CN108623481A - A kind of aromatic amine compound and its organic luminescent device - Google Patents

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

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Publication number
CN108623481A
CN108623481A CN201810563631.2A CN201810563631A CN108623481A CN 108623481 A CN108623481 A CN 108623481A CN 201810563631 A CN201810563631 A CN 201810563631A CN 108623481 A CN108623481 A CN 108623481A
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unsubstituted
substituted
aromatic amine
amine compound
luminescent device
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董秀芹
刘喜庆
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Changchun Haipurunsi Technology Co Ltd
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Changchun Haipurunsi Technology Co Ltd
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Abstract

A kind of aromatic amine compound of present invention offer and its organic luminescent device, are related to organic optoelectronic materials technology.The present invention by arylamine human subject the fluorenes class group such as penta phenanthrene of connection ring obtain a kind of aromatic amine compound, it has stronger cavity transmission ability and electron-blocking capability, thermal stability good, good film-forming property, it synthesizes simple to operation, it can be applied to be used as hole transmission layer and/or luminous auxiliary layer in organic luminescent device, it can effectively solve the problems, such as that carrier transport is uneven in organic luminescent device and short life, organic luminescent device have the advantages of luminous efficiency is high, long lifespan.

Description

A kind of aromatic amine compound and its organic luminescent device
Technical field
The present invention relates to organic photoelectrical material technical field more particularly to a kind of aromatic amine compounds and its organic illuminator Part.
Background technology
Organic luminescent device (OLED) shows as a kind of emerging flat panel, and 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, in recent years, OLED have obtained more and more applications in monitor market, become Display panel skill most potential at present Art.
Its structure of organic luminescent device is to generally comprise cathode, anode and in organic photoelectric function material between the two Material.Organic photoelectric functional material applied to OLED device can be roughly divided into two class materials from purposes：Charge injects and transmission Material, luminescent material.Further, charge injection transmission material is divided into electron injection material, electron transport material, and material is injected in hole Material, hole mobile material, shine auxiliary material, and effect is mainly equilbrium carrier injection so that electronics is shining with hole Layer effectively combines and forms exciton, and then shines, and improves luminous efficiency.Luminescent material generally comprises material of main part and object doping material On the one hand material, the wherein effect of material of main part are the transmission of equilbrium carrier, be conducive to the compound of electrons and holes, on the other hand then It is the self-quenching for reducing excessive concentration.
All in all, the direction of the following OLED be develop high efficiency, high brightness, the long-life, low cost white light parts and Full color display device, but the technological industrialization process still faces many critical issues, wherein and electron-transport speed is higher than sky Cave transmission speed, caused by carrier injection and transmission imbalance be limitation organic luminescent device luminous efficiency and service life carry High key factor, how to develop a kind of good organic photoelectrical material of hole transport performance becomes urgent problem to be solved.
Invention content
The object of the present invention is to provide a kind of aromatic amine compound and its organic luminescent device, arylamine chemical combination provided by the invention Object has good hole transport and electronic blocking performance, and thermal stability is good, and good film-forming property, synthetic method is simple to operation, makes With organic luminescent device prepared by the aromatic amine compound there is good luminous efficiency and service life to show.
The present invention provides a kind of aromatic amine compounds, and general formula of molecular structure is as shown in chemical formula I：
Wherein, Ar1、Ar2Independently selected from following group：
R1、R2Appointing in substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C60 aryl Meaning is a kind of；R3、R5、R6In H, substituted or unsubstituted C1-C30 alkyl any one, R5、R6Cyclization can be connected； R4Any one in singly-bound, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryls；
Ar3Selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C60 aryl, substitution or unsubstituted C3-C60 heteroaryls in any one.
Preferably, Ar1、Ar2Any one in following group：
Wherein, R1、R2Independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C60 aryl In any one；R3Any one in H, substituted or unsubstituted C1-C30 alkyl；R4Selected from singly-bound, substitution or not Any one in substituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryls.
Further preferably, R1、R2Independently selected from the alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene of C1-C10 Base, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substitution or unsubstituted Acridinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazyl, substituted or unsubstituted pyrenyl, substitution or not Substituted base, substituted or unsubstituted acenaphthenyl, substituted or unsubstituted furyl, substituted or unsubstituted benzothienyl, Substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofurans Any one in base.
Further preferably, R3、R5、R6In the alkyl of H, C1-C10 any one, R5、R6Cyclization can be connected.
Further preferably, R4Selected from singly-bound, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substitution or unsubstituted Anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted acridinyl, substitution or Unsubstituted fluorenyl, substituted or unsubstituted carbazyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted base, substitution Or unsubstituted acenaphthenyl, substituted or unsubstituted furyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzene And any one in furyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran group.
Most preferably, any one of aromatic amine compound of the present invention in chemical constitution as follows：
The present invention also provides a kind of organic luminescent device, the organic luminescent device includes cathode, anode and is placed in institute One or more organic matter layers between two electrodes are stated, the organic matter layer contains aromatic amine compound of the present invention.
Preferably, organic matter layer of the present invention includes hole transmission layer, is contained in hole transmission layer of the present invention Any aromatic amine compound.
Preferably, organic matter layer of the present invention includes the auxiliary layer that shines, and contains of the present invention in the auxiliary layer that shines A kind of aromatic amine compound.
Beneficial effects of the present invention：
A kind of aromatic amine compound of present invention offer and its organic luminescent device.The present invention passes through in triaryl amine agent structure The fluorenes class groups such as penta phenanthrene of ring, fluorenes, spiro fluorene are introduced, aromatic amine compound of the present invention is obtained.
On the one hand, the aromatic amine compound which forms has good cavity transmission ability and electronic blocking energy Power is applied to be used as hole transmission layer in organic luminescent device, can effectively improve the transmission in hole and reduce electronics to anode Loss improves hole and electronics in the recombination rate of luminescent layer, improves the luminous efficiency of device, and then avoid hole transmission layer side energy The accumulation of amount, to improve the service life of organic luminescent device.
On the one hand, the fluorenes class group conjugated system such as penta phenanthrene of ring, fluorenes, spiro fluorene is big, combined with triaryl amine increase it is whole Conjugated system, structural rigidity are big so that charge more disperses, and improves the stability of material；The molecule of aromatic amine compound simultaneously Amount increases, and both improves glass transition temperature, it is made to be not easy to crystallize, and reduce the coplanarity of molecule, be easy to form a film.
In addition, the fluorenes class group such as penta phenanthrene of ring, fluorenes, spiro fluorene carries alkyl substituent group, the dissolving of aromatic amine compound is increased Property, make it easy to synthesize and purify, and be conducive to its application in organic luminescent device preparation process, such as spin coating process.
Aromatic amine compound preparation method of the present invention is simple, and raw material is easy to get, and disclosure satisfy that industrialization demand.
Aromatic amine compound of the present invention be applied to organic luminescent device in, can respectively as hole transmission layer, shine Auxiliary layer has good luminous efficiency and Life Table using organic luminescent device prepared by aromatic amine compound of the present invention It is existing.
Specific implementation mode：
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 The every other embodiment that personnel are obtained without making creative work, belongs to protection scope of the present invention.
Aryl of the present invention refer to aromatic hydrocarbon molecule aromatic core carbon on remove a hydrogen atom after, be left univalent perssad it is total 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 not limited to oxygen, sulphur, nitrogen-atoms, and the heteroaryl can be bicyclic heteroaryl Or fused ring heteroaryl, embodiment may include pyridyl group, pyrimidine radicals, triazine radical, indyl, quinolyl, isoquinolyl, benzothiophene Base, benzofuranyl, dibenzofuran group, dibenzothiophene, carbazyl etc., but not limited to this.
The present invention provides a kind of aromatic amine compounds, and general formula of molecular structure is as shown in chemical formula I：
Wherein, Ar1、Ar2Independently selected from following group：
R1、R2Appointing in substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C60 aryl Meaning is a kind of；R3、R5、R6In H, substituted or unsubstituted C1-C30 alkyl any one, R5、R6Cyclization can be connected； R4Any one in singly-bound, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryls；
Ar3Selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C60 aryl, substitution or unsubstituted C3-C60 heteroaryls in any one.
According to the present invention, the substituted alkyl, substituted aryl, substituted heteroaryl, wherein the substituent group is independent Ground is selected from deuterium, C1-C10Alkyl, C6-C24Aryl or C3-C20Heterocycle.
Preferably, Ar1、Ar2Any one in following group：
Wherein, R1、R2Independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C60 aryl In any one；R3Any one in H, substituted or unsubstituted C1-C30 alkyl；R4Selected from singly-bound, substitution or not Any one in substituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryls.
Further preferably, R1、R2Independently selected from the alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene of C1-C10 Base, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substitution or unsubstituted Acridinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazyl, substituted or unsubstituted pyrenyl, substitution or not Substituted base, substituted or unsubstituted acenaphthenyl, substituted or unsubstituted furyl, substituted or unsubstituted benzothienyl, Substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofurans Any one in base.
Further preferably, R3、R5、R6In the alkyl of H, C1-C10 any one, R5、R6Cyclization can be connected.It is optimal Choosing, R3、R5、R6Appointing in H, methyl, ethyl, propyl, isopropyl, normal-butyl, tertiary butyl, sec-butyl, isobutyl group Meaning is a kind of.
Further preferably, R4Selected from singly-bound, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substitution or unsubstituted Anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted acridinyl, substitution or Unsubstituted fluorenyl, substituted or unsubstituted carbazyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted base, substitution Or unsubstituted acenaphthenyl, substituted or unsubstituted furyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzene And any one in furyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran group.
Most preferably, as an example, it is not particularly limited, a kind of aromatic amine compound of the present invention is selected from as followsization Learn any one in structure：
Aromatic amine compound of the present invention is obtained by following synthetic route：
Wherein, Ar1、Ar2Independently selected from following group：
R1、R2Appointing in substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C60 aryl Meaning is a kind of；R3、R5、R6In H, substituted or unsubstituted C1-C30 alkyl any one, R5、R6Cyclization can be connected； R4Any one in singly-bound, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryls；
Ar3Selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C60 aryl, substitution or unsubstituted C3-C60 heteroaryls in any one.
Aromatic amine compound of the present invention obtains as follows：
1, raw material a-1, under hydrogen environment, Pd/C obtains intermediate b-1 as reducing agent, reduction；
2, intermediate b-1, Br2, bromination obtains intermediate b-2-1；Intermediate b-2-1, chloranil are aoxidized as oxidant To intermediate b-3-1；Intermediate b-3-1, R1I、R2Intermediate b-5-1 is obtained by the reaction as alkali in I, t-BuOK；
3, intermediate b-1, Br2, bromination obtains intermediate b-2-2；Intermediate b-2-1, chloranil are aoxidized as oxidant To intermediate b-3-2；Intermediate b-3-2, R1I、R2Intermediate b-4 is obtained by the reaction as alkali in I, t-BuOK；Intermediate b-4, original Expect R4-B(OH)2, with Pd (PPh3)4For catalyst, K2CO3For alkali, intermediate b-5-2 is obtained by the reaction；
4, intermediate b-5-1, connection boric acid pinacol fat, with Pd (PPh3)4For catalyst, K2CO3For alkali, in being obtained by the reaction Mesosome b-6-1；Intermediate b-6-1, raw material Br-R4- Br, with Pd (PPh3)4For catalyst, K2CO3For alkali, intermediate is obtained by the reaction b-7-1；
Intermediate b-5-2, connection boric acid pinacol fat, with Pd (PPh3)4For catalyst, K2CO3For alkali, centre is obtained by the reaction Body b-6-2；Intermediate b-6-2, raw material Br-R4- Br, with Pd (PPh3)4For catalyst, K2CO3For alkali, intermediate b- is obtained by the reaction 7-2；
Raw material a-2, connection boric acid pinacol fat, with Pd (PPh3)4For catalyst, K2CO3For alkali, intermediate b- is obtained by the reaction 6-3；Intermediate b-6-3, raw material Br-R4- Br, with Pd (PPh3)4For catalyst, K2CO3For alkali, intermediate b-7-3 is obtained by the reaction；
Work as R4For singly-bound, Ar1- Br or Ar2- Br in a-2, b-5-1, b-5-2 any one；
Work as R4It is not singly-bound, Ar1- Br or Ar2- Br in a-7-1, b-7-2, b-7-3 any one；
5, raw material a-3, intermediate A r2- Br, with Pd2(dba)3、P(t-Bu)3For catalyst, NaOBu-t is alkali, is passed through Intermediate b-8 is obtained by the reaction in Buchwald；Intermediate b-8, Ar1- Br, with Pd2(dba)3、P(t-Bu)3For catalyst, NaOBu- T is alkali, and chemical compounds I is obtained by the reaction by Buchwald.
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 luminescent device, the organic luminescent device includes cathode, anode and is placed in institute One or more organic matter layers between two electrodes are stated, the organic matter layer contains aromatic amine compound of the present invention.
Organic matter layer of the present invention is selected from hole injection layer, hole transmission layer, luminous auxiliary layer, luminescent layer and (shines Main body：Object), hole blocking layer, electron transfer layer, at least one of electron injecting layer.The auxiliary layer that wherein shines is located at sky Between cave transport layer and luminescent layer, there are good cavity transmission ability and electron-blocking capability, be used for equilbrium carrier, improves The recombination probability in hole and electronics in luminescent layer avoids transmission of the electronics to anode-side, to improve making for organic luminescent device Use the service life.
Preferably, the organic matter layer includes hole transmission layer, is contained in hole transmission layer of the present invention any Aromatic amine compound.
Preferably, the organic matter layer includes the auxiliary layer that shines, containing of the present invention any in the auxiliary layer that shines Aromatic amine compound.
OLED structure of the present invention is：ITO is as transparent anode；2-TNATA is used as hole injection layer； NPB or of the present invention aromatic amine compounds are as hole transmission layer；Aromatic amine compound of the present invention is as the auxiliary that shines Layer, ADN/BDAVBi are used as luminescent layer substance；Alq3As electron transfer layer；LiF is used as electron injecting layer；Al is used as cathode.
Aromatic amine compound of the present invention is used as hole transmission layer, to manufacture the organic light emission of construction same as below Device：
ITO/2-TNATA (60nm)/aromatic amine compound of the present invention (30nm)/ADN：BDAVBi(30nm)/Alq3 (30nm)/LiF(1nm)/Al(300nm)。
Aromatic amine compound of the present invention is used separately as the auxiliary layer that shines, to manufacture the organic of construction same as below Luminescent device：
ITO/2-TNATA (60nm)/NPB (30nm)/aromatic amine compound of the present invention (20nm)/ADN：BDAVBi (30nm)/Alq3(30nm)/LiF(1nm)/Al(300nm)。
Aromatic amine compound of the present invention is used as hole mobile material and luminous auxiliary layer, same as below to have manufactured The organic luminescent device of construction：
ITO/2-TNATA (60nm)/aromatic amine compound of the present invention (30nm)/aromatic amine compound of the present invention (20nm)/ADN：BDAVBi(30nm)/Alq3(30nm)/LiF(1nm)/Al(300nm)。
Organic luminescent device of the present invention can be widely applied to Display panel, lighting source, flexibility OLED, Electronic Paper, The fields such as Organophotoreceptor or Organic Thin Film Transistors, direction board, signal lamp.
The synthesis of [embodiment 1] compound 3
Step1：Be added in reactor 4H- rings penta luxuriant and rich with fragrance (1.90g, 10mmol), 5% Pd/C (1.6g), ethyl alcohol 20mL, pressure Power is the hydrogen environment of 2.75bar, is stirred to react under room temperature for 24 hours, and after reaction, filtering, evaporation solvent obtains centre Body 3-1 (1.63g, 85%).
Step2：Intermediate 3-1 (1.92g, 10mmol), CCl are added in reactor420mL is gradually cooled to 0 afterwards DEG C, it is slowly added to Br2With reaction 4h is stirred at room temperature after reaction, Na is added in (1.60g, 10mmol)2SO3Organic layer is detached, Organic layer MgSO4G is dried and evaporated solvent, then is recrystallized to give intermediate 3-2 (2.17g, 80%) through n-hexane.
Step3：Intermediate 3-2 (2.71g, 10mmol), tetrachloroquinone (2.58g, 10.5mmo), two are added in reactor Toluene mL is stirred to react 72h under the conditions of 110 DEG C, is cooled to room temperature after reaction, solvent evaporated, residue crosses silicagel column Chromatography obtains intermediate 3-3 (2.18g, 81%).
Step4：Intermediate 3-3 (2.69g, 10mmol), t-BuOK (8.98g, 80mmol), 25mL are added in reactor The DMSO of HMPA, 25mL, stir 1h at room temperature, after be cooled to 0 DEG C, be slowly added to CH3I (11.35g, 80mmol), is stirred to react 30h, the rear distilled water that is added stop reaction, and reacting coarse product is extracted three times with dichloromethane, and organic layer is dried and evaporated with MgSO4g Solvent crosses silica gel column chromatography and obtains intermediate 3-4 (2.32g, 78%).
Step5：4- aminobphenyls (1.35g, 8mmol), intermediate 3-4 (4.76g, 16mmol), Pd are added in reactor2 (dba)3(0.41g, 0.48mmol), P (t-Bu)3(0.34,1.61mmol), NaOt-Bu (5.38g, 48mmol), toluene solution 200mL reacts for 24 hours under the conditions of 100 DEG C, and ether and water is used to extract organic phase, organic layer MgSO after reaction4It is dry, it is dense Contracting organic matter crosses column chromatography, is recrystallized to give compound 3 (3.76g, 78%).
The synthesis of [embodiment 2] compound 9
Compound 9 (3.85g, 75%) is obtained according to the synthetic method of compound 3.
The synthesis of [embodiment 3] compound 56
Step1：Compound 56-1 is obtained according to the synthetic method of 1 compound 3-4 of embodiment；
Step2：Aniline (0.75g, 8mmol), intermediate 56-1 (3.37g, 8mmol), Pd are added in reactor2(dba)3 (0.20g, 0.24mmol), P (t-Bu)3(0.17g, 0.85mmol), NaOt-Bu (2.69g, 24mmol), toluene solution 100mL reacts for 24 hours under the conditions of 100 DEG C, and ether and water is used to extract organic phase, organic layer MgSO after reaction4It is dry, it is dense Contracting organic matter crosses column chromatography, is recrystallized to give intermediate 56-2 (2.71g, 78%).
Step3：In reactor be added 56-2 (3.47g, 8mmol), bromo- 9, the 9- diphenylfluorenes (3.18g, 8mmol) of 2-, Pd2(dba)3(0.20g, 0.24mmol), P (t-Bu)3(0.17,0.85mmol), NaOt-Bu (2.69g, 24mmol), toluene are molten Liquid 100mL reacts for 24 hours under the conditions of 100 DEG C, ether and water is used to extract organic phase, organic layer MgSO after reaction4It is dry, Condensed organic crosses column chromatography, is recrystallized to give midbody compound 56 (4.32g, 72%).
The synthesis of [embodiment 4] compound 112
Compound 112 (3.86g, 75%) is obtained according to the synthetic method of compound 56.
The synthesis of [embodiment 5] compound 167
Compound 167 (4.27g, 76%) is obtained according to the synthetic method of compound 56.
The synthesis of [embodiment 6] compound 215
Step1：Intermediate 3-4 (2.97,10mmol), connection boric acid pinacol fat are added under nitrogen protection, in reactor (3.81g, 15mmol), K2CO3Solution (16mL, 2mol/L), Pd (PPh3)4(0.21g, 0.18mmol), 48h is reacted at 90 DEG C, Separating-purifying obtains intermediate 215-1 (2.75g, 80%).
Step2：The bromo- 2- iodine pyridines (2.61g, 9.2mmol) of 5-, intermediate are added under nitrogen protection, in reaction vessel 215-1 (2.89g, 8.4mmol), tetra-triphenylphosphine palladium (0.09g, 0.08mmol), potassium carbonate (3.48g, 25.2mmol), toluene 60mL, ethyl alcohol 20mL and distilled water 20mL stir 3h under the conditions of 120 DEG C.Distilled water stops reaction, acetic acid after reaction terminates Ethyl ester extracts, organic layer MgSO4Dry, solvent is removed in vacuum distillation, is purified to obtain intermediate later with silica gel column chromatography 215-2 (2.36g, 75%).
Step3：Naphthalidine (1.15g, 8mmol), intermediate 215-2 (2.99g, 8mmol), Pd are added in reactor2 (dba)3(0.20g, 0.24mmol), P (t-Bu)3(0.17g, 0.85mmol), NaOt-Bu (2.69g, 24mmol), toluene solution 100mL reacts for 24 hours under the conditions of 100 DEG C, and ether and water is used to extract organic phase, organic layer MgSO after reaction4It is dry, it is dense Contracting organic matter crosses column chromatography, is recrystallized to give intermediate 215-3 (2.58g, 74%).
Step4：215-3 (3.49g, 8mmol), intermediate 3-4 (2.38g, 8mmol), Pd are added in reactor2(dba)3 (0.20g, 0.24mmol), P (t-Bu)3(0.17,0.85mmol), NaOt-Bu (2.69g, 24mmol), toluene solution 100mL, It is reacted under the conditions of 100 DEG C for 24 hours, ether and water is used to extract organic phase, organic layer MgSO after reaction4Dry, concentration is organic Object crosses column chromatography, is recrystallized to give midbody compound 215 (3.81g, 73%).
The synthesis of [embodiment 7] compound 220
Compound 220 (4.15g, 71%) is obtained according to the synthetic method of compound 215.
The synthesis of [embodiment 8] compound 251
Step1：Intermediate 3-1 (1.92g, 10mmol), CCl are added in reactor420mL is gradually cooled to 0 afterwards DEG C, it is slowly added to Br2With reaction 4h is stirred at room temperature after reaction, Na is added in (3.20g, 20mmol)2SO3Organic layer is detached, Organic layer MgSO4G is dried and evaporated solvent, then is recrystallized to give intermediate 251-1 (2.80g, 80%) through n-hexane.
Step2：In reactor be added intermediate 251-1 (3.50g, 10mmol), tetrachloroquinone (2.58g, 10.5mmo), Dimethylbenzene 20mL is stirred to react 72h under the conditions of 110 DEG C, is cooled to room temperature after reaction, solvent evaporated, residue crosses silicon Plastic column chromatography obtains intermediate 251-2 (2.82g, 81%).
Step3：Intermediate 251-2 (3.48g, 10mmol), t-BuOK (8.98g, 80mmol), 25mL are added in reactor HMPA, 25mL DMSO, stir 1h at room temperature, after be cooled to 0 DEG C, be slowly added to iodobenzene (16.32g, 80mmol), stirring is anti- 30h is answered, the rear distilled water that is added stops reaction, and reacting coarse product is extracted three times with dichloromethane, and organic layer is dried with MgSO4g, is steamed Solvent is sent out, silica gel column chromatography is crossed and obtains intermediate 251-3 (3.85g, 77%).
Step4：Under nitrogen protection, isopropyl ylboronic acid (0.81g, 9.2mmol), intermediate 251-3 are added in reaction vessel (4.20g, 8.4mmol), tetra-triphenylphosphine palladium (0.09g, 0.08mmol), potassium carbonate (3.48g, 25.2mmol), toluene 60mL, Ethyl alcohol 20mL and distilled water 20mL stirs 3h under the conditions of 120 DEG C.Distilled water stops reaction, ethyl acetate after reaction terminates Extraction, organic layer MgSO4Dry, solvent is removed in vacuum distillation, is purified to obtain intermediate 251-4 later with silica gel column chromatography (2.88g, 74%).
Step5：In reactor be added 4- isopropyl anilines (1.08g, 8mmol), intermediate 251-4 (3.71g, 8mmol), Pd2(dba)3(0.41g, 0.48mmol), P (t-Bu)3(0.34,1.61mmol), NaOt-Bu (5.38g, 48mmol), toluene are molten Liquid 200mL reacts for 24 hours under the conditions of 100 DEG C, ether and water is used to extract organic phase, organic layer MgSO after reaction4It is dry, Condensed organic crosses column chromatography, is recrystallized to give intermediate 251-5 (2.98g, 73%).
Step6：Intermediate 251-5 (4.08g, 8mmol), intermediate 3-4 (2.38g, 8mmol), Pd are added in reactor2 (dba)3(0.41g, 0.48mmol), P (t-Bu)3(0.34,1.61mmol), NaOt-Bu (5.38g, 48mmol), toluene solution 200mL reacts for 24 hours under the conditions of 100 DEG C, and ether and water is used to extract organic phase, organic layer MgSO after reaction4It is dry, it is dense Contracting organic matter crosses column chromatography, is recrystallized to give compound 251 (4.17g, 71%).
The aromatic amine compound FD-MS values of synthesis of the embodiment of the present invention are as shown in table 1.
【Table 1】
Embodiment FD-MS
Embodiment 1 M/z=601.32 (C46H35N=601.28)
Embodiment 2 M/z=641.33 (C49H39N=641.31)
Embodiment 3 M/z=749.33 (C58H39N=749.31)
Embodiment 4 M/z=643.29 (C49H41N=643.32)
Embodiment 5 M/z=701.33 (C54H39N=701.31)
Embodiment 6 M/z=652.27 (C49H36N2=652.29)
Embodiment 7 M/z=729.36 (C56H43N=729.34)
Embodiment 8 M/z=733.40 (C56H47N=733.37)
[comparative example 1] device prepares embodiment：
Ito glass substrate is placed in distilled water and is cleaned 2 times, ultrasonic washing 30 minutes is different after distilled water cleans Ultrasonic washing is later dry in order for propyl alcohol, acetone, methanol equal solvent, is transferred in plasma washing machine, by above-mentioned base Plate washs 5 minutes, is sent in evaporator.
Hole injection layer 2-TNATA/60nm is successively deposited on the ito transparent electrode being already prepared to, vapor deposition hole passes Defeated layer NPB/30nm, vapor deposition main body A DN：Adulterate 2% mixing of BDAVBi/30nm and then vapor deposition electron transfer layer Alq3/30nm、 Electron injecting layer LiF/1nm, cathode Al/300nm.
[embodiment 9] device prepares embodiment：
Ito glass substrate is placed in distilled water and is cleaned 2 times, ultrasonic washing 30 minutes is different after distilled water cleans Ultrasonic washing is later dry in order for propyl alcohol, acetone, methanol equal solvent, is transferred in plasma washing machine, by above-mentioned base Plate washs 5 minutes, is sent in evaporator.
Hole injection layer 2-TNATA/50nm is successively deposited on the ito transparent electrode being already prepared to, vapor deposition hole passes Compound 3/30nm, the vapor deposition main body A DN of defeated layer embodiment 1：It adulterates 2% mixing of BDAVBi/30nm and then vapor deposition electronics passes Defeated layer Alq3/ 30nm, electron injecting layer LiF/1nm, cathode Al/300nm.
[embodiment 10] device prepares embodiment：
The compound 3 of the embodiment 1 of the hole transmission layer of embodiment 9 is changed to the compound 9 of embodiment 2.
[embodiment 11] device prepares embodiment：
The compound 3 of the embodiment 1 of the hole transmission layer of embodiment 9 is changed to the compound 56 of embodiment 3.
[embodiment 12] device prepares embodiment：
Ito glass substrate is placed in distilled water and is cleaned 2 times, ultrasonic washing 30 minutes is different after distilled water cleans Ultrasonic washing is later dry in order for propyl alcohol, acetone, methanol equal solvent, is transferred in plasma washing machine, by above-mentioned base Plate washs 5 minutes, is sent in evaporator.
Hole injection layer 2-TNATA/50nm is successively deposited on the ito transparent electrode being already prepared to, vapor deposition hole passes Defeated layer NPB, the compound 112/30nm that the auxiliary layer embodiment 4 that shines is deposited, vapor deposition main body A DN：Doping BDAVBi 2% mixing/ 30nm and then vapor deposition electron transfer layer Alq3/ 30nm, electron injecting layer LiF/1nm, cathode Al/300nm.
[embodiment 13] device prepares embodiment：
The compound 112 of the embodiment 4 of luminous auxiliary layer in embodiment 12 is changed to the compound 167 of embodiment 5.
[embodiment 14] device prepares embodiment：
The compound 112 of the embodiment 4 of luminous auxiliary layer in embodiment 12 is changed to the compound 215 of embodiment 6.
[embodiment 15] device prepares embodiment：
Ito glass substrate is placed in distilled water and is cleaned 2 times, ultrasonic washing 30 minutes is different after distilled water cleans Ultrasonic washing is later dry in order for propyl alcohol, acetone, methanol equal solvent, is transferred in plasma washing machine, by above-mentioned base Plate washs 5 minutes, is sent in evaporator.
Hole injection layer 2-TNATA/50nm is successively deposited on the ito transparent electrode being already prepared to, vapor deposition hole passes The compound 3 of defeated layer embodiment 1, the compound 220/30nm that the auxiliary layer embodiment 7 that shines is deposited, vapor deposition main body A DN：Doping 2% mixing of BDAVBi/30nm and then vapor deposition electron transfer layer Alq3/ 30nm, electron injecting layer LiF/1nm, cathode Al/ 300nm。
[embodiment 16] device prepares embodiment：
The compound 220 of the embodiment 7 of luminous auxiliary layer in embodiment 13 is changed to the compound 251 of embodiment 8.
[embodiment 17] device prepares embodiment：
The compound 220 of the embodiment 7 of luminous auxiliary layer in embodiment 13 is changed to the compound 9 of embodiment 2.
[embodiment 18] device prepares embodiment：
The compound 220 of the embodiment 7 of luminous auxiliary layer in embodiment 13 is changed to the compound 56 of embodiment 3.
The characteristics of luminescence test result such as table 2 of luminescent device prepared by 9-18 of the embodiment of the present invention and comparative example 1 It is shown.
【Table 2】
The above result shows that aromatic amine compound of the invention is applied in organic luminescent device, passed especially as hole Defeated layer and luminous auxiliary layer, the luminous efficiency of organic luminescent device and service life are significantly increased, aromatic amine compound of the invention It 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 present invention improvement on various forms or details, these improvement also fall into this hair In bright protection domain.

Claims (9)

1. a kind of aromatic amine compound, which is characterized in that its general formula of molecular structure is as shown in chemical formula I：
Wherein, Ar1、Ar2Independently selected from following group：
R1、R2It is any one in substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C60 aryl Kind；R3、R5、R6In H, substituted or unsubstituted C1-C30 alkyl any one, R5、R6Cyclization can be connected；R4Choosing From any one in singly-bound, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryls；
Ar3Selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3- Any one in C60 heteroaryls.
2. a kind of aromatic amine compound according to claim 1, which is characterized in that Ar1、Ar2In following group Any one：
Wherein, R1、R2In substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C60 aryl Any one；R3Any one in H, substituted or unsubstituted C1-C30 alkyl；R4Selected from singly-bound, substitution or unsubstituted C6-C30 aryl, any one in substituted or unsubstituted C3-C30 heteroaryls.
3. a kind of aromatic amine compound according to claim 1, which is characterized in that R1、R2Independently selected from the alkane of C1-C10 Base, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthrene Base, substituted or unsubstituted triphenylene, substituted or unsubstituted acridinyl, substituted or unsubstituted fluorenyl, substitution do not take The carbazyl in generation, substituted or unsubstituted pyrenyl, substituted or unsubstituted base, substituted or unsubstituted acenaphthenyl, substitution or not It is substituted furyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted Any one in dibenzothiophene, substituted or unsubstituted dibenzofuran group.
4. a kind of aromatic amine compound according to claim 1, which is characterized in that R3、R5、R6Independently selected from H, C1-C10 Alkyl in any one, R5、R6Cyclization can be connected.
5. a kind of aromatic amine compound according to claim 1, which is characterized in that R4Selected from singly-bound, substituted or unsubstituted benzene Base, substituted or unsubstituted naphthalene, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted three Phenylene, substituted or unsubstituted acridinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazyl, substitution or not Substituted pyrenyl, substituted or unsubstituted base, substituted or unsubstituted acenaphthenyl, substituted or unsubstituted furyl, substitution or Unsubstituted benzothienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzothiophene, substitution or Any one in unsubstituted dibenzofuran group.
6. a kind of aromatic amine compound according to claim 1, which is characterized in that the aromatic amine compound is selected from as follows Any one in chemical constitution：
7. a kind of organic luminescent device, which is characterized in that the organic luminescent device include cathode, anode and be placed in it is described two electricity One or more organic matter layers between pole, the organic matter layer contain claim 1~6 any one of them arylamine chemical combination Object.
8. according to a kind of organic luminescent device described in claim 7, which is characterized in that the organic matter layer includes that hole passes Defeated layer contains claim 1~7 any one of them aromatic amine compound in hole transmission layer.
9. according to a kind of organic luminescent device described in claim 7, which is characterized in that the organic matter layer includes luminous auxiliary Layer is helped, contains claim 1~7 any one of them aromatic amine compound in the auxiliary layer that shines.
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