CN109400520A - A kind of benzidine compound and its organic electroluminescence device - Google Patents

A kind of benzidine compound and its organic electroluminescence device Download PDF

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Publication number
CN109400520A
CN109400520A CN201811422774.8A CN201811422774A CN109400520A CN 109400520 A CN109400520 A CN 109400520A CN 201811422774 A CN201811422774 A CN 201811422774A CN 109400520 A CN109400520 A CN 109400520A
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substituted
unsubstituted
compound
benzidine
layer
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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 benzidine compound and its organic electroluminescence device, is related to organic optoelectronic materials technology.The present invention connects carbazoles group and 3 in benzidine main structure, 5- diphenyl benzene group obtains a kind of benzidine compound, its refractive index is high, good film-forming property, thermal stability is good, with 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 benzidine compound and its organic electroluminescence device
Technical field
The present invention relates to organic photoelectrical material technical fields more particularly to a kind of benzidine compound and its organic electroluminescence to send out Optical 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 generate radioluminescence.More than 30 Year development, organic electroluminescence device efficiency obtained biggish promotion, and because its with self-luminous, visual angle is wide, Quan Gu Change, true color, reaction speed be fast, high brightness, low driving voltage, thickness are thin, light weight, can make large scale and curved panel etc. Feature, organic electroluminescence device have obtained more and more applications in monitor market, become current most potential face Plate display technology.
Theoretically, in the case where cathode or anode are transparent electrode, the light that luminescent layer issues can both be passed from anode It is multicast to device exterior, can also be from cathode transport to device exterior, according to the path that light is spread out of, organic electroluminescence device again may be used To be divided into bottom emitting organic electroluminescence device and top radiation organic EL part.
Bottom emitting organic electroluminescence device is on a glass substrate using ITO as the device of anode, and light emission side is Bright glass lined bottom, but this device architecture, in industrial application, in active matrix configuration, the light emitting path of device is organic Layer-anode-TFT- substrate, TFT are the mesh array switch for being deposited on substrate, and emergent light can be tied when traveling to TFT due to TFT Transmitting occurs for structure, scattering is blocked and can not travel to device exterior, so that the aperture opening ratio of device further decreases.And Top radiation organic EL part needs not move through substrate since light emission side is in cathode, so as to avoid opening in bottom emitting device The low problem of mouthful rate, so that device can achieve higher PPI, the pixel quantity of display screen unit area is more, picture it is thin Section will be abundanter, while colour vividness is also higher, this makes top emitting device in recent years by industry and the pass of academia Note, and become a research hotspot.
But top radiation organic EL part is also by the limitation of self structure, due to the presence of its metallic cathode, The loss of exterior light coupling efficiency is mainly caused by plasma primitive effect and waveguiding effect.Waveguiding effect is mainly due to more Total reflection between layer organic film, causes light to be limited in organic layer and is consumed, cause device efficiency to be greatly lowered, together When, light, which is limited in device inside, to be projected, and heat is eventually converted into, and cause the heat of device inside to gather, to cause A series of adverse effect such as influences the stability of organic material, changes the transmission performance of internal carrier, eventually leads to device Efficiency roll-off is serious, and device lifetime reduces serious.Further, since the organic material and high activity metal cathode that are used inside OLED It is more sensitive to water, the oxygen in environment, once there are water, oxygen invasion that will present not when OLED is powered in the position to weather Luminous stain, over time, stain can slowly become larger, and compress light emitting region step by step, cause device brightness, efficiency Decline and device service life reduction, therefore device architecture, evaporation coating technique, encapsulation technology be also influence device performance Key factor.
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 top radiation organic EL The luminous efficiency of device prolongs the service life as urgent problem to be solved.
Summary of the invention
It is provided by the invention the object of the present invention is to provide a kind of benzidine compound and its organic electroluminescence device Aniline compound refractive index height, good film-forming property, thermal stability are good, have good cavity transmission ability, synthetic method simply easy Benzidine compound of the present invention is applied to pass in organic electroluminescence device as coating and/or hole by operation Defeated layer can effectively improve the luminous efficiency of device, extend the service life of device.
It is any shown in general formula of molecular structure such as chemical formula I, II the present invention provides a kind of benzidine compound:
Wherein, Ar1、Ar2Independently selected from substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C30 Any one in aryl, substituted or unsubstituted C3~C30 heteroaryl；R1、R2、R3、R4Independently selected from H, deuterium, substitution or Unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C30 aryl, takes substituted or unsubstituted C1~C10 alkylene Generation or unsubstituted C6~C30 aryl amine, substituted or unsubstituted C6~C30 aralkyl, substituted or unsubstituted C6~C30 virtue Sulfenyl, substituted or unsubstituted C6~C30 aryloxy group, any one in substituted or unsubstituted C3~C30 heteroaryl, a, b, C, d independently selected from 0 to 5 integer, when independently value is greater than 1 by a, b, c, d, corresponding multiple R1It can be selected from different bases Group, corresponding multiple R2It can be selected from different groups, corresponding multiple R3It can be selected from different groups, corresponding multiple R4It is optional From different groups, multiple R1Between, multiple R2Between, multiple R3Between, multiple R4Between can be independently connected cyclization.
Preferably, the molecular structure of benzidine compound of the present invention is any shown in chemical formula III, IV:
Preferably, R1、R2、R3、R4It does not take independently selected from H, deuterium, substituted or unsubstituted C1~C10 alkyl, substitution or C6~C30 aryl in generation, substituted or unsubstituted C6~C30 aryl amine, appointing in substituted or unsubstituted C3~C30 heteroaryl It anticipates one kind.
Further preferably, R1、R2、R3、R4Independently selected from H, deuterium, methyl, ethyl, isopropyl, tert-butyl, sec-butyl, substitution or Unsubstituted following group: phenyl, naphthalene, anthryl, phenanthryl, acridinyl, fluorenyl, Spirofluorene-based, carbazyl, furyl, thienyl, Benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophene, pyridyl group, pyrimidine radicals, triazine radical, quinolyl, Isoquinolyl, pyridazinyl, pyrazinyl, quinoxalinyl, quinazolyl, indyl, azepine carbazyl, phenoxazine base, phenoxazine thiophene base, Phenothiazinyl, imidazole radicals, benzimidazolyl, any one in diphenyl amido.
Further preferably, Ar1、Ar2Independently selected from substituted or unsubstituted following group: phenyl, naphthalene, anthryl, phenanthryl, three Phenylene, pyrenyl, base, acridinyl, fluorenyl, Spirofluorene-based, carbazyl, furyl, thienyl, benzofuranyl, benzothiophene Base, dibenzofuran group, dibenzothiophene, pyridyl group, pyrimidine radicals, triazine radical, quinolyl, isoquinolyl, pyridazinyl, pyrazine Base, quinoxalinyl, quinazolyl, indyl, azepine carbazyl, phenoxazine base, phenoxazine thiophene base, phenothiazinyl, imidazole radicals, benzo Any one in imidazole radicals, naphtho- imidazoles, phenanthro- imidazoles, pyrene and imidazole radicals.
Most preferably, any one of benzidine compound of the present invention in chemical structure as follows:
It is further preferred that a, b, c, d are 0.
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 benzidine 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 benzidine 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 benzidine compound stated.
Beneficial effects of the present invention:
The present invention provides a kind of benzidine compound and its organic electroluminescence device.The present invention is in benzidine main structure Upper connection carbazoles group and 3,5- diphenyl benzene group, to obtain benzidine compound of the present invention.
Benzidine compound of the present invention has the high index of 1.8-2.1, can improve the saturating of cathode surface Rate is crossed, the full transmitting and waveguiding effect of light are effectively reduced.
Benzidine compound of the present invention connects carbazoles group and 3,5- diphenyl in benzidine main structure Phenyl group, 3,5- diphenyl benzene groups are non-co-planar group, and which increase benzidine compound geometry structures of the present invention The complexity of type forms the biggish dendritic morphology of steric configuration, reduces the coplanarity of molecule, be easy to form a film.
The molecular weight of benzidine compound of the present invention is larger, makes it have higher glass transition temperature, is not easy to tie Crystalline substance, good thermal stability.
Furthermore biphenyl amine structure, carbazoles group itself pass through due to there is the nitrogen-atoms containing lone pair electrons, nitrogen-atoms Conjugated structure be connected, the electronics on nitrogen-atoms occur under the action of an external electric field great-jump-forward transmitting, molecule thus generate hole, from And realize the back transfer in hole, benzidine compound of the present invention adds carbazoles group and 3,5- diphenyl phenyl Group, forms a multichained construction, is more favorable for the transmission in hole, to have good cavity transmission ability.
Benzidine compound refractive index of the present invention is high, is easy to form a film, and stability is good, and there is good hole to pass Movement Capabilities can be applied in organic electroluminescence device that being all-trans for light can be effectively reduced as coating and/or hole transmission layer It penetrates and waveguiding effect, improves hole migration efficiency, to solve that conventional organic electroluminescence device light loss is serious, luminous efficiency The problem that low, device heat gathers, device efficiency roll-offs seriously, device lifetime is lower.Using biphenyl amine compounds of the present invention There is the organic electroluminescence device of object preparation good luminous efficiency and service life to show.
Benzidine compound preparation method of the present invention is simple, and raw material is easy to get, and can satisfy 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.
It is any shown in general formula of molecular structure such as chemical formula I, II the present invention provides a kind of benzidine compound:
Wherein, Ar1、Ar2Independently selected from substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C30 Any one in aryl, substituted or unsubstituted C3~C30 heteroaryl；R1、R2、R3、R4Independently selected from H, deuterium, substitution or Unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C30 aryl, takes substituted or unsubstituted C1~C10 alkylene Generation or unsubstituted C6~C30 aryl amine, substituted or unsubstituted C6~C30 aralkyl, substituted or unsubstituted C6~C30 virtue Sulfenyl, substituted or unsubstituted C6~C30 aryloxy group, any one in substituted or unsubstituted C3~C30 heteroaryl, a, b, C, d independently selected from 0 to 5 integer, when independently value is greater than 1 by a, b, c, d, corresponding multiple R1It can be selected from different bases Group, corresponding multiple R2It can be selected from different groups, corresponding multiple R3It can be selected from different groups, corresponding multiple R4It is optional From different groups, multiple R1Between, multiple R2Between, multiple R3Between, multiple R4Between can be independently connected cyclization.
According to the present invention, the substituted alkyl, substituted aryl, substituted heteroaryl, substituted aryl amine, replace Aralkyl, substituted alkylene, substituted arylthio, substituted aryloxy group, wherein the substituent group is independently selected from deuterium, cyanogen Base, halogen, C1~C10 alkyl, C6~C24 aryl, C6~C24 aryl amine or C3~C24 heteroaryl, preferably deuterium, methyl, second Base, propyl, isopropyl, tert-butyl, phenyl, naphthalene, xenyl, phenanthryl, anthryl, triphenylene, carbazyl, furyl, thiophene Base, benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophene, acridinyl, phenoxazine base, phenothiazinyl, It is 9,9-dimethylacridan base, fluorenyl, 9,9- dimethyl fluorenyl, pyridyl group, pyrimidine radicals, triazine radical, any in diphenyl amido It is a kind of.
Preferably, the molecular structure of benzidine compound of the present invention is any shown in chemical formula III, IV:
Preferably, R1、R2、R3、R4It does not take independently selected from H, deuterium, substituted or unsubstituted C1~C10 alkyl, substitution or C6~C30 aryl in generation, substituted or unsubstituted C6~C30 aryl amine, appointing in substituted or unsubstituted C3~C30 heteroaryl It anticipates one kind.
Further preferably, R1、R2、R3、R4Independently selected from H, deuterium, methyl, ethyl, isopropyl, tert-butyl, sec-butyl, substitution or Unsubstituted following group: phenyl, naphthalene, anthryl, phenanthryl, acridinyl, fluorenyl, Spirofluorene-based, carbazyl, furyl, thienyl, Benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophene, pyridyl group, pyrimidine radicals, triazine radical, quinolyl, Isoquinolyl, pyridazinyl, pyrazinyl, quinoxalinyl, quinazolyl, indyl, azepine carbazyl, phenoxazine base, phenoxazine thiophene base, Phenothiazinyl, imidazole radicals, benzimidazolyl, any one in diphenyl amido.
Further preferably, Ar1、Ar2Independently selected from substituted or unsubstituted following group: phenyl, naphthalene, anthryl, phenanthryl, three Phenylene, pyrenyl, base, acridinyl, fluorenyl, Spirofluorene-based, carbazyl, furyl, thienyl, benzofuranyl, benzothiophene Base, dibenzofuran group, dibenzothiophene, pyridyl group, pyrimidine radicals, triazine radical, quinolyl, isoquinolyl, pyridazinyl, pyrazine Base, quinoxalinyl, quinazolyl, indyl, azepine carbazyl, phenoxazine base, phenoxazine thiophene base, phenothiazinyl, imidazole radicals, benzo Any one in imidazole radicals, naphtho- imidazoles, phenanthro- imidazoles, pyrene and imidazole radicals.
Most preferably, as an example, it is not particularly limited, a kind of benzidine compound of the present invention is selected from as follows Any one in chemical structure:
It is further preferred that a, b, c, d are 0.
The present invention reacts to obtain benzidine compound of the present invention by a series of Suzuki reaction and Buchwald I, synthetic route is as follows:
1, raw material a-1, a-2, with Pd2(dba)3、P(t-Bu)3For catalyst, NaOBu-t is alkali, obtains intermediate I -1；
2, raw material a-3, a-4, with Pd2(dba)3、P(t-Bu)3For catalyst, NaOBu-t is alkali, obtains intermediate I -2；
3, raw material a-5, intermediate I -2, with Pd2(dba)3、P(t-Bu)3For catalyst, NaOBu-t is alkali, obtains centre Body I -3；
4, intermediate I -3, I -1, with Pd2(dba)3、P(t-Bu)3For catalyst, NaOBu-t is alkali, obtains chemical compounds I.
The present invention reacts to obtain benzidine compound of the present invention by a series of Suzuki reaction and Buchwald II, synthetic route is as follows:
1, raw material b-1, b-2, with Pd2(dba)3、P(t-Bu)3For catalyst, NaOBu-t is alkali, obtains intermediate II -1；
2, raw material b-3, b-4, with Pd2(dba)3、P(t-Bu)3For catalyst, NaOBu-t is alkali, obtains intermediate II -2；
3, raw material b-5, intermediate II -2, with Pd2(dba)3、P(t-Bu)3For catalyst, NaOBu-t is alkali, obtains centre Body II -3；
4, intermediate II -3, II -1, with Pd2(dba)3、P(t-Bu)3For catalyst, NaOBu-t is alkali, obtains compound Ⅱ。
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 benzidine compound of the present invention in layer and/or the second organic matter layer.
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 benzidine compound.
Preferably, second organic matter layer includes coating, contains any biphenyl of the present invention in coating Amine compounds, coating of the present invention can be one layer of structure, be also possible to two layers and two layers or more structure.Coating In any one layer contain benzidine compound of the present invention.
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 benzidine 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.Any one layer in hole transmission layer contains biphenyl of the present invention Amine compounds.
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；Benzidine compound of the present invention is made or NPD is hole transmission layer；BH/BD makees For luminescent layer substance；Alq3As electron transfer layer；LiF is used as electron injecting layer；Al or Mg:Ag is used as cathode, institute of the present invention Benzidine compound is stated as coating.
Benzidine compound of the present invention is used as hole transmission layer, to manufacture the Organic Electricity of construction same as below Electroluminescence device:
ITO/NPD:F4-TCNQ (97:3)/benzidine compound/BH:BD/Alq of the present invention3/LiF/Al；
ITO-Ag-ITO/NPD:F4-TCNQ (97:3)/benzidine compound/BH:BD/Alq of the present invention3/LiF/ Mg:Ag/TBDB。
Benzidine compound of the present invention is used as coating, and the organic electroluminescence to manufacture construction same as below is sent out Optical device:
ITO-Ag-ITO/NPD:F4-TCNQ (97:3)/NPD/BH:BD/Alq3/ LiF/Mg:Ag/ is of the present invention Aniline compound.
Benzidine compound of the present invention is used as hole transmission layer and coating, to have manufactured construction same as below Organic electroluminescence device:
ITO-Ag-ITO/NPD:F4-TCNQ (97:3)/benzidine compound/BH:BD/Alq of the present invention3/LiF/ Mg:Ag/ benzidine compound of the present invention.
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 2
Step1: aniline (0.93g, 10mmol), 4- bromobiphenyl (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 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 2-1 (2.09g, 85%).
Step2: 1,1':3', 1 " terphenyl -5'- amine (2.45,10mmol), 3- bromine-N-phenylcarbazole are added in reactor (3.22g, 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, organic with ether and water extraction after reaction Phase, organic layer MgSO4Dry, condensed organic crosses column chromatography, is recrystallized to give intermediate 2-2 (3.80g, 78%).
Step3: in reactor be added intermediate 2-2 (4.87g, 10mmol), the iodo- biphenyl of the bromo- 4- of 4- (3.59g, 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 with ether and water after reaction, organic Layer uses MgSO4Dry, condensed organic crosses column chromatography, is recrystallized to give intermediate 2-3 (5.74g, 80%).
Step4: intermediate 2-3 (7.17g, 10mmol), 2-1 (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 2 (6.88g, 78%).
The synthesis of [embodiment 2] compound 18
Compound 18 (7.01g, 76%) is obtained according to the synthetic method of 1 compound 2 of embodiment.
The synthesis of [embodiment 3] compound 40
Compound 40 (7.96g, 77%) is obtained according to the synthetic method of 1 compound 2 of embodiment.
The synthesis of [embodiment 4] compound 56
Compound 56 (7.10g, 75%) is obtained according to the synthetic method of 1 compound 2 of embodiment.
The synthesis of [embodiment 5] compound 97
Compound 97 (6.68g, 78%) is obtained according to the synthetic method of 1 compound 2 of embodiment.
The synthesis of [embodiment 6] compound 117
Compound 117 (7.69g, 79%) is obtained according to the synthetic method of 1 compound 2 of embodiment.
The synthesis of [embodiment 7] compound 164
Compound 164 (7.06g, 80%) is obtained according to the synthetic method of 1 compound 2 of embodiment.
The synthesis of [embodiment 8] compound 169
Compound 169 (6.85g, 80%) is obtained according to the synthetic method of 1 compound 2 of embodiment.
The synthesis of [embodiment 9] compound 254
Compound 254 (7.12g, 80%) is obtained according to the synthetic method of 1 compound 2 of embodiment.
The benzidine compound FD-MS value of synthesis of the embodiment of the present invention is as shown in table 1.
[table 1]
Embodiment FD-MS
Embodiment 1 M/z=881.39 (C66H47N3=881.38)
Embodiment 2 M/z=921.42 (C69H51N3=921.41)
Embodiment 3 M/z=1033.47 (C78H55N3=1033.44)
Embodiment 4 M/z=945.39 (C70H47N3O=945.37)
Embodiment 5 M/z=855.35 (C64H45N3=855.36)
Embodiment 6 M/z=972.43 (C72H52N4=972.42)
Embodiment 7 M/z=881.40 (C66H47N3=881.38)
Embodiment 8 M/z=855.37 (C64H45N3=855.36)
Embodiment 9 M/z=889.46 (C66H55N3=889.44)
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 2 1.96
Embodiment 2 18 1.98
Embodiment 3 40 1.99
Embodiment 4 56 1.94
Embodiment 5 97 1.92
Embodiment 6 117 2.03
Embodiment 7 164 2.06
Embodiment 8 169 1.90
Embodiment 9 254 1.89
[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 2/60nm.
[embodiment 11] device prepares embodiment:
The compound 2 of the coating of embodiment 10 is changed to the compound 18 of embodiment 2.
[embodiment 12] device prepares embodiment:
The compound 2 of the coating of embodiment 10 is changed to the compound 40 of embodiment 3.
[embodiment 13] device prepares embodiment:
The compound 2 of the coating of embodiment 10 is changed to the compound 56 of embodiment 4.
[embodiment 14] device prepares embodiment:
The compound 2 of the coating of embodiment 10 is changed to the compound 97 of embodiment 5.
[embodiment 15] device prepares embodiment:
The compound 2 of the coating of embodiment 10 is changed to the compound 117 of embodiment 8.
[embodiment 16] device prepares embodiment:
The compound 2 of the coating of embodiment 10 is changed to the compound 164 of embodiment 7.
[embodiment 17] device prepares embodiment:
The compound 2 of the coating of embodiment 10 is changed to the compound 169 of embodiment 8.
[embodiment 18] device prepares embodiment:
The compound 2 of the coating of embodiment 10 is changed to the compound 254 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 2/80nm, 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 164/60nm.
[embodiment 20] device prepares embodiment:
The compound 2 of the hole transmission layer of embodiment 19 is changed to the compound 18 of embodiment 2.
[embodiment 21] device prepares embodiment:
The compound 2 of the hole transmission layer of embodiment 19 is changed to the compound 40 of embodiment 3.
[embodiment 22] device prepares embodiment:
The compound 2 of the hole transmission layer of embodiment 19 is changed to the compound 56 of embodiment 4.
[embodiment 23] device prepares embodiment:
The compound 2 of the hole transmission layer of embodiment 19 is changed to the compound 97 of embodiment 5.
[embodiment 24] device prepares embodiment:
The compound 2 of the hole transmission layer of embodiment 19 is changed to the compound 117 of embodiment 6.
[embodiment 25] device prepares embodiment:
The compound 2 of the hole transmission layer of embodiment 19 is changed to the compound 164 of embodiment 7.
[embodiment 26] device prepares embodiment:
The compound 2 of the hole transmission layer of embodiment 19 is changed to the compound 169 of embodiment 8.
[embodiment 27] device prepares embodiment:
The compound 2 of the hole transmission layer of embodiment 19 is changed to the compound 254 of embodiment 9.
The characteristics of luminescence test result such as table 3 of luminescent device prepared by 10-27 of the embodiment of the present invention and comparative example 1 It is shown:
[table 3]
The above result shows that benzidine compound of the present invention is applied in organic electroluminescence device, especially As coating and/or hole transmission layer, organic electroluminescence device has the advantages that luminous efficiency height, long service life, Benzidine compound of the present invention is luminous organic material of good performance.
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 benzidine compound, which is characterized in that shown in any in its general formula of molecular structure such as chemical formula I, II:
Wherein, Ar1、Ar2Independently selected from substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C30 aryl, Any one in substituted or unsubstituted C3~C30 heteroaryl；R1、R2、R3、R4Independently selected from H, deuterium, substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C1~C10 alkylene, substituted or unsubstituted C6~C30 aryl, replace or not Substituted C6~C30 aryl amine, substituted or unsubstituted C6~C30 aralkyl, substituted or unsubstituted C6~C30 arylthio, Any one in substituted or unsubstituted C6~C30 aryloxy group, substituted or unsubstituted C3~C30 heteroaryl, a, b, c, d are only It is on the spot selected from 0 to 5 integer, when independently value is greater than 1 by a, b, c, d, corresponding multiple R1It can be selected from different groups, phase The multiple R answered2It can be selected from different groups, corresponding multiple R3It can be selected from different groups, corresponding multiple R4It can be selected from difference Group, multiple R1Between, multiple R2Between, multiple R3Between, multiple R4Between can be independently connected cyclization.
2. a kind of benzidine compound according to claim 1, which is characterized in that its molecular structure be selected from chemical formula III, It is any shown in IV:
3. a kind of benzidine compound according to claim 1, which is characterized in that R1、R2、R3、R4Independently selected from H, deuterium, Substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C6~C30 arylamine Any one in base, substituted or unsubstituted C3~C30 heteroaryl.
4. a kind of benzidine compound according to claim 1, which is characterized in that R1、R2、R3、R4Independently selected from H, deuterium, Methyl, ethyl, isopropyl, tert-butyl, sec-butyl, substituted or unsubstituted following group: phenyl, naphthalene, anthryl, phenanthryl, a word used for translation Piperidinyl, fluorenyl, Spirofluorene-based, carbazyl, furyl, thienyl, benzofuranyl, benzothienyl, dibenzofuran group, hexichol Bithiophene base, 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.
5. a kind of benzidine compound according to claim 1, which is characterized in that Ar1、Ar2Independently selected from substitution or not The following group replaced: phenyl, naphthalene, anthryl, phenanthryl, triphenylene, pyrenyl, base, acridinyl, fluorenyl, Spirofluorene-based, carbazole Base, furyl, thienyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophene, pyridyl group, pyrimidine Base, triazine radical, quinolyl, isoquinolyl, pyridazinyl, pyrazinyl, quinoxalinyl, quinazolyl, indyl, azepine carbazyl, In phenoxazine base, phenoxazine thiophene base, phenothiazinyl, imidazole radicals, benzimidazolyl, naphtho- imidazoles, phenanthro- imidazoles, pyrene and imidazole radicals Any one.
6. a kind of benzidine compound according to claim 1, which is characterized in that the benzidine compound is selected from as follows Any one in shown chemical structure:
7. a kind of benzidine compound according to claim 1, which is characterized in that a, b, c, d are 0.
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 benzidine 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, the described in any item benzidine compounds of claim 1~7 are contained in coating.
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 benzidine compounds of claim 1~7 in hole transmission layer.
CN201811422774.8A 2018-11-27 2018-11-27 A kind of benzidine compound and its organic electroluminescence device Pending CN109400520A (en)

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