CN106573912A - Triazine compound, method for producing same, and application for same - Google Patents

Triazine compound, method for producing same, and application for same Download PDF

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CN106573912A
CN106573912A CN201580043586.2A CN201580043586A CN106573912A CN 106573912 A CN106573912 A CN 106573912A CN 201580043586 A CN201580043586 A CN 201580043586A CN 106573912 A CN106573912 A CN 106573912A
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bases
phenyl
pyridine radicals
base
carbon number
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新井信道
服部希
服部一希
冈祐儿
野村桂甫
田中刚
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Tosoh Corp
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Tosoh Corp
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms

Abstract

Provided is an electron transport material having excellent heat resistance, long service life in an organic electroluminescent element, and excellent low-voltage drive properties or luminous efficiency. A material for an organic electroluminescent element, represented by general formula (1). (In general formula (1), Ar1, Ar2, Ar3, R5, R6, R7, n, p, q, r, Z1, and Z2 have the meanings described in claim 1.)

Description

Triaizine compounds, its manufacture method, and application thereof
Technical field
The present invention relates to triaizine compounds and its manufacture method and the unit of the organic electroluminescent containing the triaizine compounds Part.More specifically, be related to using in triazine skeleton combine have diaryl pyrazole piperidinyl structure be characterized, as organic electroluminescence Light-emitting element material and useful triaizine compounds and its manufacture method, and be related to be used for the triaizine compounds to organise The organic electroluminescent device of high efficiency, low-voltage and high-durability that at least one of which of compound layer is characterized.
Background technology
Organic electroluminescent device with using hole transmission layer and electron transfer layer clamping the luminescent layer containing luminescent material, And the structure of anode and negative electrode is installed on the outside of it as basic structure, be using with the hole by injection luminescent layer and Electronics in conjunction with and the light-emitting component of light (fluorescence or phosphorescence) that the exciton that produces is released when inactivating, be not only applied to little The display of type, is also applied to the purposes such as large-scale tv machine, illumination.It should be noted that sometimes also by above-mentioned hole transport Layer is divided into hole transmission layer and hole injection layer, above-mentioned luminescent layer is divided into into electronic barrier layer and luminescent layer and hole barrier Layer, above-mentioned electron transfer layer is divided into into electron transfer layer and electron injecting layer and is constituted.In addition, as organic electroluminescent unit The carrier blocking layers (electron transfer layer or hole transmission layer) of part, also use doped with metal, organo-metallic compound sometimes Or the common evaporation film of other organic compounds.
Compared with inorganic light-emitting diode, driving voltage is high, luminosity and luminous for traditional organic electroluminescent device Efficiency is low, component life is also significant lower, not yet reaches practical level.And nearest organic electroluminescent device although by Gradually improved, but still required that more excellent material in terms of light-emitting efficiency characteristics, driving voltage characteristic, long-life characteristics Material.Additionally, in the purposes such as vehicle-mounted purposes, also sometimes for high-fire resistance, it is desirable to which material has high glass-transition temperature (Tg)。
As the electron transport material that the long-life property for organic electroluminescent device is excellent, patent document can be set forth in Triaizine compounds disclosed in 1.However, having used the organic electroluminescent device of the material in voltage, life-span and luminous efficiency Aspect requires further improvement.
Patent Document 2 discloses triaizine compounds for representing with compound 4-12 etc..These compounds are in organic electroluminescence The high-luminous-efficiencyization aspect of light-emitting component is excellent, but requires the further improvement of luminous efficiency.
Prior art literature
Patent document
Patent document 1：Japanese Patent Publication 2011-063584 publication
Patent document 2：Korean Patent Publication 10-2013-0128322 publication
The content of the invention
Problems to be solved by the invention
It is an object of the invention to provide the long-life property of the excellent heat resistance of film quality, organic electroluminescent device, low electricity The excellent electron transport material of pressure driven nature or luminous efficiency.
The method of solve problem
The present inventor etc. have made intensive studies to solve above-mentioned problem, as a result find, are bonded with described later two fragrant The heat resistance of the film quality of the triaizine compounds of yl pyridines base is high, sent out using the compound as the organic electroluminescence of electron transport material Optical element can realize lower voltage, long lifetime or high-luminous-efficiency compared with the situation using known material Change, and then complete the present invention.
That is, the present invention relates to following [1]～[17].
[1] triaizine compounds shown in formula (1) described later.
[2] triaizine compounds described in above-mentioned [1], wherein, Ar2And Ar3It is each independently and optionally link and/or condensed ring Carbon number 6～24 aromatic hydrocarbyl, be only made up of 6 yuan of rings and optionally link and/or condensed ring carbon number 3～25 Nitrogenous heteroaromatic group links by the atomic building in the atom group constituted selected from H, C, O and S and optionally and/or condensed ring Carbon number 3～25 heteroaromatic group.
[3] triaizine compounds described in above-mentioned [1], wherein, Ar2And Ar3It is each independently phenyl, xenyl, naphthyl benzene Base, phenanthryl phenyl, fluoranthene base phenyl, pyridinylphenyl, quinolyl phenyl, thienyl phenyl, furyl phenyl, benzothienyl Phenyl, benzofuranyl phenyl, dibenzothiophenes base phenyl, dibenzofuran group phenyl, naphthyl, pyridine radicals, benzothienyl, (these groups are optionally taken by fluorine atom or methyl for benzofuranyl, phenanthryl, anthryl, dibenzothiophenes base or dibenzofuran group Generation).
[4] triaizine compounds described in above-mentioned [1], wherein, Ar2And Ar3It is each independently phenyl, tolyl, dimethyl Phenyl, xenyl, naphthylphenyl, phenanthryl phenyl, pyridinylphenyl, dibenzothiophenes base phenyl, dibenzofuran group phenyl, naphthalene Base, pyridine radicals, benzothienyl, benzofuranyl, phenanthryl, anthryl, dibenzothiophenes base or dibenzofuran group.
[5] triaizine compounds described in above-mentioned [1], wherein, Ar1(these groups are appointed to be each independently phenyl or naphthyl Choosing is replaced by methyl or phenyl).
[6] triaizine compounds described in above-mentioned [1], wherein, Ar1It is each independently phenyl, naphthyl or xenyl.
[7] triaizine compounds described in above-mentioned [1], wherein, Ar1For phenyl.
[8] triaizine compounds described in above-mentioned [1], wherein, p=q=r=0.
The manufacture method of the triaizine compounds described in [9] above-mentioned [1], it includes：Make the change shown in formula described later (12) Compound shown in compound and formula described later (13) in presence of a base or does not exist in the presence of palladium catalyst Under conditions of alkali, coupling reaction is sequentially or simultaneously carried out.
The manufacture method of the triaizine compounds described in [10] above-mentioned [1], it includes：Make the change shown in formula described later (14) Compound shown in compound and formula described later (15) in presence of a base or does not exist in the presence of palladium catalyst Coupling reaction is carried out under conditions of alkali.
The manufacture method of the triaizine compounds described in [11] above-mentioned [1], it includes：Make the change shown in formula described later (22) Compound shown in compound and formula described later (23) sequentially or simultaneously carries out coupling reaction in the presence of palladium catalyst.
The manufacture method of the triaizine compounds described in [12] above-mentioned [1], it includes：Make the change shown in formula described later (24) Compound shown in compound and formula described later (25) sequentially or simultaneously carries out coupling reaction in the presence of palladium catalyst.
The manufacture method of the triaizine compounds described in [13] above-mentioned [1], it includes：Make in the presence of palladium catalyst aftermentioned Formula (26), formula described later (28) and the compound shown in formula described later (30) carry out coupling reaction.
The manufacture method of the triaizine compounds described in [14] above-mentioned [1], it includes：Make in the presence of palladium catalyst aftermentioned Formula (33), formula described later (22) and the compound shown in formula described later (30) carry out coupling reaction.
[15] pyridine compounds described in above-mentioned [13], it is the compound shown in formula described later (26).
[16] material for organic electroluminescence device, it includes the triaizine compounds described in [1].
[17] organic electroluminescent device electron transport material, it includes the triaizine compounds described in [1].
That is, the present invention relates to triaizine compounds (hereinafter also referred to triaizine compounds (1)) shown in following formulas (1), its Manufacture method and the material for organic electroluminescence device using it.
[chemical formula 1]
(in formula (1),
Ar1Represent phenyl or naphthyl independently of one another (these groups are optionally replaced by fluorine atom, methyl or phenyl).
Ar2And Ar3Represent independently of one another optionally link and/or condensed ring carbon number 6～24 aromatic hydrocarbyl, only Be made up of 6 yuan of rings and optionally linked and/or condensed ring carbon number 3～25 nitrogenous heteroaromatic group or by selected from H, C, O And heteroaromatic group (this of the carbon number 3～25 of the atomic building in the atom group of S compositions and optional link and/or condensed ring A little groups are optionally replaced by the alkoxyl of fluorine atom, the alkyl of carbon number 1～4 or carbon number 1～4).
R5、R6And R7The alkyl of carbon number 1～4 is represented independently of one another.
N represents 0 or 1.
P represents 0,1,2,3 or 4.In the case that p is 2,3 or 4, R5Can be with different from each other.
Q represents 0,1,2,3 or 4.In the case that q is 2,3 or 4, R6Can be with different from each other.
R represents 0,1 or 2.In the case that r is 2,2 R7Can be with different from each other.
Z1And Z2Nitrogen-atoms or C-H are represented independently of one another.Also, Z1Or Z2In any one represent nitrogen-atoms, another Person represents C-H.).
According to the present invention, it is possible to provide the triaizine compounds of the excellent heat resistance of film quality, and low-voltage, long-life can be provided Or the organic electroluminescent device that luminous efficiency is excellent.
Hereinafter, the present invention is described in detail.
The present invention relates to above-mentioned triaizine compounds (1), their manufacture method and the Organic Electricity comprising the compound Electroluminescent element material.
Substituent in the triaizine compounds (1) of the present invention is defined respectively as.
In formula (1), Ar1Represent that (these groups are optionally by fluorine atom, methyl or phenyl for phenyl or naphthyl independently of one another Replace).
As Ar1In the phenyl or naphthyl being replaced by fluorine atoms, be not particularly limited, but as preference, can enumerate： Fluorophenyl, pentafluorophenyl group, difluorophenyl, fluoronaphthalene base or difluoro naphthyl etc..
As Ar1In by methyl substituted phenyl or naphthyl, be not particularly limited, but as preference, can enumerate：First Phenyl, methyl naphthyl, 3,5-dimethylphenyl or dimethyl naphthyl etc..
As Ar1In the phenyl or naphthyl being substituted by phenyl, be not particularly limited, but as preference, can enumerate：Connection Phenyl, phenyl napthyl, terphenyl or diphenyl naphthyl etc..
From electron transporting material excellent aspect, more preferably Ar1Be each independently phenyl, naphthyl or Xenyl, from the easy angle of synthesis, more preferably phenyl.
As Ar1Concrete example, be not particularly limited, but as preference, can enumerate：Phenyl, p-methylphenyl, a toluene Base, o-tolyl, 2,4- 3,5-dimethylphenyls, 3,5- 3,5-dimethylphenyls,Base, 2- fluorophenyls, 3- fluorophenyls, 4- fluorophenyls, 2, 4- difluorophenyls, 3,5- difluorophenyls, biphenyl -2- bases, biphenyl -3- bases, biphenyl -4- bases, 3- methyl biphenyl -4- bases, 2 '-methyl Biphenyl -4- bases, 4 '-methyl biphenyl -4- bases, 2,2 '-dimethyl diphenyl -4- bases, 2 ', 4 ', 6 '-trimethylbiphenyl -4- bases, 6- first Base biphenyl -3- bases, 5- methyl biphenyl -3- bases, 2 '-methyl biphenyl -3- bases, 4 '-methyl biphenyl -3- bases, 6,2 '-dimethyl connection Benzene -3- bases, 2 ', 4 ', 6 '-trimethylbiphenyl -3- bases, 5- methyl biphenyl -2- bases, 6- methyl biphenyl -2- bases, 2 '-methyl biphenyl - 2- bases, 4 '-methyl biphenyl -2- bases, 6,2 '-dimethyl diphenyl -2- bases, 2 ', 4 ', 6 '-trimethylbiphenyl -2- bases, 1- naphthyls, 2- Naphthyl, 1- phenylnaphthalene -2- bases, 1- phenylnaphthalene -3- bases, 1- phenylnaphthalene -4- bases, 1- phenylnaphthalene -5- bases, 1- phenylnaphthalene -6- bases, 1- Phenylnaphthalene -7- bases, 1- phenylnaphthalene -8- bases, 2- phenylnaphthalene -1- bases, 2- phenylnaphthalene -3- bases, 2- phenylnaphthalene -4- bases, 2- phenylnaphthalenes - 5- bases, 2- phenylnaphthalene -6- bases, 2- phenylnaphthalene -7- bases, 2- phenylnaphthalene -8- bases, 1- methyl naphthalene -4- bases, 1- methyl naphthalene -5- bases, 1- Methyl naphthalene -6- bases, 1- methyl naphthalene -7- bases, 1- methyl naphthalene -8- bases, 2- methyl naphthalene -1- bases, 2- methyl naphthalene -3- bases, 2- methyl naphthalenes - 4- bases, 2- methyl naphthalene -5- bases, 2- methyl naphthalene -6- bases, 2- methyl naphthalene -7- bases or 2- methyl naphthalene -8- bases etc..These substituents In, from electron transporting material excellent aspect, preferred phenyl, p-methylphenyl, biphenyl -3- bases, biphenyl -4- bases, 1- naphthyls or 2- naphthyls, more preferably phenyl, biphenyl -3- bases, biphenyl -4- bases, 1- naphthyls or 2- naphthyls.
In formula (1), Z1And Z2In any one represent that nitrogen-atoms, another one represent C-H.
In formula (1), Ar2And Ar3The fragrance of the optionally carbon number 6～24 of link and/or condensed ring is represented independently of one another Race's alkyl, be only made up of 6 yuan of rings and optionally link and/or condensed ring carbon number 3～25 nitrogenous heteroaromatic group or by selecting The heteroaryl of atomic building and the carbon number 3～25 of optional link and/or condensed ring in the atom group of free H, C, O and S composition Race's group (these groups are optionally replaced by the alkoxyl of fluorine atom, the alkyl of carbon number 1～4 or carbon number 1～4).
In formula (1), Ar2And Ar3Can be with identical, it is also possible to different.
As Ar2And Ar3In, optionally link and/or condensed ring carbon number 6～24 aromatic hydrocarbyl, it is not special Limit, but as preference, can enumerate：Phenyl, xenyl, terphenyl, tetrad phenyl, naphthylphenyl, phenanthryl phenyl, anthryl Phenyl, pyrenyl phenyl, triphenyl phenyl,Base phenyl, fluoranthene base phenyl, acenaphthenyl phenyl, fluorenyl phenyl, naphthyl xenyl, naphthalene Base, phenyl napthyl, biphenyl naphthyl, phenanthryl naphthyl, anthryl naphthyl, phenanthryl, phenyl phenanthryl, naphthyl phenanthryl, anthryl, phenyl anthryl, Naphthyl anthryl, pyrenyl, phenyl pyrenyl, benzo phenanthryl, phenyl benzo phenanthryl,Base, phenylBase, fluoranthene base, phenyl fluoranthene Base, acenaphthenyl, phenyl acenaphthenyl, fluorenyl, phenylfluorenyl or benzo fluorenyl etc..These substituents are optionally by fluorine atom, carbon number 1 ～4 alkyl or the alkoxyl of carbon number 1～4 replace.
As Ar2And Ar3In, be only made up of 6 yuan of rings and optionally link and/or condensed ring carbon number 3～25 it is nitrogenous Heteroaromatic group, is not particularly limited, but as preference, can enumerate：Pyridine radicals, pyrazinyl, pyrimidine radicals, pyridazinyl, triazine Base, quinolyl, isoquinolyl, phenanthridinyl, benzoquinoline base, acridinyl, pyridinylphenyl, pyrazinylphenyl, pyrimidine radicals phenyl, Pyridazinyl phenyl, triazine radical phenyl, quinolyl phenyl, isoquinolyl phenyl, phenanthridinyl phenyl, benzoquinoline base phenyl, acridine Base phenyl, (phenylpyridyl) phenyl, (naphthlypyridine base) phenyl, pyridine radicals xenyl, pyrazinyl xenyl, pyrimidine radicals biphenyl Base, pyridazinyl xenyl, triazine radical xenyl, quinolyl xenyl, isoquinolyl xenyl, phenanthridinyl xenyl, benzo quinoline Quinoline base xenyl, acridinyl xenyl, pyridine radicals terphenyl, pyrazinyl terphenyl, pyrimidine radicals terphenyl, pyridazinyl three Xenyl, triazine radical terphenyl, pyridine radicals naphthyl, pyrazinyl naphthyl, pyrimidine radicals naphthyl, pyridazinyl naphthyl, triazine radical naphthyl, Quinolyl naphthyl, isoquinolyl naphthyl, phenanthridinyl naphthyl, benzoquinoline base naphthyl, acridinyl naphthyl, phenylpyridyl, biphenyl Pyridine radicals, naphthlypyridine base, phenanthryl pyridine radicals, anthryl pyridine radicals, pyrenyl pyridine radicals, benzophenanthrene yl pyridines base,Yl pyridines base, Fluoranthene yl pyridines base, acenaphthenyl pyridine radicals or fluorenyl pyridine radicals etc..These substituents are optionally by fluorine atom, carbon number 1～4 The alkoxyl of alkyl or carbon number 1～4 replaces.
As Ar2And Ar3In, by the atomic building in the atom group constituted selected from H, C, O and S and optionally link and/ Or the heteroaromatic group of the carbon number 3～25 of condensed ring, it is not particularly limited, but as preference, can enumerate：Thienyl, furan Mutter base, bithiophene base, connection furyl, benzothienyl, benzofuranyl, dibenzothiophenes base, dibenzofuran group, thienyl Phenyl, furyl phenyl, bithiophene base phenyl, connection furyl phenyl, benzothienyl phenyl, benzofuranyl phenyl, hexichol Bithiophene base phenyl, dibenzofuran group phenyl, thienyl xenyl, furyl xenyl, benzothienyl xenyl, benzo Furyl xenyl, dibenzothiophenes base xenyl, dibenzofuran group xenyl, thienyl naphthyl, furyl naphthyl, benzo Thienyl naphthyl, benzofuranyl naphthyl, dibenzothiophenes base naphthyl, dibenzofuran group naphthyl, tolylthiophene base, phenyl furan Mutter base, biphenyl thienyl, biphenyl furyl, naphthyl thienyl, naphthyl furyl, phenanthryl thienyl, phenanthryl furyl, anthryl thiophene Fen base, anthryl furyl, pyrenyl thienyl, pyrenyl furyl, benzo phenanthryl thienyl, benzo phenanthryl furyl,Base thiophene Base,Base furyl, fluoranthene base thienyl, fluoranthene base furyl, acenaphthenyl thienyl, acenaphthenyl furyl, fluorenyl thienyl or fluorenes Base furyl etc..These substituents are optionally taken by the alkoxyl of fluorine atom, the alkyl of carbon number 1～4 or carbon number 1～4 Generation.
As Ar2And Ar3In carbon number 1～4 alkyl, be not particularly limited, but as preference, can enumerate：First Base, ethyl, propyl group, isopropyl, normal-butyl, tert-butyl group etc..
As Ar2And Ar3In carbon number 1～4 alkoxyl, be not particularly limited, but as preference, can enumerate： Methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy or tert-butoxy etc..
As Ar2And Ar3In, monocyclic or condensed ring the aromatic hydrocarbyl of carbon number 6～18 that is replaced by fluorine atoms, It is not particularly limited, but as preference, can enumerates：Fluorophenyl, pentafluorophenyl group, fluorine xenyl, fluorine terphenyl, fluorine quaterphenyl Base, fluorine naphthylphenyl, naphthyl fluorophenyl, fluorine phenanthryl phenyl, phenanthryl fluorophenyl, fluorine anthryl phenyl, anthryl fluorophenyl, fluorine pyrenyl benzene Base, pyrenyl fluorophenyl, fluorine triphenyl phenyl, triphenyl fluorophenyl, fluorineBase phenyl,Base fluorophenyl, fluorine fluoranthene base phenyl, Fluoranthene fluorophenyl, fluorine acenaphthenyl phenyl, acenaphthenyl fluorophenyl, fluorine fluorenyl phenyl, fluorenyl fluorophenyl, fluoronaphthalene base xenyl, naphthyl fluorine connection Phenyl, fluoronaphthalene base, fluorophenyl naphthyl, phenyl-fluoride naphthyl, fluorine biphenyl naphthyl, biphenyl fluoronaphthalene base, fluorine phenanthryl naphthyl, phenanthryl fluoronaphthalene Base, fluorine anthryl naphthyl, anthryl fluoronaphthalene base, fluorine phenanthryl, fluorophenyl phenanthryl, phenyl-fluoride phenanthryl, fluoronaphthalene Ji Feiji, naphthyl fluorine phenanthryl, Fluorine anthryl, fluorophenyl anthryl, phenyl-fluoride anthryl, fluoronaphthalene base anthryl, naphthyl fluorine anthryl, fluorine pyrenyl, fluorophenyl pyrenyl, phenyl-fluoride pyrene Base, fluorobenzene and phenanthryl, fluorophenyl benzo phenanthryl, phenyl-fluoride benzo phenanthryl, fluorineBase, fluorophenylBase, phenyl-fluorideBase, fluorine Fluoranthene base, fluorophenyl fluoranthene base, phenyl-fluoride fluoranthene base, fluorine acenaphthenyl, fluorophenyl acenaphthenyl, phenyl-fluoride acenaphthenyl, fluorine fluorenyl, fluorophenyl fluorenes Base, phenyl-fluoride fluorenyl or fluorobenzene and fluorenyl etc..
From electron transporting material excellent aspect, preferred Ar2And Ar3Be each independently optionally link and/ Or the carbon number 6～24 of condensed ring aromatic hydrocarbyl, be only made up of 6 yuan of rings and optionally link and/or condensed ring carbon number 3 ～25 nitrogenous heteroaromatic group or by the atomic building in the atom group constituted selected from H, C, O and S and optionally link and/ Or the heteroaromatic group (these groups can also be replaced by the alkyl of carbon number 1～4) of the carbon number 3～25 of condensed ring.
Specifically, be more preferably each independently phenyl, xenyl, naphthylphenyl, phenanthryl phenyl, fluoranthene base phenyl, Pyridinylphenyl, quinolyl phenyl, thienyl phenyl, furyl phenyl, benzothienyl phenyl, benzofuranyl phenyl, two Benzothienyl phenyl, dibenzofuran group phenyl, naphthyl, pyridine radicals, benzothienyl, benzofuranyl, phenanthryl, anthryl, Dibenzothiophenes base or dibenzofuran group (these groups are optionally replaced by fluorine atom or methyl).
Further, more preferably Ar2And Ar3It is each independently the virtue of the optionally carbon number 6～24 of link and/or condensed ring Fragrant race's alkyl, be only made up of 6 yuan of rings and optionally link and/or condensed ring carbon number 3～25 nitrogenous heteroaromatic group or by Link selected from the atomic building in the atom group of H, C, O and S composition and optionally and/or condensed ring carbon number 3～25 it is miscellaneous Aromatic group.
Specifically, be more preferably each independently phenyl, tolyl, 3,5-dimethylphenyl, xenyl, naphthylphenyl, phenanthrene Base phenyl, fluoranthene base phenyl, pyridinylphenyl, quinolyl phenyl, thienyl phenyl, furyl phenyl, benzothienyl phenyl, Benzofuranyl phenyl, dibenzothiophenes base phenyl, dibenzofuran group phenyl, naphthyl, pyridine radicals, benzothienyl, benzo Furyl, phenanthryl, anthryl, dibenzothiophenes base or dibenzofuran group, be more preferably each independently phenyl, tolyl, 3,5-dimethylphenyl, xenyl, naphthylphenyl, phenanthryl phenyl, pyridinylphenyl, dibenzothiophenes base phenyl, dibenzofuran group Phenyl, naphthyl, pyridine radicals, benzothienyl, benzofuranyl, phenanthryl, anthryl, dibenzothiophenes base or dibenzofuran group, Further preferably it is each independently phenyl, tolyl, 3,5-dimethylphenyl, xenyl, naphthylphenyl, phenanthryl phenyl, pyridine radicals Phenyl, dibenzothiophenes base phenyl, dibenzofuran group phenyl, naphthyl, pyridine radicals or phenanthryl.
It should be noted that in formula (1), from electron transporting material excellent aspect, preferred Ar2With/ Or Ar3It is each independently the optional link of carbon number 10～24 and/or the aromatic hydrocarbyl of condensed ring, is only made up of 6 yuan of rings And optionally link and/or condensed ring carbon number 3～25 nitrogenous heteroaromatic group or comprising selected from H, C, O and S composition The optional link of the carbon number 3～25 of the atom in atom group and/or the heteroaromatic group of condensed ring.
As such Ar2And/or Ar3, preferably xenyl, naphthylphenyl, phenanthryl phenyl, fluoranthene base phenyl, pyridine radicals Phenyl, quinolyl phenyl, thienyl phenyl, furyl phenyl, benzothienyl phenyl, benzofuranyl phenyl, dibenzo thiophene Fen base phenyl, dibenzofuran group phenyl, naphthyl, benzothienyl, benzofuranyl, phenanthryl, anthryl, dibenzothiophenes base, Or dibenzofuran group (these groups are optionally replaced by fluorine atom or methyl), more preferably xenyl, naphthylphenyl, phenanthryl benzene Base, fluoranthene base phenyl, pyridinylphenyl, quinolyl phenyl, thienyl phenyl, furyl phenyl, benzothienyl phenyl, benzo Furyl phenyl, dibenzothiophenes base phenyl, dibenzofuran group phenyl, naphthyl, benzothienyl, benzofuranyl, phenanthryl, Anthryl, dibenzothiophenes base or dibenzofuran group, more preferably xenyl, naphthylphenyl, phenanthryl phenyl, pyridine radicals Phenyl, dibenzothiophenes base phenyl, dibenzofuran group phenyl, naphthyl or phenanthryl.
As Ar2And Ar3Concrete example, be not particularly limited, but as preference, can enumerate：Phenyl, p-methylphenyl, Tolyl, o-tolyl, 2,4- 3,5-dimethylphenyls, 3,5- 3,5-dimethylphenyls,Base, 2- ethylphenyls, 3- ethylphenyls, 4- Ethylphenyl, 2,4- diethyl phenyls, 3,5- diethyl phenyls, 2- propyl group phenyl, 3- propyl group phenyl, 4- propyl group phenyl, 2,4- Dipropyl phenyl, 3,5- dipropyl phenyl, 2- isopropyl phenyls, 3- isopropyl phenyls, 4- isopropyl phenyls, 2,4- diisopropyls Phenyl, 3,5- diisopropyl phenyls, 2- butyl phenyls, 3- butyl phenyls, 4- butyl phenyls, 2,4- dibutylphenyls, 3,5- bis- Butyl phenyl, 2- tert-butyl-phenyls, 3- tert-butyl-phenyls, 4- tert-butyl-phenyls, 2,4- di-tert-butyl-phenyls, 3,5- di-t-butyls Phenyl, biphenyl -2- bases, biphenyl -3- bases, biphenyl -4- bases, 3- methyl biphenyl -4- bases, 2 '-methyl biphenyl -4- bases, 4 '-methyl connection Benzene -4- bases, 2,2 '-dimethyl diphenyl -4- bases, 2 ', 4 ', 6 '-trimethylbiphenyl -4- bases, 6- methyl biphenyl -3- bases, 5- methyl Biphenyl -3- bases, 2 '-methyl biphenyl -3- bases, 4 '-methyl biphenyl -3- bases, 6,2 '-dimethyl diphenyl -3- bases, 2 ', 4 ', 6 '-three Methyl biphenyl -3- bases, 5- methyl biphenyl -2- bases, 6- methyl biphenyl -2- bases, 2 '-methyl biphenyl -2- bases, 4 '-methyl biphenyl -2- Base, 6,2 '-dimethyl diphenyl -2- bases, 2 ', 4 ', 6 '-trimethylbiphenyl -2- bases, 3- ethyl biphenyl -4- bases, 4 '-ethyl biphenyl - 4- bases, 2 ', 4 ', 6 '-triethyl group biphenyl -4- bases, 6- ethyl biphenyl -3- bases, 4 '-ethyl biphenyl -3- bases, 5- ethyl biphenyl -2- Base, 4 '-ethyl biphenyl -2- bases, 2 ', 4 ', 6 '-triethyl group biphenyl -2- bases, 3- pentylbiphenyl -4- bases, 4 '-pentylbiphenyl -4- Base, 2 ', 4 ', 6 '-tripropyl biphenyl -4- bases, 6- pentylbiphenyl -3- bases, 4 '-pentylbiphenyl -3- bases, 5- pentylbiphenyl -2- bases, 4 '-pentylbiphenyl -2- bases, 2 ', 4 ', 6 '-tripropyl biphenyl -2- bases, 3- isopropyl biphenyl -4- bases, 4 '-isopropyl biphenyl -4- Base, 2 ', 4 ', 6 '-tri isopropyl biphenyl -4- bases, 6- isopropyl biphenyl -3- bases, 4 '-isopropyl biphenyl -3- bases, 5- isopropyls connection Benzene -2- bases, 4 '-isopropyl biphenyl -2- bases, 2 ', 4 ', 6 '-tri isopropyl biphenyl -2- bases, 3- butyl biphenyl -4- bases, 4 '-butyl Biphenyl -4- bases, 2 ', 4 ', 6 '-tributyl biphenyl -4- bases, 6- butyl biphenyl -3- bases, 4 '-butyl biphenyl -3- bases, 5- butyl connection Benzene -2- bases, 4 '-butyl biphenyl -2- bases, 2 ', 4 ', 6 '-tributyl biphenyl -2- bases, 3- tert-butyl group biphenyl -4- bases, 4 '-tert-butyl group Biphenyl -4- bases, 2 ', 4 ', 6 '-tri-tert biphenyl -4- bases, 6- tert-butyl group biphenyl -3- bases, 4 '-tert-butyl group biphenyl -3- bases, 5- Tert-butyl group biphenyl -2- bases, 4 '-tert-butyl group biphenyl -2- bases, 2 ', 4 ', 6 '-tri-tert biphenyl -2- bases, 2- pyridine radicals, 3- pyridines Base, 4- pyridine radicals, 2- picoline -3- bases, 2- picoline -4- bases, 2- picoline -5- bases, 2- picoline -6- bases, 3- picoline -2- bases, 3- picoline -4- bases, 3- picoline -5- bases, 3- picoline -6- bases, 4- picoline -2- Base, 4- picoline -3- bases, 2,6- lutidines -3- bases, 2,6- lutidines -4- bases, 3,6- lutidines -2- Base, 3,6- lutidines -4- bases, 3,6- lutidines -5- bases, 2- phenylpyridine -6- bases, 3- phenylpyridine -6- bases, 4- Phenylpyridine -6- bases, 5- phenylpyridine -6- bases, 2- phenylpyridine -3- bases, 2- phenylpyridine -5- bases, 3- phenylpyridine -5- Base, 4- phenylpyridine -3- bases, 3- phenylpyridine -4- bases, 2- phenylpyridine -4- bases, 2- (2- pyridine radicals) phenyl, 3- (2- pyridines Base) phenyl, 4- (2- pyridine radicals) phenyl, 2- (3- pyridine radicals) phenyl, 3- (3- pyridine radicals) phenyl, 4- (3- pyridine radicals) phenyl, 2- (4- pyridine radicals) phenyl, 3- (4- pyridine radicals) phenyl, 4- (4- pyridine radicals) phenyl, 2- (3- methyl -2- pyridine radicals) phenyl, 3- (3- methyl -2- pyridine radicals) phenyl, 4- (3- methyl -2- pyridine radicals) phenyl, 2- (4- methyl -2- pyridine radicals) phenyl, 3- (4- first Base -2- pyridine radicals) phenyl, 4- (4- methyl -2- pyridine radicals) phenyl, 2- (5- methyl -2- pyridine radicals) phenyl, 3- (5- methyl -2- Pyridine radicals) phenyl, 4- (5- methyl -2- pyridine radicals) phenyl, 2- (6- methyl -2- pyridine radicals) phenyl, 3- (6- methyl -2- pyridines Base) phenyl, 4- (6- methyl -2- pyridine radicals) phenyl, 2- (2- methyl -3- pyridine radicals) phenyl, 3- (2- methyl -3- pyridine radicals) benzene Base, 4- (2- methyl -3- pyridine radicals) phenyl, 2- (4- methyl -3- pyridine radicals) phenyl, 3- (4- methyl -3- pyridine radicals) phenyl, 4- (4- methyl -3- pyridine radicals) phenyl, 2- (5- methyl -3- pyridine radicals) phenyl, 3- (5- methyl -3- pyridine radicals) phenyl, 4- (5- first Base -3- pyridine radicals) phenyl, 2- (6- methyl -3- pyridine radicals) phenyl, 3- (6- methyl -3- pyridine radicals) phenyl, 4- (6- methyl -3- Pyridine radicals) phenyl, 2- (2- methyl -4- pyridine radicals) phenyl, 3- (2- methyl -4- pyridine radicals) phenyl, 4- (2- methyl -4- pyridines Base) phenyl, 2- (3- methyl -4- pyridine radicals) phenyl, 3- (3- methyl -4- pyridine radicals) phenyl, 4- (3- methyl -4- pyridine radicals) benzene Base, 2- (2,4- dimethyl -3- pyridine radicals) phenyl, 3- (2,4- dimethyl -3- pyridine radicals) phenyl, 4- (2,4- dimethyl -3- pyrroles Piperidinyl) phenyl, 2- (3,5- dimethyl -4- pyridine radicals) phenyl, 3- (3,5- dimethyl -4- pyridine radicals) phenyl, 4- (3,5- diformazans Base -4- pyridine radicals) phenyl, 2- (3- phenyl -2- pyridine radicals) phenyl, 3- (3- phenyl -2- pyridine radicals) phenyl, 4- (3- phenyl -2- Pyridine radicals) phenyl, 2- (4- phenyl -2- pyridine radicals) phenyl, 3- (4- phenyl -2- pyridine radicals) phenyl, 4- (4- phenyl -2- pyridines Base) phenyl, 2- (5- phenyl -2- pyridine radicals) phenyl, 3- (5- phenyl -2- pyridine radicals) phenyl, 4- (5- phenyl -2- pyridine radicals) benzene Base, 2- (6- phenyl -2- pyridine radicals) phenyl, 3- (6- phenyl -2- pyridine radicals) phenyl, 4- (6- phenyl -2- pyridine radicals) phenyl, 2- (2- phenyl -3- pyridine radicals) phenyl, 3- (2- phenyl -3- pyridine radicals) phenyl, 4- (2- phenyl -3- pyridine radicals) phenyl, 2- (4- benzene Base -3- pyridine radicals) phenyl, 3- (4- phenyl -3- pyridine radicals) phenyl, 4- (4- phenyl -3- pyridine radicals) phenyl, 2- (5- phenyl -3- Pyridine radicals) phenyl, 3- (5- phenyl -3- pyridine radicals) phenyl, 4- (5- phenyl -3- pyridine radicals) phenyl, 2- (6- phenyl -3- pyridines Base) phenyl, 3- (6- phenyl -3- pyridine radicals) phenyl, 4- (6- phenyl -3- pyridine radicals) phenyl, 2- (2- phenyl -4- pyridine radicals) benzene Base, 3- (2- phenyl -4- pyridine radicals) phenyl, 4- (2- phenyl -4- pyridine radicals) phenyl, 2- (3- phenyl -4- pyridine radicals) phenyl, 3- (3- phenyl -4- pyridine radicals) phenyl, 4- (3- phenyl -4- pyridine radicals) phenyl, 2- (2,4- diphenyl -3- pyridine radicals) phenyl, 3- (2,4- diphenyl -3- pyridine radicals) phenyl, 4- (2,4- diphenyl -3- pyridine radicals) phenyl, 2- (3,5- diphenyl -4- pyridine radicals) Phenyl, 3- (3,5- diphenyl -4- pyridine radicals) phenyl, 4- (3,5- diphenyl -4- pyridine radicals) phenyl, 2- (1- naphthyls) phenyl, 3- (1- naphthyls) phenyl, 4- (1- naphthyls) phenyl, 2- (2- naphthyls) phenyl, 3- (2- naphthyls) phenyl, 4- (2- naphthyls) phenyl, 2- (1- phenanthryl) phenyl, 3- (1- phenanthryl) phenyl, 4- (1- phenanthryl) phenyl, 2- (2- phenanthryl) phenyl, 3- (2- phenanthryl) phenyl, 4- (2- phenanthryl) phenyl, 2- (3- phenanthryl) phenyl, 3- (3- phenanthryl) phenyl, 4- (3- phenanthryl) phenyl, 2- (4- phenanthryl) phenyl, 3- (4- phenanthryl) phenyl, 4- (4- phenanthryl) phenyl, 2- (9- phenanthryl) phenyl, 3- (9- phenanthryl) phenyl, 4- (9- phenanthryl) phenyl, 2- (1- anthryls) phenyl, 3- (1- anthryls) phenyl, 4- (1- anthryls) phenyl, 2- (2- anthryls) phenyl, 3- (2- anthryls) phenyl, 4- (2- anthryls) phenyl, 2- (9- anthryls) phenyl, 3- (9- anthryls) phenyl, 4- (9- anthryls) phenyl, 2- (1- pyrenyls) phenyl, 3- (1- pyrenyls) phenyl, 4- (1- pyrenyls) phenyl, 2- (2- pyrenyls) phenyl, 3- (2- pyrenyls) phenyl, 4- (2- pyrenyls) phenyl, 2- (4- pyrenyls) phenyl, 3- (4- pyrenyls) phenyl, 4- (4- pyrenyls) phenyl, 2- (fluoranthene -1- bases) phenyl, 3- (fluoranthene -1- bases) benzene Base, 4- (fluoranthene -1- bases) phenyl, 2- (fluoranthene -2- bases) phenyl, 3- (fluoranthene -2- bases) phenyl, 4- (fluoranthene -2- bases) phenyl, 2- (fluoranthene -3- bases) phenyl, 3- (fluoranthene -3- bases) phenyl, 4- (fluoranthene -3- bases) phenyl, 2- (fluoranthene -4- bases) phenyl, 3- are (glimmering Anthracene -4- bases) phenyl, 4- (fluoranthene -4- bases) phenyl, 2- (fluoranthene -5- bases) phenyl, 3- (fluoranthene -5- bases) phenyl, 4- (fluoranthene -5- Base) phenyl, 2- (triphenylene -1- bases) phenyl, 3- (triphenylene -1- bases) phenyl, 4- (triphenylene -1- bases) phenyl, 2- (Sanyas Benzene -2- bases) phenyl, 3- (triphenylene -2- bases) phenyl, 4- (triphenylene -2- bases) phenyl, 2- (- 1- bases) phenyl, 3- (- 1- yls) phenyl, 4- (- 1- bases) phenyl, 2- (- 2- bases) phenyl, 3- (- 2- bases) phenyl, 4- (- 2- bases) phenyl, 2- (- 3- bases) phenyl, 3- (- 3- bases) phenyl, 4- (- 3- bases) phenyl, 2- (- 4- bases) phenyl, 3- (- 4- bases) benzene Base, 4- (- 4- bases) phenyl, 2- (- 5- bases) phenyl, 3- (- 5- bases) phenyl, 4- (- 5- bases) phenyl, 2- (-6- Base) phenyl, 3- (- 6- bases) phenyl, 4- (- 6- bases) phenyl, 2- (acenaphthene -1- bases) phenyl, 3- (acenaphthene -1- bases) phenyl, 4- (acenaphthene -1- bases) phenyl, 2- (acenaphthene -3- bases) phenyl, 3- (acenaphthene -3- bases) phenyl, 4- (acenaphthene -3- bases) phenyl, 2- (acenaphthene -4- bases) benzene Base, 3- (acenaphthene -4- bases) phenyl, 4- (acenaphthene -4- bases) phenyl, 2- (acenaphthene -5- bases) phenyl, 3- (acenaphthene -5- bases) phenyl, 4- (acenaphthene -5- Base) phenyl, 2- (fluorenes -1- bases) phenyl, 3- (fluorenes -1- bases) phenyl, 4- (fluorenes -1- bases) phenyl, 2- (fluorenes -2- bases) phenyl, 3- (fluorenes -2- bases) phenyl, 4- (fluorenes -2- bases) phenyl, 2- (fluorenes -3- bases) phenyl, 3- (fluorenes -3- bases) phenyl, 4- (fluorenes -3- bases) benzene Base, 2- (fluorenes -4- bases) phenyl, 3- (fluorenes -4- bases) phenyl, 4- (fluorenes -4- bases) phenyl, 2- (pyrimidine -2-base) phenyl, 3- (pyrimidine - 2- yls) phenyl, 4- (pyrimidine -2-base) phenyl, 2- (pyrimidine-4-yl) phenyl, 3- (pyrimidine-4-yl) phenyl, 4- (pyrimidine-4-yl) Phenyl, 2- (pyrimidine -5- bases) phenyl, 3- (pyrimidine -5- bases) phenyl, 4- (pyrimidine -5- bases) phenyl, 2- (2- quinolyls) phenyl, 3- (2- quinolyls) phenyl, 4- (2- quinolyls) phenyl, 2- (3- quinolyls) phenyl, 3- (3- quinolyls) phenyl, 4- (3- quinoline Base) phenyl, 2- (4- quinolyls) phenyl, 3- (4- quinolyls) phenyl, 4- (4- quinolyls) phenyl, 2- (5- quinolyls) phenyl, 3- (5- quinolyls) phenyl, 4- (5- quinolyls) phenyl, 2- (6- quinolyls) phenyl, 3- (6- quinolyls) phenyl, 4- (6- quinoline Base) phenyl, 2- (7- quinolyls) phenyl, 3- (7- quinolyls) phenyl, 4- (7- quinolyls) phenyl, 2- (8- quinolyls) phenyl, 3- (8- quinolyls) phenyl, 4- (8- quinolyls) phenyl, [] 2- (2- isoquinolyls) phenyl, 3- (2- isoquinolyls) phenyl, 4- (2- isoquinolyls) phenyl, 2- (3- isoquinolyls) phenyl, 3- (3- isoquinolyls) phenyl, 4- (3- isoquinolyls) phenyl, 2- (4- isoquinolyls) phenyl, 3- (4- isoquinolyls) phenyl, 4- (4- isoquinolyls) phenyl, 2- (5- isoquinolyls) phenyl, 3- (5- isoquinolyls) phenyl, 4- (5- isoquinolyls) phenyl, 2- (6- isoquinolyls) phenyl, 3- (6- isoquinolyls) phenyl, 4- (6- isoquinolyls) phenyl, 2- (7- isoquinolyls) phenyl, 3- (7- isoquinolyls) phenyl, 4- (7- isoquinolyls) phenyl, 2- (8- isoquinolyls) phenyl, 3- (8- isoquinolyls) phenyl, 4- (8- isoquinolyls) phenyl, 2- (phenanthridines -2- bases) phenyl, 3- (phenanthridines -2- bases) phenyl, 4- (phenanthridines -2- bases) phenyl, 2- (phenanthridines -3- bases) phenyl, 3- (phenanthridines -3- bases) phenyl, 4- are (luxuriant and rich with fragrance Pyridine -3- bases) phenyl, 2- (phenanthridines -4- bases) phenyl, 3- (phenanthridines -4- bases) phenyl, 4- (phenanthridines -4- bases) phenyl, 2- (phenanthridines -5- Base) phenyl, 3- (phenanthridines -5- bases) phenyl, 4- (phenanthridines -5- bases) phenyl, 2- (phenanthridines -6- bases) phenyl, 3- (phenanthridines -6- bases) benzene Base, 4- (phenanthridines -6- bases) phenyl, 2- (phenanthridines -7- bases) phenyl, 3- (phenanthridines -7- bases) phenyl, 4- (phenanthridines -7- bases) phenyl, 2- (phenanthridines -8- bases) phenyl, 3- (phenanthridines -8- bases) phenyl, 4- (phenanthridines -8- bases) phenyl, 2- (phenanthridines -9- bases) phenyl, 3- are (luxuriant and rich with fragrance Pyridine -9- bases) phenyl, 4- (phenanthridines -9- bases) phenyl, 2- (phenanthridines -10- bases) phenyl, 3- (phenanthridines -10- bases) phenyl, 4- (phenanthridines - 10- yls) phenyl, 2- (benzo [h] quinoline -2- bases) phenyl, 3- (benzo [h] quinoline -2- bases) phenyl, 4- (benzo [h] quinoline - 2- yls) phenyl, 2- (benzo [h] quinoline -3- bases) phenyl, 3- (benzo [h] quinoline -3- bases) phenyl, 4- (benzo [h] quinoline -3- Base) phenyl, 2- (benzo [h] quinolyl-4) phenyl, 3- (benzo [h] quinolyl-4) phenyl, 4- (benzo [h] quinoline -4- Base) phenyl, 2- (benzo [h] quinoline -5- bases) phenyl, 3- (benzo [h] quinoline -5- bases) phenyl, 4- (benzo [h] quinoline -5- Base) phenyl, 2- (benzo [h] quinoline -6- bases) phenyl, 3- (benzo [h] quinoline -6- bases) phenyl, 4- (benzo [h] quinoline -6- Base) phenyl, 2- (benzo [h] quinoline -7- bases) phenyl, 3- (benzo [h] quinoline -7- bases) phenyl, 4- (benzo [h] quinoline -7- Base) phenyl, 2- (benzo [h] quinoline-8-yl) phenyl, 3- (benzo [h] quinoline-8-yl) phenyl, 4- (benzo [h] quinoline -8- Base) phenyl, 2- (benzo [h] quinoline -9- bases) phenyl, 3- (benzo [h] quinoline -9- bases) phenyl, 4- (benzo [h] quinoline -9- Base) phenyl, 2- (benzo [h] quinoline -10- bases) phenyl, 3- (benzo [h] quinoline -10- bases) phenyl, 4- (benzo [h] quinoline - 10- yls) phenyl, 2- (acridine -1- bases) phenyl, 3- (acridine -1- bases) phenyl, 4- (acridine -1- bases) phenyl, 2- (acridine -2- Base) phenyl, 3- (acridine -2- bases) phenyl, 4- (acridine -2- bases) phenyl, 2- (acridine -3- bases) phenyl, 3- (acridine -3- bases) benzene Base, 4- (acridine -3- bases) phenyl, 2- (acridine -4- bases) phenyl, 3- (acridine -4- bases) phenyl, 4- (acridine -4- bases) phenyl, 2- (acridine -9- bases) phenyl, 3- (acridine -9- bases) phenyl, 4- (acridine -9- bases) phenyl, 2- (2- thienyls) phenyl, 3- (2- thiophenes Fen base) phenyl, 4- (2- thienyls) phenyl, 2- (3- thienyls) phenyl, 3- (3- thienyls) phenyl, 4- (3- thienyls) benzene Base, 2- (3 methyl thiophene -2- bases) phenyl, 3- (3 methyl thiophene -2- bases) phenyl, 4- (3 methyl thiophene -2- bases) phenyl, 2- (4- methylthiophene -2- bases) phenyl, 3- (4- methylthiophene -2- bases) phenyl, 4- (4- methylthiophene -2- bases) phenyl, 2- (5- first Base thiophene -2- bases) phenyl, 3- (5- methylthiophene -2- bases) phenyl, 4- (5- methylthiophene -2- bases) phenyl, 2- (2- methyl thiazoliums Fen -3- bases) phenyl, 3- (2- methylthiophene -3- bases) phenyl, 4- (2- methylthiophene -3- bases) phenyl, 2- (4- methylthiophene -3- Base) phenyl, 3- (4- methylthiophene -3- bases) phenyl, 4- (4- methylthiophene -3- bases) phenyl, 2- (5- methylthiophene -3- bases) benzene Base, 3- (5- methylthiophene -3- bases) phenyl, 4- (5- methylthiophene -3- bases) phenyl, 2- (3- tolylthiophene -2- bases) phenyl, 3- (3- tolylthiophene -2- bases) phenyl, 4- (3- tolylthiophene -2- bases) phenyl, 2- (4- tolylthiophene -2- bases) phenyl, 3- (4- benzene Base thiophene -2- bases) phenyl, 4- (4- tolylthiophene -2- bases) phenyl, 2- (5- tolylthiophene -2- bases) phenyl, 3- (5- phenyl thiophenes Fen -2- bases) phenyl, 4- (5- tolylthiophene -2- bases) phenyl, 2- (2- tolylthiophene -3- bases) phenyl, 3- (2- tolylthiophene -3- Base) phenyl, 4- (2- tolylthiophene -3- bases) phenyl, 2- (4- tolylthiophene -3- bases) phenyl, 3- (4- tolylthiophene -3- bases) benzene Base, 4- (4- tolylthiophene -3- bases) phenyl, 2- (5- tolylthiophene -3- bases) phenyl, 3- (5- tolylthiophene -3- bases) phenyl, 4- (5- tolylthiophene -3- bases) phenyl, 3- (2- furyls) phenyl, 4- (2- furyls) phenyl, 2- (3- furyls) phenyl, 3- (3- furyls) phenyl, 4- (3- furyls) phenyl, 2- (3- methylfuran -2- bases) phenyl, 3- (3- methylfuran -2- bases) benzene Base, 4- (3- methylfuran -2- bases) phenyl, 2- (4- methylfuran -2- bases) phenyl, 3- (4- methylfuran -2- bases) phenyl, 4- (4- methylfuran -2- bases) phenyl, 2- (5- methylfuran -2- bases) phenyl, 3- (5- methylfuran -2- bases) phenyl, 4- (5- first Base furans -2- bases) phenyl, 2- (2- methylfuran -3- bases) phenyl, 3- (2- methylfuran -3- bases) phenyl, 4- (2- methyl furans Mutter -3- bases) phenyl, 2- (4- methylfuran -3- bases) phenyl, 3- (4- methylfuran -3- bases) phenyl, 4- (4- methylfuran -3- Base) phenyl, 2- (5- methylfuran -3- bases) phenyl, 3- (5- methylfuran -3- bases) phenyl, 4- (5- methylfuran -3- bases) benzene Base, 2- (3- benzofurane -2- bases) phenyl, 3- (3- benzofurane -2- bases) phenyl, 4- (3- benzofurane -2- bases) phenyl, 2- (4- benzofurane -2- bases) phenyl, 3- (4- benzofurane -2- bases) phenyl, 4- (4- benzofurane -2- bases) phenyl, 2- (5- benzene Base furans -2- bases) phenyl, 3- (5- benzofurane -2- bases) phenyl, 4- (5- benzofurane -2- bases) phenyl, 2- (2- phenyl furans Mutter -3- bases) phenyl, 3- (2- benzofurane -3- bases) phenyl, 4- (2- benzofurane -3- bases) phenyl, 2- (4- benzofurane -3- Base) phenyl, 3- (4- benzofurane -3- bases) phenyl, 4- (4- benzofurane -3- bases) phenyl, 2- (5- benzofurane -3- bases) benzene Base, 3- (5- benzofurane -3- bases) phenyl, 4- (5- benzofurane -3- bases) phenyl, 2- (2- benzos [b] thienyl) phenyl, 3- (2- benzos [b] thienyl) phenyl, 4- (2- benzos [b] thienyl) phenyl, 2- (3- benzos [b] thienyl) phenyl, 3- (3- benzene And [b] thienyl) phenyl, 4- (3- benzos [b] thienyl) phenyl, 2- (4- benzos [b] thienyl) phenyl, 3- (4- benzos [b] Thienyl) phenyl, 4- (4- benzos [b] thienyl) phenyl, 2- (5- benzos [b] thienyl) phenyl, 3- (5- benzos [b] thiophene Base) phenyl, 4- (5- benzos [b] thienyl) phenyl, 2- (6- benzos [b] thienyl) phenyl, 3- (6- benzos [b] thienyl) benzene Base, 4- (6- benzos [b] thienyl) phenyl, 2- (7- benzos [b] thienyl) phenyl, 3- (7- benzos [b] thienyl) phenyl, 4- (7- benzos [b] thienyl) phenyl, 2- (2- benzos [b] furyl) phenyl, 3- (2- benzos [b] furyl) phenyl, 4- (2- benzene And [b] furyl) phenyl, 2- (3- benzos [b] furyl) phenyl, 3- (3- benzos [b] furyl) phenyl, 4- (3- benzos [b] Furyl) phenyl, 2- (4- benzos [b] furyl) phenyl, 3- (4- benzos [b] furyl) phenyl, 4- (4- benzos [b] furans Base) phenyl, 2- (5- benzos [b] furyl) phenyl, 3- (5- benzos [b] furyl) phenyl, 4- (5- benzos [b] furyl) benzene Base, 2- (6- benzos [b] furyl) phenyl, 3- (6- benzos [b] furyl) phenyl, 4- (6- benzos [b] furyl) phenyl, 2- (7- benzos [b] furyl) phenyl, 3- (7- benzos [b] furyl) phenyl, 4- (7- benzos [b] furyl) phenyl, 2- (1- bis- Benzothienyl) phenyl, 3- (1- dibenzothiophenes bases) phenyl, 4- (1- dibenzothiophenes bases) phenyl, 2- (2- dibenzothiophenes Base) phenyl, 3- (2- dibenzothiophenes bases) phenyl, 4- (2- dibenzothiophenes bases) phenyl, 2- (3- dibenzothiophenes bases) phenyl, 3- (3- dibenzothiophenes bases) phenyl, 4- (3- dibenzothiophenes bases) phenyl, 2- (4- dibenzothiophenes bases) phenyl, 3- (4- bis- Benzothienyl) phenyl, 4- (4- dibenzothiophenes bases) phenyl, 2- (1- dibenzofuran groups) phenyl, 3- (1- dibenzofurans Base) phenyl, 4- (1- dibenzofuran groups) phenyl, 2- (2- dibenzofuran groups) phenyl, 3- (2- dibenzofuran groups) phenyl, 4- (2- dibenzofuran groups) phenyl, 2- (3- dibenzofuran groups) phenyl, 3- (3- dibenzofuran groups) phenyl, 4- (3- bis- Benzofuranyl) phenyl, 2- (4- dibenzofuran groups) phenyl, 3- (4- dibenzofuran groups) phenyl, 4- (4- dibenzofurans Base) phenyl, 3- (2- pyridine radicals) biphenyl -4- bases, 2 '-(2- pyridine radicals) biphenyl -4- bases, 4 '-(2- pyridine radicals) biphenyl -4- bases, 2,2 '-two (2- pyridine radicals) biphenyl -4- bases, 2 ', 4 ', 6 '-three (2- pyridine radicals) biphenyl -4- bases, 6- (2- pyridine radicals) biphenyl -3- Base, 5- (2- pyridine radicals) biphenyl -3- bases, 2 '-(2- pyridine radicals) biphenyl -3- bases, 4 '-(2- pyridine radicals) biphenyl -3- bases, 6,2 ' - Two (2- pyridine radicals) biphenyl -3- bases, 5- (2- pyridine radicals) biphenyl -2- bases, 6- (2- pyridine radicals) biphenyl -2- bases, 2 '-(2- pyridines Base) biphenyl -2- bases, 4 '-(2- pyridine radicals) biphenyl -2- bases, 6,2 '-two (2- pyridine radicals) biphenyl -2- bases, 3- (3- pyridine radicals) connection Benzene -4- bases, 2 '-(3- pyridine radicals) biphenyl -4- bases, 4 '-(3- pyridine radicals) biphenyl -4- bases, 2,2 '-two (3- pyridine radicals) biphenyl - 4- bases, 2 ', 4 ', 6 '-three (3- pyridine radicals) biphenyl -4- bases, 6- (3- pyridine radicals) biphenyl -3- bases, 5- (3- pyridine radicals) biphenyl -3- Base, 2 '-(3- pyridine radicals) biphenyl -3- bases, 4 '-(3- pyridine radicals) biphenyl -3- bases, 6,2 '-two (3- pyridine radicals) biphenyl -3- bases, 5- (3- pyridine radicals) biphenyl -2- bases, 6- (3- pyridine radicals) biphenyl -2- bases, 2 '-(3- pyridine radicals) biphenyl -2- bases, 4 '-(3- pyridines Base) biphenyl -2- bases, 6,2 '-two (3- pyridine radicals) biphenyl -2- bases, 3- (4- pyridine radicals) biphenyl -4- bases, 2 '-(4- pyridine radicals) connection Benzene -4- bases, 4 '-(4- pyridine radicals) biphenyl -4- bases, 2,2 '-two (4- pyridine radicals) biphenyl -4- bases, 2 ', 4 ', 6 '-three (4- pyridines Base) biphenyl -4- bases, 6- (4- pyridine radicals) biphenyl -3- bases, 5- (4- pyridine radicals) biphenyl -3- bases, 2 '-(4- pyridine radicals) biphenyl -3- Base, 4 '-(4- pyridine radicals) biphenyl -3- bases, 6,2 '-two (4- pyridine radicals) biphenyl -3- bases, 5- (4- pyridine radicals) biphenyl -2- bases, 6- (4- pyridine radicals) biphenyl -2- bases, 2 '-(4- pyridine radicals) biphenyl -2- bases, 4 '-(4- pyridine radicals) biphenyl -2- bases, 6,2 '-two (4- Pyridine radicals) biphenyl -2- bases, 3- (1- naphthyls) biphenyl -4- bases, 2 '-(1- naphthyls) biphenyl -4- bases, 4 '-(1- naphthyls) biphenyl -4- Base, 2,2 '-two (1- naphthyls) biphenyl -4- bases, 2 ', 4 ', 6 '-three (1- naphthyls) biphenyl -4- bases, 6- (1- naphthyls) biphenyl -3- bases, 5- (1- naphthyls) biphenyl -3- bases, 2 '-(1- naphthyls) biphenyl -3- bases, 4 '-(1- naphthyls) biphenyl -3- bases, 6,2 '-two (1- naphthyls) Biphenyl -3- bases, 5- (1- naphthyls) biphenyl -2- bases, 6- (1- naphthyls) biphenyl -2- bases, 2 '-(1- naphthyls) biphenyl -2- bases, 4 '-(1- Naphthyl) biphenyl -2- bases, 6,2 '-two (1- naphthyls) biphenyl -2- bases, 3- (2- naphthyls) biphenyl -4- bases, 2 '-(2- naphthyls) biphenyl - 4- bases, 4 '-(2- naphthyls) biphenyl -4- bases, 2,2 '-two (2- naphthyls) biphenyl -4- bases, 2 ', 4 ', 6 '-three (2- naphthyls) biphenyl -4- Base, 6- (2- naphthyls) biphenyl -3- bases, 5- (2- naphthyls) biphenyl -3- bases, 2 '-(2- naphthyls) biphenyl -3- bases, 4 '-(2- naphthyls) connection Benzene -3- bases, 6,2 '-two (2- naphthyls) biphenyl -3- bases, 5- (2- naphthyls) biphenyl -2- bases, 6- (2- naphthyls) biphenyl -2- bases, 2 ' - (2- naphthyls) biphenyl -2- bases, 4 '-(2- naphthyls) biphenyl -2- bases, 6,2 '-two (2- naphthyls) biphenyl -2- bases, 1- naphthyls, 2- naphthalenes Base, 1- phenylnaphthalene -2- bases, 1- phenylnaphthalene -3- bases, 1- phenylnaphthalene -4- bases, 1- phenylnaphthalene -5- bases, 1- phenylnaphthalene -6- bases, 1- benzene Base naphthalene -7- bases, 1- phenylnaphthalene -8- bases, 2- phenylnaphthalene -1- bases, 2- phenylnaphthalene -3- bases, 2- phenylnaphthalene -4- bases, 2- phenylnaphthalene -5- Base, 2- phenylnaphthalene -6- bases, 2- phenylnaphthalene -7- bases, 2- phenylnaphthalene -8- bases, 1- methyl naphthalene -4- bases, 1- methyl naphthalene -5- bases, 1- first Base naphthalene -6- bases, 1- methyl naphthalene -7- bases, 1- methyl naphthalene -8- bases, 2- methyl naphthalene -1- bases, 2- methyl naphthalene -3- bases, 2- methyl naphthalene -4- Base, 2- methyl naphthalene -5- bases, 2- methyl naphthalene -6- bases, 2- methyl naphthalene -7- bases, 2- methyl naphthalene -8- bases, 1- phenanthryl, 2- phenanthryl, 3- are luxuriant and rich with fragrance Base, 4- phenanthryl, 9- phenanthryl, 1- phenyl phenanthrene -2- bases, 1- phenyl phenanthrene -3- bases, 1- phenyl phenanthrene -4- bases, 1- phenyl phenanthrene -5- bases, 1- benzene Ji Fei -6- bases, 1- phenyl phenanthrene -7- bases, 1- phenyl phenanthrene -8- bases, 1- phenyl phenanthrene -9- bases, 1- phenyl phenanthrene -10- bases, 2- phenyl phenanthrene - 1- bases, 2- phenyl phenanthrene -3- bases, 2- phenyl phenanthrene -4- bases, 2- phenyl phenanthrene -5- bases, 2- phenyl phenanthrene -6- bases, 2- phenyl phenanthrene -7- bases, 2- Phenyl phenanthrene -8- bases, 2- phenyl phenanthrene -9- bases, 2- phenyl phenanthrene -10- bases, 3- phenyl phenanthrene -1- bases, 3- phenyl phenanthrene -2- bases, 3- phenyl Phenanthrene -4- bases, 3- phenyl phenanthrene -5- bases, 3- phenyl phenanthrene -6- bases, 3- phenyl phenanthrene -7- bases, 3- phenyl phenanthrene -8- bases, 3- phenyl phenanthrene -9- Base, 3- phenyl phenanthrene -10- bases, 4- phenyl phenanthrene -1- bases, 4- phenyl phenanthrene -2- bases, 4- phenyl phenanthrene -3- bases, 4- phenyl phenanthrene -5- bases, 4- Phenyl phenanthrene -6- bases, 4- phenyl phenanthrene -7- bases, 4- phenyl phenanthrene -8- bases, 4- phenyl phenanthrene -9- bases, 4- phenyl phenanthrene -10- bases, 1- methyl Phenanthrene -2- bases, 1- methylphenanthrene -3- bases, 1- methylphenanthrene -4- bases, 1- methylphenanthrene -5- bases, 1- methylphenanthrene -6- bases, 1- methylphenanthrene -7- Base, 1- methylphenanthrene -8- bases, 1- methylphenanthrene -9- bases, 1- methylphenanthrene -10- bases, 2- methylphenanthrene -1- bases, 2- methylphenanthrene -3- bases, 2- Methylphenanthrene -4- bases, 2- methylphenanthrene -5- bases, 2- methylphenanthrene -6- bases, 2- methylphenanthrene -7- bases, 2- methylphenanthrene -8- bases, 2- methylphenanthrenes - 9- bases, 2- methylphenanthrene -10- bases, 3- methylphenanthrene -1- bases, 3- methylphenanthrene -2- bases, 3- methylphenanthrene -4- bases, 3- methylphenanthrene -5- bases, 3- methylphenanthrene -6- bases, 3- methylphenanthrene -7- bases, 3- methylphenanthrene -8- bases, 3- methylphenanthrene -9- bases, 3- methylphenanthrene -10- bases, 4- methyl Phenanthrene -1- bases, 4- methylphenanthrene -2- bases, 4- methylphenanthrene -3- bases, 4- methylphenanthrene -5- bases, 4- methylphenanthrene -6- bases, 4- methylphenanthrene -7- Base, 4- methylphenanthrene -8- bases, 4- methylphenanthrene -9- bases, 4- methylphenanthrene -10- bases, 1- anthryls, 2- anthryls, 9- anthryls, 1- phenylanthracenes - 2- bases, 1- phenylanthracene -3- bases, 1- phenylanthracene -4- bases, 1- phenylanthracene -5- bases, 1- phenylanthracene -6- bases, 1- phenylanthracene -7- bases, 1- Phenylanthracene -8- bases, 1- phenylanthracene -9- bases, 1- phenylanthracene -10- bases, 2- phenylanthracene -1- bases, 2- phenylanthracene -3- bases, 2- phenyl Anthracene -4- bases, 2- phenylanthracene -5- bases, 2- phenylanthracene -6- bases, 2- phenylanthracene -7- bases, 2- phenylanthracene -8- bases, 2- phenylanthracene -9- Base, 2- phenylanthracene -10- bases, 9- phenylanthracene -1- bases, 9- phenylanthracene -2- bases, 9- phenylanthracene -3- bases, 9- phenylanthracene -4- bases, 9- Phenylanthracene -5- bases, 1- pyrenyls, 2- pyrenyls, 4- pyrenyls, 1- phenyl pyrene -2- bases, 1- phenyl pyrene -3- bases, 1- phenyl pyrene -4- bases, 1- Phenyl pyrene -5- bases, 1- phenyl pyrene -6- bases, 1- phenyl pyrene -7- bases, 1- phenyl pyrene -8- bases, 1- phenyl pyrene -9- bases, 1- phenyl pyrenes - 10- bases, 2- phenyl pyrene -1- bases, 2- phenyl pyrene -3- bases, 2- phenyl pyrene -4- bases, 2- phenyl pyrene -5- bases, 2- phenyl pyrene -6- bases, 2- phenyl pyrene -7- bases, 2- phenyl pyrene -8- bases, 2- phenyl pyrene -9- bases, 2- phenyl pyrene -10- bases, 9- phenyl pyrene -1- bases, 9- phenyl Pyrene -2- bases, 9- phenyl pyrene -3- bases, 9- phenyl pyrene -4- bases, 9- phenyl pyrene -5- bases, 9- phenyl pyrene -6- bases, 9- phenyl pyrene -7- Base, 9- phenyl pyrene -8- bases, 9- phenyl pyrene -10- bases, 1- methyl pyrene -2- bases, 1- methyl pyrene -3- bases, 1- methyl pyrene -4- bases, 1- Methyl pyrene -5- bases, 1- methyl pyrene -6- bases, 1- methyl pyrene -7- bases, 1- methyl pyrene -8- bases, 1- methyl pyrene -9- bases, 1- methyl pyrenes - 10- bases, 2- methyl pyrene -1- bases, 2- methyl pyrene -3- bases, 2- methyl pyrene -4- bases, 2- methyl pyrene -5- bases, 2- methyl pyrene -6- bases, 2- methyl pyrene -7- bases, 2- methyl pyrene -8- bases, 2- methyl pyrene -9- bases, 2- methyl pyrene -10- bases, 9- methyl pyrene -1- bases, 9- methyl Pyrene -2- bases, 9- methyl pyrene -3- bases, 9- methyl pyrene -4- bases, 9- methyl pyrene -5- bases, 9- methyl pyrene -6- bases, 9- methyl pyrene -7- Base, 9- methyl pyrene -8- bases, 9- methyl pyrene -10- bases, fluoranthene -1- bases, fluoranthene -1- bases, fluoranthene -2- bases, fluoranthene -3- bases, fluoranthene - 4- bases, fluoranthene -5- bases, fluoranthene -6- bases, fluoranthene -7- bases, fluoranthene -8- bases, fluoranthene -9- bases, fluoranthene -10- bases, triphenylene -1- Base, triphenylene -2- bases, acenaphthene -1- bases, acenaphthene -3- bases, acenaphthene -4- bases, acenaphthene -5- bases,- 1- bases,- 2- bases,- 5- bases,- 6- bases, 2- quinolyls, 3- quinolyls, 4- quinolyls, 5- quinolyls, 6- quinolyls, 7- quinolyls, 8- quinolyls, 1- isoquinolin Base, 3- isoquinolyls, 4- isoquinolyls, 5- isoquinolyls, 6- isoquinolyls, 7- isoquinolyls, 8- isoquinolyls, quinoxaline- 2- bases, quinoxaline -5- bases, quinoxalin-6-yl, quinazoline -2- bases, quinazoline -4- bases, quinazoline -5- bases, quinazoline -6- bases, Quinazoline -7- bases, quinazoline -8- bases, pyrazine -2- bases, pyrimidine -2-base, pyrimidine-4-yl, pyrimidine -5- bases, acridine -1- bases, a word used for translation Pyridine -1- bases, acridine -2- bases, acridine -3- bases, acridine -4- bases, acridine -9- bases, phenanthridines -1- bases, phenanthridines -1- bases, phenanthridines -2- Base, phenanthridines -3- bases, phenanthridines -4- bases, phenanthridines -6- bases, phenanthridines -7- bases, phenanthridines -8- bases, phenanthridines -9- bases, phenanthridines -10- bases, fen Piperazine -1- bases, azophenlyene -2- bases, benzo [h] quinoline -2- bases, benzo [h] quinoline -3- bases, benzo [h] quinolyl-4, benzo [h] Quinoline -5- bases, benzo [h] quinoline -6- bases, benzo [h] quinoline -7- bases, benzo [h] quinoline-8-yl, benzo [h] quinoline -9- Base, benzo [h] quinoline -10- bases, 2- thienyls, 3- thienyls, 2- furyls, 3- furyls, benzothiophene -2- bases, benzo thiophene Fen -3- bases, benzothiophene -4- bases, benzothiophene -5- bases, benzothiophene -6- bases, benzothiophene -7- bases, benzofuran -2- Base, benzofuran -3- bases, benzofuran -4- bases, benzofuran -5- bases, benzofuran -6- bases, benzofuran -7- bases, hexichol Bithiophene -1- bases, dibenzothiophenes -2- bases, dibenzothiophenes -3- bases, dibenzofurans -1- bases, dibenzofurans -2- bases, Dibenzofurans -3- bases, 3 methyl thiophene -2- bases, 4- methylthiophene -2- bases, 5- methylthiophene -2- bases, 2- methylthiophene -3- Base, 4- methylthiophene -3- bases, 5- methylthiophene -3- bases, 3- methylfuran -2- bases, 4- methylfuran -2- bases, 5- methyl furans Mutter -2- bases, 2- methylfuran -3- bases, 4- methylfuran -3- bases, 5- methylfuran -3- bases, 3- methyl benzothiophene -2- bases, 4- methyl benzothiophene -2- bases, 5- methyl benzothiophene -2- bases, 6- methyl benzothiophene -2- bases, 7- methyl benzothiophene -2- Base, 2- methyl benzothiophene -3- bases, 4- methyl benzothiophene -3- bases, 5- methyl benzothiophene -3- bases, 6- methyl benzo thiophenes Fen -3- bases, 7- methyl benzothiophene -3- bases, 2- methyl benzothiophene -4- bases, 3- methyl benzothiophene -4- bases, 5- methylbenzenes Bithiophene -4- bases, 6- methyl benzothiophene -4- bases, 7- methyl benzothiophene -4- bases, 2- methyl benzothiophene -5- bases, 3- first Base benzothiophene -5- bases, 4- methyl benzothiophene -5- bases, 6- methyl benzothiophene -5- bases, 7- methyl benzothiophene -5- bases, 2- methyl benzothiophene -6- bases, 3- methyl benzothiophene -6- bases, 4- methyl benzothiophene -6- bases, 5- methyl benzothiophene -6- Base, 7- methyl benzothiophene -6- bases, 2- methyl benzothiophene -7- bases, 3- methyl benzothiophene -7- bases, 4- methyl benzo thiophenes Fen -7- bases, 5- methyl benzothiophene -7- bases, 6- methyl benzothiophene -7- bases, 3- methyl benzofuran -2- bases, 4- methylbenzenes And furans -2- bases, 5- methyl benzofuran -2- bases, 6- methyl benzofuran -2- bases, 7- methyl benzofuran -2- bases, 2- first Base benzofuran -3- bases, 4- methyl benzofuran -3- bases, 5- methyl benzofuran -3- bases, 6- methyl benzofuran -3- bases, 7- methyl benzofuran -3- bases, 2- methyl benzofuran -4- bases, 3- methyl benzofuran -4- bases, 5- methyl benzofuran -4- Base, 6- methyl benzofuran -4- bases, 7- methyl benzofuran -4- bases, 2- methyl benzofuran -5- bases, 3- methyl benzo furans Mutter -5- bases, 4- methyl benzofuran -5- bases, 6- methyl benzofuran -5- bases, 7- methyl benzofuran -5- bases, 2- methylbenzenes And furans -6- bases, 3- methyl benzofuran -6- bases, 4- methyl benzofuran -6- bases, 5- methyl benzofuran -6- bases, 7- first Base benzofuran -6- bases, 2- methyl benzofuran -7- bases, 3- methyl benzofuran -7- bases, 4- methyl benzofuran -7- bases, 5- methyl benzofuran -7- bases, 6- methyl benzofuran -7- bases, 2- methyldibenzothiophene -1- bases, 3- methyldiphenyls and thiophene Fen -1- bases, 4-MDBT -1- bases, 6- methyldibenzothiophene -1- bases, 7- methyldibenzothiophene -1- bases, 8- Methyldibenzothiophene -1- bases, 9- methyldibenzothiophene -1- bases, 1- methyldibenzothiophene -2- bases, 3- methyldiphenyls are simultaneously Thiophene -2- bases, 4-MDBT -2- bases, 6- methyldibenzothiophene -2- bases, 7- methyldibenzothiophene -2- bases, 8- methyldibenzothiophene -2- bases, 9- methyldibenzothiophene -2- bases, 1- methyldibenzothiophene -3- bases, 2- methyldiphenyls Bithiophene -3- bases, 4-MDBT -3- bases, 6- methyldibenzothiophene -3- bases, 7- methyldibenzothiophene -3- Base, 8- methyldibenzothiophene -3- bases, 9- methyldibenzothiophene -3- bases, 2- methyldiphenyls and furans -1- bases, 3- methyl two Benzofuran -1- bases, 4- methyldiphenyls and furans -1- bases, 6- methyldiphenyls and furans -1- bases, 7- methyldiphenyls and furans -1- Base, 8- methyldiphenyls and furans -1- bases, 9- methyldiphenyls and furans -1- bases, 1- methyldiphenyls and furans -2- bases, 3- methyl two Benzofuran -2- bases, 4- methyldiphenyls and furans -2- bases, 6- methyldiphenyls and furans -2- bases, 7- methyldiphenyls and furans -2- Base, 8- methyldiphenyls and furans -2- bases, 9- methyldiphenyls and furans -2- bases, 1- methyldiphenyls and furans -3- bases, 2- methyl two Benzofuran -3- bases, 4- methyldiphenyls and furans -3- bases, 6- methyldiphenyls and furans -3- bases, 7- methyldiphenyls and furans -3- Base, 8- methyldiphenyls and furans -3- bases, 9- methyldiphenyls and furans -3- bases, 3- tolylthiophene -2- bases, 4- tolylthiophene -2- Base, 5- tolylthiophene -2- bases, 2- tolylthiophene -3- bases, 4- tolylthiophene -3- bases, 5- tolylthiophene -3- bases, 3- phenyl furans Mutter -2- bases, 4- benzofurane -2- bases, 5- benzofurane -2- bases, 2- benzofurane -3- bases, 4- benzofurane -3- bases, 5- benzene Base furans -3- bases, 3- phenyl benzothiophene -2- bases, 4- phenyl benzothiophene -2- bases, 5- phenyl benzothiophene -2- bases, 6- benzene Base benzothiophene -2- bases, 7- phenyl benzothiophene -2- bases, 2- phenyl benzothiophene -3- bases, 4- phenyl benzothiophene -3- bases, 5- phenyl benzothiophene -3- bases, 6- phenyl benzothiophene -3- bases, 7- phenyl benzothiophene -3- bases, 2- phenyl benzothiophene -4- Base, 3- phenyl benzothiophene -4- bases, 5- phenyl benzothiophene -4- bases, 6- phenyl benzothiophene -4- bases, 7- phenyl benzo thiophenes Fen -4- bases, 2- phenyl benzothiophene -5- bases, 3- phenyl benzothiophene -5- bases, 4- phenyl benzothiophene -5- bases, 6- phenyl benzene Bithiophene -5- bases, 7- phenyl benzothiophene -5- bases, 2- phenyl benzothiophene -6- bases, 3- phenyl benzothiophene -6- bases, 4- benzene Base benzothiophene -6- bases, 5- phenyl benzothiophene -6- bases, 7- phenyl benzothiophene -6- bases, 2- phenyl benzothiophene -7- bases, 3- phenyl benzothiophene -7- bases, 4- phenyl benzothiophene -7- bases, 5- phenyl benzothiophene -7- bases, 6- phenyl benzothiophene -7- Base, 3- phenyl benzofurans -2- bases, 4- phenyl benzofurans -2- bases, 5- phenyl benzofurans -2- bases, 6- phenyl benzo furans Mutter -2- bases, 7- phenyl benzofurans -2- bases, 2- phenyl benzofurans -3- bases, 4- phenyl benzofurans -3- bases, 5- phenyl benzene And furans -3- bases, 6- phenyl benzofurans -3- bases, 7- phenyl benzofurans -3- bases, 2- phenyl benzofurans -4- bases, 3- benzene Base benzofuran -4- bases, 5- phenyl benzofurans -4- bases, 6- phenyl benzofurans -4- bases, 7- phenyl benzofurans -4- bases, 2- phenyl benzofurans -5- bases, 3- phenyl benzofurans -5- bases, 4- phenyl benzofurans -5- bases, 6- phenyl benzofurans -5- Base, 7- phenyl benzofurans -5- bases, 2- phenyl benzofurans -6- bases, 3- phenyl benzofurans -6- bases, 4- phenyl benzo furans Mutter -6- bases, 5- phenyl benzofurans -6- bases, 7- phenyl benzofurans -6- bases, 2- phenyl benzofurans -7- bases, 3- phenyl benzene And furans -7- bases, 4- phenyl benzofurans -7- bases, 5- phenyl benzofurans -7- bases, 6- phenyl benzofurans -7- bases, 2- benzene Base dibenzothiophenes -1- bases, 3- phenyl dibenzothiophenes -1- bases, 4- phenyl dibenzothiophenes -1- bases, 6- phenyl dibenzo thiophenes Fen -1- bases, 7- phenyl dibenzothiophenes -1- bases, 8- phenyl dibenzothiophenes -1- bases, 9- phenyl dibenzothiophenes -1- bases, 1- Phenyl dibenzothiophenes -2- bases, 3- phenyl dibenzothiophenes -2- bases, 4- phenyl dibenzothiophenes -2- bases, 6- phenyl dibenzo Thiophene -2- bases, 7- phenyl dibenzothiophenes -2- bases, 8- phenyl dibenzothiophenes -2- bases, 9- phenyl dibenzothiophenes -2- bases, 1- phenyl dibenzothiophenes -3- bases, 2- phenyl dibenzothiophenes -3- bases, 4- phenyl dibenzothiophenes -3- bases, 6- phenyl hexichol Bithiophene -3- bases, 7- phenyl dibenzothiophenes -3- bases, 8- phenyl dibenzothiophenes -3- bases, 9- phenyl dibenzothiophenes -3- Base, 2- phenyl dibenzofurans -1- bases, 3- phenyl dibenzofurans -1- bases, 4- phenyl dibenzofurans -1- bases, 6- phenyl two Benzofuran -1- bases, 7- phenyl dibenzofurans -1- bases, 8- phenyl dibenzofurans -1- bases, 9- phenyl dibenzofurans -1- Base, 1- phenyl dibenzofurans -2- bases, 3- phenyl dibenzofurans -2- bases, 4- phenyl dibenzofurans -2- bases, 6- phenyl two Benzofuran -2- bases, 7- phenyl dibenzofurans -2- bases, 8- phenyl dibenzofurans -2- bases, 9- phenyl dibenzofurans -2- Base, 1- phenyl dibenzofurans -3- bases, 2- phenyl dibenzofurans -3- bases, 4- phenyl dibenzofurans -3- bases, 6- phenyl two Benzofuran -3- bases, 7- phenyl dibenzofurans -3- bases, 8- phenyl dibenzofurans -3- bases, 9- phenyl dibenzofurans -3- Base, 3- (2- pyridine radicals) thiophene -2- bases, 4- (2- pyridine radicals) thiophene -2- bases, 5- (2- pyridine radicals) thiophene -2- bases, 2- (2- pyrroles Piperidinyl) thiene-3-yl, 4- (2- pyridine radicals) thiene-3-yl, 5- (2- pyridine radicals) thiene-3-yl, 3- (2- pyridine radicals) furans- 2- bases, 4- (2- pyridine radicals) furans -2- bases, 5- (2- pyridine radicals) furans -2- bases, 2- (2- pyridine radicals) furans -3- bases, 4- (2- Pyridine radicals) furans -3- bases, 5- (2- pyridine radicals) furans -3- bases, 3- (2- pyridine radicals) benzothiophene -2- bases, 4- (2- pyridine radicals) Benzothiophene -2- bases, 5- (2- pyridine radicals) benzothiophene -2- bases, 6- (2- pyridine radicals) benzothiophene -2- bases, 7- (2- pyridines Base) benzothiophene -2- bases, 2- (2- pyridine radicals) benzothiophene -3- bases, 4- (2- pyridine radicals) benzothiophene -3- bases, 5- (2- pyrroles Piperidinyl) benzothiophene -3- bases, 6- (2- pyridine radicals) benzothiophene -3- bases, 7- (2- pyridine radicals) benzothiophene -3- bases, 2- (2- Pyridine radicals) benzothiophene -4- bases, 3- (2- pyridine radicals) benzothiophene -4- bases, 5- (2- pyridine radicals) benzothiophene -4- bases, 6- (2- pyridine radicals) benzothiophene -4- bases, 7- (2- pyridine radicals) benzothiophene -4- bases, 2- (2- pyridine radicals) benzothiophene -5- bases, 3- (2- pyridine radicals) benzothiophene -5- bases, 4- (2- pyridine radicals) benzothiophene -5- bases, 6- (2- pyridine radicals) benzothiophene -5- Base, 7- (2- pyridine radicals) benzothiophene -5- bases, 2- (2- pyridine radicals) benzothiophene -6- bases, 3- (2- pyridine radicals) benzothiophene - 6- bases, 4- (2- pyridine radicals) benzothiophene -6- bases, 5- (2- pyridine radicals) benzothiophene -6- bases, 7- (2- pyridine radicals) benzo thiophene Fen -6- bases, 2- (2- pyridine radicals) benzothiophene -7- bases, 3- (2- pyridine radicals) benzothiophene -7- bases, 4- (2- pyridine radicals) benzo Thiophene -7- bases, 5- (2- pyridine radicals) benzothiophene -7- bases, 6- (2- pyridine radicals) benzothiophene -7- bases, 3- (2- pyridine radicals) benzene And furans -2- bases, 4- (2- pyridine radicals) benzofuran -2- bases, 5- (2- pyridine radicals) benzofuran -2- bases, 6- (2- pyridine radicals) Benzofuran -2- bases, 7- (2- pyridine radicals) benzofuran -2- bases, 2- (2- pyridine radicals) benzofuran -3- bases, 4- (2- pyridines Base) benzofuran -3- bases, 5- (2- pyridine radicals) benzofuran -3- bases, 6- (2- pyridine radicals) benzofuran -3- bases, 7- (2- pyrroles Piperidinyl) benzofuran -3- bases, 2- (2- pyridine radicals) benzofuran -4- bases, 3- (2- pyridine radicals) benzofuran -4- bases, 5- (2- Pyridine radicals) benzofuran -4- bases, 6- (2- pyridine radicals) benzofuran -4- bases, 7- (2- pyridine radicals) benzofuran -4- bases, 2- (2- pyridine radicals) benzofuran -5- bases, 3- (2- pyridine radicals) benzofuran -5- bases, 4- (2- pyridine radicals) benzofuran -5- bases, 6- (2- pyridine radicals) benzofuran -5- bases, 7- (2- pyridine radicals) benzofuran -5- bases, 2- (2- pyridine radicals) benzofuran -6- Base, 3- (2- pyridine radicals) benzofuran -6- bases, 4- (2- pyridine radicals) benzofuran -6- bases, 5- (2- pyridine radicals) benzofuran - 6- bases, 7- (2- pyridine radicals) benzofuran -6- bases, 2- (2- pyridine radicals) benzofuran -7- bases, 3- (2- pyridine radicals) benzo furan Mutter -7- bases, 4- (2- pyridine radicals) benzofuran -7- bases, 5- (2- pyridine radicals) benzofuran -7- bases, 6- (2- pyridine radicals) benzo Furans -7- bases, 2- (2- pyridine radicals) dibenzothiophenes -1- bases, 3- (2- pyridine radicals) dibenzothiophenes -1- bases, 4- (2- pyridines Base) dibenzothiophenes -1- bases, 6- (2- pyridine radicals) dibenzothiophenes -1- bases, 7- (2- pyridine radicals) dibenzothiophenes -1- bases, 8- (2- pyridine radicals) dibenzothiophenes -1- bases, 9- (2- pyridine radicals) dibenzothiophenes -1- bases, 1- (2- pyridine radicals) dibenzothiophenes - 2- bases, 3- (2- pyridine radicals) dibenzothiophenes -2- bases, 4- (2- pyridine radicals) dibenzothiophenes -2- bases, 6- (2- pyridine radicals) hexichol Bithiophene -2- bases, 7- (2- pyridine radicals) dibenzothiophenes -2- bases, 8- (2- pyridine radicals) dibenzothiophenes -2- bases, 9- (2- pyridines Base) dibenzothiophenes -2- bases, 1- (2- pyridine radicals) dibenzothiophenes -3- bases, 2- (2- pyridine radicals) dibenzothiophenes -3- bases, 4- (2- pyridine radicals) dibenzothiophenes -3- bases, 6- (2- pyridine radicals) dibenzothiophenes -3- bases, 7- (2- pyridine radicals) dibenzothiophenes - 3- bases, 8- (2- pyridine radicals) dibenzothiophenes -3- bases, 9- (2- pyridine radicals) dibenzothiophenes -3- bases, 2- (2- pyridine radicals) hexichol And furans -1- bases, 3- (2- pyridine radicals) dibenzofurans -1- bases, 4- (2- pyridine radicals) dibenzofurans -1- bases, 6- (2- pyridines Base) dibenzofurans -1- bases, 7- (2- pyridine radicals) dibenzofurans -1- bases, 8- (2- pyridine radicals) dibenzofurans -1- bases, 9- (2- pyridine radicals) dibenzofurans -1- bases, 1- (2- pyridine radicals) dibenzofurans -2- bases, 3- (2- pyridine radicals) dibenzofurans - 2- bases, 4- (2- pyridine radicals) dibenzofurans -2- bases, 6- (2- pyridine radicals) dibenzofurans -2- bases, 7- (2- pyridine radicals) hexichol And furans -2- bases, 8- (2- pyridine radicals) dibenzofurans -2- bases, 9- (2- pyridine radicals) dibenzofurans -2- bases, 1- (2- pyridines Base) dibenzofurans -3- bases, 2- (2- pyridine radicals) dibenzofurans -3- bases, 4- (2- pyridine radicals) dibenzofurans -3- bases, 6- (2- pyridine radicals) dibenzofurans -3- bases, 7- (2- pyridine radicals) dibenzofurans -3- bases, 8- (2- pyridine radicals) dibenzofurans - 3- bases, 9- (2- pyridine radicals) dibenzofurans -3- bases, 3- (3- pyridine radicals) thiophene -2- bases, 4- (3- pyridine radicals) thiophene -2- bases, 5- (3- pyridine radicals) thiophene -2- bases, 2- (3- pyridine radicals) thiene-3-yl, 4- (3- pyridine radicals) thiene-3-yl, 5- (3- pyridines Base) thiene-3-yl, 3- (3- pyridine radicals) furans -2- bases, 4- (3- pyridine radicals) furans -2- bases, 5- (3- pyridine radicals) furans -2- Base, 2- (3- pyridine radicals) furans -3- bases, 4- (3- pyridine radicals) furans -3- bases, 5- (3- pyridine radicals) furans -3- bases, 3- (3- pyrroles Piperidinyl) benzothiophene -2- bases, 4- (3- pyridine radicals) benzothiophene -2- bases, 5- (3- pyridine radicals) benzothiophene -2- bases, 6- (3- Pyridine radicals) benzothiophene -2- bases, 7- (3- pyridine radicals) benzothiophene -2- bases, 2- (3- pyridine radicals) benzothiophene -3- bases, 4- (3- pyridine radicals) benzothiophene -3- bases, 5- (3- pyridine radicals) benzothiophene -3- bases, 6- (3- pyridine radicals) benzothiophene -3- bases, 7- (3- pyridine radicals) benzothiophene -3- bases, 2- (3- pyridine radicals) benzothiophene -4- bases, 3- (3- pyridine radicals) benzothiophene -4- Base, 5- (3- pyridine radicals) benzothiophene -4- bases, 6- (3- pyridine radicals) benzothiophene -4- bases, 7- (3- pyridine radicals) benzothiophene - 4- bases, 2- (3- pyridine radicals) benzothiophene -5- bases, 3- (3- pyridine radicals) benzothiophene -5- bases, 4- (3- pyridine radicals) benzo thiophene Fen -5- bases, 6- (3- pyridine radicals) benzothiophene -5- bases, 7- (3- pyridine radicals) benzothiophene -5- bases, 2- (3- pyridine radicals) benzo Thiophene -6- bases, 3- (3- pyridine radicals) benzothiophene -6- bases, 4- (3- pyridine radicals) benzothiophene -6- bases, 5- (3- pyridine radicals) benzene Bithiophene -6- bases, 7- (3- pyridine radicals) benzothiophene -6- bases, 2- (3- pyridine radicals) benzothiophene -7- bases, 3- (3- pyridine radicals) Benzothiophene -7- bases, 4- (3- pyridine radicals) benzothiophene -7- bases, 5- (3- pyridine radicals) benzothiophene -7- bases, 6- (3- pyridines Base) benzothiophene -7- bases, 3- (3- pyridine radicals) benzofuran -2- bases, 4- (3- pyridine radicals) benzofuran -2- bases, 5- (3- pyrroles Piperidinyl) benzofuran -2- bases, 6- (3- pyridine radicals) benzofuran -2- bases, 7- (3- pyridine radicals) benzofuran -2- bases, 2- (3- Pyridine radicals) benzofuran -3- bases, 4- (3- pyridine radicals) benzofuran -3- bases, 5- (3- pyridine radicals) benzofuran -3- bases, 6- (3- pyridine radicals) benzofuran -3- bases, 7- (3- pyridine radicals) benzofuran -3- bases, 2- (3- pyridine radicals) benzofuran -4- bases, 3- (3- pyridine radicals) benzofuran -4- bases, 5- (3- pyridine radicals) benzofuran -4- bases, 6- (3- pyridine radicals) benzofuran -4- Base, 7- (3- pyridine radicals) benzofuran -4- bases, 2- (3- pyridine radicals) benzofuran -5- bases, 3- (3- pyridine radicals) benzofuran - 5- bases, 4- (3- pyridine radicals) benzofuran -5- bases, 6- (3- pyridine radicals) benzofuran -5- bases, 7- (3- pyridine radicals) benzo furan Mutter -5- bases, 2- (3- pyridine radicals) benzofuran -6- bases, 3- (3- pyridine radicals) benzofuran -6- bases, 4- (3- pyridine radicals) benzo Furans -6- bases, 5- (3- pyridine radicals) benzofuran -6- bases, 7- (3- pyridine radicals) benzofuran -6- bases, 2- (3- pyridine radicals) benzene And furans -7- bases, 3- (3- pyridine radicals) benzofuran -7- bases, 4- (3- pyridine radicals) benzofuran -7- bases, 5- (3- pyridine radicals) Benzofuran -7- bases, 6- (3- pyridine radicals) benzofuran -7- bases, 2- (3- pyridine radicals) dibenzothiophenes -1- bases, 3- (3- pyridines Base) dibenzothiophenes -1- bases, 4- (3- pyridine radicals) dibenzothiophenes -1- bases, 6- (3- pyridine radicals) dibenzothiophenes -1- bases, 7- (3- pyridine radicals) dibenzothiophenes -1- bases, 8- (3- pyridine radicals) dibenzothiophenes -1- bases, 9- (3- pyridine radicals) dibenzothiophenes - 1- bases, 1- (3- pyridine radicals) dibenzothiophenes -2- bases, 3- (3- pyridine radicals) dibenzothiophenes -2- bases, 4- (3- pyridine radicals) hexichol Bithiophene -2- bases, 6- (3- pyridine radicals) dibenzothiophenes -2- bases, 7- (3- pyridine radicals) dibenzothiophenes -2- bases, 8- (3- pyridines Base) dibenzothiophenes -2- bases, 9- (3- pyridine radicals) dibenzothiophenes -2- bases, 1- (3- pyridine radicals) dibenzothiophenes -3- bases, 2- (3- pyridine radicals) dibenzothiophenes -3- bases, 4- (3- pyridine radicals) dibenzothiophenes -3- bases, 6- (3- pyridine radicals) dibenzothiophenes - 3- bases, 7- (3- pyridine radicals) dibenzothiophenes -3- bases, 8- (3- pyridine radicals) dibenzothiophenes -3- bases, 9- (3- pyridine radicals) hexichol Bithiophene -3- bases, 2- (3- pyridine radicals) dibenzofurans -1- bases, 3- (3- pyridine radicals) dibenzofurans -1- bases, 4- (3- pyridines Base) dibenzofurans -1- bases, 6- (3- pyridine radicals) dibenzofurans -1- bases, 7- (3- pyridine radicals) dibenzofurans -1- bases, 8- (3- pyridine radicals) dibenzofurans -1- bases, 9- (3- pyridine radicals) dibenzofurans -1- bases, 1- (3- pyridine radicals) dibenzofurans - 2- bases, 3- (3- pyridine radicals) dibenzofurans -2- bases, 4- (3- pyridine radicals) dibenzofurans -2- bases, 6- (3- pyridine radicals) hexichol And furans -2- bases, 7- (3- pyridine radicals) dibenzofurans -2- bases, 8- (3- pyridine radicals) dibenzofurans -2- bases, 9- (3- pyridines Base) dibenzofurans -2- bases, 1- (3- pyridine radicals) dibenzofurans -3- bases, 2- (3- pyridine radicals) dibenzofurans -3- bases, 4- (3- pyridine radicals) dibenzofurans -3- bases, 6- (3- pyridine radicals) dibenzofurans -3- bases, 7- (3- pyridine radicals) dibenzofurans - 3- bases, 8- (3- pyridine radicals) dibenzofurans -3- bases, 9- (3- pyridine radicals) dibenzofurans -3- bases, 3- (4- pyridine radicals) thiophene Fen -2- bases, 4- (4- pyridine radicals) thiophene -2- bases, 5- (4- pyridine radicals) thiophene -2- bases, 2- (4- pyridine radicals) thiene-3-yl, 4- (4- pyridine radicals) thiene-3-yl, 5- (4- pyridine radicals) thiene-3-yl, 3- (4- pyridine radicals) furans -2- bases, 4- (4- pyridine radicals) Furans -2- bases, 5- (4- pyridine radicals) furans -2- bases, 2- (4- pyridine radicals) furans -3- bases, 4- (4- pyridine radicals) furans -3- bases, 5- (4- pyridine radicals) furans -3- bases, 3- (4- pyridine radicals) benzothiophene -2- bases, 4- (4- pyridine radicals) benzothiophene -2- bases, 5- (4- pyridine radicals) benzothiophene -2- bases, 6- (4- pyridine radicals) benzothiophene -2- bases, 7- (4- pyridine radicals) benzothiophene -2- bases, 2- (4- pyridine radicals) benzothiophene -3- bases, 4- (4- pyridine radicals) benzothiophene -3- bases, 5- (4- pyridine radicals) benzothiophene -3- Base, 6- (4- pyridine radicals) benzothiophene -3- bases, 7- (4- pyridine radicals) benzothiophene -3- bases, 2- (4- pyridine radicals) benzothiophene - 4- bases, 3- (4- pyridine radicals) benzothiophene -4- bases, 5- (4- pyridine radicals) benzothiophene -4- bases, 6- (4- pyridine radicals) benzo thiophene Fen -4- bases, 7- (4- pyridine radicals) benzothiophene -4- bases, 2- (4- pyridine radicals) benzothiophene -5- bases, 3- (4- pyridine radicals) benzo Thiophene -5- bases, 4- (4- pyridine radicals) benzothiophene -5- bases, 6- (4- pyridine radicals) benzothiophene -5- bases, 7- (4- pyridine radicals) benzene Bithiophene -5- bases, 2- (4- pyridine radicals) benzothiophene -6- bases, 3- (4- pyridine radicals) benzothiophene -6- bases, 4- (4- pyridine radicals) Benzothiophene -6- bases, 5- (4- pyridine radicals) benzothiophene -6- bases, 7- (4- pyridine radicals) benzothiophene -6- bases, 2- (4- pyridines Base) benzothiophene -7- bases, 3- (4- pyridine radicals) benzothiophene -7- bases, 4- (4- pyridine radicals) benzothiophene -7- bases, 5- (4- pyrroles Piperidinyl) benzothiophene -7- bases, 6- (4- pyridine radicals) benzothiophene -7- bases, 3- (4- pyridine radicals) benzofuran -2- bases, 4- (4- Pyridine radicals) benzofuran -2- bases, 5- (4- pyridine radicals) benzofuran -2- bases, 6- (4- pyridine radicals) benzofuran -2- bases, 7- (4- pyridine radicals) benzofuran -2- bases, 2- (4- pyridine radicals) benzofuran -3- bases, 4- (4- pyridine radicals) benzofuran -3- bases, 5- (4- pyridine radicals) benzofuran -3- bases, 6- (4- pyridine radicals) benzofuran -3- bases, 7- (4- pyridine radicals) benzofuran -3- Base, 2- (4- pyridine radicals) benzofuran -4- bases, 3- (4- pyridine radicals) benzofuran -4- bases, 5- (4- pyridine radicals) benzofuran - 4- bases, 6- (4- pyridine radicals) benzofuran -4- bases, 7- (4- pyridine radicals) benzofuran -4- bases, 2- (4- pyridine radicals) benzo furan Mutter -5- bases, 3- (4- pyridine radicals) benzofuran -5- bases, 4- (4- pyridine radicals) benzofuran -5- bases, 6- (4- pyridine radicals) benzo Furans -5- bases, 7- (4- pyridine radicals) benzofuran -5- bases, 2- (4- pyridine radicals) benzofuran -6- bases, 3- (4- pyridine radicals) benzene And furans -6- bases, 4- (4- pyridine radicals) benzofuran -6- bases, 5- (4- pyridine radicals) benzofuran -6- bases, 7- (4- pyridine radicals) Benzofuran -6- bases, 2- (4- pyridine radicals) benzofuran -7- bases, 3- (4- pyridine radicals) benzofuran -7- bases, 4- (4- pyridines Base) benzofuran -7- bases, 5- (4- pyridine radicals) benzofuran -7- bases, 6- (4- pyridine radicals) benzofuran -7- bases, 2- (4- pyrroles Piperidinyl) dibenzothiophenes -1- bases, 3- (4- pyridine radicals) dibenzothiophenes -1- bases, 4- (4- pyridine radicals) dibenzothiophenes -1- bases, 6- (4- pyridine radicals) dibenzothiophenes -1- bases, 7- (4- pyridine radicals) dibenzothiophenes -1- bases, 8- (4- pyridine radicals) dibenzo thiophene Fen -1- bases, 9- (4- pyridine radicals) dibenzothiophenes -1- bases, 1- (4- pyridine radicals) dibenzothiophenes -2- bases, 3- (4- pyridine radicals) Dibenzothiophenes -2- bases, 4- (4- pyridine radicals) dibenzothiophenes -2- bases, 6- (4- pyridine radicals) dibenzothiophenes -2- bases, 7- (4- Pyridine radicals) dibenzothiophenes -2- bases, 8- (4- pyridine radicals) dibenzothiophenes -2- bases, 9- (4- pyridine radicals) dibenzothiophenes -2- Base, 1- (4- pyridine radicals) dibenzothiophenes -3- bases, 2- (4- pyridine radicals) dibenzothiophenes -3- bases, 4- (4- pyridine radicals) dibenzo Thiene-3-yl, 6- (4- pyridine radicals) dibenzothiophenes -3- bases, 7- (4- pyridine radicals) dibenzothiophenes -3- bases, 8- (4- pyridines Base) dibenzothiophenes -3- bases, 9- (4- pyridine radicals) dibenzothiophenes -3- bases, 2- (4- pyridine radicals) dibenzofurans -1- bases, 3- (4- pyridine radicals) dibenzofurans -1- bases, 4- (4- pyridine radicals) dibenzofurans -1- bases, 6- (4- pyridine radicals) dibenzofurans - 1- bases, 7- (4- pyridine radicals) dibenzofurans -1- bases, 8- (4- pyridine radicals) dibenzofurans -1- bases, 9- (4- pyridine radicals) hexichol And furans -1- bases, 1- (4- pyridine radicals) dibenzofurans -2- bases, 3- (4- pyridine radicals) dibenzofurans -2- bases, 4- (4- pyridines Base) dibenzofurans -2- bases, 6- (4- pyridine radicals) dibenzofurans -2- bases, 7- (4- pyridine radicals) dibenzofurans -2- bases, 8- (4- pyridine radicals) dibenzofurans -2- bases, 9- (4- pyridine radicals) dibenzofurans -2- bases, 1- (4- pyridine radicals) dibenzofurans - 3- bases, 2- (4- pyridine radicals) dibenzofurans -3- bases, 4- (4- pyridine radicals) dibenzofurans -3- bases, 6- (4- pyridine radicals) hexichol And furans -3- bases, 7- (4- pyridine radicals) dibenzofurans -3- bases, 8- (4- pyridine radicals) dibenzofurans -3- bases, 9- (4- pyridines Base) dibenzofurans -3- bases etc..In these substituents, from electron transporting material excellent aspect, preferred benzene Base, p-methylphenyl, biphenyl -3- bases, biphenyl -4- bases, 3- (1- naphthyls) phenyl, 3- (2- naphthyls) phenyl, 4- (1- naphthyls) phenyl, 4- (2- naphthyls) phenyl, 3- (9- phenanthryl) phenyl, 4- (9- phenanthryl) phenyl, 3- (fluoranthene -3- bases) phenyl, 4- (fluoranthene -3- bases) Phenyl, 3- (2- pyridine radicals) phenyl, 4- (2- pyridine radicals) phenyl, 3- (3- pyridine radicals) phenyl, 4- (3- pyridine radicals) phenyl, 3- (2- quinolyls) phenyl, 4- (2- quinolyls) phenyl, 3- (3- quinolyls) phenyl, 4- (3- quinolyls) phenyl, 3- (5- methyl thiazoliums Fen -2- bases) phenyl, 4- (5- methylthiophene -2- bases) phenyl, 3- (5- methylfuran -2- bases) phenyl, 4- (5- methylfuran -2- Base) phenyl, 3- (2- benzothienyls) phenyl, 4- (2- benzothienyls) phenyl, 3- (2- benzofuranyls) phenyl, 4- (2- Benzofuranyl) phenyl, 3- (2- dibenzothiophenes bases) phenyl, 4- (2- dibenzothiophenes bases) phenyl, 3- (4- dibenzothiophenes Base) phenyl, 4- (4- dibenzothiophenes bases) phenyl, 3- (2- dibenzofuran groups) phenyl, 4- (2- dibenzofuran groups) phenyl, 3- (4- dibenzofuran groups) phenyl, 4- (4- dibenzofuran groups) phenyl, 2- phenylpyridine -6- bases, 2- phenylpyridine -5- Base, 2- phenylpyridine -4- bases, 3- phenylpyridine -5- bases, 3- phenylpyridine -6- bases, 5- tolylthiophene -2- bases, 5- phenyl furans Mutter -2- bases, 1- naphthyls, 2- naphthyls, 2- benzothienyls, 2- benzofuranyls, 1- phenanthryl, 2- phenanthryl, 3- phenanthryl, 9- phenanthryl, 2- dibenzothiophenes bases, 2- dibenzofuran groups, 4- dibenzothiophenes base or 4- dibenzofuran groups, more preferably phenyl, connection Benzene -3- bases, biphenyl -4- bases, 3- (1- naphthyls) phenyl, 3- (2- naphthyls) phenyl, 4- (1- naphthyls) phenyl, 4- (2- naphthyls) benzene Base, 3- (9- phenanthryl) phenyl, 4- (9- phenanthryl) phenyl, 3- (fluoranthene -3- bases) phenyl, 4- (fluoranthene -3- bases) phenyl, 3- (2- pyrroles Piperidinyl) phenyl, 4- (2- pyridine radicals) phenyl, 3- (3- pyridine radicals) phenyl, 4- (3- pyridine radicals) phenyl, 3- (2- quinolyls) benzene Base, 4- (2- quinolyls) phenyl, 3- (3- quinolyls) phenyl, 4- (3- quinolyls) phenyl, 3- (2- benzothienyls) phenyl, 4- (2- benzothienyls) phenyl, 3- (2- benzofuranyls) phenyl, 4- (2- benzofuranyls) phenyl, 3- (2- dibenzothiophenes Base) phenyl, 4- (2- dibenzothiophenes bases) phenyl, 3- (4- dibenzothiophenes bases) phenyl, 4- (4- dibenzothiophenes bases) phenyl, 3- (2- dibenzofuran groups) phenyl, 4- (2- dibenzofuran groups) phenyl, 3- (4- dibenzofuran groups) phenyl, 4- (4- bis- Benzofuranyl) phenyl, 1- naphthyls, 2- naphthyls, 9- phenanthryl, 2- dibenzothiophenes bases, 2- dibenzofuran groups, 4- dibenzo thiophenes Fen base or 4- dibenzofuran groups etc..
In formula (1), R5、R6And R7The alkyl of carbon number 1～4 is represented independently of one another.
As R5、R6And R7In carbon number 1～4 alkyl, be not particularly limited, but as preference, can enumerate： Methyl, ethyl, propyl group, isopropyl, normal-butyl or tert-butyl group etc..In these substituents, from electron transporting material excellent Aspect set out, more preferably methyl.
In formula (1), n represents 0 or 1.
In formula (1), p represents 0,1,2,3 or 4.In the case that p is 2,3 or 4, R5Can also be different from each other.
In formula (1), q represents 0,1,2,3 or 4.In the case that q is 2,3 or 4, R6Can also be different from each other.
In formula (1), r represents 0,1 or 2.In the case that r is 2,2 R7Can also be different from each other.
With regard to p, q, r, from electron transporting material excellent aspect, 0 or 1 is preferably all independently of one another, More preferably all 0.
When this compound is used as a part for the constituent of organic electroluminescent device, can obtain high luminous Efficient activity, long lifetime, lower voltage and other effects.Particularly in the case where using as electron transfer layer, can notable earth's surface Reveal the effect.
In compound shown in formula (1), as the concrete example of particularly preferred compound, can example go out following (A- 1)～(A-1669), but the present invention is not limited to these compounds.
[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]
[chemical formula 11]
[chemical formula 12]
[chemical formula 13]
[chemical formula 14]
[chemical formula 15]
[chemical formula 16]
[chemical formula 17]
[chemical formula 18]
[chemical formula 19]
[chemical formula 20]
[chemical formula 21]
[chemical formula 22]
[chemical formula 23]
[chemical formula 24]
[chemical formula 25]
[chemical formula 26]
[chemical formula 27]
[chemical formula 28]
[chemical formula 29]
[chemical formula 30]
[chemical formula 31]
[chemical formula 32]
[chemical formula 33]
[chemical formula 34]
[chemical formula 35]
[chemical formula 36]
[chemical formula 37]
[chemical formula 38]
[chemical formula 39]
[chemical formula 40]
[chemical formula 41]
[chemical formula 42]
[chemical formula 43]
[chemical formula 44]
[chemical formula 45]
[chemical formula 46]
[chemical formula 47]
[chemical formula 48]
[chemical formula 49]
[chemical formula 50]
[chemical formula 51]
[chemical formula 52]
[chemical formula 53]
[chemical formula 54]
[chemical formula 55]
[chemical formula 56]
[chemical formula 57]
[chemical formula 58]
[chemical formula 59]
[chemical formula 60]
[chemical formula 61]
[chemical formula 62]
[chemical formula 63]
[chemical formula 64]
[chemical formula 65]
[chemical formula 66]
[chemical formula 67]
[chemical formula 68]
[chemical formula 69]
[chemical formula 70]
[chemical formula 71]
[chemical formula 72]
[chemical formula 73]
[chemical formula 74]
[chemical formula 75]
[chemical formula 76]
[chemical formula 77]
[chemical formula 78]
[chemical formula 79]
[chemical formula 80]
[chemical formula 81]
[chemical formula 82]
[chemical formula 83]
[chemical formula 84]
[chemical formula 85]
[chemical formula 86]
Hereinafter, illustrate for the purposes of triaizine compounds (1).
From broadly, the luminescent layer in organic electroluminescent device is referred to the electricity being made up of negative electrode and anode Irradiative layer during the circulating current of pole.Specifically, meeting when to the electrode flow electric current being made up of negative electrode and anode is referred to The luminous layer containing fluorescent compound.Generally, organic electroluminescent device is taken and luminescent layer is clamped between a pair of electrodes Structure.
The organic electroluminescent device of the present invention is taken and have beyond luminescent layer as desired hole transmission layer, electronics Transport layer, anode buffer layer and cathode buffer layer etc. and the structure clamped using negative electrode and anode.Specifically can enumerate following Shown structure.(i) anode/luminescent layer/negative electrode (ii) anode/hole transmission layer/luminescent layer/negative electrode (iii) anode/luminous Layer/electron transfer layer/negative electrode (iv) anode/hole transmission layer/luminescent layer/electron transfer layer/negative electrode (v) anode/anode buffer Layer/hole transmission layer/luminescent layer/electron transfer layer/cathode buffer layer/negative electrode.
Luminescent layer in the organic electroluminescent device of the present invention can use conventional known luminescent material.Send out as being formed The method of photosphere, the method including for example utilizing the known method such as vapour deposition method, spin-coating method, the tape casting, LB methods to form film.
In addition, the luminescent layer can be by forming molten by binding material co-dissolves such as luminescent material and resins in solvent After liquid, being coated with the solution using spin-coating method etc. carries out film formation and obtains.
For the thickness of such luminescent layer for being formed is not particularly limited, can according to circumstances and suitably select, but generally For the scope of 5nm～5 μm.
Hereinafter, combine with luminescent layer for hole injection layer, hole transmission layer, electron injecting layer, electron transfer layer etc. and Other layers for constituting organic electroluminescent device are illustrated.
Hole injection layer, hole transmission layer have will be transferred to the function of luminescent layer by anode injected holes, by making The hole injection layer, hole transmission layer are present between anode and luminescent layer, can be under lower electric field by substantial amounts of hole Injection luminescent layer.
In addition, transmitting electronics to luminescent layer because existing by negative electrode injection and by electron injecting layer and/or electron transfer layer In the barrier of the electronics at luminescent layer and hole injection layer or the interface of hole transmission layer, to the interface accumulation in luminescent layer not Hole injection layer or hole transmission layer can be leaked to, so as to form the excellent elements of luminescent properties such as luminous efficiency raising.
Above-mentioned hole-injecting material, hole mobile material be tool it is cuniculate injection or transmit, electronics it is barrier in Arbitrarily the material of function, can be any materials in organic matter, inorganic matter.As the hole-injecting material, hole transport material Material, can enumerate for example：Triazole derivative, oxadiazole derivatives, imdazole derivatives, polyaryl alkane derivatives, pyrazoline derive Thing and pyrazolone derivative, phenylenediamine derivative, arylamine derivatives, amino chalcones derivative, oxazole derivatives, Styrylanthracene derivatives, fluorenone derivatives, hydazone derivative, stilbene derivatives, silazane derivatives, aniline analog copolymer, or lead Electrical high-molecular oligomers thing, particularly thiophene oligomers etc..As hole-injecting material, hole mobile material, can use above-mentioned Material, but porphyrin compound, aromatic uncle amine compound and styrylamine compounds are preferably used, particularly preferably using fragrance Race's tertiary amine compound.
As above-mentioned aromatic uncle amine compound and the typical example of styrylamine compounds, can enumerate：N,N,N’,N’- Tetraphenyl -4,4 '-diamino-phenyl, N, N '-diphenyl-N, N '-bis- (3- aminomethyl phenyls)-[1,1 '-biphenyl] -4,4 '-diamines (TPD), double (the 4- di-p-tolyl aminophenyls) propane of 2,2-, 1,1- double (4- di-p-tolyl aminophenyls) hexamethylene, N, N, N ', double (4- di-p-tolyl the aminophenyls) -4- cyclohexylbenzenes of-the 4,4 '-benzidines of p-methylphenyl of N '-four, 1,1-, Double (4- dimethylamino -2- aminomethyl phenyls) phenylmethanes, double (4- di-p-tolyl aminophenyls) phenylmethanes, N, N '-two Phenyl-N, N '-two (4- methoxyphenyls) -4,4 '-benzidine, N, N, N ', N '-tetraphenyl -4,4 '-diamino-diphenyl Ether, 4,4 '-bis- (diphenyl amino) quaterphenyls, N, N, N- tri- (p-methylphenyl) amine, 4- (di-p-tolyl amino) -4 '-[4- (di-p-tolyl amino) styryl] stilbene, 4-N, N- diphenyl aminos-(2- diphenylacetylenes) benzene, 3- methoxyl groups -4 ' - N, N- diphenyl amino ス チ Le benzene, N- phenyl carbazoles, 4,4 '-bis- [N- (1- naphthyls)-N- phenyl aminos] biphenyl (NPD), 4, 4 ', 4 "-three [N- (3- aminomethyl phenyls)-N- phenyl aminos] triphenylamines (MTDATA) etc..
In addition, the inorganic compound such as p-type-Si, p-type-SiC can also make as hole-injecting material, hole mobile material With.The hole injection layer, hole transmission layer can be by the way that above-mentioned hole-injecting material, hole mobile material be steamed using such as vacuum Method known to plating method, spin-coating method, the tape casting, LB methods etc. carries out filming and is formed.With regard to hole injection layer, hole transmission layer Thickness, be not particularly limited, but usually 5nm～5 μm or so.The hole injection layer, hole transmission layer can be by above-mentioned One or more single layer structures for being formed in material, or by constituting or the multilayer for constituting not of the same race with same The laminated construction of composition.
In the organic electroluminescent device of the present invention, electron transfer layer is comprising the triazine shown in above-mentioned formula (1) The layer of compound.
The electron transfer layer can be by the triaizine compounds shown in above-mentioned formula (1) for example, by vacuum vapour deposition, spin coating Thin film forming method known to method, the tape casting, LB methods etc. carries out film forming and is formed.The thickness of electron transfer layer is not particularly limited, But select generally in the range of 5nm～5 μm.In addition, the electron transfer layer can include the triazine chemical combination shown in formula (1) Thing and comprising conventional known electron transport material, can be the single layer structure formed by one or more, or, Can be by constituting or laminated construction that the multilayer for constituting not of the same race is constituted with same.
In addition, in the present invention, luminescent material is not merely defined in luminescent layer, it is also possible to make the sky adjoined with luminescent layer Contain a kind of luminescent material in cave transport layer or electron transfer layer, thereby, it is possible to further improve sending out for organic electroluminescent device Light efficiency.
For with regard to being preferred for the substrate of the organic electroluminescent device of the present invention, glass, plastics are not particularly limited to Etc. species, as long as also, transparent substrate be then not particularly limited.As the organic electroluminescent for being preferably used for the present invention Element, can enumerate such as glass, quartz, translucency plastic foil.
As translucency plastic foil, can enumerate for example by polyethylene terephthalate (PET), poly- naphthalenedicarboxylic acid second two Alcohol ester (PEN), polyether sulfone (PES), PEI, polyether-ether-ketone, polyphenylene sulfide, polyarylate, polyimides, Merlon (PC), film of formation such as cellulose triacetate (TAC), cellulose-acetate propionate (CAP) etc..
Preference for making the organic electroluminescent device of the present invention is illustrated.As an example, for by above-mentioned The organic electroluminescence that formed of anode/hole injection layer/hole transmission layer/luminescent layer/electron transfer layer/electron injecting layer/negative electrode The facture of light-emitting component is illustrated.
First, on appropriate substrate in the way of reaching the thickness of less than 1 μm, preferably 10～200nm scope by steam The methods such as plating, sputtering form the film by made by desired electrode material, such as anode are with material and make anode.Then, It is formed on as element material comprising hole injection layer, hole transmission layer, luminescent layer, electron transfer layer/electron injection The film of layer.
It should be noted that can also make between anode and luminescent layer or hole injection layer and negative electrode and luminescent layer or There is cushion (sector electrode surface layer) between electron injecting layer.
Further, it is also possible to which as desired lamination has the layer of other functions beyond above-mentioned basic composition layer, for example, There can also be such functional layer such as hole blocking layer, electronic barrier layer.
Hereinafter, illustrate for the electrode of the organic electroluminescent device of the present invention.As organic electroluminescent device In anode, preferably use and be with the metal of work function big (more than 4eV), alloy, conductive compound and their mixture The anode of electrode substance.As the concrete example of such electrode substance, can enumerate the metals such as Au, CuI, indium oxide-tin (ITO), SnO2, the conductive clear material such as ZnO.
For above-mentioned anode, can form the film of these electrode substances and utilize photoetching by methods such as evaporation, sputterings Method and form the pattern of intended shape, or, it is also possible to evaporation, sputtering when pattern is formed via the mask of intended shape.
On the other hand, as negative electrode, preferably use with the metal of work function little (below 4eV) (referred to as electron injection gold Category), alloy, conductive compound and their mixture for electrode substance negative electrode.As the concrete of such electrode substance Example, can enumerate：Sodium, sodium-potassium-sodium alloy, magnesium, lithium, magnesium/copper mixture, magnesium/silver mixture, magnesium/aluminium mixture, magnesium/indium mixture, Aluminium/aluminum oxide (Al2O3) mixture, indium, lithium/aluminium mixture, rare earth metal etc..In these, from electron injection and relative to oxygen Set out in terms of the durability of change etc., preferred electronics injection metal is bigger than electronics injection metal with the value as work function The bimetallic mixture of stable metal, such as magnesium/silver mixture, magnesium/aluminium mixture, magnesium/indium mixture, aluminium/oxidation Aluminium (Al2O3) mixture, lithium/aluminium mixture etc..Above-mentioned negative electrode can be by utilizing the methods such as evaporation, sputtering by these electrode substances Form film and make.
As described above on appropriate substrate in the way of reaching the thickness of less than 1 μm, preferably 10～200nm scope The film formed by desired electrode material, such as anode material is formed by methods such as evaporation, sputterings and anode is made Afterwards, it is formed as described above on the anode comprising hole injection layer, hole transmission layer, luminescent layer, electron transfer layer/electronics Each layer film of implanted layer, then thereon to reach less than 1 μm, preferably 50～200nm of the thickness of scope in the way of pass through Such as method such as evaporation, sputtering forms the film by made by negative electrode material and arranges negative electrode, desired organic so as to be obtained Electroluminescent cell.
The organic electroluminescent device of the present invention can be used as illumination or a kind of lamp as exposure light source is used, Can be used as by the projection arrangement of the type of image projection, directly carry out the type of visuognosis to rest image, dynamic image Display device (display) and use.In the case of being used with display device as video playback, its type of drive can be Any-mode in simple matrix (passive matrix) mode or active matrix mode.In addition, there is difference by using two or more The organic electroluminescent device of the invention of illuminant colour, can make full-color display device.
Description of the drawings
The profile schema diagram of the single-layer element made in [Fig. 1] embodiment.
Symbol description
1. the glass substrate with ito transparent electrode
2. hole injection layer
3. charge generation layer
4. hole transmission layer
5. luminescent layer
6. electron transfer layer
7. cathode layer
Then, illustrate for the manufacture method of the present invention.
The triaizine compounds (1) of the present invention can presence or absence of under conditions of alkali, in the presence of palladium catalyst, Manufactured by the method shown in following reaction equation (11), reaction equation (12), reaction equation (21) or reaction equation (22).
[chemical formula 87]
(in reaction equation (11), Ar1、Ar2、Ar3、R5、R6、R7、p、q、r、Z1And Z2Expression takes with above-mentioned formula (1) identical Dai Ji.Y represents leaving group described later.M represents substituent described later.)
[chemical formula 88]
(in reaction equation (12), Ar1、Ar2、Ar3、R5、R6、R7、p、q、r、Z1And Z2Represent identical with above-mentioned formula (11) Substituent.Y represents leaving group described later.M represents substituent described later.)
[chemical formula 89]
(in reaction equation (21), Ar1、Ar2、Ar3、R5、R7、p、r、Z1And Z2Expression replaces with identical in above-mentioned formula (1) Base.Y represents leaving group described later.M represents substituent described later.)
[chemical formula 90]
(in reaction equation (22), Ar1、Ar2、Ar3、R5、R7、p、r、Z1And Z2Expression replaces with identical in above-mentioned formula (1) Base.Y represents leaving group described later.M represents substituent described later.).
In addition, it is following, with regard to the compound shown in formula (11), referred to as compound (11).With regard to other compounds, also adopt With synonymous.
M represents independently of one another ZnR1、MgR2、Sn(R3)3Or B (OR4)2.But wherein, R1And R2Chlorine is represented independently of one another Atom, bromine atoms or atomic iodine, R3Represent the alkyl or phenyl of carbon number 1～4, R4Represent hydrogen atom, carbon number 1～4 Alkyl or phenyl, B (OR4)2In 2 R4It is optionally identical or different.In addition, 2 R4Can also be integrally formed and former comprising oxygen Son and boron atom and form ring.
As ZnR1、MgR2, can enumerate：ZnCl, ZnBr, ZnI, MgCl, MgBr, MgI etc..
As Sn (R3)3, can enumerate：Sn(Me)3、Sn(Bu)3Deng.
As B (OR4)2, can enumerate：B(OH)2、B(OMe)2、B(OiPr)2、B(OBu)2Deng.In addition, as 2 R4Become One simultaneously forms the B (OR in the case of ring comprising oxygen atom and boron atom4)2Example, following (C-1)～(C- can be enumerated 6) group shown in, from the good aspect of yield, the preferably group shown in (C-2).
[chemical formula 91]
Compound (15), reaction equation (21) used in compound (13), reaction equation (12) used in reaction equation (11) Used in compound (23) and the compound (25) used in reaction equation (22) can be by such as Japanese Unexamined Patent Publication 2005- No. 268199 report [0105]～[0121], Japanese Unexamined Patent Publication 2008-280330 publications [0061]～[0076] or Japanese Unexamined Patent Publications Combination of Methods disclosed in 2001-335516 publications [0047]～[0082] and manufacture.As compound (13) and compound (23) following (B-1)～(B-56), can be enumerated, but the present invention is not limited to these.
[chemical formula 92]
[chemical formula 93]
[chemical formula 94]
[chemical formula 95]
[chemical formula 96]
[chemical formula 97]
The compound (25) used in compound (15) and reaction equation (22) used in reaction equation (12) can be enumerated will be upper The M for stating compound (13) and compound (23) replaces with the compound of Y.
The Y of compound (12), compound (15), compound (22) and compound (25) represents leaving group, not special Limit, such as chlorine atom, bromine atoms, atomic iodine or TFMS root etc. can be enumerated.Wherein, from reaction yield it is good in terms of Set out, preferred bromine atoms or chlorine atom.But consider from the availability of raw material, also sometimes preferably using the feelings of TFMS root Condition.
Then, illustrate for reaction equation (11)." operation 11 " makes compound (12) presence or absence of alkali Under the conditions of, in the presence of palladium catalyst with compound (13) react and obtain the present invention triaizine compounds (11) method, Can be by being coupled instead using Suzuki-palace Pu reaction, the reaction of root bank, bear field-jade end reaction, Stille (Shi Dile) reactions etc. are conventional The reaction condition answered and obtain object in high yield.
As palladium bichloride, acid chloride, palladium trifluoroacetate, nitre can be enumerated in the palladium catalyst used in " operation 11 " The salt such as sour palladium.Additionally, can enumerate：It is π-allyl palladium chloride dimer, palladium acetylacetonate, three (dibenzalacetone) two palladium, double The complex compounds such as (triphenylphosphine) palladium chloride, tetrakis triphenylphosphine palladium and (1,1 '-bis- (diphenylphosphine) ferrocene) palladium chloride. Wherein, from the aspect that reaction yield is good, further preferably there is palladium complex of the tertiary phosphine as part, from acquisition Easily, the good aspect of reaction yield is set out, and particularly preferably has palladium complex of the triphenylphosphine as part.
Can also add tertiary phosphine in palladium salt or complex compound as the palladium complex of part with tertiary phosphine, in reactant Prepare in system.As the tertiary phosphine that can be used at this moment, can enumerate：Triphenylphosphine, trimethyl-phosphine, tributylphosphine, tri-tert Double (diphenylphosphine) xanthenes of phosphine, tricyclohexyl phosphine, tert-butyl diphenyl phosphine, 9,9- dimethyl -4,5-, 2- (diphenylphosphine) -2 ' - (N, N- dimethylamino) biphenyl, 2- (di-t-butyl phosphine) biphenyl, 2- (dicyclohexylphosphontetrafluoroborate) biphenyl, double (diphenylphosphine) methane, Double (diphenylphosphine) ethane of 1,2-, double (diphenylphosphine) propane of 1,3-, 1,4- double (diphenylphosphine) butane, 1,1 '-bis- (diphenyl Phosphine) ferrocene, three (2- furyls) phosphines, three (o-tolyl) phosphines, three (2,5- xylyls) phosphines, (±) -2,2 '-bis- (hexichol Base phosphine) -1,1 '-dinaphthalene, 2- dicyclohexylphosphontetrafluoroborates -2 ', 4 ', 6 '-tri isopropyl biphenyl etc..From obtaining, easy, reaction yield is good Aspect set out, preferred 2- dicyclohexylphosphontetrafluoroborates -2 ', 4 ', 6 '-tri isopropyl biphenyl or triphenylphosphine.Tertiary phosphine and palladium salt or complexing The mol ratio of thing is preferably 1:10～10:1, from the good aspect of reaction yield, more preferably 1:2～5:1.
As be able to can enumerate in the alkali used in " operation 11 "：NaOH, potassium hydroxide, sodium carbonate, potassium carbonate, Lithium carbonate, cesium carbonate, potassium phosphate, sodium phosphate, sodium fluoride, potassium fluoride, cesium fluoride etc., from the good aspect of yield, preferably Potassium carbonate.Alkali is preferably 1 with the mol ratio of compound (13):2～10:1, from the good aspect of yield, further preferably For 1:1～3:1.
Compound (12) used in " operation 11 " is preferably 1 with the mol ratio of compound (13):2～5:1, from yield Good aspect is set out, and more preferably 1:2～2:1.
As be able to can enumerate in the solvent used in " operation 11 "：Water, dimethyl sulfoxide, dimethylformamide, tetrahydrochysene furan Mutter, Isosorbide-5-Nitrae-dioxane, dimethoxy-ethane, toluene, benzene, ether, ethanol, methyl alcohol or dimethylbenzene etc., it is also possible to by this A little solvent combinations are used.From the good aspect of yield, the mixing of dioxane or tetrahydrofuran and water is preferably used Solvent.
" operation 11 " can between 0 DEG C～150 DEG C it is appropriate select at a temperature of implement, from yield it is good in terms of go out Send out, further preferably carry out at 50 DEG C～100 DEG C.
Compound (11) can be obtained by carrying out common process after " operation 11 " terminates.Can also lead to as needed Cross recrystallization, column chromatography or distillation etc. and purified.
" operation 12 " can be adopted in the condition enumerated in " operation 11 ", and compound (12) is replaced with into compound (15) And compound (13) is replaced with into the condition of compound (14).
" operation 21 " can be adopted in the condition enumerated in " operation 11 ", and compound (12) is replaced with into compound (22) And compound (13) is replaced with into the condition of compound (23).
" operation 22 " can be adopted in the condition enumerated in " operation 11 ", and compound (12) is replaced with into compound (25) And compound (13) is replaced with into the condition of compound (24).
It should be noted that they need not be respectively and " operation 11 " identical reaction condition.Can also be in " operation 12 " after, " operation 21 " and " operation 22 " terminates, purified as desired by recrystallization, column chromatography or distillation etc..
The triaizine compounds (1) of the present invention can also be manufactured using the compound shown in formula (26).
[chemical formula 98]
(in formula (26),
Z3、Z4And Z5Nitrogen-atoms or C-H are represented independently of one another.Also, Z3、Z4And Z5In any one represent that nitrogen is former Son, remaining both expression C-H.
X1And X2Chlorine atom, bromine atoms or atomic iodine are represented independently of one another.Also, X1And X2It is former for bromine when both are different Son.)
That is, triaizine compounds (1) of the invention can be under conditions of presence or absence of alkali, in the presence of palladium catalyst Under, manufactured by the method shown in following reaction equation (23), reaction equation (24), reaction equation (25).
[chemical formula 99]
(in reaction equation (23), Ar1Represent substituent same as described above.
Ar4The carbon for represent the optional link of carbon number 6～18 and/or the aromatic hydrocarbyl of condensed ring, being only made up of 6 yuan of rings The optional link of atomicity 3～19 and/or the nitrogenous heteroaromatic group of condensed ring, comprising the atom group selected from H, C, O and S composition In atom carbon number 3～19 optional link and/or the heteroaromatic group of condensed ring (these substituents are optionally former by fluorine The alkoxyl of son, the alkyl of carbon number 1～4 or carbon number 1～4 replaces) or hydrogen atom.
Z3、Z4And Z5Nitrogen-atoms or C-H are represented independently of one another.Also, Z3、Z4And Z5In any one represent that nitrogen is former Son, remaining both expression C-H.
X1And X2Chlorine atom, bromine atoms or atomic iodine are represented independently of one another.Also, X1And X2It is former for bromine when both are different Son.
M1And M2Represent independently of one another and above-mentioned M identicals substituent.)
[chemical formula 100]
(in reaction equation (24), Ar1、Ar4、Z3、Z4、Z5、X1、X2、M1And M2Represent same as described above independently of one another to take Dai Ji.)
[chemical formula 101]
(in reaction equation (25), Ar1、Ar4、Y、Z3、Z4、Z5、X2、M1And M2Replacement same as described above is represented independently of one another Base.).
Further, triaizine compounds (1) of the invention can be under conditions of presence or absence of alkali, in palladium catalyst In the presence of, manufactured by the method shown in reaction equation (26), reaction equation (27) or reaction equation (28).
[chemical formula 102]
(in reaction equation (26), Ar1、Ar4、Y、Z3、Z4、Z5、X1、M1And M2Replacement same as described above is represented independently of one another Base.)
[chemical formula 103]
(in reaction equation (27), Ar1、Ar4、Y、Z3、Z4、Z5And M1Substituent same as described above is represented independently of one another.)
[chemical formula 104]
(in reaction equation (28), Ar1、Ar4、Y、Z3、Z4、Z5And M2Replacement same as described above is represented independently of one another Base.).
X1And X2Chlorine atom, bromine atoms or atomic iodine are represented independently of one another.Also, X1And X2It is former for bromine when both are different Son.Wherein, from the aspect that reaction yield is good, preferred bromine atoms or chlorine atom.In addition, in order that the selectivity of reaction is carried Height, further preferred X1And X2With different atoms.
As compound (26), following (C-1)～(C-64) can be enumerated, but the present invention is not limited to these chemical combination Thing.
[chemical formula 105]
[chemical formula 106]
[chemical formula 107]
[chemical formula 108]
In reaction equation (23), reaction equation (24), reaction equation (25), reaction equation (26), reaction equation (27) and reaction equation (28) Ar4The carbon number for represent the optional link of carbon number 6～18 and/or the aromatic hydrocarbyl of condensed ring, being only made up of 6 yuan of rings 3～19 optional link and/or the nitrogenous heteroaromatic group of condensed ring or comprising in the atom group selected from H, C, O and S composition The optional link of the carbon number 3～19 of atom and/or condensed ring heteroaromatic group (these substituents can also by fluorine atom, The alkyl of carbon number 1～4, the alkoxyl of carbon number 1～4 replace) or hydrogen atom.
As Ar4Concrete example, be not particularly limited, can enumerate with Ar2Those identicals of middle specific example replace Base.But do not include the carbon original that carbon number is more than 18 optional link and/or the aromatic hydrocarbyl of condensed ring, is only made up of 6 yuan of rings Subnumber is more than 20 optional link and/or the nitrogenous heteroaromatic group of condensed ring or comprising the atom selected from H, C, O and S composition (these substituents are optionally by fluorine for the heteroaromatic group of optional link and/or condensed ring of the carbon number of the atom in group more than 20 The alkoxyl of atom, the alkyl of carbon number 1～4 or carbon number 1～4 replaces).
By according to reaction equation (23), reaction equation (24), reaction equation (25), reaction equation (26), reaction equation (27) and reaction Formula (28), by conventional coupling reactions such as Suzuki-palace Pu reaction, the reaction of root bank, bear field-jade end reaction, Stille reactions one is adopted As condition and implement necessary number of times, can in high yield obtain object.
" operation 23 " can be adopted in the condition enumerated in " operation 21 ", and compound (22) is replaced with into compound (26) And compound (23) is replaced with into the condition of compound (28).But need not be and " operation 21 " identical reaction condition.Also may be used After " operation 23 " terminates, to be purified as desired by recrystallization, column chromatography or distillation etc..
" operation 24 " can be adopted in the condition enumerated in " operation 21 ", and compound (22) is replaced with into compound (29) And compound (23) is replaced with into the condition of compound (30).But need not be and " operation 21 " identical reaction condition.Also may be used After " operation 24 " terminates, to be purified as desired by recrystallization, column chromatography or distillation etc..
" operation 25 " can be adopted in the condition enumerated in " operation 21 ", and compound (22) is replaced with into compound (26) And compound (23) is replaced with into the condition of compound (30).But need not be and " operation 21 " identical reaction condition.Also may be used After " operation 25 " terminates, to be purified as desired by recrystallization, column chromatography or distillation etc..
" operation 26 " can be adopted in the condition enumerated in " operation 21 ", and compound (22) is replaced with into compound (32) And compound (23) is replaced with into the condition of compound (28).But need not be and " operation 21 " identical reaction condition.Also may be used After " operation 26 " terminates, to be purified as desired by recrystallization, column chromatography or distillation etc..
" operation 27 " can be adopted in the condition enumerated in " operation 21 ", and compound (23) is replaced with into compound (33) Condition.But need not be and " operation 21 " identical reaction condition.Can also after " operation 27 " terminates, as desired by Recrystallization, column chromatography or distillation etc. and purified.
" operation 28 " can be adopted in the condition enumerated in " operation 21 ", and compound (22) is replaced with into compound (29) And compound (23) is replaced with into the condition of compound (30).But need not be and " operation 21 " identical reaction condition.Also may be used After " operation 28 " terminates, to be purified as desired by recrystallization, column chromatography or distillation etc..
" operation 29 " can be adopted in the condition enumerated in " operation 21 ", and compound (22) is replaced with into compound (35) And compound (23) is replaced with into the condition of compound (34).But need not be and " operation 21 " identical reaction condition.Also may be used After " operation 29 " terminates, to be purified as desired by recrystallization, column chromatography or distillation etc..
" operation 30 " can be adopted in the condition enumerated in " operation 21 ", and compound (22) is replaced with into compound (32) And compound (23) is replaced with into the condition of compound (28).But need not be and " operation 21 " identical reaction condition.Also may be used After " operation 30 " terminates, to be purified as desired by recrystallization, column chromatography or distillation etc..
" operation 31 " can be adopted in the condition enumerated in " operation 21 ", and compound (23) is replaced with into compound (36) Condition.But need not be and " operation 21 " identical reaction condition.Can also after " operation 31 " terminates, as desired by Recrystallization, column chromatography or distillation etc. and purified.
" operation 32 " can be adopted in the condition enumerated in " operation 21 ", and compound (22) is replaced with into compound (35) And compound (23) is replaced with into the condition of compound (37).But need not be and " operation 21 " identical reaction condition.Also may be used After " operation 32 " terminates, to be purified as desired by recrystallization, column chromatography or distillation etc..
The triaizine compounds (1) of the present invention are the compounds for being suitable for use as material for organic electroluminescence device.
Further, triaizine compounds (1) of the invention are the electric transmission materials for being suitable for use as organic electroluminescent device The compound of material or electron injection material.
The present invention triaizine compounds (1) be when a part for the constituent as organic electroluminescent device is used Effectively.Particularly when using as electron transfer layer, compared with traditional element, long lifetime, high efficiency can be obtained And lower voltage and other effects.In addition, when by the triaizine compounds (11) of the present invention as material for organic electroluminescence device, Can also make and be used with the common evaporation film of arbitrary organic metal kind, organic compound or inorganic compound.
The manufacture method of organic electroluminescent device film is not special by made by the triaizine compounds (1) of the present invention Limit, can be using vacuum vapour deposition come film forming.Can be by using general vacuum deposition apparatus using the film forming of vacuum vapour deposition Come carry out.If in view of manufacture intermittent time, manufacturing cost that organic electroluminescent device makes, being formed using vacuum vapour deposition The vacuum of vacuum tank during film is preferably capable 1 reached by conventional use of diffusion pump, turbomolecular pump, cryogenic pump etc. ×10-2～1 × 10-5～1 × 10-6Pa or so, more preferably 1 × 10-3～10-6Pa.Evaporation rate is according to the film to be formed Thickness and different, but preferably 0.005～1.0nm/ seconds, more preferably 0.01～1nm/ seconds.In addition, the triaizine compounds of the present invention And (1) is due in chloroform, dichloromethane, 1,2- dichloroethanes, chlorobenzene, toluene, ethyl acetate or tetrahydrofuran etc. (11) Solubility is high, therefore can also be using spin-coating method, ink-jet method, the tape casting or infusion process for having used fexible unit etc. come film forming.
As the typical structure of the organic electroluminescent device of the effect that can obtain the present invention, comprising substrate, anode, hole Implanted layer, hole transmission layer, luminescent layer, electron transfer layer and negative electrode.
The anode and negative electrode of organic electroluminescent device is connected via the conductor of electrical resistance with power supply.By to anode and the moon Apply current potential between pole, organic electroluminescent device is started.Hole is injected in organic electroluminescent device from anode, in addition, Electronics is injected with electro-luminescence element in negative electrode.
In typical case, organic electroluminescent device is covered by substrate, and male or female can be contacted with substrate.It is convenient For the sake of, by the referred to as lower lateral electrode of the electrode contacted with substrate.In general, lower lateral electrode is anode, but in the organic of the present invention In electroluminescent cell, such embodiment is not limited to.According to desired light emission direction, substrate can be made to be translucency Or it is opaque.Light transmission features are preferred for electroluminescent is watched through substrate.As such substrate, generally adopt It is clear glass or plastics.Substrate can be the composite construction comprising multilayer material layer.
In the case of through anode viewing electroluminescent, anode should make the luminous transmission or substantially pass through.The present invention Used in common transparent positive pole (anode) material be indium-tin-oxide (ITO), indium-zinc oxide (IZO) or tin oxide, But other metal oxidations, such as aluminium or indium doping type tin oxide, magnesium-indium oxide or nickel-tungsten oxide are also useful. In addition to these oxides, metal nitride, such as gallium nitride, metal selenide, such as zinc selenide, or gold can also be used Category sulfide, such as zinc sulphide are used as anode.For anode, it is possible to use have passed through plasma evaporation fluorocarbons and It is modified.For when watching electroluminescent purposes for negative electrode is only transmitted, the transmission characteristic of anode is unimportant, Can be using transparent, opaque or reflexive arbitrary conductive material.As one of the conductor for the purposes, can arrange Lift gold, iridium, molybdenum, palladium and platinum.
Hole injection layer can be set between anode and hole transmission layer.Hole-injecting material can aid in after improvement The film Formation and characteristics of continuous organic layer so make into hole transmission layer inject hole become easy.As be suitable to hole note Enter one of the material used in layer, porphyrin compound, plasma evaporation type fluorocarbon polymer can be enumerated and with biphenyl The amine of the aromatic rings such as base, carbazyl, such as m-MTDATA (4,4 ', 4 "-three [(3- aminomethyl phenyls) phenyl amino] triphenylamines), 2T-NATA (4,4 ', 4 "-three [(N- naphthalene -2- bases)-N- phenyl aminos] triphenylamines), triphenylamine, trimethylphenyl amine, toluene Base diphenylamine, N, N '-diphenyl-N, N '-bis- (3- aminomethyl phenyls) -1,1 '-biphenyl -4,4 '-diamines, N, N, the N ' N (4- of '-four Aminomethyl phenyl) -1,1 '-biphenyl -4,4 '-diamines, MeO-TPD (N, N, N ' N '-four (4- methoxyphenyls) -1,1 '-biphenyl -4, 4 '-diamines), N, N '-diphenyl-N, N '-dinaphthyl -1,1 '-biphenyl -4,4 '-diamines, N, N '-bis- (aminomethyl phenyl)-N, N ' - Double (4- n-butylphenyls) phenanthrene -9,10- diamines or N, N '-diphenyl-N, N '-bis- (9- phenyl carbazole -3- bases) -1,1 '-connection Benzene -4,4 '-diamines etc..
The hole transmission layer of organic electroluminescent device preferably comprises more than a kind of hole transport compound, such as fragrance Race's tertiary amine.Aromatic nitrile base refers to the compound containing more than 1 trivalent nitrogen atom, and the trivalent nitrogen atom is only tied with carbon atom Close, 1 in these carbon atoms aromatic ring formed above.Specifically, aromatic nitrile base can be arylamine, such as Dan Fang Base amine, diaryl amine, triarylamine or macromolecule arylamine.
As hole mobile material, it is possible to use the aromatic nitrile base with more than 1 amido.Further, it is possible to use High-molecular hole conduction material.It is, for example possible to use poly- (N- VCzs) (PVK), polythiophene, polypyrrole or polyaniline Deng.Can enumerate for example：NPD (N, N '-bis- (naphthalene -1- bases)-N, N '-diphenyl -1,1 '-biphenyl -4,4 '-diamines), α-NPD (N, N '-two (1- naphthyls)-N, N '-diphenyl -1,1 '-biphenyl -4,4 '-diamines), the TPBi ((1- phenyl -1H- benzo miaows of 1,3,5- tri- Azoles -2- bases) benzene) or TPD (N, N '-bis- (3- aminomethyl phenyls)-N, N '-diphenyl -1,1 '-biphenyl -4,4 '-diamines) etc..
Can also be provided as between hole injection layer and hole transmission layer charge generation layer comprising 2,3,6,7,10, The layer of the azepine triphenylenes (HAT-CN) of six cyano group -1,4,5,8,9,12- of 11- six.
The luminescent layer of organic electroluminescent device includes phosphor material or fluorescent material, now, as in region generation Electron-hole pair in conjunction with result, can produce luminous.Luminescent layer can be by the list comprising both low molecule and polymer One material is formed, but more generally situation is, is formed by the material of main part doped with guest compound, now, light it is main by Dopant causes, and it is possible to have arbitrary color.
As the material of main part of luminescent layer, can enumerate for example have xenyl, fluorenyl, triphenyl-silyl, carbazyl, The compound of pyrenyl or anthryl.Can enumerate for example：DPVBi (4,4 '-bis- (2,2- diphenylacetylenes) -1,1 '-biphenyl), BCzVBi (4,4 '-bis- (9- ethyl -3- carbazole vinyl) 1,1 '-biphenyl), TBADN (the 2- tert-butyl groups -9,10- two (2- naphthyls) Anthracene), AND (9,10- bis- (2- naphthyls) anthracene), CBP (4,4 '-bis- (carbazole -9- bases) biphenyl), CDBP (4,4 '-bis- (carbazole -9- Base) -2,2 '-dimethyl diphenyl) or double (biphenyl) anthracenes of 9,10- etc..
Material of main part in luminescent layer can be the electron transport material of following definitions, hole transport material defined above Material or support hole-electron in conjunction with other materials or these materials combination.
As one of useful fluorescent dopants, can enumerate：If anthracene, aphthacene, xanthene, perylenes, rubrene, cumarin, Red bright and quinacridone, dicyanomethylene pyran compound, thiapyrilium compounds, polymethine compounds, pyrans or thiapyran Compound, fluorene derivative, two Yin Bing perylene derivatives, Yin Bing perylene derivatives, double (azine) amine boron compounds, double (azine) first Hydride compounds and quinolone compounds etc..
As one of useful phosphorescent dopants, can enumerate：The organometallic ligand of the transition metal such as iridium, platinum, palladium or osmium Position compound.
As one of dopant, can enumerate：Alq3(three (8-hydroxyquinoline) aluminium)), DPAVBi (4,4 '-bis- [4- (two P-methylphenyl amino) styryl] biphenyl), perylenes, Ir (PPy)3(three (2- phenylpyridines) iridium (III) or FlrPic (double (3, Fluoro- 2- (2- pyridine radicals) phenyl of 5- bis--(2- carboxyl pyridine bases) iridium (III) etc..
Thin film formation material for forming the electron transfer layer of the organic electroluminescent device of the present invention is of the invention Triaizine compounds (1).It should be noted that the electron transfer layer can also include other electron transporting materials, as the electricity Sub- transporting material, can enumerate alkali metal coordination compound, alkaline-earth metal complex, rare earth metal complex etc.. As preferred alkali metal coordination compound, alkaline-earth metal complex, rare earth metal complex, can enumerate for example： 8-hydroxyquinoline lithium (Liq), double (8-hydroxyquinoline) zinc, double (8-hydroxyquinoline) copper, double (8-hydroxyquinoline) manganese, three (8- hydroxyls Base quinoline) aluminium, three (2- methyl -8-hydroxyquinoline) aluminium, three (8-hydroxyquinoline) galliums, double (10- hydroxy benzos [h] quinoline) berylliums, Double (10- hydroxy benzos [h] quinoline) zinc, double (2- methyl -8- quinoline) Network ロ ロ galliums, double (2- methyl -8- quinoline) (orthoresols) Gallium, double (2- methyl -8- quinoline) -1- naphthols aluminium or double (2- methyl -8- quinoline)-beta naphthal galliums etc..
For the purpose for improving carrier balance, it is also possible to arrange hole between luminescent layer and electron transfer layer and prevent Layer.As hole trapping layer, preferred compound can be enumerated：BCP (2,9- dimethyl -4,7- diphenyl -1,10- phenanthroline), Bphen (4,7- diphenyl -1,10- phenanthroline), BAlq (double (2- methyl -8-hydroxyquinoline) -4- (xenol conjunction) aluminium) or Double (10- hydroxy benzos [h] quinoline) berylliums) etc..
For raising electron injection, improve element characteristic (for example, luminous efficiency, low voltage drive or high-durability) Purpose, it is also possible to which electron injecting layer is set in the organic electroluminescent device of the present invention.
As the compound preferably as electron injecting layer, can enumerate：Fluorenone, anthraquinone bismethane, diphenoquinone, thiapyran dioxy Compound, oxazole, oxadiazoles, triazole, imidazoles, perylene tetracarboxylic acids, double methyl fluorenes, anthraquinone bismethane or anthrone etc..Alternatively, it is also possible to Using metal complex, alkali metal oxide, alkaline earth oxide, rare-earth oxide, alkali described in above-mentioned Metal halide, alkaline-earth halide, rare earth metal halide, SiOX、AlOX、SiNX、SiON、AlON、GeOX、LiOX、 LiON、TiOX、TiON、TaOX、TaON、TaNX, the inorganic compound as various oxides, nitride and nitrogen oxides such as C.
Only transmit anode viewing it is luminous in the case of, the negative electrode used in the present invention substantially can be by arbitrary electric conductivity Material is formed.As preferred cathode material, can enumerate：Sodium, sodium-potassium-sodium alloy, magnesium, lithium, magnesium/copper mixture, magnesium/silver mixing Thing, magnesium/aluminium mixture, magnesium/indium mixture, aluminium/aluminum oxide (Al2O3) mixture, indium, lithium/aluminium mixture, rare earth metal etc..
Embodiment
Hereinafter, the present invention is described in more detail in conjunction with the embodiments, but the explanation of the present invention does not receive completely these The restriction of embodiment.
1H-NMR is determined and carried out using Gemini200 (Varian company systems).
For the characteristics of luminescence of organic electroluminescent device, apply DC current to made element at room temperature, and Evaluated using the luminance meter of LUMINANCEMETER (BM-9) (TOPCON company systems).
Synthesis example -1
[chemical formula 109]
By 4- bromobenzaldehydes (3.00g, 0.0162mol), 2 acetyl naphthalene (2.78g, 0.0163mol) in air atmosphere Acetic acid (32.4mL) is dissolved in, the concentrated sulfuric acid (4.5mL, 0.0811mol) is added dropwise, and carried out at room temperature 2 hours stirring.Stirring Afterwards, 50mL water is added, the solid of precipitation is collected by filtration.Gained solid is washed with water (50mL), methyl alcohol (50mL), thus The red and white solid (receipts amount 3.32g, yield 74%) of 3- (4- bromophenyls) -1- (2- naphthyls) propenone of target is obtained.
Synthesis example -2
[chemical formula 110]
By 3- (4- bromophenyls) -1- (2- naphthyls) propenone (3.03g, 8.99mmol), 1- benzoyls in air atmosphere Methyl bromopyridine (3.75g, 0.0135mol), ammonium acetate (13.76g, 0.179mol) are suspended in acetic acid (90mL) and dimethyl methyl The mixed solvent of acid amides (90mL), has carried out 13 hours stirring in 150 DEG C.After naturally cooling to room temperature, water (100mL) is added, The solid of precipitation is collected by filtration.Gained solid is washed with water (100mL), 4- (the 4- bromobenzenes of target are resulting in Base) -2- (2- naphthyls) -6- phenylpyridines brown solid (receipts amount 3.11g, yield 80%).
Synthesis example -3
[chemical formula 111]
4- (4- bromophenyls) -2- (2- naphthyls) -6- phenylpyridines (2.5g, 5.73mmol) is dissolved in into four in argon gas stream Hydrogen furans (50mL), has carried out 20 minutes stirring in -78 DEG C.N-BuLi (hexane solution, 7.38mmol) is added dropwise thereto, And carried out 2 hours stirring.Then, add triisopropyl borate ester (1.70mL, 7.41mmol) and carried out 16 hours stirring.Stir After mixing, the sodium hydrate aqueous solution (4mL, 16.0mmol) of 4M is added, and carried out 1 hour stirring.Add in the reaction solution Enter water (50mL), and extracted using ethyl acetate (100mL).Organic layer is washed using saturated sodium-chloride water solution, will Organic layer and water layer are separated.After being dehydrated to organic layer using magnesium sulfate, from organic layer reduced pressure concentration low boiling point component is gone out, Resulting in 4- [2- (2- the naphthyls) -6- phenylpyridine -4- bases] phenylboric acid of target faint yellow solid (receipts amount 1.81g, Yield 79%).
Embodiment -1
[chemical formula 112]
By 4- [2- (2- naphthyls) -6- phenylpyridine -4- bases] phenylboric acid (1.60g, 3.99mmol), 2- in argon gas stream (3- bromophenyls) -4,6- diphenyl -1,3,5- triazines (1.13g, 2.93mmol), tetrakis triphenylphosphine palladium (0.104g, 0.09mmol) it is suspended in tetrahydrofuran (50mL).The wet chemical (4.4mL, 8.80mmol) of 2M is added thereto to, in 80 DEG C carry out 22 hours stirring.After naturally cooling to room temperature, water (80mL), methyl alcohol (20mL) are added, consolidating for precipitation is collected by filtration Body, and solid is washed using water (50mL), methyl alcohol (50mL), hexane (50mL).The solid dissolving is made in toluene (300mL) and diatomite filtration is carried out, reduced pressure concentration is carried out to filtrate, resulting in crude product.Gained crude product is passed through Recrystallization (toluene) purified, resulting in target 2- 4 '-[2- (2- naphthyls) -6- phenylpyridine -4- bases] biphenyl - 3- yls } -4,6- diphenyl -1,3,5- triazines (compound A-2) white powder (receipts amount 1.41g, yield 73%).
1H-NMR(CDCl3)δ(ppm):7.48-7.65 (m, 11H), 7.72 (t, J=7.6Hz, 1H), 7.90-8.05 (m, 9H), 8.15 (dd, J=1.4Hz, 1H), 8.27-8.31 (m, 2H), 8.39-8.43 (dd, J=8.3Hz, 1H), 8.71 (brs, 1H), 8.80-8.85 (m, 5H), 9.09 (t, J=1.6Hz, 1H).
The Tg of gained compound A-2 is 112 DEG C.
Synthesis example -4
[chemical formula 113]
It is in air atmosphere that 2- naphthaldehydes (3.01g, 0.0193mol), 4- bromoacetophenones (3.83g, 0.0192mol) is molten Solution is added dropwise the concentrated sulfuric acid (5.3mL, 0.0960mol) in acetic acid (38mL), and has carried out at room temperature 2 hours stirring.After stirring, 50mL water is added, the solid of precipitation is collected by filtration.Gained solid is washed with water (50mL), methyl alcohol (50mL), thus The yellow solid (receipts amount 4.08g, yield 63%) of 1- (4- bromophenyls) -3- (2- naphthyls) propenone of target is arrived.
Synthesis example -5
[chemical formula 114]
By 1- (4- bromophenyls) -3- (2- naphthyls) propenone (3.00g, 8.89mmol), 1- benzoyls in air atmosphere Methyl bromopyridine (3.73g, 0.0134mol), ammonium acetate (13.67g, 0.177mol) are suspended in acetic acid (90mL), dimethyl methyl The mixed solvent of acid amides (90mL), has carried out 15 hours stirring in 150 DEG C.After naturally cooling to room temperature, the water of 100mL is added, The solid of precipitation is collected by filtration.Gained solid is washed with water (100mL), 2- (the 4- bromobenzenes of target are resulting in Base) -4- (2- naphthyls) -6- phenylpyridines brown solid (receipts amount 2.96g, yield 76%).
Synthesis example -6
[chemical formula 115]
2- (4- bromophenyls) -4- (2- naphthyls) -6- phenylpyridines (2.20g, 5.04mmol) is dissolved in argon gas stream Tetrahydrofuran (50mL), is stirred in -78 DEG C.N-BuLi (hexane solution, 6.55mmol) is added dropwise thereto, is gone forward side by side Stirring in 1 hour is gone.Then, add triisopropyl borate ester (1.50mL, 6.55mmol) and carried out 22 hours stirring.Stirring Afterwards, add the sodium hydrate aqueous solution (4mL, 16mmol) of 4M and carried out 15 minutes stirring.Water is added in the reaction solution, Extracted using ethyl acetate (140mL).Organic layer is washed using saturated sodium-chloride water solution, by organic layer and water layer point From.After being dehydrated to organic layer using magnesium sulfate, from organic layer reduced pressure concentration low boiling point component is gone out, resulting in target 4- { [4- (2- naphthyls) -6- phenyl] pyridine -2- bases } phenylboric acid faint yellow solid (receipts amount 1.67g, yield 83%).
Embodiment -2
[chemical formula 116]
In argon gas stream by 4- { [4- (2- naphthyls) -6- phenyl] pyridine -2- bases } phenylboric acid (1.60g, 3.99mmol), 2- (3- bromophenyls) -4,6- diphenyl -1,3,5- triazines (1.04g, 2.68mmol), tetrakis triphenylphosphine palladium (0.107g, 0.08mmol) it is dissolved in tetrahydrofuran (50mL).The wet chemical (4mL, 8.0mmol) of 2M is added thereto to, in 80 DEG C Carry out 25 hours stirring.After naturally cooling to room temperature, water (80mL), methyl alcohol (20mL) are added, and consolidating for precipitation is collected by filtration Body.Gained solid is washed with water (50mL), methyl alcohol (50mL), hexane (50mL).The solid dissolving is made in toluene (400mL) diatomite filtration, is carried out, after reduced pressure concentration is carried out to filtrate, is further carried out by recrystallization (toluene) pure Change, resulting in 2- { 4 '-[4- (2- naphthyls) -6- phenylpyridine -2- bases] biphenyl -3- bases } -4,6- diphenyl -1 of target, The white powder (receipts amount 1.36g, yield 76%) of 3,5- triazines (compound A-362).
1H-NMR(CDCl3)δ(ppm):7.52-7.67 (m, 11H), 7.71 (t, J=7.7Hz, 1H), 7.90-8.07 (m, 8H), 8.13 (d, J=1.4Hz, 1H), 8.26-8.31 (m, 3H), 8.43 (d, J=8.5Hz, 2H), 8.79-8.84 (m, 5H), 9.10 (t, J=1.6Hz, 1H).
The Tg of gained compound A-362 is 109 DEG C.
Synthesis example -7
[chemical formula 117]
Benzaldehyde (3.00g, 0.0283mol), 2 acetyl naphthalene (4.83g, 0.0284mol) are dissolved in air atmosphere In acetic acid (57mL), the concentrated sulfuric acid (7.9mL, 0.141mol) is added dropwise, and has carried out at room temperature 21 hours stirring.After stirring, plus Enter 50mL water, the solid of precipitation is collected by filtration.Gained solid is washed with water (50mL), the 1- of target is resulting in The brown solid (receipts amount 7.21g, yield 99%) of (2- naphthyls) -3- phenylpropen ketone.
Synthesis example -8
[chemical formula 118]
By 1- (2- naphthyls) -3- phenylpropen ketone (3.00g, 0.0116mol), 1- (4- Bromophenacyls in air atmosphere Methyl) bromopyridine (6.21g, 0.0174mol), ammonium acetate (17.91g, 0.232mol) be suspended in acetic acid (120mL), dimethyl The mixed solvent of formamide (120mL), has carried out 7 hours stirring in 150 DEG C.After naturally cooling to room temperature, 50mL water is added, The solid of precipitation is collected by filtration.Gained solid is washed with water (50mL), resulting in the 2- (4- bromophenyls) of target- The brown solid (receipts amount 2.39g, yield 47%) of 6- (2- naphthyls) -4- phenylpyridines.
Synthesis example -9
[chemical formula 119]
2- (4- bromophenyls) -6- (2- naphthyls) -4- phenylpyridines (1.70g, 3.90mmol) is dissolved in argon gas stream Tetrahydrofuran (47mL), is stirred in -78 DEG C.N-BuLi (hexane solution, 5.25mmol) is added dropwise thereto and is carried out After stirring, further add triisopropyl borate ester (1.20mL, 5.23mmol) and carried out 19 hours stirring.After stirring, plus Enter the sodium hydrate aqueous solution (3.5mL, 14mmol) of 4M and carried out 50 minutes stirring.Water is added in the reaction solution, and Extracted using ethyl acetate (120mL).Organic layer is washed 2 times with saturated sodium-chloride water solution, by organic layer and water Layer is separated.After being dehydrated to organic layer using magnesium sulfate, from organic layer reduced pressure concentration low boiling point component is gone out, be resulting in Faint yellow solid (receipts amount 1.56g, the yield of 4- { [6- (2- the naphthyls) -4- phenyl] pyridine -2- bases } phenylboric acid of target 100%).
Embodiment -3
[chemical formula 120]
In argon gas stream by 4- { [6- (2- naphthyls) -4- phenyl] pyridine -2- bases } phenylboric acid (1.30g, 3.24mmol), 2- (3- bromophenyls) -4,6- diphenyl -1,3,5- triazines (0.97g, 2.49mmol), tetrakis triphenylphosphine palladium (0.129g, 0.11mmol) it is dissolved in tetrahydrofuran (50mL).The wet chemical (3.8mL, 7.60mmol) of 2M is added thereto to, enters one Step has carried out 29 hours stirring.After naturally cooling to room temperature, water (80mL), methyl alcohol (20mL) are added, consolidating for precipitation is collected by filtration Body, is washed using water (50mL), methyl alcohol (50mL), hexane (50mL) to solid.The solid dissolving is made in toluene (300mL) diatomite filtration, is carried out, reduced pressure concentration is carried out to filtrate and it is dried after solidification, further by recrystallization (toluene) is purified, resulting in the 2- { 4 '-[6- (2- naphthyls) -4- phenylpyridine -2- bases] biphenyl -3- bases } of target - The white powder (receipts amount 1.03g, yield 62%) of 4,6- diphenyl -1,3,5- triazines (compound A-722).
1H-NMR(CDCl3)δ(ppm):7.50-7.65 (m, 11H), 7.71 (t, J=8.0Hz, 1H), 7.82-7.86 (m, 2H), 7.90-7.97 (m, 4H), 8.00-8.05 (m, 3H), 8.09 (d, J=1.4Hz, 1H), 8.41-8.45 (m, 3H), 8.71 (brs, 1H), 8.80-8.84 (m, 5H), 9.11 (t, J=2.0Hz, 1H).
The Tg of gained compound A-722 is 110 DEG C.
Synthesis example -10
[chemical formula 121]
In air atmosphere by 4- chloro-acetophenones (10.01g, 0.0648mol), 4- bromobenzaldehydes (12.01g, Acetic acid (100mL) 0.0649mol) is dissolved in, the concentrated sulfuric acid (13.5mL, 0.244mol) is added dropwise, and it is little to have carried out 22 at room temperature When stir.After stirring, the water of 150mL is added, the solid of precipitation is collected by filtration.Gained solid is washed with water (200mL), Resulting in yellow solid (receipts amount 19.21g, the yield of 3- (4- bromophenyls) -1- (4- chlorphenyls) propenone of target 92%).
Synthesis example -11
[chemical formula 122]
By 3- (4- bromophenyls) -1- (4- chlorphenyls) propenone (9.00g, 0.0280mmol), 1- (4- in air atmosphere Chlorophenacyl) bromopyridine (13.13g, 0.0420mol), ammonium acetate (43.26g, 0.561mol) be suspended in acetic acid (120mL) and dimethylformamide (50mL) mixed solvent, carried out in 150 DEG C 17 hours stir.Naturally cool to room temperature Afterwards, water (350mL), methyl alcohol (50mL) are added, the solid of precipitation is collected by filtration.By gained solid water (300mL), methyl alcohol (100mL) washed, resulting in the white solid of double (4- chlorphenyls) pyridines of 4- (4- bromophenyls) -2,6- of target (receipts amount 11.85g, yield 93%).
Synthesis example -12
[chemical formula 123]
4- (4- bromophenyls) -2,6- double (4- chlorphenyls) pyridine (5.00g, 11.0mmol) is dissolved in into four in argon gas stream Hydrogen furans (55mL), is stirred in -78 DEG C.N-BuLi (hexane solution, 14.43mmol) is added dropwise thereto and is carried out After stirring in 3 hours, further add triisopropyl borate ester (3.4mL, 14.8mmol) and carried out 19 hours stirring.Stirring Afterwards, the sodium hydrate aqueous solution (8.0mL, 14mmol) of 4M is added, and has carried out 45 minutes stirring.Add in the reaction solution Water, and extracted using ethyl acetate (100mL).Wash organic layer with water, and organic layer and water layer are separated.Using After magnesium sulfate is dehydrated to organic layer, from organic layer reduced pressure concentration low boiling point component is gone out, resulting in target 4- [2, Double (4- chlorphenyls) pyridin-4-yls of 6-] phenylboric acid yellow solid (receipts amount 4.23g, yield 92%).
Synthesis example -13
[chemical formula 124]
By 4- [double (4- chlorphenyls) pyridin-4-yls of 2,6-] phenylboric acid (3.89g, 9.26mmol), 2- in argon gas stream (3- bromophenyls) -4,6- diphenyl -1,3,5- triazines (1.55g, 3.99mmol), tetrakis triphenylphosphine palladium (0.140g, 0.12mmol) it is dissolved in tetrahydrofuran (50mL).The wet chemical (6.0mL, 12.0mmol) of 2M is added thereto to, is gone forward side by side Stirring in 17 hours is gone.After naturally cooling to room temperature, water (40mL), methyl alcohol (10mL) are added, the solid of precipitation is collected by filtration, profit Solid is washed with water (50mL), methyl alcohol (50mL), hexane (50mL).The solid is set to be suspended in toluene (210mL), Heat filtering is carried out after input silica gel, reduced pressure concentration has been carried out to filtrate.Further, by carry out 2 times recrystallization (toluene) and Purified, resulting in 2- { 4 '-[2,6- double (4- chlorphenyls) pyridin-4-yls] biphenyl -3- bases } -4, the 6- hexichol of target The white powder (receipts amount 1.64g, yield 60%) of base -1,3,5- triazines.
Embodiment -4
[chemical formula 125]
By 2- { 4 '-[2,6- double (4- chlorphenyls) pyridin-4-yl] biphenyl -3- bases } -4,6- diphenyl -1 in argon gas stream, 3,5- triazines (1.02g, 1.49mmol), 3- pyridine boronic acids (1.10g, 8.95mmol), acid chloride (37.3mg, 0.17mmol), 2- dicyclohexylphosphontetrafluoroborates -2 ', 4 ', 6 '-tri isopropyl biphenyl (79.0mg, 0.17mmol) is suspended in tetrahydrofuran (50mL), is added dropwise The wet chemical (5.8mL, 11.6mmol) of 2M, and carried out 65 hours stirring in 80 DEG C.After naturally cooling to room temperature, plus Enter water (50mL), methyl alcohol (10mL), hexane (20mL), the solid of precipitation is collected by filtration.By gained solid water (50mL), methyl alcohol (50mL), hexane (50mL) is washed.Further, (toluene) is recrystallized by Jing and is purified, resulting in mesh Target 2- (4 '-{ double [4- (3- pyridine radicals) phenyl] pyridin-4-yls of 2,6- } biphenyl -3- bases) -4,6- diphenyl -1,3,5- triazines The pale solid (receipts amount 0.55g, yield 48%) of (compound A-155).
The Tg of gained compound A-155 is 139 DEG C.
Synthesis example -14
[chemical formula 126]
In air atmosphere by 4- bromoacetophenones (14.18g, 0.0712mol), 4- chlorobenzaldehydes (10.00g, Acetic acid (100mL) 0.0711mol) is dissolved in, the concentrated sulfuric acid (13.5mL, 0.244mol) is added dropwise, and it is little to have carried out 48 at room temperature When stir.After stirring, the water of 150mL is added, the solid of precipitation is collected by filtration.Gained solid is washed with water (200mL), Resulting in yellow solid (receipts amount 21.14g, the yield of 1- (4- bromophenyls) -3- (4- chlorphenyls) propenone of target 92%).
Synthesis example -15
[chemical formula 127]
By 1- (4- bromophenyls) -3- (4- chlorphenyls) propenone (10.00g, 0.0311mmol), 1- in air atmosphere (4- Chlorophenacyls) bromopyridine (13.58g, 0.0434mol), ammonium acetate (48.33g, 0.627mol) are suspended in acetic acid (130mL) and dimethylformamide (70mL) mixed solvent, carried out in 150 DEG C 25 hours stir.Naturally cool to room temperature Afterwards, water (300mL) is added, the solid of precipitation is collected by filtration.Gained solid is washed with water (300mL), methyl alcohol (100mL) Wash, resulting in white solid (receipts amount 13.09g, receipts of double (4- chlorphenyls) pyridines of 2- (4- bromophenyls) -4,6- of target Rate 93%).
Synthesis example -16
[chemical formula 128]
2- (4- bromophenyls) -4,6- (4- chlorphenyls) pyridine (5.00g, 11.0mmol) is dissolved in into tetrahydrochysene in argon gas stream Furans (55mL), is stirred in -78 DEG C.N-BuLi (hexane solution, 14.43mmol) is added dropwise thereto and to carry out 3 little When stirring after, further add triisopropyl borate ester (3.6mL, 15.7mmol) and carried out at room temperature 22 hours stir. After stirring, the sodium hydrate aqueous solution (8.0mL, 14mmol) of 4M is added, and carried out at room temperature 30 minutes stirring.It is anti-to this Answer and add in solution water, and extracted using ethyl acetate (100mL).Wash organic layer with water, and by organic layer and water Layer is separated.After being dehydrated to organic layer using magnesium sulfate, from organic layer reduced pressure concentration low boiling point component is gone out, thus obtained The yellow solid (receipts amount 4.44g, yield 96%) of the 4- of target [double (4- chlorphenyls) pyridine -2- bases of 4,6-] phenylboric acid.
Synthesis example -17
[chemical formula 129]
By 4- [4,6- (4- chlorphenyls) pyridine -2- bases] phenylboric acid (2.73g, 6.50mmol), 2- (3- in argon gas stream Bromophenyl) -4,6- diphenyl -1,3,5- triazines (1.56g, 4.02mmol), tetrakis triphenylphosphine palladium (0.143g, 0.12mmol) It is dissolved in tetrahydrofuran (50mL).The wet chemical (6.0mL, 12.0mmol) of 2M is added thereto to, is carried out in 75 DEG C Stir within 68 hours.After naturally cooling to room temperature, water (50mL), methyl alcohol (30mL) are added, the solid of precipitation is collected by filtration, and utilized Water (50mL), methyl alcohol (50mL), hexane (50mL) are washed to solid.Make the solid dissolving in toluene (400mL), throwing Enter and carry out after silica gel heat filtering, and reduced pressure concentration has been carried out to filtrate.Further, by carry out 2 times recrystallization (toluene) and Purified, resulting in 2- { 4 '-[4,6- double (4- chlorphenyls) pyridine -2- bases] biphenyl -3- bases } -4, the 6- hexichol of target The white powder (receipts amount 1.27g, yield 46%) of base -1,3,5- triazines.
Embodiment -5
[chemical formula 130]
By 2- { 4 '-[double (4- chlorphenyls) pyridine -2- bases of 4,6-] biphenyl -3- bases } -4,6- diphenyl -1 in argon gas stream, 3,5- triazines (1.97g, 2.88mmol), 3- pyridine boronic acids (1.45g, 11.8mmol), acid chloride (26.3mg, 0.12mmol), 2- dicyclohexylphosphontetrafluoroborates -2 ', 4 ', 6 '-tri isopropyl biphenyl (0.115g, 0.24mmol) is suspended in tetrahydrofuran (100mL), is added dropwise The wet chemical (11.7mL, 23.4mmol) of 2M, and carried out 25 hours stirring in 75 DEG C.After naturally cooling to room temperature, Water (50mL), methyl alcohol (30mL) are added, the solid of precipitation is collected by filtration.By gained solid water (50mL), methyl alcohol (50mL), oneself Alkane (50mL) is washed.Make the solid dissolving in toluene (500mL), carry out diatomite filtration, and filtrate is subtracted Pressure concentration.Further, Jing recrystallizes (toluene) and is purified, and resulting in 2- (4 '-{ 4,6- double [4- (3- pyrroles of target Piperidinyl) phenyl] pyridine -2- bases biphenyl -3- bases) -4,6- diphenyl -1,3,5- triazines (compound A-515) pale solid (receipts amount 1.56g, yield 70%).
The Tg of gained compound A-515 is 139 DEG C.
Synthesis example -18
[chemical formula 131]
In argon gas stream by 2- (3- bromophenyls) -4,6- diphenyl -1,3,5- triazines (10.0g, 25.8mmol), double frequency that Alcohol close two boron (7.19g, 28.3mmol), [1,1 '-bis- (diphenylphosphine) ferrocene] palladium chloride (II) (0.94g, 1.29mmol) and potassium acetate (7.48g, 76.2mmol) is dissolved in dimethyl sulfoxide (200mL), carried out 4 hours stirring in 80 DEG C. After natural cooling, water (100mL) is added in the reaction solution, and carried out using ethyl acetate (300mL), hexane (100mL) Extraction.Using brine It organic layer, and organic layer and water layer are separated.Organic layer is being dehydrated using magnesium sulfate Afterwards, low boiling point component is removed from organic layer vacuum distillation, has obtained being dried coagulum.Further, using column chromatography (hexane: Chloroform) purified, 2- [3- { (4,4,5,5- tetramethyl -1,3,2- dioxaborinate -2- bases) phenyl }] -4 is resulting in, The Off-white solid (receipts amount 7.40g, yield 66%) of 6- diphenyl -1,3,5- triazines.
Synthesis example -19
[chemical formula 132]
Potassium hydroxide is suspended in the mixed solvent of ethanol (10mL), water (20mL) in air atmosphere, 1- acetyl is added dropwise Base naphthalene (5.00g, 0.0294mmol), has carried out 10 minutes stirring in 0 DEG C.After stirring, addition make 4- bromobenzaldehydes (5.44g, The solution of ethanol (10mL) 0.0294mmol) is dissolved in, and has carried out at room temperature 16 hours stirring.Then, it is anti-to this Answer and add in solution water (200mL), the solid of precipitation is collected by filtration.Gained solid is washed with water (200mL), thus The yellow solid (receipts amount 9.78g, yield 99%) of 1- (1- naphthyls) -3- (4- bromophenyls) propenone of target is arrived.
Synthesis example -20
[chemical formula 133]
By 1- (1- naphthyls) -3- (4- bromophenyls) propenone (3.00g, 8.90mmol), 1- benzoyls in air atmosphere Methyl bromopyridine (3.71g, 0.0133mol) and ammonium acetate (13.81g, 0.179mol) are dissolved in acetic acid (110mL) and dimethyl The mixed solvent of formamide (20mL), and carried out 16 hours stirring in 150 DEG C.After naturally cooling to room temperature, water is added (250mL) solid of precipitation, is collected by filtration.Gained solid is washed with water (200mL), the 4- of target is resulting in The brown solid (receipts amount 3.32g, yield 86%) of (4- bromophenyls) -2- (1- naphthyls) -6- phenylpyridines.
Embodiment -6
[chemical formula 134]
By 4- (4- bromophenyls) -2- (1- naphthyls) -6- phenylpyridines (1.59g, 3.65mmol), 2- [3- in argon gas stream { (4,4,5,5- tetramethyl -1,3,2- dioxaborinate -2- bases) phenyl }] -4,6- diphenyl -1,3,5- triazines (1.91g, 4.38mmol) and tetrakis triphenylphosphine palladium (0.21g, 0.183mmol) is dissolved in 1,4- dioxanes (80mL).Thereto The wet chemical (5.6mL, 11.2mmol) of 2M is added, has further carried out 16 hours stirring in 100 DEG C.Naturally cool to After room temperature, reduced pressure concentration is carried out to reaction solution, and add water (100mL), the solid of precipitation is collected by filtration, and utilize water (80mL), methyl alcohol (80mL), hexane (80mL) are washed.5 recrystallizations (ethyl acetate) are further carried out, is thus obtained The 2- of target { 4 '-[2- (1- naphthyls) -6- phenylpyridine -4- bases] biphenyl -3- bases } -4,6- diphenyl -1,3,5- triazines (are changed Compound A-4) brown powder (receipts amount 1.02g, yield 42%).
1H-NMR(CDCl3)δ(ppm):7.43-7.66 (m, 12H), 7.70 (t, J=7.6Hz, 1H) 7.80 (dd, J= 1.1Hz, 7.2Hz, 1H), 7.85 (d, J=1.5Hz, 1H), 7.90-7.98 (m, 7H), 8.10 (d, J=1.5Hz, 1H), 8.20- 8.23 (m, 2H), 8.34 (m, 1H), 8.79-8.83 (m, 5H), 9.07 (t, J=1.7Hz, 1H).
Synthesis example -21
[chemical formula 135]
By 4- bromoacetophenones (5.00g, 0.0251mol) and 1- naphthaldehydes (3.98g, 0.0255mol) in air atmosphere Acetic acid (100mL) is dissolved in, the concentrated sulfuric acid (7.0mL, 0.127mol) is added dropwise, and carried out at room temperature 15 hours stirring.Then, The water of 300mL is added, and the solid of precipitation is collected by filtration.Gained solid is washed with water (100mL), methyl alcohol (30mL), Resulting in the yellow solid (receipts amount 5.98g, yield 71%) of 1- (4- bromophenyls) -3- (1- naphthyls) propenone of target.
Synthesis example -22
[chemical formula 136]
By 1- (4- bromophenyls) -3- (1- naphthyls) propenone (4.00g, 0.0119mol), 1- benzoyls in air atmosphere Methyl bromopyridine (4.95g, 0.0178mol) and ammonium acetate (18.33g, 0.238mol) are dissolved in acetic acid (50mL) and dimethyl The mixed solvent of formamide (40mL), and carried out 7 hours stirring in 150 DEG C.After naturally cooling to room temperature, water is added (250mL), and it is collected by filtration the solid of precipitation.Gained solid is washed with water (200mL), methyl alcohol (150mL), thus The brown solid (receipts amount 3.90g, yield 75%) of 2- (4- bromophenyls) -4- (1- the naphthyls) -6- phenylpyridines of target is arrived.
Embodiment -7
[chemical formula 137]
By 2- (4- bromophenyls) -4- (1- naphthyls) -6- phenylpyridines (1.00g, 2.29mmol), 2- [3- in argon gas stream { (4,4,5,5- tetramethyl -1,3,2- dioxaborinate -2- bases) phenyl }] -4,6- diphenyl -1,3,5- triazines (1.20g, 2.75mmol) and tetrakis triphenylphosphine palladium (0.14g, 0.115mmol) is dissolved in 1,4- dioxanes (50mL).Thereto The wet chemical (3.4mL, 6.8mmol) of 2M is added, has further carried out 21 hours stirring in 100 DEG C.Naturally cool to After room temperature, reduced pressure concentration is carried out to reaction solution, add water (50mL), methyl alcohol (20mL), the solid of precipitation, and profit is collected by filtration Solid is washed with water (70mL), methyl alcohol (70mL), hexane (70mL).Make the solid dissolving in toluene (200mL), enter Row diatomite is filtered, and has carried out reduced pressure concentration to filtrate.Gained solid is suspended in into ethyl acetate (150mL), and is carried out Filter.Solids with methanol (50mL) to separating out from the filtrate is washed, and resulting in the 2- { 4 '-[4- (1- of target Naphthyl) -6- phenylpyridine -2- bases] biphenyl -3- bases -4,6- diphenyl -1,3,5- triazines (compound A-364) brown powder (receipts amount 0.93g, yield 61%).
1H-NMR(CDCl3)δ(ppm):7.44-7.66 (m, 13H), 7.69 (t, J=7.7Hz, 1H), 7.88-7.95 (m, 5H), 7.99 (t, J=7.4Hz, 3H) 8.25-8.28 (m, 2H), 8.40 (d, J=8.4Hz, 2H), 8.78-8.83 (m, 5H), 9.09 (t, J=1.8Hz, 1H).
Synthesis example -23
[chemical formula 138]
By 2 acetyl naphthalene (6.00g, 0.0353mol) and 1- naphthaldehydes (5.61g, 0.0359mol) in air atmosphere Acetic acid (100mL) is dissolved in, the concentrated sulfuric acid (8.0mL, 0.145mol) is added dropwise, and carried out at room temperature 15 hours stirring.Then, The water of 300mL is added, the solid of precipitation is collected by filtration.Gained solid is washed with water (150mL), methyl alcohol (30mL), by This has obtained the orange solids (receipts amount 9.49g, yield 87%) of 1- (2- naphthyls) -3- (1- naphthyls) propenone of target.
Synthesis example -24
[chemical formula 139]
By 1- (2- naphthyls) -3- (1- naphthyls) propenone (5.00g, 0.0162mol), 1- (4- bromobenzenes in air atmosphere Formyl methyl) bromopyridine (8.68g, 0.0243mol) and ammonium acetate (24.98g, 0.324mol) be dissolved in acetic acid (65mL) and two The mixed solvent of NMF (40mL), and carried out 7 hours stirring in 150 DEG C.After naturally cooling to room temperature, water is added (250mL) solid of precipitation, is collected by filtration, gained solid is washed with water (200mL), methyl alcohol (150mL).Further (methyl alcohol) is recrystallized to the solid through washing, 2- (4- bromophenyls) -4- (1- the naphthyls) -6- of target is resulting in The brown solid (receipts amount 2.45g, yield 31%) of (2- naphthyls) pyridine.
Embodiment -8
[chemical formula 140]
By 2- (4- bromophenyls) -4- (1- naphthyls) -6- (2- naphthyls) pyridine (1.20g, 2.47mmol), 2- in argon gas stream [3- { (4,4,5,5- tetramethyl -1,3,2- dioxaborinate -2- bases) phenyl }] -4,6- diphenyl -1,3,5- triazines (1.42g, 2.75mmol) and tetrakis triphenylphosphine palladium (0.17g, 0.144mmol) is dissolved in 1,4- dioxanes (50mL).Thereto The wet chemical (3.7mL, 7.4mmol) of 2M is added, has further carried out 21 hours stirring in 100 DEG C.Naturally cool to After room temperature, reduced pressure concentration is carried out to reaction solution, add water (50mL), methyl alcohol (20mL), the solid of precipitation, and profit is collected by filtration Solid is washed with water (70mL), methyl alcohol (70mL), hexane (70mL).Make the solid dissolving in toluene (300mL), enter Row diatomite is filtered, and has carried out reduced pressure concentration to filtrate.(ethyl acetate/methanol) is recrystallized to gained solid, thus 2- { 4 '-[4- (1- naphthyls) -6- (2- naphthyls) pyridine -2- bases] biphenyl -3- bases } -4,6- diphenyl -1,3 of target have been obtained, The brown powder (receipts amount 0.93g, yield 61%) of 5- triazines (compound A-365).
1H-NMR(CDCl3)δ(ppm):7.51-7.67 (m, 13H), 7.70 (t, J=7.7Hz, 1H), 7.89-8.05 (m, 10H), 8.42-8.46 (m, 3H), 8.71 (d, J=1.1Hz, 1H), 8.79-8.84 (m, 5H), 9.10 (t, J=1.7Hz, 1H).
The Tg of gained compound A-365 is 127 DEG C.
Embodiment -9
[chemical formula 141]
In argon gas stream by 2- (3- bromophenyls) -4,6- diphenyl -1,3,5- triazines (1.50g, 3.86mmol), 4- (4, 6- hexichol yl pyridines -2- bases) phenylboric acid (1.63g, 4.64mmol), tetra-triphenylphosphine palladium (134mg, 1.16mmol) and carbonic acid Potassium (1.60g, 11.6mmol) is suspended in the mixed solvent of tetrahydrofuran (83mL) and water (11mL).By gained mixture in 70 DEG C Carry out 25 hours stirring.After naturally cooling to room temperature, water (100mL) is added, the solid of precipitation is collected by filtration, using water, first Alcohol, hexane are washed to solid.(toluene) is recrystallized to gained solid, 4,6- as object are resulting in The pale solid of diphenyl -2- [4 '-(4,6- hexichol yl pyridines -2- bases)-biphenyl -3- bases] -1,3,5- triazines (A-721) (receipts amount 1.79g, yield 99%).
1H-NMR(CDCl3)δ(ppm):7.43-7.64 (m, 12H), 7.68 (t, J=8.1Hz, 1H), 7.78 (dd, J= 8.5Hz, 1.5Hz, 2H), 7.89-7.93 (m, 4H), 7.98 (d, J=1.4Hz, 1H), 8.23 (dd, J=8.6Hz, 1.4Hz, 2H), 8.37 (d, J=8.5Hz, 2H), 8.77-8.82 (m, 5H), 9.08 (t, J=1.6Hz, 1H).
The Tg of gained compound A-721 is 102 DEG C.
Synthesis example -25
[chemical formula 142]
It is in air atmosphere that 4 '-bromoacetophenone (1.94g, 9.70mmol) and 9- formaldehyde phenanthrene (2.00g, 9.70mmol) is molten Solution is added dropwise the concentrated sulfuric acid (3.0mL, 0.054mol) in acetic acid (50mL), and has carried out at room temperature 21 hours stirring.Then, plus Enter water (200mL), methyl alcohol (50mL), the solid of precipitation is collected by filtration.Gained solid water (100mL), methyl alcohol (50mL) are entered Washing is gone.By solid input methyl alcohol (300mL), the mixed solvent of hexane (50mL) and after being stirred, it is separated by filtration Go out solid, resulting in yellow solid (receipts amount 2.7g, the yield of 1- (4- bromophenyls) -3- (9- phenanthryl) propenone of target 72%).
Synthesis example -26
[chemical formula 143]
By 1- (4- bromophenyls) -3- (9- phenanthryl) propenone (2.7g, 6.97mmol), 1- benzoyl first in air atmosphere Bromide pyridine (2.97g, 0.0107mol) and ammonium acetate (10.75g, 0.139mol) are dissolved in acetic acid (50mL) and dimethyl methyl The mixed solvent of acid amides (28mL), has carried out 19 hours stirring in 150 DEG C.After naturally cooling to room temperature, water (400mL) is added, The solid of precipitation is collected by filtration, gained solid is washed with water (100mL), methyl alcohol (100mL).By consolidating through washing Body is suspended in methyl alcohol (200mL) and is stirred, and has thus carried out further washing to solid.Gained solid is utilized into post color Spectrum (chloroform:Hexane) purified, resulting in target 2- (4- bromophenyls) -4- (9- phenanthryl) -6- phenylpyridines it is white Color solid (receipts amount 0.40g, yield 12%).
Embodiment -10
[chemical formula 144]
By 2- (4- bromophenyls) -4- (9- phenanthryl) -6- phenylpyridines (0.55g, 1.14mmol), 2- [3- in argon gas stream { (4,4,5,5- tetramethyl -1,3,2- dioxaborinate -2- bases) phenyl }] -4,6- diphenyl -1,3,5- triazines (0.62g, 1.42mmol) and tetrakis triphenylphosphine palladium (0.080g, 0.069mmol) is dissolved in tetrahydrofuran (11mL).It is added thereto to 2M Wet chemical (1.7mL, 3.4mmol), further carried out in 80 DEG C 50 hours stir.After naturally cooling to room temperature, Water (20mL), methyl alcohol (1mL) are added, the solid of precipitation is collected by filtration, using water (60mL), methyl alcohol (120mL), hexane (60mL) Solid is washed.(toluene) is recrystallized to gained solid, resulting in target 2- 4 '-[(9- is luxuriant and rich with fragrance for 4- Base) -6- phenylpyridine -2- bases] biphenyl -3- bases -4,6- diphenyl -1,3,5- triazines (compound A-367) white powder (receipts amount 0.63g, yield 77%).
1H-NMR(CDCl3)δ(ppm):7.46-7.77(m,14H),7.85(s,1H),7.91-8.03(m,7H),8.27- 8.29 (d, J=7.0Hz, 2H), 8.40-8.43 (d, J=8.6Hz, 2H), 8.77-8.86 (m, 7H), 9.09 (t, J=1.7Hz, 1H).
Synthesis example -27
[chemical formula 145]
Potassium hydroxide (5.57g, 0.099mol) is suspended in the mixing of ethanol (30mL), water (60mL) in air atmosphere Solvent, is added dropwise 2- acetylpyridines (10.00g, 0.0825mol), has carried out 35 minutes stirring in 0 DEG C.After stirring, benzene first is added Aldehyde (8.76g, 0.0825mol), and carried out at room temperature 4 hours stirring.Then, water is added in the reaction solution (150mL) solid of precipitation, is collected by filtration.Gained solid is washed with water (200mL), the 1- of target is resulting in The yellow solid (receipts amount 16.98g, yield 98%) of (2- pyridine radicals) -3- phenylpropen ketone.
Synthesis example -28
[chemical formula 146]
By 1- (2- pyridine radicals) -3- phenylpropen ketone (8.51g, 0.0407mol), 1- (4- bromobenzene first in air atmosphere Acyl methyl) bromopyridine (19.82g, 0.0555mol) and ammonium acetate (58.22g, 0.755mol) be dissolved in acetic acid (150mL) and two The mixed solvent of NMF (150mL), has carried out 15 hours stirring in 150 DEG C.After naturally cooling to room temperature, water is added (250mL) solid of precipitation, is collected by filtration, gained solid is washed with water (200mL).Further by through washing Solid dissolving after adding silica gel, is filtered in ethyl acetate (200mL).Reduced pressure concentration is carried out to gained filtrate, thus Brown solid (receipts amount 10.00g, the yield of 2- (4- bromophenyls) -4- phenyl -6- (2- pyridine radicals) pyridine of target are obtained 63%).
Synthesis example -29
[chemical formula 147]
2- (4- bromophenyls) -4- phenyl -6- (2- pyridine radicals) pyridine (10.00g, 25.8mmol) are dissolved in argon gas stream In tetrahydrofuran (200mL), it is stirred in -78 DEG C.N-BuLi (hexane solution, 31.0mmol) is added dropwise thereto to go forward side by side After row stirring in 2 hours, triisopropyl borate ester (7.2mL, 31.4mmol) is further added, and carried out at room temperature 17 hours Stirring.Then, the sodium hydrate aqueous solution (12.0mL, 48mmol) of 4M is added, and has carried out at room temperature 1 hour stirring.Will The solid of precipitation is washed using water (200mL), hexane (200mL), resulting in 4- [4- phenyl -6- (the 2- pyrroles of target Piperidinyl) pyridine -2- bases] phenylboric acid yellow solid (receipts amount 3.25g, yield 36%).
Embodiment -11
[chemical formula 148]
In argon gas stream by 4- [4- phenyl -6- (2- pyridine radicals) pyridine -2- bases] phenylboric acid (3.00g, 8.53mmol), 2- (3- bromophenyls) -4,6- diphenyl -1,3,5- triazines (2.76g, 7.11mmol) and tetrakis triphenylphosphine palladium (0.247g, 0.214mmol) it is dissolved in tetrahydrofuran (86mL).The wet chemical (12.8mL, 25.60mmol) of 2M is added thereto to, Carry out 18 hours stirring in 80 DEG C.After naturally cooling to room temperature, water (90mL), methyl alcohol (10mL) are added, precipitation is collected by filtration Solid.Gained solid is washed with water (60mL), methyl alcohol (60mL), hexane (60mL).Solid Jing is tied for 2 times again Brilliant (toluene) and purified, resulting in target 2- 4 '-[4- phenyl -6- (2- pyridine radicals) pyridine -2- bases] biphenyl - 3- yls } -4,6- diphenyl -1,3,5- triazines (compound A-743) white powder (receipts amount 3.34g, yield 76%).
1H-NMR(CDCl3)δ(ppm):7.36-7.39 (m, 1H), 7.47-7.66 (m, 9H), 7.71 (t, J=7.6Hz, 1H), 7.84-7.95 (m, 6H), 8.09 (d, J=1.5Hz, 1H), 8.39 (d, J=8.3Hz, 2H), 8.69 (d, J=1.5Hz, 1H), 8.74-8.84 (m, 7H), 9.10 (t, J=1.7Hz, 1H).
Synthesis example -30
[chemical formula 149]
In air atmosphere by 4 '-bromoacetophenone (10.06g, 0.0505mol) and biphenyl -4- formaldehyde (9.17g, Acetic acid (250mL) 0.0503mmol) is dissolved in, the concentrated sulfuric acid (12.5mL, 0.225mol) is added dropwise, and it is little to have carried out 25 at room temperature When stir.Then, water (500mL) is added, the solid of precipitation is collected by filtration.By gained solid water (100mL), methyl alcohol (100mL) washed, resulting in white solid (the receipts amount of 1- (4- bromophenyls) -3- (4- biphenyl) propenone of target 11.61g, yield 63%).
Synthesis example -31
[chemical formula 150]
By 1- (4- bromophenyls) -3- (4- biphenyl) propenone (11.52g, 0.0317mol), 1- benzene first in air atmosphere Acyl methyl bromopyridine (13.24g, 0.0476mol) and ammonium acetate (48.88g, 0.634mol) are dissolved in acetic acid (161mL) and two The mixed solvent of NMF (154mL), has carried out 2 hours stirring in 150 DEG C.After naturally cooling to room temperature, water is added (300mL) solid of precipitation, is collected by filtration.Gained solid is carried out with water (300mL), methyl alcohol (300mL), hexane (100mL) Washing, resulting in 4- (4- biphenyl) -2- (4- the bromophenyls) -6- phenylpyridines of target white solid (receipts amount 13.33g, Yield 91%).
Synthesis example -32
[chemical formula 151]
4- (4- biphenyl) -2- (4- bromophenyls) -6- phenylpyridines (13.20g, 28.6mmol) is dissolved in argon gas stream Tetrahydrofuran (250mL), is stirred in -78 DEG C.N-BuLi (hexane solution, 34.7mmol) is added dropwise thereto and is carried out After stirring in 2 hours, further add triisopropyl borate ester (7.9mL, 34.4mmol) and carried out at room temperature 17 hours stirring Mix.After stirring, the sodium hydrate aqueous solution (16.0mL, 64mmol) of 4M is added, and carried out at room temperature 1 hour stirring.Will The solid of precipitation is washed with water (300mL), hexane (300mL), resulting in 4- [4- (4- the biphenyl) -6- benzene of target Yl pyridines -2- bases] phenylboric acid white solid (receipts amount 9.92g, yield 81%).
Embodiment -12
[chemical formula 152]
In argon gas stream by 4- [4- (4- biphenyl) -6- phenylpyridine -2- bases] phenylboric acid (5.31g, 12.43mmol), 2- (3- bromophenyls) -4,6- diphenyl -1,3,5- triazines (4.30g, 11.08mmol), tetrakis triphenylphosphine palladium (0.387g, 0.335mmol) it is dissolved in tetrahydrofuran (56mL).The wet chemical (17.0mL, 34.00mmol) of 2M is added thereto to, Carry out 28 hours stirring in 80 DEG C.After naturally cooling to room temperature, water (40mL), methyl alcohol (3mL) are added, precipitation is collected by filtration Solid.Gained solid is washed with water (120mL), methyl alcohol (240mL), hexane (120mL).By the solid by tying again Brilliant (toluene) is purified, and resulting in 2- { 4 '-[4- (4- the biphenyl) -6- phenylpyridine -2- bases] biphenyl -3- of target Base } -4,6- diphenyl -1,3,5- triazines (compound A-429) white powder (receipts amount 6.25g, yield 82%).
1H-NMR(CDCl3)δ(ppm):7.39-7.43(m,1H),7.46-7.73(m,14H),7.78-7.90(m,4H), 7.92-7.96 (m, 3H), 7.98 (d, J=1.3Hz, 1H), 8.04 (d, J=1.3Hz, 1H), 8.26 (d, J=6.9Hz, 2H), 8.40 (d, J=8.4Hz, 2H), 8.79-8.84 (m, 5H), 9.10 (t, J=1.7Hz, 1H).
Synthesis example -33
[chemical formula 153]
In air atmosphere by 4- acetyl biphenyls (10.06g, 0.0513mol) and benzaldehyde (5.41g, Acetic acid (250mL) 0.0530mmol) is dissolved in, the concentrated sulfuric acid (12.5mL, 0.225mol) is added dropwise, and it is little to have carried out 25 at room temperature When stir.Then, water (500mL) is added, the solid of precipitation is collected by filtration.By gained solid water (100mL), methyl alcohol (100mL) washed, resulting in faint yellow solid (the receipts amount of 1- (4- the biphenyl) -3- phenylpropen ketone of target 8.35g, yield 57%).
Synthesis example -34
[chemical formula 154]
By 1- (4- biphenyl) -3- phenylpropen ketone (8.33g, 0.0293mol), 1- (4- Bromophenacyls in air atmosphere Methyl) bromopyridine (15.67g, 0.0434mol) and ammonium acetate (45.39g, 0.589mol) be dissolved in acetic acid (116mL) and diformazan The mixed solvent of base formamide (111mL), has carried out 2 hours stirring in 150 DEG C.After naturally cooling to room temperature, water is added (220mL) solid of precipitation, is collected by filtration, gained solid is carried out with water (300mL), methyl alcohol (100mL), hexane (100mL) Washing, resulting in faint yellow solid (the receipts amount of 2- (4- biphenyl) -6- (4- the bromophenyls) -4- phenylpyridines of target 11.98g, yield 88%).
Synthesis example -35
[chemical formula 155]
2- (4- biphenyl) -6- (4- bromophenyls) -4- phenylpyridines (11.95g, 25.8mmol) is dissolved in argon gas stream Tetrahydrofuran (226mL), is stirred in -78 DEG C.N-BuLi (hexane solution, 31.4mmol) is added dropwise thereto and is carried out After stirring in 2 hours, triisopropyl borate ester (7.2mL, 31.4mmol) is further added, and carried out at room temperature 21 hours Stirring.After stirring, the sodium hydrate aqueous solution (14.0mL, 56mmol) of 4M is added, and carried out at room temperature 1 hour stirring. The solid for separating out is washed with water (300mL), hexane (300mL), 4- [6- (4- the biphenyl) -4- of target are resulting in Phenylpyridine -2- bases] phenylboric acid white solid (receipts amount 5.27g, yield 48%).
Embodiment -13
[chemical formula 156]
In argon gas stream by 4- [6- (4- biphenyl) -4- phenylpyridine -2- bases] phenylboric acid (5.20g, 12.17mmol), 2- (3- bromophenyls) -4,6- diphenyl -1,3,5- triazines (4.30g, 11.08mmol), tetrakis triphenylphosphine palladium (0.515g, 0.445mmol) it is dissolved in tetrahydrofuran (55mL).The wet chemical (17.0mL, 34.00mmol) of 2M is added thereto to, Carry out 28 hours stirring in 80 DEG C.After naturally cooling to room temperature, water (40mL), methyl alcohol (3mL) are added, precipitation is collected by filtration Solid.Gained solid is washed with water (120mL), methyl alcohol (240mL), hexane (120mL).By the solid by tying again Brilliant (toluene) is purified, and resulting in 2- { 4 '-[6- (4- the biphenyl) -4- phenylpyridine -2- bases] biphenyl -3- of target Base } -4,6- diphenyl -1,3,5- triazines (compound A-788) white powder (receipts amount 6.72g, yield 88%).
1H-NMR(CDCl3)δ(ppm):7.38-7.41(m,1H),7.47-7.66(m,11H),7.68-7.72(m,3H), 7.77-7.82 (m, 4H), 7.92-7.95 (m, 3H), 7.98-8.01 (dd, J=9.7Hz, 1.3Hz, 2H), 8.34 (d, J= 8.4Hz, 2H), 8.41 (d, J=8.5Hz, 2H), 8.79-8.83 (m, 5H), 9.10 (t, J=1.7Hz, 1H).
Synthesis example -36
[chemical formula 157]
In air atmosphere by 4 '-bromoacetophenone (12.5g, 62.8mmol) and 4- tolyl aldehydes (8.43g, Acetic acid (100mL) 62.8mmol) is dissolved in, the concentrated sulfuric acid (15mL) is added dropwise, and carried out at room temperature 26 hours stirring.Then, Water (300mL) is added, the solid of precipitation is collected by filtration.Gained solid is washed with water (100mL), methyl alcohol (100mL), by This has obtained faint yellow solid (receipts amount 9.86g, the yield of 1- (4- bromophenyls) -3- (4- aminomethyl phenyls) propenone of target 50%).
Synthesis example -37
[chemical formula 158]
In air atmosphere by 4 '-bromoacetophenone (25.0g, 126mmol) and 3,5- dimethylbenzaldehydes (15.1g, Acetic acid (200mL) 126mmol) is dissolved in, the concentrated sulfuric acid (30mL) is added dropwise, and carried out at room temperature 24 hours stirring.Then, plus Enter water (300mL), the solid of precipitation is collected by filtration.Gained solid is washed with water (100mL), methyl alcohol (100mL), thus Faint yellow solid (receipts amount 35.4g, the yield of 1- (4- bromophenyls) -3- (3,5- 3,5-dimethylphenyls) propenone of target are obtained 94%).
Synthesis example -38
[chemical formula 159]
In air atmosphere by 2- acetyl group benzofurans (3.00g, 18.7mmol) and 4- bromobenzaldehydes (3.47g, Acetic acid (30mL) 18.7mmol) is dissolved in, the concentrated sulfuric acid (4.00mL) is added dropwise, and carried out at room temperature 24 hours stirring.Then, Water (30mL) is added, the solid of precipitation is collected by filtration.Gained solid is washed with water (50mL), methyl alcohol (50mL), thus Faint yellow solid (receipts amount 5.68g, the yield of 1- (2- benzofuranyls) -3- (4- bromophenyls) propenone of target are obtained 93%).
Synthesis example -39
[chemical formula 160]
In air atmosphere by parabromoacetophenone (1.36g, 6.84mmol) and benzofuran 2- formaldehyde (1.00g, Acetic acid (10mL) 6.84mmol) is dissolved in, the concentrated sulfuric acid (1.33mL) is added dropwise, and carried out at room temperature 24 hours stirring.Then, Water (20mL) is added, the solid of precipitation is collected by filtration.Gained solid is washed with water (50mL), methyl alcohol (50mL), thus Faint yellow solid (receipts amount 2.14g, the yield of 3- (2- benzofuranyls) -1- (4- bromophenyls) propenone of target are obtained 95%).
Synthesis example -40
[chemical formula 161]
By 1- (4- bromophenyls) -3- (4- aminomethyl phenyls) propenone (10.0g, 32.2mmol), 1- benzene in air atmosphere Formyl methyl bromopyridine (12.9g, 46.5mmol) and ammonium acetate (38.4g, 498mol) are dissolved in acetic acid (100mL) and dimethyl The mixed solvent of formamide (100mL), has carried out 15 hours stirring in 150 DEG C.After naturally cooling to room temperature, water is added (300mL) solid of precipitation, is collected by filtration, gained solid is carried out with water (300mL), methyl alcohol (100mL), hexane (100mL) Washing, resulting in faint yellow solid (the receipts amount of 6- (4- bromophenyls) -4- (4- the aminomethyl phenyls) -2- phenylpyridines of target 11.8g, yield 89%).
Synthesis example -41
[chemical formula 162]
By 1- (4- bromophenyls) -3- (3,5- 3,5-dimethylphenyls) propenone (7.0g, 22.2mmol), 1- in air atmosphere Phenacyl bromopyridine (8.87g, 31.1mmol) and ammonium acetate (25.7g, 333mol) are dissolved in acetic acid (70mL) and diformazan The mixed solvent of base formamide (70mL), has carried out 15 hours stirring in 150 DEG C.After naturally cooling to room temperature, water is added (200mL) solid of precipitation, is collected by filtration, gained solid is carried out with water (100mL), methyl alcohol (100mL), hexane (100mL) Washing, resulting in the faint yellow solid of 6- (4- bromophenyls) -4- (3,5- the 3,5-dimethylphenyl) -2- phenylpyridines of target (receipts amount 7.28g, yield 79%).
Synthesis example -42
[chemical formula 163]
By 1- (2- benzofuranyls) -3- (4- bromophenyls) propenone (1.00g, 3.06mmol), 1- in air atmosphere Phenacyl bromopyridine (1.28g, 4.58mmol) and ammonium acetate (3.53g, 45.8mmol) are dissolved in acetic acid (30mL) and two The mixed solvent of NMF (30mL), has carried out 13 hours stirring in 150 DEG C.After naturally cooling to room temperature, water is added (100mL) solid of precipitation, is collected by filtration, gained solid is carried out with water (100mL), methyl alcohol (100mL), hexane (100mL) Washing, the faint yellow solid that resulting in 2- (2- benzofuranyls) -6- (4- the bromophenyls) -4- phenylpyridines of target (is received Amount 0.810g, yield 62%).
Synthesis example -43
[chemical formula 164]
By 3- (2- benzofuranyls) -1- (4- bromophenyls) propenone (0.50g, 1.53mmol), 1- in air atmosphere Phenacyl bromopyridine (638mg, 2.29mmol) and ammonium acetate (1.77g, 22.9mmol) are dissolved in acetic acid (15mL) and two The mixed solvent of NMF (15mL), has carried out 24 hours stirring in 140 DEG C.After naturally cooling to room temperature, water is added (200mL) solid of precipitation, is collected by filtration, gained solid is carried out with water (100mL), methyl alcohol (100mL), hexane (100mL) Washing, the faint yellow solid that resulting in 4- (2- benzofuranyls) -2- (4- the bromophenyls) -6- phenylpyridines of target (is received Amount 471mg, yield 73%).
Embodiment -14
[chemical formula 165]
By 2- [3- { (4,4,5,5- tetramethyl -1,3,2- dioxaborinate -2- bases) phenyl }] -4,6- two in nitrogen stream Phenyl -1,3,5- triazines (150mg, 0.345mmol), 6- (4- bromophenyls) -4- (4- aminomethyl phenyls) -2- phenylpyridines (138mg, 0.345mmol) and tetrakis triphenylphosphine palladium (12.0mg, 0.0104mmol) are suspended in tetrahydrofuran (6mL).Xiang Qi The wet chemical (0.517mL, 1.04mmol) of middle addition 2M, has carried out 12 hours stirring in 80 DEG C.Naturally cool to room Wen Hou, adds water (40mL), and the solid of precipitation is collected by filtration.By gained solid water (30mL), methyl alcohol (30mL), hexane (30mL) washed, resulting in 2- { 4 '-[4- (4- the aminomethyl phenyls) -6- phenylpyridine -2- bases] biphenyl -3- of target Base } -4,6- diphenyl -1,3,5- triazines (compound A-1117) white powder (receipts amount 203mg, yield 93%).
1H-NMR(CDCl3)δ(ppm):2.51 (s, 3H), 7.41 (d, J=7.5Hz, 2H), 7.51-7.75 (m, 13H), 7.94-8.02 (m, 4H), 8.29 (d, J=7.5Hz, 2H), 8.42 (d, J=8.4Hz, 2H), 8.84-8.87 (m, 5H), 9.13 (brs,1H).
Embodiment -15
[chemical formula 166]
By 2- [3- { (4,4,5,5- tetramethyl -1,3,2- dioxaborinate -2- bases) phenyl }] -4,6- two in nitrogen stream Phenyl -1,3,5- triazines (150mg, 0.345mmol), 6- (4- bromophenyls) -4- (3,5- 3,5-dimethylphenyls) -2- phenylpyridines (143mg, 0.345mmol) and tetrakis triphenylphosphine palladium (12.0mg, 0.0104mmol) are suspended in tetrahydrofuran (6mL).Xiang Qi The wet chemical (0.517mL, 1.04mmol) of middle addition 2M, has carried out 12 hours stirring in 65 DEG C.Naturally cool to room Wen Hou, adds water (40mL), and the solid of precipitation is collected by filtration.By gained solid water (30mL), methyl alcohol (30mL), hexane (30mL) washed, resulting in 2- { 4 '-[4- (3,5- the 3,5-dimethylphenyl) -6- phenylpyridine -2- bases] connection of target Benzene -3- bases } -4,6- diphenyl -1,3,5- triazines (compound A-1118) white powder (receipts amount 85.8mg, yield 39%).
1H-NMR(CDCl3)δ(ppm):2.50 (s, 6H), 7.18-8.01 (m, 18H), 8.29 (d, J=7.8Hz, 2H), 8.43 (d, J=8.1Hz, 2H), 8.83-8.87 (m, 5H), 9.13 (s, 1H).
Embodiment -16
[chemical formula 167]
By 2- [3- { (4,4,5,5- tetramethyl -1,3,2- dioxaborinate -2- bases) phenyl }] -4,6- two in nitrogen stream Phenyl -1,3,5- triazines (150mg, 0.345mmol), 2- (2- benzofuranyls) -6- (4- bromophenyls) -4- phenylpyridines (147mg, 0.345mmol) and tetrakis triphenylphosphine palladium (12.0mg, 0.0104mmol) are suspended in tetrahydrofuran (6mL).Xiang Qi The wet chemical (0.517mL, 1.04mmol) of middle addition 2M, has carried out 12 hours stirring in 65 DEG C.Naturally cool to room Wen Hou, adds water (40mL), and the solid of precipitation is collected by filtration.By gained solid water (30mL), methyl alcohol (30mL), hexane (30mL) washed, resulting in target 2- 4 '-[6- (2- benzofuranyls) -4- phenylpyridine -2- bases] biphenyl - 3- yls } -4,6- diphenyl -1,3,5- triazines (compound A-1045) white powder (receipts amount 181mg, yield 80%).
1H-NMR(CDCl3)δ(ppm):7.23-7.41(m,2H),7.55-7.78(m,15H),7.98-8.04(m,5H), 8.24-8.23(m,2H),8.85-8.87(m,5H),9.13(brs,1H).
Embodiment -17
[chemical formula 168]
By 2- [3- { (4,4,5,5- tetramethyl -1,3,2- dioxaborinate -2- bases) phenyl }] -4,6- two in nitrogen stream Phenyl -1,3,5- triazines (150mg, 0.345mmol), 4- (2- benzofuranyls) -2- (4- bromophenyls) -6- phenylpyridines (147mg, 0.345mmol) and tetrakis triphenylphosphine palladium (12.0mg, 0.0104mmol) are suspended in tetrahydrofuran (5mL).Xiang Qi The wet chemical (0.517mL, 1.04mmol) of middle addition 2M, has carried out 4 hours stirring in 65 DEG C.Naturally cool to room temperature Afterwards, water (40mL) is added, the solid of precipitation is collected by filtration.By gained solid water (30mL), methyl alcohol (30mL), hexane (30mL) Washed, resulting in the 2- { 4 '-[4- (2- benzofuranyls) -6- phenylpyridine -2- bases] biphenyl -3- bases } of target - The white powder (receipts amount 180mg, yield 80%) of 4,6- diphenyl -1,3,5- triazines (compound A-685).
1H-NMR(CDCl3)δ(ppm):7.35-7.77 (m, 15H), 7.98 (brd, J=7.8Hz, 3H), 8.20 (s, 1H), 8.26 (s, 1H), 8.32 (d, J=7.2Hz, 2H), 8.46 (d, J=8.4Hz, 2H), 8.85-8.87 (m, 5H), 9.14 (s, 1H).
Synthesis example -44
[chemical formula 169]
In air atmosphere by 3- bromoacetophenones (10.00g, 0.0502mol) and 3- chlorobenzaldehydes (7.09g, Acetic acid (100mL) 0.0504mol) is dissolved in, then, the concentrated sulfuric acid (13.3mL, 0.240mol) is added dropwise, and carried out at room temperature Stir within 23 hours.After stirring, the water of 300mL is added, the solid of precipitation is collected by filtration.Gained solid is carried out with water (200mL) Washing, resulting in yellow solid (receipts amount 9.07g, the yield of 1- (3- bromophenyls) -3- (3- chlorphenyls) propenone of target 56%).
Synthesis example -45
[chemical formula 170]
By 1- (3- bromophenyls) -3- (3- chlorphenyls) propenone (9.93g, 0.0309mmol), 1- benzene in air atmosphere Formyl methyl bromopyridine (13.01g, 0.0468mol) and ammonium acetate (48.59g, 0.630mol) be suspended in acetic acid (150mL) and The mixed solvent of dimethylformamide (100mL), has carried out 16 hours stirring in 150 DEG C.After naturally cooling to room temperature, water is added (100mL), methyl alcohol (50mL), is collected by filtration the solid of precipitation.Gained solid is washed with water (100mL), methyl alcohol (100mL) Wash, resulting in white solid (C-5) (the receipts amount of 2- (3- bromophenyls) -4- (3- the chlorphenyls) -6- phenylpyridines of target 9.36g, yield 72%).
Synthesis example -46
[chemical formula 171]
2- (3- bromophenyls) -4- (3- chlorphenyls) -6- phenylpyridines (6.00g, 0.0143mol) is dissolved in argon gas stream In tetrahydrofuran (50mL), carry out 20 minutes stirring in -78 DEG C.Thereto be added dropwise n-BuLi (hexane solution, 0.0180mol), carried out 2 hours stirring.Then, add triisopropyl borate ester (4.2mL, 0.0183mol) and to have carried out 2 little When stir.Then, the sodium hydrate aqueous solution (10mL, 0.040mol) of 4M is added, has further carried out 1 hour stirring.Heat up To room temperature, water (50mL) is added in the reaction solution, and extracted using ethyl acetate (80mL).Wash with water Machine layer, and organic layer and water layer are separated.After being dehydrated to organic layer using magnesium sulfate, go out from organic layer reduced pressure concentration low Boiling component, resulting in the brown solid of 3- [4- (3- the chlorphenyls) -6- phenylpyridine -2- bases] phenylboric acid of target (receipts amount 5.00g, yield 91%).
Synthesis example -47
[chemical formula 172]
In argon gas stream by 3- [4- (3- chlorphenyls) -6- phenylpyridine -2- bases] phenylboric acid (4.56g, 9.75mmol), The chloro- 4,6- diphenyl -1,3,5- triazines (2.17g, 8.12mmol) of 2- and tetrakis triphenylphosphine palladium (0.281g, 0.24mmol) are outstanding Float on tetrahydrofuran (50mL).The wet chemical (12.2mL, 24.4mmol) of 2M is added thereto to, and is carried out in 70 DEG C Stir within 64 hours.After naturally cooling to room temperature, water (30mL) is added, the solid of precipitation is collected by filtration, using water (100mL), first Alcohol (100mL), hexane (100mL) are washed to solid.2 recrystallizations (toluene) of solid Jing are carried out after purification, Gained crude product is dissolved in into toluene (300mL), diatomite filtration is carried out, and reduced pressure concentration has been carried out to filtrate.To from filtrate In 1 recrystallization (toluene) of the further Jing of crude product that obtains and purified, further with column chromatography (chloroform:Hexane) enter Row purifying, resulting in 2- { [4- (3- chlorphenyls) -6- phenylpyridine -2- bases] phenyl -3- bases } -4, the 6- hexichol of target The white powder (receipts amount 1.41g, yield 73%) of base -1,3,5- triazines.
Embodiment -18
[chemical formula 173]
By 2- { [4- (3- chlorphenyls) -6- phenylpyridine -2- bases] phenyl -3- bases } -4,6- diphenyl -1 in argon gas stream, 3,5- triazines (1.29g, 2.25mmol), 9- phenanthrene boric acid (0.707g, 3.18mmol), acid chloride (38mg, 0.17mmol) and 2- Dicyclohexylphosphontetrafluoroborate -2 ', 4 ', 6 '-tri isopropyl biphenyl (0.149g, 0.31mmol) is suspended in tetrahydrofuran (67mL), and to it The wet chemical (3.2mL, 6.4mmol) of middle dropwise addition 2M, has carried out 118 hours stirring in 75 DEG C.Naturally cool to room temperature Afterwards, toluene (50mL) is added in the reaction solution, diatomite filtration is carried out, reduced pressure concentration has been carried out to filtrate.To the filtrate Middle addition water (50mL), methyl alcohol (50mL), hexane (100mL), are collected by filtration the solid of precipitation.By gained solid water (50mL), methyl alcohol (50mL), hexane (50mL) are washed.Solid Jing is recrystallized into (toluene) and is purified, enter one Step utilizes column chromatography (chloroform:Hexane) purified, resulting in 2- ({ 4- [3- (9- phenanthryl) the phenyl] -6- phenyl of target Pyridine -2- bases } phenyl -3- bases) -4,6- diphenyl -1,3,5- triazines (A-1422) white solid (receipts amount 1.07g, yield 67%).
1H-NMR(CDCl3)δ(ppm):7.46-7.76(m,16H),7.82(s,1H),7.91-7.95(m,2H),7.98- 8.04 (m, 2H), 8.07 (brs, 1H), 8.16 (brs, 1H), 8.30-8.34 (d, J=7.5Hz, 2H), 8.47-8.51 (d, J= 7.5Hz,1H),8.75-8.87(m,7H),9.65(m,1H).
The Tg of compound A-1422 is 125 DEG C.
Synthesis example -48
[chemical formula 174]
In air atmosphere by 3- chloro-acetophenones (10.01g, 0.0648mol) and 3- bromobenzaldehydes (11.98g, Acetic acid (100mL) 0.0647mol) is dissolved in, the concentrated sulfuric acid (17.1mL, 0.309mol) is added dropwise thereto, and carried out at room temperature 22 hours stir.Then, the water of 400mL is added, the solid of precipitation is collected by filtration.Gained solid is carried out with water (300mL) Washing, resulting in yellow solid (receipts amount 20.69g, the receipts of 3- (3- bromophenyls) -1- (3- chlorphenyls) propenone of target Rate 99%).
Synthesis example -49
[chemical formula 175]
By 3- (3- bromophenyls) -1- (3- chlorphenyls) propenone (12.12g, 0.0377mmol), 1- benzene in air atmosphere Formyl methyl bromopyridine (12.97g, 0.0466mol) and ammonium acetate (49.69g, 0.645mol) be suspended in acetic acid (150mL) and The mixed solvent of dimethylformamide (100mL), has carried out 24 hours stirring in 150 DEG C.After naturally cooling to room temperature, water is added (100mL), methyl alcohol (50mL), is collected by filtration the solid of precipitation.Gained solid is washed with water (100mL), methyl alcohol (100mL) Wash, resulting in white solid (the receipts amount of 4- (3- the bromophenyls) -2- (3- chlorphenyls) -6- phenylpyridines (C-12) of target 7.87g, yield 50%).
Synthesis example -50
[chemical formula 176]
4- (3- bromophenyls) -2- (3- chlorphenyls) -6- phenylpyridines (5.00g, 0.0119mol) is dissolved in argon gas stream In tetrahydrofuran (30mL), carry out 10 minutes stirring in -78 DEG C.Thereto be added dropwise n-BuLi (hexane solution, 0.0180mol) and carry out after stirring in 5 hours, further add triisopropyl borate ester (4.2mL, 0.0157mol) and to carry out Stir within 22 hours.Then, the sodium hydrate aqueous solution (3.8mL, 0.017mol) of 4M is added, and has carried out 20 minutes stirring.Connect , water (50mL) is added in the reaction solution, extracted using ethyl acetate (80mL).Wash organic layer with water, and Organic layer and water layer are separated.After being dehydrated to organic layer using magnesium sulfate, from organic layer reduced pressure concentration go out low boiling into Point, resulting in brown solid (the receipts amount of 3- [2- (3- the chlorphenyls) -6- phenylpyridine -4- bases] phenylboric acid of target 4.31g, yield 94%).
Synthesis example -51
[chemical formula 177]
In argon gas stream by 3- [2- (3- chlorphenyls) -6- phenylpyridine -4- bases] phenylboric acid (4.02g, 0.0104mol), the chloro- 4,6- diphenyl -1,3,5- triazines (2.34g, 8.74mmol) of 2- and tetrakis triphenylphosphine palladium (0.32g, 0.24mmol) it is suspended in tetrahydrofuran (50mL).The wet chemical (13.0mL, 26.0mmol) of 2M is added thereto to, in 80 DEG C have carried out 20 hours stirring.After naturally cooling to room temperature, methyl alcohol (180mL) is added, the solid of precipitation, and profit is collected by filtration Solid is washed with water (100mL), methyl alcohol (100mL), hexane (100mL).The solid dissolving is made in toluene (150mL), diatomite filtration is carried out, reduced pressure concentration has been carried out to filtrate.The further Jing of crude product to obtaining from filtrate 1 time Recrystallize (toluene) and purified, further with column chromatography (chloroform:Hexane) purified, resulting in the 2- of target The white powder of { [2- (3- chlorphenyls) -6- phenylpyridine -4- bases] phenyl -3- bases } -4,6- diphenyl -1,3,5- triazines (is received Amount 1.88g, yield 38%).
Embodiment -19
[chemical formula 178]
By 2- { [2- (3- chlorphenyls) -6- phenylpyridine -4- bases] phenyl -3- bases } -4,6- diphenyl -1 in argon gas stream, 3,5- triazines (1.00g, 1.75mmol), 9- phenanthrene boric acid (0.782g, 3.52mmol), acid chloride (13.6mg, 0.06mmol) and 2- dicyclohexylphosphontetrafluoroborates -2 ', 4 ', 6 '-tri isopropyl biphenyl (35.6mg, 0.075mmol) is suspended in tetrahydrofuran (60mL), is added dropwise The wet chemical (1.8mL, 3.6mmol) of 2M, has carried out 28 hours stirring in 75 DEG C.After naturally cooling to room temperature, to this Reaction solution is filtered, and thus removes black residue, and has carried out reduced pressure concentration to gained filtrate.Gained solid Jing is tied again Brilliant (toluene) and purified, further with column chromatography (chloroform:Hexane) purified, resulting in the 2- ({ 2- of target [3- (9- phenanthryl) phenyl] -6- phenylpyridine -4- bases } phenyl -3- bases) -4,6- diphenyl -1,3,5- triazines (A-1282) it is white Color solid (receipts amount 0.96g, yield 77%).
1H-NMR(CDCl3)δ(ppm):7.44-7.76 (m, 16H), 7.83 (s, 1H), 7.93 (d, J=7.8Hz, 1H), 7.98 (d, J=7.7Hz, 1H), 8.02 (d, J=8.3Hz, 1H), 8.06 (m, 1H), 8.09 (m, 1H), 8.25-8.28 (m, 2H),8.37-8.41(m,1H),8.42(m,1H),8.75-8.83(m,6H),8.88(m,1H),9.11(m,1H).
The Tg of compound A-1282 is 127 DEG C.
Hereinafter, recorded for element evaluation.
The structural formula and its abbreviation of the compound evaluated for element is as follows.
[chemical formula 179]
Device embodiments 1
Used as substrate, indium oxide-tin (ITO) film (thickness 110nm) for having used 2mm wide is patterned into striated and forms The glass substrate with ito transparent electrode.After the substrate is washed with isopropanol, table is carried out by UV ozone cleaning Face is processed.The vacuum evaporation of each layer is carried out using vacuum vapour deposition to the substrate after cleaning, profile has been made as shown in Figure 1 Light-emitting area 4mm2Organic electroluminescent device.It should be noted that each organic material is carried out using resistance heating manner Film forming.
First, import above-mentioned glass substrate into vacuum evaporation groove, and be decompressed to 1.0 × 10-4Pa。
Thereafter, in FIG using on 1 glass substrate with ito transparent electrode for representing successively lamination as organic compound The hole injection layer 2 of layer, charge generation layer 3, hole transmission layer 4, luminescent layer 5, electron transfer layer 6 and cathode layer 7, while to appointing One layer has carried out film forming using vacuum evaporation.
As hole injection layer 2, the HIL that have passed through sublimation purification 65nm film forming is carried out into the speed of 0.15nm/ seconds.
As charge generation layer 3, the HAT that have passed through sublimation purification 5nm film forming is carried out into the speed of 0.05nm/ seconds.
As hole transmission layer 4, HTL 10nm film forming is carried out into the speed of 0.15nm/ seconds.
As luminescent layer 5, by EML-1 and EML-2 with 95:5 ratio has carried out 25nm film forming (film forming speed 0.18nm/ Second).
As electron transfer layer 6,2- { 4 '-[2- (2- the naphthyls) -6- phenylpyridine -4- bases] that will synthesize in embodiment -1 Biphenyl -3- bases } -4,6- diphenyl -1,3,5- triazines (compound A-2) and Liq is with 50:The ratio of 50 (weight ratios) is carried out 30nm film forming (film forming speed 0.15nm/ seconds).
Finally, metal mask is configured in the mode orthogonal with ITO stripeds, film forming cathode layer 7.For cathode layer 7, will Silver/magnesium (weight compares 1/10) and silver are successively being respectively 80nm (film forming speed 0.5nm/ seconds) and 20nm (film forming speed 0.2nm/ Second) film forming, make double-decker.
The thickness of each layer is determined using contact pin type film thickness measuring meter (DEKTAK).
Further, in oxygen and moisture concentration to be sealed to the element in the nitrogen atmosphere glove box of below 1ppm. Sealing employs closure and above-mentioned substrate for film deposition epoxy type ultraviolet curable resin (the Nagase ChemteX companies of glass system System).
Organic electroluminescent device to making as described above applies DC current, using TOPCON company systems The luminance meter of LUMINANCE METER (BM-9) have rated the characteristics of luminescence.As the characteristics of luminescence, determine with 10mA/cm2Electricity Current density flows through voltage (V), the current efficiency (cd/A) during electric current, and the component life (h) when determining continuous illumination.Need Illustrate, for the component life (h) of table 1, determine with initial stage brightness 800cd/m2Carry out when driving made element Brightness decay time during continuous illumination, and determine until brightness (cd/m2) reduce 10% till required time.For Component life, on the basis of the component life (h) in element reference example 1 described later (100) are worth.As a result it is as shown in table 1.
Device embodiments 2
2- { 4 '-[the 4- synthesized in embodiment -2 have been used except in device embodiments 1, replacing compound A-2 (2- naphthyls) -6- phenylpyridine -2- bases] biphenyl -3- bases } beyond -4,6- diphenyl -1,3,5-triazines (compound A-362), profit Organic electroluminescent device is made with the identical method of device embodiments 1, and has been evaluated.As a result it is as shown in table 1.Need It is noted that for component life, on the basis of component life (h) is determined, by the component life of element reference example 1 Relative value when being set to 100 is represented.
Device embodiments 3
2- { 4 '-[the 6- synthesized in embodiment -3 have been used except in device embodiments 1, replacing compound A-2 (2- naphthyls) -4- phenylpyridine -2- bases] biphenyl -3- bases } beyond -4,6- diphenyl -1,3,5-triazines (compound A-722), profit Organic electroluminescent device is made with the identical method of device embodiments 1, and has been evaluated.As a result it is as shown in table 1.Need It is noted that for component life, on the basis of component life (h) is determined, by the component life of element reference example 1 Relative value when being set to 100 is represented.
Device embodiments 4
2- { 4 '-[the 2- synthesized in embodiment -6 have been used except in device embodiments 1, replacing compound A-2 (1- naphthyls) -6- phenylpyridine -4- bases] biphenyl -3- bases } beyond -4,6- diphenyl -1,3,5-triazines (compound A-4), utilize Organic electroluminescent device is made with the identical method of device embodiments 1, and has been evaluated.As a result it is as shown in table 1.Need Illustrate, for component life, on the basis of component life (h) is determined, the component life of element reference example 1 is set For 100 when relative value represent.
Device embodiments 5
2- { 4 '-[the 4- synthesized in embodiment -7 have been used except in device embodiments 1, replacing compound A-2 (1- naphthyls) -6- phenylpyridine -2- bases] biphenyl -3- bases } beyond -4,6- diphenyl -1,3,5-triazines (compound A-364), profit Organic electroluminescent device is made with the identical method of device embodiments 1, and has been evaluated.As a result it is as shown in table 1.Need It is noted that for component life, on the basis of component life (h) is determined, by the component life of element reference example 1 Relative value when being set to 100 is represented.
Device embodiments 6
2- { 4 '-[the 4- synthesized in embodiment -8 have been used except in device embodiments 1, replacing compound A-2 (1- naphthyls) -6- (2- naphthyls) pyridine -2- bases] biphenyl -3- bases -4,6- diphenyl -1,3,5- triazines (compound A-365) with Outward, organic electroluminescent device has been made using with the identical method of device embodiments 1, and has been evaluated.As a result such as the institute of table 1 Show.It should be noted that for component life, on the basis of component life (h) is determined, by the unit of element reference example 1 Relative value when the part life-span is set to 100 is represented.
Device embodiments 7
4, the 6- hexichol synthesized in embodiment -9 has been used except in device embodiments 1, replacing compound A-2 Beyond base -2- [4 '-(4,6- hexichol yl pyridines -2- bases)-biphenyl -3- bases] -1,3,5-triazines (compound A-721), using with The identical method of device embodiments 1 has made organic electroluminescent device, and is evaluated.As a result it is as shown in table 1.Need It is bright, for component life, on the basis of component life (h) is determined, the component life of element reference example 1 is set to Relative value when 100 is represented.
Device embodiments 8
2- ({ 4- [the 3- synthesized in embodiment -18 have been used except in device embodiments 1, replacing compound A-2 (9- phenanthryl) phenyl] -6- phenylpyridine -2- bases } phenyl -3- bases) -4,6- diphenyl -1,3,5- triazines (compound A-1422) In addition, organic electroluminescent device has been made using with the identical method of device embodiments 1, and has been evaluated.As a result such as table 1 It is shown.It should be noted that for component life, on the basis of component life (h) is determined, by element reference example 1 Relative value when component life is set to 100 is represented.
Device embodiments 9
2- ({ 2- [the 3- synthesized in embodiment -19 have been used except in device embodiments 1, replacing compound A-2 (9- phenanthryl) phenyl] -6- phenylpyridine -4- bases } phenyl -3- bases) -4,6- diphenyl -1,3,5- triazines (compound A-1282) In addition, organic electroluminescent device has been made using with the identical method of device embodiments 1, and has been evaluated.As a result such as table 1 It is shown.It should be noted that for component life, on the basis of component life (h) is determined, by element reference example 1 Relative value when component life is set to 100 is represented.
Element reference example 1
Use described in Japanese Unexamined Patent Publication 2011-063584 except in device embodiments 1, replacing compound A-2 Beyond 2- [5- (9- phenanthryl) -4 '-(2- pyrimidine radicals) biphenyl -3- bases] -4,6- diphenyl -1,3,5-triazines (ETL-2), using with The identical method of device embodiments 1 has made organic electroluminescent device, and is evaluated.As a result it is as shown in table 1.Need Bright, for component life, on the basis of component life (h) is determined, the component life with this element reference example 1 is as base Quasi- value (100).
[table 1]
Compound Voltage (V) Current efficiency (cd/A) Component life
Device embodiments 1 A-2 3.97 5.01 223
Device embodiments 2 A-362 3.73 5.07 154
Device embodiments 3 A-722 3.97 5.10 165
Device embodiments 4 A-4 4.71 5.97 233
Device embodiments 5 A-364 4.08 6.13 140
Device embodiments 6 A-365 3.89 6.14 149
Device embodiments 7 A-721 3.77 4.59 126
Device embodiments 8 A-1422 4.13 5.01 84
Device embodiments 9 A-1282 4.76 5.07 116
Element reference example 1 ETL-2 4.50 4.15 100
The present invention has been described in detail above by reference to specific embodiment, but to those skilled in the art Nature in the case of the spirit and scope without departing from the present invention, it is understood that can also add various modifications and amendment.
It should be noted that here citing the Japanese patent application 2014-136188 filed an application on July 1st, 2014 Number, the Japanese patent application 2014-178231 filed an application for 2nd in September in 2014, file an application on December 25th, 2014 Japanese patent application 2014-262107 specification and the Japanese patent application filed an application for 19th for 2 months in 2015 Full content in the specification of No. 2015-31113, claims, accompanying drawing and summary, includes disclosed in description of the invention Content.
Industrial applicibility
The excellent heat resistance of the film quality of the triaizine compounds (1) of the present invention, therefore by using the compound, it is possible to provide it is long The excellent organic electroluminescent device of life-span property and luminous efficiency.
In addition, the triaizine compounds (1) of the present invention are used as the excellent organic electroluminescent device of low driving voltage using Electron transport material.Further, according to the present invention, it is possible to provide the excellent organic electroluminescent device of power consumption.
In addition, good thermal stability of the triaizine compounds (1) of the present invention in sublimation purification, therefore it is pure to provide distillation The few material of the impurity of the reason for element deterioration that is operational excellent, becoming organic electroluminescent device of change.In addition, of the invention Triaizine compounds (1) evaporation film excellent in stability, therefore long-life organic electroluminescent device can be provided.
In addition, by the electron transport ability of the film that formed of triaizine compounds (1) of the present invention, hole blocking ability, resistance to Oxidation-reduction quality, resistance to water, oxygen resistence, Electron Injection Characteristics etc. are excellent, thus as organic electroluminescent device material and It is useful, it is useful as electron transport material, hole barrier materials, light emitting host material etc..Especially as electric transmission material Material is useful when using.In addition, the triaizine compounds (1) of the present invention are wide bandgap compound, therefore can be applied not only to Traditional fluorescent element purposes, additionally it is possible to suitable for phosphorescent element.

Claims (17)

1. triaizine compounds shown in formula (1),
In formula (1),
Ar1Phenyl or naphthyl is represented independently of one another, and these groups are optionally replaced by fluorine atom, methyl or phenyl,
Ar2And Ar3Represent independently of one another optionally link and/or condensed ring carbon number 6～24 aromatic hydrocarbyl, only by 6 yuan Ring constitute and optionally link and/or condensed ring carbon number 3～25 nitrogenous heteroaromatic group or by selected from H, C, O and S group Into atom group in atomic building and optionally link and/or condensed ring carbon number 3～25 heteroaromatic group, and these bases Group is optionally replaced by the alkoxyl of fluorine atom, the alkyl of carbon number 1～4 or carbon number 1～4,
R5、R6And R7The alkyl of carbon number 1～4 is represented independently of one another,
N represents 0 or 1,
P represent 0,1,2,3 or 4, p be 2,3 or 4 in the case of, R5Can with different from each other,
Q represent 0,1,2,3 or 4, q be 2,3 or 4 in the case of, R6Can with different from each other,
R represent 0,1 or 2, r be 2 in the case of, 2 R7Can with different from each other,
Z1And Z2Nitrogen-atoms or C-H, also, Z are represented independently of one another1Or Z2In any one represent nitrogen-atoms, another one table Show C-H.
2. triaizine compounds according to claim 1, wherein,
Ar2And Ar3Be each independently optionally link and/or condensed ring carbon number 6～24 aromatic hydrocarbyl, only by 6 yuan of rings Constitute and optionally link and/or condensed ring carbon number 3～25 nitrogenous heteroaromatic group or by constituting selected from H, C, O and S Atom group in atomic building and optionally link and/or condensed ring carbon number 3～25 heteroaromatic group.
3. triaizine compounds according to claim 1, wherein,
Ar2And Ar3It is each independently phenyl, xenyl, naphthylphenyl, phenanthryl phenyl, fluoranthene base phenyl, pyridinylphenyl, quinoline Quinoline base phenyl, thienyl phenyl, furyl phenyl, benzothienyl phenyl, benzofuranyl phenyl, dibenzothiophenes base benzene Base, dibenzofuran group phenyl, naphthyl, pyridine radicals, benzothienyl, benzofuranyl, phenanthryl, anthryl, dibenzothiophenes base, Or dibenzofuran group, and these groups are optionally by fluorine atom or methyl replacement.
4. triaizine compounds according to claim 1, wherein,
Ar2And Ar3It is each independently phenyl, tolyl, 3,5-dimethylphenyl, xenyl, naphthylphenyl, phenanthryl phenyl, pyridine radicals Phenyl, dibenzothiophenes base phenyl, dibenzofuran group phenyl, naphthyl, pyridine radicals, benzothienyl, benzofuranyl, phenanthrene Base, anthryl, dibenzothiophenes base or dibenzofuran group.
5. triaizine compounds according to claim 1, wherein, Ar1It is each independently phenyl or naphthyl, and these groups Optionally replaced by methyl or phenyl.
6. triaizine compounds according to claim 1, wherein, Ar1It is each independently phenyl, naphthyl or xenyl.
7. triaizine compounds according to claim 1, wherein, Ar1For phenyl.
8. triaizine compounds according to claim 1, wherein, p=q=r=0.
9. the manufacture method of the triaizine compounds described in claim 1, it includes：
The compound shown in the compound and formula (13) shown in formula (12) is made in the presence of palladium catalyst, and there is alkali Under conditions of or do not exist under conditions of alkali, sequentially or simultaneously carry out coupling reaction,
In formula (11), (12) and (13),
Ar1、Ar2、Ar3、R5、R6、R7、p、q、r、Z1And Z2It is synonymous with claim 1,
Y represents leaving group,
M represents ZnR1、MgR2、Sn(R3)3Or B (OR4)2, wherein, R1And R2Represent that chlorine atom, bromine atoms or iodine are former independently of one another Son, R3Represent the alkyl or phenyl of carbon number 1～4, R4Represent hydrogen atom, the alkyl of carbon number 1～4 or phenyl, B (OR4)2In 2 R4It is optionally identical or different, in addition, 2 R4Also optionally it is integrally formed and the shape comprising oxygen atom and boron atom Cyclization.
10. the manufacture method of the triaizine compounds described in claim 1, it includes：
The compound shown in the compound and formula (15) shown in formula (14) is made in the presence of palladium catalyst, and there is alkali Under conditions of or do not exist and carry out under conditions of alkali coupling reaction,
In formula (11), (14) and (15),
Ar1、Ar2、Ar3、R5、R6、R7、p、q、r、Z1And Z2It is synonymous with claim 1,
Y represents leaving group,
M represents ZnR1、MgR2、Sn(R3)3Or B (OR4)2, wherein, R1And R2Represent that chlorine atom, bromine atoms or iodine are former independently of one another Son, R3Represent the alkyl or phenyl of carbon number 1～4, R4Represent hydrogen atom, the alkyl of carbon number 1～4 or phenyl, B (OR4)2In 2 R4It is optionally identical or different, in addition, 2 R4Can also be integrally formed and the shape comprising oxygen atom and boron atom Cyclization.
The manufacture method of the triaizine compounds described in 11. claims 1, it includes：
Make the compound shown in the compound and formula (23) shown in formula (22) in the presence of palladium catalyst sequentially or simultaneously Carry out coupling reaction,
In formula (21), (22) and (23),
Ar1、Ar2、Ar3、R5、R7、p、r、Z1And Z2It is synonymous with claim 1,
Y represents leaving group,
M represents ZnR1、MgR2、Sn(R3)3Or B (OR4)2, wherein, R1And R2Represent that chlorine atom, bromine atoms or iodine are former independently of one another Son, R3Represent the alkyl or phenyl of carbon number 1～4, R4Represent hydrogen atom, the alkyl of carbon number 1～4 or phenyl, B (OR4)2In 2 R4It is optionally identical or different, in addition, 2 R4Can also be integrally formed and the shape comprising oxygen atom and boron atom Cyclization.
The manufacture method of the triaizine compounds described in 12. claims 1, it includes：
Make the compound shown in the compound and formula (25) shown in formula (24) in the presence of palladium catalyst sequentially or simultaneously Carry out coupling reaction,
In formula (21), (24) and (25),
Ar1、Ar2、Ar3、R5、R7、p、r、Z1And Z2It is synonymous with claim 1,
Y represents leaving group,
M represents ZnR1、MgR2、Sn(R3)3Or B (OR4)2, wherein, R1And R2Represent that chlorine atom, bromine atoms or iodine are former independently of one another Son, R3Represent the alkyl or phenyl of carbon number 1～4, R4Represent hydrogen atom, the alkyl of carbon number 1～4 or phenyl, B (OR4)2In 2 R4It is optionally identical or different, in addition, 2 R4Can also be integrally formed and the shape comprising oxygen atom and boron atom Cyclization.
The manufacture method of the triaizine compounds described in 13. claims 1, it includes：
Make the compound shown in formula (26), formula (28) and formula (30) that coupling reaction is carried out in the presence of palladium catalyst,
Ar4-M2 (30)
In formula (26), (28) and (30),
Ar1、Ar2、Ar3、R5、R7, it is synonymous in p and r and claim 1,
Ar4Represent the optional link of carbon number 6～18 and/or the aromatic hydrocarbyl of condensed ring or the carbon original being only made up of 6 yuan of rings The optional link of subnumber 3～19 and/or the nitrogenous heteroaromatic group of condensed ring, and these substituents are optionally by fluorine atom, carbon atom The alkyl of number 1～4 or the alkoxyl of carbon number 1～4 replace, Z3、Z4And Z5Nitrogen-atoms or C-H are represented independently of one another, and And, Z3、Z4And Z5In any one represent nitrogen-atoms, remaining both represent C-H,
X1And X2Chlorine atom, bromine atoms or atomic iodine, also, X are represented independently of one another1And X2It is bromine atoms when both are different,
M1And M2ZnR is represented independently of one another1、MgR2、Sn(R3)3Or B (OR4)2, wherein, R1And R2Represent that chlorine is former independently of one another Son, bromine atoms or atomic iodine, R3Represent the alkyl or phenyl of carbon number 1～4, R4Represent hydrogen atom, carbon number 1～4 Alkyl or phenyl, B (OR4)2In 2 R4It is optionally identical or different, in addition, 2 R4Can also be integrally formed and former comprising oxygen Son and boron atom and form ring.
The manufacture method of the triaizine compounds described in 14. claims 1, it includes：Make formula (33), formula (22) and formula (30) compound shown in carries out coupling reaction in the presence of palladium catalyst,
Ar4-M2 (30)
In formula (33), (22) and (30),
Ar1、Ar2、Ar3、R5、R7, it is synonymous in p and r and claim 1,
Ar4Represent the optional link of carbon number 6～18 and/or the aromatic hydrocarbyl of condensed ring or the carbon original being only made up of 6 yuan of rings The optional link of subnumber 3～19 and/or the nitrogenous heteroaromatic group of condensed ring, and these substituents are optionally by fluorine atom, carbon atom The alkyl of number 1～4 or the alkoxyl of carbon number 1～4 replace,
Z3、Z4And Z5Nitrogen-atoms or C-H, also, Z are represented independently of one another3、Z4And Z5In any one represent nitrogen-atoms, its It is remaining that both represent C-H,
X1And X2Chlorine atom, bromine atoms or atomic iodine, also, X are represented independently of one another1And X2It is bromine atoms when both are different,
M1And M2ZnR is represented independently of one another1、MgR2、Sn(R3)3Or B (OR4)2, wherein, R1And R2Represent that chlorine is former independently of one another Son, bromine atoms or atomic iodine, R3Represent the alkyl or phenyl of carbon number 1～4, R4Represent hydrogen atom, carbon number 1～4 Alkyl or phenyl, B (OR4)2In 2 R4It is optionally identical or different, in addition, 2 R4Can also be integrally formed and former comprising oxygen Son and boron atom and form ring.
Pyridine compounds shown in 15. formulas (26), it is the compound described in claim 13,
In formula (26),
R5、R7, it is synonymous in p and r and claim 13,
Z3、Z4And Z5Nitrogen-atoms or C-H, also, Z are represented independently of one another3、Z4And Z5In any one represent nitrogen-atoms, its It is remaining that both represent C-H,
X1And X2Chlorine atom, bromine atoms or atomic iodine, also, X are represented independently of one another1And X2It is bromine atoms when both are different.
16. material for organic electroluminescence device, it includes the triaizine compounds described in claim 1.
17. organic electroluminescent device electron transport materials, it includes the triaizine compounds described in claim 1.
CN201580043586.2A 2014-07-01 2015-07-01 Triazine compound, method for producing same, and application for same Pending CN106573912A (en)

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