CN106588592A - Dianthranide derivative, preparation method, and application thereof - Google Patents

Dianthranide derivative, preparation method, and application thereof Download PDF

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Publication number
CN106588592A
CN106588592A CN201611007921.6A CN201611007921A CN106588592A CN 106588592 A CN106588592 A CN 106588592A CN 201611007921 A CN201611007921 A CN 201611007921A CN 106588592 A CN106588592 A CN 106588592A
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aryl
formula
heterocyclic radical
condensed ring
dianthranide
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崔敦洙
李明
秦翠英
姜志远
毕岩
高春吉
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Jilin Optical and Electronic Materials Co Ltd
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Jilin Optical and Electronic Materials Co Ltd
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Priority to CN201611007921.6A priority Critical patent/CN106588592A/en
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Abstract

The invention provides a dianthranide derivative, of which the structure is represented as the formula (I) or (II). In the dianthranide derivative, different groups are introduced to a dianthranide compound to form an asymmetric structure, thereby improving stereoscopic effect and regulating wavelength of the dianthranide derivative. In addition, by regulating the molecular weight of Ar2 and the types of R1 and R3, the material is improved in performances. Furthermore, an organic device using the dianthranide derivative has high brightness, high heat resistance, long service life and high efficiency.

Description

A kind of dianthranide derivant and its preparation method and application
Technical field
The invention belongs to electroluminescent organic material technical field, and in particular to a kind of dianthranide derivant and preparation method thereof And application.
Background technology
General organic luminescent device (OLED) is by the organic matter layer structure inserted between negative electrode, anode and negative electrode and anode Into, the composition of device is transparent ITO anode, hole injection layer (TIL), hole transmission layer (HTL), luminescent layer (EL, hole resistance The negative electrodes such as barrier (HBL), electron transfer layer (ETL), electron injecting layer (EIL), LiAl are formed, and can omit 1～2 on demand organic Layer.Voltage is formed between two electrodes of device while from cathode electronics injection another side anode injection hole.This electronics and sky Cave returns to stable ground state in conjunction with excited state, excited state is formed in luminescent layer.Luminescent material is divided into fluorescent material and phosphorescence material Material, the forming method of luminescent layer is the method and fluorescent host material of doping phosphor material (organic metal) in fluorescent host material Dopant (DCM, Rubrene, DCJTB etc.) is utilized in the method and luminous body of doping fluorescent (Organic substance comprising nitrogen) dopant The method of the existing long wavelength of tool, improves emission wavelength by such mixing, efficiency, driving voltage, the factor such as life-span.Generally form Emitting layer material is with parts such as centrosome and benzene, biphenyl, naphthalene, heterocycle such as benzene, naphthalene, fluorenes, two fluorenes of spiral shell, anthracene, pyrene, carbazoles；It is right The replacing structure such as position, meta, the binding site at ortho position and cyano group, fluorine, methyl, the tert-butyl group.
A, a-MADN and b in the compound, the situation of b-MADN is with a, a-AND and b, b-AND comparative structure discrepancys It is many methyl, but the stereochemical structure with SK-1 and BD1 device result methyl improves performance.Adv.Mater.2005,17, 2493-2497, APPLIED PHYSICS LETTERS 91083515 (2007) and Current Applied Physics 8 (2008) 573-576 it has been reported that.
Develop into maximization in oled panel, need the finer and smoother and distincter material of color, wherein solve it is important that Blue material, especially need it is light blue move on to navy blue high performance material, on the other hand need emission wavelength chromaticity coordinates, The good high glass transition temperature material of high efficiency light-emitting efficiency and heat stability.
The content of the invention
In view of this, the technical problem to be solved in the present invention is to provide a kind of dianthranide derivant and preparation method thereof and answer With the dianthranide derivant that the present invention is provided is blue emitting material, and the material is with higher luminous efficiency and well Life-span.
The invention provides a kind of dianthranide derivant, with formula (I) or structure shown in formula (II)：
In formula (I) or formula (II), A independences selected from C1～C60Alkyl, C6～C60Aryl, C5～C60Condensed ring radical Or C5～C60Heterocyclic radical；
Ar independences selected from C5～C60Condensed ring radical, C5～C60Heterocyclic radical or C6～C60Aryl；
L1And L2It is independent selected from 0～2 integer；
R1Selected from hydrogen, halogen, C1～C60Alkyl, C1～C60Ether, C6～C60Aryl, C5～C60Condensed ring radical or C5～C60 Heterocyclic radical；
R2And R3It is independent selected from C6～C60Aryl, C5～C60Condensed ring radical and C5～C60Heterocyclic radical, the C6～C60 Aryl, C5～C60Condensed ring radical or C5～C60Heterocyclic radical optionally by more than one halogen, C1～C60Alkyl, C1 ～C60Alkoxyl, C1～C60Substituted-amino, C1～C60Substituted sulfhydryl, C2～C60Alkynes base, C6～C60Aryl, C8 ～C60Arylalkenyl, silicon substrate and C5～C60Heterocyclic radical replaced.
Preferably, the A independences selected from C1～C30Alkyl, C6～C30Aryl or C5～C30Heterocyclic radical；
The Ar independences selected from C5～C30Condensed ring radical, C5～C30Heterocyclic radical or C6～C30Aryl；
The L1And L2It is independent selected from 0 or 1；
The R1Selected from hydrogen, halogen, C1～C30Alkyl, C1～C30Ether, C6～C30Aryl, C5～C30Condensed ring radical or C5 ～C30Heterocyclic radical；
R2And R3It is independent selected from C6～C30Aryl, C5～C30Condensed ring radical and C5～C30Heterocyclic radical, the C6～C30 Aryl, C5～C30Condensed ring radical or C5～C30Heterocyclic radical optionally by more than one halogen, C1～C30Alkyl, C1 ～C30Alkoxyl, C1～C30Substituted-amino, C1～C30Substituted sulfhydryl, C2～C30Alkynes base, C6～C30Aryl, C8 ～C30Arylalkenyl, silicon substrate and C5～C30Heterocyclic radical replaced.
Preferably, the A independences selected from methyl, phenyl or pyridine radicals；
The Ar is selected from selected from independent Wherein, X selected from independent selected from CH, N or C- R4；R4Selected from C1～C60Alkyl, C1～C60Ether, C6～C60Aryl, C6～C60Fragrant amino, C5～C60Condensed ring radical, C5～C60 Heterocyclic radical；
The R1 selected from H, methoxyl group, naphthyl, pyridine radicals, Wherein, Y is selected from C6～C60Aryl, C5～C60Condensed ring Base or C5～C60Heterocyclic radical；R4、R5Or R6It is independent selected from hydrogen, halogen, C1～C60Alkyl, C1～C60Alkoxyl, C6~ C60Aryl, C8～C60Condensed ring radical, C8～C60Heterocyclic radical
R2Or R3It is independent selected from phenyl, pyridine radicals or
Preferably, the Ar independences are selected from
The R1Selected from H, methoxyl group, naphthyl, pyridine radicals,
Preferably, the compound has following E-1～E-51 any structures：
Present invention also offers a kind of preparation method of dianthranide derivant, comprises the following steps：
Compound shown in formula (III) and compound shown in formula (IV) are reacted, is obtained with structure shown in formula (I) Dianthranide derivant；
Or, compound shown in formula (III) and compound shown in formula (V) are reacted, is obtained with formula (II) Suo Shi The dianthranide derivant of structure；
Wherein, M is selected from-Br, I or F；
Y1 is-B (OH)2、-B(OCH(CH3)2)2Or
A independences selected from C1～C60Alkyl, C6～C60Aryl, C5～C60Condensed ring radical or C5～C60Heterocyclic radical；
Ar independences selected from C5～C60Condensed ring radical, C5～C60Heterocyclic radical or C6～C60Aryl；
L1And L2It is independent selected from 0～2 integer；
R1Selected from hydrogen, halogen, C1～C60Alkyl, C1～C60Ether, C6～C60Aryl, C5～C60Condensed ring radical or C5～C60 Heterocyclic radical；
R2And R3It is independent selected from C6～C60Aryl, C5～C60Condensed ring radical and C5～C60Heterocyclic radical, the C6～C60 Aryl, C5～C60Condensed ring radical or C5～C60Heterocyclic radical optionally by more than one halogen, C1～C60Alkyl, C1 ～C60Alkoxyl, C1～C60Substituted-amino, C1～C60Substituted sulfhydryl, C2～C60Alkynes base, C6～C60Aryl, C8 ～C60Arylalkenyl, silicon substrate and C5～C60Heterocyclic radical replaced.
Preferably, compound shown in the formula (III) is prepared as follows：
Compound shown in formula (V) is reacted with triisopropyl borate ester or connection boric acid pinacol ester, is obtained with formula (VI) compound of structure shown in；
Compound shown in formula (VI) and compound shown in formula (VIII) are reacted, obtains tying with formula (III) Suo Shi The compound of structure；
Present invention also offers a kind of luminous organic material, including prepared by above-mentioned dianthranide derivant or above-mentioned preparation method Dianthranide derivant.
Present invention also offers a kind of organic electronic device, including first electrode, second electrode and it is arranged at described first Organic matter layer between electrode and second electrode；The organic matter layer includes prepared by above-mentioned dianthranide derivant or above-mentioned preparation method Dianthranide derivant, the organic matter layer is selected from hole injection layer, hole transmission layer and hole injection technical ability and hole transport skill The technical ability layer that can be provided simultaneously with, in electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer and electron injecting layer Plant or various.
Preferably, organic electronic device include organic luminescent device, organic photovoltaic cell, Electronic Paper, Organophotoreceptor or OTFT.
Compared with prior art, the invention provides a kind of dianthranide derivant, with formula (I) or structure shown in formula (II)： In formula (I) or formula (II), A independences selected from C1～C60Alkyl, C6～C60Aryl, C5～C60Condensed ring radical or C5～C60 Heterocyclic radical；Ar independences selected from C5～C60Condensed ring radical, C5～C60Heterocyclic radical or C6～C60Aryl；L1And L2Independent Selected from 0～2 integer；R1Selected from hydrogen, halogen, C1～C60Alkyl, C1～C60Ether, C6～C60Aryl, C5～C60Condensed ring radical Or C5～C60Heterocyclic radical；R2And R3It is independent selected from C6～C60Aryl, C5～C60Condensed ring radical and C5～C60Heterocyclic radical, The C6～C60Aryl, C5～C60Condensed ring radical or C5～C60Heterocyclic radical optionally by more than one halogen, C1~ C60Alkyl, C1～C60Alkoxyl, C1～C60Substituted-amino, C1～C60Substituted sulfhydryl, C2～C60Alkynes base, C6~ C60Aryl, C8～C60Arylalkenyl, silicon substrate and C5～C60Heterocyclic radical replaced.The dianthranide derivant that the present invention is provided is logical Cross different groups are introduced in dianthranide compound with form unsymmetric structure so as to improve dianthranide derivant stereoeffect and The wavelength of dianthranide derivant is adjusted, Ar is adjusted in addition2Molecular weight, R1、R3Species improve the performance of material, and then using this The characteristics of organic assembly of the dianthranide derivant that invention is provided has high brightness, good thermostability, life-span length and efficiency high.
Specific embodiment
A kind of dianthranide derivant, with formula (I) or structure shown in formula (II)：
In formula (I) or formula (II), A independences selected from C1～C60Alkyl, C6～C60Aryl, C5～C60Condensed ring radical Or C5～C60Heterocyclic radical；
Ar independences selected from C5～C60Condensed ring radical, C5～C60Heterocyclic radical or C6～C60Aryl；
L1And L2It is independent selected from 0～2 integer；
R1Selected from hydrogen, halogen, C1～C60Alkyl, C1～C60Ether, C6～C60Aryl, C5～C60Condensed ring radical or C5～C60 Heterocyclic radical；
R2And R3It is independent selected from C6～C60Aryl, C5～C60Condensed ring radical and C5～C60Heterocyclic radical, the C6～C60 Aryl, C5～C60Condensed ring radical or C5～C60Heterocyclic radical optionally by more than one halogen, C1～C60Alkyl, C1 ～C60Alkoxyl, C1～C60Substituted-amino, C1～C60Substituted sulfhydryl, C2～C60Alkynes base, C6～C60Aryl, C8 ～C60Arylalkenyl, silicon substrate and C5～C60Heterocyclic radical replaced.
In the present invention, described " alkyl " including straight chained alkyl, branched alkyl and cycloalkyl, while also include replace or not Substituted alkyl.
" aryl " is including substituted or unsubstituted aryl.
" condensed ring radical " is including substituted or unsubstituted condensed ring radical.
" heterocyclic radical " is including substituted or unsubstituted heterocyclic radical.
" ether " is including substituted or unsubstituted ether.
" silicon substrate " is including substituted or unsubstituted silicon substrate.
" substituted-amino " includes alkyl-substituted amino, aryl substituted-amino.
" substituted sulfhydryl " includes alkyl substituted sulfhydryl, aryl substituted sulfhydryl.
Preferably, the A independences selected from C1～C30Alkyl, C6～C30Aryl or C5～C30Heterocyclic radical；
The Ar independences selected from C5～C30Condensed ring radical, C5～C30Heterocyclic radical or C6～C30Aryl；
The L1And L2It is independent selected from 0 or 1；
The R1Selected from hydrogen, halogen, C1～C30Alkyl, C1～C30Ether, C6～C30Aryl, C5～C30Condensed ring radical or C5 ～C30Heterocyclic radical；
R2And R3It is independent selected from C6～C30Aryl, C5～C30Condensed ring radical and C5～C30Heterocyclic radical, the C6～C30 Aryl, C5～C30Condensed ring radical or C5～C30Heterocyclic radical optionally by more than one halogen, C1～C30Alkyl, C1 ～C30Alkoxyl, C1～C30Substituted-amino, C1～C30Substituted sulfhydryl, C2～C30Alkynes base, C6～C30Aryl, C8 ～C30Arylalkenyl, silicon substrate and C5～C30Heterocyclic radical replaced.
In some embodiments of the invention, the A independences selected from methyl, phenyl or pyridine radicals；
The Ar is selected from selected from independent Wherein, X selected from independent selected from CH, N or C-R4；R4Selected from C1～C60Alkane Base, C1～C60Ether, C6～C60Aryl, C6～C60Fragrant amino, C5～C60Condensed ring radical, C5～C60Heterocyclic radical；
The R1Selected from H, methoxyl group, naphthyl, pyridine radicals, Wherein, Y is selected from C6～C60Aryl, C5～C60Condensed ring radical or C5～C60Heterocyclic radical；R4、R5Or R6It is independent selected from hydrogen, halogen, C1～C60Alkyl, C1～C60 Alkoxyl, C6～C60Aryl, C8～C60Condensed ring radical, C8～C60Heterocyclic radical；
R2Or R3It is independent selected from phenyl, pyridine radicals or
In the present invention, to above-mentioned A, Ar, R1、R2Or R3The replacement of group and substituted position do not have special limit System.
Further, in some specific embodiments of the present invention, the Ar independences are selected from
The R1Selected from H, methoxyl group, naphthyl, pyridine radicals,
In some specific embodiments of the present invention, the compound has following E-1～E-51 any structures：
Compound shown in formula (III) and compound shown in formula (IV) are reacted, is obtained with structure shown in formula (I) Dianthranide derivant；
Or, compound shown in formula (III) and compound shown in formula (V) are reacted, is obtained with formula (II) Suo Shi The dianthranide derivant of structure；
Wherein, M is selected from-Br, I or F；
Y1For-B (OH)2、-B(OCH(CH3)2)2Or
A independences selected from C1～C60Alkyl, C6～C60Aryl, C5～C60Condensed ring radical or C5～C60Heterocyclic radical；
Ar independences selected from C5～C60Condensed ring radical, C5～C60Heterocyclic radical or C6～C60Aryl；
L1And L2It is independent selected from 0～2 integer；
R1Selected from hydrogen, halogen, C1～C60Alkyl, C1～C60Ether, C6～C60Aryl, C5～C60Condensed ring radical or C5～C60 Heterocyclic radical；
R2And R3It is independent selected from C6～C60Aryl, C5～C60Condensed ring radical and C5～C60Heterocyclic radical, the C6～C60 Aryl, C5～C60Condensed ring radical or C5～C60Heterocyclic radical optionally by more than one halogen, C1～C60Alkyl, C1 ～C60Alkoxyl, C1～C60Substituted-amino, C1～C60Substituted sulfhydryl, C2～C60Alkynes base, C6～C60Aryl, C8 ～C60Arylalkenyl, silicon substrate and C5～C60Heterocyclic radical replaced.
Compound shown in the formula (III) is prepared as follows：
Compound shown in formula (V) is reacted with triisopropyl borate ester or connection boric acid pinacol ester, is obtained with formula (VI) compound of structure shown in；
Compound shown in formula (VI) and compound shown in formula (VIII) are reacted, obtains tying with formula (III) Suo Shi The compound of structure；
The dianthranide derivant that the present invention is provided when reaction raw materials isWhen, reaction equation is：
When reaction raw materials areWhen, reaction equation is：
The present invention is to the reaction condition of above-mentioned reaction and is not particularly limited, and can be the normal condition of the reaction.
A, Ar, L in above-mentioned preparation method in involved structural formula1、L2、R1、R2、R3Scope and the said goods tie Scope in structure formula is identical, will not be described here.
Present invention also offers a kind of luminescent material, spreads out including the dianthranide for stating dianthranide derivant or the preparation of above-mentioned preparation method It is biological.
Present invention also offers a kind of organic electronic device, including first electrode, second electrode and it is arranged at described first Organic matter layer between electrode and second electrode；The organic matter layer is wrapped and states prepared by dianthranide derivant or above-mentioned preparation method Dianthranide derivant, the organic matter layer is selected from hole injection layer, hole transmission layer and hole injection technical ability and hole transport technical ability The technical ability layer being provided simultaneously with, the one kind in electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer and electron injecting layer Or it is various.
In the present invention, the organic matter layer refers to the whole layers between organic electronic device first electrode and second electrode. At least one of which in the organic matter layer includes at least one above-mentioned dianthranide derivant, and which is used as electron transfer layer.It is described organic Electronic device is preferably organic electroluminescence device.
In the present invention, the dianthranide derivant can be single form, it is also possible to add to above-mentioned with other material mixings In organic layer, the present invention is to this and is not particularly limited.
According to the present invention, the organic matter layer preferably include hole injection layer, hole transmission layer, not only possessed hole injection 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 but also with one or more layers in electron injection technical ability layer, more preferably including the hole injection layer, sky for setting gradually Cave transport layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer and electron injecting layer or the both tools for setting gradually Standby hole inject but also with hole transport technical ability layer, electronic barrier layer, luminescent layer, hole blocking layer and not only possess electric transmission but also Possesses electron injection technical ability layer.
Pass but also with hole when organic matter layer of the present invention includes hole injection layer, hole transmission layer or both possessed hole injection During defeated technical ability layer, preferably the hole injection layer, hole transmission layer or both possessed hole and injected but also with hole transport technical ability layer Middle at least one of which includes hole injecting material, hole transporting material or had both possessed thing of the hole injection but also with hole transport technical ability Matter, or the material that electron-transporting material is generated.
Preferably, when the organic matter layer is multiple structure, the organic matter layer includes luminescent layer；In the luminescent layer Preferably include one or more in phosphorescence host, fluorescent host, phosphorescence dopant material and fluorescence dopant material；Wherein above-mentioned Photosphere includes above-mentioned dianthranide derivant, point three kinds of situations：I) above-mentioned fluorescent host can be above-mentioned dianthranide derivant ii) it is above-mentioned Fluorescence doping can be above-mentioned dianthranide derivant iii) above-mentioned fluorescent host and fluorescence doping can be above-mentioned dianthranide derivant.
Above-mentioned luminescent layer is can also red, yellow or cyan luminescent layer.Such as, above-mentioned dianthranide during above-mentioned luminescent layer cyan Derivant is using in cyan main body or cyan doping purposes, there is provided high efficiency, high brightness, high-resolution and long-life organic Optical device.
And when above-mentioned organic layer includes electron transfer layer, above-mentioned electron transfer layer includes above-mentioned dianthranide derivant.It is excellent Choosing, above-mentioned electron transfer layer includes that the derivative beyond the region of objective existence of above-mentioned dianthranide also includes the compound containing metal.The metallic compound For the material for electric transmission well known to those skilled in the art, special restriction is had no.
When above-mentioned organic layer includes luminescent layer and electron transfer layer, above-mentioned luminescent layer and electron transfer layer are each including above-mentioned Dianthranide derivant, wherein, above-mentioned luminescent layer and electron transfer layer include that the species of above-mentioned dianthranide derivant can also be identical Can be with difference.
The organic electronic device that the present invention is provided is made using the dianthranide derivant and conventional material described in chemical formula (I) , the present invention is to the preparation method of the organic electroluminescence device and is not limited, this area conventional method.
Preparation of the present invention to the organic electronic device does not have particular restriction, preferably：Organic luminescent device is profit With methods such as film vapor deposition, electron beam evaporation, physical vapour deposition (PVD)s on substrate evaporation metal and the oxide with electric conductivity And their alloy forms anode, is then formed on organic matter layer and evaporation cathode, obtains organic electroluminescence device.
The 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 Mutually the method such as deposition is deposited with, 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 is provided according to using material can also be divided into above luminous, back side illuminated or Lighting at two sides；The organic electronic device that the present invention is provided is used in organic luminescent device (OLED), organic sun with same principle On battery (OSC), Electronic Paper (e-Paper), Organophotoreceptor (OPC) or OTFT (OTFT).
The present invention provide formula (I) shown in dianthranide derivant organic photovoltaic cell, illumination with OLED, flexibility OLED, Also can be suitable for according to the principle for being suitable for organic luminescent device in the organic assembly such as Organophotoreceptor and organic transistor.
For a further understanding of the present invention, the dianthranide derivant provided to the present invention with reference to embodiment and its preparation side Method and application are illustrated, and protection scope of the present invention is not limited by the following examples.
The preparation of 1 intermediate 10- methoxyl groups anthracene -9- ylboronic acids (A-1) of embodiment
In N2Under protection, ventilation three times after, tetrahydrofuran solution 100ml and 9- bromo- 10- methoxyl groups anthracene 20.3mmol is added Enter in there-necked flask, control temperature starts stirring, n-BuLi 8.9ml is slowly dropped to reaction bulb after 60min at -78 DEG C In, said temperature is continued to, when there is white emulsion, 60min is stirred, Deca triisopropyl borate ester 24.4mmol continues 3 hours of stirring, return to room temperature, are continuing reaction overnight at normal temperatures, are detecting extent of reaction with TLC.
Reaction process is tracked with TLC, it is determined that after reaction terminates, acidifying adds water, and (upper strata for reaction solution is point liquid：Tetrahydrochysene Tetrahydrofuran solution), water layer is extracted three times with dichloromethane, and resulting solution is steamed using Rotary Evaporators, is taken out after adding petroleum ether Filter obtain white solid, gained white solid product is dried into 3h at 50 DEG C, obtain A-1 (15.02mmol, 75%).
The preparation of the bromo- 10'- methoxyl groups -9,9'- dianthranides (A-2) of 2 intermediate 10- of embodiment
In N2Protection under, take a breath three times, by solvent toluene/water=3:1(60ml:20ml), (10- methoxyl group anthracene -9- Base) boric acid 32.6mmol, 9,10- dibromoanthracene 32.6mmol, potassium carbonate 81.5mmol, while being added in above-mentioned there-necked flask, open Begin to stir, after 30min, add catalyst tetra-triphenylphosphine palladium 0.98mmol, then after taking a breath once, be warming up to 60 DEG C of backflows, instead 20h or so between seasonable.
Processing procedure：Detected with TLC, cross kieselguhr (drainage type), rinsed with DCM, point liquid rotates solvent, cross silica gel leakage Bucket, eluant:DCM/PE=10：Solution is rotated by 1, with PE recrystallization after, be filtrated to get product, by gained white solid product Dry 3h at 50 DEG C, obtain A-2 (24.45,75.0%).
The preparation of the bromo- 10'- phenoxy groups -9,9'- dianthranides (A-3) of 3 intermediate 10- of embodiment
Sodium phenate 10mmol is added in 100mL there-necked flasks, is dissolved in 50ml acetonitriles, afterwards plus cesium carbonate 20mmol, copper 0.2mmol, 10,10'- bis- bromo- 9,9'- dianthranides 11mmol, the lower 80 DEG C of reactions 4h of nitrogen protection, extract after anti-beam, are evaporated organic Phase column chromatography obtains product A-3 (7.2mmol, y=72%).
The preparation of 4 intermediate 4- of embodiment (the bromo- bis- anthracene -10- base epoxides of 9,9'- of 10'-) pyridine (A-4)
4- pyridine sodium alkoxide 10mmol are added in 100mL there-necked flasks, is dissolved in 50ml acetonitriles, afterwards plus cesium carbonate Bromo- 9, the 9'- dianthranides 11mmol of 20mmol, copper 0.2mmol, 10,10'- bis-, the lower 80 DEG C of reactions 4h of nitrogen protection, after reaction terminates Extraction, is evaporated organic faciess column chromatography and obtains product A-4 (7.3mmol, y=73%).
The bromo- N of 5 intermediate 7- of embodiment, the preparation of N- diphenyl phenanthrene -2- amine (B-1)
Under condition of nitrogen gas, diphenylamines 100mmol, 2,7- dibromos phenanthrene 100mmol, Phen 1.98g, Hydro-Giene (Water Science). 1.90g, cesium carbonate 38.6g, it is dissolved in toluene 300mL, heats 110 DEG C, reacts 7h, cooling room temperature is filtered, and removes metal object Matter, solvent revolving obtain solid B-1 (60mmol, 60%).
The preparation of 6-2～B-4 of intermediate B of embodiment
The preparation method of the intermediate B -1 provided according to embodiment 5, with same molar than preparing shown in table 1 Compound.
1 embodiment of the present invention of table, 6 reactant, product and yield collect
The preparation of 7 intermediate C-1 of embodiment
In N2Under protection, ventilation three times after, by tetrahydrofuran solution (100ml) and the bromo- N of 7-, N- diphenyl phenanthrene -2- amine 20.3mmol is added in there-necked flask, and control temperature starts stirring at -78 DEG C, n-BuLi (8.9ml) is slow after 60min It is added drop-wise in reaction bulb, continues to said temperature, when there is white emulsion, stirs 60min, Deca triisopropyl borate ester 24.4mmol continues 3 hours of stirring, returns to room temperature, is continuing reaction overnight at normal temperatures, is detecting extent of reaction with TLC. Reaction process is tracked with TLC, it is determined that after reaction terminates, acidifying adds water, and (upper strata for reaction solution is point liquid：Tetrahydrofuran is molten Liquid), water layer is extracted three times with dichloromethane, and resulting solution is steamed using Rotary Evaporators, and after adding petroleum ether, sucking filtration is obtained Gained white solid product is dried 3h at 50 DEG C by white solid, obtain C-1 (15.02mmol, 74%).
The preparation of 8 intermediate C-2 of embodiment～C-4
The preparation method of the intermediate C-1 provided according to embodiment 7, with same molar than preparing shown in table 2 Compound.
2 embodiment of the present invention of table, 8 reactant, product and yield collect
The preparation of 9 intermediate 7- (pyridin-4-yl) naphthalene -2- ylboronic acids (D-1) of embodiment
In N2Protection under, take a breath three times, by solvent toluene/water=3:1(60ml:20ml), 2,7- naphthyls hypoboric acid 32.6mmol, 4- bromopyridine 32.6mmol, potassium carbonate 81.5mmol, while being added in above-mentioned there-necked flask, start stirring, After 30min, catalyst tetra-triphenylphosphine palladium 0.98mmol is added, then after taking a breath once, is warming up to 60 DEG C of backflows, response time 20h or so.Detected with TLC, cross kieselguhr (drainage type), rinsed with DCM, point liquid rotates solvent, crosses silica gel funnel, eluant: DCM/PE=10：Solution is rotated by 1, with PE recrystallization after, be filtrated to get product, gained white solid product dried at 50 DEG C 3h, obtain D-1 (24.45mmol, 75.0%).
The preparation of 10 intermediate D-2 of embodiment～D-11
The preparation method of the intermediate D-1 provided according to embodiment 10, with same molar than preparing shown in table 3 Compound.
3 embodiment of the present invention of table, 10 reactant, product and yield collect
The preparation of 11 E-1 of embodiment
In N2Protection under, take a breath three times, by solvent toluene/water=3:1(60ml:20ml), (2- methoxyphenyls) boron Bromo- 10'- methoxyl group -9 of sour 32.6mmol, 10-, 9'- dianthranide 32.6mmol, potassium carbonate 81.5mmol, while being added to above-mentioned three In mouth bottle, start stirring, after 30min, add catalyst tetra-triphenylphosphine palladium 0.98mmol, then after taking a breath once, be warming up to 60 DEG C backflow, response time 20h or so.Detected with TLC, cross kieselguhr (drainage type), rinsed with DCM, point liquid rotates solvent, mistake Silica gel funnel, eluant:DCM/PE=10：Solution is rotated by 1, with PE recrystallization after, be filtrated to get product, will be gained white solid Body product dries 3h at 50 DEG C, obtain E-1 (24.29mmol, 74.5%).Mass spectrum：490.22.
The preparation of embodiment 12E-2～E-46
The preparation method of the E-1 provided according to embodiment 11, with same molar than preparing the chemical combination shown in table 4 Thing.
6 embodiment of the present invention of table, 12 reactant, product and yield collect
The preparation of 13 compound E-47 of embodiment
Under condition of nitrogen gas, bromo- 10'- methoxyl group -9 of 2- Methoxy-N-phenyl amine (100mmol), 10-, bis- anthracenes of 9'- (100mmol) materials such as, Phen (1.98g), Hydro-Giene (Water Science). (1.90g), cesium carbonate (38.6g, 2eq), are dissolved in toluene (300mL) 110 DEG C of heating in, reacts 7h, and cooling room temperature is filtered, and removes metallicses, and solvent revolving obtains solid E-47 (62mmol, 62%).Mass spectrum：581.25.
The preparation of 14 compound E-48 of embodiment～E-51
The preparation method of the E-47 provided according to embodiment 13, with same molar than preparing the chemical combination shown in table 7 Thing.
7 embodiment of the present invention of table, 14 reactant, product and yield collect
Embodiment 13
By Fisher Co., Ltd's coating layer thickness it isIto glass substrate be placed in distilled water and clean 2 times, ultrasound wave is washed Wash 30 minutes, cleaned repeatedly 2 times with distilled water, ultrasonic washing 10 minutes, after distilled water cleaning terminates, isopropanol, acetone, first Alcohol equal solvent is dried after ultrasonic washing in order, is transferred in plasma washing machine, and aforesaid substrate is washed 5 minutes, It is sent in evaporator.Hole injection layer 2-TNATA evaporations will be deposited with the ito transparent electrode being already prepared toHole passes Embodiment material or (9,10- bis- (2- naphthyls) anthracene) and dopant material TPPDA (N described in defeated layer a-NPD or table 71, N1, N6, N6- tetraphenyl pyrene -1,6- diamidogen) 5% mixingThickness evaporation, hole blocking layer and hole transmission layerIt is cloudy Pole Said process organic matter vaporization plating speed is to maintainLiF isAl is
Evaporation is finished and obtains luminescent device, and the performance characteristics of luminescence test of the device to obtaining, measurement adopt KEITHLEY 2400 type source measuring unit of Keithley, CS-2000 spectroradio luminance meters, to evaluate driving voltage, luminosity lights and imitates Rate.8 are the results are shown in Table, table 8 is part of compounds prepared by the embodiment of the present invention and compares sending out for the luminescent device of material preparation Light characteristic test result.
The characteristics of luminescence test result of luminescent device prepared by 8 embodiment of the present invention of table 11～14
Result can be seen that the dianthranide derivant for providing luminous efficiency and life-span in blue light action of the invention as shown in Table 8 Characteristic increases significantly.
The present invention can obtain luminous efficiency and life-span good knot using organic luminescent device prepared by dianthranide derivant Really, therefore, the present invention provide dianthranide derivant in OLED industries have higher practicality.Involved in the present invention is organic Luminescent device can be shown in flat panel, planar illuminant, illumination face illuminating OLED luminous body, flexible luminous body, duplicate It is adapted to use in the light source of machine, printer, LCD backlight lamp or dosing machine class, display panel, mark.
The above is only the preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art For member, under the premise without departing from the principles of the invention, some improvements and modifications can also be made, these improvements and modifications also should It is considered as protection scope of the present invention.

Claims (10)

1. a kind of dianthranide derivant, with formula (I) or structure shown in formula (II)：
In formula (I) or formula (II), A independences selected from C1～C60Alkyl, C6～C60Aryl, C5～C60Condensed ring radical or C5 ～C60Heterocyclic radical；
Ar independences selected from C5～C60Condensed ring radical, C5～C60Heterocyclic radical or C6～C60Aryl；
L1And L2It is independent selected from 0～2 integer；
R1Selected from hydrogen, halogen, C1～C60Alkyl, C1～C60Ether, C6～C60Aryl, C5～C60Condensed ring radical or C5～C60It is miscellaneous Ring group；
R2And R3It is independent selected from C6～C60Aryl, C5～C60Condensed ring radical and C5～C60Heterocyclic radical, the C6～C60Virtue Base, C5～C60Condensed ring radical or C5～C60Heterocyclic radical optionally by more than one halogen, C1～C60Alkyl, C1～C60 Alkoxyl, C1～C60Substituted-amino, C1～C60Substituted sulfhydryl, C2～C60Alkynes base, C6～C60Aryl, C8～C60 Arylalkenyl, silicon substrate and C5～C60Heterocyclic radical replaced.
2. dianthranide derivant according to claim 1, it is characterised in that the A independences selected from C1～C30Alkyl, C6 ～C30Aryl or C5～C30Heterocyclic radical；
The Ar independences selected from C5～C30Condensed ring radical, C5～C30Heterocyclic radical or C6～C30Aryl；
The L1And L2It is independent selected from 0 or 1；
The R1Selected from hydrogen, halogen, C1～C30Alkyl, C1～C30Ether, C6～C30Aryl, C5～C30Condensed ring radical or C5～C30 Heterocyclic radical；
R2And R3It is independent selected from C6～C30Aryl, C5～C30Condensed ring radical and C5～C30Heterocyclic radical, the C6～C30Virtue Base, C5～C30Condensed ring radical or C5～C30Heterocyclic radical optionally by more than one halogen, C1～C30Alkyl, C1～C30 Alkoxyl, C1～C30Substituted-amino, C1～C30Substituted sulfhydryl, C2～C30Alkynes base, C6～C30Aryl, C8～C30 Arylalkenyl, silicon substrate and C5～C30Heterocyclic radical replaced.
3. dianthranide derivant according to claim 1, it is characterised in that the A independences selected from methyl, phenyl or pyridine Base；
The Ar is selected from selected from independent Wherein, X selected from independent selected from CH, N or C- R4；R4Selected from C1～C60Alkyl, C1～C60Ether, C6～C60Aryl, C6～C60Fragrant amino, C5～C60Condensed ring radical, C5～C60 Heterocyclic radical；
The R1 selected from H, methoxyl group, naphthyl, pyridine radicals, Wherein, Y is selected from C6～C60 Aryl, C5～C60Condensed ring radical or C5～C60Heterocyclic radical；R4、R5Or R6It is independent selected from hydrogen, halogen, C1～C60Alkyl, C1 ～C60Alkoxyl, C6～C60Aryl, C8～C60Condensed ring radical, C8～C60Heterocyclic radical；
R2Or R3It is independent selected from phenyl, pyridine radicals or
4. dianthranide derivant according to claim 1, it is characterised in that
The Ar independences are selected from
The R1Selected from H, methoxyl group, naphthyl, pyridine radicals,
5. dianthranide derivant according to claim 4, it is characterised in that there is the compound following E-1～E-51 to appoint One structure：
6. a kind of preparation method of dianthranide derivant, it is characterised in that comprise the following steps：
Compound shown in formula (III) and compound shown in formula (IV) are reacted, the dianthranide with structure shown in formula (I) is obtained Derivant；
Or, compound shown in formula (III) and compound shown in formula (V) are reacted, is obtained with structure shown in formula (II) Dianthranide derivant；
Wherein, M is selected from-Br, I or F；
Y1For-B (OH)2、-B(OCH(CH3)2)2Or
A independences selected from C1～C60Alkyl, C6～C60Aryl, C5～C60Condensed ring radical or C5～C60Heterocyclic radical；
Ar independences selected from C5～C60Condensed ring radical, C5～C60Heterocyclic radical or C6～C60Aryl；
L1And L2It is independent selected from 0～2 integer；
R1Selected from hydrogen, halogen, C1～C60Alkyl, C1～C60Ether, C6～C60Aryl, C5～C60Condensed ring radical or C5～C60It is miscellaneous Ring group；
R2And R3It is independent selected from C6～C60Aryl, C5～C60Condensed ring radical and C5～C60Heterocyclic radical, the C6～C60Virtue Base, C5～C60Condensed ring radical or C5～C60Heterocyclic radical optionally by more than one halogen, C1～C60Alkyl, C1～C60 Alkoxyl, C1～C60Substituted-amino, C1～C60Substituted sulfhydryl, C2～C60Alkynes base, C6～C60Aryl, C8～C60 Arylalkenyl, silicon substrate and C5～C60Heterocyclic radical replaced.
7. preparation method according to claim 5, it is characterised in that compound is according to such as lower section shown in the formula (III) Method is prepared：
Compound shown in formula (V) is reacted with triisopropyl borate ester or connection boric acid pinacol ester, is obtained with formula (VI) institute Show the compound of structure；
Compound shown in formula (VI) and compound shown in formula (VIII) are reacted, is obtained with structure shown in formula (III) Compound；
8. a kind of luminous organic material, it is characterised in that including dianthranide derivant or power described in any one of Claims 1 to 5 Profit requires dianthranide derivant prepared by the preparation method described in 6～7 any one.
9. a kind of organic electronic device, it is characterised in that including first electrode, second electrode and be arranged at the first electrode with Organic matter layer between second electrode；The organic matter layer includes dianthranide derivant or power described in any one of Claims 1 to 5 Profit requires dianthranide derivant prepared by the preparation method described in 6～7 any one, and the organic matter layer is selected from hole injection layer, sky The technical ability layer that cave transport layer and hole injection technical ability and hole transport technical ability are provided simultaneously with, electronic barrier layer, luminescent layer, hole resistance One or more in barrier, electron transfer layer and electron injecting layer.
10. organic electronic device according to claim 9, it is characterised in that organic electronic device includes organic illuminator Part, organic photovoltaic cell, Electronic Paper, Organophotoreceptor or OTFT.
CN201611007921.6A 2016-11-16 2016-11-16 Dianthranide derivative, preparation method, and application thereof Pending CN106588592A (en)

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Publication number Priority date Publication date Assignee Title
CN109956897A (en) * 2019-04-24 2019-07-02 上海钥熠电子科技有限公司 The compound of 9,9 '-dianthranide derivatives of one kind, OLED display panel and electronic equipment comprising it
CN111434658A (en) * 2019-01-15 2020-07-21 机光科技股份有限公司 Organic electroluminescent materials and devices

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111434658A (en) * 2019-01-15 2020-07-21 机光科技股份有限公司 Organic electroluminescent materials and devices
CN109956897A (en) * 2019-04-24 2019-07-02 上海钥熠电子科技有限公司 The compound of 9,9 '-dianthranide derivatives of one kind, OLED display panel and electronic equipment comprising it

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