CN108658980A - A kind of aromatic amine compounds and its organic electroluminescence device containing phenanthroline - Google Patents

A kind of aromatic amine compounds and its organic electroluminescence device containing phenanthroline Download PDF

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CN108658980A
CN108658980A CN201810476673.2A CN201810476673A CN108658980A CN 108658980 A CN108658980 A CN 108658980A CN 201810476673 A CN201810476673 A CN 201810476673A CN 108658980 A CN108658980 A CN 108658980A
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aromatic amine
amine compounds
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周雯庭
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 aromatic amine compounds and its organic electroluminescence device containing phenanthroline, is related to organic optoelectronic materials technology.Such compounds process for production thereof is simple, raw material is easy to get, with good thermal stability and chemical stability, with high hole mobility, stability and good film-forming property, also there is suitable highest occupied molecular orbital energy level, high T1 values and high refractive index, it is applied in OLED device as luminous auxiliary layer and hole transmission layer, the equalizing charge in luminescent layer may be implemented, to significantly improve the luminous efficiency, heat resistance and service life of device, the driving voltage that device can also be reduced simultaneously, is the OLED material of a kind of function admirable.

Description

A kind of aromatic amine compounds and its organic electroluminescence device containing phenanthroline
Technical field
The present invention relates to organic photoelectrical material technical fields, and in particular to a kind of aromatic amine compounds containing phenanthroline And its organic electroluminescence device.
Background technology
In general, organic electroluminescent (OLED) device is by one layer or more between anode, cathode and anode and cathode Organic thin film layer is constituted.To when applying voltage between two electrodes, electronics is injected into light-emitting zone from cathode side, and hole is noted from anode-side Enter to light-emitting zone, the two in light-emitting zone in conjunction with and become excited state, sent out when excited state restores to ground state Light.Therefore, electronics or hole, the opening in conjunction with easy compound for making electronics and hole expeditiously are transmitted to light-emitting zone Hair is important in terms of obtaining high efficiency OLED device.
In addition, driving OLED device with lower voltage, power consumption can be effectively reduced, and then shine to OLED device Efficiency and service life make moderate progress.It is necessary to have the high mobilities for electronics and/or hole for the reduction of driving voltage Charge transport materials.
Currently, as hole transmission layer compound be mostly containing fluorenes, carbazole, dibenzofurans, dibenzothiophenes, other The aromatic amine compounds of aryl or heteroaryl, still, the hole mobility of these compounds is not good enough, it is desirable that exploitation has more high-altitude The compound of cave mobility.
Invention content
In view of the above-mentioned problems existing in the prior art, the present invention provide a kind of aromatic amine compounds containing phenanthroline and Its organic electroluminescence device.
The present invention provides a kind of aromatic amine compounds containing phenanthroline, shown in structural formula such as formula (I)：
Wherein, L is selected from singly-bound, the substituted or unsubstituted divalent aryls of C6~C30, C3~C30 substituted or unsubstituted two Valence heteroaryl；Ar1、Ar2Independently selected from the substituted or unsubstituted aryl of C6~C60, the substituted or unsubstituted heteroaryls of C3~C60 Base or Ar1With Ar2It is connected to form nitrogenous five-ring heterocycles.
Preferably, the aromatic amine compounds containing phenanthroline have structure shown in logical formula (II) or (III)：
Wherein, L is selected from singly-bound, the substituted or unsubstituted divalent aryls of C6~C30, C3~C30 substituted or unsubstituted two Valence heteroaryl；R1、R2、R3、R4、R5、R6、R7、R8、R9、R10It does not take independently selected from hydrogen, deuterium, cyano, halogen, C1~C4 substitutions or The substituted or unsubstituted alkoxy of alkyl, C1~C4 in generation, the substituted or unsubstituted aryl of C6~C30, C3~C60 substitutions or not Substituted heteroaryl or R1、R2、R3、R4、R5、R6、R7、R8、R9、R10Two substituent groups of arbitrary neighborhood can be connected to form Ring.
Preferably, the L is selected from singly-bound or following group：
Wherein, Z1、Z2、Z3、Z4、Z5、Z6、Z7、Z8Independently selected from hydrogen, deuterium, cyano, fluorine atom, methyl, ethyl, positive third Base, isopropyl, normal-butyl, sec-butyl, isobutyl group, tertiary butyl.
Preferably, the aromatic amine compounds containing phenanthroline have structure shown in following general formula：
Wherein, R1、R2、R3、R4、R5、R6、R7、R8、R9、R10Independently selected from hydrogen, deuterium, cyano, fluorine atom, C1~C4 substitutions Or the substituted or unsubstituted aryl of unsubstituted alkyl, methoxyl group, C6~C30, the substituted or unsubstituted heteroaryls of C3~C60, Or R1、R2、R3、R4、R5、R6、R7、R8、R9、R10Two substituent groups of arbitrary neighborhood can be connected to form five-membered ring or hexatomic ring.
Most preferably, the aromatic amine compounds containing phenanthroline appointing in HT1~HT91 as follows Meaning is a kind of：
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device include cathode, anode and The one or more organic matter layers being placed between the cathode and the anode；Contain neighbour containing described in the organic matter layer The aromatic amine compounds of ferrosin.
Preferably, the auxiliary layer that shines is contained in the organic matter layer；Contain containing described in the luminous auxiliary layer There are the aromatic amine compounds of phenanthroline.
It is furthermore preferred that containing hole transmission layer simultaneously in the organic matter layer；Containing in the hole transmission layer The aromatic amine compounds containing phenanthroline stated.
Beneficial effects of the present invention：
Aromatic amine compounds provided by the invention containing phenanthroline, formation ammonium ion free radical makes under electric field action It is with high hole mobility.In addition, such compound also have good stability and film forming, and be suitble to Highest occupied molecular orbital energy level, high T1 values and high refractive index can be used as luminous auxiliary layer applied in OLED device, with reality Equalizing charge in existing luminescent layer, moreover it is possible to improve the luminous efficiency, heat resistance and service life of OLED device, while reduce OLED The driving voltage of device is the OLED material of a kind of function admirable.
Specific implementation mode
Present invention firstly provides a kind of aromatic amine compounds containing phenanthroline, structure formula (I) is as follows：
Wherein, L is selected from singly-bound, the substituted or unsubstituted divalent aryls of C6~C30, the substituted or unsubstituted divalent of C3-C30 Heteroaryl；Ar1、Ar2Independently selected from the substituted or unsubstituted aryl of C6~C60, the substituted or unsubstituted heteroaryls of C3~C60, Or Ar1With Ar2It is connected to form nitrogenous five-ring heterocycles.
Preferably, the aromatic amine compounds containing phenanthroline have structure shown in logical formula (II) or (III)：
Wherein, L is selected from singly-bound, the substituted or unsubstituted divalent aryls of C6~C30, the substituted or unsubstituted divalent of C3-C30 Heteroaryl；R1、R2、R3、R4、R5、R6、R7、R8、R9、R10Replace independently selected from hydrogen, deuterium, cyano, halogen, C1~C4 or unsubstituted Alkyl, the substituted or unsubstituted alkoxies of C1~C4, the substituted or unsubstituted aryl of C6~C30, C3~C60 substitution or do not take The heteroaryl or R in generation1、R2、R3、R4、R5、R6、R7、R8、R9、R10Two substituent groups of arbitrary neighborhood can be connected to form ring.
Preferably, the L is selected from singly-bound or following group：
Wherein, Z1、Z2、Z3、Z4、Z5、Z6、Z7、Z8Independently selected from hydrogen, deuterium, cyano, fluorine atom, methyl, ethyl, positive third Base, isopropyl, normal-butyl, sec-butyl, isobutyl group, tertiary butyl.
Preferably, the aromatic amine compounds containing phenanthroline have structure shown in following general formula：
Wherein, R1、R2、R3、R4、R5、R6、R7、R8、R9、R10Independently selected from hydrogen, deuterium, cyano, fluorine atom, C1~C4 substitutions Or the substituted or unsubstituted aryl of unsubstituted alkyl, methoxyl group, C6~C30, the substituted or unsubstituted heteroaryls of C3~C60, Or R1、R2、R3、R4、R5、R6、R7、R8、R9、R10Two substituent groups of arbitrary neighborhood can be connected to form five-membered ring or hexatomic ring.
Aryl of the present invention refer to aromatic hydrocarbon molecule an aromatic core carbon on remove a hydrogen atom 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 of aryl aromatic core carbon is replaced by hetero atom General name, the hetero atom include but 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 refer to aromatic hydrocarbon molecule two aromatic core carbon on respectively remove a hydrogen atom 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 of divalent aryl aromatic core carbon is replaced to obtain by hetero atom Group general name, the hetero atom includes but 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 sub-pyridyl group, sub- quinolyl, sub- carbazyl, sub- thienyl, sub- benzo can be selected from 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 removing a hydrogen atom in alkane molecule, can be straight chain alkane Base, branched alkyl, naphthenic base, such as methyl, ethyl, propyl, isopropyl, normal-butyl, isobutyl group, sec-butyl, uncle can be selected from Butyl, amyl, isopentyl, cyclopenta, cyclohexyl etc., but not limited to this.
Alkoxy of the present invention refers to-O- alkyl, wherein the alkyl is as previously defined.
Nitrogenous five-ring heterocycles of the present invention refer to substituted or unsubstituted carbazole.
Specifically, the aromatic amine compounds containing phenanthroline are arbitrary in HT1~HT91 as follows It is a kind of：
Some specific constructive forms of the aromatic amine compounds of the present invention containing phenanthroline are enumerated above, but Every based on structure shown in listed general formula the invention is not limited in these listed chemical constitutions, substituent group is institute as above The group of restriction should be all included.
The preparation method of aromatic amine compounds of the present invention containing phenanthroline can pass through following synthetic route system It is standby to obtain：
Wherein, L is selected from singly-bound, the substituted or unsubstituted divalent aryls of C6~C30, the substituted or unsubstituted divalent of C3-C30 Heteroaryl；Ar1、Ar2Independently selected from the substituted or unsubstituted aryl of C6~C60, C3~C60 it is substituted or unsubstituted miscellaneous Aryl or Ar1With Ar2It is connected to form nitrogenous five-ring heterocycles.
Bromo- 1, the 10- phenanthrolines (Y1) of 4- are reacted with connection pinacol borate, generate intermediate A；Then intermediate A Suzuki occurs with I-L-Br to react, obtains intermediate M；Finally, intermediate M with contain the Ar1And Ar2Aromatic amine compound Pass through Buchwald-Hartwig coupling reactions, you can obtain target compound (I).
The present invention does not have special limitation, use well-known to those skilled in the art the above-mentioned reaction condition respectively reacted Reaction condition, the preparation method is simple, and raw material is easy to get.
The present invention further provides a kind of organic electroluminescence device, the organic electroluminescence device include cathode, Anode and the one or more organic matter layers being placed between the cathode and the anode；Contain the present invention in the organic matter layer The aromatic amine compounds containing phenanthroline, preferably comprise in the organic matter layer hole injection layer, hole transmission layer, At least one layer in luminous auxiliary layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer；Preferably, described to have Containing the auxiliary layer that shines in machine nitride layer, the luminous auxiliary layer contains between luminescent layer and anode, and containing described The aromatic amine compounds of phenanthroline；Preferably, contain hole transmission layer, the hole transmission layer in the organic matter layer simultaneously Between the luminous auxiliary layer and anode, and contain the aromatic amine compounds containing phenanthroline.
According to the present invention, the device architecture of use is preferred, Ke Yiwei：Transparent glass is as anode；4,4', 4 "-three [2- naphthylphenyls amino] triphenylamine (2-TNATA) is used as hole injection layer；N, N'- diphenyl-N, N'- (1- naphthalenes) -1, 1'- biphenyl -4,4'- diamines (NPB) or the compounds of this invention (HT1~HT91) are used as hole transmission layer；The compounds of this invention (HT1~HT91) is as the auxiliary layer that shines；(9- carbazoles) biphenyl of 4,4'- bis- (CBP) and two (1- phenyl-isoquinolin) (levulinics Ketone) close iridium ((piq)2Ir (acac)) with 95:The mixture of 5 weight ratio is as luminescent layer；Bis- (2- methyl -8-hydroxyquinoline - N1, O8)-(1,1'- biphenyl -4- hydroxyls) aluminium (BAlq) be used as hole blocking layer；8-hydroxyquinoline aluminium (Alq3) passed as electronics Defeated layer；LiF is as electron injecting layer；Al is as cathode.
The organic electroluminescence device can be used for the application neck such as flat-panel monitor, lighting source, direction board, signal lamp Domain.
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 according to the present invention.
The present invention is not particularly limited the 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.
Embodiment 1：The preparation of intermediate A
By the bromo- 1,10- phenanthrolines (Y1) of 12.96g (50mmol) 4-, 15.24g (60mmol) connection boric acid pinacol ester, 1.10g (1.5mmol) [bis- (diphenylphosphino) ferrocene of 1,1'-] palladium chlorides and 14.72g
(150mmol) potassium acetate is dissolved in 328ml toluene, and under an argon, back flow reaction 12 hours is cooled to room temperature Afterwards, diatom soil hopper is crossed, solvent is removed, residue recrystallizes in heptane, obtains intermediate A
(13.17g, 43mmol).
Embodiment 2：The preparation of intermediate M
The preparation of intermediate M-1：By 12.25g (40mmol) intermediate A, 11.33g (40mmol) to bromo-iodobenzene, 0.62g In (0.53mmol) tetrakis triphenylphosphine palladium, 115ml toluene and 56ml aqueous sodium carbonates (2M) input flask, back flow reaction 8 Hour, it is cooled to room temperature, is extracted with toluene, organic phase saturated common salt water washing is dry, is purified by column chromatography, finally Obtain intermediate M-1 (10.59g, 31.6mmol).
Intermediate M-2 to intermediate M-7 can be prepared by the above method.
Embodiment 3：The preparation of compound HT1
Under argon atmospher, by 10.06g (30mmol) intermediates M-1,5.08g (30mmol) diphenylamines, 5.77g (60mmol) Sodium tert-butoxide is dissolved in 300ml dehydrated toluenes, is added with stirring 0.13g (0.6mmol) palladium, 0.16g (0.6mmol) triphen Base phosphine reacts 8 hours at 80 DEG C.It after cooling, is filtered by diatomite/silica gel funnel, filtrate has by being evaporated under reduced pressure removal Solvent, it is residue obtained to be recrystallized in toluene, it is dry, you can to obtain 11.44g (27mmol) compound HT1, yield is 90%.Mass spectrum m/z：423.89 (calculated values：423.52).Theoretical elemental content (%) C30H21N3：C,85.08；H,5.00；N, 9.92.Survey constituent content (%)：C,85.06；H,5.02；N,9.88.The above results confirm that it is target product to obtain product.
Embodiment 4：The preparation of compound HT6
Diphenylamines is replaced with to two (4- tert-butyl-phenyls) amine of equimolar amounts, other steps are same as Example 3, It can be obtained compound HT6.Mass spectrum m/z：536.83 (calculated values：535.74).Theoretical elemental content (%) C38H37N3：C, 85.19；H,6.96；N,7.84.Survey constituent content (%)：C,85.15；H,6.98；N,7.81.The above results confirmation is produced Object is target product.
Embodiment 5：The preparation of compound HT14
Diphenylamines is replaced with to the carbazole of equimolar amounts, other steps are same as Example 3, you can obtain compound HT14.Mass spectrum m/z：421.91 (calculated values：421.50).Theoretical elemental content (%) C30H19N3：C,85.49；H,4.54；N, 9.97.Survey constituent content (%)：C,85.54；H,4.50；N,9.99.The above results confirm that it is target product to obtain product.
Embodiment 6：The preparation of compound HT27
Intermediate M-1 is replaced with to the intermediate M-2 of equimolar amounts, diphenylamines is replaced with to the N- benzene of equimolar amounts Base-[1,1 ':4 ', 1 "-terphenyl] -4- amine, other steps are same as Example 3, you can obtain compound HT27.Mass spectrum m/ z：574.84 (calculated values：575.72).Theoretical elemental content (%) C42H29N3：C,87.62；H,5.08；N,7.30.Survey element Content (%)：C,87.59；H,5.05；N,7.33.The above results confirm that it is target product to obtain product.
Embodiment 7：The preparation of compound HT36
The preparation of compound N 1：It is under argon atmospher, 5.91g (50mmol) p-aminophenyls nitrile, 19.87g (50mmol) 2- is bromo- 9,9 '-diphenylfluorenes, 9.60g (100mmol) sodium tert-butoxide are dissolved in 500ml dehydrated toluenes, are added with stirring 0.23g (1mmol) palladium, 0.20g (1mmol) triphenylphosphine, react 8 hours at 80 DEG C.After cooling, leaked by diatomite/silica gel Bucket filtering, filtrate removes organic solvent by vacuum distillation, residue obtained to be recrystallized in toluene, dry, you can to obtain 19.34g (44.50mmol) compound N 1.
Intermediate M-1 is replaced with to the intermediate M-2 of equimolar amounts, diphenylamines is replaced with to the chemical combination of equimolar amounts Object N1, other steps are same as Example 3, you can obtain compound HT36.Mass spectrum m/z：693.38 (calculated values： 688.83).Theoretical elemental content (%) C50H32N4：C,87.18；H,4.68；N,8.13.Survey constituent content (%)：C, 87.15；H,4.66；N,8.16.The above results confirm that it is target product to obtain product.
Embodiment 8：The preparation of compound HT48
The preparation of compound N 2：Under argon atmospher, by 7.16g (50mmol) naphthalidine, 13.16g (50mmol) 3- bromine hexichol Bithiophene, 9.60g (100mmol) sodium tert-butoxide are dissolved in 500ml dehydrated toluenes, are added with stirring 0.23g (1mmol) acetic acid Palladium, 0.20g (1mmol) triphenylphosphine, react 8 hours at 80 DEG C.After cooling, filtered by diatomite/silica gel funnel, filtrate Organic solvent is removed by vacuum distillation, it is residue obtained to be recrystallized in toluene, it is dry, you can to obtain 14.32g (44mmol) changes Close object N2.
Intermediate M-1 is replaced with to the intermediate M-3 of equimolar amounts, diphenylamines is replaced with to the chemical combination of equimolar amounts Object N2, other steps are same as Example 3, you can obtain compound HT48.Mass spectrum m/z：609.03 (calculated values： 607.78).Theoretical elemental content (%) C42H29N3S：C,83.00；H,4.81；N,6.91；S,5.27.Survey constituent content (%)：C,83.04；H,4.82；N,6.93；S,5.29.The above results confirm that it is target product to obtain product.
Embodiment 9：The preparation of compound HT53
Intermediate M-1 is replaced with to the intermediate M-4 of equimolar amounts, diphenylamines is replaced with the 3,6- of equimolar amounts Diphenyl -9H- carbazoles, other steps are same as Example 3, you can obtain compound HT53.Mass spectrum m/z：611.32 (calculate Value：609.68).Theoretical elemental content (%) C42H25F2N3：C,82.74；H,4.13；F,6.23；N,6.89.Survey constituent content (%)：C,82.71；H,4.15；F,6.26；N,6.87.The above results confirm that it is target product to obtain product.
Embodiment 10：The preparation of compound HT62
Intermediate M-1 is replaced with to the intermediate M-5 of equimolar amounts, diphenylamines is replaced with the two of equimolar amounts (4- xenyls) amine, other steps are same as Example 3, you can obtain compound HT62.Mass spectrum m/z：658.37 (calculate Value：651.81).Theoretical elemental content (%) C48H33N3：C,88.45；H,5.10；N,6.45.Survey constituent content (%)：C, 88.42；H,5.07；N,6.49.The above results confirm that it is target product to obtain product.
Embodiment 11：The preparation of compound HT73
Intermediate M-1 is replaced with to the intermediate M-6 of equimolar amounts, the N- that diphenylamines is replaced with to equimolar amounts is bis- Phenyl -4-N ', N '-diphenyl-Isosorbide-5-Nitrae-diphenylamines, other steps are same as Example 3, you can obtain compound HT73.Matter Compose m/z：718.06 (calculated values：716.89).Theoretical elemental content (%) C52H36N4：C,87.12；H,5.06；N,7.82.Actual measurement Constituent content (%)：C,87.10；H,5.09；N,7.84.The above results confirm that it is target product to obtain product.
Embodiment 12：The preparation of compound HT86
The preparation of compound N 3：Under argon atmospher, simultaneously by 7.16g (50mmol) 2- naphthylamines, 15.66g (50mmol) 5- bromobenzenes [B] naphtho- [1,2-D] thiophene, 9.60g (100mmol) sodium tert-butoxide are dissolved in 500ml dehydrated toluenes, are added with stirring 0.23g (1mmol) palladium, 0.20g (1mmol) triphenylphosphine, react 8 hours at 80 DEG C.After cooling, leaked by diatomite/silica gel Bucket filtering, filtrate removes organic solvent by vacuum distillation, residue obtained to be recrystallized in toluene, dry, you can to obtain 15.77g (42mmol) compound N 3.
Intermediate M-1 is replaced with to the intermediate M-7 of equimolar amounts, diphenylamines is replaced with to the chemical combination of equimolar amounts Object N3, other steps are same as Example 3, you can obtain compound HT86.Mass spectrum m/z：677.29 (calculated values： 679.84).Theoretical elemental content (%) C48H29N3S：C,84.80；H,4.30；N,6.18；S,4.72.Survey constituent content (%)：C,84.77；H,4.26；N,6.22；S,4.75.The above results confirm that it is target product to obtain product.
Embodiment 13：The preparation of compound HT91
The preparation of compound N 4：Under argon atmospher, by 9.66g (50mmol) 2- phenanthryl amine, 14.86g (50mmol) 9- bromo- two Benzo [2,1-B] furans, 9.60g (100mmol) sodium tert-butoxide are dissolved in 500ml dehydrated toluenes, are added with stirring 0.23g (1mmol) palladium, 0.20g (1mmol) triphenylphosphine, react 8 hours at 80 DEG C.After cooling, leaked by diatomite/silica gel Bucket filtering, filtrate removes organic solvent by vacuum distillation, residue obtained to be recrystallized in toluene, dry, you can to obtain 17.0g (41.5mmol) compound N 4.
Intermediate M-1 is replaced with to the intermediate M-7 of equimolar amounts, diphenylamines is replaced with to the 4- of equimolar amounts Bromo- 1,10- phenanthrolines, other steps are same as Example 3, you can obtain compound HT91.Mass spectrum m/z：288.94 (meters Calculation value：587.68).Theoretical elemental content (%) C42H25N3O：C,85.84；H,4.29；N,7.15；O,2.72.Actual measurement element contains It measures (%)：C,85.81；H,4.25；N,7.18；O,2.76.The above results confirm that it is target product to obtain product.
Embodiment 14：The preparation of red organic electroluminescence device 1
First, it is 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 compound HT1 of 20nm as luminous auxiliary layer on hole transmission layer；Then, in above-mentioned luminous auxiliary layer On with weight ratio be 95:5 CBP and (piq)2Ir (acac) vacuum depositions are as luminescent layer, thickness 30nm；Then, upper It states and hole blocking layer is formed with the thickness vacuum deposition BAlq of 10nm on luminescent layer；With 40nm's on above-mentioned hole blocking layer Thickness vacuum deposition Alq3To form electron transfer layer；Then, 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.
Embodiment:15：The preparation of red organic electroluminescence device 2
Compound HT1 is replaced with compound HT6, other steps are identical as embodiment 14.
Embodiment 16：The preparation of red organic electroluminescence device 3
Compound HT1 is replaced with compound HT27, other steps are identical as embodiment 14.
Embodiment 17：The preparation of red organic electroluminescence device 4
Compound HT1 is replaced with compound HT39, other steps are identical as embodiment 14.
Embodiment 18：The preparation of red organic electroluminescence device 5
Compound HT1 is replaced with compound HT47, other steps are identical as embodiment 14.
Embodiment 19：The preparation of red organic electroluminescence device 6
Compound HT1 is replaced with compound HT53, other steps are identical as embodiment 14.
Embodiment 20：The preparation of red organic electroluminescence device 7
Compound HT1 is replaced with compound HT64, other steps are identical as embodiment 14.
Embodiment 21：The preparation of red organic electroluminescence device 8
Compound HT1 is replaced with compound HT73, other steps are identical as embodiment 14.
Embodiment 22：The preparation of red organic electroluminescence device 9
Compound HT1 is replaced with compound HT86, other steps are identical as embodiment 14.
Embodiment 23：The preparation of red organic electroluminescence device 10
Compound HT1 is replaced with compound HT91, other steps are identical as embodiment 14.
Embodiment 24：The preparation of red organic electroluminescence device 11
First, it is 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 compound HT1 of 60nm on above-mentioned hole injection layer；It Afterwards, on the hole transport layer using the thickness vacuum evaporation compound HT39 of 20nm as luminous auxiliary layer；Then, it shines above-mentioned With weight ratio for 95 on auxiliary layer:5 CBP and (piq)2Ir (acac) vacuum depositions are as luminescent layer, thickness 30nm；It connects It, 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；Then, LiF is deposited using the thickness of 0.2nm to note as electronics Enter layer；Finally, cathode is formed with the thickness depositing Al of 150nm.
Embodiment 25：The preparation of red organic electroluminescence device 12
HT1 is replaced with compound HT6, other steps are identical as embodiment 24.
Embodiment 26：The preparation of red organic electroluminescence device 13
HT1 is replaced with compound HT27, other steps are identical as embodiment 24.
Embodiment 27：The preparation of red organic electroluminescence device 14
HT1 is replaced with compound HT39, other steps are identical as embodiment 24.
Embodiment 28：The preparation of red organic electroluminescence device 15
HT1 is replaced with compound HT47, other steps are identical as embodiment 24.
Embodiment 29：The preparation of red organic electroluminescence device 16
HT1 is replaced with compound HT53, other steps are identical as embodiment 24.
Embodiment 30：The preparation of red organic electroluminescence device 17
HT1 is replaced with compound HT64, other steps are identical as embodiment 24.
Embodiment 31：The preparation of red organic electroluminescence device 18
HT1 is replaced with compound HT73, other steps are identical as embodiment 24.
Embodiment 32：The preparation of red organic electroluminescence device 19
HT1 is replaced with compound HT86, other steps are identical as embodiment 24.
Embodiment 33：The preparation of red organic electroluminescence device 20
HT1 is replaced with compound HT91, other steps are identical as embodiment 24.
Comparative example：The preparation of red organic electroluminescence device 21
Other than not forming luminous auxiliary layer this point, luminescent device has been made in method identical with embodiment 14.
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 the aromatic amine compounds provided by the invention containing phenanthroline, have high hole migration Rate, stability and good film-forming property also have suitable highest occupied molecular orbital energy level, high T1 values and refractive index, as Luminous auxiliary layer and hole transmission layer are applied in organic electroluminescence device, can improve luminous efficiency, the heat resistance of device And service life, while the driving voltage of device can also be reduced, it is the luminous organic material of a kind of function admirable.
Obviously, the explanation of above example is only intended to facilitate the understanding of the method and its core concept of the invention.It should refer to Go out, it, 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 protection scope of the claims of the present invention.

Claims (8)

1. a kind of aromatic amine compounds containing phenanthroline, which is characterized in that have the structure as shown in logical formula (I)：
Wherein, it is miscellaneous to be selected from singly-bound, the substituted or unsubstituted divalent aryls of C6~C30, the substituted or unsubstituted divalent of C3~C30 by L Aryl；Ar1、Ar2Independently selected from the substituted or unsubstituted aryl of C6~C60, the substituted or unsubstituted heteroaryls of C3~C60, or Person Ar1With Ar2It is connected to form nitrogenous five-ring heterocycles.
2. the aromatic amine compounds according to claim 1 containing phenanthroline, which is characterized in that described contains adjacent phenanthrene The aromatic amine compounds of hello quinoline have structure shown in logical formula (II) or (III)：
Wherein, it is miscellaneous to be selected from singly-bound, the substituted or unsubstituted divalent aryls of C6~C30, the substituted or unsubstituted divalent of C3~C30 by L Aryl；R1、R2、R3、R4、R5、R6、R7、R8、R9、R10It is substituted or unsubstituted independently selected from hydrogen, deuterium, cyano, halogen, C1~C4 The substituted or unsubstituted alkoxy of alkyl, C1~C4, the substituted or unsubstituted aryl of C6~C30, C3~C60 substitutions or unsubstituted Heteroaryl or R1、R2、R3、R4、R5、R6、R7、R8、R9、R10Two substituent groups of arbitrary neighborhood are connected to form ring.
3. the aromatic amine compounds according to claim 1 containing phenanthroline, which is characterized in that the L is selected from singly-bound Or following group：
Wherein, Z1、Z2、Z3、Z4、Z5、Z6、Z7、Z8Independently selected from hydrogen, deuterium, cyano, fluorine atom, methyl, ethyl, n-propyl, different Propyl, normal-butyl, sec-butyl, isobutyl group, tertiary butyl.
4. the aromatic amine compounds according to claim 1 containing phenanthroline, which is characterized in that described contains adjacent phenanthrene The aromatic amine compounds of hello quinoline have structure shown in following general formula：
Wherein, R1、R2、R3、R4、R5、R6、R7、R8、R9、R10Independently selected from hydrogen, deuterium, cyano, fluorine atom, C1~C4 substitution or not Substituted alkyl, methoxyl group, the substituted or unsubstituted aryl of C6~C30, the substituted or unsubstituted heteroaryls of C3~C60, or R1、R2、R3、R4、R5、R6、R7、R8、R9、R10Two substituent groups of arbitrary neighborhood are connected to form five-membered ring or hexatomic ring.
5. the aromatic amine compounds according to claim 1 containing phenanthroline, which is characterized in that described contains adjacent phenanthrene Any one of the aromatic amine compounds of hello quinoline in HT1~HT91 as follows：
6. a kind of organic electroluminescence device, which is characterized in that including cathode, anode and be placed in the cathode and the anode it Between one or more organic matter layers；Containing according to any one of claims 1 to 5 containing adjacent luxuriant and rich with fragrance in the organic matter layer The aromatic amine compounds of hello quinoline.
7. organic electroluminescence device according to claim 6, which is characterized in that containing luminous in the organic matter layer Auxiliary layer；Contain the arylamine class according to any one of claims 1 to 5 containing phenanthroline in the luminous auxiliary layer Close object.
8. organic electroluminescence device according to claim 6, which is characterized in that contain hole in the organic matter layer Transport layer；Contain the arylamine class according to any one of claims 1 to 5 containing phenanthroline in the hole transmission layer Close object.
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WW01 Invention patent application withdrawn after publication