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CN109574857A - A kind of organic electroluminescence device aromatic amine compound and its organic electroluminescence device - Google Patents

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

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Publication number
CN109574857A
CN109574857A CN201811439263.7A CN201811439263A CN109574857A CN 109574857 A CN109574857 A CN 109574857A CN 201811439263 A CN201811439263 A CN 201811439263A CN 109574857 A CN109574857 A CN 109574857A
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organic electroluminescence
electroluminescence device
unsubstituted
substituted
aromatic amine
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董秀芹
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 aromatic amine compound and its organic electroluminescence device, is related to organic optoelectronic materials technology.The present invention ipsilateral connection two substituted or unsubstituted 3 in aromatic amine main structure, 5- diphenyl benzene group obtains organic electroluminescence device aromatic amine compound of the present invention, its refractive index is high, good film-forming property, thermal stability is good, have both good cavity transmission ability, it synthesizes simple to operation, it can be applied in organic electroluminescence device as coating and/or hole transmission layer, it is serious light loss in organic electroluminescence device can effectively to be solved, luminous efficiency is low, the accumulation of device heat, device efficiency roll-offs seriously, service life shorter problem, its organic electroluminescence device has luminous efficiency high, the advantage of service life length.

Description

A kind of organic electroluminescence device aromatic amine compound and its organic electroluminescent Device
Technical field
The present invention relates to organic photoelectrical material technical field more particularly to a kind of organic electroluminescence device aromatic aminations Close object and its organic electroluminescence device.
Background technique
Organic electroluminescence device is by applying voltage at cathode, anode both ends, and Injection Current, electrons and holes are by each It after organic function layer, is combined in luminescent layer and forms exciton, exciton returns to stable ground state to radioluminescence.By more than 30 years Development, organic electroluminescence device efficiency have obtained biggish promotion, and because its with self-luminous, visual angle is wide, all solidstate, complete Coloured silkization, reaction speed are fast, high brightness, low driving voltage, thickness is thin, light weight, can make the features such as large scale and curved panel, Organic electroluminescence device has obtained more and more applications in monitor market, becomes current most potential Display panel Technology.
Common are organic electroluminescence devices is on a glass substrate using ITO as the device of anode, and light emission side is Bright glass lined bottom, so become bottom emitting device, but this device architecture is in industrial application, such as active matrix driving organic electroluminescence When luminescence display, it will display device pixel-driving circuit occur and show the problem of light-emitting area is vied each other, lead to device Aperture opening ratio be restricted.And the light of top emitting device is projected from cathode side, and pixel-driving circuit etc. is limited in luminescent device In the following, to solve the problems, such as that pixel-driving circuit and display area are vied each other, to substantially increase the opening of device The display screen of rate, top emitting device production also has many advantages, such as that high resolution, information content are high, this all makes top emitting device close Concern over year by industry and academia, and become a research hotspot.
But top emitting device is also by the limitation of self structure, due to using total reflection anode and semi-transparent gold in its structure Belong to cathode, when the light of sending at an angle from organic layer to cathode when, due to the difference of thin-film refractive index, some light Full transmitting occurs, the light of only fraction is utilized, and the output rating for causing device light reduces, and excessive energy is in device inside Accumulation is finally dissipated in the form of heat, to generate a series of adverse effects, the stability of material in device is caused to decline, The transmission performance for changing carrier eventually leads to device efficiency decaying seriously, and device lifetime reduces.Further, since inside OLED The organic material and high activity metal cathode used is more sensitive to water, the oxygen in environment, once having water, oxygen invasion, works as OLED When energization, non-luminous stain will be presented in the position to weather, over time, stain can slowly become larger, a step Step compression light emitting region, causes the decline of device brightness and efficiency, top radiation organic EL part at this stage by Increase organic material coating in semitransparent cathode to optimize top emitting device structure.
The organic material that coating generally uses at this stage is CBP, Alq3, CBP and Alq3Refraction in visible-range Rate is 1.7~2.0, although can play the role of certain raising device light emitting efficiency, refracting power effects are general, and Alq3There is certain absorption in blue wave band, the luminous efficiency and excitation purity of device blue light can be reduced.
With social demand, the requirement of industrialized production, the direction of the following organic electroluminescence device be develop high efficiency, High brightness, the long-life, low cost white light parts and full color display device, how to effectively improve the luminous efficiency of device, prolong Long life becomes organic electroluminescent urgent problem to be solved.
Summary of the invention
The object of the present invention is to provide a kind of organic electroluminescence device aromatic amine compound and its organic electroluminescents Device, organic electroluminescence device provided by the invention aromatic amine compound refractive index height, good film-forming property, thermal stability be good, It is simple to operation to have both good cavity transmission ability, synthetic method, by organic electroluminescence device virtue of the present invention Fragrant amine compounds are applied to be used as coating and/or hole transmission layer in organic electroluminescence device, can effectively improve device Luminous efficiency extends the service life of device.
The present invention provides a kind of organic electroluminescence device aromatic amine compound, general formula of molecular structure such as chemical formulas Shown in I:
Wherein, L is in substituted or unsubstituted C6~C30 arlydene, substituted or unsubstituted C3~C30 inferior heteroaryl Any one；R1、R2、R3、R4Independently selected from deuterium, the alkyl of C1~C10, C6~C30 aryl；Ar is selected from C1~C10's Alkyl, substituted or unsubstituted C6~C30 aryl, any one in substituted or unsubstituted C3~C30 heteroaryl；R5It is selected from Deuterium, the alkyl of C1~C10, substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C6~C30 aryl amine, replace or Any one in unsubstituted C3~C30 heteroaryl；A, b, c, d, e independently selected from 0 to 5 integer, when a, b, c, d, e take When value is greater than 1, multiple R1It can be independently selected from different groups, multiple R2It can be independently selected from different groups, multiple R3It can be only On the spot it is selected from different groups, multiple R4It can be independently selected from different groups, multiple R5Can independently selected from different groups, Multiple R1Between, multiple R2Between, multiple R3Between, multiple R4Between, multiple R5Between can be independently connected cyclization.
Preferably, L be selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthryl, Substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spiral shell Any one in fluorenyl, substituted or unsubstituted carbazyl.
Preferably, R1、R2、R3、R4Independently selected from deuterium, methyl, ethyl, isopropyl, tert-butyl, sec-butyl, phenyl, connection Phenyl, naphthalene, anthryl, phenanthryl, fluorenyl, it is Spirofluorene-based in any one, plurality of R1Between, multiple R2Between, multiple R3It Between, multiple R4Between can be independently connected cyclization.
Further preferably, any one of L in group as follows:
Further preferably, Ar is selected from substituted or unsubstituted following group: phenyl, naphthalene, anthryl, phenanthryl, triphenylene, pyrene Base, base, acridinyl, fluorenyl, Spirofluorene-based, carbazyl, furyl, thienyl, benzofuranyl, benzothienyl, dibenzo Furyl, dibenzothiophene, pyridyl group, pyrimidine radicals, triazine radical, quinolyl, isoquinolyl, pyridazinyl, pyrazinyl, quinoxaline Base, quinazolyl, indyl, azepine carbazyl, phenoxazine base, phenoxazine thiophene base, phenothiazinyl, imidazole radicals, benzimidazolyl, naphthalene And any one in imidazoles, phenanthro- imidazoles, pyrene and imidazole radicals.
Further preferably, R5Selected from deuterium, methyl, ethyl, isopropyl, tert-butyl, sec-butyl, substituted or unsubstituted following base Group: phenyl, naphthalene, anthryl, phenanthryl, acridinyl, fluorenyl, Spirofluorene-based, carbazyl, furyl, thienyl, benzofuranyl, benzene Bithiophene base, dibenzofuran group, dibenzothiophene, pyridyl group, pyrimidine radicals, triazine radical, quinolyl, isoquinolyl, pyridazine Base, pyrazinyl, quinoxalinyl, quinazolyl, indyl, azepine carbazyl, phenoxazine base, phenoxazine thiophene base, phenothiazinyl, imidazoles Base, benzimidazolyl, any one in diphenyl amido, multiple R5Between can connect cyclization.
Most preferably, organic electroluminescence device of the present invention is selected from chemical structure as follows with aromatic amine compound In any one:
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device successively includes sun Pole, the first organic matter layer, cathode, and/or the second organic matter layer, the second organic matter layer are located at cathode outer side, and described first has Contain organic electroluminescence device aromatic amine compound of the present invention in machine nitride layer and/or the second organic matter layer.
Preferably, the second organic matter layer of the present invention includes coating, is contained in coating of the present invention any Kind organic electroluminescence device aromatic amine compound.
Preferably, the first organic matter layer of the present invention includes hole transmission layer, contains institute of the present invention in hole transmission layer Any organic electroluminescence device aromatic amine compound stated.
Beneficial effects of the present invention:
The present invention provides a kind of organic electroluminescence device aromatic amine compound and its organic electroluminescence device.This hair Bright two substituted or unsubstituted 3,5- diphenyl benzene groups of ipsilateral connection in aromatic amine main structure, to obtain the present invention The organic electroluminescence device aromatic amine compound.
Fragrant amine structure itself is connected due to there is the nitrogen-atoms containing lone pair electrons, nitrogen-atoms by conjugated structure, Electronics on nitrogen-atoms occur under the action of an external electric field great-jump-forward transmitting, molecule thus generate hole, to realize the anti-of hole To transmitting, fragrant amine structure of the invention has good cavity transmission ability；3,5- diphenyl benzene group and virtue of the invention Fragrant amine structure is connected, and forms a multichained construction, 3 and 5 phenyl can form the delivering path in hole, to obtain Higher hole transport efficiency.
Organic electroluminescence device aromatic amine compound of the present invention is in the ipsilateral connection two of aromatic amine main structure A 3,5- diphenyl benzene group, 3,5- diphenyl benzene groups are non-co-planar group, and which increase Organic Electricities of the present invention The complexity of electroluminescence device aromatic amine compound geometric configuration forms the biggish dendritic morphology of steric configuration, reduces point The coplanarity of son, is easy to form a film.
The molecular weight of organic electroluminescence device aromatic amine compound of the present invention is larger, makes it have higher Glass transition temperature is not easy to crystallize, good thermal stability.
Organic electroluminescence device aromatic amine compound of the present invention connects two in aromatic amine main structure and takes Generation or unsubstituted 3,5- diphenyl benzene group effectively increase material in the application mostly without heteroatomic stable group Stability.
Organic electroluminescence device of the present invention has 1.8~2.1 high refractive index with aromatic amine compound, can have Effect reduces the full transmitting of light, reduces the light loss of device, improves the luminous efficiency of device.
Organic electroluminescence device aromatic amine compound refractive index of the present invention is high, it is good to be easy to film forming, stability, And there is good cavity transmission ability, it can be applied to be used as coating and/or hole transmission layer in organic electroluminescence device, The total reflection that light can be effectively reduced improves the delivery efficiency of light, and improves hole migration efficiency, to solve conventional organic electroluminescence That luminescent device light loss is serious, luminous efficiency is low, the accumulation of device heat, device efficiency roll-off is serious, device lifetime lower asks Topic.Had using organic electroluminescence device prepared by organic electroluminescence device of the present invention aromatic amine compound good Luminous efficiency and the service life performance.
Organic electroluminescence device preparation aromatic amine compound of the present invention is simple, and raw material is easy to get, Neng Gouman Foot industrialization demand.
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.
Alkyl of the present invention refers to alkyl made of minusing a hydrogen atom in alkane molecule, can be straight chain alkane Base, branched alkyl, naphthenic base, example may include methyl, ethyl, propyl, isopropyl, normal-butyl, isobutyl group, sec-butyl, tertiary fourth Base, amyl, isopentyl, cyclopenta, cyclohexyl 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 be the heteroaromatic being made of carbon and hetero atom core carbon on remove a hydrogen atom, be left The general name of univalent perssad, the hetero atom include but is not limited to oxygen, sulphur, nitrogen-atoms, and the heteroaryl can be bicyclic heteroaryl Or fused ring heteroaryl, embodiment may include carbazyl, acridinyl, benzothienyl, benzofuranyl, dibenzofuran group, two Benzothienyl, carbazyl etc., but not limited to this.
Aryl amine of the present invention refers to the amido with armaticity substituent, i.e.-NH2,-NH- or nitrogen-containing group connection Onto aromatic hydrocarbon.
The present invention provides a kind of organic electroluminescence device aromatic amine compound, general formula of molecular structure such as chemical formulas Shown in I:
L appointing in substituted or unsubstituted C6~C30 arlydene, substituted or unsubstituted C3~C30 inferior heteroaryl It anticipates one kind；R1、R2、R3、R4Independently selected from deuterium, the alkyl of C1~C10, C6~C30 aryl；Ar is selected from the alkane of C1~C10 Base, substituted or unsubstituted C6~C30 aryl, any one in substituted or unsubstituted C3~C30 heteroaryl；R5It is selected from Deuterium, the alkyl of C1~C10, substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C6~C30 aryl amine, replace or Any one in unsubstituted C3~C30 heteroaryl；A, b, c, d, e independently selected from 0 to 5 integer, when a, b, c, d, e take When value is greater than 1, multiple R1It can be independently selected from different groups, multiple R2It can be independently selected from different groups, multiple R3It can be only On the spot it is selected from different groups, multiple R4It can be independently selected from different groups, multiple R5Can independently selected from different groups, Multiple R1Between, multiple R2Between, multiple R3Between, multiple R4Between, multiple R5Between can be independently connected cyclization.
According to the present invention, the substituted aryl, substituted aryl amine, substituted arlydene, replaces substituted heteroaryl Inferior heteroaryl, wherein the substituent group independently selected from deuterium, cyano, halogen, C1~C10 alkyl, C6~C24 aryl, C6~ C24 aryl amine or C3~C24 heteroaryl, preferably deuterium, methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl, naphthalene, biphenyl Base, phenanthryl, anthryl, triphenylene, carbazyl, furyl, thienyl, benzofuranyl, benzothienyl, dibenzofurans Base, dibenzothiophene, acridinyl, phenoxazine base, phenothiazinyl, 9,9-dimethylacridan base, fluorenyl, 9,9- dimethyl fluorene Base, pyridyl group, pyrimidine radicals, triazine radical, any one in diphenyl amido.
Preferably, L be selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthryl, Substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spiral shell Any one in fluorenyl, substituted or unsubstituted carbazyl.
Preferably, R1、R2、R3、R4Independently selected from deuterium, methyl, ethyl, isopropyl, tert-butyl, sec-butyl, phenyl, connection Phenyl, naphthalene, anthryl, phenanthryl, fluorenyl, it is Spirofluorene-based in any one, plurality of R1Between, multiple R2Between, multiple R3It Between, multiple R4Between can be independently connected cyclization.
Further preferably, any one of L in group as follows:
Further preferably, Ar is selected from substituted or unsubstituted following group: phenyl, naphthalene, anthryl, phenanthryl, triphenylene, pyrene Base, base, acridinyl, fluorenyl, Spirofluorene-based, carbazyl, furyl, thienyl, benzofuranyl, benzothienyl, dibenzo Furyl, dibenzothiophene, pyridyl group, pyrimidine radicals, triazine radical, quinolyl, isoquinolyl, pyridazinyl, pyrazinyl, quinoxaline Base, quinazolyl, indyl, azepine carbazyl, phenoxazine base, phenoxazine thiophene base, phenothiazinyl, imidazole radicals, benzimidazolyl, naphthalene And any one in imidazoles, phenanthro- imidazoles, pyrene and imidazole radicals.
Further preferably, R5Selected from deuterium, methyl, ethyl, isopropyl, tert-butyl, sec-butyl, substituted or unsubstituted following base Group: phenyl, naphthalene, anthryl, phenanthryl, acridinyl, fluorenyl, Spirofluorene-based, carbazyl, furyl, thienyl, benzofuranyl, benzene Bithiophene base, dibenzofuran group, dibenzothiophene, pyridyl group, pyrimidine radicals, triazine radical, quinolyl, isoquinolyl, pyridazine Base, pyrazinyl, quinoxalinyl, quinazolyl, indyl, azepine carbazyl, phenoxazine base, phenoxazine thiophene base, phenothiazinyl, imidazoles Base, benzimidazolyl, any one in diphenyl amido, multiple R5Between can connect cyclization.
Most preferably, as an example, it is not particularly limited, a kind of organic electroluminescence device aromatic amine of the present invention Any one of compound in chemical structure as follows:
Most preferably, 0 e, it is further preferred that a, b, c, d, e are 0.
The present invention reacts to obtain organic electroluminescent of the present invention by a series of Suzuki reaction and Buchwald Device aromatic amine compound, synthetic route are as follows:
1, raw material r-1, r-2, with Pd2(dba)3、P(t-Bu)3For catalyst, NaOBu-t is alkali, obtains intermediate I -1；
2, raw material r-3, r-4, with Pd2(dba)3、P(t-Bu)3For catalyst, NaOBu-t is alkali, obtains intermediate I -2；
3, raw material r-5, intermediate I -1, with Pd2(dba)3、P(t-Bu)3For catalyst, NaOBu-t is alkali, obtains centre Body I -3；
4, intermediate I -3, I -2, with Pd2(dba)3、P(t-Bu)3For catalyst, NaOBu-t is alkali, obtains chemical compounds I.
The present invention limitation not special to above-mentioned reaction be using popular response well-known to those skilled in the art Can, the preparation method is simple, easily operated.
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device successively include anode, First organic matter layer, cathode, and/or the second organic matter layer, the second organic matter layer are located at cathode outer side, first organic matter Contain organic electroluminescence device aromatic amine compound of the present invention in layer and/or the second organic matter layer.
Preferably, second organic matter layer includes coating, is contained in coating of the present invention any organic Electroluminescent device aromatic amine compound, coating of the present invention can be one layer of structure, be also possible to two layers and Two layers or more structure.Any one layer in coating contains organic electroluminescence device aromatic amine chemical combination of the present invention Object.
First organic matter layer of the present invention is selected from hole injection layer, hole transmission layer, luminescent layer (light emitting host doping Object form or single substance form are as luminescent layer), hole blocking layer, electron transfer layer, at least one in electron injecting layer Kind.
Preferably, first organic matter layer includes hole transmission layer, contains of the present invention in hole transmission layer A kind of organic electroluminescence device aromatic amine compound.
Hole transmission layer can be single layer structure, be also possible to include the first hole transmission layer and the second hole transmission layer Double-layer structure, the second hole transmission layer is close to luminescent layer.Organic electroluminescence device aromatic amine compound of the present invention can To do the hole transmission layer of single layer, the first hole transmission layer of double-layer structure hole transmission layer can also be done.
Its structure of organic electroluminescence device of the present invention is preferred are as follows: substrate/anode/hole injection layer/hole passes Defeated layer/luminescent layer/electron transfer layer/electron injecting layer/cathode/coating.However, the structure of organic electroluminescence device is unlimited In this.Organic electroluminescence device of the present invention can carry out selection and group according to the characteristic of device parameter requirements and material It closes, part organic layer can also be added or omitted.
Organic electroluminescence device structure of the present invention is further preferably are as follows: ITO or ITO-Ag-ITO are as anode；NPD: F4-TCNQ (97:3) is used as hole injection layer；Organic electroluminescence device of the present invention is made with aromatic amine compound or NPD is Hole transmission layer；BH/BD is as luminescent layer substance；Alq3As electron transfer layer；LiF is used as electron injecting layer；Mg:Ag or Al As cathode, organic electroluminescence device of the present invention uses aromatic amine compound as coating.
Organic electroluminescence device of the present invention is used as coating and/or hole transmission layer with aromatic amine compound, To manufacture the organic electroluminescence device of construction same as below:
ITO-Ag-ITO/NPD:F4-TCNQ (97:3)/NPD/BH:BD/Alq3/ LiF/Mg:Ag/ is of the present invention to be had Organic electroluminescence devices aromatic amine compound；
ITO/NPD:F4-TCNQ (97:3)/organic electroluminescence device of the present invention aromatic amine compound/BH: BD/Alq3/LiF/Al；
ITO-Ag-ITO/NPD:F4-TCNQ (97:3)/organic electroluminescence device of the present invention aromatic amine chemical combination Object/BH:BD/Alq3/ LiF/Mg:Ag/NPD or TBDB or Alq3CBP or organic electroluminescence device of the present invention virtue Fragrant amine compounds.
Organic electroluminescence device of the present invention can be widely applied to Display panel, lighting source, flexibility OLED, electronics The fields such as paper, Organophotoreceptor or Organic Thin Film Transistors, direction board, signal lamp.
The synthesis of [embodiment 1] compound 4
Step1: being added 1,1':3', 1 " terphenyl -5'- amine (2.45g, 10mmol), 5'- bromo- 1,1':3' in reactor, 1 " terphenyl (3.09g, 10mmol), Pd2(dba)3(0.21g, 0.25mmol), P (t-Bu)3(0.18g, 0.84mmol), NaOt-Bu (2.8g, 25mmol), toluene solution 100mL react for 24 hours under the conditions of 100 DEG C, are extracted after reaction with ether and water Take organic phase, organic layer MgSO4It is dry, condensed organic, cross column chromatography, be recrystallized to give intermediate 4-1 (3.88g, 82%).
Step2: aniline (0.93g, 10mmol), 3- bromo biphenyl (2.33g, 10mmol), Pd are added in reactor2(dba)3 (0.21g, 0.25mmol), P (t-Bu)3(0.18g, 0.84mmol), NaOt-Bu (2.8g, 25mmol), toluene solution 100mL, It is reacted under the conditions of 100 DEG C for 24 hours, extracts organic phase, organic layer MgSO with ether and water after reaction4It is dry, it is concentrated organic Object crosses column chromatography, is recrystallized to give intermediate 4-2 (2.09g, 85%).
Step3: intermediate 4-1 (4.74g, 10mmol) is added in reactor, to bromo-iodobenzene (2.83g, 10mmol), Pd2 (dba)3(0.21g, 0.25mmol), P (t-Bu)3(0.18g, 0.84mmol), NaOt-Bu (2.8g, 25mmol), toluene solution 100mL reacts for 24 hours under the conditions of 100 DEG C, extracts organic phase, organic layer MgSO with ether and water after reaction4It is dry, it is dense Contracting organic matter crosses column chromatography, is recrystallized to give intermediate 4-3 (5.03g, 80%).
Step4: intermediate 4-3 (6.29g, 10mmol), 4-2 (2.45g, 10mmol), Pd are added in reactor2(dba)3 (0.21g, 0.25mmol), P (t-Bu)3(0.18g, 0.84mmol), NaOt-Bu (2.8g, 25mmol), toluene solution 100mL, It is reacted under the conditions of 100 DEG C for 24 hours, extracts organic phase, organic layer MgSO with ether and water after reaction4It is dry, it is concentrated organic Object crosses column chromatography, is recrystallized to give compound 4 (6.34g, 80%).
The synthesis of [embodiment 2] compound 19
Compound 19 (6.62g, 75%) is obtained according to the synthetic method of 1 compound 4 of embodiment.
The synthesis of [embodiment 3] compound 24
Compound 24 (6.90g, 78%) is obtained according to the synthetic method of 1 compound 4 of embodiment.
The synthesis of [embodiment 4] compound 38
Compound 38 (6.95g, 80%) is obtained according to the synthetic method of 1 compound 4 of embodiment.
The synthesis of [embodiment 5] compound 41
Compound 41 (6.34g, 80%) is obtained according to the synthetic method of 1 compound 4 of embodiment.
The synthesis of [embodiment 6] compound 55
Compound 55 (7.47g, 78%) is obtained according to the synthetic method of 1 compound 4 of embodiment.
The synthesis of [embodiment 7] compound 66
Compound 66 (6.82g, 75%) is obtained according to the synthetic method of 1 compound 4 of embodiment.
The synthesis of [embodiment 8] compound 103
Compound 103 (6.90g, 74%) is obtained according to the synthetic method of 1 compound 4 of embodiment.
The synthesis of [embodiment 9] compound 129
Compound 129 (7.42g, 78%) is obtained according to the synthetic method of 1 compound 4 of embodiment.
The organic electroluminescence device of synthesis of the embodiment of the present invention is as shown in table 1 with aromatic amine compound FD-MS value.
[table 1]
Embodiment FD-MS
Embodiment 1 M/z=792.34 (C60H44N2=792.35)
Embodiment 2 M/z=882.37 (C66H46N2O=882.36)
Embodiment 3 M/z=883.41 (C66H49N3=883.39)
Embodiment 4 M/z=868.40 (C66H48N2=868.38)
Embodiment 5 M/z=792.34 (C60H44N2=792.35)
Embodiment 6 M/z=957.43 (C72H51N3=957.41)
Embodiment 7 M/z=908.41 (C67H48N4=908.39)
Embodiment 8 M/z=931.42 (C70H49N3=931.39)
Embodiment 9 M/z=950.48 (C72H58N2=950.46)
The results are shown in Table 2 for the compound refraction index test of 1-9 of embodiment of the present invention synthesis:
[table 2]
Embodiment Compound Refractive index
Embodiment 1 4 1.90
Embodiment 2 19 1.92
Embodiment 3 24 1.93
Embodiment 4 38 1.97
Embodiment 5 41 1.95
Embodiment 6 55 2.03
Embodiment 7 66 2.01
Embodiment 8 103 1.98
Embodiment 9 129 1.88
[comparative example 1] device prepares embodiment:
ITO-Ag-ITO glass substrate is placed in distilled water and is cleaned 2 times, ultrasonic washing 30 minutes, distilled water cleaning was tied Shu Hou, ultrasonic washing is later dry in order for isopropanol, acetone, methanol equal solvent, is transferred in plasma washing machine, will Aforesaid substrate washs 5 minutes, is sent in evaporator.
Successively be deposited in the ITO-Ag-ITO transparent electrode having had been prepared for cave implanted layer NPD:F4-TCNQ (97:3)/ 50nm, hole transmission layer NPD/80nm, vapor deposition 3% mixing of luminescent layer BH:BD/20nm, electron transfer layer Alq3/ 30nm, electronics Implanted layer LiF/1nm, cathode Mg/Ag (10:1)/15nm, coating TBDB/60nm.
[embodiment 10] device prepares embodiment:
ITO-Ag-ITO glass substrate is placed in distilled water and is cleaned 2 times, ultrasonic washing 30 minutes, distilled water cleaning was tied Shu Hou, ultrasonic washing is later dry in order for isopropanol, acetone, methanol equal solvent, is transferred in plasma washing machine, will Aforesaid substrate washs 5 minutes, is sent in evaporator.
Successively be deposited in the ITO-Ag-ITO transparent electrode having had been prepared for cave implanted layer NPD:F4-TCNQ (97:3)/ 50nm, hole transmission layer NPD/80nm, vapor deposition 3% mixing of luminescent layer BH:BD/20nm, electron transfer layer Alq3/ 30nm, electronics Implanted layer LiF/1nm, cathode Mg/Ag (10:1)/15nm, coating compound 4/60nm.
[embodiment 11] device prepares embodiment:
The compound 4 of the coating of embodiment 10 is changed to the compound 19 of embodiment 2.
[embodiment 12] device prepares embodiment:
The compound 4 of the coating of embodiment 10 is changed to the compound 24 of embodiment 3.
[embodiment 13] device prepares embodiment:
The compound 4 of the coating of embodiment 10 is changed to the compound 38 of embodiment 4.
[embodiment 14] device prepares embodiment:
The compound 4 of the coating of embodiment 10 is changed to the compound 41 of embodiment 5.
[embodiment 15] device prepares embodiment:
The compound 4 of the coating of embodiment 10 is changed to the compound 55 of embodiment 6.
[embodiment 16] device prepares embodiment:
The compound 4 of the coating of embodiment 10 is changed to the compound 66 of embodiment 7.
[embodiment 17] device prepares embodiment:
The compound 4 of the coating of embodiment 10 is changed to the compound 103 of embodiment 8.
[embodiment 18] device prepares embodiment:
The compound 1 of the coating of embodiment 10 is changed to the compound 129 of embodiment 9.
[embodiment 19] device prepares embodiment:
ITO-Ag-ITO glass substrate is placed in distilled water and is cleaned 2 times, ultrasonic washing 30 minutes, distilled water cleaning was tied Shu Hou, ultrasonic washing is later dry in order for isopropanol, acetone, methanol equal solvent, is transferred in plasma washing machine, will Aforesaid substrate washs 5 minutes, is sent in evaporator.
Successively be deposited in the ITO-Ag-ITO transparent electrode having had been prepared for cave implanted layer NPD:F4-TCNQ (97:3)/ 50nm, hole transmission layer compound 19/80nm, vapor deposition 3% mixing of luminescent layer BH:BD/20nm, electron transfer layer Alq3/ 30nm, electron injecting layer LiF/1nm, cathode Mg/Ag (10:1)/15nm, coating compound 24/60nm.
[embodiment 20] device prepares embodiment:
The compound 19 of the hole transmission layer of embodiment 19 is changed to the compound 24 of embodiment 3.
[embodiment 21] device prepares embodiment:
The compound 19 of the hole transmission layer of embodiment 19 is changed to the compound 55 of embodiment 6.
[embodiment 22] device prepares embodiment:
The compound 19 of the hole transmission layer of embodiment 19 is changed to the compound 66 of embodiment 7.
[embodiment 23] device prepares embodiment:
The compound 19 of the hole transmission layer of embodiment 19 is changed to the compound 103 of embodiment 8.
The characteristics of luminescence test result such as table 3 of luminescent device prepared by 10-23 of the embodiment of the present invention and comparative example 1 It is shown:
[table 3]
The above result shows that organic electroluminescence device of the present invention is applied to Organic Electricity with aromatic amine compound In electroluminescence device, especially as coating and/or hole transmission layer, organic electroluminescence device has luminous efficiency The advantages of height, long service life, organic electroluminescence device of the invention is organic hair of good performance with aromatic amine compound Luminescent material.
It should be pointed out that the present invention is particularly described with individual embodiments, but before not departing from the principle of the invention It puts, ordinary skill people can carry out the improvement on various forms or details to the present invention, these improvement also fall into this hair In bright protection scope.

Claims (10)

1. a kind of organic electroluminescence device aromatic amine compound, which is characterized in that its general formula of molecular structure such as I institute of chemical formula Show:
Wherein, L appointing in substituted or unsubstituted C6~C30 arlydene, substituted or unsubstituted C3~C30 inferior heteroaryl It anticipates one kind；R1、R2、R3、R4Independently selected from deuterium, the alkyl of C1~C10, C6~C30 aryl；Ar is selected from the alkane of C1~C10 Base, substituted or unsubstituted C6~C30 aryl, any one in substituted or unsubstituted C3~C30 heteroaryl；R5It is selected from Deuterium, the alkyl of C1~C10, substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C6~C30 aryl amine, replace or Any one in unsubstituted C3~C30 heteroaryl；A, b, c, d, e independently selected from 0 to 5 integer, when a, b, c, d, e take When value is greater than 1, multiple R1It can be independently selected from different groups, multiple R2It can be independently selected from different groups, multiple R3It can be only On the spot it is selected from different groups, multiple R4It can be independently selected from different groups, multiple R5Can independently selected from different groups, Multiple R1Between, multiple R2Between, multiple R3Between, multiple R4Between, multiple R5Between can be independently connected cyclization.
2. a kind of organic electroluminescence device aromatic amine compound according to claim 1, which is characterized in that L is selected from Substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, It is substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted Spirofluorene-based, substituted or unsubstituted Any one in carbazyl.
3. a kind of organic electroluminescence device aromatic amine compound according to claim 1, which is characterized in that R1、R2、 R3、R4Independently selected from deuterium, methyl, ethyl, isopropyl, tert-butyl, sec-butyl, phenyl, xenyl, naphthalene, anthryl, phenanthryl, fluorenes Base, it is Spirofluorene-based in any one, plurality of R1Between, multiple R2Between, multiple R3Between, multiple R4Between can independently connect It is connected into ring.
4. a kind of organic electroluminescence device aromatic amine compound according to claim 1, which is characterized in that L is selected from Any one in group as follows:
5. a kind of organic electroluminescence device aromatic amine compound according to claim 1, which is characterized in that Ar is selected from Substituted or unsubstituted following group: phenyl, naphthalene, anthryl, phenanthryl, triphenylene, pyrenyl, base, acridinyl, fluorenyl, spiral shell Fluorenyl, carbazyl, furyl, thienyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophene, pyrrole Piperidinyl, pyrimidine radicals, triazine radical, quinolyl, isoquinolyl, pyridazinyl, pyrazinyl, quinoxalinyl, quinazolyl, indyl, nitrogen Miscellaneous carbazyl, phenoxazine base, phenoxazine thiophene base, phenothiazinyl, imidazole radicals, benzimidazolyl, naphtho- imidazoles, phenanthro- imidazoles, pyrene are simultaneously Any one in imidazole radicals.
6. a kind of organic electroluminescence device aromatic amine compound according to claim 1, which is characterized in that R5It is selected from Deuterium, methyl, ethyl, isopropyl, tert-butyl, sec-butyl, substituted or unsubstituted following group: phenyl, naphthalene, anthryl, phenanthryl, Acridinyl, fluorenyl, Spirofluorene-based, carbazyl, furyl, thienyl, benzofuranyl, benzothienyl, dibenzofuran group, two Benzothienyl, pyridyl group, pyrimidine radicals, triazine radical, quinolyl, isoquinolyl, pyridazinyl, pyrazinyl, quinoxalinyl, quinazoline Base, indyl, azepine carbazyl, phenoxazine base, phenoxazine thiophene base, phenothiazinyl, imidazole radicals, benzimidazolyl, diphenyl amido In any one, multiple R5Between can connect cyclization.
7. a kind of organic electroluminescence device aromatic amine compound according to claim 1, which is characterized in that described to have Any one of organic electroluminescence devices aromatic amine compound in chemical structure as follows:
8. a kind of organic electroluminescence device, which is characterized in that the organic electroluminescence device successively includes anode, first has Machine nitride layer, cathode, and/or the second organic matter layer, the second organic matter layer are located at cathode outer side, first organic matter layer and/ Or second contain the described in any item organic electroluminescence device aromatic amine compounds of claim 1~7 in organic matter layer.
9. a kind of organic electroluminescence device according to claim 8, which is characterized in that second organic matter layer Including coating, claim 1~7 described in any item organic electroluminescence devices aromatic amine chemical combination is contained in coating Object.
10. a kind of organic electroluminescence device according to claim 8, which is characterized in that first organic matter Layer includes hole transmission layer, contains the described in any item organic electroluminescence device virtues of claim 1~7 in hole transmission layer Fragrant amine compounds.
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110838561A (en) * 2019-11-19 2020-02-25 长春海谱润斯科技有限公司 Organic electroluminescent device
JP2021014444A (en) * 2019-07-12 2021-02-12 長春海譜潤斯科技有限公司 Amine derivative and organic electroluminescent element thereof
CN113461547A (en) * 2020-03-31 2021-10-01 江苏三月科技股份有限公司 Diamine derivative for organic electroluminescent device
CN113620899A (en) * 2021-08-20 2021-11-09 上海钥熠电子科技有限公司 Aromatic amine compound and application thereof in organic electroluminescent display device

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2021014444A (en) * 2019-07-12 2021-02-12 長春海譜潤斯科技有限公司 Amine derivative and organic electroluminescent element thereof
US11725003B2 (en) 2019-07-12 2023-08-15 Changchun Hyperions Technology Co., Ltd Amine derivative and an organic electroluminescent device thereof
CN110838561A (en) * 2019-11-19 2020-02-25 长春海谱润斯科技有限公司 Organic electroluminescent device
CN110838561B (en) * 2019-11-19 2020-07-03 长春海谱润斯科技有限公司 Organic electroluminescent device
CN113461547A (en) * 2020-03-31 2021-10-01 江苏三月科技股份有限公司 Diamine derivative for organic electroluminescent device
CN113461547B (en) * 2020-03-31 2023-11-21 江苏三月科技股份有限公司 Diamine derivative for organic electroluminescent device
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