CN108912038A - A kind of aromatic amine compound and its organic electroluminescence device - Google Patents

A kind of aromatic amine compound and its organic electroluminescence device Download PDF

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CN108912038A
CN108912038A CN201810579508.XA CN201810579508A CN108912038A CN 108912038 A CN108912038 A CN 108912038A CN 201810579508 A CN201810579508 A CN 201810579508A CN 108912038 A CN108912038 A CN 108912038A
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unsubstituted
substituted
aromatic amine
amine compound
compound
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杜明珠
蔡辉
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Changchun Haipurunsi Technology Co Ltd
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Abstract

The present invention provides a kind of aromatic amine compound and its organic electroluminescence device, is related to organic optoelectronic materials technology.Aromatic amine compound provided by the invention, with good thermal stability and higher carrier mobility, as the luminous auxiliary layer materials'use between hole transmission layer and luminescent layer, it can reduce the energy level difference between luminescent layer and anodic interface, it is more conducive to realizing the equalizing charge in luminescent layer, excitation purity, luminous efficiency and the service life of device are improved, and reduces the driving voltage of device.

Description

A kind of aromatic amine compound and its organic electroluminescence device
Technical field
The present invention relates to organic photoelectrical material technical fields, and in particular to a kind of aromatic amine compound and its organic electroluminescence hair Optical device.
Background technique
Organic Light Emitting Diode (Organic Light-Emitting Diode, OLED) organic electric laser that is otherwise known as is aobvious Show, is after CRT (Cathode Ray Tube, cathode-ray tube), LCD (Liquid Crystal Display, liquid crystal display Device) after third generation display technology, have high brightness, high contrast, fine definition, wide viewing angle, wide colour gamut, it is ultra-thin, ultralight, Low-power consumption, wide temperature, self-luminous, the advantages that luminous efficiency is high, the reaction time is short, transparent, flexible.Basic structure such as sandwich Structure is made of indium-tin oxide anode, metallic cathode and organic matter layer between the two, is Dual Implantations type luminescent device, will be electric It can be converted into the luminous energy of organic semiconducting materials molecule, it is aobvious with traditional LCD using electroluminescent physical mechanism Show mode difference, OLED is not necessarily to backlight, has self luminous characteristic, the very thin coating of organic material of use and glass base Plate, when a current passes through, these organic materials will shine.
OLED material can be divided into luminescent material, hole mobile material, electron transport material etc. according to the difference of function.It is empty Hole transport materials should usually have low highest occupied molecular orbital (HOMO) value, therefore most of with low T1 value, as a result, The exciton diffusion generated in phosphorescence luminescent layer is eventually led to hole transport bed boundary or hole transmission layer side in luminescent layer Charge in the luminous or luminescent layer of inner boundary is unbalanced, to shine on the interface of hole transmission layer.In hole transport In the case where shining on bed boundary, the excitation purity of organic luminescent device will occurs and efficiency is lower the problem of shortening with the service life.
Summary of the invention
In view of the above-mentioned problems existing in the prior art, the present invention provides a kind of aromatic amine compound and its organic electroluminescent Device.
The present invention provides a kind of aromatic amine compounds, shown in structural formula such as formula (I)：
Wherein, Ar1Selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthryl, One of substituted or unsubstituted two fluorenyl of spiral shell, Ar2Selected from substituted or unsubstituted carbazyl, Ar3Selected from substituted or unsubstituted Phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted One of two fluorenyl of spiral shell, L1、L2、L3Independently selected from singly-bound, the divalent aryl of substituted or unsubstituted C6-C30, substitution Or one of divalent heteroaryl radical of unsubstituted C6-C30.
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 condensed cyclization of both arbitrary neighborhoods in described R2, R3；
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 Ar1Selected from one of group as follows：
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 Ar1Selected from one of following group：
Preferably, the Ar3Selected from one of following group：
Wherein, R8、R9、R10、R11At each occurrence identical or differently selected from hydrogen atom, D-atom, halogen atom, The alkyl of C1~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 R8、R9、R10、R11The condensed cyclization of both middle arbitrary neighborhoods；G, the independent choosing of h, i, j From 0 to 4 integer.
Preferably, the Ar3Selected from one of following group：
Preferably, the L1、L2、L3Independently selected from singly-bound, phenyl, xenyl or naphthalene.
Most preferably, the aromatic amine compound is selected from any one into HT2-286 of HT2-1 as follows：
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device include cathode, anode and The one or more organic compound layers being placed between the cathode and the anode, the organic compound layer contain described Aromatic amine compound.
Beneficial effects of the present invention：
Aromatic amine compound provided by the invention, the derivative simultaneously containing fluorenes, two fluorenes of spiral shell and carbazole, fluorenes, two fluorenes of spiral shell spread out The planar inline benzene unit of the rigidity of biology makes it have high thermal stability and chemical stability, what carbazole compound had Rigid planar structure and big pi-conjugated system, make it have good thermal stability and higher carrier mobility, pass through Ar1、Ar2、 Ar3Between synergistic effect so that the cavity transmission ability and stability of compound get a promotion, realize luminescent layer Interior equalizing charge；Further, by the optimization to carbazole structure, pi-pi accumulation between regulatory molecule has compound and closes Suitable highest occupied molecular orbital energy level and high T1 value, as the luminous auxiliary layer material between hole transmission layer and luminescent layer It uses, can reduce the energy level difference between luminescent layer and anodic interface, be more conducive to realizing the equalizing charge in luminescent layer, Excitation purity, luminous efficiency and the service life of device are improved, and reduces the driving voltage of device.
Specific embodiment
It is clearly and completely described below in conjunction with the technical solution of the specific embodiment of the invention, it is clear that described Embodiment is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, this field Technical staff's every other embodiment obtained without making creative work, belongs to protection model of the invention It encloses.
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.
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.
Aryl of the present invention refers to remove a hydrogen atom on the aromatic core carbon of aromatic hydrocarbon molecule after, be left the total of univalent perssad Claiming, can be monocyclic aryl or fused ring aryl, example may include phenyl, xenyl, naphthalene, anthryl, phenanthryl or pyrenyl etc., but It is without being limited thereto.
Heteroaryl of the present invention refers to the group that one or more aromatic core carbon in aryl are substituted 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, example may include pyridyl group, pyrrole radicals, pyridyl group, thienyl, furyl, indyl, quinolyl, isoquinolyl, benzo thiophene Pheno base, benzofuranyl, dibenzofuran group, dibenzothiophene, carbazyl 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 shown below：
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.
Present invention firstly provides a kind of aromatic amine compound, structure formula (I) is as follows：
Wherein, Ar1Selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthryl, One of substituted or unsubstituted two fluorenyl of spiral shell, Ar2Selected from substituted or unsubstituted carbazyl, Ar3Selected from substituted or unsubstituted Phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted One of two fluorenyl of spiral shell, L1、L2、L3Independently selected from singly-bound, the divalent aryl of substituted or unsubstituted C6-C30, substitution Or one of divalent heteroaryl radical of unsubstituted C6-C30.
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, C1~C30Silylation, C2~C10Alkylamino radical, C6~C30Aryl amine Deng, 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, triphenyl silicon substrate, Trimethyl silicon substrate, trifluoromethyl, phenothiazinyl, phenoxazine group, acridinyl, piperidyl, pyridyl group, pyrazinyl, triazine radical, pyrimidine Base etc., but not limited to this.
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；A is selected from 0 to 4 integer, and b is selected from 0 to 3 integer.Preferably, The R2、R3It is selected from hydrogen atom, D-atom, halogen atom, substituted or unsubstituted C1- identical or differently at each occurrence One of C4 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl or the R2、R3 The condensed cyclization of both middle arbitrary neighborhoods；It is furthermore preferred that the R2、R3It is selected from hydrogen atom, deuterium identical or differently at each occurrence Atom, fluorine atom, chlorine atom, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthalene, xenyl, terphenyl, One of carbazyl or the R2、R3Both middle arbitrary neighborhoods are fused into phenyl ring.
Preferably, the Ar2Selected from one of following group：
Preferably, the Ar1Selected from one of group as follows：
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 Ar1Selected from one of following group：
Preferably, the Ar3Selected from one of following group：
Wherein, R8、R9、R10、R11At each occurrence identical or differently selected from hydrogen atom, D-atom, halogen atom, The alkyl of C1~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 R8、R9、R10、R11The condensed cyclization of both middle arbitrary neighborhoods；G, the independent choosing of h, i, j From 0 to 4 integer.Preferably, the R8、R9、R10、R11At each occurrence identical or differently selected from hydrogen atom, D-atom, Halogen atom, substituted or unsubstituted C1-C4 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3- One of C18 heteroaryl or the R8、R9、R10、R11The condensed cyclization of both middle arbitrary neighborhoods；It is furthermore preferred that the R8、R9、 R10、R11It is selected from hydrogen atom, D-atom, fluorine atom, chlorine atom, methyl, ethyl, positive third identical or differently at each occurrence One of base, isopropyl, tert-butyl, phenyl, naphthalene, xenyl, terphenyl, carbazyl or the R8、R9、R10、R11In Both arbitrary neighborhoods are fused into phenyl ring.
Preferably, the Ar3Selected from one of following group：
Preferably, the L1、L2、L3Independently selected from singly-bound, phenyl, xenyl or naphthalene.
Specifically, the aromatic amine compound is preferably selected from any one of HT2-1 as follows into HT2-286：
It is enumerated above some specific constructive forms of aromatic amine compound of the present invention, but the invention is not limited to These listed chemical structures, all based on structure shown in formula (I), Ar1、Ar2、Ar3And L1、L2、L3It is as defined above Group should be all included.
The preparation method of aromatic amine compound of the present invention can be prepared by conventional coupling reaction, such as can It is 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.
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 present invention is not particularly limited the source of raw material employed in above-mentioned each reaction, can be commercially available Product is prepared using preparation method well-known to those skilled in the art.Aromatic amine compound synthesis step of the present invention Suddenly less, processing it is simple, easy to industrialized production.
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device include cathode, anode and The one or more organic compound layers being placed between the cathode and the anode contain this hair in the organic compound layer The bright aromatic amine compound.It may include hole injection layer, hole transmission layer, luminous auxiliary in the organic compound layer Layer, luminescent layer, hole blocking layer, electron transfer layer, at least one layer in electron injecting layer；It is preferred that in the organic compound layer Containing hole transmission layer and luminous auxiliary layer, the hole transmission layer is between the anode and the luminescent layer, the hair Light auxiliary layer is between the hole transmission layer and the luminescent layer, in the preferably described hole transmission layer and luminous auxiliary layer At least one layer contains the aromatic amine compound；Contain the aromatic amine compound in the more preferable luminous auxiliary layer.
However, the structure of organic electroluminescence device of the present invention is not limited to this, as an example, in the present invention Device architecture used in the examples can be：Transparent glass is as anode；4,4', 4 "-three [2- naphthylphenyl amino] Triphenylamine (2-TNATA) is used as hole injection layer；N, N'- diphenyl-N, N'- (1- naphthalene) -1,1'- biphenyl -4,4'- diamines (NPB) it is used as hole transmission layer；Aromatic amine compound of the present invention is as the auxiliary layer that shines；4,4'- bis- (9- carbazole) biphenyl (CBP) Iridium ((piq) is closed with two (1- phenyl-isoquinolin) (acetylacetone,2,4-pentanediones)2Ir (acac)) with 95:The mixture conduct of 5 weight ratio Luminescent layer；Bis- (2- methyl -8- oxyquinoline-N1, O8)-(1,1'- biphenyl -4- hydroxyl) aluminium (BAlq) are used as hole blocking layer； 8-hydroxyquinoline aluminium (Alq3) it is used as electron transfer layer；LiF is as electron injecting layer；Al is as cathode.
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.
The present invention is not particularly limited the source of raw material employed in following embodiment, can for commercial product or It is prepared using preparation method well-known to those skilled in the art.
Embodiment 1：The preparation of compound 1
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, Filtrate 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 values：929.38).Theoretical elemental content (%) C70H47N3：C,90.39；H,5.09；N,4.52.It surveys 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.It surveys 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.It surveys 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 values：979.39).Theoretical elemental content (%) C74H49N3：C, 90.67； H,5.04；N,4.29.It surveys 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 values：979.39).Theoretical elemental content (%) C74H49N3：C, 90.67； H,5.04；N,4.29.It surveys 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 values：979.39).Theoretical elemental content (%) C74H49N3：C, 90.67； H,5.04；N,4.29.It surveys 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 (calculating Value： 1041.50).Theoretical elemental content (%) C78H63N3：C,89.88；H,6.09；N,4.03.It surveys constituent content (%)：C, 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 (calculating Value： 1041.50).Theoretical elemental content (%) C78H63N3：C,89.88；H,6.09；N,4.03.It surveys constituent content (%)：C, 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 values：880.38).Theoretical elemental content (%) C67H48N2：C, 91.33； H,5.49；N,3.18.It surveys constituent content (%)：C,91.28；H,5.46；N,3.17.The above results confirm to obtain Product 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 values： 992.51).Theoretical elemental content (%) C75H64N2：C,90.69；H,6.49；N,2.82.It surveys constituent content (%)：C, 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 values： 956.41).Theoretical elemental content (%) C73H52N2：C,91.60；H,5.48；N,2.93.It surveys constituent content (%)：C, 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 values： 930.40).Theoretical elemental content (%) C71H50N2：C,91.58；H,5.41；N,3.01.It surveys constituent content (%)：C, 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 values： 930.40).Theoretical elemental content (%) C71H50N2：C,91.58；H,5.41；N,3.01.It surveys constituent content (%)：C, 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 values： 992.51).Theoretical elemental content (%) C75H64N2：C,90.69；H,6.49；N,2.82.It surveys constituent content (%)：C, 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 values：764.32).Theoretical elemental content (%) C58H40N2：C, 91.07； H,5.27；N,3.66.It surveys 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 values： 926.46).Theoretical elemental content (%) C70H58N2：C,90.67；H,6.31；N,3.02.It surveys constituent content (%)：C, 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 values： 890.37).Theoretical elemental content (%) C68H46N2：C,91.65；H,5.20；N,3.14.It surveys constituent content (%)：C, 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 values：870.31).Theoretical elemental content (%) C64H42N2S：C, 88.24；H,4.86；N,3.22；S,3.68.It surveys 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 values： 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 values：854.33).Theoretical elemental content (%) C64H42N2O： C, 89.90；H,4.95；N,3.28；O,1.87.It surveys 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 (calculate 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 values：929.38).Theoretical elemental content (%) C70H47N3：C,90.39； H,5.09；N,4.52.It surveys 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.It surveys 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 (calculate Value： 880.38).Theoretical elemental content (%) C67H48N2：C,91.33；H,5.49；N,3.18.It surveys constituent content (%)： C, 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 values：814.33).Theoretical elemental content (%) C62H42N2：C, 91.37； H,5.19；N,3.44.It surveys 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 values：764.32).Theoretical elemental content (%) C58H40N2： C, 91.07；H,5.27；N,3.66.It surveys 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 values：813.31).Theoretical elemental content (%) C61H39N3： C, 90.01；H,4.83；N,5.16.It surveys 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 values：691.30).Theoretical elemental content (%) C51H37N3：C, 88.54；H,5.39；N,6.07.It surveys constituent content (%)：C,88.50；H,5.39；N,6.06.The above results confirmation is produced Object is target product.
Compare Application Example 29：The preparation of luminescent device 1
Firstly, being formed with the thickness vacuum deposition 2-TNATA of 60nm in the ITO layer (anode) for being formed in organic substrate Hole injection layer；Hole transmission layer is formed with the thickness vacuum evaporation NPB of 60nm on above-mentioned hole injection layer；In above-mentioned sky With weight ratio for 95 in the transport layer of cave:5 CBP and (piq)2Ir (acac) vacuum deposition is as luminescent layer, with a thickness of 30nm； Hole blocking layer is formed with the thickness vacuum deposition BAlq of 10nm on above-mentioned luminescent layer；On above-mentioned hole blocking layer with The thickness vacuum deposition Alq of 40nm3To form electron transfer layer；LiF is deposited as electron injecting layer using the thickness of 0.2nm；Most Afterwards, cathode is formed with the thickness depositing Al of 150nm.
Application Example 30-64：The preparation of luminescent device 2-36
Firstly, being formed with the thickness vacuum deposition 2-TNATA of 60nm in the ITO layer (anode) for being formed in organic substrate Hole injection layer；Hole transmission layer is formed with the thickness vacuum evaporation NPB of 60nm on above-mentioned hole injection layer；Later, exist Using the thickness vacuum evaporation aromatic amine compound of the present invention of 20nm as luminous auxiliary layer on hole transmission layer；Then, exist With weight ratio for 95 on above-mentioned luminous auxiliary layer:5 CBP and (piq)2Ir (acac) vacuum deposition as luminescent layer, with a thickness of 30nm；Then, hole blocking layer is formed with the thickness vacuum deposition BAlq of 10nm on above-mentioned luminescent layer；It is hindered in above-mentioned hole With the thickness vacuum deposition Alq of 40nm in barrier3To form electron transfer layer；Then, using the thickness of 0.2nm deposit LiF as Electron injecting layer；Finally, forming cathode with the thickness depositing Al of 150nm.
Compound involved in the embodiment of the present invention and comparative example is as follows：
The luminescent properties for the organic electroluminescence device that the embodiment of the present invention is prepared are as shown in the table：
The above result shows that aromatic amine compound of the invention is applied to organic electroluminescence as the auxiliary layer that shines In part, the luminous efficiency of device can be improved, reduce the driving voltage of device, be the luminous organic material of a kind of function admirable.
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, these improvement and modification are also fallen within the scope of the present invention.

Claims (10)

1. a kind of aromatic amine compound, which is characterized in that have structure shown in logical formula (I) as follows：
Wherein, Ar1Selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthryl, substitution Or one of unsubstituted two fluorenyl of spiral shell, Ar2Selected from substituted or unsubstituted carbazyl, Ar3Selected from substituted or unsubstituted benzene Base, substituted or unsubstituted naphthalene, substituted or unsubstituted anthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spiral shell One of two fluorenyls, L1、L2、L3Independently selected from singly-bound, substituted or unsubstituted C6-C30 divalent aryl, replace or not One of substituted divalent heteroaryl radical of C6-C30.
2. aromatic amine compound according to claim 1, which is characterized in that the Ar2It is as follows 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.
3. aromatic amine compound according to claim 1, which is characterized in that the Ar2One in following group Kind：
4. aromatic amine compound according to claim 1, which is characterized in that the Ar1In group as follows It is a kind of：
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.
5. aromatic amine compound according to claim 1, which is characterized in that the Ar1One in following group Kind：
6. aromatic amine compound according to claim 1, which is characterized in that the Ar3One in following group Kind：
Wherein, R8、R9、R10、R11At each occurrence identical or differently selected from hydrogen atom, D-atom, halogen atom, C1~ The alkyl of C10, the alkoxy of C1~C10, the aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C3~C30 One of heteroaryl；Or the R8、R9、R10、R11The condensed cyclization of both middle arbitrary neighborhoods；G, h, i, j are independent is selected from 0 to 4 Integer.
7. aromatic amine compound according to claim 1, which is characterized in that the Ar3One in following group Kind：
8. aromatic amine compound according to claim 1, which is characterized in that the L1、L2、L3Independently selected from singly-bound, Phenyl, xenyl or naphthalene.
9. aromatic amine compound according to claim 1, which is characterized in that selected from HT2-1 as follows into HT2-286 Any one：
10. a kind of organic electroluminescence device, which is characterized in that the organic electroluminescence device includes cathode, anode and sets One or more organic compound layers between the cathode and the anode, the organic compound layer, which contains, has the right to want Seek the described in any item aromatic amine compounds of 1-9.
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