CN106749339A - A kind of aromatic amine analog derivative and its preparation method and application - Google Patents
A kind of aromatic amine analog derivative and its preparation method and application Download PDFInfo
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- CN106749339A CN106749339A CN201611036783.4A CN201611036783A CN106749339A CN 106749339 A CN106749339 A CN 106749339A CN 201611036783 A CN201611036783 A CN 201611036783A CN 106749339 A CN106749339 A CN 106749339A
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- aromatic amine
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- 150000004982 aromatic amines Chemical class 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title claims abstract description 29
- 238000005401 electroluminescence Methods 0.000 claims abstract description 16
- 230000005540 biological transmission Effects 0.000 claims abstract description 13
- 239000010410 layer Substances 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 18
- 238000006467 substitution reaction Methods 0.000 claims description 13
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 238000003786 synthesis reaction Methods 0.000 claims description 9
- 239000005416 organic matter Substances 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000012044 organic layer Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 26
- 230000008901 benefit Effects 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 4
- 238000013461 design Methods 0.000 abstract description 2
- 238000005516 engineering process Methods 0.000 abstract description 2
- 230000005693 optoelectronics Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000470 constituent Substances 0.000 description 20
- 238000001819 mass spectrum Methods 0.000 description 20
- 238000005259 measurement Methods 0.000 description 20
- 239000012071 phase Substances 0.000 description 12
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000007738 vacuum evaporation Methods 0.000 description 5
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 4
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 0 *N*=*1C(CC=CC=C2)=C2N2c(cccc3)c3N[C@@]12 Chemical compound *N*=*1C(CC=CC=C2)=C2N2c(cccc3)c3N[C@@]12 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- -1 nitro, hydroxyl Chemical group 0.000 description 3
- 230000027756 respiratory electron transport chain Effects 0.000 description 3
- GMVJKSNPLYBFSO-UHFFFAOYSA-N 1,2,3-tribromobenzene Chemical compound BrC1=CC=CC(Br)=C1Br GMVJKSNPLYBFSO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 241001597008 Nomeidae Species 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- 150000005004 2-naphthylamines Chemical class 0.000 description 1
- WRDWWAVNELMWAM-UHFFFAOYSA-N 4-tert-butylaniline Chemical compound CC(C)(C)C1=CC=C(N)C=C1 WRDWWAVNELMWAM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- INJBSCDDUIMCJC-UHFFFAOYSA-N Brc(cc1)ccc1-[n]1c2nc(cccc3)c3[n]2c2ccccc12 Chemical compound Brc(cc1)ccc1-[n]1c2nc(cccc3)c3[n]2c2ccccc12 INJBSCDDUIMCJC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UCWLKOMHZBAXKC-UHFFFAOYSA-N C(C1)C=Cc2c1[n](c(cccc1)c1[n]1-c(cc3)ccc3Nc3ccccc3)c1n2 Chemical compound C(C1)C=Cc2c1[n](c(cccc1)c1[n]1-c(cc3)ccc3Nc3ccccc3)c1n2 UCWLKOMHZBAXKC-UHFFFAOYSA-N 0.000 description 1
- XEPJMTAAFOCLEQ-UHFFFAOYSA-N CC(CC=C1)Cc([nH]2)c1[n]1c2nc2c1cccc2 Chemical compound CC(CC=C1)Cc([nH]2)c1[n]1c2nc2c1cccc2 XEPJMTAAFOCLEQ-UHFFFAOYSA-N 0.000 description 1
- VQLSHHHRZRYBHT-UHFFFAOYSA-N CCCc(cccc1)c1-[n]1c(cccc2)c2nc1C Chemical compound CCCc(cccc1)c1-[n]1c(cccc2)c2nc1C VQLSHHHRZRYBHT-UHFFFAOYSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000004017 vitrification Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention provides a kind of aromatic amine analog derivative and its preparation method and application, is related to organic optoelectronic materials technology.By optimizing Molecular Design, aromatic amine analog derivative obtained by the present invention has good cavity transmission ability, can be used to prepare organic electroluminescence device, especially as the hole mobile material in organic electroluminescence device, high efficiency and long-life advantage are shown, better than existing conventional OLED.The present invention also provides a kind of preparation method of aromatic amine analog derivative, and the preparation method is simple, raw material is easy to get.
Description
Technical field
The present invention relates to organic photoelectrical material technical field, and in particular to a kind of aromatic amine analog derivative and its preparation side
Method and application.
Background technology
Organic Light Emitting Diode (Organic Light-Emitting Diodes, electroluminescent) has become in recent years
Domestic and international very popular emerging FPD industry, being primarily due to electroluminescent display has self-luminous, visual angle wide
(up to more than 170 °), fast response time (~1 μ s), color is true to nature, definition is high, high-luminous-efficiency, operating voltage it is low (3~
10V), plate thickness thin (be less than 2mm), large scale and flexible panel can be made and Making programme is simple etc. that protrusion is excellent
Gesture, the potentiality with low cost, therefore, it is considered to be follow-on flat panel display.
OLED luminescent devices just as the structure of sandwich, including electrode material film layer, and be clipped in Different electrodes film layer it
Between organic functional material, various difference in functionality materials are overlapped mutually according to purposes and collectively constitute together OLED luminescent devices.
As current driving apparatus, when the two end electrodes applied voltage to OLED luminescent devices, and by the organic layer function of electric field action
Positive and negative charge in film layer, positive and negative charge is further combined in luminescent layer, that is, produce OLED electroluminescent.
Being applied to the oled light sulfate ferroelectric functional material of OLED can be divided into two major classes, i.e. electric charge injection transmission from purposes
Material and luminescent material, further, can also inject charge into transmission material and be divided into electron injection transmission material and hole injection biography
Defeated material, can also be divided into main body luminescent material and dopant material by luminescent material.In order to make high performance OLED photophores
Part, it is desirable to which various organic functional materials possess good photoelectric characteristic, for example, as charge transport materials, it is desirable to good
Carrier mobility, high-vitrification conversion temperature etc., the material of main part requirement material as luminescent layer has good bipolarity,
Appropriate HOMO/LUMO energy ranks etc..
All in all, the direction of 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 key issues, how to design new performance more preferable
Material is adjusted, and is always those skilled in the art's problem demanding prompt solution.
The content of the invention
It is an object of the invention to provide a kind of aromatic amine analog derivative and its preparation method and application, what the present invention was provided
Organic compound thermal stability is high, good film-forming property, and preparation method is simple, the organic luminescent device being made up of the compound, table
Reveal high efficiency, long-life, glass transition temperature and non crystallized advantage high, are the luminous organic materials of function admirable.
Present invention firstly provides a kind of aromatic amine analog derivative, structural formula is：
Wherein, R1、R2The independent substituted or unsubstituted aryl selected from C6~C50, the substitution of C10~C30 or unsubstituted
Condensed ring, the substituted or unsubstituted condensed hetero ring of C8~C30 in one kind.
Preferably, the R1、R2The independent substituted or unsubstituted aryl selected from C6~C9, the substitution of C10~C14 or
One kind in unsubstituted condensed ring.
Preferably, the R1Selected from following chemical formula any one：
Wherein, Ra is alkyl, halogen, cyano group, hydroxyl or sulfydryl；
* the connecting key of substitution base and compound is represented.
Preferably, the R2Selected from following chemical formula any one：
Preferably, the aromatic amine analog derivative is selected from any one in structure shown in following TM1~TM8：
The present invention also provides a kind of preparation method of preparation of aromatic amine derivatives, and syntheti c route is as follows：
Wherein, R1、R2The independent substituted or unsubstituted aryl selected from C6~C50, the substitution of C10~C30 or unsubstituted
Condensed ring, the substituted or unsubstituted condensed hetero ring of C8~C30 in one kind.
The present invention also provides application of the above-mentioned preparation of aromatic amine derivatives in organic electroluminescence device.
Preferably, the organic electroluminescence device includes anode, negative electrode and organic matter layer, contains in the organic matter layer
Aromatic amine analog derivative described in any one.
Preferably, the aromatic amine analog derivative is used to prepare the hole transmission layer of organic electroluminescence device.
Beneficial effects of the present invention:
Present invention firstly provides a kind of aromatic amine analog derivative, the aromatic amine analog derivative has structure shown in formula I,
By introducing condensed ring class rigid structure, make that the aromatic amine analog derivative thermal stability obtained by the present invention is high, good film-forming property,
Can be used to prepare organic electroluminescence device, especially as the hole mobile material in organic electroluminescence device, show
High efficiency, long-life and be difficult crystallization advantage, better than existing conventional OLED.The present invention also provides a kind of aromatic amine
The preparation method of derivative, the preparation method is simple, raw material is easy to get, the need for disclosure satisfy that industrialization development.Fragrance of the invention
Race's amine derivant has good application effect in OLED luminescent devices, with good industrialization prospect.
Specific embodiment
For a further understanding of the present invention, the preferred embodiment of the invention is described with reference to embodiment, but
It should be appreciated that these descriptions are simply to further illustrate the features and advantages of the present invention, rather than to the claims in the present invention
Limitation.
Present invention firstly provides a kind of aromatic amine analog derivative, structural formula is：
Wherein, R1、R2The independent substituted or unsubstituted aryl selected from C6~C50, the substitution of C10~C30 or unsubstituted
Condensed ring, the substituted or unsubstituted condensed hetero ring of C8~C30 in one kind.
Preferably R1、R2The independent substituted or unsubstituted aryl selected from C6~C9, the substitution of C10~C14 or unsubstituted
Condensed ring in one kind.
According to the present invention, described substituted aryl, the five-ring heterocycles of substitution, the hexa-member heterocycle of substitution, substitution it is thick miscellaneous
In ring, substitution base independence selected from alkyl, alkoxy, amino, halogen, cyano group, nitro, hydroxyl or sulfydryl.
Further preferably R1Selected from following chemical formula any one：
Wherein, Ra is alkyl, halogen, cyano group, hydroxyl or sulfydryl；
* the connecting key of substitution base and compound is represented.
R2Selected from following chemical formula any one：
Specifically, the aromatic amine analog derivative is preferably selected from any one in structure shown in following TM1~TM8：
The present invention also provides a kind of preparation method of aromatic amine analog derivative, and syntheti c route is as follows：
Wherein, R1、R2The independent substituted or unsubstituted aryl selected from C6~C50, the substitution of C10~C30 or unsubstituted
Condensed ring, the substituted or unsubstituted condensed hetero ring of C8~C30 in one kind.
According to the present invention, the compound shown in intermediate A is prepared according to method as follows：
Under nitrogen protection, benzimidazole is simultaneously<1,2-A>Benzimidazole is with halide in cuprous iodide, potassium carbonate, 18-
There is coupling reaction in the presence of crown- 6- ethers and DMPU, obtain intermediate A.
According to the present invention, the compound shown in intermediate B is prepared according to method as follows：
Under nitrogen protection, palladium and tri-butyl phosphine are catalyst, in the case that sodium tert-butoxide is alkali, by intermediate
B reacts with aromatic amine compounds, obtains intermediate B.
According to the present invention, the compound shown in target product is prepared according to method as follows：
Under nitrogen protection, palladium and tri-butyl phosphine are catalyst, in the case that sodium tert-butoxide is alkali, by intermediate
B reacts with equal tribromo-benzene, obtains target product.
The present invention does not have special limitation to the coupling reaction, using coupling reaction well-known to those skilled in the art
, simply, raw material is easy to get the preparation method.
The present invention also provides application of the above-mentioned aromatic amine analog derivative in organic electroluminescence device, virtue of the invention
Fragrant race's amine derivant can be applied as hole mobile material in terms of organic electroluminescence device, the organic electroluminescence
Luminescent device include anode, negative electrode and organic matter layer, organic matter layer comprising hole injection layer, hole transmission layer, electronic barrier layer,
At least one of which in luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer；At least one of which in the organic matter layer
Contain aromatic amine analog derivative described above.The aromatic amine analog derivative can specifically be sent out as organic electroluminescence is prepared
The hole transmission layer of optical device.The device architecture of use is preferably specially：EML is used as luminescent layer material, and 2-TNATA is used as hole
Implanted layer material, described aromatic amine analog derivative is used as hole transmission layer material, is used to manufacture construction same as below
Organic luminescent device：Aromatic amine analog derivative (the 30nm)/BH1 of ITO/2-TNATA (80nm)/described：BD1(30nm)/
Alq3(30nm)/LiF(0.5nm)/Al(60nm).Organic luminescent device of the invention be flat panel show, planar illuminant,
It is the light source of illumination face illuminating OLED illuminator, flexible illuminator, duplicator, printer, LCD backlight lamp or dosing machine class, aobvious
Show that plate, mark etc. are suitable to use.
The present invention has no particular limits to the raw material employed in following examples, can be for commercially available prod or using this
Preparation method known to art personnel is prepared.
Embodiment A：
(A1) preparation of intermediate A 1
By paradibromobenzene (56.3g, 240mmol), benzimidazole is simultaneously<1,2-A>Benzimidazole (31.3g, 180mmol), iodine
Change cuprous (4.6g, 24mmol), potassium carbonate (66.3g, 480mmol) and 18- crown- 6- ethers (2.1g, 8mmol) are placed in nitrogen environment
500mL there-necked flasks in.Afterwards, 8mLDMPU, system 6 hours of stirring reaction at 180 DEG C are added.After being cooled to room temperature, subtract
Press filtration obtains filtrate, and according to watery hydrochloric acid, the order washing filtrate of saturated sodium bicarbonate solution and saturated aqueous common salt, magnesium sulfate is dried
After concentrate, column chromatography obtains crude product (yield is 60%).
Mass spectrum m/z：361.05 (calculated values：361.02).Theoretical elemental content (%) C19H12BrN3：C,63.00；H,
3.34；Br,22.06；N, 11.60 actual measurements constituent content (%)：C,63.03；H,3.32；Br,22.04；N,11.61.Above-mentioned knot
Fruit confirms that it is target product to obtain product.
(A2) preparation of intermediate A 2
Paradibromobenzene in embodiment A1 is replaced with into equimolar Isosorbide-5-Nitrae-dibromine naphthalene, other steps with embodiment A1 phases
Together, intermediate A 2 is obtained.Mass spectrum m/z：411.06 (calculated values：411.04).Theoretical elemental content (%) C23H14BrN3：C,
67.00；H,3.42；Br,19.38；N, 10.19 actual measurements constituent content (%)：C,67.01；H,3.43；Br,19.39；N,
10.17.The above results confirm that it is target product to obtain product.
(A3) preparation of intermediate A 3
Paradibromobenzene in embodiment A1 is replaced with into equimolar Isosorbide-5-Nitrae-deuterated to bromine hexichol, other steps with implementation
A1 is identical for example, obtains intermediate A 3.Mass spectrum m/z：365.06 (calculated values：365.05).Theoretical elemental content (%)
C19H8D4BrN3：C,62.31；H,4.40；Br,21.82；N, 11.47 actual measurements constituent content (%)：C,62.33；H,4.41；Br,
21.81；N,11.45.The above results confirm that it is target product to obtain product.
(A4) preparation of intermediate A 4
Paradibromobenzene in embodiment A1 is replaced with into equimolar 4,4'- '-dibromobiphenyls, other steps are and embodiment
A1 is identical, obtains intermediate A 4.Mass spectrum m/z：437.06 (calculated values：437.05).Theoretical elemental content (%) C25H16BrN3：C,
68.50；H,3.68；Br,18.23；N, 9.59 actual measurements constituent content (%)：C,68.52；H,3.66；Br,18.24；N,9.58.
The above results confirm that it is target product to obtain product.
Embodiment B：
(B1) preparation of intermediate B 1
By tri-butyl phosphine (toluene solution of the 1.0M of 4.4mL, 1.48g, 0.05mmol), palladium (0.4g,
1.83mmol) and sodium tert-butoxide (22.7g, 237mmol) added to intermediate A 1 (66.1g, 183mmol) and aniline (17.8g,
192mmol) the solution in degassed toluene (500mL), and the mixture is heated 2 hours under reflux.The reaction is mixed
Compound is cooled to room temperature, is filtered with dilution with toluene and via diatomite.By filtrate water dilution, and extracted with toluene, and
And merge organic phase, it is evaporated under vacuo.The residue is filtered via silica gel (heptane/dichloromethane),
And crystallized from isopropanol.Obtain intermediate B 1 (54.7g, theoretical value 80%).
Mass spectrum m/z：374.11 (calculated values：374.15).Theoretical elemental content (%) C25H18N4：C,80.19；H,4.85；
N, 14.96 actual measurements constituent content (%)：C,80.18；H,4.86；N,14.96.The above results confirm to obtain product for target is produced
Product.
(B2) preparation of intermediate B 2
Intermediate A 1 in embodiment B1 is replaced with into equimolar intermediate A 2, other steps with embodiment B1 phases
Together, intermediate B 2 is obtained.Mass spectrum m/z：424.16 (calculated values：424.17).Theoretical elemental content (%) C29H20N4：C,82.05；
H,4.75；N, 13.20 actual measurements constituent content (%)：C,82.04；H,4.75；N,13.21.The above results confirm that obtaining product is
Target product.
(B3) preparation of intermediate B 3
Aniline in embodiment B1 is replaced with into equimolar naphthalidine, other steps are identical with embodiment B1, obtain
Intermediate B 3.Mass spectrum m/z：424.16 (calculated values：424.17).Theoretical elemental content (%) C29H20N4：C,82.05；H,4.75；
N, 13.20 actual measurements constituent content (%)：C,82.04；H,4.74；N,13.22.The above results confirm to obtain product for target is produced
Product.
(B4) preparation of intermediate B 4
Aniline in embodiment B1 is replaced with into equimolar benzidine, other steps are identical with embodiment B1, obtain
Intermediate B 4.Mass spectrum m/z：450.16 (calculated values：450.18).Theoretical elemental content (%) C31H22N4：C,82.64；H,4.92；
N, 12.44 actual measurements constituent content (%)：C,82.65；H,4.92；N,12.43.The above results confirm to obtain product for target is produced
Product.
(B5) preparation of intermediate B 5
Aniline in embodiment B1 is replaced with into equimolar 2- naphthylamines, other steps are identical with embodiment B1, obtain
Intermediate B 5.Mass spectrum m/z：424.16 (calculated values：424.17).Theoretical elemental content (%) C29H20N4：C,82.05；H,4.75；
N, 13.20 actual measurements constituent content (%)：C,82.06；H,4.72；N,13.22.The above results confirm to obtain product for target is produced
Product.
(B6) preparation of intermediate B 6
Intermediate A 1 in embodiment B1 is replaced with into equimolar intermediate A 3, other steps with embodiment B1 phases
Together, intermediate B 6 is obtained.Mass spectrum m/z：378.16 (calculated values：378.18).Theoretical elemental content (%) C25H14D4N4：C,
79.34；H,5.86；N, 14.80 actual measurements constituent content (%)：C,79.34；H,5.85；N,14.81.The above results confirm to obtain
Product is target product.
(B7) preparation of intermediate B 7
Intermediate A 1 in embodiment B1 is replaced with into equimolar intermediate A 4, other steps with embodiment B1 phases
Together, intermediate B 7 is obtained.Mass spectrum m/z：378.16 (calculated values：378.18).Theoretical elemental content (%) C31H22N4：C,82.64；
H,4.92；N, 12.44 actual measurements constituent content (%)：C,82.63；H,4.92；N,12.45.The above results confirm that obtaining product is
Target product.
(B8) preparation of intermediate B 8
Aniline in embodiment B1 is replaced with into equimolar p-tert-butyl-aniline, other steps with embodiment B1 phases
Together, intermediate B 8 is obtained.Mass spectrum m/z：430.26 (calculated values：430.22).Theoretical elemental content (%) C29H26N4：C,80.90；
H,6.09；N, 13.01 actual measurements constituent content (%)：C,80.91；H,6.07；N,13.02.The above results confirm that obtaining product is
Target product.
Embodiment C：
(C1) synthesis of compound TM1：
By tri-butyl phosphine (toluene solution of the 1.0M of 4.4mL, 1.48g, 0.05mmol), palladium (0.4g,
1.83mmol) intermediate B 1 (68.4g, 183mmol) and equal tribromo-benzene are added to sodium tert-butoxide (52.7g, 549mmol)
The solution of (59.8g, 192mmol) in degassed toluene (500mL), and the mixture is heated 2 hours under reflux.Should
Reactant mixture is cooled to room temperature, is filtered with dilution with toluene and via diatomite.By filtrate water dilution, and carried with toluene
Take, and merge organic phase, it is evaporated under vacuo.The residue is carried out via silica gel (heptane/dichloromethane)
Filtering, and crystallized from isopropanol.Obtain target product TM1 (142.0g, theoretical value 65%).
Mass spectrum m/z：1194.47 (calculated values：1194.46).Theoretical elemental content (%) C81H54N12：C,81.39；H,
4.55；N, 14.06 actual measurements constituent content (%)：C,81.37；H,4.56；N,14.07.The above results confirm that it is mesh to obtain product
Mark product.
(C2) synthesis of compound TM2：
Intermediate B 1 in embodiment C1 is replaced with into equimolar intermediate B 2, other steps with embodiment C1 phases
Together, intermediate TM2 is obtained.Mass spectrum m/z：1344.56 (calculated values：1344.51).Theoretical elemental content (%) C93H60N12：C,
83.01；H,4.49；N, 12.49 actual measurements constituent content (%)：C,83.03；H,4.48；N,12.49.The above results confirm to obtain
Product is target product.
(C3) synthesis of compound TM3：
Intermediate B 1 in embodiment C1 is replaced with into equimolar intermediate B 3, other steps with embodiment C1 phases
Together, intermediate TM3 is obtained.Mass spectrum m/z：1344.56 (calculated values：1344.51).Theoretical elemental content (%) C93H60N12：C,
83.01；H,4.49；N, 12.49 actual measurements constituent content (%)：C,83.04；H,4.48；N,12.48.The above results confirm to obtain
Product is target product.
(C4) synthesis of compound TM4：
Intermediate B 1 in embodiment C1 is replaced with into equimolar intermediate B 4, other steps with embodiment C1 phases
Together, intermediate TM4 is obtained.Mass spectrum m/z：1422.56 (calculated values：1422.55).Theoretical elemental content (%) C99H66N12：C,
83.52；H,4.67；N, 11.88 actual measurements constituent content (%)：C,83.51；H,4.68；N,11.89.The above results confirm to obtain
Product is target product.
(C5) synthesis of compound TM5：
Intermediate B 1 in embodiment C1 is replaced with into equimolar intermediate B 5, other steps with embodiment C1 phases
Together, intermediate TM5 is obtained.Mass spectrum m/z：1344.50 (calculated values：1344.51).Theoretical elemental content (%) C93H60N12：C,
83.01；H,4.49；N, 12.49 actual measurements constituent content (%)：C,83.03；H,4.49；N,12.48.The above results confirm to obtain
Product is target product.
(C6) synthesis of compound TM6：
Intermediate B 1 in embodiment C1 is replaced with into equimolar intermediate B 6, other steps with embodiment C1 phases
Together, intermediate TM6 is obtained.Mass spectrum m/z：1344.50 (calculated values：1344.51).Theoretical elemental content (%) C81H42D12N12：C,
80.57；H,5.51；N, 13.92 actual measurements constituent content (%)：C,80.56；H,5.52；N,13.92.The above results confirm to obtain
Product is target product.
(C7) synthesis of compound TM7:
Intermediate B 1 in embodiment C1 is replaced with into equimolar intermediate B 7, other steps with embodiment C1 phases
Together, intermediate TM7 is obtained.Mass spectrum m/z：1422.53 (calculated values：1422.55).Theoretical elemental content (%) C99H66N12：C,
83.52；H,4.67；N, 11.81 actual measurements constituent content (%)：C,83.53；H,4.65；N,11.82.The above results confirm to obtain
Product is target product.
(C8) synthesis of compound TM8:
Intermediate B 1 in embodiment C1 is replaced with into equimolar intermediate B 8, other steps with embodiment C1 phases
Together, intermediate TM8 is obtained.Mass spectrum m/z：1362.63 (calculated values：1362.65).Theoretical elemental content (%) C93H78N12：C,
81.91；H,5.77；N, 12.33 actual measurements constituent content (%)：C,81.93；H,5.75；N,12.32.The above results confirm to obtain
Product is target product.
Comparative example 1
EML is used as luminescent layer material, 2-TNATA is used as hole injection layer material, and α-NPD are used as hole transmission layer thing
Matter, is used to manufacture the organic luminescent device of construction same as below：ITO/2-TNATA(80nm)/α-NPD(30nm)/EML
(30nm)/Alq3(30nm)/LiF(0.5nm)/Al(60nm).Ito glass substrate is placed in distilled water and is cleaned 2 times, ultrasonic wave
Washing 30 minutes, is washed 30 minutes in order by isopropanol, acetone, methyl alcohol, cleans 2 times, ultrasonic washing repeatedly with distilled water
10 minutes, dry, be transferred in plasma washing machine, aforesaid substrate is washed 5 minutes, be sent in evaporator.It is accurate
It is deposited with successively on the ito transparent electrode got ready, 2-TANATA is carried out the hole note of formation 80nm thickness after vacuum evaporation first
Enter layer.α-NPD are carried out into vacuum evaporation on hole injection layer, the hole transmission layer of 30nm thickness is formed.Superincumbent hole
BH1 and BD1 is carried out the luminescent layer of formation 25nm after mixing vacuum evaporation in transport layer.Then, by Alq3's on luminescent layer
Compound carries out vacuum evaporation with the thickness of 30nm, forms electron transfer layer.By LiF 0.5nm on electron transfer layer, (electronics is noted
Enter layer) and Al 600nm (negative electrode) successively carry out vacuum evaporation.It should be noted that be, as the LiF of electron injection electrode
WithFilm forming speed formed.Make organic luminescent device, referred to as comparative sample 1
Organic luminescent device is prepared by described aromatic amine analog derivative：
Described aromatic amine analog derivative is replaced α-NPD as the compound in hole transmission layer, with above-mentioned ratio
The method same compared with example 1 has been manufactured and has possessed ITO/2-TNATA (80nm)/for HTL aromatic amines compound (30nm)/BH1：
The organic luminescent device of BD1 (30nm)/Alq3 (30nm)/LiF (0.5nm)/Al (60nm) structure, referred to as sample 1 to 25.
Evaluate example 1：The characteristics of luminescence evaluation of comparative sample 1 and sample 1~8
The organic luminescent device that will be made as above makes it light by direct current driven, determines brightness, electric current
Density, obtains current density 10mA/cm2When current efficiency and driving voltage.Further obtain original intensity 20000cd/m2When
Device lifetime.Form to result table 1 below represents.
Table 1
Result above shows that aromatic amine analog derivative of the invention is applied in organic electroluminescence device, especially
As hole mobile material, high efficiency, long-life advantage are shown, be luminous organic material of good performance.
Obviously, the explanation of above example is only intended to help and understands the method for the present invention and its core concept.Should refer to
Go out, for the those of ordinary skill of the technical field, under the premise without departing from the principles of the invention, can also be to this hair
Bright to carry out some improvement and modification, these are improved and modification is also fallen into the protection domain of the claims in the present invention.
Claims (9)
1. a kind of aromatic amine analog derivative, it is characterised in that structural formula is as shown in formula I：
Wherein, R1、R2The independent substituted or unsubstituted aryl selected from C6~C50, C10~C30 it is substituted or unsubstituted thick
One kind in ring, the substituted or unsubstituted condensed hetero ring of C8~C30.
2. a kind of aromatic amine analog derivative according to claim 1, it is characterised in that R1、R2It is independent selected from C6~C9
Substituted or unsubstituted aryl, the substituted or unsubstituted condensed ring of C10~C14 in one kind.
3. a kind of aromatic amine analog derivative according to claim 1, it is characterised in that R1Appoint selected from following chemical formula
Meaning one：
Wherein, Ra is alkyl, halogen, cyano group, hydroxyl or sulfydryl；
* the connecting key of substitution base and compound is represented.
4. a kind of aromatic amine analog derivative according to claim 1, it is characterised in that R2Appoint selected from following chemical formula
Meaning one：
5. a kind of aromatic amine analog derivative according to claim 1, it is characterised in that the aromatic amine analog derivative
Selected from any one in structure shown in following TM1~TM8：
6. the preparation method of the aromatic amine analog derivative described in any one of claim 1-5, it is characterised in that by following road
Line synthesis obtains the aromatic amine analog derivative：
Wherein, R1、R2The independent substituted or unsubstituted aryl selected from C6~C50, C10~C30 it is substituted or unsubstituted thick
One kind in ring, the substituted or unsubstituted condensed hetero ring of C8~C30.
7. application of the aromatic amine analog derivative described in claim 1-5 any one in organic electroluminescence device.
8. application of the aromatic amine analog derivative according to claim 7 in organic electroluminescence device, its feature exists
In the organic electroluminescence device includes anode, negative electrode and organic matter layer, and Claims 1 to 5 is contained in the organic matter layer
Aromatic amine analog derivative described in any one.
9. application of the aromatic amine analog derivative according to claim 8 in organic electroluminescence device, its feature exists
In the organic layer includes hole transmission layer, and the aromatic amine described in any one of Claims 1 to 5 is contained in hole transmission layer
Analog derivative.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114621102A (en) * | 2022-03-18 | 2022-06-14 | 长春海谱润斯科技股份有限公司 | Arylamine derivative and organic electroluminescent device thereof |
| US12077541B2 (en) | 2018-03-09 | 2024-09-03 | Merck Patent Gmbh | Compounds for electronic devices |
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