CN109053547A - A kind of organic electroluminescence device - Google Patents

A kind of organic electroluminescence device Download PDF

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CN109053547A
CN109053547A CN201810789209.9A CN201810789209A CN109053547A CN 109053547 A CN109053547 A CN 109053547A CN 201810789209 A CN201810789209 A CN 201810789209A CN 109053547 A CN109053547 A CN 109053547A
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organic electroluminescence
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CN109053547B (en
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蔡辉
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Changchun Haipurunsi Technology Co Ltd
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Changchun Haipurunsi Technology Co Ltd
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Abstract

The present invention provides a kind of organic electroluminescence device, is related to technical field of organic electroluminescence.The present invention has the hole transmission layer and/or luminous auxiliary layer of specific compound composition by design, electron transfer layer is to obtain organic electroluminescence device of the present invention, electron transfer rate is improved by the combination, the active balance injection rate in hole and electronics, carrier is realized in the injection balance of luminescent layer, avoid electron transfer layer, device lifetime caused by the heat localization of electron transfer layer and luminous bed boundary deteriorates, its organic electroluminescence device has the advantages that luminous efficiency height and long service life, it is high to efficiently solve organic electroluminescence device starting voltage, and the low problem low with luminous efficiency of service life caused by carrier injection imbalance.

Description

A kind of organic electroluminescence device
Technical field
The present invention relates to technical field of organic electroluminescence, and in particular to a kind of organic electroluminescence device.
Background technique
In recent years, OLED is widely applied in display field, and compared with LCD display technology, OLED is not necessarily to backlight, Can self-luminous, voltage characteristic, light emission luminance, luminous efficiency, device weight, response speed and in terms of have There is significant advantage, and because of its low cost potential, becomes panel display technologies most potential at present.
Organic electroluminescence device is as Dual Implantations type device, by applying voltage, Injection Current, electronics at yin-yang both ends Pass through the organic matter layer that luminous organic material is formed with hole, is finally combined in luminescent layer and form exciton, exciton returns to stable Ground state is to radioluminescence, wherein its structure of typical organic electroluminescence device is to generally comprise cathode, anode and in electricity Organic matter layer between pole.The composition of device includes transparent ITO anode, hole injection layer (HIL), hole transmission layer (HTL), hair Photosphere (EL), electron transfer layer (ETL), electron injecting layer (EIL), cathode etc..
All in all, the direction of the following OLED be develop high efficiency, high brightness, the long-life, low cost white light parts and Full color display device, but the technological industrialization process still faces many critical issues, if electronics is in electron injection and transmission Transmission speed in functional layer is slower, lower than hole in hole injection and transfer function interval velocity, to cause to carry in luminescent layer Stream mismatches, and transmission of the exciton in electron transfer layer side causes unnecessary energy accumulation and non-radiative energy to dissipate, thus The reduction of device efficiency and the shortening in service life are caused, therefore develop one kind to reduce carrier transport mistake with equilbrium carrier Non-radiative energy dissipates in journey, obtains that a kind of driving voltage is low, luminous efficiency is high, organic electroluminescence device with long service life As urgent problem to be solved.
Summary of the invention
The object of the present invention is to provide a kind of organic electroluminescence device, organic electroluminescence device provided by the invention is adopted It is matched with the hole transmission layer of specified chemical structure and/or luminous auxiliary layer, electron transfer layer, it is flat to reach carrier injection The purpose of weighing apparatus has the advantages that driving voltage is low, luminous efficiency is high, long service life.
The present invention provides a kind of organic electroluminescence device, including cathode, anode, it is located at the cathode and the anode Between organic matter layer, the organic matter layer includes hole transmission layer and/or luminous auxiliary layer, electron transfer layer, the sky Contain chemical formula (I) compound represented in cave transport layer and/or luminous auxiliary layer:
Wherein, L1、L2、L3It does not take independently selected from singly-bound, the divalent aryl of substituted or unsubstituted C6~C30, substitution or One of the divalent heteroaryl radical of C3~C30 in generation；Ar1、Ar3It does not take independently selected from substituted or unsubstituted phenyl, substitution or The naphthalene in generation, substituted or unsubstituted anthryl, substituted or unsubstituted fluorenyl, one in two fluorenyl of substituted or unsubstituted spiral shell Kind；Ar2Selected from substituted or unsubstituted carbazyl.
Preferably, the L1、L2、L3Independently selected from singly-bound, substituted or unsubstituted phenyl, substituted or unsubstituted One of naphthalene, substituted or unsubstituted xenyl.
Preferably, the Ar2It is as follows group:
Wherein, R1Selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 alkoxy, replace or One of unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl；
R2、R3At each occurrence identical or differently selected from hydrogen atom, D-atom, halogen atom, C1~C10 alkyl, The alkoxy of C1~C10, the aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C3~C30 heteroaryl in It is a kind of；Or the R2、R3The condensed cyclization of both middle arbitrary neighborhoods；
A is selected from 0 to 4 integer, and b is selected from 0 to 3 integer.
Preferably, the Ar2Selected from one of following group:
Preferably, Ar1、Ar3Independently selected from one of following group:
Wherein, R4、R5、R6、R7It is selected from hydrogen atom, D-atom, halogen atom, C1 identical or differently at each occurrence The alkyl of~C10, the alkoxy of C1~C10, the aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C3~ One of heteroaryl of C30；Or the R4、R5、R6、R7The condensed cyclization of both middle arbitrary neighborhoods；C, d, e, f are independent is selected from 0 To 4 integer.
Preferably, Ar1、Ar3Independently selected from one of following group:
Preferably, the electron transfer layer contains chemical formula (II) compound represented:
Wherein, Ar4、Ar5、Ar6Aryl, substituted or unsubstituted C3 independently selected from substituted or unsubstituted C6~C65 One of the heteroaryl of~C65, and Ar4、Ar5、Ar6In at least one be selected from following group:
Wherein, R8、R9Alkyl, substituted or unsubstituted C6~C30 independently selected from substituted or unsubstituted C1~C10 Aryl, one of the heteroaryl of substituted or unsubstituted C6~C30；R10Selected from hydrogen atom, substituted or unsubstituted C1~ One of the alkyl of C10, aryl of substituted or unsubstituted C6~C30.
Preferably, Ar4、Ar5、Ar6At least one is selected from following group:
Wherein, R8、R9Independently selected from methyl, ethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, take Generation or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene Base, substituted or unsubstituted base, substituted or unsubstituted ferrosin base, substituted or unsubstituted pyridyl group, substitution do not take The pyrimidine radicals in generation, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazine radical, takes substituted or unsubstituted pyrazinyl It is generation or unsubstituted pyrrole radicals, substituted or unsubstituted benzopyrrole base, substituted or unsubstituted triazolyl, substituted or unsubstituted Thienyl, substituted or unsubstituted furyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuran Base, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted quinoline One of base, substituted or unsubstituted isoquinolyl, substituted or unsubstituted indyl；R10Selected from hydrogen atom, methyl, second Base, isopropyl or tert-butyl.
Preferably, Ar5、Ar6It is identical, it is selected from following group:
Wherein, R8、R9Independently selected from methyl, ethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, take Generation or unsubstituted anthryl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted pyrazine One of base；R10Selected from hydrogen atom, methyl, ethyl, isopropyl or tert-butyl.
Preferably, Ar4Selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene Base, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted acridinyl, substitution do not take Phenoxazine base, substituted or unsubstituted phenothiazinyl, the substituted or unsubstituted phenoxazine thiophene base, substituted or unsubstituted fluorenes in generation Base, substituted or unsubstituted pyrenyl, substituted or unsubstituted ferrosin base, replaces or does not take substituted or unsubstituted carbazyl The base in generation, substituted or unsubstituted acenaphthenyl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substitution or Unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazine radical, substituted or unsubstituted pyrroles Base, substituted or unsubstituted benzopyrrole base, substituted or unsubstituted triazolyl, substituted or unsubstituted thienyl, substitution or It is unsubstituted furyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted Dibenzothiophene, one of substituted or unsubstituted dibenzofuran group.
Beneficial effects of the present invention:
The present invention provides a kind of organic electroluminescence device, and the present invention passes through the hole that will be made of specific compound (I) Transport layer and/or luminous auxiliary layer, and the electron transfer layer being made of specific compound (II), carry out adaptation group for the two It closes, to obtain a kind of organic electroluminescence device of the present invention.
Organic electroluminescence device of the invention is used as hole transmission layer and/or luminous auxiliary layer using compound (I), Derivative simultaneously containing fluorenes, two fluorenes of spiral shell and carbazole, fluorenes, spirobifluorene derivative rigidity planar inline benzene unit make it have High thermal stability and chemical stability, the rigid planar structure and big pi-conjugated system that carbazole compound has, makes its tool There are good thermal stability and higher carrier mobility, passes through Ar1、Ar2、Ar3Between synergistic effect so that compound Cavity transmission ability and stability get a promotion, and realize the equalizing charge in luminescent layer；Further, by carbazole structure Optimize, the pi-pi accumulation between regulatory molecule, makes compound that there is suitable highest occupied molecular orbital energy level and high T1 value, make Luminous auxiliary layer materials'use between hole transmission layer and luminescent layer, can reduce the energy between luminescent layer and anodic interface It is differential, it is more conducive to realizing the equalizing charge in luminescent layer, improves the excitation purity, luminous efficiency and service life of device, And reduce the driving voltage of device.
Organic electroluminescence device of the invention is used as electron transfer layer using compound (II), is mainly used to improve electricity Son reaches the mobility that luminescent layer is surveyed, to improve exciton in the recombination probability of luminescent layer, and then improves the luminous efficiency of device. Compound (II) forms the space structure of 3 D stereo in 1,3,5 introducing fluorenes class groups of strong electron-withdrawing group group triazine, can be with Effective intermolecular accumulation is formed, makes it be not easy to crystallize, is easy to form a film；And triazine and fluorenes class group pass through phenyl ring or cyclohexyl biphenyl Connection, forms extensible big pi-conjugated system, is easy to the flowing of electronics, to improve organic electroluminescence hair of the present invention The electron mobility of optical device electron transfer layer fundamentally improves the threshold value of limit device luminous efficiency.
Organic electroluminescence device of the invention is by by hole transmission layer and/or luminous auxiliary layer, electron transfer layer institute The luminous organic material of use carries out effective adapter combination, while improving electron transfer layer electron transfer rate, to sky Cave transport layer and/or luminous auxiliary layer carry out appropriate adjustment, to realize luminescent layer electrons and holes injection and compound flat Weighing apparatus, avoids migration of the carrier to transport layer side, so as to avoid the dissipation of non-radiative energy, to obtain a kind of driving electricity It forces down, luminous efficiency height, organic electroluminescence device with long service life.
Specific embodiment
It is clearly and completely described below in conjunction with the technical solution of the embodiment of the present invention, it is clear that described implementation Example is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, art technology Personnel's every other embodiment obtained without making creative work, belongs to protection scope of the present invention.
It should be noted that unless otherwise prescribed, the meaning of scientific and technical terminology used in the present invention and those skilled in the art The meaning that member is generally understood is identical.
Aryl of the present invention refers to remove a hydrogen atom on an aromatic core carbon of aromatic hydrocarbon molecule after, remaining group General name, can be monocyclic aryl or fused ring aryl, such as can be selected from phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthrene Base, pyrenyl, fluorenyl or benzo phenanthryl etc., but not limited to this.
Heteroaryl of the present invention refers to the group that one or more aromatic core carbon in aryl are replaced by hetero atom General name, the hetero atom include but is not limited to oxygen, sulphur or nitrogen-atoms, and the heteroaryl can be bicyclic heteroaryl or condensed ring heteroaryl Base, such as pyridyl group, quinolyl, carbazyl, thienyl, benzothienyl, furyl, benzofuranyl, pyrimidine can be selected from Base, benzo pyrimidine radicals, imidazole radicals or benzimidazolyl etc., but not limited to this.
Divalent aryl of the present invention refers to respectively remove a hydrogen atom on two aromatic core carbon of aromatic hydrocarbon molecule after, be left Bivalent group general name, can be valentbivalent monocyclic aryl or divalent fused ring aryl, such as can be selected from phenylene, sub- biphenyl Base, sub- terphenyl, naphthylene, anthrylene, phenanthrylene, sub- pyrenyl, fluorenylidene or sub- benzo phenanthryl etc., but not limited to this.
Divalent heteroaryl radical of the present invention refers to that one or more aromatic core carbon in divalent aryl are replaced to obtain by hetero atom Group general name, the hetero atom includes but is not limited to oxygen, sulphur or nitrogen-atoms, and the divalent heteroaryl radical can be valentbivalent monocyclic Heteroaryl or divalent fused ring heteroaryl, such as can be selected from sub-pyridyl group, sub- quinolyl, sub- carbazyl, sub- thienyl, sub- benzo Thienyl, furylidene, sub- benzofuranyl, sub- pyrimidine radicals, sub- benzo pyrimidine radicals, sub- imidazole radicals or sub- benzimidazolyl etc., But not limited to this.
Alkyl of the present invention refers to alkyl made of minusing one or several hydrogen atoms in alkane molecule, can be straight Alkyl group, branched alkyl, naphthenic base, example may include methyl, ethyl, propyl, isopropyl, normal-butyl, isobutyl group, sec-butyl, Tert-butyl, amyl, isopentyl, cyclopenta, cyclohexyl etc., but not limited to this.
Alkoxy of the present invention refer to alkyl and oxygen atom connection after group, example may include methoxyl group, ethyoxyl, 2- propoxyl group, 2- cyclohexyloxy etc., but not limited to this.
Condensed cyclization of the present invention refers to that two groups are connected to each other by chemical bond.It is as follows:
In the present invention, the ring being fused into can be five-membered ring or hexatomic ring, such as phenyl, naphthalene, hexamethylene and phenyl, quinoline Quinoline base, isoquinolyl, dibenzothiophene, phenanthryl or pyrenyl, but not limited to this.
The present invention provides a kind of organic electroluminescence device, including cathode, anode, it is located at the cathode and the anode Between organic matter layer, the organic matter layer includes hole transmission layer and/or luminous auxiliary layer, electron transfer layer, the sky Contain chemical formula (I) compound represented in cave transport layer and/or luminous auxiliary layer:
Wherein, L1、L2、L3It does not take independently selected from singly-bound, the divalent aryl of substituted or unsubstituted C6~C30, substitution or One of the divalent heteroaryl radical of C3~C30 in generation；Ar1、Ar3It does not take independently selected from substituted or unsubstituted phenyl, substitution or The naphthalene in generation, substituted or unsubstituted anthryl, substituted or unsubstituted fluorenyl, one in two fluorenyl of substituted or unsubstituted spiral shell Kind；Ar2Selected from substituted or unsubstituted carbazyl.
Heretofore described " substituted or unsubstituted ", the substituent group is independent to be selected from D-atom, cyano, nitro, halogen Plain atom, the alkyl of C1-C10, the alkoxy of C1-C10, the alkylthio group of C1-C10, the aryl of C6-C30, C6-C30 fragrant oxygen Base, the arylthio of C6-C30, C3-C30 heteroaryl, the silylation of C1~C30, the alkylamino radical of C2~C10, C6~C30 virtue Amido etc., for example, D-atom, cyano, nitro, halogen, methyl, ethyl, propyl, isopropyl, tert-butyl, methoxyl group, methyl mercapto, Phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, benzo phenanthryl, base, pyrenyl, fluorenyl, 9,9- dimethyl fluorenyl, Benzyl, phenoxy group, thiophenyl, hexichol amido, dimethylamino, carbazyl, 9- phenyl carbazole base, furyl, thienyl, triphen Base silicon substrate, trimethyl silicon substrate, trifluoromethyl, phenothiazinyl, phenoxazine base, acridinyl, piperidyl, pyridyl group, pyrazinyl, triazine Base, pyrimidine radicals etc., but not limited to this.
According to the present invention, the organic matter layer includes hole transmission layer and/or luminous auxiliary layer, electron transfer layer, such as It can be following situation, but not limited to this: 1, organic matter layer include hole transmission layer, electron transfer layer；Or 2, organic matter layer packet Include luminous auxiliary layer, electron transfer layer；Or 3, organic matter layer includes hole transmission layer, shine auxiliary layer, electron transfer layer.
Preferably, the L1、L2、L3Independently selected from singly-bound, substituted or unsubstituted phenyl, substituted or unsubstituted One of naphthalene, substituted or unsubstituted xenyl, it is furthermore preferred that the L1、L2、L3Independently selected from singly-bound, phenyl, One of naphthalene, xenyl.
Preferably, the Ar2It is as follows group:
Wherein, R1Selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 alkoxy, replace or One of unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl；Preferably, the R1Selected from replace or Unsubstituted C1-C4 alkyl, substituted or unsubstituted C6-C18 aryl, one in substituted or unsubstituted C3-C18 heteroaryl Kind；It is furthermore preferred that the R1Selected from methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthalene, xenyl, terphenyl One of base, carbazyl.
R2、R3At each occurrence identical or differently selected from hydrogen atom, D-atom, halogen atom, C1~C10 alkyl, The alkoxy of C1~C10, the aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C3~C30 heteroaryl in It is a kind of；Or the R2、R3The condensed cyclization of both middle arbitrary neighborhoods；Preferably, the R2、R3It is identical or different at each occurrence Ground is selected from hydrogen atom, D-atom, halogen atom, substituted or unsubstituted C1-C4 alkyl, substituted or unsubstituted C6-C18 virtue One of base, substituted or unsubstituted C3-C18 heteroaryl or the R2、R3The condensed cyclization of both middle arbitrary neighborhoods；More preferably , the R2、R3At each occurrence identical or differently selected from hydrogen atom, D-atom, fluorine atom, chlorine atom, methyl, ethyl, One of n-propyl, isopropyl, tert-butyl, phenyl, naphthalene, xenyl, terphenyl, carbazyl or the R2、R3In appoint Meaning adjacent pairs are fused into phenyl ring.
A is selected from 0 to 4 integer, and b is selected from 0 to 3 integer.
Preferably, the Ar2Selected from one of following group:
Preferably, the Ar1、Ar3Independently selected from one of following group:
Wherein, R4、R5、R6、R7It is selected from hydrogen atom, D-atom, halogen atom, C1 identical or differently at each occurrence The alkyl of~C10, the alkoxy of C1~C10, the aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C3~ One of heteroaryl of C30；Or the R4、R5、R6、R7The condensed cyclization of both middle arbitrary neighborhoods；C, d, e, f are independent is selected from 0 To 4 integer.Preferably, the R4、R5、R6、R7It is selected from hydrogen atom, D-atom, halogen identical or differently at each occurrence Atom, substituted or unsubstituted C1-C4 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 are miscellaneous One of aryl or the R4、R5、R6、R7The condensed cyclization of both middle arbitrary neighborhoods；It is furthermore preferred that the R4、R5、R6、R7? It is identical when occurring every time or differently selected from hydrogen atom, D-atom, fluorine atom, chlorine atom, methyl, ethyl, n-propyl, isopropyl One of base, tert-butyl, phenyl, naphthalene, xenyl, terphenyl, carbazyl or the R4、R5、R6、R7Middle arbitrary neighborhood The two is fused into phenyl ring.
Preferably, the Ar1、Ar3Independently selected from one of following group:
As an example, it is not particularly limited, chemical formula (I) compound represented of the present invention is in such as flowering structure Any one:
Preferably, electron transfer layer of the present invention contains chemical formula (II) compound represented:
Wherein, Ar4、Ar5、Ar6Aryl, substituted or unsubstituted C3 independently selected from substituted or unsubstituted C6~C65 One of the heteroaryl of~C65, and Ar4、Ar5、Ar6In at least one be selected from following group:
Wherein, R8、R9Alkyl, substituted or unsubstituted C6~C30 independently selected from substituted or unsubstituted C1~C10 Aryl, one of the heteroaryl of substituted or unsubstituted C6~C30；R10Selected from hydrogen atom, substituted or unsubstituted C1~ One of the alkyl of C10, aryl of substituted or unsubstituted C6~C30.
Preferably, R8、R9Independently selected from methyl, ethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, Substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene Base, substituted or unsubstituted base, substituted or unsubstituted ferrosin base, substituted or unsubstituted pyridyl group, substitution do not take The pyrimidine radicals in generation, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazine radical, takes substituted or unsubstituted pyrazinyl It is generation or unsubstituted pyrrole radicals, substituted or unsubstituted benzopyrrole base, substituted or unsubstituted triazolyl, substituted or unsubstituted Thienyl, substituted or unsubstituted furyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuran Base, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted quinoline One of base, substituted or unsubstituted isoquinolyl, substituted or unsubstituted indyl；R10Selected from hydrogen atom, methyl, second Base, isopropyl or tert-butyl.
Preferably, Ar4、Ar5、Ar6At least one is selected from following group:
Wherein, R8、R9Independently selected from methyl, ethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, take Generation or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene Base, substituted or unsubstituted base, substituted or unsubstituted ferrosin base, substituted or unsubstituted pyridyl group, substitution do not take The pyrimidine radicals in generation, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazine radical, takes substituted or unsubstituted pyrazinyl It is generation or unsubstituted pyrrole radicals, substituted or unsubstituted benzopyrrole base, substituted or unsubstituted triazolyl, substituted or unsubstituted Thienyl, substituted or unsubstituted furyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuran Base, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted quinoline One of base, substituted or unsubstituted isoquinolyl, substituted or unsubstituted indyl；R10Selected from hydrogen atom, methyl, second Base, isopropyl or tert-butyl.
Preferably, Ar5、Ar6It is identical, it is selected from following group:
Wherein, R8、R9Independently selected from methyl, ethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, take Generation or unsubstituted anthryl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted pyrazine One of base；R10Selected from hydrogen atom, methyl, ethyl, isopropyl or tert-butyl.
Preferably, Ar4Selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene Base, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted acridinyl, substitution do not take Phenoxazine base, substituted or unsubstituted phenothiazinyl, the substituted or unsubstituted phenoxazine thiophene base, substituted or unsubstituted fluorenes in generation Base, substituted or unsubstituted pyrenyl, substituted or unsubstituted ferrosin base, replaces or does not take substituted or unsubstituted carbazyl The base in generation, substituted or unsubstituted acenaphthenyl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substitution or Unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazine radical, substituted or unsubstituted pyrroles Base, substituted or unsubstituted benzopyrrole base, substituted or unsubstituted triazolyl, substituted or unsubstituted thienyl, substitution or It is unsubstituted furyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted Dibenzothiophene, one of substituted or unsubstituted dibenzofuran group.
As an example, it is not particularly limited, the electron transfer layer of organic electroluminescence device of the present invention is selected from such as Any one in flowering structure:
Be enumerated above hole transmission layer of the present invention and/or luminous auxiliary layer, electron transfer layer it is some specific Compound structure, but the invention is not limited to these listed compound structures, it is all with listed chemical formula (I), chemical formula (II) based on shown in, substituent group is that group as defined above should be all included.
Hole transmission layer of the present invention and/or luminous auxiliary layer compound (I) can pass through conventional coupling reaction system It is standby to obtain, such as can be prepared by following synthetic route, however, the present invention is not limited thereto:
Contain Ar3Aromatic amine compound (A) first with contain Ar1Bromide (B) occur Buchwald reaction, obtain Intermediate M；Intermediate M again with contain Ar2Bromide (C) occur Buchwald reaction, finally obtain target compound (I).
Wherein, Ar1、Ar2、Ar3And L1、L2、L3Restriction as described above, details are not described herein.
Electron transfer layer compound (II) of the present invention is obtained by following synthetic route:
Wherein Ar4、Ar5、Ar6Restriction as described above, details are not described herein.
Raw material e, Ar4-B(OH)2, by Suzuki coupling reaction, using tetra-triphenylphosphine palladium as catalyst, potassium carbonate is alkali, Tetrahydrofuran is solvent, and reflux is reacted to obtain intermediate f；Intermediate f, Ar5-B(OH)2, by Suzuki coupling reaction, Using tetra-triphenylphosphine palladium as catalyst, potassium carbonate is alkali, and tetrahydrofuran is solvent, and reflux is reacted to obtain intermediate g；It is intermediate Body g, Ar6-B(OH)2, by Suzuki coupling reaction, using tetra-triphenylphosphine palladium as catalyst, potassium carbonate is alkali, and tetrahydrofuran is Solvent, reflux are reacted to obtain compound ii.
The present invention does not have special limitation to the above-mentioned reaction condition respectively reacted, and use is well-known to those skilled in the art Reaction condition, the preparation method is simple, and raw material is easy to get.
Organic electroluminescence device of the invention includes cathode, anode, the organic matter between the cathode and anode Layer, organic matter layer of the present invention include hole transmission layer and/or luminous auxiliary layer, electron transfer layer, wherein hole transport Layer and luminous auxiliary layer can individualism, can also exist simultaneously, for example, can be following situation, but not limited to this: 1, organic matter Layer includes hole transmission layer, electron transfer layer；Or 2, organic matter layer includes shine auxiliary layer, electron transfer layer；Or 3, organic matter Layer includes hole transmission layer, shine auxiliary layer, electron transfer layer.
Contain compound (I) in its hole-transporting layer and/or luminous auxiliary layer, electron transfer layer contains compound (Ⅱ)。
In addition, organic matter layer may also include hole injection layer, electronic barrier layer, luminescent layer, hole blocking layer, electron injection At least one layer in layer etc..Luminescent layer can be light emitting host doping light-emitting guest form, be also possible to single substance as hair Photosphere.
Wherein the luminous auxiliary layer is between hole transmission layer and luminescent layer, have good cavity transmission ability and Electron-blocking capability is used for equilbrium carrier, improves the recombination probability in hole and electronics in luminescent layer, avoids electronics to anode-side Transmission, to improve the service life of organic luminescent device.
Preferably, anode uses ITO.
Preferably, hole injection layer is selected from 2-TNATA, CuPc, m-MTDATA, DNTPD etc., can be single substance structure At single structure, can also be different material formation single layer structure or multilayered structure.
Preferably, hole transmission layer is selected from chemical compounds I of the present invention, NPB, TDATA, TPD, TAPC, Spiro-TAD Deng, can be single substance composition single structure, can also be different material formation single layer structure or multilayered structure.
Preferably, the auxiliary layer that shines is selected from compound of the present invention (I), NPB, TDATA, TPD, TAPC, Spiro- TAD etc., and it is different from hole transmission layer, it can be the single structure of single substance composition, can also be different material formation Single layer structure or multilayered structure.
Preferably, electronic barrier layer can be selected from NPB, TDATA, TPD, TAPC, Spiro-TAD etc..
Preferably, shine layer main body be selected from ADN, CPB, mCP, TCTA, 3Ph-anthracene, α-ADN, 4P-NPB, DPVBI、TCP、TCTA、Alq3Deng, can be single substance composition single structure, can also be different material formation single layer Structure or multilayered structure.
Preferably, luminescent layer object is selected from TPD, DPAP-DPPA, TPPDA, Ir (ppy)3、Ir(ppy)2(acac)、Ir (piq)3、 Ir(piq)2(acac)、FIrPic、DCJTB、DCJT、DCM、DCM2、DMQA、DBQA、TMDBQA、HAT-CN、 F4- TCNQ etc..
Preferably, hole blocking layer is selected from BCP, TPBi, Alq3, Liq, BAlq, TAZ and NTAZ etc..
Preferably, electron transfer layer is selected from compound of the present invention (II).
Preferably, electron injecting layer can be selected from LiF.
Preferably, cathode is selected from Al.
Its structure of a kind of organic electroluminescence device of the present invention is preferred are as follows:
1, substrate/ITO/ hole injection layer/hole transmission layer (chemical compounds I)/luminescent layer/electron transfer layer (compound II)/electron injecting layer/Al；
2, substrate/ITO/ hole injection layer/hole transmission layer/luminous auxiliary layer (chemical compounds I)/luminescent layer/electron-transport Layer (compound ii)/electron injecting layer/Al.
3, substrate/ITO/ hole injection layer/hole transmission layer (chemical compounds I)/shine auxiliary layer (chemical compounds I)/luminescent layer/ Electron transfer layer (compound ii)/electron injecting layer/Al；
4, substrate/ITO/ hole injection layer/hole transmission layer (chemical compounds I)/luminous auxiliary layer/luminescent layer/electron-transport Layer (compound ii)/electron injecting layer/Al.
However, the structure of organic electroluminescence device is not limited to this.Organic electroluminescence device of the present invention can It is selected and is combined according to the characteristic of device parameter requirements and material, part organic layer can also be added or omitted.
Organic electroluminescence device of the present invention can be used for flat-panel monitor, lighting source, direction board, signal lamp etc. and answer Use field.
By following embodiment, the present invention, but so as not to the limitation present invention are more fully explained.In the base of the description On plinth, those of ordinary skill in the art will without creative efforts, in disclosed entire scope Implement the present invention and prepares other compounds and device according to the present invention.
The present invention is not particularly limited raw material sources employed in following embodiment, for commercial product or can adopt It is prepared with preparation method well-known to those skilled in the art.
The synthesis of 1 compound HT2-1 of embodiment
Under argon atmospher, by bromide B-1 (5.93g, 15mmol), amine compounds A-1 (3.14g, 15mmol), sodium tert-butoxide (2.88g, 30mmol) is added in 150ml dehydrated toluene, stirs lower addition palladium acetate (0.07g, 0.3mmol), tri-tert Phosphine (0.06g, 0.3mmol) reacts 8 hours at 80 DEG C.After cooling, it is filtered by diatomite/silica gel funnel, filtrate passes through Vacuum distillation removal organic solvent, residue obtained to recrystallize in toluene, leaching obtained solid is dry, obtains intermediate M-1.
Under argon atmospher, to intermediate M-1 (5.24g, 10mmol), bromide C-1 (4.87g, 10mmol), three (two benzal Benzylacetone) two palladiums (0.14g, 0.15mmol), tri-tert-butylphosphine tetrafluoroborate (0.087g, 0.3mmol), sodium tert-butoxide 50ml anhydrous dimethyl benzene is added in (1.9g, 20mmol), is flowed back 8 hours.50 DEG C are cooled to, is filtered by diatomite/silica gel, filter Liquid concentration, residue obtained to be purified with silica gel column chromatography, gained crude product recrystallizes in toluene, obtains compound HT2-1 (6.13g, 6.6mmol), yield 66%.Mass spectrum m/z:929.50 (calculated value: 929.38).Theoretical elemental content (%) C70H47N3: C, 90.39；H,5.09；N,4.52.Survey constituent content (%): C, 90.47；H,5.04；N,4.53.The above results Confirm that obtaining product is target product.
Embodiment 2: the preparation of compound HT2-4
Bromide B-1 is replaced with to the bromide B-4 of equimolar amounts, other steps are same as Example 1, can obtain To compound HT2-4.Mass spectrum m/z:1041.38 (calculated value: 1041.50).Theoretical elemental content (%) C78H63N3: C, 89.88； H,6.09；N,4.03.Survey constituent content (%): C, 89.80；H,6.06；N,4.03.The above results confirm that obtaining product is mesh Mark product.
Embodiment 3: the preparation of compound HT2-5
Bromide B-1 is replaced with to the bromide B-5 of equimolar amounts, other steps are same as Example 1, can obtain To compound HT2-5.Mass spectrum m/z:1005.29 (calculated value: 1005.41).Theoretical elemental content (%) C76H51N3: C, 90.72； H,5.11；N,4.18.Survey constituent content (%): C, 90.85；H,5.10；N,4.17.The above results confirm that obtaining product is mesh Mark product.
Embodiment 4: the preparation of compound HT2-10
Bromide B-1 is replaced with to the bromide B-10 of equimolar amounts, other steps are same as Example 1 Obtain compound HT2-10.Mass spectrum m/z:979.28 (calculated value: 979.39).Theoretical elemental content (%) C74H49N3: C, 90.67； H,5.04；N,4.29.Survey constituent content (%): C, 90.74；H,5.02；N,4.27.The above results confirm to obtain Product is target product.
Embodiment 5: the preparation of compound HT2-13
Bromide B-1 is replaced with to the bromide B-13 of equimolar amounts, other steps are same as Example 1 Obtain compound HT2-13.Mass spectrum m/z:979.29 (calculated value: 979.39).Theoretical elemental content (%) C74H49N3: C, 90.67； H,5.04；N,4.29.Survey constituent content (%): C, 90.73；H,5.02；N,4.26.The above results confirm to obtain Product is target product.
Embodiment 6: the preparation of compound HT2-14
Aminate A-1 is replaced with to the bromide A-14 of equimolar amounts, other steps are same as Example 1 Obtain compound HT2-14.Mass spectrum m/z:979.27 (calculated value: 979.39).Theoretical elemental content (%) C74H49N3: C, 90.67； H,5.04；N,4.29.Survey constituent content (%): C, 90.72；H,5.04；N,4.28.The above results confirm to obtain Product is target product.
Embodiment 7: the preparation of compound HT2-21
Bromide B-1 is replaced with to the bromide B-4 of equimolar amounts, bromide C-1 is replaced with the bromine of equimolar amounts Compound C-21, other steps are same as Example 1, and compound HT2-21 can be obtained.Mass spectrum m/z:1041.62 (is calculated Value: 1041.50).Theoretical elemental content (%) C78H63N3: C, 89.88；H,6.09；N,4.03.Constituent content (%): C is surveyed, 89.93； H,6.09；N,4.03.The above results confirm that obtaining product is target product.
Embodiment 8: the preparation of compound HT2-25
Bromide B-1 is replaced with to the bromide B-4 of equimolar amounts, bromide C-1 is replaced with the bromine of equimolar amounts Compound C-25, other steps are same as Example 1, and compound HT2-25 can be obtained.Mass spectrum m/z:1041.39 (is calculated Value: 1041.50).Theoretical elemental content (%) C78H63N3: C, 89.88；H,6.09；N,4.03.Constituent content (%): C is surveyed, 89.78； H,6.07；N,4.02.The above results confirm that obtaining product is target product.
Embodiment 9: the preparation of compound HT2-26
Bromide C-1 is replaced with to the bromide C-26 of equimolar amounts, other steps are same as Example 1 Obtain compound HT2-26.Mass spectrum m/z:880.27 (calculated value: 880.38).Theoretical elemental content (%) C67H48N2: C, 91.33；H,5.49；N,3.18.Survey constituent content (%): C, 91.28；H,5.46；N,3.17.The above results confirmation is produced Object is target product.
Embodiment 10: the preparation of compound HT2-29
Bromide B-1 is replaced with to the bromide B-4 of equimolar amounts, bromide C-1 is replaced with the bromine of equimolar amounts Compound C-26, other steps are same as Example 1, and compound HT2-29 can be obtained.Mass spectrum m/z:992.46 (calculated value: 992.51).Theoretical elemental content (%) C75H64N2: C, 90.69；H,6.49；N,2.82.Constituent content (%): C is surveyed, 90.61； H,6.45；N,2.84.The above results confirm that obtaining product is target product.
Embodiment 11: the preparation of compound HT2-30
Bromide B-1 is replaced with to the bromide B-5 of equimolar amounts, bromide C-1 is replaced with the bromine of equimolar amounts Compound C-26, other steps are same as Example 1, and compound HT2-30 can be obtained.Mass spectrum m/z:956.54 (calculated value: 956.41).Theoretical elemental content (%) C73H52N2: C, 91.60；H,5.48；N,2.93.Constituent content (%): C is surveyed, 91.70； H,5.48；N,2.94.The above results confirm that obtaining product is target product.
Embodiment 12: the preparation of compound HT2-35
Bromide B-1 is replaced with to the bromide B-10 of equimolar amounts, bromide C-1 is replaced with the bromine of equimolar amounts Compound C-26, other steps are same as Example 1, and compound HT2-35 can be obtained.Mass spectrum m/z:930.34 (calculated value: 930.40).Theoretical elemental content (%) C71H50N2: C, 91.58；H,5.41；N,3.01.Constituent content (%): C is surveyed, 91.49； H,5.40；N,3.02.The above results confirm that obtaining product is target product.
Embodiment 13: the preparation of compound HT2-38
Bromide B-1 is replaced with to the bromide B-13 of equimolar amounts, bromide C-1 is replaced with the bromine of equimolar amounts Compound C-26, other steps are same as Example 1, and compound HT2-38 can be obtained.Mass spectrum m/z:930.32 (calculated value: 930.40).Theoretical elemental content (%) C71H50N2: C, 91.58；H,5.41；N,3.01.Constituent content (%): C is surveyed, 91.52； H,5.40；N,3.02.The above results confirm that obtaining product is target product.
Embodiment 14: the preparation of compound HT2-49
Bromide B-1 is replaced with to the bromide B-4 of equimolar amounts, bromide C-1 is replaced with the bromine of equimolar amounts Compound C-49, other steps are same as Example 1, and compound HT2-49 can be obtained.Mass spectrum m/z:992.47 (calculated value: 992.51).Theoretical elemental content (%) C75H64N2: C, 90.69；H,6.49；N,2.82.Constituent content (%): C is surveyed, 90.71； H,6.47；N,2.81.The above results confirm that obtaining product is target product.
Embodiment 15: the preparation of compound HT2-51
Bromide C-1 is replaced with to the bromide C-51 of equimolar amounts, other steps are same as Example 1 Obtain compound HT2-51.Mass spectrum m/z:764.44 (calculated value: 764.32).Theoretical elemental content (%) C58H40N2: C, 91.07； H,5.27；N,3.66.Survey constituent content (%): C, 91.11；H,5.27；N,3.65.The above results confirm to obtain Product is target product.
Embodiment 16: the preparation of compound HT2-54
Bromide B-1 is replaced with to the bromide B-4 of equimolar amounts, bromide C-1 is replaced with the bromine of equimolar amounts Compound C-54, other steps are same as Example 1, and compound HT2-54 can be obtained.Mass spectrum m/z:926.37 (calculated value: 926.46).Theoretical elemental content (%) C70H58N2: C, 90.67；H,6.31；N,3.02.Constituent content (%): C is surveyed, 90.61； H,6.29；N,3.02.The above results confirm that obtaining product is target product.
Embodiment 17: the preparation of compound HT2-55
Bromide B-1 is replaced with to the bromide B-5 of equimolar amounts, bromide C-1 is replaced with the bromine of equimolar amounts Compound C-54, other steps are same as Example 1, and compound HT2-55 can be obtained.Mass spectrum m/z:890.29 (calculated value: 890.37).Theoretical elemental content (%) C68H46N2: C, 91.65；H,5.20；N,3.14.Constituent content (%): C is surveyed, 91.60； H,5.19；N,3.12.The above results confirm that obtaining product is target product.
Embodiment 18: the preparation of compound HT2-76
Bromine bromide C-1 is replaced with to the bromide C-76 of equimolar amounts, other steps are same as Example 1, i.e., Compound HT2-76 can be obtained.Mass spectrum m/z:870.25 (calculated value: 870.31).Theoretical elemental content (%) C64H42N2S:C, 88.24；H,4.86；N,3.22；S,3.68.Survey constituent content (%): C, 88.20；H,4.89；N,3.22；S,3.68.It is above-mentioned As a result confirm that obtaining product is target product.
Embodiment 19: the preparation of compound HT2-80
Bromide B-1 is replaced with to the bromide B-5 of equimolar amounts, bromide C-1 is replaced with the bromine of equimolar amounts Compound C-76, other steps are same as Example 1, and compound HT2-80 can be obtained.Mass spectrum m/z:964.25 (calculated value: 964.34).Theoretical elemental content (%) C70H46N2S:C, 88.76；H,4.90；N,2.96；S,3.38.Survey constituent content (%): C, 88.70；H,4.89；N,2.96；S,3.38.The above results confirm that obtaining product is target product.
Embodiment 20: the preparation of compound HT2-101
Bromide C-1 is replaced with to the bromide C-101 of equimolar amounts, other steps are same as Example 1 Obtain compound HT2-101.Mass spectrum m/z:854.23 (calculated value: 854.33).Theoretical elemental content (%) C64H42N2O:C, 89.90；H,4.95；N,3.28；O,1.87.Survey constituent content (%): C, 89.85；H,4.94；N,3.26；O,1.88.It is above-mentioned As a result confirm that obtaining product is target product.
Embodiment 21: the preparation of compound HT2-105
Bromide B-1 is replaced with to the bromide B-5 of equimolar amounts, bromide C-1 is replaced with the bromine of equimolar amounts Compound C-101, other steps are same as Example 1, and compound HT2-105 can be obtained.Mass spectrum m/z:930.25 (is calculated Value: 930.36).Theoretical elemental content (%) C70H46N2O:C, 90.29；H,4.98；N,3.01；O,1.72.Survey constituent content (%): C, 90.26；H,4.94；N,3.02；O,1.72.The above results confirm that obtaining product is target product.
Embodiment 22: the preparation of compound HT2-126
Change aminate A-1 into aminate A-126 for equimolar amounts, other steps are same as Example 1, can obtain To compound HT2-126.Mass spectrum m/z:929.50 (calculated value: 929.38).Theoretical elemental content (%) C70H47N3: C, 90.39； H,5.09；N,4.52.Survey constituent content (%): C, 90.47；H,5.04；N,4.53.The above results confirm that obtaining product is mesh Mark product.
Embodiment 23: the preparation of compound HT2-130
Bromide B-1 is replaced with to the bromide B-130 of equimolar amounts, other steps are same as Example 1 Obtain compound HT2-130.Mass spectrum m/z:1013.35 (calculated value: 1013.47).Theoretical elemental content (%) C76H59N3: C, 89.99；H,5.86；N,4.14.Survey constituent content (%): C, 89.89；H,5.84；N,4.12.The above results confirmation is produced Object is target product.
Embodiment 24: the preparation of compound HT2-145
Change aminate A-1 into aminate A-126 for equimolar amounts, bromide C-1 is replaced with the bromine of equimolar amounts Compound C-26, other steps are same as Example 1, and compound HT2-145 can be obtained.Mass spectrum m/z:880.49 (is calculated Value: 880.38).Theoretical elemental content (%) C67H48N2: C, 91.33；H,5.49；N,3.18.Constituent content (%): C is surveyed, 91.37；H,5.49；N,3.18.The above results confirm that obtaining product is target product.
Embodiment 25: the preparation of compound HT2-163
Bromide C-1 is replaced with to the bromide C-54 of equimolar amounts, other steps are same as Example 1 Obtain compound HT2-163.Mass spectrum m/z:814.29 (calculated value: 814.33).Theoretical elemental content (%) C62H42N2: C, 91.37； H,5.19；N,3.44.Survey constituent content (%): C, 91.30；H,5.19；N,3.43.The above results confirm to obtain Product is target product.
Embodiment 26: the preparation of compound HT2-167
Bromide C-1 is replaced with to the bromide C-167 of equimolar amounts, other steps are same as Example 1 Obtain compound HT2-167.Mass spectrum m/z:764.28 (calculated value: 764.32).Theoretical elemental content (%) C58H40N2: C, 91.07；H,5.27；N,3.66.Survey constituent content (%): C, 91.00；H,5.29；N,3.66.The above results confirmation is produced Object is target product.
Embodiment 27: the preparation of compound HT2-194
Aminate A-194 is replaced with to the aminate A-1 of equimolar amounts, other steps are same as Example 1 Obtain compound HT2-194.Mass spectrum m/z:813.26 (calculated value: 813.31).Theoretical elemental content (%) C61H39N3: C, 90.01；H,4.83；N,5.16.Survey constituent content (%): C, 89.98；H,4.82；N,5.16.The above results confirmation is produced Object is target product.
Embodiment 28: the preparation of compound HT2-203
Bromide B-203 is replaced with to the bromide B-1 of equimolar amounts, other steps are same as Example 1 Obtain compound HT2-203.Mass spectrum m/z:691.20 (calculated value: 691.30).Theoretical elemental content (%) C51H37N3: C, 88.54；H,5.39；N,6.07.Survey constituent content (%): C, 88.50；H,5.39；N,6.06.The above results confirmation is produced Object is target product.
The synthesis of 29 compound ET1 of embodiment
Step1: taking 3,5- dichlorobenzene (9.4g, 42.4mmol) to be added in there-necked flask, and THF 100mL, nitrogen is added Protection, -78 DEG C are stirred 30 minutes, and n-BuLi (2.5M) 21mL is then added, reacts 1 hour, adds triisopropyl borate ester 14g low-temp reaction 1 hour, is gradually recovered room temperature.Last handling process, 2M hydrochloric acid is added in system makes solution pH value 4-5, quiet Liquid separation is set, aqueous layer with ethyl acetate extraction merges organic layer, is spin-dried for, obtains intermediate E T1-1 (8.2g, 80%).
Step2: tetra-triphenylphosphine palladium (2.1g, 1.83mmol) and potassium carbonate (75.7g, 549mmol) are added to centre Bromo- 9, the 9- dimethyl fluorene (50.3g, 185mmol) of body ET1-1 (44.3g, 183mmol) and 2- is in degassing tetrahydrofuran Solution in (500mL), and the mixture is heated 4 hours under reflux.It filters while hot, obtains a large amount of solids, use solvent Dissolved solid is concentrated later, obtains intermediate E T1-2 (50.0g, 70%) via silica gel column chromatography.
Step3: tetra-triphenylphosphine palladium (2.1g, 1.83mmol) and potassium carbonate (75.7g, 549mmol) are added to centre The bromo- 6- phenyl -1,3,5-triazines (41.3g, 183mmol) of body ET1-2 (150g, 384mmol) and 2,4- bis- is in degassing tetrahydro furan The solution muttered in (500mL), and the mixture is heated 4 hours under reflux.It filters while hot, obtains a large amount of solids, use is molten Agent dissolved solid, is concentrated later, obtains compound ET1 (92.9g, 60%) via silica gel column chromatography.Mass spectrum m/z:845.31 (calculated value: 845.38).Theoretical elemental content (%) C63H47N3: C, 89.43；H,5.60；N,4.97.Survey constituent content (%): C, 89.40；H,5.59；N,4.96.The above results confirm that obtaining product is target product.
The synthesis of 30 compound ET41 of embodiment
It after penta phenanthrene of Step1:4H- ring is replaced by iodomethane, is reacted with bromine, it is luxuriant and rich with fragrance to obtain bromo- 4, the 4- diformazan basic ring penta of 8-.It takes Bromo- 4, the 4- diformazan basic ring penta luxuriant and rich with fragrance (12.6g, 42.4mmol) of 8- is added in there-necked flask, addition THF 100mL, nitrogen protection ,- 78 DEG C are stirred 30 minutes, and n-BuLi (2.5M) 21mL is then added, reacts 1 hour, adds triisopropyl borate ester 7g, low temperature Reaction 1 hour, is gradually recovered room temperature.Last handling process, 2M hydrochloric acid is added in system makes solution pH value 4-5, standing liquid separation, water Layer is extracted with ethyl acetate, and merges organic layer, is spin-dried for, obtains intermediate E T41-1 (8.3g, 75%).
Step2: tetra-triphenylphosphine palladium (2.1g, 1.83mmol) and potassium carbonate (75.7g, 549mmol) are added to centre The bromo- 6- phenyl -1,3,5-triazines (41.3g, 183mmol) of body ET41-1 (100.6g, 384mmol) and 2,4- bis- is in degassing four Solution in hydrogen furans (500mL), and the mixture is heated 4 hours under reflux.It filters while hot, obtains a large amount of solids, It with solvent dissolved solid, is concentrated later, obtains compound ET41 (70.0g, 65%) via silica gel column chromatography.Mass spectrum m/z: 589.20 (calculated values: 589.25).Theoretical elemental content (%) C43H31N3: C, 87.58；H,5.30；N,7.13.Actual measurement element contains Measure (%): C, 87.51；H,5.30；N,7.10.The above results confirm that obtaining product is target product.
The synthesis of 31 compound ET63 of embodiment
After penta phenanthrene of Step1:4H- ring is restored by Pd/C, react to obtain bromo compound with bromine, then oxidative cyclization obtains The bromo- 4H- ring penta of 2- is luxuriant and rich with fragrance, and iodomethane reacts with it to obtain bromo- 4,4- diformazan basic ring, penta phenanthrene of 2-.Take the bromo- 4,4- diformazan basic ring penta of 2- Luxuriant and rich with fragrance (12.6g, 42.4mmol) is added in there-necked flask, is added THF 100mL, nitrogen protection, and -78 DEG C are stirred 30 minutes, then N-BuLi (2.5M) 21mL is added, reacts 1 hour, adds triisopropyl borate ester 7g, low-temp reaction 1 hour, be gradually recovered Room temperature.Last handling process, 2M hydrochloric acid is added in system makes solution pH value 4-5, stands liquid separation, and aqueous layer with ethyl acetate extracts, Merge organic layer, is spin-dried for, obtains intermediate E T63-1 (8.3g, 75%).
Step2: tetra-triphenylphosphine palladium (2.1g, 1.83mmol) and potassium carbonate (75.7g, 549mmol) are added to centre Body ET63-1 (100.6g, 384mmol) and compound d (57.6g, 183mmol) is molten in degassing tetrahydrofuran (500mL) Liquid, and the mixture is heated 4 hours under reflux.It filters while hot, obtains a large amount of solids, with solvent dissolved solid, later Concentration, obtains compound ET63 (74.5g, 60%) via silica gel column chromatography.Mass spectrum m/z:679.19 (calculated value: 679.26). Theoretical elemental content (%) C49H33N3O:C, 86.57；H,4.89；N,6.18；O,2.35.Constituent content (%): C is surveyed, 86.50；H,4.89；N,6.16；O,2.35.The above results confirm that obtaining product is target product.
The synthesis of 32 compound ET77 of embodiment
Step1: taking bromo- 9,9- spiral shell, two fluorenes (16.7g, 42.4mmol) of 2- to be added in there-necked flask, and THF 100mL is added, Nitrogen protection, -78 DEG C are stirred 30 minutes, and n-BuLi (2.5M) 21mL is then added, reacts 1 hour, it is different to add boric acid three Propyl ester 7g low-temp reaction 1 hour, is gradually recovered room temperature.Last handling process, 2M hydrochloric acid is added in system makes solution pH value 4- 5, stand liquid separation, aqueous layer with ethyl acetate extraction, merge organic layer, be spin-dried for, obtain two fluorenes of 2- boric acid -9,9- spiral shell (12.2g, 80%).
Step2: tetra-triphenylphosphine palladium (2.1g, 1.83mmol) and potassium carbonate (75.7g, 549mmol) are added to 2- boron Two fluorenes (65.8g, 183mmol) of acid -9,9- spiral shell and the chloro- 4- of 2- (biphenyl -4- base) -6- phenyl -1,3,5-triazines (63.6g, 185mmol) the solution in degassing tetrahydrofuran (500mL), and the mixture is heated 4 hours under reflux.It takes out while hot Filter, obtain a large amount of solids, with solvent dissolved solid, be concentrated later, via silica gel column chromatography obtain compound ET77 (71.8g, 60%).Mass spectrum m/z:623.18 (calculated value: 623.24).Theoretical elemental content (%) C46H29N3: C, 88.58；H,4.69；N, 6.74.Survey constituent content (%): C, 88.55；H,4.69；N,6.76.The above results confirm that obtaining product is target product.
Comparative device embodiment:
Ito glass substrate is placed in distilled water and is cleaned 2 times, it is ultrasonic washing 30 minutes, different after distilled water cleans Ultrasonic washing is later dry in order for propyl alcohol, acetone, methanol equal solvent, is transferred in plasma washing machine, by above-mentioned base Plate washs 5 minutes, is sent in evaporator.
On the ito transparent electrode having had been prepared for successively: hole injection layer 2-TNATA/60nm, hole transmission layer chemical combination Object NPB/30nm, vapor deposition main body A DN: doping 2% mixing of BDAVBi/30nm, electron transfer layer Alq3/ 30nm, electron injection Layer LiF/1nm, cathode Al/300nm.
Device embodiments 1-8:
It is as shown in Table 1 below by the hole transmission layer in comparative device embodiment, the substitution of materials in electron transfer layer.
Device embodiments 9-16
Ito glass substrate is placed in distilled water and is cleaned 2 times, it is ultrasonic washing 30 minutes, different after distilled water cleans Ultrasonic washing is later dry in order for propyl alcohol, acetone, methanol equal solvent, is transferred in plasma washing machine, by above-mentioned base Plate washs 5 minutes, is sent in evaporator.
On the ito transparent electrode having had been prepared for successively: hole injection layer 2-TNATA/60nm, hole transmission layer chemical combination Object NPB/30nm, the auxiliary layer compound/20nm that shines, vapor deposition main body A DN: doping 2% mixing of BDAVBi/30nm, electronics pass Defeated layer compound/30nm, electron injecting layer LiF/1nm, cathode Al/300nm.
Device embodiments 17-24
Ito glass substrate is placed in distilled water and is cleaned 2 times, it is ultrasonic washing 30 minutes, different after distilled water cleans Ultrasonic washing is later dry in order for propyl alcohol, acetone, methanol equal solvent, is transferred in plasma washing machine, by above-mentioned base Plate washs 5 minutes, is sent in evaporator.
Hole injection layer 2-TNATA/60nm, hole transmission layer are successively deposited on the ito transparent electrode having had been prepared for / 30nm, the auxiliary layer compound/20nm that shines, vapor deposition main body A DN: doping 2% mixing of BDAVBi/30nm, electron transfer layer/ 30nm, electron injecting layer LiF/1nm, cathode Al/300nm.
Comparative device embodiment of the present invention and the characteristics of luminescence of the luminescent device of device embodiments 1-24 preparation test knot Fruit is as shown in table 1.
[table 1]
The above result shows that organic electroluminescence device provided by the invention, by combining chemical formula of the present invention (I), (II) compound represented, design with different hole transmission layers, shine auxiliary layer, electron transfer layer it is organic Electroluminescent device, corresponding hole transmission layer and/or luminous auxiliary layer, electron transfer layer collective effect under, carrier Injection is transmitted and is effectively improved in the compound of luminescent layer, and the luminous efficiency of organic electroluminescence device of the invention is able to It effectively improves, and in luminescent layer carrier injection balance, so as to avoid in the energy accumulation of electron transfer layer side and non-spoke Energy dissipation is penetrated, so that the service life of device is effectively improved.Organic electroluminescence device tool provided by the invention Have starting voltage it is low, luminous efficiency is high, it is with long service life a little, and its provide the change for preparing the organic electroluminescence device It closes the raw material that object uses to be easy to get, synthetic method is simple, easy to operate, the demand for meeting industry and market of high degree.
Obviously, the above description of the embodiment is only used to help understand the method for the present invention and its core ideas.It should refer to It out, without departing from the principle of the present invention, can also be to this hair for the those of ordinary skill of the technical field Bright some improvement and modification can also be carried out, and these improvements and modifications also fall within the scope of protection of the claims of the present invention.

Claims (10)

1. a kind of organic electroluminescence device, including cathode, anode, the organic matter between the cathode and the anode Layer, the organic matter layer includes hole transmission layer and/or luminous auxiliary layer, electron transfer layer, which is characterized in that the hole Contain chemical formula (I) compound represented in transport layer and/or luminous auxiliary layer:
Wherein, L1、L2、L3Divalent aryl, substituted or unsubstituted independently selected from singly-bound, substituted or unsubstituted C6~C30 One of divalent heteroaryl radical of C3~C30；Ar1、Ar3Independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted One of naphthalene, substituted or unsubstituted anthryl, substituted or unsubstituted fluorenyl, two fluorenyl of substituted or unsubstituted spiral shell；Ar2 Selected from substituted or unsubstituted carbazyl.
2. a kind of organic electroluminescence device according to claim 1, which is characterized in that the L1、L2、L3Independently Selected from one of singly-bound, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted xenyl.
3. a kind of organic electroluminescence device according to claim 1, which is characterized in that the Ar2It is as follows base Group:
Wherein, R1Selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 alkoxy, replaces or do not take One of the C6-C30 aryl in generation, substituted or unsubstituted C3-C30 heteroaryl；
R2、R3At each occurrence identical or differently selected from hydrogen atom, D-atom, halogen atom, the alkyl of C1~C10, C1~ The alkoxy of C10, the aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C3~C30 heteroaryl in one Kind；Or the R2、R3The condensed cyclization of both middle arbitrary neighborhoods；
A is selected from 0 to 4 integer, and b is selected from 0 to 3 integer.
4. a kind of organic electroluminescence device according to claim 1, which is characterized in that the Ar2Selected from following group One of:
5. a kind of organic electroluminescence device according to claim 1, which is characterized in that Ar1、Ar3Independently selected from following One of group:
Wherein, R4、R5、R6、R7It is selected from hydrogen atom, D-atom, halogen atom, C1~C10 identical or differently at each occurrence Alkyl, the alkoxy of C1~C10, the aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C3~C30 it is miscellaneous One of aryl；Or the R4、R5、R6、R7The condensed cyclization of both middle arbitrary neighborhoods；C, d, e, f it is independent be selected from 0 to 4 it is whole Number.
6. a kind of organic electroluminescence device according to claim 1, which is characterized in that Ar1、Ar3Independently selected from following One of group:
7. a kind of organic electroluminescence device according to claim 1-6, which is characterized in that the electron-transport Layer contains chemical formula (II) compound represented:
Wherein, Ar4、Ar5、Ar6Aryl, substituted or unsubstituted C3 independently selected from substituted or unsubstituted C6~C65~ One of heteroaryl of C65, and Ar4、Ar5、Ar6In at least one be selected from following group:
Wherein, R8、R9The virtue of alkyl, substituted or unsubstituted C6~C30 independently selected from substituted or unsubstituted C1~C10 One of base, heteroaryl of substituted or unsubstituted C6~C30；R10Selected from hydrogen atom, substituted or unsubstituted C1~C10 One of alkyl, aryl of substituted or unsubstituted C6~C30.
8. according to a kind of described in any item organic electroluminescence devices of claim 7, which is characterized in that Ar4、Ar5、Ar6At least One is selected from following group:
Wherein, R8、R9Independently selected from methyl, ethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substitution or Unsubstituted anthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, takes substituted or unsubstituted phenanthryl It is generation or unsubstituted base, substituted or unsubstituted ferrosin base, substituted or unsubstituted pyridyl group, substituted or unsubstituted phonetic Piperidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazine radical, substitution or not Substituted pyrrole radicals, substituted or unsubstituted benzopyrrole base, substituted or unsubstituted triazolyl, substituted or unsubstituted thiophene Base, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuranyl, takes substituted or unsubstituted furyl Generation or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted quinolyl, substitution Or one of unsubstituted isoquinolyl, substituted or unsubstituted indyl；R10Selected from hydrogen atom, methyl, ethyl, isopropyl Or tert-butyl.
9. a kind of organic electroluminescence device according to claim 7, which is characterized in that Ar5、Ar6It is identical, selected from as follows Group:
Wherein, R8、R9Independently selected from methyl, ethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substitution or Unsubstituted anthryl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, in substituted or unsubstituted pyrazinyl One kind；R10Selected from hydrogen atom, methyl, ethyl, isopropyl or tert-butyl.
10. a kind of organic electroluminescence device according to claim 7, which is characterized in that Ar4Selected from substituted or unsubstituted Phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted Triphenylene, substituted or unsubstituted acridinyl, substituted or unsubstituted phenoxazine base, substituted or unsubstituted phenthazine Base, substituted or unsubstituted phenoxazine thiophene base, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazyl, substitution do not take The pyrenyl in generation, substituted or unsubstituted ferrosin base, substituted or unsubstituted base, substituted or unsubstituted acenaphthenyl, substitution or Unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazine Base, substituted or unsubstituted triazine radical, substituted or unsubstituted pyrrole radicals, substituted or unsubstituted benzopyrrole base, replace or Unsubstituted triazolyl, substituted or unsubstituted thienyl, substituted or unsubstituted furyl, substituted or unsubstituted benzo thiophene Pheno base, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzo One of furyl.
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