1、X2、L1、R1、R2、R3、R4、n1、n2It is identical as the definition in claim 1 with m.
3. compound according to claim 1, wherein X1And X2For O.
4. compound according to claim 1, wherein L1For Direct Bonding or selected from any of following radicals:
5. compound according to claim 1, wherein R1For hydrogen.
6. compound according to claim 1, wherein R2For hydrogen.
7. compound according to claim 1, wherein R3For hydrogen.
8. compound according to claim 1, wherein R4For in the compound indicated by following chemical formula 2 to 10 Any one:
Chemical formula 2
Chemical formula 3
Chemical formula 4
Chemical formula 5
Chemical formula 6
Chemical formula 7
Chemical formula 8
Chemical formula 9
Chemical formula 10
In the chemical formula 2 to 6,
G1To G30In include either one or two of in each chemical formula for the L with chemical formula 11The position of bonding,
In addition to the L with chemical formula 11Remaining G except the position of bonding1To G30It is each independently hydrogen, deuterium, itrile group, nitro, hydroxyl Base, carbonyl, ester group, imide, amide groups, substituted or unsubstituted C1-60Alkyl, substituted or unsubstituted C3-60Naphthenic base, Substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C6-60Aryloxy group, substituted or unsubstituted C1-60Alkyl sulfenyl, Substituted or unsubstituted C6-60Artyl sulfo, substituted or unsubstituted C2-60Alkenyl, substituted or unsubstituted C1-60Alkylsilyl groups Base, substituted or unsubstituted C1-60Alkyl boryl, substituted or unsubstituted C1-60Alkyl amine group, substituted or unsubstituted C6-60Virtue Base includes the more than one substituted or unsubstituted C in N, O and S5-60Heteroaryl,
In the chemical formula 7,
X1' to X3' it is each independently N or CR1',
G31To G33And R1' any of be L with chemical formula 11The position of bonding,
In addition to the L with chemical formula 11Remaining G other than the position of bonding31To G33And R1' it is each independently hydrogen, deuterium, itrile group, nitre Base, hydroxyl, carbonyl, ester group, imide, amide groups, substituted or unsubstituted C1-60Alkyl, substituted or unsubstituted C3-60Ring Alkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C6-60Aryloxy group, substituted or unsubstituted C1-60Alkyl Sulfenyl, substituted or unsubstituted C6-60Artyl sulfo, substituted or unsubstituted C2-60Alkenyl, substituted or unsubstituted C1-60Alkyl Silicyl, substituted or unsubstituted C1-60Alkyl boryl, substituted or unsubstituted C1-60It is alkyl amine group, substituted or unsubstituted C6-60Aryl includes the more than one substituted or unsubstituted C in N, O and S5-60Heteroaryl, wherein X1' to X3' it is all CR1’ When, R1' it is itrile group,
In the chemical formula 8,
X4' to X7' it is each independently N or CR2', wherein X4' to X7' at least one be N,
G34To G39And R2' any of for L with chemical formula 11The position of bonding,
In addition to the L with chemical formula 11Remaining G except the position of bonding34To G39And R2' it is each independently hydrogen, deuterium, itrile group, nitre Base, hydroxyl, carbonyl, ester group, imide, amide groups, substituted or unsubstituted C1-60Alkyl, substituted or unsubstituted C3-60Ring Alkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C6-60Aryloxy group, substituted or unsubstituted C1-60Alkyl Sulfenyl, substituted or unsubstituted C6-60Artyl sulfo, substituted or unsubstituted C2-60Alkenyl, substituted or unsubstituted C1-60Alkyl Silicyl, substituted or unsubstituted C1-60Alkyl boryl, substituted or unsubstituted C1-60It is alkyl amine group, substituted or unsubstituted C6-60Aryl includes the more than one substituted or unsubstituted C in N, O and S5-60Heteroaryl,
In the chemical formula 9,
Y1' it is O, S, NR3' or CR4’R5',
G40To G44And R3' to R5' any of be L with chemical formula 11The position of bonding,
In addition to the L with chemical formula 11Remaining G except the position of bonding40To G44And R3' to R5' it is each independently hydrogen, deuterium, nitrile Base, nitro, hydroxyl, carbonyl, ester group, imide, amide groups, substituted or unsubstituted C1-60It is alkyl, substituted or unsubstituted C3-60Naphthenic base, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C6-60It is aryloxy group, substituted or unsubstituted C1-60Alkyl sulfenyl, substituted or unsubstituted C6-60Artyl sulfo, substituted or unsubstituted C2-60It is alkenyl, substituted or unsubstituted C1-60AIkylsilyl groups, substituted or unsubstituted C1-60Alkyl boryl, substituted or unsubstituted C1-60Alkyl amine group, substitution or Unsubstituted C6-60Aryl includes the more than one substituted or unsubstituted C in N, O and S5-60Heteroaryl, adjacent group can Substituted or unsubstituted ring is formed to be bonded to each other,
In the chemical formula 10,
Y2' it is O, S, NR6' or CR7’R8',
X8' and X9' it is each independently N or CR9',
G45、G46And R6' to R9' any of for L with chemical formula 11The position of bonding,
In addition to the L with chemical formula 11Remaining G except the position of bonding45、G46And R6' to R9' it is each independently hydrogen, deuterium, nitrile Base, nitro, hydroxyl, carbonyl, ester group, imide, amide groups, substituted or unsubstituted C1-60It is alkyl, substituted or unsubstituted C3-60Naphthenic base, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C6-60It is aryloxy group, substituted or unsubstituted C1-60Alkyl sulfenyl, substituted or unsubstituted C6-60Artyl sulfo, substituted or unsubstituted C2-60It is alkenyl, substituted or unsubstituted C1-60AIkylsilyl groups, substituted or unsubstituted C1-60Alkyl boryl, substituted or unsubstituted C1-60Alkyl amine group, substitution or Unsubstituted C6-60Aryl includes the more than one substituted or unsubstituted C in N, O and S5-60Heteroaryl.
9. compound according to claim 1, wherein R4For selected from by any of following radicals:
In above-mentioned group,
R5It is each independently hydrogen, substituted or unsubstituted C6-60Aryl or comprising in N, O and S more than one substitution or Unsubstituted C5-60Heteroaryl.
10. compound according to claim 1, wherein the compound indicated by the chemical formula 1 is selected from following radicals Any of:
11. a kind of organic illuminating element comprising: first electrode, it is opposed with the first electrode and have second electricity Pole and has one layer or more of organic matter layer between the first electrode and the second electrode, the organic matter layer In one layer or more include compound described in any one of claims 1 to 10.
12. organic illuminating element according to claim 11, which is characterized in that the organic matter layer comprising the compound is Electron injecting layer, electron transfer layer or the layer for carrying out electron injection and electron-transport simultaneously.
CN201811228645.5A 2017-11-24 2018-10-22 Novel heterocyclic compound and organic light-emitting element using same Active CN109836419B9 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020170158930A KR102174391B1 (en) 2017-11-24 2017-11-24 Novel hetero-cyclic compound and organic light emitting device comprising the same
KR10-2017-0158930 2017-11-24

Publications (3)

Publication Number Publication Date
CN109836419A true CN109836419A (en) 2019-06-04
CN109836419B CN109836419B (en) 2022-07-01
CN109836419B9 CN109836419B9 (en) 2022-08-05

Family

ID=66849392

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201811228645.5A Active CN109836419B9 (en) 2017-11-24 2018-10-22 Novel heterocyclic compound and organic light-emitting element using same

Country Status (2)

Country Link
KR (1) KR102174391B1 (en)
CN (1) CN109836419B9 (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021033731A1 (en) * 2019-08-19 2021-02-25 出光興産株式会社 Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device
CN112538056A (en) * 2019-09-20 2021-03-23 南京高光半导体材料有限公司 Electron transport material and organic electroluminescent device containing same
CN113874366A (en) * 2019-09-11 2021-12-31 株式会社Lg化学 Heterocyclic compound and organic light emitting device including the same
CN113950474A (en) * 2019-11-05 2022-01-18 Lt素材株式会社 Heterocyclic compound and organic light-emitting device including same

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106397485A (en) * 2015-07-31 2017-02-15 三星显示有限公司 Condensed cyclic compound and organic light-emitting device including the same

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101497133B1 (en) 2011-12-23 2015-02-27 제일모직 주식회사 Compound for organic OPTOELECTRONIC device, ORGANIC LIGHT EMITTING DIODE INCLUDING THE SAME and DISPLAY INCLUDING THE organic LIGHT EMITTING DIODE
KR101666825B1 (en) * 2014-03-11 2016-10-18 (주)피엔에이치테크 Novel compound for organic electroluminescent device and organic electroluminescent device comprising the same
KR20180007042A (en) * 2016-07-11 2018-01-22 삼성디스플레이 주식회사 Condensed compound and organic light emitting diode comprising the same
KR101801003B1 (en) * 2016-08-23 2017-11-24 주식회사 두산 Organic compounds and organic electro luminescence device comprising the same

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106397485A (en) * 2015-07-31 2017-02-15 三星显示有限公司 Condensed cyclic compound and organic light-emitting device including the same

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
MORRISON, BRIAN J.等: "Thiones as Reactive Intermediates in Condensations of Thiones as Reactive Intermediates in Condensations of Decasulfide", 《PHOSPHORUS, SULFUR AND SILICON AND THE RELATED ELEMENTS》 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021033731A1 (en) * 2019-08-19 2021-02-25 出光興産株式会社 Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device
CN113874366A (en) * 2019-09-11 2021-12-31 株式会社Lg化学 Heterocyclic compound and organic light emitting device including the same
CN113874366B (en) * 2019-09-11 2024-04-26 株式会社Lg化学 Heterocyclic compound and organic light-emitting device comprising same
CN112538056A (en) * 2019-09-20 2021-03-23 南京高光半导体材料有限公司 Electron transport material and organic electroluminescent device containing same
CN112538056B (en) * 2019-09-20 2022-06-28 南京高光半导体材料有限公司 Electron transport material and organic electroluminescent device containing same
CN113950474A (en) * 2019-11-05 2022-01-18 Lt素材株式会社 Heterocyclic compound and organic light-emitting device including same

Also Published As

Publication number Publication date
KR102174391B1 (en) 2020-11-04
CN109836419B9 (en) 2022-08-05
KR20190060585A (en) 2019-06-03
CN109836419B (en) 2022-07-01

Similar Documents

Publication Publication Date Title
CN107840835B (en) Novel heterocyclic compound and organic light-emitting element using same
CN109564972A (en) Organic illuminating element
KR101837896B1 (en) Compound and organic electronic device comprising the same
KR20180063710A (en) An electroluminescent compound and an electroluminescent device comprising the same
CN105431423A (en) Heterocyclic compound and organic light-emitting device comprising same
CN107619410A (en) Compound and the organic electronic element for including it
CN109836419A (en) Novel heterocyclic compounds and the organic illuminating element for utilizing it
CN109476597A (en) New compound and the organic illuminating element for utilizing it
CN107759638A (en) New organo-metallic compound and utilize its organic illuminating element
CN108884086A (en) Novel heterocyclic compounds and the organic illuminating element for utilizing it
CN107614493A (en) Spiro-compound and the organic luminescent device for including it
CN110088110A (en) New compound and organic illuminating element comprising it
CN110099902A (en) New compound and organic illuminating element comprising it
CN110536887A (en) New compound and organic luminescent device comprising it
KR20170041134A (en) Amine compound and organic light emitting device comprising the same
KR102142676B1 (en) Novel compound and organic light emitting device comprising the same
CN110248922A (en) Novel phenanthrene compound and the organic illuminating element for utilizing it
TWI607997B (en) Novel naphthotriazole derivatives and organic electroluminescent devices
CN110494430A (en) New compound and the organic illuminating element for utilizing it
KR102103506B1 (en) Novel hetero-cyclic compound and organic light emitting device comprising the same
CN108884105A (en) Novel heterocyclic compound and the organic illuminating element using it
CN110520427A (en) Novel heterocyclic compounds and the organic illuminating element for utilizing it
CN108239078A (en) Novel heterocyclic compounds and utilize its organic illuminating element
CN108864124A (en) Cyclic compound and organic illuminating element comprising it
KR102258617B1 (en) Novel hetero-cyclic compound and organic light emitting device comprising the same

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
CI03 Correction of invention patent

Correction item: Description

Correct: Instructions submitted on December 30, 2021

False: Instructions submitted on October 22, 2018

Number: 26-02

Page: ??

Volume: 38

CI03 Correction of invention patent