CN106187963A - One is containing anthracene compounds and preparation method thereof and a kind of organic luminescent device - Google Patents

One is containing anthracene compounds and preparation method thereof and a kind of organic luminescent device Download PDF

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CN106187963A
CN106187963A CN201610505285.3A CN201610505285A CN106187963A CN 106187963 A CN106187963 A CN 106187963A CN 201610505285 A CN201610505285 A CN 201610505285A CN 106187963 A CN106187963 A CN 106187963A
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substituted
formula
aryl
compounds
containing anthracene
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崔敦洙
高春吉
王辉
马晓宇
赵贺
李明
李文军
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Jilin Optical and Electronic Materials Co Ltd
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    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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Abstract

The invention provides a kind of compounds Han anthracene, there is structure shown in formula I.The present invention is by modifying the compounds structure containing anthracene, so that comprising the organic electroluminescence device containing anthracene compounds shown in formula (I) possess the features such as higher brightness, preferable thermostability, long-life and high efficiency.

Description

One is containing anthracene compounds and preparation method thereof and a kind of organic luminescent device
Technical field
The present invention relates to organic photoelectrical material technical field, particularly relate to a kind of containing anthracene compounds and preparation method thereof with And one organic luminescent device.
Background technology
Organic luminescent device (OLED) is a kind of novel flat panel display device, typically opposed by negative electrode, two, anode Electrode and at least one of which organic luminescent compounds layer composition being inserted between these two electrodes.Specifically by transparent ITO anode, sky Cave implanted layer (TIL), hole transmission layer (HTL), luminescent layer (EL), hole blocking layer (HBL), electron transfer layer (ETL), electronics The negative electrodes such as implanted layer (EIL), LiAl are formed, and can omit 1～2 organic layer on demand.
Forming voltage between two electrodes of organic luminescent device, inject from cathode electronics, another side is noted from anode Enter hole.Above-mentioned electronics and hole are at luminescent layer in conjunction with forming excited state, and excited state returns to stable ground state, makes have fluorescence Or the organic compound of phosphorescent characteristics creates light emission.
The above-mentioned luminescent material that organic compound is organic luminescent device with fluorescence or phosphorescent characteristics, forms luminescence Layer.At present, the forming method of luminescent layer specifically includes that Doping Phosphorus luminescent material (organic metal) in fluorescent host material；Fluorescence master The material doped fluorescence of body (comprising the Organic substance of nitrogen) adulterant；Adulterant (DCM, Rubrene, DCJTB etc.) is utilized in luminous body The method embodying long wavelength.The factors such as emission wavelength, efficiency, driving voltage, life-span are improved by above-mentioned doping method.General shape The material becoming luminescent layer is to have centrosome and benzene, biphenyl, naphthalene, the heterocycles etc. such as benzene, naphthalene, fluorenes, spiral shell two fluorenes, anthracene, pyrene, carbazole to join Body；The replacement of the replacing structures such as para-position, meta, the binding site at ortho position and cyano group, fluorine, methyl, the tert-butyl group can also be passed through.
Summary of the invention
In view of this, the technical problem to be solved in the present invention be to provide one containing anthracene compounds and preparation method thereof with And a kind of organic luminescent device, the described compounds containing anthracene the organic luminescent device prepared have higher luminous efficiency and The longer life-span.
The invention provides a kind of compounds Han anthracene, there is structure shown in formula I:
Wherein:
Y is C or N；
R1For H, substituted or non-substituted C1～60Alkyl, substituted or non-substituted C1～60Alkoxyl, substituted or non-substituted C1～60Ether Base, substituted or non-substituted C6～60Aryl, substituted or non-substituted C6～60Amido, substituted or non-substituted C6～60Aryl amine, replaces or non- Replace C5～60Condensed ring radical, substituted or non-substituted C5～60Heterocyclic radical；
Ar is
n1、n2、n3、n4、n5Independent for 0,1 or 2；
Ar1For H, substituted or non-substituted C1～60Alkyl, substituted or non-substituted C1～60Alkoxyl, substituted or non-substituted C1～60Ether Base, substituted or non-substituted C6～60Aryl, substituted or non-substituted C6～60Amido, substituted or non-substituted C6～60Aryl amine, replaces or non- Replace C5～60Condensed ring radical, substituted or non-substituted C5～60Heterocyclic radical；
R2For substituted or non-substituted C6～60Aryl, substituted or non-substituted C6～60Amido, substituted or non-substituted C6～60Aryl amine, Substituted or non-substituted C5～60Condensed ring radical, substituted or non-substituted C5～60Heterocyclic radical.
Preferably, described Ar1Selected from H, substituted or non-substituted C6～20Aryl, substituted or non-substituted C5～20Heteroaryl, Substituted or non-substituted C6～20Aryl amine.
Preferably, described Ar1Selected from H, substituted or non-substituted phenyl, substituted or non-substituted xenyl, replace or non- Substituted naphthyl, substituted or non-substituted pyridine radicals, substituted or non-substituted hexichol amido, or following any structure:
Wherein,
R3、R4、R5Independent selected from H, substituted or non-substituted C1～60Alkyl, substituted or non-substituted C1～60Alkoxyl, replace or Non-substituted C1～60Ether, substituted or non-substituted C6～60Aryl, substituted or non-substituted C6～60Amido, substituted or non-substituted C5～60Condensed ring Base, substituted or non-substituted C5～60Heterocyclic radical.
Preferably, described containing anthracene compounds, there is structure shown in formula II:
N is 0,1 or 2；
Ar2For substituted or non-substituted C6～30Aryl.
Preferably, described R1For H, substituted or non-substituted C1～10Alkyl, substituted or non-substituted C1～10Alkoxyl.
Preferably, the described compounds containing anthracene has a following any structure:
Present invention also offers the preparation method containing anthracene compounds shown in a kind of formula I, including:
By the boronic acid compounds shown in formula III, carry out substitution reaction with the bromide shown in formula IV or formula (V), To shown in formula I containing anthracene compounds；
Ar-Br formula IV；Br-Ar-Br formula (V)；
Or the bromide shown in the formula of employing (VI), carries out replacing instead with the boronic acid compounds shown in formula (VII) or formula (VIII) Should, obtain shown in formula I containing anthracene compounds；
Ar-B(OH)2Formula (VII)；B(OH)2-Ar-B(OH)2Formula (VIII)；
Wherein:
Y is C or N；
R1For H, substituted or non-substituted C1～60Alkyl, substituted or non-substituted C1～60Alkoxyl, substituted or non-substituted C1～60Ether Base, substituted or non-substituted C6～60Aryl, substituted or non-substituted C6～60Amido, substituted or non-substituted C6～60Aryl amine, replaces or non- Replace C5～60Condensed ring radical, substituted or non-substituted C5～60Heterocyclic radical；
Ar is
N independence for 0,1 or 2；
Ar1For H, substituted or non-substituted C1～60Alkyl, substituted or non-substituted C1～60Alkoxyl, substituted or non-substituted C1～60Ether Base, substituted or non-substituted C6～60Aryl, substituted or non-substituted C6～60Amido, substituted or non-substituted C6～60Aryl amine, replaces or non- Replace C5～60Condensed ring radical, substituted or non-substituted C5～60Heterocyclic radical；
R2For substituted or non-substituted C6～60Aryl, substituted or non-substituted C6～60Amido, substituted or non-substituted C6～60Aryl amine, Substituted or non-substituted C5～60Condensed ring radical, substituted or non-substituted C5～60Heterocyclic radical.
Present invention also offers a kind of organic luminescent device, prepare containing anthracene compounds or above-mentioned preparation method including above-mentioned Containing anthracene compounds.
Described organic luminescent device, preferably includes the first electrode, the second electrode and is arranged at described first electrode and second Organic compound layer between electrode；Described organic compound layer includes above-mentioned preparing containing anthracene compounds or above-mentioned preparation method Containing anthracene compounds.
Present invention also offers a kind of organic photoelectrical material, prepare including above-mentioned heteroaromatic compounds or above-mentioned preparation method Heteroaromatic compounds；Described organic photoelectrical material includes organic photovoltaic cell, Electronic Paper, Organophotoreceptor or organic crystal Pipe.
Compared with prior art, the invention provides a kind of compounds Han anthracene, there is structure shown in formula I.The present invention By the compounds structure containing anthracene is modified, send out so that comprising the organic electroluminescence containing anthracene compounds shown in formula (I) Optical device possesses the features such as higher brightness, preferable thermostability, long-life and high efficiency.
Detailed description of the invention
The invention provides a kind of compounds Han anthracene, there is structure shown in formula I:
Wherein:
Y is C or N；
R1For H, substituted or non-substituted C1～60Alkyl, substituted or non-substituted C1～60Alkoxyl, substituted or non-substituted C1～60Ether Base, substituted or non-substituted C6～60Aryl, substituted or non-substituted C6～60Amido, substituted or non-substituted C6～60Aryl amine, replaces or non- Replace C5～60Condensed ring radical, substituted or non-substituted C5～60Heterocyclic radical；More preferably H, substituted or non-substituted C1～10Alkyl, replaces or non- Replace C1～10Alkoxyl；More preferably H, substituted or non-substituted C1～6Alkyl, substituted or non-substituted C1～6Alkoxyl；In the present invention Some specific embodiment in, it is methyl, ethyl, propyl group, isopropyl, methoxyl group, ethyoxyl.
Ar is
Wherein, the link position of phenyl can be ortho position, meta or para position；The link position of naphthyl can be at same benzene Ortho position on ring, meta or para position, it is also possible on different phenyl ring, can be that α position connects, or β position connects.
Above-mentioned phenyl, naphthyl, anthryl, phenanthryl, the order of connection of pyrenyl do not limit.
Described n1、n2、n3、n4、n5Independent for 0,1 or 2.
Ar1It is preferably H, substituted or non-substituted C1～60Alkyl, substituted or non-substituted C1～60Alkoxyl, substituted or non-substituted C1～60Ether, substituted or non-substituted C6～60Aryl, substituted or non-substituted C6～60Amido, substituted or non-substituted C6～60Aryl amine, takes Generation or non-substituted C5～60Condensed ring radical, substituted or non-substituted C5～60Heterocyclic radical；More preferably H, substituted or non-substituted C6～20Aryl, Substituted or non-substituted C5～20Heteroaryl, substituted or non-substituted C6～20Aryl amine；More preferably H, substituted or non-substituted phenyl, Substituted or non-substituted xenyl, substituted or non-substituted naphthyl, substituted or non-substituted pyridine radicals, substituted or non-substituted two Anilino-, or following any structure:
Described R3、R4、R5Independent selected from H, substituted or non-substituted C1～60Alkyl, substituted or non-substituted C1～60Alkoxyl, takes Generation or non-substituted C1～60Ether, substituted or non-substituted C6～60Aryl, substituted or non-substituted C6～60Amido, substituted or non-substituted C5～60 Condensed ring radical, substituted or non-substituted C5～60Heterocyclic radical.
R3More preferably H, substituted or non-substituted C1～10Alkyl, substituted or non-substituted C1～10Alkoxyl；It is more preferably H, takes Generation or non-substituted C1～6Alkyl, substituted or non-substituted C1～6Alkoxyl；In some embodiments of the invention, its be methyl, Ethyl, propyl group, isopropyl, methoxyl group, ethyoxyl.
R4、R5More preferably H, substituted or non-substituted C6～20Aryl, substituted or non-substituted C5～20Heteroaryl；More preferably For H, substituted or non-substituted phenyl, substituted or non-substituted xenyl, substituted or non-substituted naphthyl, substituted or non-substituted Pyridine radicals.
Above-mentioned aryl, the substituent group of heteroaryl are preferably C1～60Alkyl, C1～60Alkoxyl, C1～60Ether, C6～60Aryl, C6～60Amido, C5～60Condensed ring radical or C5～60Heterocyclic radical；More preferably C1～10Alkyl, C1～10Alkoxyl；More preferably C1～6Alkyl or C1～6Alkoxyl；In some embodiments of the invention, above-mentioned substituent group is methyl, ethyl, propyl group, isopropyl, methoxy Base, ethyoxyl.
R2It is preferably substituted or non-substituted C6～60Aryl, substituted or non-substituted C6～60Amido, substituted or non-substituted C6～60Virtue Amido, substituted or non-substituted C5～60Condensed ring radical, substituted or non-substituted C5～60Heterocyclic radical；The most substituted or non-substituted C6～20 Aryl, substituted or non-substituted C5～20Heteroaryl；More preferably H, substituted or non-substituted phenyl, substituted or non-substituted biphenyl Base, substituted or non-substituted naphthyl, substituted or non-substituted pyridine radicals.
Above-mentioned aryl, amido, aryl amine, condensed ring radical, heterocyclic radical, the substituent group of heteroaryl are preferably C1～60Alkyl, C1～60 Alkoxyl, C1～60Ether, C6～60Aryl, C6～60Amido, C5～60Condensed ring radical or C5～60Heterocyclic radical；More preferably C1～10Alkyl, C1～10Alkoxyl；More preferably C1～6Alkyl or C1～6Alkoxyl；In some embodiments of the invention, above-mentioned substituent group For methyl, ethyl, propyl group, isopropyl, methoxyl group, ethyoxyl.
Currently preferred, described containing anthracene compounds, there is structure shown in formula II:
Ar2It is preferably substituted or non-substituted C6～30Aryl, the most substituted or non-substituted phenyl, replace or non-take The xenyl in generation, substituted or non-substituted phenyl napthyl, substituted or non-substituted phenanthryl, substituted or non-substituted benzo phenanthryl, Substituted or non-substituted pyrenyl, substituted or non-substituted carbazyl, substituted or non-substituted benzofuranyl.More preferably phenyl Or xenyl.
Described phenyl napthyl structure is as follows:
The structure of described benzo phenanthryl is as follows:
N is preferably 0,1 or 2.
When n is 0 or 2, described is symmetrical structure containing anthracene compounds.
When n is 1, as described Ar2The phenyl connected for para-positionOr on same phenyl ring α position is even The naphthyl connectOr the naphthyl that on difference phenyl ring, β position connectsOr symmetry is even The phenanthryl connectDuring Deng symmetric group, institute Stating containing anthracene compounds is symmetrical structure.
Described R1With the scope of Y ibid, do not repeat them here.
Currently preferred, the described compounds containing anthracene has a following any structure:
Present invention also offers the above-mentioned preparation method containing anthracene compounds, including:
By the boronic acid compounds shown in formula III, carry out substitution reaction with the bromide shown in formula IV or formula (V), To shown in formula I containing anthracene compounds；
Ar-Br formula IV；Br-Ar-Br formula (V).
Described reaction is preferably carried out under the catalytic action of catalyst tetra-triphenylphosphine palladium.The solvent of described reaction is preferably Toluene.The temperature of described reaction is preferably 80～100 DEG C, and the response time is preferably 8～12h.
After reaction terminates, it is preferred to use the method crossing post separation obtains pure product.
The present invention can also be by using the bromide shown in formula (VI), with the boric acid chemical combination shown in formula (VII) or formula (VIII) Thing carries out substitution reaction, obtain shown in formula I containing anthracene compounds.
Ar-B(OH)2Formula (VII)；B(OH)2-Ar-B(OH)2Formula (VIII).
Reaction condition ibid, does not repeats them here.
Compound shown in above-mentioned formula (VI) is preferably prepared by the following method and obtains:
Compound shown in formula (a) is carried out substitution reaction with dibromide shown in formula (b), obtains compound shown in formula (c)；
Described reaction is preferably carried out under the catalytic action of sodium hydride.
The solvent of described reaction is preferably oxolane.
The temperature of described reaction is preferably room temperature, and the response time is preferably 8～12h.
After reaction terminates, it is preferred to use the method crossing post separation obtains pure product.
Then compound shown in formula (c) carries out Norfloxacin Reaction, obtains compound shown in formula (d)；
Described Norfloxacin Reaction is 1, and 8-diazabicylo 11 carbon-7-alkene (DBU), palladium, tri-butyl phosphine exists Under the conditions of carry out.
The solvent of described reaction is preferably toluene or dimethylbenzene.The temperature of described reaction is preferably 100～160 DEG C, described The time of reaction is preferably 10～20h.
After reaction terminates, it is preferred that add water extraction, and organic facies toluene carries out recrystallization, obtains product.
Shown in formula (d), compound reacts with triisopropyl borate ester, obtains boronic acid compounds shown in formula (f)；
Described reaction is preferably carried out under the catalytic action of n-BuLi.
The solvent of described reaction is preferably oxolane.
In described reaction, compound shown in formula (d) is preferably-78 with the mixing temperature of triisopropyl borate ester, n-BuLi DEG C, after dropping, reaction temperature is preferably room temperature, and the response time is preferably 8～12h.
After reaction terminates, it is preferred that the cancellation that adds water is reacted, and extracts and is evaporated and obtains product.
In the present invention, the preparation method containing anthracene compounds shown in formula I is not limited to said method, art technology Personnel can be according to above reaction unrestricted choice reactive group, such as:
Use boronic acid compounds shown in formula III, and Isosorbide-5-Nitrae-dibromobenzene reaction, obtain compound shown in formula (A), the most again React with boronic acid compounds shown in formula (B), obtain shown in formula I containing anthracene compounds.
Those skilled in the art can deduce its preparation method according to product structure and above-mentioned reaction method.
Above-mentioned reaction condition ibid, does not repeats them here.
In above-mentioned reaction raw materials and product structure, Y, Ar, R1Scope ibid, do not repeat them here.
The compounds preparation method containing anthracene that the present invention provides is simple, it is easy to industrialization.
Present invention also offers a kind of organic luminescent device, including shown in above-mentioned formula (I) containing anthracene compounds.
The organic luminescent device that described organic luminescent device is well known to those skilled in the art, present invention preferably comprises First electrode, the second electrode and the organic matter layer being arranged between described first electrode and the second electrode；Described organic matter layer bag Containing above-mentioned containing anthracene compounds.Described can be single form containing anthracene compounds, or mixes with other materials, is contained in State in organic matter layer.
In the present invention, it is whole that described organic matter layer refers between organic electroluminescence device the first electrode and the second electrode Layer.At least one of which in described organic matter layer is luminescent layer.
According to the present invention, described organic matter layer preferably include hole injection layer, hole transmission layer, not only possess hole inject but also Possess hole transport technical ability layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer and both possessed Electric transmission possesses again one or more layers in electronics injection technical ability layer, more preferably includes hole injection layer, the sky set gradually Cave transport layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer and electron injecting layer or the both tools set gradually Standby hole inject possess again hole transport technical ability layer, electronic barrier layer, luminescent layer, hole blocking layer and not only possessed electric transmission but also Possess electronics and inject technical ability layer.
When organic matter layer of the present invention comprises hole injection layer, hole transmission layer or not only possesses hole injection but also possess hole biography During defeated technical ability layer, the most described hole injection layer, hole transmission layer or not only possessed hole and inject but also possess hole transport technical ability layer Middle at least one of which comprises hole injecting material, hole transporting material or not only possesses hole injection but also possess the thing of hole transport technical ability Matter.
When organic matter layer of the present invention is single layer structure, described organic matter layer is luminescent layer, when described organic matter layer is many During Rotating fields, described organic matter layer includes luminescent layer；Preferably include phosphorescence host in described luminescent layer, fluorescent host, phosphorescence are mixed Miscellaneous material and one or more in fluorescence dopant material；Described phosphorescence host, fluorescent host, phosphorescence dopant material are mixed with fluorescence One or more in miscellaneous material for shown in formula (I) containing anthracene compounds.
Described luminescent layer is the most preferably red, yellow or cyan luminescent layer, and described is red, yellow containing anthracene compounds Or the main body of cyan luminescent layer or dopant.As, when described luminescent layer is cyan luminescent layer, containing shown in described formula (I) Anthracene compounds is when adulterating for cyan main body or cyan, it is possible to provide high efficiency, high brightness, high-resolution and long-life have Machine luminescent device.
When described organic matter layer includes electron transfer layer, described electron transfer layer can include shown in formula (I) containing anthracene class Compound and/or metallic compound.The material for electric transmission that described metallic compound is well known to those skilled in the art , there is no special restriction.
When described organic matter layer includes luminescent layer and electron transfer layer simultaneously, described luminescent layer can divide with electron transfer layer Shown in the formula (I) not including that structure is identical or differ containing anthracene compounds.
The present invention provide organic electroluminescence device, utilize shown in formula (I) containing anthracene compounds and conventional material system Become, the present invention to the preparation method of described organic electroluminescence device indefinite, this area conventional method, this Bright preferably by methods such as film vapor deposition, electron beam evaporation or physical vapour deposition (PVD)s on substrate evaporation metal and there is electric conductivity Oxide and their alloy formed anode, be then formed on organic matter layer and evaporation cathode, obtain organic electroluminescence and send out Optical device.
Organic matter layer, anode material are deposited with cathode substance layer on outer substrate by the present invention in order, make organic light emission Device.
Described organic matter layer can include above-mentioned hole injection layer, hole transmission layer, luminescent layer, hole blocking layer simultaneously And the multiple structure of electron transfer layer, and these multiple structures can be according to above-mentioned film vapor deposition, electron beam evaporation or physics gas The method such as deposition evaporation mutually, it is possible to use various macromolecular material solvent engineering substitutes evaporation coating method, such as spin-coating (spin-coating), strip molding (tape-casting), scraping blade method (doctor-blading), silk screen printing (Screen- Printing), the method such as ink jet printing or thermal imaging (Thermal-Imaging) reduces number of plies manufacture.
The organic electroluminescence device that the present invention provides according to the material used also can be divided into above luminous, back side illuminated or Lighting at two sides；And this organic electroluminescence device can be applied at organic luminescent device (OLED), organic sun with same principle On battery (OSC), Electronic Paper (e-paper), Organophotoreceptor (OPC) or OTFT (OTFT).
Shown in the formula (I) that the present invention provides containing anthracene compounds in organic photovoltaic cell, illumination by OLED, flexibility The organic assemblies such as OLED, Organophotoreceptor and organic transistor also can be suitable for according to the principle being suitable for organic luminescent device.
Present invention also offers a kind of organic photoelectrical material, including shown in above-mentioned formula (I) containing anthracene compounds；Described have Machine photoelectric material includes organic photovoltaic cell, Electronic Paper, Organophotoreceptor or organic transistor.
In order to further illustrate the present invention, below in conjunction with embodiment the present invention is provided containing anthracene compounds and preparation thereof Method and a kind of organic luminescent device are described in detail.
Embodiment 1
The synthesis of the bromo-2-of intermediate 1,3-bis-(2-cumene epoxide) benzene (A-1)
Taking 2-isopropyl-phenol 0.1mol, be dissolved in 100mL anhydrous tetrahydro furan, stirring, precise 0.4mol hydrogenates Sodium is added in reaction bulb in batches, the fastest, prevents too many bubble from producing, adds rear solution and present yellow, add 1,3- Two bromo-2-fluorobenzene 0.11mol, to be also dividedly in some parts, and room temperature reaction is overnight.
The product obtained being filtered, remove solid matter, filtrate is spin-dried for, and adds dichloromethane and dissolves, crosses post stone Oil ether: ethyl acetate=1:5 (volume ratio) rushes post, obtains 1, the bromo-2-of 3-bis-(2-cumene epoxide) benzene (intermediate A-1) (0.05mol, y=50%).
Embodiment 2
Intermediate A-2～the synthesis of A-15
According to the preparation method of above-mentioned intermediate A-1, use raw material as shown in table 1 below, obtain the compound shown in table 1.
Table 1 embodiment 2 reacting substance, generation material and productivity collect
The synthesis of embodiment 3 intermediate 4-bromo-6-isopropyl diphenyl also [b, d] furan (B-1)
Under nitrogen protective condition, the there-necked flask of 500ml, add 1, the bromo-2-of 3-bis-(2-cumene epoxide) benzene 0.1mmol, 1,8-diazabicylo 11 carbon-7-alkene (DBU) 0.11mmol, palladium 0.003mmol, tri-butyl phosphine After 0.025mmol, xylene solution 200ml add, heating-up temperature to 140 DEG C, react 18 hours, obtain reactant liquor；Institute State and extract after reactant liquor adds water, separatory, will obtain after organic facies concentrates with re crystallization from toluene, obtain 4-bromo-6-isopropyl Dibenzo [b, d] furan (intermediate B-1), productivity 48%, reaction conversion ratio 100%.
Embodiment 4 intermediate B-2～the synthesis of B-15:
According to the preparation method of above-mentioned intermediate B-1, use raw material as shown in table 2 below, prepare chemical combination shown in table 2 Thing.
Table 2 embodiment 4 reacting substance, generation material and productivity collect
The synthesis of embodiment 5 intermediate 6-isopropyl diphenyl also [b, d] furan-4-ylboronic acid (C-1)
0.018mol intermediate product B-1 is dissolved in 100ml, in dry THF, is subsequently adding dried 500ml tri- In mouth bottle, N2Under protection ,-78 DEG C of reaction 30min, are slowly added dropwise n-BuLi 0.027mol, keep-78 DEG C instead after completion of dropwise addition Answer 3h, then be slowly added dropwise triisopropyl borate ester 0.02mol, after completion of dropwise addition, reaction is maintained at-78 DEG C of reaction 2h, slowly heats up To room temperature, overnight, after TLC monitoring reaction terminates, with water slow cancellation reactant liquor, extraction is evaporated (6-isopropyl diphenyl in reaction And [b, d] furan-4-base) boric acid (C-1) 0.0144mol, productivity is 80%.Mass spectrum: 254.08.
The synthesis of embodiment 6 intermediate C-2～C-16
According to the preparation method of above-mentioned intermediate C-1, use raw material as shown in table 3 below, obtain the compound shown in table 3.
Table 3 embodiment 6 reacting substance, generation material and productivity collect
The synthesis of embodiment 7 intermediate 4-(10-bromine anthracene-9-base)-6-isopropyl diphenyl also [b, d] furan (D-1)
By (6-isopropyl diphenyl also [b, d] furan-4-base) boric acid 0.20mol, 9,10-dibromoanthracene 0.10mol and four or three Phenylphosphine palladium 7.0g joins in reaction bulb, adds toluene 600mL, aqueous sodium carbonate (2N, 250mL), in the protection of nitrogen Lower oil bath 90 DEG C is reacted, overnight.By reacted system cooling, separatory, it is spin-dried for toluene, the residue dichloro that will obtain Methane is the most molten, adds the petroleum ether of equivalent, crosses silica gel funnel, and rinses with dichloromethane: petroleum ether=1:2 (volume ratio), Until product-free point flows out, collect filtrate, and be spin-dried for solvent, obtain 4-(10-bromine anthracene-9-base)-6-isopropyl diphenyl also [b, d] Furan (intermediate D-1) (0.081mol, y=81%).Mass spectrum: 465.37.
The synthesis of embodiment 8 intermediate D-2～D-26
According to the preparation method of above-mentioned intermediate D-1, use raw material as shown in table 4 below, prepare chemical combination shown in table 4 Thing.
Table 4 embodiment 8 reacting substance, generation material and productivity collect
The synthesis of the bromo-N of embodiment 9 intermediate 7-, N-diphenyl triphenyl alkene-2-amine (D-27)
By diphenylamine 0.10mol and sodium tert-butoxide 0.30mol, toluene 400mL joins in reaction bulb, stirs 30 points Clock, nitrogen protects, is subsequently adding 2,7-dibromo benzophenanthrene 0.12mol, three (dibenzylideneacetone) two palladium 1.5g, is eventually adding three Tert-butyl group phosphine 4g, is warmed up to 100 DEG C and reacts 24 hours.
The system cooling that will obtain, adds water and terminates reaction, filter, the filtrate separatory that will obtain, be spin-dried for toluene, adds few Amount dichloromethane dissolved solid, uses petroleum ether: dichloromethane=3:1 (volume ratio) to cross post and separates, obtain amines D-27 (0.05mol, y=50%).Mass spectrum: 474.38.
The synthesis of embodiment 10 intermediate D28～D-32
According to the preparation method of above-mentioned intermediate D-27, use raw material as shown in table 5 below, prepare chemical combination shown in table 5 Thing.
Table 5 embodiment 10 reacting substance, generation material and productivity collect
Embodiment 11 intermediate E-1～the synthesis of E-19
According to the preparation method of above-mentioned intermediate C-1, use raw material as shown in table 6 below, obtain the compound shown in table 6.
Table 6 embodiment 11 reacting substance, generation material and productivity collect
The synthesis of embodiment 12 intermediate F-1～F-34
According to the preparation method of above-mentioned intermediate D-1, use raw material as shown in table 7 below, prepare chemical combination shown in table 7 Thing.
Table 7 embodiment 12 reacting substance, generation material and productivity collect
Embodiment 13G-1～the synthesis of G-22
According to the preparation method of above-mentioned intermediate C-1, use raw material as shown in table 8 below, prepare chemical combination shown in table 8 Thing.
Table 8 embodiment 13 reacting substance, generation material and productivity collect
The synthesis of embodiment 14 (H-1～H-48)
According to the preparation method of above-mentioned intermediate D-1, use raw material as shown in table 9 below, according to mole about 2:1 or 1:1 prepares compound shown in table 9.
By 6-bromobenzofuran also [3,2-c] pyridine 0.20mol, 9,10-hypoboric acid base anthracene 0.10mol and four triphenylphosphines Palladium 7.0g joins in reaction bulb, adds toluene 600mL, aqueous sodium carbonate (2N, 250mL), oil bath under the protection of nitrogen 90 DEG C are reacted, overnight.By reacted system cooling, separatory, it is spin-dried for toluene, by complete for the residue dichloromethane obtained Molten, add the petroleum ether of equivalent, cross silica gel funnel, and rinse with dichloromethane: petroleum ether=1:2 (volume ratio), until nothing Product point flows out, and collects filtrate, and is spin-dried for solvent, obtains 9,10-bis-(benzofuran also [3,2-c] pyridine-6-base) anthracene (target Product H-1) (0.081mol, y=81%).Mass spectrometry value: 512.55.
According to the preparation method of above-mentioned intermediate D-1, use raw material as shown in table 9 below, prepare chemical combination shown in table 9 Thing.
Table 9 embodiment 14 reacting substance, generation material and productivity collect
Prepared by embodiment 15 luminescent device
By Fisher Co., Ltd's coating layer thickness it isIto glass substrate be placed in distilled water cleaning 2 times, ultrasound wave is washed Washing 30 minutes, then repeatedly clean with distilled water 2 times, ultrasonic washing 10 minutes, distilled water cleans after terminating, uses isopropyl Alcohol, acetone, methanol ultrasonic washing in order, is then dried, and transfers in plasma washing machine, and aforesaid substrate is washed 5 Minute, deliver in evaporator.The ito transparent electrode being already prepared to is deposited with hole injection layer 2-TNATA evaporation successivelyHole transmission layer a-NPD (N, N '-two (1-naphthyl)-N, N'-diphenyl-(1,1 '-xenyl)-4,4'-diamidogen) is deposited withCompound shown in ADN (9,10-bis-(2-naphthyl) anthracene) and the table 10 of 5%, evaporation thickness isHole blocking layer and Hole transmission layer TPBi evaporation thickness isNegative electrode is that LiF evaporation thickness is Anode is that Al evaporation thickness isSaid process organic matter vaporization plating speed keepsThe evaporation rate of LiF isThe evaporation rate of Al is
The electron luminescence characteristic of the organic luminescent device that said method obtains is shown in Table 10, and table 10 is made for the embodiment of the present invention 15 The characteristics of luminescence test result of standby luminescent device.
The characteristics of luminescence test result of the luminescent device of table 10 embodiment of the present invention 15 preparation
From above-mentioned table 10 result, it can be seen that the present invention uses new anthracene derivative to prepare luminescent device, its luminous effect Rate and life characteristic all increase significantly.
The present invention is to utilize new heterocyclic ligand to prepare organic luminescent device, can improve luminescent device luminous efficiency and Life-span, so the present invention has higher practicality in OLED industry.Organic luminescent device prepared by the present invention, may be used for Flat panel shows, planar illuminant, illumination face illuminating OLED luminous body, flexible luminous body, photocopier, printer, the LCD back of the body The fields such as light modulation or the light source of dosing machine class, display panel, mark.
The explanation of above example is only intended to help to understand method and the core concept thereof of the present invention.It is right to it should be pointed out that, For those skilled in the art, under the premise without departing from the principles of the invention, it is also possible to the present invention is carried out Some improvement and modification, these improve and modify in the protection domain also falling into the claims in the present invention.

Claims (10)

1. a compounds Han anthracene, has a structure shown in formula I:
Wherein:
Y is C or N；
R1For H, substituted or non-substituted C1～60Alkyl, substituted or non-substituted C1～60Alkoxyl, substituted or non-substituted C1～60Ether, takes Generation or non-substituted C6～60Aryl, substituted or non-substituted C6～60Amido, substituted or non-substituted C6～60Aryl amine, substituted or non-substituted C5～60Condensed ring radical, substituted or non-substituted C5～60Heterocyclic radical；
Ar is
n1、n2、n3、n4、n5Independent for 0,1 or 2；
Ar1For H, substituted or non-substituted C1～60Alkyl, substituted or non-substituted C1～60Alkoxyl, substituted or non-substituted C1～60Ether, takes Generation or non-substituted C6～60Aryl, substituted or non-substituted C6～60Amido, substituted or non-substituted C6～60Aryl amine, substituted or non-substituted C5～60Condensed ring radical, substituted or non-substituted C5～60Heterocyclic radical；
R2For substituted or non-substituted C6～60Aryl, substituted or non-substituted C6～60Amido, substituted or non-substituted C6～60Aryl amine, replaces Or non-substituted C5～60Condensed ring radical, substituted or non-substituted C5～60Heterocyclic radical.
The most according to claim 1 containing anthracene compounds, it is characterised in that described Ar1Selected from H, substituted or non-substituted C6～20Aryl, substituted or non-substituted C5～20Heteroaryl, substituted or non-substituted C6～20Aryl amine.
The most according to claim 2 containing anthracene compounds, it is characterised in that described Ar1Selected from H, substituted or non-substituted benzene Base, substituted or non-substituted xenyl, substituted or non-substituted naphthyl, substituted or non-substituted pyridine radicals, substituted or non-substituted Hexichol amido, or following any structure:
Wherein,
R3、R4、R5Independent selected from H, substituted or non-substituted C1～60Alkyl, substituted or non-substituted C1～60Alkoxyl, replaces or non-takes For C1～60Ether, substituted or non-substituted C6～60Aryl, substituted or non-substituted C6～60Amido, substituted or non-substituted C5～60Condensed ring radical, Substituted or non-substituted C5～60Heterocyclic radical.
The most according to claim 1 containing anthracene compounds, it is characterised in that described containing anthracene compounds, there is formula II Shown structure:
N is 0,1 or 2；
Ar2For substituted or non-substituted C6～30Aryl.
The most according to claim 1 containing anthracene compounds, it is characterised in that described R1For H, substituted or non-substituted C1～10Alkane Base, substituted or non-substituted C1～10Alkoxyl.
The most according to claim 1 containing anthracene compounds, it is characterised in that the described compounds containing anthracene has following arbitrary Structure:
7. shown in formula I, contain a preparation method for anthracene compounds, including:
By the boronic acid compounds shown in formula III, carry out substitution reaction with the bromide shown in formula IV or formula (V), obtain formula (I) shown in containing anthracene compounds；
Ar-Br formula IV；Br-Ar-Br formula (V)；
Or the bromide shown in employing formula VI, carries out substitution reaction with the boronic acid compounds shown in formula (VII) or formula (VIII), Obtain shown in formula I containing anthracene compounds；
Ar-B(OH)2Formula (VII)；B(OH)2-Ar-B(OH)2Formula (VIII)；
Wherein:
Y is C or N；
R1For H, substituted or non-substituted C1～60Alkyl, substituted or non-substituted C1～60Alkoxyl, substituted or non-substituted C1～60Ether, takes Generation or non-substituted C6～60Aryl, substituted or non-substituted C6～60Amido, substituted or non-substituted C6～60Aryl amine, substituted or non-substituted C5～60Condensed ring radical, substituted or non-substituted C5～60Heterocyclic radical；
Ar is
N independence for 0,1 or 2；
Ar1For H, substituted or non-substituted C1～60Alkyl, substituted or non-substituted C1～60Alkoxyl, substituted or non-substituted C1～60Ether, takes Generation or non-substituted C6～60Aryl, substituted or non-substituted C6～60Amido, substituted or non-substituted C6～60Aryl amine, substituted or non-substituted C5～60Condensed ring radical, substituted or non-substituted C5～60Heterocyclic radical；
R2For substituted or non-substituted C6～60Aryl, substituted or non-substituted C6～60Amido, substituted or non-substituted C6～60Aryl amine, replaces Or non-substituted C5～60Condensed ring radical, substituted or non-substituted C5～60Heterocyclic radical.
8. an organic luminescent device, including described in claim 1～6 any one containing anthracene compounds or claim 7 Described preparation method prepare containing anthracene compounds.
Organic luminescent device the most according to claim 8, it is characterised in that include the first electrode, the second electrode and setting Organic compound layer between described first electrode and the second electrode；Described organic compound layer includes claim 1～6 Anticipate one described containing the preparation method described in anthracene compounds or claim 7 prepare containing anthracene compounds.
10. an organic photoelectrical material, it is characterised in that include the heteroaromatic compounds described in claim 1～6 any one Or heteroaromatic compounds prepared by the preparation method described in claim 7；Described organic photoelectrical material include organic photovoltaic cell, Electronic Paper, Organophotoreceptor or organic transistor.
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Application publication date: 20161207